N-Thio-anthranilamid compounds and their use as pesticides
N-Thio-anthranilamid compounds of formula (I) wherein A is A1 wherein the variables and the indices are as defined per the description, processes for preparing the compounds I, pesticidal compositions comprising compounds I, use of compounds I for the control of insects, acarids or nematodes, and methods for treating, controlling, preventing or protecting animals against infestation or infection by parasites by use of compounds of formula I.
This application is a continuation of U.S. application Ser. No. 14/739,467, filed Jun. 15, 2015, now U.S. Pat. No. 9,365,543, the entire contents of which are hereby incorporated herein by reference. U.S. application Ser. No. 14/739,467, is a continuation of U.S. application Ser. No. 14/293,288, filed Jun. 2, 2014, now U.S. Pat. No. 9,056,853, the entire contents of which are hereby incorporated herein by reference. U.S. application Ser. No. 14/293,288, is a continuation of U.S. application Ser. No. 13/682,246, filed Nov. 20, 2012, now U.S. Pat. No. 8,772,289, the entire contents of which are hereby incorporated by reference. U.S. application Ser. No. 13/682,246 is a continuation of U.S. application Ser. No. 13/400,752, filed Feb. 21, 2012, now U.S. Pat. No. 8,338,419, the entire contents of which are hereby incorporated herein by reference. U.S. application Ser. No. 13/400,752, is a continuation of U.S. application Ser. No. 11/994,812, filed Jan. 4, 2008, now U.S. Pat. No. 8,143,292, the entire contents of which are hereby incorporated by reference. U.S. application Ser. No. 11/994,812, is a National Stage application of International Application No. PCT/EP2006/063761, filed Jun. 30, 2006, which claims the benefit of U.S. Provisional Application No. 60/697,166, filed Jul. 7, 2005, the entire contents of each are hereby incorporated herein by reference.
The present invention relates to N-Thio-anthranilamid compounds of formula (I)
wherein
- R1 is hydrogen; or C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, or C3-C8-cycloalkyl, each of which is unsubstituted or substituted with 1 to 5 groups independently selected from halogen, cyano, nitro, hydroxy, C1-C10-alkoxy, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C2-C10-alkoxycarbonyl, C1-C10-alkylamino, di(C1-C10-alkyl)amino and C3-C8-cycloalkylamino; or C1-C10-alkylcarbonyl, C1-C10-alkoxycarbonyl C1-C10-alkylaminocarbonyl, di(C1-C10-alkyl)aminocarbonyl;
- A is a group selected from A1 and A2
wherein
# denotes the binding site;
- R2 and R3 each independently are R6, —C(=G)R7, —C(═NOR7)R7, —C(═NNR72)R7—C(=G)OR7, —C(=G)NR72, —OC(=G) R7, —OC(=G)OR7, —NR7C(=G)R7, —N[C(=G)R7]2, —NR7C(=G)OR7, —C(=G)NR7—NR72, —C(=G)NR7—NR7[C(=G)R7], —NR7—C(=G)NR72, —NR7—NR7C(=G)R7, —NR7—N[C(=G)R7]2, —N[(C=G)R7]—NR72, —NR7—NR7[(C=G)GR7], —NR7[(C=G)NR72, —NR7[C═NR7]R7, —NR7(C═NR7)NR72, —O—NR72, —O—NR7(C=G)R7, —SO2NR72, —NR7SO2R7, —SO2OR7, —OSO2R7, —OR7, —NR72, —SR7, —SiR73, —PR72, —P(=G)R7, —SOR7, —SO2R7, —PG2R72, or —PG3R72; or
- R2 and R3 together with the sulfur atom to which they are attached form a saturated, partially unsaturated or unsaturated 3- to 8-membered ring which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, which ring can be fused with one or two saturated, partially unsaturated or unsaturated 5- to 6-membered rings which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein all of the above rings are unsubstituted or substituted by any combination of 1 to 6 groups R8;
- G is oxygen or sulfur;
- R6 is C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C3-C8-cycloalkynyl, phenyl, naphthyl, biphenyl, or a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein all of these groups are unsubstituted or substituted by any combination of 1 to 6 groups R8;
- R7 is hydrogen or R6;
- R8 is R9; or two groups R8 together with the atoms to which they are attached form a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which may contain 1 to 4 heteroatoms/heterogroups selected from oxygen, nitrogen, sulfur, SO and SO2, and which ring system is unsubstituted or substituted with any combination of 1 to 6 groups R9.
R9 is R10, R11, —C(=G)R10, —C(═NOR10)R10, —C(═NNR102)R10, —C(=G)OR10, —C(=G)NR102, —OC(=G)R10, —OC(=G)OR10, —NR10C(=G)R10, —N[C(=G)R10]2, —NR10C(=G)OR10, —C(=G)NR10—NR102, —C(=G)NR10—NR10[C(=G)R10], —NR10—C(=G)NR102, —NR10—NR10C(=G)R10, —NR10—N[C(=G)R102, —NRC=G)R10]—NR102, —NR10—NR10[(C=G)GR10], —NR10[(C=G)NR102, —NR10[C═NR10]R10, —NR10(C═NR10)NR102, —O—NR102, —O—NR10(C=G)R10, —SO2NR102, —NR10SO2R10, —SO2OR10, —OSO2R10, —OR10, —NR102, —SR10, —SiR103, —PR102, —P(=G)R10, —SOR10, —SO2R10, —PG2R102, —PG3R102, or two groups R9 together are (=G), (═N—R10), (═CR102), (═CHR10), or (═CH2);
- R10 is C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C8-cycloalkyl, C4-C8-cycloalkenyl, C3-C8-cycloalkyl-C1-C4-alkyl, C4-C8-cycloalkenyl-C1-C4-alkyl, C3-C8-cycloalkyl-C2-C4-alkenyl, C4-C8-cycloalkenyl-C2-C4-alkenyl, C1-C10-alkyl-C3-C8-cycloalkyl, C2-C10-alkenyl-C3-C8-cycloalkyl, C2-C10-alkynyl-C3-C8-cycloalkyl, C1-C10-alkyl-C4-C8-cycloalkenyl, C2-C10-alkenyl-C4-C8-cycloalkenyl, C2-C10-alkynyl-C4-C8-cycloalkenyl,
- a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein the above groups are unsubstituted or substituted with any combination of from 1 to 6 groups R11;
- R11 is halogen, cyano, nitro, hydroxy, mercapto, amino, formyl, C1-C10-alkylcarbonyl, C1-C10-alkoxy, C2-C10-alkenyloxy, C2-C10-alkynyloxy, C1-C10-haloalkoxy, C3-C10-haloalkenyloxy, C3-C10-haloalkynyloxy, C3-C8-cycloalkoxy, C4-C8-cycloalkenyloxy, C3-C8-halocycloalkoxy, C4-C8-halocycloalkenyloxy, C3-C8-cycloalkyl-C1-C4-alkoxy, C4-C8-cycloalkenyl-C1-C4-alkoxy, C3-C8-cycloalkyl-C2-C4-alkenyloxy, C4-C8-cycloalkenyl-C2-C4-alkenyloxy, C1-C10-alkyl-C3-C8-cycloalkoxy, C1-C10-alkenyl-C3-C8-cycloalkoxy, C1-C10-alkynyl-C3-C8-cycloalkoxy, C1-C10-alkyl-C3-C8-cycloalkenyloxy, C1-C10-alkenyl-C3-C8-cycloalkenyloxy, C1-C4-alkoxy-C1-C10-alkoxy, C1-C4-alkoxy-C2-C10-alkenyloxy, mono- or di(C1-C10-alkyl)carbamoyl, mono- or di(C1-C10-haloalkyl)carbamoyl, mono- or di(C3-C8-cycloalkyl)carbamoyl, C1-C10-alkoxycarbonyl, C3-C8-cycloalkoxycarbonyl, C1-C10-alkylcarbonyloxy, C3-C8-cyclo alkylcarbonyloxy, C1-C10-haloalkoxycarbonyl, C1-C10-haloalkylcarbonyloxy, C1-C10-alkanamido, C1-C10-haloalkanamido, C2-C10-alkenamido, C3-C8-cycloalkanamido, C3-C8-cycloalkyl-C1-C4-alkanamido, C1-C10-alkylthio, C2-C10-alkenylthio, C2-C10-alkynylthio, C1-C10-haloalkylthio, C2-C10-haloalkenylthio, C2-C10-haloalkynylthio, C3-C8-cycloalkylthio, C3-C8-cycloalkenylthio, C3-C8-halocycloalkylthio, C3-C8-halocycloalkenylthio, C3-C8-cycloalkyl-C1-C4-alkylthio, C4-C8-cycloalkenyl-C1-C4-alkylthio, C3-C8-cycloalkyl-C2-C4-alkenylthio, C4-C8-cycloalkenyl-C2-C4-alkenylthio, C1-C10-alkyl-C3-C8-cycloalkylthio, C1-C10-alkenyl-C3-C8-cycloalkylthio, C1-C10-alkynyl-C3-C8-cycloalkylthio, C1-C10-alkyl-C3-C8-cycloalkenylthio, C1-C10-alkenyl-C3-C8-cycloalkenylthio, C1-C10-alkylsulfinyl, C2-C10-alkenylsulfinyl, C2-C10-alkynylsulfinyl, C1-C10-haloalkylsulfinyl, C2-C10-haloalkenylsulfinyl, C2-C10-haloalkynylsulfinyl, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkenylsulfinyl, C3-C8-halocycloalkylsulfinyl, C3-C8-halocycloalkenylsulfinyl, C3-C8-cycloalkyl-C1-C4-alkylsulfinyl, C4-C8-cycloalkenyl-C1-C4-alkylsulfinyl, C3-C8-cycloalkyl-C2-C4-alkenylsulfinyl, C4-C8-cycloalkenyl-C2-C4-alkenylsulfinyl, C1-C10-alkyl-C3-C8-cycloalkylsulfinyl, C1-C10-alkenyl-C3-C8-cycloalkylsulfinyl, C1-C10-alkynyl-C3-C8-cycloalkylsulfinyl, C1-C10-alkyl-C3-C8-cycloalkenylsulfinyl, C1-C10-alkenyl-C3-C8-cycloalkenylsulfinyl, C1-C10-alkylsulfonyl, C2-C10-alkenylsulfonyl, C2-C10-alkynylsulfonyl, C1-C10-haloalkylsulfonyl, C2-C10-haloalkenylsulfonyl, C2-C10-haloalkynylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkenylsulfonyl, C3-C8-halocycloalkylsulfonyl, C3-C8-halocycloalkenylsulfonyl, C3-C8-cycloalkyl-C1-C4-alkylsulfonyl, C4-C8-cycloalkenyl-C1-C4-alkylsulfonyl, C3-C8-cycloalkyl-C2-C4-alkenylsulfonyl, C4-C8-cycloalkenyl-C2-C4-alkenylsulfonyl, C1-C10-alkyl-C3-C8-cycloalkylsulfonyl, C1-C10-alkenyl-C3-C8-cycloalkylsulfonyl, C1-C10-alkynyl-C3-C8-cycloalkylsulfonyl, C1-C10-alkyl-C3-C8-cycloalkenylsulfonyl, C1-C10-alkenyl-C3-C8-cycloalkenylsulfonyl, di(C1-C10-alkyl)amino, C1-C10-alkylamino, C2-C10-alkenylamino, C2-C10-alkynylamino, C1-C10-alkyl-C2-C10-alkenylamino, C1-C10-alkyl-C2-C10-alkynylamino, C1-C10-haloalkylamino, C2-C10-haloalkenylamino, C2-C10-haloalkynylamino, C3-C8-cycloalkylamino, C3-C8-cycloalkenylamino, C3-C8-halocycloalkylamino, C3-C8-halocycloalkenylamino, C3-C8-cycloalkyl-C1-C4-alkylamino, C4-C8-cycloalkenyl-C1-C4-alkylamino, C3-C8-cycloalkyl-C2-C4-alkenylamino, C4-C8-cycloalkenyl-C2-C4-alkenylamino, C1-C10-alkyl-C3-C8-cycloalkylamino, C1-C10-alkenyl-C3-C8-cycloalkylamino, C1-C10-alkynyl-C3-C8-cycloalkylamino, C1-C10-alkyl-C3-C8-cycloalkenylamino, C1-C10-alkenyl-C3-C8-cycloalkenylamino, tri(C1-C10-alkyl)silyl, aryl, aryloxy, arylthio, arylamino, aryl-C1-C4-alkoxy, aryl-C3-C4-alkenyloxy, aryl-C1-C4-alkylthio, aryl-C2-C4-alkenylthio, aryl-C1-C4-alkylamino, aryl-C3-C4-alkenylamino, aryl-di(C1-C4)silyl, triarylsilyl, wherein aryl is phenyl, naphthyl or biphenyl, or
- a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein these aryl and these heterocyclic ringsystems are unsubstituted or substituted with any combination of from 1 to 6 groups selected from halogen, cyano, nitro, amino, hydroxy, mercapto, C1-C4-alkyl, C1-C4-haloalkyl, C3-C8-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, di(C1-C4-alkyl)amino, C1-C4-alkylamino, C1-C4-haloalkylamino, formyl and C1-C4-alkylcarbonyl;
- R4 is NR12R13;
- R12 and R13 are each independently hydrogen; or C1-C20-alkyl, C2-C20-alkenyl or C2-C20-alkynyl, each of which is unsubstituted or substituted with any combination of 1 to 6 groups selected from C1-C4-alkoxy, C1-C4-alkylthio, cyano, nitro, formyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C3-C8-cycloalkyl, and phenyl, wherein phenyl itself is unsubstituted or substituted by 1 to 4 substituents selected from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-fluoroalkyl, C1-C4-alkyloxycarbonyl, trifluoromethylsulfonyl, formyl, nitro and cyano; or
- C1-C20-haloalkyl, C2-C20-haloalkenyl, C2-C20-haloalkynyl, C5-C10-cycloalkenyl, or a saturated or partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, or phenyl or naphthyl, wherein this ring system and phenyl or naphthyl themselves are unsubstituted or substituted by 1 to 4 substituents selected from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-fluoroalkyl, C1-C4-alkyloxycarbonyl, trifluoromethylsulfonyl, formyl, nitro and cyano; or
- R12 and R13 together with the nitrogen atom to which they are attached form a saturated or partially unsaturated 5- to 8-membered heterocycle which besides the one nitrogen atom contains 0 to 2 further heteroatoms selected from oxygen, nitrogen, sulfur, and may contain 1 or 2 carbonyl groups or thiocarbonyl groups and which is unsubstituted or substituted by from 1 to 4 groups selected from C1-C4-alkyl, C1-C4-alkoxy and C1-C4-haloalkyl;
- R5 is hydrogen; or C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C1-C4-alkylcarbonyl, C1-C4-alkylaminocarbonyl, C1-C4-alkoxycarbonyl, each of which is unsubstituted or substituted by from 1 to 6 groups selected from C1-C4-alkoxy, C1-C4-alkylthio, cyano, nitro, formyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C3-C8-cycloalkyl, and phenyl, wherein phenyl itself is unsubstituted or substituted by 1 to 4 substituents selected from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-fluoroalkyl, C1-C4-alkyloxycarbonyl, trifluoromethylsulfonyl, formyl, nitro and cyano; or
- C1-C20-haloalkyl, C2-C20-haloalkenyl, C2-C20-haloalkynyl, C5-C10-cycloalkenyl, or a saturated or partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, or phenyl or naphthyl, wherein this ring system and phenyl or naphthyl themselves are unsubstituted or substituted by 1 to 4 substituents selected from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-fluoroalkyl, C1-C4-alkyloxycarbonyl, trifluoromethylsulfonyl, formyl, nitro and cyano;
- Q1 and Q2 each independently are hydrogen, halogen, cyano, SCN, nitro, hydroxy, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, C1-C10-alkylsulfonyloxy, C1-C10-haloalkylsulfonyloxy, C1-C10-alkylamino, di(C1-C10-alkyl)amino, C3-C8-cyclalkylamino, alkylcarbonyl, C1-C10-alkoxycarbonyl, C1-C10-alkylaminocarbonyl, di(C1-C10-alkyl)aminocarbonyl, or tri(C1-C10)-alkylsilyl, or
- Q1 and Q2 are each independently phenyl, benzyl or phenoxy, wherein each ring is unsubstituted or substituted with any combination of from 1 to 3 substituents independently selected from the group halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-alkylamino, di(C1-C10-alkyl)amino, C3-C8-cycloalkylamino, C1-C10-alkyl-C3-C8-cycloalkylamino, C1-C10-alkylcarbonyl, C1-C10-alkoxycarbonyl, C1-C10-alkylaminocarbonyl, di(C1-C10-alkyl)aminocarbonyl and tri(C1-C10)-alkylsilyl;
- Q3 is halogen; or C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C10-alkyl-C3-C8-cycloalkyl, C1-C10-haloalkyl-C3-C8-cycloalkyl, each unsubstituted or independently substituted with 1 to 2 groups selected from cyano, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, and C1-C10-alkoxycarbonyl; or
- Q3 is OR14, S(O)qR14, NR15R16, OS(O)2R17, NR16S(O)2R17, C(S)NH2, C(R18)═NOR18, C3-C8-cycloalkyl-C1-C4-alkyl, C1-C10-alkylaminothiocarbonyl, or di(C1-C10-alkyl)aminothiocarbonyl;
- R14 is C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C1-C4-alkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C4-alkyl, C1-C4-haloalkyl-C3-C8-cycloalkyl, or C1-C10-haloalkylcarbonyl, each unsubstituted or substituted with 1 R19;
- R15 is C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C4-alkyl-C3-C8-cycloalkyl, C1-C4-haloalkyl-C3-C8-cycloalkyl, or C1-C10-haloalkylcarbonyl, each unsubstituted or substituted with 1 R19;
- R16 is hydrogen; or C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C4-alkyl-C3-C8-cycloalkyl, or C1-C4-haloalkyl-C3-C8-cycloalkyl, each unsubstituted or substituted with 1 R19;
- R17 is C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C4-alkyl-C3-C8-cycloalkyl, or C1-C4-haloalkyl-C3-C8-cycloalkyl, each unsubstituted or substituted with 1 R19;
- R19 is cyano, nitro, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, C1-C10-alkoxycarbonyl, C1-C10-alkylamino, or di(C1-C10-alkyl)amino; or
- R19 is phenyl or a heteroaromatic 5- or 6-membered ring which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, the phenyl radical and the heteroaromatic ring being unsubstituted or substituted with any combination of from 1 to 3 groups selected from halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-alkylamino, di(C1-C10-alkyl)amino, C3-C8-cycloalkylamino, C1-C10-alkyl-C3-C8-cycloalkylamino, C1-C10-alkylcarbonyl, C1-C10-alkoxycarbonyl, C1-C10-alkylaminocarbonyl, di(C1-C10-alkyl)aminocarbonyl and tri(C1-C10)-alkylsilyl;
- R18 is the same or different: hydrogen, C1-C10-alkyl, or C1-C10-haloalkyl;
- q is 0, 1 or 2;
- Q4 is halogen, cyano, nitro, hydroxy, COOH, C(O)NH2, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, C1-C10-alkylamino, di(C1-C10-alkyl)amino, C3-C8-cycloalkylamino, C1-C10-alkylcarbonyl, C1-C10-alkoxycarbonyl C1-C10-alkylaminocarbonyl, di(C1-C10-alkyl)aminocarbonyl or tri(C1-C10)-alkylsilyl; or
- Q4 is phenyl, benzyl, benzyloxy, phenoxy, a 5- or 6-membered heteroaromatic ring which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein each of the above ring systems is unsubstituted or substituted with any combination of from 1 to 3 groups selected from halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-alkylamino, di(C1-C10-alkyl)amino, C3-C8-cycloalkylamino, C1-C10-alkyl-C3-C8-cycloalkylamino, C1-C10-alkylcarbonyl, C1-C10-alkoxycarbonyl, C1-C10-alkylaminocarbonyl, di(C1-C10-alkyl)aminocarbonyl and tri(C1-C10)-alkylsilyl;
- X and Y are each independently oxygen or sulfur;
- V and V′ are each independently N or CQ2;
- W is N, CH or CQ4;
- m is 0, 1 or 2;
- n is 0 or 1;
- p is 0, 1, 2, 3, or 4;
or the enantiomers or salts or N-oxides thereof.
In addition, the present invention relates to processes for preparing the compounds I, pesticidal compositions comprising compounds I and methods for the control of insects, acarids or nematodes by contacting the insect, acarid or nematode or their food supply, habitat or breeding grounds with a pesticidally effective amount of compounds or compositions of formula I.
Moreover, the present invention also relates to a method of protecting growing plants from attack or infestation by insects or acarids by applying to the foliage of the plants, or to the soil or water in which they are growing, with a pesticidally effective amount of compositions or compounds of formula I.
This invention also provides a method for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of compositions or compounds of formula I.
In spite of the commercial insecticides, acaricides and nematicides available today, damage to crops, both growing and harvested, caused by insects and nematodes still occurs. Therefore, there is continuing need to develop new and more effective insecticidal, acaricidal and nematicidal agents.
It was therefore an object of the present invention to provide new pesticidal compositions, new compounds and new methods for the control of insects, acarids or nematodes and of protecting growing plants from attack or infestation by insects, arachnids or nematodes.
We have found that these objects are achieved by the compositions and the compounds of formula I. Furthermore, we have found processes for preparing the compounds of formula I.
Anthranilamide compounds have been described in a number of patent applications (WO 01/70671, WO 03/015518, WO 03/015519, WO 04/046129). N-Thio-anthranilamide compounds have not been described in the prior art.
Compounds of the formula (I-1) wherein X and Y are oxygen and the other substituents are as defined above for formula (I)
can be prepared by reacting a carboxylic acid of the formula (II)
wherein the variables are as defined for formula (I) in the form of an activated derivative of this acid in the presence of a base with a compound of the formula A1-H or A2-H, respectively, wherein the variables are as defined for formula (I).
Suitable activated derivatives of the acid which may be used are, for example, anhydrides, azolides, or acid halides.
The activated derivatives of the acid can be obtained according to procedures known in the art, e.g. as listed in “Comprehensive Organic Reactions” VCH Publishers 1989, for the anhydride: pp 965-66, for the acid halides: p 978.
Suitable bases are, for example, amines such as triethylamine, diisopropylethylamine, pyridine or lutidine or else alkali hydrides, hydroxides, carbonates, or alkaline earth metal hydroxides, carbonates or bicarbonates.
The amount of the base that can be used in the reaction is usually 1 to 5 moles relative to 1 mole of compound (II).
The reaction is advantageously carried out in an inert solvent such as dichloromethane, chloroform, carbon tetrachloride, benzene, toluene, diethyl ether or tetrahydrofurane, or mixtures of these solvents, in a temperature range between 0° C. and 100° C., preferably between 20° C. and 50° C.
A preferred procedure for the preparation of specific compounds of formula (I-1) involves the reaction of A1-H or A2-H, respectively, with a benzoxazinone of formula (III)
wherein the variables are as defined for formula (I). Typical procedures involve combination of the compounds A1-H or A2-H with the benzoxazinone of formula (III) in inert solvent such as dichloromethane, chloroform, carbon tetrachloride, benzene, toluene, diethyl ether or tetrahydrofurane, or mixtures of these solvents, in a temperature range between 0° C. and 100° C., preferably between 20° C. and 50° C. Addition of a base can be beneficial. Suitable bases are, for example, tertiary amines such as triethylamine, diisopropylethylamine, pyridine or lutidine or else alkali hydrides, hydroxides, carbonates, or alkaline earth metal hydroxides, carbonates or bicarbonates. The amount of the base that can be used in the reaction is usually 1 to 5 moles relative to 1 mole of compound (III).
Benzoxazinones are well documented in the chemical literature and are available via known methods that involve the coupling of either an anthranilic acid or an isatoic anhydride with an acid chloride. For references to the synthesis and chemistry of benzoxazinones see Jakobsen et al, Bioorganic and Medicinal Chemistry, 2000, 8, 2095-2103 and references cited therein. See also Coppola, J. Heterocyclic Chemistry, 1999, 36, 563-588. The benzoxazinones of formula III can also be prepared according to the procedures described in WO 04/046129 or WO 04/011447 as well as according to references cited therein and suitable modifications thereof.
Compounds of the formula (I-2) in which A is A1, n is 0, X and Y are oxygen and the other variables are as defined for formula (I),
can be prepared by reacting an amide of the formula (IV)
wherein the variables are as defined for formula (I), with a sulfoxide of the formula (V),
in the presence of a condensating agent, giving the compounds of formula (I-2) with elimination of water. Suitable condensing agents are, for example, phosphorous oxychloride, phosphorous (V) oxide, methanesulfonyl chloride, sulfuryl chloride, sulfur trichloride, boron triflouride, dicyclohexylcarbodiimide, aryl cyanates or acid anhydrides, preferably triflouroacetic anhydride or triflouromethanesulfonic anhydride.
In the compounds of the formula (I) prepared as described above in which A is A1, n is 0, X and Y are oxygen and the other variables are as defined for formula (I) the sulfur atom can be oxidized to give the respective compounds of the formula (I) in which n is 1. Suitable oxidizing agents are, for example, sodium periodate or organic peracids, such as 3-chloroperbenzoic acid, see e.g. Houben-Weyl, Methoden der Organischen Chemie, Bd. E11, p. 1299 ff., G. Thieme Verlag, Stuttgart 1985.
The carboxylic acids of formula (II) and the amides of formula (IV) can be prepared, for example, according to the procedures described in WO 04/046129 or WO 04/011447 as well as according to references cited therein and suitable modifications thereof.
After completion of the reaction, the compounds of formula I can be isolated by employing conventional methods such as adding the reaction mixture to water, extracting with an organic solvent, concentrating the extract an the like. The isolated compound (I) can be purified by a technique such as chromatography, recrystallization and the like, if necessary.
Compounds of formula A1-H can be prepared according to procedures known in the art, e.g. as described in U.S. Pat. No. 6,136,983 and references cited therein.
Compounds of formula A2-H can be prepared according to procedures known in the art, e.g. as described in WO 03/097589 and references cited therein.
Sulfoxides of formula V can be obtained according to procedures known in the art, e.g. as described in J. March, Advanced Organic Chemistry, 4th Edition, Wiley, 1992, p. 1297.
Compounds of formula I, II, III, IV, V, and compounds A1-H and A2-H which cannot be prepared according to the above procedures can be prepared according to suitable modifications of the above procedures.
The preparation of the compounds of formula I above may lead to them being obtained as isomer mixtures. If desired, these can be resolved by the methods customary for this purpose, such as crystallization or chromatography, also on optically active adsorbate, to give the pure isomers.
Agronomically acceptable salts of the compounds I can be formed in a customary manner, e.g. by reaction with an acid of the anion in question.
In this specification and in the claims, reference will be made to a number of terms that shall be defined to have the following meanings:
“Salt” as used herein includes adducts of compounds I with maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid. Moreover, included as “salts” are those that can form with, for example, amines, metals, alkaline earth metal bases or quaternary ammonium bases, including zwitterions. Suitable metal and alkaline earth metal hydroxides as salt formers include the salts of barium, aluminum, nickel, copper, manganese, cobalt zinc, iron, silver, lithium, sodium, potassium, magnesium or calcium. Additional salt formers include chloride, sulfate, acetate, carbonate, hydride, and hydroxide. Desirable salts include adducts of compounds I with maleic acid, dimaleic acid, fumaric acid, difumaric acid, and methane sulfonic acid.
“Halogen” will be taken to mean fluoro, chloro, bromo and iodo.
The term “alkyl” as used herein refers to a branched or unbranched saturated hydrocarbon group having 1 to 10 carbon atoms, such as, and preferably, C1-C6-alkyl, for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl.
The term “haloalkyl” as used herein refers to a straight-chain or branched alkyl group having 1 to 10 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example C1-C2-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
Similarly, “alkoxy” and “alkylthio” refer to straight-chain or branched alkyl groups having 1 to 10 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages, respectively, at any bond in the alkyl group. Examples include methoxy, ethoxy, propoxy, isopropoxy, methylthio, ethylthio, propylthio, isopropylthio, and n-butylthio.
Similarly, “alkylamino” refers to a nitrogen atom which carries 1 or 2 straight-chain or branched alkyl groups having 1 to 10 carbon atoms (as mentioned above) which may be the same or different. Examples include methylamino, dimethylamino, ethylamino, diethylamino, methylethylamino, isopropylamino, or methylisopropylamino.
Similarly, “alkylsulfinyl” and “alkylsulfonyl” refer to straight-chain or branched alkyl groups having 1 to 10 carbon atoms (as mentioned above) bonded through —S(═O)— or —S(═O)2-linkages, respectively, at any bond in the alkyl group. Examples include methylsulfinyl and methylsulfonyl.
The term “alkylcarbonyl” refers to straight-chain or branched alkyl groups having 1 to 10 carbon atoms (as mentioned above) bonded through a —C(═O)— linkage, respectively, at any bond in the alkyl group. Examples include acetyl, propionyl, buturyl, or 2-methylbuturyl.
The term “alkenyl” as used herein intends a branched or unbranched unsaturated hydrocarbon group having 2 to 6 carbon atoms and a double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl; 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
The term “alkynyl” as used herein refers to a branched or unbranched unsaturated hydrocarbon group containing at least one triple bond, such as ethynyl, propynyl, 1-butynyl, 2-butynyl, and the like.
A saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, is a ring system wherein two oxygen atoms must not be in adjacent positions and wherein at least 1 carbon atom must be in the ring system e.g. thiophen, furan, pyrrol, thiazol, oxazol, imidazol, isothiazol, isoxazol, pyrazol, 1,3,4-oxadiazol, 1,3,4-thiadiazol, 1,3,4-triazol, 1,2,4-oxadiazol, 1,2,4-thiadiazol, 1,2,4-triazol, 1,2,3-triazol, 1,2,3,4-tetrazol, benzo[b]thiophen, benzo[b]furan, indol, benzo[c]thiophen, benzo[c]furan, isoindol, benzoxazol, benzothiazol, benzimidazol, benzisoxazol, benzisothiazol, benzopyrazol, benzothiadiazol, benzotriazol, dibenzofuran, dibenzothiophen, carbazol, pyridin, pyrazin, pyrimidin, pyridazin, 1,3,5-triazin, 1,2,4-triazin, 1,2,4,5-tetrazin, chinolin, isochinolin, chinoxalin, chinazolin, cinnolin, 1,8-naphthyridin, 1,5-naphthyridin, 1,6-naphthyridin, 1,7-naphthyridin, phthalazin, pyridopyrimidin, purin, pteridin, 4H-chinolizin, piperidin, pyrrolidin, oxazolin, tetrahydrofuran, tetrahydropyran, isoxazolidin or thiazolidin.
A saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur also is e.g. a saturated, partially unsaturated or unsaturated 5- or 6-membered heterocycle which contains 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur, such as pyridine, pyrimidine, (1,2,4)-oxadiazole, (1,3,4)-oxadiazole, pyrrole, furan, thiophene, oxazole, thiazole, imidazole, pyrazole, isoxazole, 1,2,4-triazole, tetrazole, pyrazine, pyridazine, oxazoline, thiazoline, tetrahydrofuran, tetrahydropyran, morpholine, piperidine, piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine, oxirane or oxetane; or
a saturated, partially unsaturated or unsaturated 5- or 6-membered heterocycle which contains 1 nitrogen atom and 0 to 2 further heteroatoms selected from oxygen, nitrogen and sulfur, preferably from oxygen and nitrogen, such as piperidine, piperazin and morpholine.
Preferably, this ring system is a saturated, partially unsaturated or unsaturated 3- to 6-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein two oxygen atoms must not be in adjacent positions and wherein at least 1 carbon atom must be in the ring system.
Most preferably, this ring system is a radical of pyridine, pyrimidine, (1,2,4)-oxadiazol, 1,3,4-oxadiazol, pyrrol, furan, thiophen, oxazol, thiazol, imidazol, pyrazol, isoxazol, 1,2,4-triazol, tetrazol, pyrazin, pyridazin, oxazolin, thiazolin, tetrahydrofuran, tetrahydropyran, morpholin, piperidin, piperazin, pyrrolin, pyrrolidin, oxazolidin, thiazolidin, oxiran or oxetan.
Tri(C1-C10)alkylsilyl refers to a silicon atom having 3 straight-chain or branched C1-C10-alkyl groups as defined above which may be the same or different. Examples include trimethylsilyl, triethylsilyl, triphenylsilyl or triisopropylsilyl.
Cycloalkyl: monocyclic 3- to 6-, or 8-membered saturated carbon atom rings, e.g. C3-C8-cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl.
With respect to the intended use of the compounds of formula I, particular preference is given to the following meanings of the substituents, in each case on their own or in combination:
A compound of formula I wherein R1 is hydrogen, C1-C6-alkyl, cyano, C1-C6-alkylsulfonyl, or C2-C6-alkoxycarbonyl, preferably hydrogen or C1-C4-alkyl, most preferably hydrogen.
A compound of formula I wherein A is A1.
A compound of formula I wherein A is A2.
A compound of formula I wherein R2 and R3 each independently are R6, —C(═O)R7, —C(═NOR7)R7, —C(═NNR72)R7, —C(═O)OR7, —C(═O)NR72, —OC(═O) R7, —OC(═O)OR7, C(═O)NR7—NR72, —C(═O)NR7—NR7[C(═O)R7], or R2 and R3 together with the sulfur atom to which they are attached form a saturated, partially unsaturated or unsaturated 3- to 8-membered ring which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, which ring can be fused with one or two saturated, partially unsaturated or unsaturated 5- to 6-membered rings which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein all of the above rings are unsubstituted or substituted by any combination of 1 to 6 groups R8.
More preferably, R2 and R3 each independently are R6 or R2 and R3 together with the sulfur atom to which they are attached form a saturated, partially unsaturated or unsaturated 3- to 8-membered ring which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, which ring can be fused with one or two saturated, partially unsaturated or unsaturated 5- to 6-membered rings which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein all of the above rings are unsubstituted or substituted by any combination of 1 to 6 groups R8.
Even more preferred are compounds of formula I wherein R2 and R3 each independently are R6, preferably hydrogen, C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C3-C8-cycloalkynyl, phenyl, naphthyl, biphenyl, or a saturated, partially unsaturated or unsaturated 3- to 8-membered ring which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein all of these groups are unsubstituted or substituted by any combination of 1 to 6 groups R9.
Especially preferred are compounds of formula I wherein R2 and R3 each independently are C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C8-cycloalkyl, or phenyl, wherein these groups are unsubstituted or substituted by any combination of 1 to 6 groups selected from R10 or R11, and
R10 is C1-C10-alkyl, C3-C8-cycloalkyl, C1-C10-alkyl-C3-C8-cycloalkyl or a saturated, partially unsaturated or unsaturated 3- to 8-membered ring which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein these groups are unsubstituted or substituted with any combination of from 1 to 6 groups R11, and
R11 is halogen, cyano, nitro, hydroxy, mercapto, amino, formyl, C1-C10-alkylcarbonyl, C1-C10-alkoxy, C2-C10-alkenyloxy, C2-C10-alkynyloxy, C1-C10-haloalkoxy, C3-C8-cycloalkoxy, C3-C8-halocycloalkoxy, C1-C10-alkoxycarbonyl, C3-C8-cycloalkoxycarbonyl, C1-C10-alkylcarbonyloxy, C3-C8-cyclo alkylcarbonyloxy, C1-C10-haloalkoxycarbonyl, C1-C10-haloalkylcarbonyloxy, C1-C10-alkanamido, C3-C8-cycloalkanamido, C1-C10-alkylthio, C2-C10-alkenylthio, C2-C10-alkynylthio, C1-C10-haloalkylthio, C3-C8-cycloalkylthio, C3-C8-halocycloalkylthio, C3-C8-cycloalkyl-C1-C4-alkylthio, C1-C10-alkylsulfinyl, C2-C10-alkenylsulfinyl, C2-C10-alkynylsulfinyl, C1-C10-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C3-C8-halocycloalkenylsulfinyl, C3-C8-cycloalkyl-C1-C4-alkylsulfinyl, C1-C10-alkylsulfonyl, C2-C10-alkenylsulfonyl, C2-C10-alkynylsulfonyl, C1-C10-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-halocycloalkylsulfonyl, C3-C8-cycloalkyl-C1-C4-alkylsulfonyl, di(C1-C10-alkyl)amino, C1-C10-alkylamino, C2-C10-alkenylamino, C2-C10-alkynylamino, C1-C10-alkyl-C2-C10-alkenylamino, C1-C10-alkyl-C2-C10-alkynylamino, C1-C10-haloalkylamino, C2-C10-haloalkenylamino, C3-C8-cycloalkylamino, tri(C1-C10-alkyl)silyl, aryl, aryloxy, arylthio, arylamino, wherein aryl is phenyl, naphthyl or biphenyl, or a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein these aryl and these heterocyclic ringsystems are unsubstituted or substituted with any combination of from 1 to 6 groups selected from halogen, cyano, nitro, amino, hydroxy, mercapto, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, di(C1-C4-alkyl) amino and C1-C4-alkylamino.
More preferred are compounds of formula I wherein R2 and R3 each independently are C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C8-cycloalkyl, or phenyl, wherein these groups are unsubstituted or substituted by any combination of 1 to 6 groups selected from R11, and
R11 is halogen, cyano, nitro, hydroxy, mercapto, amino, C1-C10-alkoxy, C1-C10-haloalkoxy, C3-C8-cycloalkoxy, C1-C10-alkoxycarbonyl, C1-C10-alkylcarbonyloxy, C1-C10-alkanamido, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, di(C1-C10-alkyl)amino or C1-C10-alkylamino.
Preferred are also compounds of formula I wherein R2 and R3 together with the sulfur atom to which they are attached form a 5- or 6-membered heterocycle which besides the sulfur atom contains 1 nitrogen or 1 oxygen atom, wherein these groups are unsubstituted or substituted by any combination of 1 to 6 groups selected from with any combination of from 1 to 6 groups selected from halogen, cyano, nitro, amino, hydroxy, mercapto, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, di(C1-C4-alkyl) amino and C1-C4-alkylamino.
Preferred are also compounds of formula I wherein R2 and R3 together with the sulfur atom to which they are attached form a unit SR2R3 of the following formula:
wherein
- r is 0 or 1;
- D is a direct bond, branched or straight C1-C4-alkylene, O, S(O)0,1,2 or NRj, preferably CH2, O, or NRj;
- R9 is as defined above for compounds of formula I;
- Rj is hydrogen, C1-C4-alkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, or C1-C4-alkylsulfonyl;
- a,b are the same or different 0, 1, 2, 3 or 4, preferably 0, 1, or 2.
When r=0 then the both aryl groups are unbridged.
Preferred are compounds of formula I wherein R9 is R10, R11, or —C(═O)R10, —C(═NOR10)R10, —C(═NNR102)R10, —C(═O)OR10, —C(═O)NR102, —C(═O)NR10—NR102, —C(═O)NR10—NR10[C(═O)R10], —SO2NR102, —OR10, —NR102, or —SR10.
Preferred are compounds of formula I wherein R4 is NR12R13 and
R12 and R13 are each independently hydrogen, C1-C20-alkyl, C2-C20-alkenyl or C2-C20-alkynyl, each of which is unsubstituted or substituted by from 1 to 6 groups selected from C1-C4-alkoxy, C1-C4-alkylthio, CN, NO2, formyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C3-C8-cycloalkyl, and phenyl, wherein phenyl itself is unsubstituted or substituted by 1 to 4 substituents selected from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-fluoroalkyl, C1-C4-alkyloxycarbonyl, trifluoromethylsulfonyl, formyl, nitro and cyano; or
C1-C20-haloalkyl, C2-C20-haloalkenyl, C2-C20-haloalkynyl, C5-C10-cycloalkenyl, or a saturated or partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein this ring system is unsubstituted or substituted by 1 to 4 substituents selected from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-fluoroalkyl, C1-C4-alkyloxycarbonyl, trifluoromethylsulfonyl, formyl, nitro and cyano; or
R12 and R13 together with the nitrogen atom to which they are attached may also form a saturated or partially unsaturated 5- to 8-membered heterocycle which besides the one nitrogen atom contains 0 to 2 further heteroatoms selected from oxygen, nitrogen, sulfur and may contain 1 or 2 carbonyl groups or thiocarbonyl groups and which is unsubstituted or substituted by from 1 to 4 groups selected from C1-C4-alkyl, C1-C4-alkoxy and C1-C4-haloalkyl.
More preferred are compounds of formula I wherein R4 is NR12R13 and
R12 and R13 are each independently hydrogen, C1-C20-alkyl, C2-C20-alkenyl or C2-C20-alkynyl, each of which is unsubstituted or substituted by from 1 to 3 CN, C1-C20-haloalkyl, or R12 and R13 together with the nitrogen atom to which they are attached may also form a saturated or partially unsaturated 5- to 8-membered heterocycle which besides the one nitrogen atom contains 0 to 2 further heteroatoms selected from oxygen, nitrogen, sulfur, and may contain 1 or 2 carbonyl groups or thiocarbonyl groups and which is unsubstituted or substituted by from 1 to 4 groups selected from C1-C4-alkyl, C1-C4-alkoxy and C1-C4-haloalkyl.
Especially preferred are compounds of formula I wherein R4 is NR12R13 and R12 and R13 together with the nitrogen atom to which they are attached are a saturated or partially unsaturated 5- or 6-membered nitrogen heterocycle which may be substituted by from 1 to 4 groups selected from C1-C4-alkyl, C1-C4-alkoxy and C1-C4-haloalkyl, in particular 2,5-dihydropyrrol-1-yl, 2,3-dihydropyrrol-1-yl, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 2-methylmorpholin-4-yl, 2,6-dimethylmorpholin-4-yl, or 1-methylpiperazin-4-yl.
Preferred are compounds of formula I wherein R5 is hydrogen.
Preferred are compounds of formula I wherein Q1 is hydrogen, halogen, cyano, SCN, nitro, hydroxy, C1-C10-alkyl, C1-C10-haloalkyl, C3-C8-cycloalkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfonyl, C1-C10-alkylsulfonyloxy, C1-C10-alkylamino or di(C1-C10-alkyl)amino, most preferably hydrogen, halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl.
Preferred are compounds of formula I wherein Q2 is halogen, cyano, SCN, nitro, hydroxy, C1-C10-alkyl, C1-C10-haloalkyl, C3-C8-cycloalkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfonyl, C1-C10-alkylsulfonyloxy, C1-C10-alkylamino or di(C1-C10-alkyl)amino, most preferably halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl.
Preferred are compounds of formula I wherein Q3 is halogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, each unsubstituted or independently substituted with 1 to 2 groups selected from cyano, C1-C10-alkoxy, C1-C10-haloalkoxy or C1-C10-alkylthio, or
Q3 is OR14, S(O)qR14, NR15R16, OS(O)2R17, C(S)NH2, C(R18)═NOR18; and
R14 is C1-C10-alkyl or C3-C8-cycloalkyl unsubstituted or substituted with 1 R19; and
R15 is C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, each unsubstituted or substituted with 1 R19; and
R16 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, each unsubstituted or substituted with 1 R19; and
R17 is C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C8-cycloalkyl, each unsubstituted or substituted with 1 R19; and
R18 is hydrogen, C1-C10-alkyl, or C1-C10-haloalkyl; and
R19 is cyano, nitro, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, or C1-C10-haloalkylthio.
Most preferred are compounds of formula I wherein Q3 is halogen, C1-C4-haloalkyl or C1-C4-haloalkoxy.
Preferred are compounds of formula I wherein Q4 is halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, or C1-C10-alkoxycarbonyl, preferably halogen or C1-C4-haloalkyl.
Preferred are compounds of formula I wherein X and Y are oxygen.
Preferred are compounds of formula I wherein W is N or CQ4, preferably N.
Preferred are compounds of formula I wherein m is 2.
Preferred are compounds of formula I wherein n is 0.
Preferred are compounds of formula I wherein V and V′ each independently are N or CH. Preferably, both V and V′ are CH.
Especially preferred are N-thio-anthranilamid compounds of formula I wherein
W is N;R1 is hydrogen;
Q1 is hydrogen, halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl;
Q2 is halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl;
Q3 is halogen, C1-C4-haloalkyl or C1-C4-haloalkoxy;
Q4 is halogen or C1-C4-haloalkyl and is in the ortho-position; and
p is 1.
Also, especially preferred are N-thio-anthranilamid compounds of formula I wherein
- A is A2;
- R4 is C1-C6-alkylamino, C2-C6-alkenylamino, C2-C6-alkynylamino, di(C1-C6-alkyl)amino, di(C2-C6-alkenyl)amino, di(C2-C6-alkynyl)amino, (phenyl)(C1-C6-alkyl)amino, (phenyl)(C2-C6-alkenyl)amino, (phenyl)(C2-C6-alkynyl)amino, piperidine, piperazin or morpholine; and
- R5 is hydrogen or C1-C4-alkyl.
Also, especially preferred are N-thio-anthranilamid compounds of formula I wherein
- A is A1; and
- R2 and R3 each independently are phenyl, C1-C6-alkyl, C2-C6-alkenyl, or C2-C6-alkynyl, which are unsubstituted or substituted with any combination of 1 to 6 groups selected from halogen and cyano.
Most preferred are compounds of formula I wherein R2 and R3 each independently are C1-C4-alkyl, phenylmethyl, allylmethyl, propargylmethyl, or together with the sulfur atom to which they are attached form a 3- to 6-membered saturated ring which contains 1 to 3 heteroatoms selected from sulfur and oxygen.
With respect to their use, particular preference is given to the compounds IA compiled in the tables below. Moreover, the groups mentioned for a substituent in the tables are on their own, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituent in question.
Table 1Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CF3, and A in each case corresponds to a row of Table A.
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes bromine, and A in each case corresponds to a row of Table A.
Table 3Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes chlorine, and A in each case corresponds to a row of Table A.
Table 4Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH3, and A in each case corresponds to a row of Table A.
Table 5 Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH3, and A in each case corresponds to a row of Table A.
Table 6Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table A.
Table 7Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes ethoxy, and A in each case corresponds to a row of Table A.
Table 8Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table A.
Table 9Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table A.
Table 10Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table A.
Table 11Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table A.
Table 12Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table A.
Table 13Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table A.
Table 14Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table A.
Table 15Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table A.
Table 16Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table A.
Table 17Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table A.
Table 18Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 19Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table A.
Table 20Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 21Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table A.
Table 22Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table A.
Table 23Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table A.
Table 24Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table A.
Table 25Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table A.
Table 26Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table A.
Table 27Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table A.
Table 28Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table A.
Table 29Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table A.
Table 30Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table A.
Table 31Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table A.
Table 32Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table A.
Table 33Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table A.
Table 34Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table A.
Table 35Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table A.
Table 36Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 37Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table A.
Table 38Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 39Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table A.
Table 40Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 41Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table A.
Table 42Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 43Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CF3, and A in each case corresponds to a row of Table A.
Table 44Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes bromine, and A in each case corresponds to a row of Table A.
Table 45Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes chlorine, and A in each case corresponds to a row of Table A.
Table 46Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH3, and A in each case corresponds to a row of Table A.
Table 47Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH3, and A in each case corresponds to a row of Table A.
Table 48Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table A.
Table 49Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes ethoxy, and A in each case corresponds to a row of Table A.
Table 50Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table A.
Table 51Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table A.
Table 52Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table A.
Table 53Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table A.
Table 54Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table A.
Table 55Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table A.
Table 56Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table A.
Table 57Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table A.
Table 58Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table A.
Table 59Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table A.
Table 60Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 61Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table A.
Table 62Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 63Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table A.
Table 64Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table A.
Table 65Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table A.
Table 66Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table A.
Table 67Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table A.
Table 68Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table A.
Table 69Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table A.
Table 70Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table A.
Table 71Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table A.
Table 72Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table A.
Table 73Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table A.
Table 74Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table A.
Table 75Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table A.
Table 76Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table A.
Table 77Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table A.
Table 78Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 79Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table A.
Table 80Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 81Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table A.
Table 82Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 83Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table A.
Table 84Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 85Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CF3, and A in each case corresponds to a row of Table A.
Table 86Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes bromine, and A in each case corresponds to a row of Table A.
Table 87Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes chlorine, and A in each case corresponds to a row of Table A.
Table 88Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH3, and A in each case corresponds to a row of Table A.
Table 89Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH3, and A in each case corresponds to a row of Table A.
Table 90Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table A.
Table 91Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes ethoxy, and A in each case corresponds to a row of Table A.
Table 92Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table A.
Table 93Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table A.
Table 94Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table A.
Table 95Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table A.
Table 96Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table A.
Table 97Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table A.
Table 98Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table A.
Table 99Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table A.
Table 100Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table A.
Table 101Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table A.
Table 102Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 103Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table A.
Table 104Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 105Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table A.
Table 106Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table A.
Table 107Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table A.
Table 108Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table A.
Table 109Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table A.
Table 110Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table A.
Table 111Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table A.
Table 112Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table A.
Table 113Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table A.
Table 114Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table A.
Table 115Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table A.
Table 116Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table A.
Table 117Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table A.
Table 118Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table A.
Table 119Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table A.
Table 120Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 121Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table A.
Table 122Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 123Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table A.
Table 124Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 125Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table A.
Table 126Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 127Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CF3, and A in each case corresponds to a row of Table A.
Table 128Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes bromine, and A in each case corresponds to a row of Table A.
Table 129Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes chlorine, and A in each case corresponds to a row of Table A.
Table 130Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH3, and A in each case corresponds to a row of Table A.
Table 131Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH3, and A in each case corresponds to a row of Table A.
Table 132Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table A.
Table 133Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes ethoxy, and A in each case corresponds to a row of Table A.
Table 134Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table A.
Table 135Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table A.
Table 136Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table A.
Table 137Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table A.
Table 138Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table A.
Table 139Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table A.
Table 140Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table A.
Table 141Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table A.
Table 142Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table A.
Table 143Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table A.
Table 144Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 145Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table A.
Table 146Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 147Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table A.
Table 148Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table A.
Table 149Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table A.
Table 150Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table A.
Table 151Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table A.
Table 152Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table A.
Table 153Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table A.
Table 154Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table A.
Table 155Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table A.
Table 156Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table A.
Table 157Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table A.
Table 158Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table A.
Table 159Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table A.
Table 160Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table A.
Table 161Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table A.
Table 162Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 163Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table A.
Table 164Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 165Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table A.
Table 166Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 167Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table A.
Table 168Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 169Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CF3, and A in each case corresponds to a row of Table A.
Table 170Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes bromine, and A in each case corresponds to a row of Table A.
Table 171Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes chlorine, and A in each case corresponds to a row of Table A.
Table 172Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH3, and A in each case corresponds to a row of Table A.
Table 173Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH3, and A in each case corresponds to a row of Table A.
Table 174Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table A.
Table 175Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes ethoxy, and A in each case corresponds to a row of Table A.
Table 176Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table A.
Table 177Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table A.
Table 178Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table A.
Table 179Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table A.
Table 180Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table A.
Table 181Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table A.
Table 182Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table A.
Table 183Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table A.
Table 184Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table A.
Table 185Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table A.
Table 186Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 187Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table A.
Table 188Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 189Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table A.
Table 190Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table A.
Table 191Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table A.
Table 192Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table A.
Table 193Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table A.
Table 194Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table A.
Table 195Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table A.
Table 196Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table A.
Table 197Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table A.
Table 198Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table A.
Table 199Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table A.
Table 200Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table A.
Table 201Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table A.
Table 202Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table A.
Table 203Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table A.
Table 204Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 205Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table A.
Table 206Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 207Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table A.
Table 208Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 209Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table A.
Table 210Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 211Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CF3, and A in each case corresponds to a row of Table A.
Table 212Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes bromine, and A in each case corresponds to a row of Table A.
Table 213Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes chlorine, and A in each case corresponds to a row of Table A.
Table 214Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH3, and A in each case corresponds to a row of Table A.
Table 215Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH3, and A in each case corresponds to a row of Table A.
Table 216Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table A.
Table 217Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes ethoxy, and A in each case corresponds to a row of Table A.
Table 218Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table A.
Table 219Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table A.
Table 220Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table A.
Table 221Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table A.
Table 222Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table A.
Table 223Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table A.
Table 224Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table A.
Table 225Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table A.
Table 226Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table A.
Table 227Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table A.
Table 228Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 229Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table A.
Table 230Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 231Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table A.
Table 232Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table A.
Table 233Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table A.
Table 234Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table A.
Table 235Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table A.
Table 236Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table A.
Table 237Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table A.
Table 238Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table A.
Table 239Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table A.
Table 240Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table A.
Table 241Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table A.
Table 242Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table A.
Table 243Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table A.
Table 244Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table A.
Table 245Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table A.
Table 246Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 247Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table A.
Table 248Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 249Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table A.
Table 250Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 251Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table A.
Table 252Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 253Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CF3, and A in each case corresponds to a row of Table A.
Table 254Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes bromine, and A in each case corresponds to a row of Table A.
Table 255Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes chlorine, and A in each case corresponds to a row of Table A.
Table 256Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH3, and A in each case corresponds to a row of Table A.
Table 257Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH3, and A in each case corresponds to a row of Table A.
Table 258Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table A.
Table 259Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes ethoxy, and A in each case corresponds to a row of Table A.
Table 260Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table A.
Table 261Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table A.
Table 262Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table A.
Table 263Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table A.
Table 264Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table A.
Table 265Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table A.
Table 266Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table A.
Table 267Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table A.
Table 268Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table A.
Table 269Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table A.
Table 270Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 271Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table A.
Table 272Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 273Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table A.
Table 274Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table A.
Table 275Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table A.
Table 276Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table A.
Table 277Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table A.
Table 278Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table A.
Table 279Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table A.
Table 280Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table A.
Table 281Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table A.
Table 282Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table A.
Table 283Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table A.
Table 284Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table A.
Table 285Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table A.
Table 286Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table A.
Table 287Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table A.
Table 288Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 289Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table A.
Table 290Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 291Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table A.
Table 292Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 293Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table A.
Table 294Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table A.
Compounds of the formula IA (as defined above) wherein Q1 denotes hydrogen, Q3 denotes CF3, and A in each case corresponds to a row of Table B.
Table 296Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes bromine, and A in each case corresponds to a row of Table B.
Table 297Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes chlorine, and A in each case corresponds to a row of Table B.
Table 298Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH3, and A in each case corresponds to a row of Table B.
Table 299Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH3, and A in each case corresponds to a row of Table B.
Table 300Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table B.
Table 301Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes ethoxy, and A in each case corresponds to a row of Table B.
Table 302Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table B.
Table 303Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table B.
Table 304Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table B.
Table 305Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table B.
Table 306Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table B.
Table 307Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table B.
Table 308Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table B.
Table 309Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table B.
Table 310Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table B.
Table 311Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table B.
Table 312Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 313Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table B.
Table 314Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 315Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table B.
Table 316Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table B.
Table 317Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table B.
Table 318Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table B.
Table 319Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table B.
Table 320Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table B.
Table 321Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table B.
Table 322Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table B.
Table 323Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table B.
Table 324Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table B.
Table 325Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table B.
Table 326Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table B.
Table 327Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table B.
Table 328Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table B.
Table 329Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table B.
Table 330Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 331Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table B.
Table 332Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 333Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table B.
Table 334Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 335Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table B.
Table 336Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 337Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CF3, and A in each case corresponds to a row of Table B.
Table 338Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes bromine, and A in each case corresponds to a row of Table B.
Table 339Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes chlorine, and A in each case corresponds to a row of Table B.
Table 340Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH3, and A in each case corresponds to a row of Table B.
Table 341Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH3, and A in each case corresponds to a row of Table B.
Table 342Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table B.
Table 343Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes ethoxy, and A in each case corresponds to a row of Table B.
Table 344Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table B.
Table 345Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table B.
Table 346Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table B.
Table 347Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table B.
Table 348Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table B.
Table 349Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table B.
Table 350Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table B.
Table 351Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table B.
Table 352Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table B.
Table 353Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table B.
Table 354Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 355Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table B.
Table 356Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 357Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table B.
Table 358Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table B.
Table 359Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table B.
Table 360Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table B.
Table 361Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table B.
Table 362Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table B.
Table 363Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table B.
Table 364Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table B.
Table 365Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table B.
Table 366Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table B.
Table 367Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table B.
Table 368Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table B.
Table 369Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table B.
Table 370Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table B.
Table 371Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table B.
Table 372Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 373Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table B.
Table 374Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 375Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table B.
Table 376Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 377Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table B.
Table 378Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 379Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CF3, and A in each case corresponds to a row of Table B.
Table 380Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes bromine, and A in each case corresponds to a row of Table B.
Table 381Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes chlorine, and A in each case corresponds to a row of Table B.
Table 382Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH3, and A in each case corresponds to a row of Table B.
Table 383Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH3, and A in each case corresponds to a row of Table B.
Table 384Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table B.
Table 385Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes ethoxy, and A in each case corresponds to a row of Table B.
Table 386Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table B.
Table 387Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table B.
Table 388Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table B.
Table 389Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table B.
Table 390Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table B.
Table 391Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table B.
Table 392Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table B.
Table 393Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table B.
Table 394Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table B.
Table 395Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table B.
Table 396Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 397Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table B.
Table 398Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 399Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table B.
Table 400Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table B.
Table 401Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table B.
Table 402Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table B.
Table 403Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table B.
Table 404Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table B.
Table 405Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table B.
Table 406Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table B.
Table 407Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table B.
Table 408Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table B.
Table 409Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table B.
Table 410Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table B.
Table 411Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table B.
Table 412Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table B.
Table 413Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table B.
Table 414Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 415Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table B.
Table 416Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 417Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table B.
Table 418Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 419Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table B.
Table 420Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 421Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CF3, and A in each case corresponds to a row of Table B.
Table 422Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes bromine, and A in each case corresponds to a row of Table B.
Table 423Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes chlorine, and A in each case corresponds to a row of Table B.
Table 424Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH3, and A in each case corresponds to a row of Table B.
Table 425Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH3, and A in each case corresponds to a row of Table B.
Table 426Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table B.
Table 427Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes ethoxy, and A in each case corresponds to a row of Table B.
Table 428Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table B.
Table 429Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table B.
Table 430Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table B.
Table 431Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table B.
Table 432Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table B.
Table 433Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table B.
Table 434Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table B.
Table 435Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table B.
Table 436Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table B.
Table 437Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table B.
Table 438Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 439Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table B.
Table 440Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 441Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table B.
Table 442Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table B.
Table 443Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table B.
Table 444Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table B.
Table 445Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table B.
Table 446Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table B.
Table 447Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table B.
Table 448Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table B.
Table 449Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table B.
Table 450Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table B.
Table 451Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table B.
Table 452Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table B.
Table 453Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table B.
Table 454Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table B.
Table 455Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table B.
Table 456Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 457Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table B.
Table 458Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 459Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table B.
Table 460Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 461Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table B.
Table 462Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 463Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CF3, and A in each case corresponds to a row of Table B.
Table 464Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes bromine, and A in each case corresponds to a row of Table B.
Table 465Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes chlorine, and A in each case corresponds to a row of Table B.
Table 466Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH3, and A in each case corresponds to a row of Table B.
Table 467Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH3, and A in each case corresponds to a row of Table B.
Table 468Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table B.
Table 469Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes ethoxy, and A in each case corresponds to a row of Table B.
Table 470Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table B.
Table 471Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table B.
Table 472Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table B.
Table 473Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table B.
Table 474Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table B.
Table 475Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table B.
Table 476Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table B.
Table 477Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table B.
Table 478Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table B.
Table 479Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table B.
Table 480Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 481Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table B.
Table 482Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 483Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table B.
Table 484Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table B.
Table 485Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table B.
Table 486Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table B.
Table 487Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table B.
Table 488Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table B.
Table 489Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table B.
Table 490Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table B.
Table 491Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table B.
Table 492Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table B.
Table 493Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table B.
Table 494Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table B.
Table 495Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table B.
Table 496Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table B.
Table 497Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table B.
Table 498Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 499Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table B.
Table 500Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 501Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table B.
Table 502Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 503Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table B.
Table 504Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 505Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CF3, and A in each case corresponds to a row of Table B.
Table 506Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes bromine, and A in each case corresponds to a row of Table B.
Table 507Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes chlorine, and A in each case corresponds to a row of Table B.
Table 508Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH3, and A in each case corresponds to a row of Table B.
Table 509Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH3, and A in each case corresponds to a row of Table B.
Table 510Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table B.
Table 511Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes ethoxy, and A in each case corresponds to a row of Table B.
Table 512Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table B.
Table 513Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table B.
Table 514Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table B.
Table 515Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table B.
Table 516Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table B.
Table 517Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table B.
Table 518Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table B.
Table 519Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table B.
Table 520Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table B.
Table 521Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table B.
Table 522Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 523Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table B.
Table 524Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 525Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table B.
Table 526Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table B.
Table 527Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table B.
Table 528Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table B.
Table 529Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table B.
Table 530Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table B.
Table 531Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table B.
Table 532Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table B.
Table 533Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table B.
Table 534Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table B.
Table 535Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table B.
Table 536Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table B.
Table 537Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table B.
Table 538Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table B.
Table 539Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table B.
Table 540Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 541Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table B.
Table 542Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 543Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table B.
Table 544Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 545Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table B.
Table 546Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 547Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CF3, and A in each case corresponds to a row of Table B.
Table 548Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes bromine, and A in each case corresponds to a row of Table B.
Table 549Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes chlorine, and A in each case corresponds to a row of Table B.
Table 550Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH3, and A in each case corresponds to a row of Table B.
Table 551Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH3, and A in each case corresponds to a row of Table B.
Table 552Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table B.
Table 553Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes ethoxy, and A in each case corresponds to a row of Table B.
Table 554Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table B.
Table 555Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table B.
Table 556Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table B.
Table 557Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table B.
Table 558Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table B.
Table 559Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table B.
Table 560Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table B.
Table 561Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table B.
Table 562Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table B.
Table 563Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table B.
Table 564Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 565Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table B.
Table 566Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 567Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table B.
Table 568Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table B.
Table 569Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table B.
Table 570Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table B.
Table 571Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table B.
Table 572Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table B.
Table 573Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table B.
Table 574Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table B.
Table 575Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table B.
Table 576Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table B.
Table 577Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table B.
Table 578Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table B.
Table 579Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table B.
Table 580Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table B.
Table 581Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table B.
Table 582Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 583Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table B.
Table 584Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 585Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table B.
Table 586Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 587Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table B.
Table 588Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table B.
Compounds of the formula IA (as defined above) wherein Q1 denotes hydrogen, Q3 denotes CF3, and A in each case corresponds to a row of Table C.
Table 590Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes bromine, and A in each case corresponds to a row of Table C.
Table 591Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes chlorine, and A in each case corresponds to a row of Table C.
Table 592Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH3, and A in each case corresponds to a row of Table C.
Table 593Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH3, and A in each case corresponds to a row of Table C.
Table 594Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table C.
Table 595Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes ethoxy, and A in each case corresponds to a row of Table C.
Table 596Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table C.
Table 597Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table C.
Table 598Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table C.
Table 599Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table C.
Table 600Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table C.
Table 601Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table C.
Table 602Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table C.
Table 603Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table C.
Table 604Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table C.
Table 605Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table C.
Table 606Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 607Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table C.
Table 608Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 609Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table C.
Table 610Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table C.
Table 611Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table C.
Table 612Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table C.
Table 613Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table C.
Table 614Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table C.
Table 615Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table C.
Table 616Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table C.
Table 617Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table C.
Table 618Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table C.
Table 619Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table C.
Table 620Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table C.
Table 621Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table C.
Table 622Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table C.
Table 623Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table C.
Table 624Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 625Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table C.
Table 626Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 627Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table C.
Table 628Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 629Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table C.
Table 630Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 631Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CF3, and A in each case corresponds to a row of Table C.
Table 632Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes bromine, and A in each case corresponds to a row of Table C.
Table 633Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes chlorine, and A in each case corresponds to a row of Table C.
Table 634Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH3, and A in each case corresponds to a row of Table C.
Table 635Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH3, and A in each case corresponds to a row of Table C.
Table 636Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table C.
Table 637Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes ethoxy, and A in each case corresponds to a row of Table C.
Table 638Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table C.
Table 639Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table C.
Table 640Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table C.
Table 641Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table C.
Table 642Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table C.
Table 643Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table C.
Table 644Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table C.
Table 645Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table C.
Table 646Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table C.
Table 647Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table C.
Table 648Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 649Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table C.
Table 650Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 651Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table C.
Table 652Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table C.
Table 653Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table C.
Table 654Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table C.
Table 655Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table C.
Table 656Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table C.
Table 657Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table C.
Table 658Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table C.
Table 659Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table C.
Table 660Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table C.
Table 661Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table C.
Table 662Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table C.
Table 663Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table C.
Table 664Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table C.
Table 665Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table C.
Table 666Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 667Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table C.
Table 668Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 669Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table C.
Table 670Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 671Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table C.
Table 672Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 673Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CF3, and A in each case corresponds to a row of Table C.
Table 674Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes bromine, and A in each case corresponds to a row of Table C.
Table 675Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes chlorine, and A in each case corresponds to a row of Table C.
Table 676Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH3, and A in each case corresponds to a row of Table C.
Table 677Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH3, and A in each case corresponds to a row of Table C.
Table 678Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table C.
Table 679Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes ethoxy, and A in each case corresponds to a row of Table C.
Table 680Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table C.
Table 681Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table C.
Table 682Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table C.
Table 683Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table C.
Table 684Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table C.
Table 685Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table C.
Table 686Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table C.
Table 687Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table C.
Table 688Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table C.
Table 689Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table C.
Table 690Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 691Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table C.
Table 692Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 693Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table C.
Table 694Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table C.
Table 695Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table C.
Table 696Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table C.
Table 697Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table C.
Table 698Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table C.
Table 699Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table C.
Table 700Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table C.
Table 701Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table C.
Table 702Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table C.
Table 703Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table C.
Table 704Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table C.
Table 705Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table C.
Table 706Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table C.
Table 707Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table C.
Table 708Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 709Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table C.
Table 710Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 711Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table C.
Table 712Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 713Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table C.
Table 714Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 715Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CF3, and A in each case corresponds to a row of Table C.
Table 716Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes bromine, and A in each case corresponds to a row of Table C.
Table 717Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes chlorine, and A in each case corresponds to a row of Table C.
Table 718Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH3, and A in each case corresponds to a row of Table C.
Table 719Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH3, and A in each case corresponds to a row of Table C.
Table 720Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table C.
Table 721Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes ethoxy, and A in each case corresponds to a row of Table C.
Table 722Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table C.
Table 723Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table C.
Table 724Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table C.
Table 725Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table C.
Table 726Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table C.
Table 727Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table C.
Table 728Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table C.
Table 729Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table C.
Table 730Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table C.
Table 731Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table C.
Table 732Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 733Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table C.
Table 734Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 735Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table C.
Table 736Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table C.
Table 737Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table C.
Table 738Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table C.
Table 739Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table C.
Table 740Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table C.
Table 741Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table C.
Table 742Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table C.
Table 743Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table C.
Table 744Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table C.
Table 745Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table C.
Table 746Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table C.
Table 747Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table C.
Table 748Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table C.
Table 749Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table C.
Table 750Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 751Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table C.
Table 752Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 753Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table C.
Table 754Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 755Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table C.
Table 756Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 757Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CF3, and A in each case corresponds to a row of Table C.
Table 758Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes bromine, and A in each case corresponds to a row of Table C.
Table 759Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes chlorine, and A in each case corresponds to a row of Table C.
Table 760Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH3, and A in each case corresponds to a row of Table C.
Table 761Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH3, and A in each case corresponds to a row of Table C.
Table 762Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table C.
Table 763Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes ethoxy, and A in each case corresponds to a row of Table C.
Table 764Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table C.
Table 765Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table C.
Table 766Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table C.
Table 767Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table C.
Table 768Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table C.
Table 769Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table C.
Table 770Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table C.
Table 771Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table C.
Table 772Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table C.
Table 773Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table C.
Table 774Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 775Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table C.
Table 776Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 777Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table C.
Table 778Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table C.
Table 779Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table C.
Table 780Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table C.
Table 781Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table C.
Table 782Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table C.
Table 783Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table C.
Table 784Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table C.
Table 785Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table C.
Table 786Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table C.
Table 787Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table C.
Table 788Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table C.
Table 789Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table C.
Table 790Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table C.
Table 791Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table C.
Table 792Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 793Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table C.
Table 794Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 795Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table C.
Table 796Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 797Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table C.
Table 798Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 799Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CF3, and A in each case corresponds to a row of Table C.
Table 800Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes bromine, and A in each case corresponds to a row of Table C.
Table 801Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes chlorine, and A in each case corresponds to a row of Table C.
Table 802Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH3, and A in each case corresponds to a row of Table C.
Table 803Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH3, and A in each case corresponds to a row of Table C.
Table 804Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table C.
Table 805Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes ethoxy, and A in each case corresponds to a row of Table C.
Table 806Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table C.
Table 807Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table C.
Table 808Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table C.
Table 809Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table C.
Table 810Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table C.
Table 811Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table C.
Table 812Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table C.
Table 813Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table C.
Table 814Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table C.
Table 815Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table C.
Table 816Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 817Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table C.
Table 818Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 819Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table C.
Table 820Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table C.
Table 821Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table C.
Table 822Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table C.
Table 823Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table C.
Table 824Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table C.
Table 825Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table C.
Table 826Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table C.
Table 827Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table C.
Table 828Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table C.
Table 829Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table C.
Table 830Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table C.
Table 831Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table C.
Table 832Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table C.
Table 833Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table C.
Table 834Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 835Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table C.
Table 836Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 837Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table C.
Table 838Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 839Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table C.
Table 840Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 841Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CF3, and A in each case corresponds to a row of Table C.
Table 842Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes bromine, and A in each case corresponds to a row of Table C.
Table 843Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes chlorine, and A in each case corresponds to a row of Table C.
Table 844Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH3, and A in each case corresponds to a row of Table C.
Table 845Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH3, and A in each case corresponds to a row of Table C.
Table 846Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCHCH2, and A in each case corresponds to a row of Table C.
Table 847Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes ethoxy, and A in each case corresponds to a row of Table C.
Table 848Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a row of Table C.
Table 849Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a row of Table C.
Table 850Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CCH, and A in each case corresponds to a row of Table C.
Table 851Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCH3, and A in each case corresponds to a row of Table C.
Table 852Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a row of Table C.
Table 853Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2SCH3, and A in each case corresponds to a row of Table C.
Table 854Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a row of Table C.
Table 855Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a row of Table C.
Table 856Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a row of Table C.
Table 857Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a row of Table C.
Table 858Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 859Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a row of Table C.
Table 860Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 861Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a row of Table C.
Table 862Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a row of Table C.
Table 863Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OC(═O)CF3, and A in each case corresponds to a row of Table C.
Table 864Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHCH2CF3, and A in each case corresponds to a row of Table C.
Table 865Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a row of Table C.
Table 866Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a row of Table C.
Table 867Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a row of Table C.
Table 868Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a row of Table C.
Table 869Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a row of Table C.
Table 870Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CN, and A in each case corresponds to a row of Table C.
Table 871Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2NO2, and A in each case corresponds to a row of Table C.
Table 872Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes cyclopropyloxy, and A in each case corresponds to a row of Table C.
Table 873Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCHF2, and A in each case corresponds to a row of Table C.
Table 874Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a row of Table C.
Table 875Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOCH3, and A in each case corresponds to a row of Table C.
Table 876Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 877Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a row of Table C.
Table 878Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 879Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a row of Table C.
Table 880Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 881Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a row of Table C.
Table 882Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a row of Table C.
Compounds of the formula IA (as defined above) wherein Q1 denotes hydrogen, Q3 denotes CF3, and A in each case corresponds to a radical of Table D.
Table 884Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes bromine, and A in each case corresponds to a radical of Table D.
Table 885Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes chlorine, and A in each case corresponds to a radical of Table D.
Table 886Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH3, and A in each case corresponds to a radical of Table D.
Table 887Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH3, and A in each case corresponds to a radical of Table D.
Table 888Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCHCH2, and A in each case corresponds to a radical of Table D.
Table 889Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes ethoxy, and A in each case corresponds to a radical of Table D.
Table 890Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a radical of Table D.
Table 891Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a radical of Table D.
Table 892Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CCH, and A in each case corresponds to a radical of Table D.
Table 893Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCH3, and A in each case corresponds to a radical of Table D.
Table 894Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a radical of Table D.
Table 895Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2SCH3, and A in each case corresponds to a radical of Table D.
Table 896Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a radical of Table D.
Table 897Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a radical of Table D.
Table 898Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a radical of Table D.
Table 899Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a radical of Table D.
Table 900Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 901Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a radical of Table D.
Table 902Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 903Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a radical of Table D.
Table 904Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a radical of Table D.
Table 905Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OC(═O)CF3, and A in each case corresponds to a radical of Table D.
Table 906Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHCH2CF3, and A in each case corresponds to a radical of Table D.
Table 907Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a radical of Table D.
Table 908Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a radical of Table D.
Table 909Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a radical of Table D.
Table 910Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a radical of Table D.
Table 911Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a radical of Table D.
Table 912Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CN, and A in each case corresponds to a radical of Table D.
Table 913Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2NO2, and A in each case corresponds to a radical of Table D.
Table 914Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes cyclopropyloxy, and A in each case corresponds to a radical of Table D.
Table 915Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCHF2, and A in each case corresponds to a radical of Table D.
Table 916Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a radical of Table D.
Table 917Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOCH3, and A in each case corresponds to a radical of Table D.
Table 918Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 919Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a radical of Table D.
Table 920Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 921Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a radical of Table D.
Table 922Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 923Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a radical of Table D.
Table 924Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 925Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CF3, and A in each case corresponds to a radical of Table D.
Table 926Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes bromine, and A in each case corresponds to a radical of Table D.
Table 927Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes chlorine, and A in each case corresponds to a radical of Table D.
Table 928Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH3, and A in each case corresponds to a radical of Table D.
Table 929Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH3, and A in each case corresponds to a radical of Table D.
Table 930Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCHCH2, and A in each case corresponds to a radical of Table D.
Table 931Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes ethoxy, and A in each case corresponds to a radical of Table D.
Table 932Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a radical of Table D.
Table 933Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a radical of Table D.
Table 934Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CCH, and A in each case corresponds to a radical of Table D.
Table 935Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCH3, and A in each case corresponds to a radical of Table D.
Table 936Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a radical of Table D.
Table 937Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2SCH3, and A in each case corresponds to a radical of Table D.
Table 938Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a radical of Table D.
Table 939Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a radical of Table D.
Table 940Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a radical of Table D.
Table 941Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a radical of Table D.
Table 942Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 943Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a radical of Table D.
Table 944Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 945Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a radical of Table D.
Table 946Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a radical of Table D.
Table 947Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a radical of Table D.
Table 948Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHCH2CF3, and A in each case corresponds to a radical of Table D.
Table 949Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a radical of Table D.
Table 950Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a radical of Table D.
Table 951Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a radical of Table D.
Table 952Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a radical of Table D.
Table 953Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a radical of Table D.
Table 954Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CN, and A in each case corresponds to a radical of Table D.
Table 955Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2NO2, and A in each case corresponds to a radical of Table D.
Table 956Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a radical of Table D.
Table 957Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCHF2, and A in each case corresponds to a radical of Table D.
Table 958Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a radical of Table D.
Table 959Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOCH3, and A in each case corresponds to a radical of Table D.
Table 960Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 961Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a radical of Table D.
Table 962Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 963Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a radical of Table D.
Table 964Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 965Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a radical of Table D.
Table 966Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 967Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CF3, and A in each case corresponds to a radical of Table D.
Table 968Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes bromine, and A in each case corresponds to a radical of Table D.
Table 969Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes chlorine, and A in each case corresponds to a radical of Table D.
Table 970Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH3, and A in each case corresponds to a radical of Table D.
Table 971Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH3, and A in each case corresponds to a radical of Table D.
Table 972Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCHCH2, and A in each case corresponds to a radical of Table D.
Table 973Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes ethoxy, and A in each case corresponds to a radical of Table D.
Table 974Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a radical of Table D.
Table 975Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a radical of Table D.
Table 976Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CCH, and A in each case corresponds to a radical of Table D.
Table 977Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCH3, and A in each case corresponds to a radical of Table D.
Table 978Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a radical of Table D.
Table 979Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH3, and A in each case corresponds to a radical of Table D.
Table 980Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a radical of Table D.
Table 981Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a radical of Table D.
Table 982Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a radical of Table D.
Table 983Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a radical of Table D.
Table 984Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 985Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a radical of Table D.
Table 986Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 987Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a radical of Table D.
Table 988Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a radical of Table D.
Table 989Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a radical of Table D.
Table 990Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHCH2CF3, and A in each case corresponds to a radical of Table D.
Table 991Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a radical of Table D.
Table 992Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a radical of Table D.
Table 993Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a radical of Table D.
Table 994Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a radical of Table D.
Table 995Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a radical of Table D.
Table 996Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CN, and A in each case corresponds to a radical of Table D.
Table 997Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2NO2, and A in each case corresponds to a radical of Table D.
Table 998Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a radical of Table D.
Table 999Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCHF2, and A in each case corresponds to a radical of Table D.
Table 1000Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a radical of Table D.
Table 1001Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOCH3, and A in each case corresponds to a radical of Table D.
Table 1002Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1003Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a radical of Table D.
Table 1004Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 1005Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a radical of Table D.
Table 1006Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1007Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a radical of Table D.
Table 1008Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 1009Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CF3, and A in each case corresponds to a radical of Table D.
Table 1010Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes bromine, and A in each case corresponds to a radical of Table D.
Table 1011Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes chlorine, and A in each case corresponds to a radical of Table D.
Table 1012Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH3, and A in each case corresponds to a radical of Table D.
Table 1013Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH3, and A in each case corresponds to a radical of Table D.
Table 1014Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCHCH2, and A in each case corresponds to a radical of Table D.
Table 1015Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes ethoxy, and A in each case corresponds to a radical of Table D.
Table 1016Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a radical of Table D.
Table 1017Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a radical of Table D.
Table 1018Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CCH, and A in each case corresponds to a radical of Table D.
Table 1019Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH3, and A in each case corresponds to a radical of Table D.
Table 1020Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1021Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH3, and A in each case corresponds to a radical of Table D.
Table 1022Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1023Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a radical of Table D.
Table 1024Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1025Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a radical of Table D.
Table 1026Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1027Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a radical of Table D.
Table 1028Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1029Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a radical of Table D.
Table 1030Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a radical of Table D.
Table 1031Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a radical of Table D.
Table 1032Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHCH2CF3, and A in each case corresponds to a radical of Table D.
Table 1033Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a radical of Table D.
Table 1034Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a radical of Table D.
Table 1035Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a radical of Table D.
Table 1036Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a radical of Table D.
Table 1037Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a radical of Table D.
Table 1038Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CN, and A in each case corresponds to a radical of Table D.
Table 1039Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2NO2, and A in each case corresponds to a radical of Table D.
Table 1040Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a radical of Table D.
Table 1041Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCHF2, and A in each case corresponds to a radical of Table D.
Table 1042Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a radical of Table D.
Table 1043Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOCH3, and A in each case corresponds to a radical of Table D.
Table 1044Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1045Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a radical of Table D.
Table 1046Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 1047Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a radical of Table D.
Table 1048Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1049Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a radical of Table D.
Table 1050Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 1051Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CF3, and A in each case corresponds to a radical of Table D.
Table 1052Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes bromine, and A in each case corresponds to a radical of Table D.
Table 1053Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes chlorine, and A in each case corresponds to a radical of Table D.
Table 1054Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH3, and A in each case corresponds to a radical of Table D.
Table 1055Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH3, and A in each case corresponds to a radical of Table D.
Table 1056Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCHCH2, and A in each case corresponds to a radical of Table D.
Table 1057Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes ethoxy, and A in each case corresponds to a radical of Table D.
Table 1058Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a radical of Table D.
Table 1059Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a radical of Table D.
Table 1060Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CCH, and A in each case corresponds to a radical of Table D.
Table 1061Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCH3, and A in each case corresponds to a radical of Table D.
Table 1062Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1063Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2SCH3, and A in each case corresponds to a radical of Table D.
Table 1064Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1065Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a radical of Table D.
Table 1066Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1067Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a radical of Table D.
Table 1068Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1069Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a radical of Table D.
Table 1070Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1071Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a radical of Table D.
Table 1072Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a radical of Table D.
Table 1073Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OC(═O)CF3, and A in each case corresponds to a radical of Table D.
Table 1074Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHCH2CF3, and A in each case corresponds to a radical of Table D.
Table 1075Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a radical of Table D.
Table 1076Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a radical of Table D.
Table 1077Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a radical of Table D.
Table 1078Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a radical of Table D.
Table 1079Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a radical of Table D.
Table 1080Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CN, and A in each case corresponds to a radical of Table D.
Table 1081Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2NO2, and A in each case corresponds to a radical of Table D.
Table 1082Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes cyclopropyloxy, and A in each case corresponds to a radical of Table D.
Table 1083Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCHF2, and A in each case corresponds to a radical of Table D.
Table 1084Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a radical of Table D.
Table 1085Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOCH3, and A in each case corresponds to a radical of Table D.
Table 1086Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1087Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a radical of Table D.
Table 1088Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 1089Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a radical of Table D.
Table 1090Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1091Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a radical of Table D.
Table 1092Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 1093Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CF3, and A in each case corresponds to a radical of Table D.
Table 1094Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes bromine, and A in each case corresponds to a radical of Table D.
Table 1095Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes chlorine, and A in each case corresponds to a radical of Table D.
Table 1096Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH3, and A in each case corresponds to a radical of Table D.
Table 1097Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH3, and A in each case corresponds to a radical of Table D.
Table 1098Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCHCH2, and A in each case corresponds to a radical of Table D.
Table 1099Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes ethoxy, and A in each case corresponds to a radical of Table D.
Table 1100Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a radical of Table D.
Table 1101Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a radical of Table D.
Table 1102Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CCH, and A in each case corresponds to a radical of Table D.
Table 1103Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCH3, and A in each case corresponds to a radical of Table D.
Table 1104Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1105Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2SCH3, and A in each case corresponds to a radical of Table D.
Table 1106Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1107Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a radical of Table D.
Table 1108Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1109Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a radical of Table D.
Table 1110Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1111Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a radical of Table D.
Table 1112Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1113Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a radical of Table D.
Table 1114Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a radical of Table D.
Table 1115Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OC(═O)CF3, and A in each case corresponds to a radical of Table D.
Table 1116Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHCH2CF3, and A in each case corresponds to a radical of Table D.
Table 1117Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a radical of Table D.
Table 1118Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a radical of Table D.
Table 1119Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a radical of Table D.
Table 1120Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a radical of Table D.
Table 1121Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a radical of Table D.
Table 1122Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CN, and A in each case corresponds to a radical of Table D.
Table 1123Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2NO2, and A in each case corresponds to a radical of Table D.
Table 1124Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes cyclopropyloxy, and A in each case corresponds to a radical of Table D.
Table 1125Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCHF2, and A in each case corresponds to a radical of Table D.
Table 1126Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a radical of Table D.
Table 1127Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOCH3, and A in each case corresponds to a radical of Table D.
Table 1128Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1129Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a radical of Table D.
Table 1130Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 1131Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a radical of Table D.
Table 1132Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1133Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a radical of Table D.
Table 1134Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 1135Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CF3, and A in each case corresponds to a radical of Table D.
Table 1136Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes bromine, and A in each case corresponds to a radical of Table D.
Table 1137Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes chlorine, and A in each case corresponds to a radical of Table D.
Table 1138Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH3, and A in each case corresponds to a radical of Table D.
Table 1139Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH3, and A in each case corresponds to a radical of Table D.
Table 1140Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCHCH2, and A in each case corresponds to a radical of Table D.
Table 1141Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes ethoxy, and A in each case corresponds to a radical of Table D.
Table 1142Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CHFOCH3, and A in each case corresponds to a radical of Table D.
Table 1143Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CH═CH2, and A in each case corresponds to a radical of Table D.
Table 1144Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CCH, and A in each case corresponds to a radical of Table D.
Table 1145Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCH3, and A in each case corresponds to a radical of Table D.
Table 1146Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1147Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2SCH3, and A in each case corresponds to a radical of Table D.
Table 1148Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2SCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1149Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)CH3, and A in each case corresponds to a radical of Table D.
Table 1150Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1151Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)2CH3, and A in each case corresponds to a radical of Table D.
Table 1152Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1153Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CH3, and A in each case corresponds to a radical of Table D.
Table 1154Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1155Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CH2CF3, and A in each case corresponds to a radical of Table D.
Table 1156Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes —OS(═O)2CClF2, and A in each case corresponds to a radical of Table D.
Table 1157Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OC(═O)CF3, and A in each case corresponds to a radical of Table D.
Table 1158Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHCH2CF3, and A in each case corresponds to a radical of Table D.
Table 1159Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2-cyclopropyl, and A in each case corresponds to a radical of Table D.
Table 1160Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2C(Cl)═CH2, and A in each case corresponds to a radical of Table D.
Table 1161Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CH═CF2, and A in each case corresponds to a radical of Table D.
Table 1162Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHS(═O)2CF3, and A in each case corresponds to a radical of Table D.
Table 1163Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHC(═O)CF3, and A in each case corresponds to a radical of Table D.
Table 1164Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CN, and A in each case corresponds to a radical of Table D.
Table 1165Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2NO2, and A in each case corresponds to a radical of Table D.
Table 1166Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes cyclopropyloxy, and A in each case corresponds to a radical of Table D.
Table 1167Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCHF2, and A in each case corresponds to a radical of Table D.
Table 1168Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(═O)2CHF2, and A in each case corresponds to a radical of Table D.
Table 1169Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOCH3, and A in each case corresponds to a radical of Table D.
Table 1170Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1171Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOCH(CH3)2 and A in each case corresponds to a radical of Table D.
Table 1172Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH═NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 1173Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOCH3, and A in each case corresponds to a radical of Table D.
Table 1174Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1175Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOCH(CH3)2, and A in each case corresponds to a radical of Table D.
Table 1176Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)═NOC(CH3)3, and A in each case corresponds to a radical of Table D.
The compounds of the formula I are especially suitable for efficiently combating the following pests:
insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecllia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis,
beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimllis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Diabrotica longicornis, Diabrotica semipunctata, Diabrotica 12-punctata Diabrotica speciosa, Diabrotica virgifera, Epllachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, lps typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophllus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius pyri, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria,
flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixturn, Rhagoietis cerasi, Rhagoietis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and Tipula paludosa
thrips (Thysanoptera), e.g. Dichromothrips corbetti, Dichromothrips ssp, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,
termites (Isoptera), e.g. Calotermes Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Termes natalensis, and Coptotermes formosanus,
cockroaches (Blattaria-Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis,
true bugs (Hemiptera), e.g. Acrosternum hiare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturth, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Em-Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzus persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand, Viteus vitifolii, Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., and Arilis critatus.
ants, bees, wasps, sawflies (Hymenoptera), e.g. Atha rosae, Atta cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus, Pheidole megacephala, Dasymutilla occidentalis, Bombus spp. Vespula squamosa, Paravespula vulgaris, Paravespula pennylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile,
crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus Chortoicetes terminifera, and Locustana pardalina,
Arachnoidea, such as arachnids (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Ambryomma maculatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Dermacentor andersoni, Dermacentor variabilis, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Ornithodorus moubata, Ornithodorus hermsi, Ornithodorus turicata, Ornithonyssus bacoti, Otobius megnim, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni, Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis, Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and Oligonychus pratensis, Araneida, e.g. Latrodectus mactans, and Loxosceles reclusa,
fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus,
silverfish, firebrat (Thysanura), e.g. Lepisma saccharin and Thermobia domestica,
centipedes (Chilopoda), e.g. Scutigera coleoptrata,
millipedes (Diplopoda), e.g. Narceus spp.,
Earwigs (Dermaptera), e.g. forficula auricularia,
lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus,
Plant parasitic nematodes such as root-knot nematodes, Meloidogyne arenaria, Meloidogyne chitwoodi, Meloidogyne exigua, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica and other Meloidogyne species; cyst nematodes, Globodera rostochiensis, Globodera pallida, Globodera tabacum and other Globodera species, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; seed gall nematodes, Anguina funesta, Anguina tritici and other Anguina species; stem and foliar nematodes, Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi and other Aphelenchoides species; sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species, ring nematodes, Criconema species, Criconemella species, Criconemoides species, and Mesocriconema species; stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus and other Ditylenchus species; awl nematodes, Dolichodorus species; spiral nematodes, Helicotylenchus dihystera, Helicotylenchus multicinctus and other Helicotylenchus species, Rotylenchus robustus and other Rotylenchus species, sheath nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; lance nematodes, Hoplolaimus columbus, Hoplolaimus galeatus and other Hoplolaimus species; false root-knot nematodes, Nacobbus aberrans and other Nacobbus species; needle nematodes, Longidorus elongates and other Longidorus species; pin nematodes, Paratylenchus species; lesion nematodes, Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus curvitatus, Pratylenchus goodeyi, Pratylencus neglectus, Pratylenchus penetrans, Pratylenchus scribneri, Pratylenchus vulnus, Pratylenchus zeae and other Pratylenchus species; Radinaphelenchus cocophilus and other Radinaphelenchus species; burrowing nematodes, Radopholus similis and other Radopholus species; reniform nematodes, Rotylenchulus reniformis and other Rotylenchulus species; Scutellonema species; stubby root nematodes, Trichodorus primitivus and other Trichodorus species; Paratrichodorus minor and other Paratrichodorus species; stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species and Merlinius species; citrus nematodes, Tylenchulus semipenetrans and other Tylenchulus species; dagger nematodes, Xiphinema americanum, Xiphinema index, Xiphinema diversicaudatum and other Xiphinema species, and other plant parasitic nematode species.
The formulations are prepared in a known manner (see e.g. for review U.S. Pat. No. 3,060,084, EP-A 707 445 (for liquid concentrates), Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and et seq. WO 91/13546, U.S. Pat. No. 4,172,714, U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442, U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701, U.S. Pat. No. 5,208,030, GB 2,095,558, U.S. Pat. No. 3,299,566, Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001, 2. D. A. Knowles, Chemistry and Technology of Agrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998 (ISBN 0-7514-0443-8), for example by extending the active compound with auxiliaries suitable for the formulation of agrochemicals, such as solvents and/or carriers, if desired emulsifiers, surfactants and dispersants, preservatives, antifoaming agents, anti-freezing agents, for seed treatment formulation also optionally colorants and binders.
Examples of suitable solvents are water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used.
Examples of suitable carriers are ground natural minerals (for example kaolins, clays, talc, chalk) and ground synthetic minerals (for example highly disperse silica, silicates).
Suitable emulsifiers are nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates).
Examples of dispersants are lignin-sulfite waste liquors and methylcellulose.
Suitable surfactants used are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.
Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water.
Also anti-freezing agents such as glycerin, ethylene glycol, propylene glycol and bactericides such as can be added to the formulation.
Suitable antifoaming agents are for example antifoaming agents based on silicon or magnesium stearate.
Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound(s). In this case, the active compound(s) are employed in a purity of from 90% to 100% by weight, preferably 95% to 100% by weight (according to NMR spectrum).
The compounds of formula I can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of the active compound(s) according to the invention.
Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. However, it is also possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.
The active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1% per weight.
The active compound(s) may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active compound, or even to apply the active compound without additives.
The following are examples of formulations: 1. Products for dilution with water for foliar applications. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.
A) Water-Soluble Concentrates (SL, LS)10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active compound(s) dissolves upon dilution with water, whereby a formulation with 10% (w/w) of active compound(s) is obtained.
B) Dispersible Concentrates (DC)20 parts by weight of the active compound(s) are dissolved in 75 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion, whereby a formulation with 20% (w/w) of active compound(s) is obtained.
C) Emulsifiable Concentrates (EC)15 parts by weight of the active compound(s) are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion, whereby a formulation with 15% (w/w) of active compound(s) is obtained.
D) Emulsions (EW, EO, ES)40 parts by weight of the active compound(s) are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion, whereby a formulation with 25% (w/w) of active compound(s) is obtained.
E) Suspensions (SC, OD, FS)In an agitated ball mill, 20 parts by weight of the active compound(s) are comminuted with addition of 10 parts by weight of dispersants, wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the active compound(s), whereby a formulation with 20% (w/w) of active compound(s) is obtained.
F) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)50 parts by weight of the active compound(s) are ground finely with addition of 50 parts by weight of dispersants and wetters and made as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 50% (w/w) of active compound(s) is obtained.
G) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, SS, WS)75 parts by weight of the active compound(s) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 75% (w/w) of active compound(s) is obtained.
2. Products to be applied undiluted for foliar applications. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.
H) Dustable Powders (DP, DS)5 parts by weight of the active compound(s) are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product having 5% (w/w) of active compound(s)
I) Granules (GR, FG, GG, MG)0.5 part by weight of the active compound(s) is ground finely and associated with 95.5 parts by weightof carriers, whereby a formulation with 0.5% (w/w) of active compound(s) is obtained. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted for foliar use.
J) ULV Solutions (UL, LS)10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product having 10% (w/w) of active compound(s), which is applied undiluted for foliar use.
Various types of oils, wetters, adjuvants, herbicides, fungicides, other pesticides, or bactericides may be added to the active ingredients, if appropriate just immediately prior to use (tank mix). These agents usually are admixed with the agents according to the invention in a weight ratio of 1:10 to 10:1.
The compounds of formula I are effective through both contact and ingestion.
The compounds of formula I are also suitable for the protection of the seed, plant propagules and the seedlings' roots and shoots, preferably the seeds, against soil pests and also for the treatment plant seeds which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic engineering methods.
Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders WS or granules for slurry treatment, water soluble powders SS and emulsion ES. Application to the seeds is carried out before sowing, either directly on the seeds.
The seed treatment application of the compounds of formula I or formulations containing them is carried out by spraying or dusting the seeds before sowing of the plants and before emergence of the plants.
The invention also relates to the propagation product of plants, and especially the treated seed comprising, that is, coated with and/or containing, a compound of formula I or a composition comprising it. The term “coated with and/or containing” generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.
The seed comprises the inventive compounds or compositions comprising them in an amount of from 0.1 g to 10 kg per 100 kg of seed.
Compositions of this invention may also contain other active ingredients, for example other pesticides, insecticides, herbicides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides. These additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix). For example, the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.
The following list of pesticides together with which the compounds according to the invention can be used, is intended to illustrate the possible combinations, but not to impose any limitation:
A.1. Organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
A.2. Carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamate;
A.3. Pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin;
A.4. Growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, a tetronic acid derivative of formula F1,
A.5. Nicotinic receptor agonists/antagonists compounds: clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid;
A.6. GABA antagonist compounds: acetoprole, endosulfan, ethiprole, fipronil, vaniliprole;
A.7. Macrocyclic lactone insecticides: abamectin, emamectin, milbemectin, lepimectin, spinosad;
A.8. METI I acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad;
A.9. METI II and III compounds: acequinocyl, fluacyprim, hydramethylnon;
A.10. Uncoupler compounds: chlorfenapyr;
A.11. Oxidative phosphorylation inhibitor compounds: cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
A.12. Moulting disruptor compounds: cryomazine;
A.13. Mixed Function Oxidase inhibitor compounds: piperonyl butoxide;
A.14. Sodium channel blocker compounds: indoxacarb, metaflumizone;
A.15. Various: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, N—R′-2,2-dihalo-1-R″cyclo-propanecarboxamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone or N—R′-2,2-di(R′″)propionamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-hydrazone, wherein R′ is methyl or ethyl, halo is chloro or bromo, R″ is hydrogen or methyl and R′″ is methyl or ethyl, and the aminoisothiazole compounds of formula Γ2,
wherein Ri is —CH2OCH2CH3 or H and is CF2CF2CF3 or CH2CH(CH3)3, anthranilamide compounds of formula Γ3
wherein B1 is hydrogen or a chlorine atom, B2 is a bromine atom or CF3, and RB is CH3 or CH(CH3)2, and malononitrile compounds as described in JP 2002 284608, WO 02/89579, WO 02/90320, WO 02/90321, WO 04/06677, WO 04/20399, or JP 2004 99597.
The insects may be controlled by contacting the target parasite/pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of compounds of or compositions of formula I.
“Locus” means a habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest or parasite is growing or may grow.
In general, “pesticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
The compounds or compositions of the invention can also be applied preventively to places at which occurrence of the pests is expected.
The compounds of formula I may also be used to protect growing plants from attack or infestation by pests by contacting the plant with a pesticidally effective amount of compounds of formula I. As such, “contacting” includes both direct contact (applying the compounds/compositions directly on the pest and/or plant—typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the pest and/or plant).
In the case of soil treatment or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.
For use in treating crop plants, the rate of application of the active ingredients of this invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 25 g to 600 g per hectare, more desirably from 50 g to 500 g per hectare.
Compounds of formula I and compositions comprising them can also be used for controlling and preventing infestations and infections in animals including warm-blooded animals (including humans) and fish. They are for example suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels.
Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.
The compounds of formula I and compositions comprising them are suitable for systemic and/or non-systemic control of ecto- and/or endoparasites. They are active against all or some stages of development.
Administration can be carried out both prophylactically and therapeutically. Administration of the active compounds is carried out directly or in the form of suitable preparations, orally, topically/dermally or parenterally.
For oral administration to warm-blooded animals, the formula I compounds may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the formula I compounds may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.
Alternatively, the formula I compounds may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the formula I compounds may be formulated into an implant for subcutaneous administration. In addition the formula I compound may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound.
The formula I compounds may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the formula I compound. In addition, the formula I compounds may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.
Suitable preparations are:
-
- Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;
- Emulsions and suspensions for oral or dermal administration; semi-solid preparations;
- Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base;
- Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.
Generally it is favorable to apply solid formulations which release compounds of formula I in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg. The active compounds can also be used as a mixture with synergists or with other active compounds which act against pathogenic endo- and ectoparasites.
In general, the compounds of formula I are applied in parasiticidally effective amount meaning the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.
SYNTHESIS EXAMPLESWith due modification of the starting compounds, the protocols shown in the synthesis examples below were used for obtaining further compounds I. The resulting compounds, together with physical data, are listed in the Tables 1 to 3 which follow. 2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-8-methyl-benzo[d][1,3]oxazin-4-one is known from WO 04/011447.
Example 1 Methyl-phenyl-sulfamoyl-N-(5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid (2-carbamoyl-6-methyl-phenyl))-amide, compound I.1-330.089 g Methyl-phenyl-sulfamoyl-amine was dissolved in 5 ml methylene chloride. 0.017 g sodium hydride was added at 20-25° C. and the solution was stirred for 1 hour. 0.20 g 2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-8-methyl-benzo[d][1,3]oxazin-4-one were added and the resulting mixture was refluxed for 24 h. The solvent was removed and the residue was purified by column chromatography (cyclo hexane/ethyl acetate 1:2) to yield 0.18 g methyl-phenyl-sulfamoyl-N-(5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid (2-carbamoyl-6-methyl-phenyl))-amide
Example 2 Step A: Preparation of 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid (2-carbamoyl-6-methyl-phenyl)-amide1.00 g 2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-8-methyl-benzo[d][1,3]oxazin-4-one was taken up in 10 ml of a 25% ammonia solution in water and stirred for 72 h. The solids were filtered and washed with cold water to yield 0.80 g of the amide.
Step B: S,S-Dimethyl-N-(5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid (2-carbamoyl-6-methyl-phenyl))-sulfimide, compound I.3-20.071 ml DMSO were dissolved under a nitrogen atmosphere in 0.5 ml methylene chloride and cooled to −60° C. 0.14 ml trifluoroacetic acid anhydride were slowly added at this temperature followed by the addition of 0.20 g 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid (2-carbamoyl-6-methyl-phenyl)-amide. The resulting solution was stirred at −35° C. for 1 h. After diluting with 5 ml methylene chloride, the reaction mixture was extracted with aqueous sodium hydroxide once and two times with water. The organic solvent was dried and the solvent removed. The residue was diluted with diethyl ether and the solid residue was filtered off and dried to yield 0.08 g of the desired sulfimide.
Example 3S,S Dimethyl-S-Aminosulfonium mesitylenesulfonate was prepared according to Y. Tamura et al, Tetrahedron, 1975, 31, 3035-3040.
S,S-Dimethyl-N-(5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid (2-carbamoyl-6-methyl-phenyl))-sulfimide, compound I.3-20.2 g S,S Dimethyl-S-Aminosulfonium mesitylenesulfonate were dissolved in 20 ml methylene chloride. 0.26 g potassium t-butylate, 0.54 g 2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-8-methyl-benzo[d][1,3]oxazin-4-one were added and the resulting mixture was stirred at 20-25° C. for additional 3.5 h. The reaction mixture was extracted with aqueous sodium hydroxide once and two times with water. The organic solvent was dried and the solvent removed. Column chromatography yielded 0.3 g of the desired product.
Example 4 2-{2-[5-Bromo-2-(2-chloro-phenyl)-2H-pyrazol-3-yl]-2-oxo-ethyl}-5-chloro-3-methyl-N-(1-oxo-hexahydro-1lambda*6*-thiopyran-1-ylidene)-benzamide0.2 g 2-{2-[5-Bromo-2-(2-chloro-phenyl)-2H-pyrazol-3-yl]-2-oxo-ethyl}-5-chloro-3-methyl-N-(tetrahydro-1lambda*4*-thiopyran-1-ylidene)-benzamide (0.35 mmol) were dissolved in 10 ml acetic acid. 4 mg Sodium wolframate dihydrate were added. 45 mg of a 30% solution of hydrogenperoxide was added dropwise and the resulting solution was stirred for 18 h. The reaction mixture was poured into a saturated aqueous sodium carbonate solution, methylene chloride was added and the organic pase was subsequently washed with water and saturated aqueous sodium carbonate. The organic solvent was dried and the solvent removed. Column chromatography yielded 0.07 g of the desired product, compound I.4-22.
The products were characterized by coupled High Performance Liquid Chromatography/mass spectrometry (HPLC/MS), by NMR or by their melting points.
1. Activity Against Boll Weevil (Anthonomus grandis)
The active compounds were formulated in 1:3 DMSO:water. 10 to 15 eggs were placed into microtiterplates filled with 2% agar-agar in water and 300 ppm formaline. The eggs were sprayed with 20 μl of the test solution, the plates were sealed with pierced foils and kept at 24-26° C. and 75-85% humidity with a day/night cycle for 3 to 5 days. Mortality was assessed on the basis of the remaining unhatched eggs or larvae on the agar surface and/or quantity and depth of the digging channels caused by the hatched larvae. Tests were replicated 2 times.
In this test, compounds I.1-3, I.1-11, I.1-15, I.1-32, I.1-35, I.1-48, I.1-69, I.2-2, I.3-1, 1.3-3, I.3-4, I.3-5, I.3-6, I.3-7, I.3-8, I.3-9, I.3-10, I.3-11, I.3-12, I.3-13, I.3-14, I.3-19, I.3-20, I.3-21, I.3-22, I.3-23, I.3-24, I.3-25, I.3-26, I.3-27, I.3-28, I.3-29, I.3-30, I.3-31, I.3-32, I.3-33, I.3-34, I.3-35, I.3-36, I.3-37, I.3-38, I.3-39, I.3-40, I.3-41, I.3-42, I.3-43, I.3-44, I.3-45, I.3-46, I.3-47, I.3-48, I.3-49, I.3-51, I.3-52, I.3-53, I.3-54, I.3-55, I.3-56, I.3-57, I.3-58, I.4-1, I.4-2, I.4-3, I.4-4, I.4-5, I.4-6, I.4-7, I.4-8, I.4-9, I.4-10, I.4-11, I.4-12, I.4-13, I.4-14, I.4-15, I.4-16, I.4-17, I.4-22, and I.4-23 at 2500 ppm showed over 75% mortality.
2. Activity Against Mediterranean Fruitfly (Ceratitis capitata)
The active compounds were formulated in 1:3 DMSO:water. 50 to 80 eggs were placed into microtiterplates filled with 0.5% agar-agar and 14% diet in water. The eggs were sprayed with 5 μl of the test solution, the plates were sealed with pierced foils and kept at 27-29° C. and 75-85% humidity under fluorescent light for 6 days. Mortality was assessed on the basis of the agility of the hatched larvae. Tests were replicated 2 times.
In this test, compounds I.1-12, I.1-38, I.1-43, I.1-44, I.1-49, I.3-1, I.3-8, I.3-9, I.3-10, I.3-11, I.3-12, I.3-13, I.3-14, I.3-19, I.3-20, I.3-22, I.3-23, I.3-24, I.3-25, I.3-26, I.3-27, I.3-28, I.3-29, I.3-30, I.3-32, I.3-33, I.3-34, I.3-35, I.3-37, I.3-38, I.3-39, I.3-40, I.3-41, I.3-42, I.3-43, I.3-44, I.3-45, I.3-46, I.3-47, I.3-48, I.3-49, I.3-51, I.3-52, I.3-53, I.3-54, I.3-55, I.3-56, I.3-57, I.3-58, I.4-1, I.4-2, I.4-3, I.4-4, I.4-5, I.4-6, I.4- 7, I.4-8, I.4-9, I.4-10, I.4-11, I.4-12, I.4-13, I.4-15, I.4-16, I.4-17, I.4-22 and I.4-23 at 2500 ppm showed over 75% mortality.
3. Activity Against Tobacco Budworm (Heliothis virescens)
The active compounds were formulated in 1:3 DMSO:water. 15 to 25 eggs were placed into microtiterplates filled with diet. The eggs were sprayed with 10 μl of the test solution, the plates were sealed with pierced foils and kept at 27-29° C. and 75-85% humidity under fluorescent light for 6 days. Mortality was assessed on the basis of the agility and of comparative feeding of the hatched larvae. Tests were replicated 2 times.
- 4. In this test, compounds I.1-1, I.1-3, I.1-10, I.1-11, I.1-12, I.1-13, I.1-14, I.1-15, I.1- 16, I.1-19, I.1-21, I.1-24, I.1-28, I.1-31, I.1-32, I.1-34, I.1-35, I.1-36, I.1-38, I.1-39, I.1-40, I.1-41, I.1-42, I.1-43, I.1-44, I.1-46, I.1-48, I.1-49, I.1-53, I.1-54, I.1-62, I.1-66, I.1-67, I.1-69, I.2-1, I.2-2, I.2-3, I.2-4, I.2-5, I.2-6, I.3-1, I.3-3, I.3-4, I.3-5, I.3-6, I.3-7, I.3-8, I.3-9, I.3-10, I.3-11, I.3-12, I.3-13, I.3-14, I.3- 19, I.3-20, I.3-21, I.3-22, I.3-23, I.3-24, I.3-25, I.3-26, I.3-27, I.3-28, I.3-29, I.3-30, I.3-31, I.3-32, I.3-33, I.3-34, I.3-35, I.3-36, I.3-37, I.3-38, I.3-39, I.3-40, I.3-41, I.3-42, I.3-43, I.3-44, I.3-45, I.3-46, I.3-47, I.3-48, I.3-49, I.3-51, I.3-52, I.3-53, I.3-54, I.3-55, I.3-56, I.3-57, I.3-58, I.4-1, I.4-2, I.4-3, I.4-4, I.4-5, I.4-6, I.4- 7, I.4-8, I.4-9, I.4-10, I.4-11, I.4-12, I.4-13, I.4-14, I.4-15, I.4-16, I.4-17, I.4-22 and I.4-23 at 2500 ppm showed over 75% mortality.
4. Activity Against Vetch Aphid (Megoura viciae)
The active compounds were formulated in 1:3 DMSO:water. Bean leaf disks were placed into microtiterplates filled with 0.8% agar-agar and 2.5 ppm OPUS™. The leaf disks were sprayed with 2.5 μl of the test solution and 5 to 8 adult aphids were placed into the microtiterplates which were then closed and kept at 22-24° C. and 35-45% under fluorescent light for 6 days. Mortality was assessed on the basis of vital, reproduced aphids. Tests were replicated 2 times.
In this test, compounds I.1-12, I.1-19, I.1-32, I.1-49, I.1-50, I.1-53, I.2-9, I.3-1, I.3-3, I.3-4, I.3-5, I.3-6, I.3-7, I.3-8, I.3-9, I.3-10, I.3-11, I.3-12, I.3-13, I.3- 14, I.3-19, I.3-20, I.3-21, I.3-22, I.3-23, I.3-24, I.3-25, I.3-26, I.3-27, I.3-28, I.3-29, I.3-30, I.3-32, I.3-33, I.3-34, I.3-35, I.3-36, I.3-37, I.3-38, I.3-39, I.3-40, I.3-41, I.3-42, I.3-43, I.3-44, I.3-45, I.3-47, I.3-49, I.3-51, I.3-52, I.3-53, I.3-54, I.3-55, I.3-56, I.3-57, I.3-58, I.4-1, I.4-2, I.4-3, I.4-4, I.4-5, I.4-6, I.4-7, I.4-8, I.4-9, I.4-10, I.4-11, I.4-12, I.4-13, I.4- 14, I.4-15, I.4-16, I.4-17, I.4-22 and I.4-23 at 2500 ppm showed over 75% mortality compared to 0% mortality of untreated controls.
5. Activity Against Oat Aphid (Rhopalosiphum padi)
The active compounds were formulated in 1:3 DMSO:water. Barlay leaf disk were placed into microtiterplates filled with 0.8% agar-agar and 2.5 ppm OPUS™. The leaf disks were sprayed with 2.5 μl of the test solution and 3 to 8 adult aphids were placed into the microtiterplates which were then closed and kept at 22-24° C. and 35-45% humidity under fluorescent light for 5 days. Mortality was assessed on the basis of vital aphids. Tests were replicated 2 times.
In this test, compound I.3-1 at 2500 ppm showed over 75% mortality compared to 0% mortality of untreated controls.
6. Activity Against Cotton Aphid (Aphis gossypii)
The active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic™ surfactant.
Cotton plants at the cotyledon stage (one plant per pot) were infested by placing a heavily infested leaf from the main colony on top of each cotyledon. The aphids were allowed to transfer to the host plant overnight, and the leaf used to transfer the aphids was removed. The cotyledons were dipped in the test solution and allowed to dry. After 5 days, mortality counts were made.
In this test, compound I.3-1, I.3-3, I.3-4, I.3-5, I.3-6, I.3-7, I.3-8, I.3-9, I.3-10, I.3-11, I.3-12, I.3-13, I.3-14, I.3-15, I.3-16, I.3-17, I.3-18, I.3-19, I.3-20, I.3-21, I.3-22, I.3-23, I.3-24, I.3-25, I.3-26, I.3-27, I.3-28, I.3-29, I.3-30, I.3-32, I.3-33, I.3-34, I.3-35, I.3-36, I.3-38, I.3-39, I.3-40, I.3-41, I.3-42, I.3-43, I.3-44, I.3-51, I.3-52, I.3-53, I.3-54, I.4-1, I.4-2, I.4-3, I.4-4, I.4-5, I.4-6, I.4-7, I.4-8, I.4-9, I.4-10, I.4-11, I.4-12, I.4-13 and I.4-16 at 300 ppm showed over 50% mortality.
7. Activity Against Southern Armyworm (Spodoptera eridania), 2nd Instar Larvae
The active compounds were formulated for testing the activity against insects and arachnids as a 10.000 ppm solution in a mixture of 35% acetone and water, which was diluted with water, if needed.
A Sieva lima bean leaf was dipped in the test solution and allowed to dry. The leaf was then placed in a petri dish containing a filter paper on the bottom and ten 2nd instar caterpillars. At 5 days, observations are made of mortality and reduced feeding.
In this test, compounds I.1-1, I.1-3, I.1-7, I.1-9, I.1-10, I.1-11, I.1-12, I.1-13, I.1-14, I.1-15, I.1-16, I.1-19, I.1-21, I.1-24, I.1-27, I.1-28, I.1-30, I.1-31, I.1-32, I.1-34, I.1-35, I.1-36, I.1-38, I.1-39, I.1-40, I.1-41, I.1-42, I.1-43, I.1-44, I.1-45, I.1-46, I.1-47, I.1-49, I.1-53, I.1-54, I.1-57, I.1-61, I.1-63, I.1-66, I.1-69, I.2-1, I.2-2, I.2-3, I.2-4, I.2-5, I.2-6, I.2-8, I.2-9, I.3-3, I.3-4, I.3-5, I.3-6, I.3-7, I.3-8, I.3-9, I.3-10, I.3-11, I.3-12, I.3-13, I.3-14, I.3-15, I.3-16, I.3-17, I.3-18, I.3-19, I.3-20, I.3-21, I.3-22, I.3-23, I.3-24, I.3-25, I.3-26, I.3-27, I.3-28, I.3-29, I.3-30, I.3-32, I.3-33, I.3-34, I.3-35, I.3-37, I.3-38, I.3-39, I.3-40, I.3-41, I.3-42, I.3-43, I.3-44, I.3-51, I.3-52, I.3-53, I.3-54, I.4-1, I.4-2, I.4-3, I.4-4, I.4-5, I.4-6, I.4-7, I.4-8, I.4-9, I.4-11, I.4-12, I.4-13, I.4-16, I.4-22 and I.4-23 at 300 ppm showed over 75% mortality.
8. Activity Against Silverleaf Whitefly (Bemisia argentifolii)
The active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic™ surfactant.
Selected cotton plants were grown to the cotyledon state (one plant per pot). The cotyledons were dipped into the test solution to provide complete coverage of the foliage and placed in a well-vented area to dry. Each pot with treated seedling was placed in a plastic cup and 10 to 12 whitefly adults (approximately 3-5 day old) were introduced. The insects were collected using an aspirator and an 0.6 cm, non-toxic Tygon™ tubing (R-3603) connected to a barrier pipette tip. The tip, containing the collected insects, was then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. The cups were covered with a reusable screened lid (150 micron mesh polyester screen PeCap from Tetko Inc). Test plants were maintained in the holding room at about 25° C. and 20-40% relative humidity for 3 days avoiding direct exposure to the fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment of the plants.
In this test, compound I.3-1, I.3-3, I.3-4, I.3-5, I.3-6, I.3-8, I.3-9, I.3-10, I.3-11, I.3-12, I.3-13, I.3-14, I.3-15, I.3-16, I.3-17, I.3-19, I.3-20, I.3-22, I.3-23, I.3-25, I.3-26, I.3-27, I.3-28, I.3-30, I.4-1, I.4-2 and I.4-3 at 300 ppm showed over 90% mortality.
9. Activity Against Diamond Back Moth (Plutella xylostella)
The active compounds were formulated in 50:50 acetone:water and 0.1% (vol/vol) Alkamuls EL 620 surfactant. A 6 cm leaf disk of cabbage leaves was dipped in the test solution for 3 seconds and allowed to air dry in a Petri plate lined with moist filter paper. The leaf disk was inoculated with 10 third instar larvae and kept at 25-27° C. and 50-60% humidity for 3 days. Mortality was assessed after 72 h of treatment.
In this test, compounds I.1-1, I.1-7, I.1-9, I.1-15, I.1-19, I.1-21, I.1-24, I.1-27, I.1-28, I.1-29, I.1-31, I.1-32, I.1-45, I.1-47, I.1-61, I.1-63, I.3-5, I.3-6, I.3-7, I.3-8, I.3-9, I.3-10, I.3-11, I.3-12, I.3-13, I.3-14, I.3-15, I.3-16, I.3-17, I.3-18, I.3-19, I.3-20, I.3-21, I.3-22, I.3-23, I.3-24, I.3-25, I.3-26, I.3-27, I.3-28, I.3-29, I.3-30, I.3-31, I.3-32, I.3-33, I.3-34, I.3-35, I.3-36, I.3-37, I.3-38, I.3-39, I.3-40, I.3-41, I.3-42, I.3-43, I.3-44, I.3-45, I.3-46, I.3-47, I.3-48, I.3-49, I.3-51, I.3-52, I.3-53, I.3-54, I.3-55, I.3-56, I.3-57, I.3-58, I.3-59, I.3-60, I.3-61, I.3-62, I.3-63, I.4-1, I.4-2, I.4-3, I.4-4, I.4-5, I.4-6, I.4-7, I.4-8, I.4-9, I.4-10, I.4-11, I.4-12, I.4-13, I.4-16, I.4-17, I.4-18, I.4-19, and I.4-22 at 300 ppm showed over 75% mortality.
10. Activity Against Argentine Ant (Linepithema humile), Harvester Ant (Pogonomyrmex Californicus), Acrobat Ant (Crematogaster Spp.), Carpenter Ant (Camponotus floridanus), Fire Ant (Solenopsis invicta), House Fly (Musca domestica), Stable Fly (Stomoxys calcitrans), Flesh Fly (Sarcophaga sp.), Yellowfever Mosquito (Aedes aegyptii), House Mosquito (Culex quinquefasciatus), Malaria Mosquito (Anopheles albimanus), German Cockroach (Blattella Germanica), Cat Flea (Ctenocephalides felis), and Brown Dog Tick (Rhipicephalus sanguineus) Via Glass Contact
Glass vials were treated with 0.5 ml of a solution of active ingredient in acetone and allowed to dry. Insects or ticks were placed into each vial together with some food and moisture supply. The vials were kept at 22° C. and were observed for treatment effects at various time intervals.
In this test, compounds I.3-4, I.3-5 and I.3-6 at 10 ppm showed over 70% mortality of yellowfever mosquito.
11. Activity Against Yellowfever Mosquito (Aedes aegyptii), House Mosquito (Culex quinquefasciatus) and Malaria Mosquito (Anopheles albimanus) Larvae Via Water Treatment
Well plates were used as test arenas. The active ingredient was dissolved in acetone and diluted with water to obtain the concentrations needed. The final solutions containing appr. 1% acetone were placed into each well. Approximately 10 mosquito larvae (4th-instars) in 1 ml water were added to each well. Larvae were fed one drop of liver powder each day. The dishes were covered and maintained at 22° C. Mortality was recorded daily and dead larvae and live or dead pupae were removed daily. At the end of the test remaining live larvae were recorded and percent mortality was calculated.
In this test, compounds I.1-37, I.1-38, I.1-49, I.1-69, I.3-4, I.3-5, I.3-6 and I.3-7 at 10 ppm showed over 70% mortality of yellowfever mosquito.
12. Activity Against Root-Knot Nematode (Meloidogyne incognita):
Test compounds are prepared and formulated into aqueous formulations using acetone. Tomato plants (var. Bonny Best) are grown in the greenhouse in plastic tubs (4 to 6 plants per tub). The plants and soil (a 50:50 mixture of sand and “New Egypt” sandy loam) are infested with M. incognita J2 (to establish the “in-house” colony, M. incognita J2 were initially acquired from Auburn University). The plants are kept pruned and are used on an “as needed” basis. The tomato plants are kept in the cylinder containing hydroponic solution and aerated until the nematodes are no longer present in the solution (usually about 60 days). The cultures are checked daily by eluting a small volume (approximately 20 ml) from the bottom of a funnel attached to the cylinder into a small crystallizing dish and observed using a binocular dissecting scope. If needed for testing, the nematodes are cleaned and concentrated by pouring the culture solution through a sieve for cleaning and a sieve for concentrating. The nematodes are then resuspended in water to a concentration of approximately 20 to 50 nematodes per 50 μl. These are counted by putting 25 μl of the nematode solution into a well of an unused well of an assay plate. The total is then multiplied by 2 for a final total of nematodes per 50 μl of solution. To microtiter plates containing about 1.0 mg of compound, 80:20 acetone is added to each well and the solution is mixed to obtain the desired compound concentration. The nematode solution is added to each plate. The plates are then sealed and they are placed in an incubator at 27° C. and 50% (+/−2%) relative humidity. After 72 hours, the population mortality is read, whereby immobility of nematodes is regarded as mortality.
Claims
1. (canceled)
2: A compound of formula (I)
- wherein
- R1 is hydrogen;
- A is A1
- wherein # denotes the binding site; R2 and R3 each independently are R6, or R2 and R3 together with the sulfur atom to which they are attached form a saturated, partially unsaturated or unsaturated 3- to 8-membered ring which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, which ring can be fused with one or two saturated, partially unsaturated or unsaturated 5- to 6-membered rings which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein all of the above rings are unsubstituted or substituted by any combination of 1 to 6 groups R8; G is oxygen or sulfur; R6 is C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C3-C8-cycloalkynyl, phenyl, naphthyl, biphenyl, or a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein all of these groups are unsubstituted or substituted by any combination of 1 to 6 groups R8; R8 is R9; or two groups R8 together with the atoms to which they are attached form a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which may contain 1 to 4 heteroatoms/heterogroups selected from oxygen, nitrogen, sulfur, SO and SO2, and which ring system is unsubstituted or substituted with any combination of 1 to 6 groups R9. R9 is R10, R11, —C(=G)R10, —C(═NOR10)R10, —C(═NNR102)R10, —C(=G)OR10, —C(=G)NR102, —OC(=G)R10, —OC(=G)OR10, —NR10C(=G)R10, —N[C(=G)R10 ]2, —NR10C(=G)OR10, —C(=G)NR10—NR102, —C(=G)NR10—NR10[C(=G)R10], —NR10—C(=G)NR102, —NR10—NR10C(=G)R10, —NR10—N[C(=G)R10]2, —N[(C=G)R10]—NR102, —NR10—NR10[(C=G)GR10], —NR10[(C=G)NR102, —NR10[C═NR10]R10, —NR10 (C═NR10)NR102, —O—NR102, —O—NR10 (C=G)R10, —SO2NR102, —NR10SO2R10, —SO2OR10, —OSO2R10, —OR10, —NR102, —SiR103, —PR102, —P(=G)R10, —SOR10, —SO2R10, —PG2R102, —PG3R102 or two groups R9 together are (=G),)(═N—R10), (═CR102), (═CHR10), or (═CH2); R10 is C1-C10, C2-C10-alkenyl, C2-C10-alkynyl, C3-C8-cycloalkyl, C4-C8-cycloalkenyl, C3-C8-cycloalkyl-C1-C4-alkyl, C4-C8-cycloalkenyl-C1-C4-alkyl, C3-C8-cycloalkyl-C2-C4-alkenyl, C4-C8-cycloalkenyl-C2-C4-alkenyl, C1-C10-alkyl-C3-C8-cycloalkyl, C2-C10-alkenyl-C3-C8-cycloalkyl, C2-C10-alkynyl-C3-C8-cycloalkyl, C1-C10-alkyl-C4-C8-cycloalkenyl, C2-C10-alkenyl-C4-C8-cycloalkenyl, C2-C10-alkynyl-C4-C8-cycloalkenyl, a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sufur, wherein the above groups are unsubstituted or substituted with any combination of from 1 to 6 groups R11; R11 is halogen, cyano, nitro, hydroxy, mercapto, amino, formyl, C1-C10-alkylcarbonyl, C1-C10-alkoxy, C2-C10-alkenyloxy, C2-C10-alkynyloxy, C1-C10-haloalkoxy, C3-C10-haloalkenyloxy, C3-C10-haloalkynyloxy, C3-C8-cycloalkoxy, C4-C8-cycloalkenyloxy, C3-C8-halocycloalkoxy, C4-C8-halocycloalkenyloxy, C3-C8-cycloalkyl-C1-C4-alkoxy, C4-C8-cycloalkenyl-C1-C4-alkoxy, C3-C8-cycloalkyl-C2-C4-alkenyloxy, C4-C8-cycloalkenyl-C2-C4-alkenyloxy, C1-C10-alkyl-C3-C8-cycloalkoxy, C1-C10-alkenyl-C3-C8-cycloalkoxy, C1-C10-alkynyl-C3-C8-cycloalkoxy, C1-C10-alkyl-C3-C8-cycloalkenyloxy, C1-C10-alkenyl-C3-C8-cycloalkenyloxy, C1-C4-alkoxy-C1-C10-alkoxy, C1-C4-alkoxy-C2-C10-alkenyloxy, mono- or di(C1-C10-alkyl)carbamoyl, mono- or di(C1-C10-haloalkyl)carbamoyl, mono- or di(C3-C8-cycloalkyl)carbamoyl, C1-C10-alkoxycarbonyl, C3-C8-cycloalkoxycarbonyl, C1-C10-alkylcarbonyloxy, C3-C8-cyclo alkylcarbonyloxy, C1-C10-haloalkoxycarbonyl, C1-C10-haloalkylcarbonyloxy, C1-C10-alkanamido, C1-C10-haloalkanamido, C2-C10-alkenamido, C3-C8-cycloalkanamido, C3-C8-cycloalkyl-C1-C4-alkanamido, C1-C10-alkylthio, C2-C10-alkenylthio, C2-C10-alkynylthio, C1-C10-haloalkylthio, C2-C10-haloalkenylthio, C2-C10-haloalkynylthio, C3-C8-cycloalkylthio, C3-C8-cycloalkenylthio, C3-C8-halocycloalkylthio, C3-C8-halocycloalkenylthio, C3-C8-cycloalkyl-C1-C4-alkylthio, C4-C8-cycloalkenyl-C1-C4-alkylthio, C3-C8-cycloalkyl-C2-C4-alkenylthio, C4-C8-cycloalkenyl-C2-C4-alkenylthio, C1-C10-alkyl-C3-C8-cycloalkylthio, C1-C10-alkenyl-C3-C8-cycloalkylthio, C1-C10-alkynyl-C3-C8-cycloalkylthio, C1-C10-alkyl-C3-C8-cycloalkenylthio, C1-C10-alkenyl-C3-C8-cycloalkenylthio, C1-C10-alkylsulfinyl, C2-C10-alkenylsulfinyl, C2-C10-alkynylsulfinyl, C1-C10-haloalkylsulfinyl, C2-C10-haloalkenylsulfinyl, C2-C10-haloalkynylsulfinyl, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkenylsulfinyl, C3-C8-halocycloalkylsulfinyl, C3-C8-halocycloalkenylsulfinyl, C3-C8-cycloalkyl-C1-C4-alkylsulfinyl, C4-C8-cycloalkenyl-C1-C4-alkylsulfinyl, C3-C8-cycloalkyl-C2-C4-alkenylsulfinyl, C4-C8-cycloalkenyl-C2-C4-alkenylsulfinyl, C1-C10-alkyl-C3-C8-cycloalkylsulfinyl, C1-C10-alkenyl-C3-C8-cycloalkylsulfinyl, C1-C10-alkynyl-C3-C8-cycloalkylsulfinyl, C1-C10-alkyl-C3-C8-cycloalkenylsulfinyl, C3-C8-cycloalkenylsulfinyl, C1-C10-alkylsulfonyl, C2-C10-alkenylsulfonyl, C2-C10-alkynylsulfonyl, C1-C10-haloalkylsulfonyl, C2-C10-haloalkenylsulfonyl, C2-C10-haloalkynylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkenylsulfonyl, C3-C8-halocycloalkylsulfonyl, C3-C8-halocycloalkenylsulfonyl, C3-C8-cycloalkyl-C1-C4-alkylsulfonyl, C4-C8-cycloalkenyl-C1-C4-alkylsulfonyl, C3-C8-cycloalkyl-C2-C4-alkenylsulfonyl, C4-C8-cycloalkenyl-C2-C4-alkenylsulfonyl, C1-C10-alkyl-C3-C8-cycloalkylsulfonyl, C1-C10-alkenyl-C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C1-C10-alkyl-C3-C8-cycloalkenylsulfonyl, C1-C10-alkenyl-C3-C8-cycloalkenylsulfonyl, di(C1-C10-alkyl)amino, C1-C10-alkylamino, C2-C10-alkenylamino, C2-C10-alkynylamino, C1-C10-alkyl-C2-C10-alkenylamino, C1-C10-alkyl-C2-C10-alkynylamino, C1-C10-haloalkylamino, C2-C10-haloalkenylamino, C2-C10-haloalkynylamino, C3-C8-cycloalkylamino, C3-C8-cycloalkenylamino, C3-C8-halocycloalkylamino, C3-C8-halocycloalkenylamino, C3-C8-cycloalkyl-C1-C4-alkylamino, C4-C8-cycloalkenyl-C1-C4-alkylamino, C3-C8-cycloalkyl-C2-C4-alkenylamino, C4-C8-cycloalkenyl-C2-C4-alkenylamino, C1-C10-alkyl-C3-C8-cycloalkylamino, C1-C10-alkenyl-C3-C8-cycloalkylamino, C1-C10-alkynyl-C3-C8-cycloalkylamino, C1-C10-alkyl-C3-C8-cycloalkenylamino, C1-C10-alkenyl-C3-C8-cycloalkenylamino, tri(C1-C10-alkyl)silyl, aryl, aryloxy, arylthio, arylamino, aryl-C1-C4-alkoxy, aryl-C3-C4-alkenyloxy, aryl-C2-C4-alkenylthio, aryl-C1-C4-alkylamino, aryl-C3-C4-alkenylamino, triarylsilyl, wherein aryl is phenyl, naphthyl or biphenyl, or a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein these aryl and these heterocyclic ringsystems are unsubstituted or substituted with any combination of from 1 to 6 groups selected from halogen, cyano, nitro, amino, hydroxy, mercapto, C1-C4-alkyl, C3-C8-cycloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkylthio, di(C1-C4-alkyl)amino, C1-C4-alkylamino, C1-C4-haloalkylamino, formyl and C1-C4-alkylcarbonyl;
- Q1 is hydrogen, halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl;
- Q2 is halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl;
- Q3 is halogen; or C1-C10-alkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C10-alkyl-C3-C8-cycloalkyl, C1-C10-haloalkyl-C3-C8-cycloalkyl, each unsubstituted or independently substituted with 1 to 2 groups selected from cyano, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, and C1-C10-alkoxycarbonyl; or
- Q3 is OR14, S(O)qR14, NR15R16, OS(O)2R17, NR16S(O)2R17, C(S)NH2, C(R18)═NOR18, C3-C8-cycloalkyl-C1-C4-alkyl, C1-C10-alkylaminothiocarbonyl, or di(C1-C10-alkyl)aminothiocarbonyl; R14 is C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, C1-C4-alkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C4-alkyl, C1-C4-haloalkyl-C3-C8-cycloalkyl, or C1-C10-haloalkylcarbonyl, each unsubstituted or substituted with 1 R19; R15 is C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C4-alkyl-C3-C8-cycloalkyl, C1-C4-haloalkyl-C3-C8-cycloalkyl, or C1-C10-haloalkylcarbonyl, each unsubstituted or substituted with 1 R19; R16 is hydrogen; or C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C4-alkyl-C3-C8-cycloalkyl, or C1-C4-haloalkyl-C3-C8-cycloalkyl, each unsubstituted or substituted with 1 R19; R17 is C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C4-alkyl-C3-C8-cycloalkyl, or C1-C4-haloalkyl-C3-C8-cycloalkyl, each unsubstituted or substituted with 1 R19; R19 is cyano, nitro, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl C1-C10-haloalkylsulfonyl, C1-C10-alkoxycarbonyl, C1-C10-alkylamino, or di(C1-C10-alkyl)amino; or R19 is phenyl or a heteroaromatic 5- or 6-membered ring which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, the phenyl radical and the heteroaromatic ring being unsubstituted or substituted with any combination of from 1 to 3 groups selected from halogen, cyano, nitro, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-alkylamino, di(C1-C10-alkyl)amino, C3-C8-cycloalkylamino, C1-C10-alkyl-C3-C8-cycloalkylamino, C1-C10-alkylcarbonyl, C1-C10-alkoxycarbonyl, C1-C10-alkylaminocarbonyl, di(C1-C10-alkyl)aminocarbonyl and tri(C1-C10)-alkylsilyl; R18 is the same or different: hydrogen, C1-C10-alkyl, or C1-C10-haloalkyl;
- q is 0, 1 or 2;
- Q4 is halogen or C1-C4-haloalkyl
- X and Y are each oxygen;
- V and V′ are each CH;
- W is N;
- n is 0 or 1;
- p is 1;
- and/or an enantiomer, a salt, and/or an N-oxide thereof.
3: The compound of claim 2, wherein
- Q3 is halogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, each unsubstituted or independently substituted with 1 to 2 groups selected from cyano, C1-C10-alkoxy, C1-C10-haloalkoxy or C1-C10-alkylthio, or
- Q3 is OR14, S(O)qR14, NR15R16, OS(O)2R17, C(S)NH2, C(R18)═NOR18; wherein R14 is C1-C10-alkyl or C3-C8-cycloalkyl unsubstituted or substituted with 1 R19; and R15 is C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, each unsubstituted or substituted with 1 R19; and R16 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, each unsubstituted or substituted with 1 R19; and R17 is C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C8-cycloalkyl, each unsubstituted or substituted with 1 R19; and R18 is hydrogen, C1-C10-alkyl, or C1-C10-haloalkyl; and R19 is cyano, nitro, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio;
- Q4 is halogen and is in the ortho-position.
4: The compound of claim 2, wherein
- Q3 is halogen, C1-C4-haloalkyl or C1-C4-haloalkoxy.
5: The compound of claim 2, wherein
- R2 and R3 each independently are C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C8-cycloalkyl, or phenyl, wherein these groups are unsubstituted or substituted by any combination of 1 to 6 groups selected from R11, R11 is halogen, cyano, nitro, hydroxy, mercapto, amino, C1-C10-alkoxy, C1-C10-haloalkoxy, C3-C8-cycloalkoxy, C1-C10-alkoxycarbonyl, C1-C10-aIkylcarbonyloxy, C1-C10-alkanamido, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, di(C1-C10-alkyl)amino or C1-C10-alkylamino.
6: A compound of the formula IA TABLE C No. A Re Rf IA-139 CH3 CH3 IA-140 A1.1 CH2CH3 CH3 IA-141 A1.1 CH═CH2 CH3 IA-142 A1.1 CH2CH2CH3 CH3 IA-143 A1.1 CH(CH3)2 CH3 IA-144 A1.1 CH2CH2CH2CH3 CH3 IA-145 A1.1 C(CH3)3 CH3 IA-146 A1.1 CH2CH(CH3)2 CH3 IA-147 A1.1 CH(CH3)CH2CH3 CH3 IA-148 A1.1 CH2CHCH2 CH3 IA-149 A1.1 CH2CCH CH3 IA-150 A1.1 CH(CH3)CH═CH2 CH3 IA-151 A1.1 CHF2 CH3 IA-152 A1.1 CH2Cl CH3 IA-153 A1.1 CH2CH2CN CH3 IA-154 A1.1 CH2CH2Cl CH3 IA-155 A1.1 CH2CH2OH CH3 IA-156 A1.1 CH2CH2CH2OH CH3 IA-157 A1.1 CH2CH(OH)CH2OH CH3 IA-158 A1.1 CH2CH(OCH3)2 CH3 IA-159 A1.1 CH2SCH3 CH3 IA-160 A1.1 (CH2)3SCH3 CH3 IA-161 A1.1 CH2S(═O)CH3 CH3 IA-162 A1.1 CH2S(═O)2CH3 CH3 IA-163 A1.1 CH2C(═O)CH3 CH3 IA-164 A1.1 CH2C(═O)CH2CH3 CH3 IA-165 A1.1 CH2COOH CH3 IA-166 A1.1 CH2COOCH3 CH3 IA-167 A1.1 CH2COOCH2CH3 CH3 IA-168 A1.1 cyclo-C3H5 CH3 IA-169 A1.1 cyclo-C4H7 CH3 IA-170 A1.1 cyclo-C5H9 CH3 IA-171 A1.1 cyclo-C6H11 CH3 IA-172 A1.1 C6H5 CH3 IA-173 A1.1 CH2CH3 CH2CH3 IA-174 A1.1 CH═CH2 CH2CH3 IA-175 A1.1 CH2CH2CH3 CH2CH3 IA-176 A1.1 CH(CH3)2 CH2CH3 IA-177 A1.1 CH2CH2CH2CH3 CH2CH3 IA-178 A1.1 C(CH3)3 CH2CH3 IA-179 A1.1 CH2CH(CH3)2 CH2CH3 IA-180 A1.1 CH(CH3)CH2CH3 CH2CH3 IA-181 A1.1 CH2CHCH2 CH2CH3 IA-182 A1.1 CH2CCH CH2CH3 IA-183 A1.1 CH(CH3)CH═CH2 CH2CH3 IA-184 A1.1 CHF2 CH2CH3 IA-185 A1.1 CH2Cl CH2CH3 IA-186 A1.1 CH2CH2CN CH2CH3 IA-187 A1.1 CH2CH2Cl CH2CH3 IA-188 A1.1 CH2CH2OH CH2CH3 IA-189 A1.1 CH2CH2CH2OH CH2CH3 IA-190 A1.1 CH2CH(OH)CH2OH CH2CH3 IA-191 A1.1 CH2CH(OCH3)2 CH2CH3 IA-192 A1.1 CH2SCH3 CH2CH3 IA-193 A1.1 (CH2)3SCH3 CH2CH3 IA-194 A1.1 CH2S(═O)CH3 CH2CH3 IA-195 A1.1 CH2S(═O)2CH3 CH2CH3 IA-196 A1.1 CH2C(═O)CH3 CH2CH3 IA-197 A1.1 CH2C(═O)CH2CH3 CH2CH3 IA-198 A1.1 CH2COOH CH2CH3 IA-199 A1.1 CH2COOCH3 CH2CH3 IA-200 A1.1 CH2COOCH2CH3 CH2CH3 IA-201 A1.1 cyclo-C3H5 CH2CH3 IA-202 A1.1 cyclo-C4H7 CH2CH3 IA-203 A1.1 cyclo-C5H9 CH2CH3 IA-204 A1.1 cyclo-C6H11 CH2CH3 IA-205 A1.1 C6H5 CH2CH3 IA-206 A1.1 CH═CH2 CH═CH2 IA-207 A1.1 CH2CH2CH3 CH═CH2 IA-208 A1.1 CH(CH3)2 CH═CH2 IA-209 A1.1 CH2CH2CH2CH3 CH═CH2 IA-210 A1.1 C(CH3)3 CH═CH2 IA-211 A1.1 CH2CH(CH3)2 CH═CH2 IA-212 A1.1 CH(CH3)CH2CH3 CH═CH2 IA-213 A1.1 CH2CHCH2 CH═CH2 IA-214 A1.1 CH2CCH CH═CH2 IA-215 A1.1 CH(CH3)CH═CH2 CH═CH2 IA-216 A1.1 CHF2 CH═CH2 IA-217 A1.1 CH2Cl CH═CH2 IA-218 A1.1 CH2CH2CN CH═CH2 IA-219 A1.1 CH2CH2Cl CH═CH2 IA-220 A1.1 CH2CH2OH CH═CH2 IA-221 A1.1 CH2CH2CH2OH CH═CH2 IA-222 A1.1 CH2CH(OH)CH2OH CH═CH2 IA-223 A1.1 CH2CH(OCH3)2 CH═CH2 IA-224 A1.1 CH2SCH3 CH═CH2 IA-225 A1.1 (CH2)3SCH3 CH═CH2 IA-226 A1.1 CH2S(═O)CH3 CH═CH2 IA-227 A1.1 CH2S(═O)2CH3 CH═CH2 IA-228 A1.1 CH2C(═O)CH3 CH═CH2 IA-229 A1.1 CH2C(═O)CH2CH3 CH═CH2 IA-230 A1.1 CH2COOH CH═CH2 IA-231 A1.1 CH2COOCH3 CH═CH2 IA-232 A1.1 CH2COOCH2CH3 CH═CH2 IA-233 A1.1 cyclo-C3H5 CH═CH2 IA-234 A1.1 cyclo-C4H7 CH═CH2 IA-235 A1.1 cyclo-C5H9 CH═CH2 IA-236 A1.1 cyclo-C6H11 CH═CH2 IA-237 A1.1 C6H5 CH═CH2 IA-238 A1.1 CH2CH2CH3 CH2CH2CH3 IA-239 A1.1 CH(CH3)2 CH2CH2CH3 IA-240 A1.1 CH2CH2CH2CH3 CH2CH2CH3 IA-241 A1.1 C(CH3)3 CH2CH2CH3 IA-242 A1.1 CH2CH(CH3)2 CH2CH2CH3 IA-243 A1.1 CH(CH3)CH2CH3 CH2CH2CH3 IA-244 A1.1 CH2CHCH2 CH2CH2CH3 IA-245 A1.1 CH2CCH CH2CH2CH3 IA-246 A1.1 CH(CH3)CH═CH2 CH2CH2CH3 IA-247 A1.1 CHF2 CH2CH2CH3 IA-248 A1.1 CH2Cl CH2CH2CH3 IA-249 A1.1 CH2CH2CN CH2CH2CH3 IA-250 A1.1 CH2CH2Cl CH2CH2CH3 IA-251 A1.1 CH2CH2OH CH2CH2CH3 IA-252 A1.1 CH2CH2CH2OH CH2CH2CH3 IA-253 A1.1 CH2CH(OH)CH2OH CH2CH2CH3 IA-254 A1.1 CH2CH(OCH3)2 CH2CH2CH3 IA-255 A1.1 CH2SCH3 CH2CH2CH3 IA-256 A1.1 (CH2)3SCH3 CH2CH2CH3 IA-257 A1.1 CH2S(═O)CH3 CH2CH2CH3 IA-258 A1.1 CH2S(═O)2CH3 CH2CH2CH3 IA-259 A1.1 CH2C(═O)CH3 CH2CH2CH3 IA-260 A1.1 CH2C(═O)CH2CH3 CH2CH2CH3 IA-261 A1.1 CH2COOH CH2CH2CH3 IA-262 A1.1 CH2COOCH3 CH2CH2CH3 IA-263 A1.1 CH2COOCH2CH3 CH2CH2CH3 IA-264 A1.1 cyclo-C3H5 CH2CH2CH3 IA-265 A1.1 cyclo-C4H7 CH2CH2CH3 IA-266 A1.1 cyclo-C5H9 CH2CH2CH3 IA-267 A1.1 cyclo-C6H11 CH2CH2CH3 IA-268 A1.1 C6H5 CH2CH2CH3 IA-269 A1.1 CH(CH3)2 CH(CH3)2 IA-270 A1.1 CH2CH2CH2CH3 CH(CH3)2 IA-271 A1.1 C(CH3)3 CH(CH3)2 IA-272 A1.1 CH2CH(CH3)2 CH(CH3)2 IA-273 A1.1 CH(CH3)CH2CH3 CH(CH3)2 IA-274 A1.1 CH2CHCH2 CH(CH3)2 IA-275 A1.1 CH2CCH CH(CH3)2 IA-276 A1.1 CH(CH3)CH═CH2 CH(CH3)2 IA-277 A1.1 CHF2 CH(CH3)2 IA-278 A1.1 CH2Cl CH(CH3)2 IA-279 A1.1 CH2CH2CN CH(CH3)2 IA-280 A1.1 CH2CH2Cl CH(CH3)2 IA-281 A1.1 CH2CH2OH CH(CH3)2 IA-282 A1.1 CH2CH2CH2OH CH(CH3)2 IA-283 A1.1 CH2CH(OH)CH2OH CH(CH3)2 IA-284 A1.1 CH2CH(OCH3)2 CH(CH3)2 IA-285 A1.1 CH2SCH3 CH(CH3)2 IA-286 A1.1 (CH2)3SCH3 CH(CH3)2 IA-287 A1.1 CH2S(═O)CH3 CH(CH3)2 IA-288 A1.1 CH2S(═O)2CH3 CH(CH3)2 IA-289 A1.1 CH2C(═O)CH3 CH(CH3)2 IA-290 A1.1 CH2C(═O)CH2CH3 CH(CH3)2 IA-291 A1.1 CH2COOH CH(CH3)2 IA-292 A1.1 CH2COOCH3 CH(CH3)2 IA-293 A1.1 CH2COOCH2CH3 CH(CH3)2 IA-294 A1.1 cyclo-C3H5 CH(CH3)2 IA-295 A1.1 cyclo-C4H7 CH(CH3)2 IA-296 A1.1 cyclo-C5H9 CH(CH3)2 IA-297 A1.1 cyclo-C6H11 CH(CH3)2 IA-298 A1.1 C6H5 CH(CH3)2 IA-299 A1.1 CH2CH2CH2CH3 CH2CH2CH2CH3 IA-300 A1.1 C(CH3)3 CH2CH2CH2CH3 IA-301 A1.1 CH2CH(CH3)2 CH2CH2CH2CH3 IA-302 A1.1 CH(CH3)CH2CH3 CH2CH2CH2CH3 IA-303 A1.1 CH2CHCH2 CH2CH2CH2CH3 IA-304 A1.1 CH2CCH CH2CH2CH2CH3 IA-305 A1.1 CH(CH3)CH═CH2 CH2CH2CH2CH3 IA-306 A1.1 CHF2 CH2CH2CH2CH3 IA-307 A1.1 CH2Cl CH2CH2CH2CH3 IA-308 A1.1 CH2CH2CN CH2CH2CH2CH3 IA-309 A1.1 CH2CH2Cl CH2CH2CH2CH3 IA-310 A1.1 CH2CH2OH CH2CH2CH2CH3 IA-311 A1.1 CH2CH2CH2OH CH2CH2CH2CH3 IA-312 A1.1 CH2CH(OH)CH2OH CH2CH2CH2CH3 IA-313 A1.1 CH2CH(OCH3)2 CH2CH2CH2CH3 IA-314 A1.1 CH2SCH3 CH2CH2CH2CH3 IA-315 A1.1 (CH2)3SCH3 CH2CH2CH2CH3 IA-316 A1.1 CH2S(═O)CH3 CH2CH2CH2CH3 IA-317 A1.1 CH2S(═O)2CH3 CH2CH2CH2CH3 IA-318 A1.1 CH2C(═O)CH3 CH2CH2CH2CH3 IA-319 A1.1 CH2C(═O)CH2CH3 CH2CH2CH2CH3 IA-320 A1.1 CH2COOH CH2CH2CH2CH3 IA-321 A1.1 CH2COOCH3 CH2CH2CH2CH3 IA-322 A1.1 CH2COOCH2CH3 CH2CH2CH2CH3 IA-323 A1.1 cyclo-C3H5 CH2CH2CH2CH3 IA-324 A1.1 cyclo-C4H7 CH2CH2CH2CH3 IA-325 A1.1 cyclo-C5H9 CH2CH2CH2CH3 IA-326 A1.1 cyclo-C6H11 CH2CH2CH2CH3 IA-327 A1.1 C6H5 CH2CH2CH2CH3 IA-328 A1.1 C(CH3)3 C(CH3)3 IA-329 A1.1 CH2CH(CH3)2 C(CH3)3 IA-330 A1.1 CH(CH3)CH2CH3 C(CH3)3 IA-331 A1.1 CH2CHCH2 C(CH3)3 IA-332 A1.1 CH2CCH C(CH3)3 IA-333 A1.1 CH(CH3)CH═CH2 C(CH3)3 IA-334 A1.1 CHF2 C(CH3)3 IA-335 A1.1 CH2Cl C(CH3)3 IA-336 A1.1 CH2CH2CN C(CH3)3 IA-337 A1.1 CH2CH2Cl C(CH3)3 IA-338 A1.1 CH2CH2OH C(CH3)3 IA-339 A1.1 CH2CH2CH2OH C(CH3)3 IA-340 A1.1 CH2CH(OH)CH2OH C(CH3)3 IA-341 A1.1 CH2CH(OCH3)2 C(CH3)3 IA-342 A1.1 CH2SCH3 C(CH3)3 IA-343 A1.1 (CH2)3SCH3 C(CH3)3 IA-344 A1.1 CH2S(═O)CH3 C(CH3)3 IA-345 A1.1 CH2S(═O)2CH3 C(CH3)3 IA-346 A1.1 CH2C(═O)CH3 C(CH3)3 IA-347 A1.1 CH2C(═O)CH2CH3 C(CH3)3 IA-348 A1.1 CH2COOH C(CH3)3 IA-349 A1.1 CH2COOCH3 C(CH3)3 IA-350 A1.1 CH2COOCH2CH3 C(CH3)3 IA-351 A1.1 cyclo-C3H5 C(CH3)3 IA-352 A1.1 cyclo-C4H7 C(CH3)3 IA-353 A1.1 cyclo-C5H9 C(CH3)3 IA-354 A1.1 cyclo-C6H11 C(CH3)3 IA-355 A1.1 C6H5 C(CH3)3 IA-356 A1.1 CH2CH(CH3)2 CH2CH(CH3)2 IA-357 A1.1 CH(CH3)CH2CH3 CH2CH(CH3)2 IA-358 A1.1 CH2CHCH2 CH2CH(CH3)2 IA-359 A1.1 CH2CCH CH2CH(CH3)2 IA-360 A1.1 CH(CH3)CH═CH2 CH2CH(CH3)2 IA-361 A1.1 CHF2 CH2CH(CH3)2 IA-362 A1.1 CH2Cl CH2CH(CH3)2 IA-363 A1.1 CH2CH2CN CH2CH(CH3)2 IA-364 A1.1 CH2CH2Cl CH2CH(CH3)2 IA-365 A1.1 CH2CH2OH CH2CH(CH3)2 IA-366 A1.1 CH2CH2CH2OH CH2CH(CH3)2 IA-367 A1.1 CH2CH(OH)CH2OH CH2CH(CH3)2 IA-368 A1.1 CH2CH(OCH3)2 CH2CH(CH3)2 IA-369 A1.1 CH2SCH3 CH2CH(CH3)2 IA-370 A1.1 (CH2)3SCH3 CH2CH(CH3)2 IA-371 A1.1 CH2S(═O)CH3 CH2CH(CH3)2 IA-372 A1.1 CH2S(═O)2CH3 CH2CH(CH3)2 IA-373 A1.1 CH2C(═O)CH3 CH2CH(CH3)2 IA-374 A1.1 CH2C(═O)CH2CH3 CH2CH(CH3)2 IA-375 A1.1 CH2COOH CH2CH(CH3)2 IA-376 A1.1 CH2COOCH3 CH2CH(CH3)2 IA-377 A1.1 CH2COOCH2CH3 CH2CH(CH3)2 IA-378 A1.1 cyclo-C3H5 CH2CH(CH3)2 IA-379 A1.1 cyclo-C4H7 CH2CH(CH3)2 IA-380 A1.1 cyclo-C5H9 CH2CH(CH3)2 IA-381 A1.1 cyclo-C6H11 CH2CH(CH3)2 IA-382 A1.1 C6H5 CH2CH(CH3)2 IA-383 A1.1 CH(CH3)CH2CH3 CH(CH3)CH2CH3 IA-384 A1.1 CH2CHCH2 CH(CH3)CH2CH3 IA-385 A1.1 CH2CCH CH(CH3)CH2CH3 IA-386 A1.1 CH(CH3)CH═CH2 CH(CH3)CH2CH3 IA-387 A1.1 CHF2 CH(CH3)CH2CH3 IA-388 A1.1 CH2Cl CH(CH3)CH2CH3 IA-389 A1.1 CH2CH2CN CH(CH3)CH2CH3 IA-390 A1.1 CH2CH2Cl CH(CH3)CH2CH3 IA-391 A1.1 CH2CH2OH CH(CH3)CH2CH3 IA-392 A1.1 CH2CH2CH2OH CH(CH3)CH2CH3 IA-393 A1.1 CH2CH(OH)CH2OH CH(CH3)CH2CH3 IA-394 A1.1 CH2CH(OCH3)2 CH(CH3)CH2CH3 IA-395 A1.1 CH2SCH3 CH(CH3)CH2CH3 IA-396 A1.1 (CH2)3SCH3 CH(CH3)CH2CH3 IA-397 A1.1 CH2S(═O)CH3 CH(CH3)CH2CH3 IA-398 A1.1 CH2S(═O)2CH3 CH(CH3)CH2CH3 IA-399 A1.1 CH2C(═O)CH3 CH(CH3)CH2CH3 IA-400 A1.1 CH2C(═O)CH2CH3 CH(CH3)CH2CH3 IA-401 A1.1 CH2COOH CH(CH3)CH2CH3 IA-402 A1.1 CH2COOCH3 CH(CH3)CH2CH3 IA-403 A1.1 CH2COOCH2CH3 CH(CH3)CH2CH3 IA-404 A1.1 cyclo-C3H5 CH(CH3)CH2CH3 IA-405 A1.1 cyclo-C4H7 CH(CH3)CH2CH3 IA-406 A1.1 cyclo-C5H9 CH(CH3)CH2CH3 IA-407 A1.1 cyclo-C6H11 CH(CH3)CH2CH3 IA-408 A1.1 C6H5 CH(CH3)CH2CH3 IA-409 A1.1 CH2CHCH2 CH2CHCH2 IA-410 A1.1 CH2CCH CH2CHCH2 IA-411 A1.1 CH(CH3)CH═CH2 CH2CHCH2 IA-412 A1.1 CHF2 CH2CHCH2 IA-413 A1.1 CH2Cl CH2CHCH2 IA-414 A1.1 CH2CH2CN CH2CHCH2 IA-415 A1.1 CH2CH2Cl CH2CHCH2 IA-416 A1.1 CH2CH2OH CH2CHCH2 IA-417 A1.1 CH2CH2CH2OH CH2CHCH2 IA-418 A1.1 CH2CH(OH)CH2OH CH2CHCH2 IA-419 A1.1 CH2CH(OCH3)2 CH2CHCH2 IA-420 A1.1 CH2SCH3 CH2CHCH2 IA-421 A1.1 (CH2)3SCH3 CH2CHCH2 IA-422 A1.1 CH2S(═O)CH3 CH2CHCH2 IA-423 A1.1 CH2S(═O)2CH3 CH2CHCH2 IA-424 A1.1 CH2C(═O)CH3 CH2CHCH2 IA-425 A1.1 CH2C(═O)CH2CH3 CH2CHCH2 IA-426 A1.1 CH2COOH CH2CHCH2 IA-427 A1.1 CH2COOCH3 CH2CHCH2 IA-428 A1.1 CH2COOCH2CH3 CH2CHCH2 IA-429 A1.1 cyclo-C3H5 CH2CHCH2 IA-430 A1.1 cyclo-C4H7 CH2CHCH2 IA-431 A1.1 cyclo-C5H9 CH2CHCH2 IA-432 A1.1 cyclo-C6H11 CH2CHCH2 IA-433 A1.1 C6H5 CH2CHCH2 IA-434 A1.1 CH2CCH CH2CCH IA-435 A1.1 CH(CH3)CH═CH2 CH2CCH IA-436 A1.1 CHF2 CH2CCH IA-437 A1.1 CH2Cl CH2CCH IA-438 A1.1 CH2CH2CN CH2CCH IA-439 A1.1 CH2CH2Cl CH2CCH IA-440 A1.1 CH2CH2OH CH2CCH IA-441 A1.1 CH2CH2CH2OH CH2CCH IA-442 A1.1 CH2CH(OH)CH2OH CH2CCH IA-443 A1.1 CH2CH(OCH3)2 CH2CCH IA-444 A1.1 CH2SCH3 CH2CCH IA-445 A1.1 (CH2)3SCH3 CH2CCH IA-446 A1.1 CH2S(═O)CH3 CH2CCH IA-447 A1.1 CH2S(═O)2CH3 CH2CCH IA-448 A1.1 CH2C(═O)CH3 CH2CCH IA-449 A1.1 CH2C(═O)CH2CH3 CH2CCH IA-450 A1.1 CH2COOH CH2CCH IA-451 A1.1 CH2COOCH3 CH2CCH IA-452 A1.1 CH2COOCH2CH3 CH2CCH IA-453 A1.1 cyclo-C3H5 CH2CCH IA-454 A1.1 cyclo-C4H7 CH2CCH IA-455 A1.1 cyclo-C5H9 CH2CCH IA-456 A1.1 cyclo-C6H11 CH2CCH IA-457 A1.1 C6H5 CH2CCH IA-458 A1.1 CH(CH3)CH═CH2 CH(CH3)CH═CH2 IA-459 A1.1 CHF2 CH(CH3)CH═CH2 IA-460 A1.1 CH2Cl CH(CH3)CH═CH2 IA-461 A1.1 CH2CH2CN CH(CH3)CH═CH2 IA-462 A1.1 CH2CH2Cl CH(CH3)CH═CH2 IA-463 A1.1 CH2CH2OH CH(CH3)CH═CH2 IA-464 A1.1 CH2CH2CH2OH CH(CH3)CH═CH2 IA-465 A1.1 CH2CH(OH)CH2OH CH(CH3)CH═CH2 IA-466 A1.1 CH2CH(OCH3)2 CH(CH3)CH═CH2 IA-467 A1.1 CH2SCH3 CH(CH3)CH═CH2 IA-468 A1.1 (CH2)3SCH3 CH(CH3)CH═CH2 IA-469 A1.1 CH2S(═O)CH3 CH(CH3)CH═CH2 IA-470 A1.1 CH2S(═O)2CH3 CH(CH3)CH═CH2 IA-471 A1.1 CH2C(═O)CH3 CH(CH3)CH═CH2 IA-472 A1.1 CH2C(═O)CH2CH3 CH(CH3)CH═CH2 IA-473 A1.1 CH2COOH CH(CH3)CH═CH2 IA-474 A1.1 CH2COOCH3 CH(CH3)CH═CH2 IA-475 A1.1 CH2COOCH2CH3 CH(CH3)CH═CH2 IA-476 A1.1 cyclo-C3H5 CH(CH3)CH═CH2 IA-477 A1.1 cyclo-C4H7 CH(CH3)CH═CH2 IA-478 A1.1 cyclo-C5H9 CH(CH3)CH═CH2 IA-479 A1.1 cyclo-C6H11 CH(CH3)CH═CH2 IA-480 A1.1 C6H5 CH(CH3)CH═CH2 IA-481 A1.1 CHF2 CHF2 IA-482 A1.1 CH2Cl CHF2 IA-483 A1.1 CH2CH2CN CHF2 IA-484 A1.1 CH2CH2Cl CHF2 IA-485 A1.1 CH2CH2OH CHF2 IA-486 A1.1 CH2CH2CH2OH CHF2 IA-487 A1.1 CH2CH(OH)CH2OH CHF2 IA-488 A1.1 CH2CH(OCH3)2 CHF2 IA-489 A1.1 CH2SCH3 CHF2 IA-490 A1.1 (CH2)3SCH3 CHF2 IA-491 A1.1 CH2S(═O)CH3 CHF2 IA-492 A1.1 CH2S(═O)2CH3 CHF2 IA-493 A1.1 CH2C(═O)CH3 CHF2 IA-494 A1.1 CH2C(═O)CH2CH3 CHF2 IA-495 A1.1 CH2COOH CHF2 IA-496 A1.1 CH2COOCH3 CHF2 IA-497 A1.1 CH2COOCH2CH3 CHF2 IA-498 A1.1 cyclo-C3H5 CHF2 IA-499 A1.1 cyclo-C4H7 CHF2 IA-500 A1.1 cyclo-C5H9 CHF2 IA-501 A1.1 cyclo-C6H11 CHF2 IA-502 A1.1 C6H5 CHF2 IA-503 A1.1 CH2Cl CH2Cl IA-504 A1.1 CH2CH2CN CH2Cl IA-505 A1.1 CH2CH2Cl CH2Cl IA-506 A1.1 CH2CH2OH CH2Cl IA-507 A1.1 CH2CH2CH2OH CH2Cl IA-508 A1.1 CH2CH(OH)CH2OH CH2Cl IA-509 A1.1 CH2CH(OCH3)2 CH2Cl IA-510 A1.1 CH2SCH3 CH2Cl IA-511 A1.1 (CH2)3SCH3 CH2Cl IA-512 A1.1 CH2S(═O)CH3 CH2Cl IA-513 A1.1 CH2S(═O)2CH3 CH2Cl IA-514 A1.1 CH2C(═O)CH3 CH2Cl IA-515 A1.1 CH2C(═O)CH2CH3 CH2Cl IA-516 A1.1 CH2COOH CH2Cl IA-517 A1.1 CH2COOCH3 CH2Cl IA-518 A1.1 CH2COOCH2CH3 CH2Cl IA-519 A1.1 cyclo-C3H5 CH2Cl IA-520 A1.1 cyclo-C4H7 CH2Cl IA-521 A1.1 cyclo-C5H9 CH2Cl IA-522 A1.1 cyclo-C6H11 CH2Cl IA-523 A1.1 C6H5 CH2Cl IA-524 A1.1 CH2CH2CN CH2CH2CN IA-525 A1.1 CH2CH2Cl CH2CH2CN IA-526 A1.1 CH2CH2OH CH2CH2CN IA-527 A1.1 CH2CH2CH2OH CH2CH2CN IA-528 A1.1 CH2CH(OH)CH2OH CH2CH2CN IA-529 A1.1 CH2CH(OCH3)2 CH2CH2CN IA-530 A1.1 CH2SCH3 CH2CH2CN IA-531 A1.1 (CH2)3SCH3 CH2CH2CN IA-532 A1.1 CH2S(═O)CH3 CH2CH2CN IA-533 A1.1 CH2S(═O)2CH3 CH2CH2CN IA-534 A1.1 CH2C(═O)CH3 CH2CH2CN IA-535 A1.1 CH2C(═O)CH2CH3 CH2CH2CN IA-536 A1.1 CH2COOH CH2CH2CN IA-537 A1.1 CH2COOCH3 CH2CH2CN IA-538 A1.1 CH2COOCH2CH3 CH2CH2CN IA-539 A1.1 cyclo-C3H5 CH2CH2CN IA-540 A1.1 cyclo-C4H7 CH2CH2CN IA-541 A1.1 cyclo-C5H9 CH2CH2CN IA-542 A1.1 cyclo-C6H11 CH2CH2CN IA-543 A1.1 C6H5 CH2CH2CN IA-544 A1.1 CH2CH2Cl CH2CH2Cl IA-545 A1.1 CH2CH2OH CH2CH2Cl IA-546 A1.1 CH2CH2CH2OH CH2CH2Cl IA-547 A1.1 CH2CH(OH)CH2OH CH2CH2Cl IA-548 A1.1 CH2CH(OCH3)2 CH2CH2Cl IA-549 A1.1 CH2SCH3 CH2CH2Cl IA-550 A1.1 (CH2)3SCH3 CH2CH2Cl IA-551 A1.1 CH2S(═O)CH3 CH2CH2Cl IA-552 A1.1 CH2S(═O)2CH3 CH2CH2Cl IA-553 A1.1 CH2C(═O)CH3 CH2CH2Cl IA-554 A1.1 CH2C(═O)CH2CH3 CH2CH2Cl IA-555 A1.1 CH2COOH CH2CH2Cl IA-556 A1.1 CH2COOCH3 CH2CH2Cl IA-557 A1.1 CH2COOCH2CH3 CH2CH2Cl IA-558 A1.1 cyclo-C3H5 CH2CH2Cl IA-559 A1.1 cyclo-C4H7 CH2CH2Cl IA-560 A1.1 cyclo-C5H9 CH2CH2Cl IA-561 A1.1 cyclo-C6H11 CH2CH2Cl IA-562 A1.1 C6H5 CH2CH2Cl IA-563 A1.1 CH2CH2OH CH2CH2OH IA-564 A1.1 CH2CH2CH2OH CH2CH2OH IA-565 A1.1 CH2CH(OH)CH2OH CH2CH2OH IA-566 A1.1 CH2CH(OCH3)2 CH2CH2OH IA-567 A1.1 CH2SCH3 CH2CH2OH IA-568 A1.1 (CH2)3SCH3 CH2CH2OH IA-569 A1.1 CH2S(═O)CH3 CH2CH2OH IA-570 A1.1 CH2S(═O)2CH3 CH2CH2OH IA-571 A1.1 CH2C(═O)CH3 CH2CH2OH IA-572 A1.1 CH2C(═O)CH2CH3 CH2CH2OH IA-573 A1.1 CH2COOH CH2CH2OH IA-574 A1.1 CH2COOCH3 CH2CH2OH IA-575 A1.1 CH2COOCH2CH3 CH2CH2OH IA-576 A1.1 cyclo-C3H5 CH2CH2OH IA-577 A1.1 cyclo-C4H7 CH2CH2OH IA-578 A1.1 cyclo-C5H9 CH2CH2OH IA-579 A1.1 cyclo-C6H11 CH2CH2OH IA-580 A1.1 C6H5 CH2CH2OH IA-581 A1.1 CH2CH2CH2OH CH2CH2CH2OH IA-582 A1.1 CH2CH(OH)CH2OH CH2CH2CH2OH IA-583 A1.1 CH2CH(OCH3)2 CH2CH2CH2OH IA-584 A1.1 CH2SCH3 CH2CH2CH2OH IA-585 A1.1 (CH2)3SCH3 CH2CH2CH2OH IA-586 A1.1 CH2S(═O)CH3 CH2CH2CH2OH IA-587 A1.1 CH2S(═O)2CH3 CH2CH2CH2OH IA-588 A1.1 CH2C(═O)CH3 CH2CH2CH2OH IA-589 A1.1 CH2C(═O)CH2CH3 CH2CH2CH2OH IA-590 A1.1 CH2COOH CH2CH2CH2OH IA-591 A1.1 CH2COOCH3 CH2CH2CH2OH IA-592 A1.1 CH2COOCH2CH3 CH2CH2CH2OH IA-593 A1.1 cyclo-C3H5 CH2CH2CH2OH IA-594 A1.1 cyclo-C4H7 CH2CH2CH2OH IA-595 A1.1 cyclo-C5H9 CH2CH2CH2OH IA-596 A1.1 cyclo-C6H11 CH2CH2CH2OH IA-597 A1.1 C6H5 CH2CH2CH2OH IA-598 A1.1 CH2CH(OH)CH2OH CH2CH(OH)CH2OH IA-599 A1.1 CH2CH(OCH3)2 CH2CH(OH)CH2OH IA-600 A1.1 CH2SCH3 CH2CH(OH)CH2OH IA-601 A1.1 (CH2)3SCH3 CH2CH(OH)CH2OH IA-602 A1.1 CH2S(═O)CH3 CH2CH(OH)CH2OH IA-603 A1.1 CH2S(═O)2CH3 CH2CH(OH)CH2OH IA-604 A1.1 CH2C(═O)CH3 CH2CH(OH)CH2OH IA-605 A1.1 CH2C(═O)CH2CH3 CH2CH(OH)CH2OH IA-606 A1.1 CH2COOH CH2CH(OH)CH2OH IA-607 A1.1 CH2COOCH3 CH2CH(OH)CH2OH IA-608 A1.1 CH2COOCH2CH3 CH2CH(OH)CH2OH IA-609 A1.1 cyclo-C3H5 CH2CH(OH)CH2OH IA-610 A1.1 cyclo-C4H7 CH2CH(OH)CH2OH IA-611 A1.1 cyclo-C5H9 CH2CH(OH)CH2OH IA-612 A1.1 cyclo-C6H11 CH2CH(OH)CH2OH IA-613 A1.1 C6H5 CH2CH(OH)CH2OH IA-614 A1.1 CH2CH(OCH3)2 CH2CH(OCH3)2 IA-615 A1.1 CH2SCH3 CH2CH(OCH3)2 IA-616 A1.1 (CH2)3SCH3 CH2CH(OCH3)2 IA-617 A1.1 CH2S(═O)CH3 CH2CH(OCH3)2 IA-618 A1.1 CH2S(═O)2CH3 CH2CH(OCH3)2 IA-619 A1.1 CH2C(═O)CH3 CH2CH(OCH3)2 IA-620 A1.1 CH2C(═O)CH2CH3 CH2CH(OCH3)2 IA-621 A1.1 CH2COOH CH2CH(OCH3)2 IA-622 A1.1 CH2COOCH3 CH2CH(OCH3)2 IA-623 A1.1 CH2COOCH2CH3 CH2CH(OCH3)2 IA-624 A1.1 cyclo-C3H5 CH2CH(OCH3)2 IA-625 A1.1 cyclo-C4H7 CH2CH(OCH3)2 IA-626 A1.1 cyclo-C5H9 CH2CH(OCH3)2 IA-627 A1.1 cyclo-C6H11 CH2CH(OCH3)2 IA-628 A1.1 C6H5 CH2CH(OCH3)2 IA-629 A1.1 CH2SCH3 CH2SCH3 IA-630 A1.1 (CH2)3SCH3 CH2SCH3 IA-631 A1.1 CH2S(═O)CH3 CH2SCH3 IA-632 A1.1 CH2S(═O)2CH3 CH2SCH3 IA-633 A1.1 CH2C(═O)CH3 CH2SCH3 IA-634 A1.1 CH2C(═O)CH2CH3 CH2SCH3 IA-635 A1.1 CH2COOH CH2SCH3 IA-636 A1.1 CH2COOCH3 CH2SCH3 IA-637 A1.1 CH2COOCH2CH3 CH2SCH3 IA-638 A1.1 cyclo-C3H5 CH2SCH3 IA-639 A1.1 cyclo-C4H7 CH2SCH3 IA-640 A1.1 cyclo-C5H9 CH2SCH3 IA-641 A1.1 cyclo-C6H11 CH2SCH3 IA-642 A1.1 C6H5 CH2SCH3 IA-643 A1.1 (CH2)3SCH3 (CH2)3SCH3 IA-644 A1.1 CH2S(═O)CH3 (CH2)3SCH3 IA-645 A1.1 CH2S(═O)2CH3 (CH2)3SCH3 IA-646 A1.1 CH2C(═O)CH3 (CH2)3SCH3 IA-647 A1.1 CH2C(═O)CH2CH3 (CH2)3SCH3 IA-648 A1.1 CH2COOH (CH2)3SCH3 IA-649 A1.1 CH2COOCH3 (CH2)3SCH3 IA-650 A1.1 CH2COOCH2CH3 (CH2)3SCH3 IA-651 A1.1 cyclo-C3H5 (CH2)3SCH3 IA-652 A1.1 cyclo-C4H7 (CH2)3SCH3 IA-653 A1.1 cyclo-C5H9 (CH2)3SCH3 IA-654 A1.1 cyclo-C6H11 (CH2)3SCH3 IA-655 A1.1 C6H5 (CH2)3SCH3 IA-656 A1.1 CH2S(═O)CH3 CH2S(═O)CH3 IA-657 A1.1 CH2S(═O)2CH3 CH2S(═O)CH3 IA-658 A1.1 CH2C(═O)CH3 CH2S(═O)CH3 IA-659 A1.1 CH2C(═O)CH2CH3 CH2S(═O)CH3 IA-660 A1.1 CH2COOH CH2S(═O)CH3 IA-661 A1.1 CH2COOCH3 CH2S(═O)CH3 IA-662 A1.1 CH2COOCH2CH3 CH2S(═O)CH3 IA-663 A1.1 cyclo-C3H5 CH2S(═O)CH3 IA-664 A1.1 cyclo-C4H7 CH2S(═O)CH3 IA-665 A1.1 cyclo-C5H9 CH2S(═O)CH3 IA-666 A1.1 cyclo-C6H11 CH2S(═O)CH3 IA-667 A1.1 C6H5 CH2S(═O)CH3 IA-668 A1.1 CH2S(═O)2CH3 CH2S(═O)2CH3 IA-669 A1.1 CH2C(═O)CH3 CH2S(═O)2CH3 IA-670 A1.1 CH2C(═O)CH2CH3 CH2S(═O)2CH3 IA-671 A1.1 CH2COOH CH2S(═O)2CH3 IA-672 A1.1 CH2COOCH3 CH2S(═O)2CH3 IA-673 A1.1 CH2COOCH2CH3 CH2S(═O)2CH3 IA-674 A1.1 cyclo-C3H5 CH2S(═O)2CH3 IA-675 A1.1 cyclo-C4H7 CH2S(═O)2CH3 IA-676 A1.1 cyclo-C5H9 CH2S(═O)2CH3 IA-677 A1.1 cyclo-C6H11 CH2S(═O)2CH3 IA-678 A1.1 C6H5 CH2S(═O)2CH3 IA-679 A1.1 CH2C(═O)CH3 CH2C(═O)CH3 IA-680 A1.1 CH2C(═O)CH2CH3 CH2C(═O)CH3 IA-681 A1.1 CH2COOH CH2C(═O)CH3 IA-682 A1.1 CH2COOCH3 CH2C(═O)CH3 IA-683 A1.1 CH2COOCH2CH3 CH2C(═O)CH3 IA-684 A1.1 cyclo-C3H5 CH2C(═O)CH3 IA-685 A1.1 cyclo-C4H7 CH2C(═O)CH3 IA-686 A1.1 cyclo-C5H9 CH2C(═O)CH3 IA-687 A1.1 cyclo-C6H11 CH2C(═O)CH3 IA-688 A1.1 C6H5 CH2C(═O)CH3 IA-689 A1.1 CH2C(═O)CH2CH3 CH2C(═O)CH2CH3 IA-690 A1.1 CH2COOH CH2C(═O)CH2CH3 IA-691 A1.1 CH2COOCH3 CH2C(═O)CH2CH3 IA-692 A1.1 CH2COOCH2CH3 CH2C(═O)CH2CH3 IA-693 A1.1 cyclo-C3H5 CH2C(═O)CH2CH3 IA-694 A1.1 cyclo-C4H7 CH2C(═O)CH2CH3 IA-695 A1.1 cyclo-C5H9 CH2C(═O)CH2CH3 IA-696 A1.1 cyclo-C6H11 CH2C(═O)CH2CH3 IA-697 A1.1 C6H5 CH2C(═O)CH2CH3 IA-698 A1.1 CH2COOH CH2COOH IA-699 A1.1 CH2COOCH3 CH2COOH IA-700 A1.1 CH2COOCH2CH3 CH2COOH IA-701 A1.1 cyclo-C3H5 CH2COOH IA-702 A1.1 cyclo-C4H7 CH2COOH IA-703 A1.1 cyclo-C5H9 CH2COOH IA-704 A1.1 cyclo-C6H11 CH2COOH IA-705 A1.1 C6H5 CH2COOH IA-706 A1.1 CH2COOCH3 CH2COOCH3 IA-707 A1.1 CH2COOCH2CH3 CH2COOCH3 IA-708 A1.1 cyclo-C3H5 CH2COOCH3 IA-709 A1.1 cyclo-C4H7 CH2COOCH3 IA-710 A1.1 cyclo-C5H9 CH2COOCH3 IA-711 A1.1 cyclo-C6H11 CH2COOCH3 IA-712 A1.1 C6H5 CH2COOCH3 IA-713 A1.1 CH2COOCH2CH3 CH2COOCH2CH3 IA-714 A1.1 cyclo-C3H5 CH2COOCH2CH3 IA-715 A1.1 cyclo-C4H7 CH2COOCH2CH3 IA-716 A1.1 cyclo-C5H9 CH2COOCH2CH3 IA-717 A1.1 cyclo-C6H11 CH2COOCH2CH3 IA-718 A1.1 C6H5 CH2COOCH2CH3 IA-719 A1.1 cyclo-C3H5 cyclo-C3H5 IA-720 A1.1 cyclo-C4H7 cyclo-C3H5 IA-721 A1.1 cyclo-C5H9 cyclo-C3H5 IA-722 A1.1 cyclo-C6H11 cyclo-C3H5 IA-723 A1.1 C6H5 cyclo-C3H5 IA-724 A1.1 cyclo-C4H7 cyclo-C4H7 IA-725 A1.1 cyclo-C5H9 cyclo-C4H7 IA-726 A1.1 cyclo-C6H11 cyclo-C4H7 IA-727 A1.1 C6H5 cyclo-C4H7 IA-728 A1.1 cyclo-C5H9 cyclo-C5H9 IA-729 A1.1 cyclo-C6H11 cyclo-C5H9 IA-730 A1.1 C6H5 cyclo-C5H9 IA-731 A1.1 cyclo-C6H11 cyclo-C6H11 IA-732 A1.1 C6H5 cyclo-C6H11 IA-733 A1.1 C6H5 C6H5 IA-734 CH3 CH3 IA-735 A1.2 CH2CH3 CH3 IA-736 A1.2 CH═CH2 CH3 IA-737 A1.2 CH2CH2CH3 CH3 IA-738 A1.2 CH(CH3)2 CH3 IA-739 A1.2 CH2CH2CH2CH3 CH3 IA-740 A1.2 C(CH3)3 CH3 IA-741 A1.2 CH2CH(CH3)2 CH3 IA-742 A1.2 CH(CH3)CH2CH3 CH3 IA-743 A1.2 CH2CHCH2 CH3 IA-744 A1.2 CH2CCH CH3 IA-745 A1.2 CH(CH3)CH═CH2 CH3 IA-746 A1.2 CHF2 CH3 IA-747 A1.2 CH2Cl CH3 IA-748 A1.2 CH2CH2CN CH3 IA-749 A1.2 CH2CH2Cl CH3 IA-750 A1.2 CH2CH2OH CH3 IA-751 A1.2 CH2CH2CH2OH CH3 IA-752 A1.2 CH2CH(OH)CH2OH CH3 IA-753 A1.2 CH2CH(OCH3)2 CH3 IA-754 A1.2 CH2SCH3 CH3 IA-755 A1.2 (CH2)3SCH3 CH3 IA-756 A1.2 CH2S(═O)CH3 CH3 IA-757 A1.2 CH2S(═O)2CH3 CH3 IA-758 A1.2 CH2C(═O)CH3 CH3 IA-759 A1.2 CH2C(═O)CH2CH3 CH3 IA-760 A1.2 CH2COOH CH3 IA-761 A1.2 CH2COOCH3 CH3 IA-762 A1.2 CH2COOCH2CH3 CH3 IA-763 A1.2 cyclo-C3H5 CH3 IA-764 A1.2 cyclo-C4H7 CH3 IA-765 A1.2 cyclo-C5H9 CH3 IA-766 A1.2 cyclo-C6H11 CH3 IA-767 A1.2 C6H5 CH3 IA-768 A1.2 CH2CH3 CH2CH3 IA-769 A1.2 CH═CH2 CH2CH3 IA-770 A1.2 CH2CH2CH3 CH2CH3 IA-771 A1.2 CH(CH3)2 CH2CH3 IA-772 A1.2 CH2CH2CH2CH3 CH2CH3 IA-773 A1.2 C(CH3)3 CH2CH3 IA-774 A1.2 CH2CH(CH3)2 CH2CH3 IA-775 A1.2 CH(CH3)CH2CH3 CH2CH3 IA-776 A1.2 CH2CHCH2 CH2CH3 IA-777 A1.2 CH2CCH CH2CH3 IA-778 A1.2 CH(CH3)CH═CH2 CH2CH3 IA-779 A1.2 CHF2 CH2CH3 IA-780 A1.2 CH2Cl CH2CH3 IA-781 A1.2 CH2CH2CN CH2CH3 IA-782 A1.2 CH2CH2Cl CH2CH3 IA-783 A1.2 CH2CH2OH CH2CH3 IA-784 A1.2 CH2CH2CH2OH CH2CH3 IA-785 A1.2 CH2CH(OH)CH2OH CH2CH3 IA-786 A1.2 CH2CH(OCH3)2 CH2CH3 IA-787 A1.2 CH2SCH3 CH2CH3 IA-788 A1.2 (CH2)3SCH3 CH2CH3 IA-789 A1.2 CH2S(═O)CH3 CH2CH3 IA-790 A1.2 CH2S(═O)2CH3 CH2CH3 IA-791 A1.2 CH2C(═O)CH3 CH2CH3 IA-792 A1.2 CH2C(═O)CH2CH3 CH2CH3 IA-793 A1.2 CH2COOH CH2CH3 IA-794 A1.2 CH2COOCH3 CH2CH3 IA-795 A1.2 CH2COOCH2CH3 CH2CH3 IA-796 A1.2 cyclo-C3H5 CH2CH3 IA-797 A1.2 cyclo-C4H7 CH2CH3 IA-798 A1.2 cyclo-C5H9 CH2CH3 IA-799 A1.2 cyclo-C6H11 CH2CH3 IA-800 A1.2 C6H5 CH2CH3 IA-801 A1.2 CH═CH2 CH═CH2 IA-802 A1.2 CH2CH2CH3 CH═CH2 IA-803 A1.2 CH(CH3)2 CH═CH2 IA-804 A1.2 CH2CH2CH2CH3 CH═CH2 IA-805 A1.2 C(CH3)3 CH═CH2 IA-806 A1.2 CH2CH(CH3)2 CH═CH2 IA-807 A1.2 CH(CH3)CH2CH3 CH═CH2 IA-808 A1.2 CH2CHCH2 CH═CH2 IA-809 A1.2 CH2CCH CH═CH2 IA-810 A1.2 CH(CH3)CH═CH2 CH═CH2 IA-811 A1.2 CHF2 CH═CH2 IA-812 A1.2 CH2Cl CH═CH2 IA-813 A1.2 CH2CH2CN CH═CH2 IA-814 A1.2 CH2CH2Cl CH═CH2 IA-815 A1.2 CH2CH2OH CH═CH2 IA-816 A1.2 CH2CH2CH2OH CH═CH2 IA-817 A1.2 CH2CH(OH)CH2OH CH═CH2 IA-818 A1.2 CH2CH(OCH3)2 CH═CH2 IA-819 A1.2 CH2SCH3 CH═CH2 IA-820 A1.2 (CH2)3SCH3 CH═CH2 IA-821 A1.2 CH2S(═O)CH3 CH═CH2 IA-822 A1.2 CH2S(═O)2CH3 CH═CH2 IA-823 A1.2 CH2C(═O)CH3 CH═CH2 IA-824 A1.2 CH2C(═O)CH2CH3 CH═CH2 IA-825 A1.2 CH2COOH CH═CH2 IA-826 A1.2 CH2COOCH3 CH═CH2 IA-827 A1.2 CH2COOCH2CH3 CH═CH2 IA-828 A1.2 cyclo-C3H5 CH═CH2 IA-829 A1.2 cyclo-C4H7 CH═CH2 IA-830 A1.2 cyclo-C5H9 CH═CH2 IA-831 A1.2 cyclo-C6H11 CH═CH2 IA-832 A1.2 C6H5 CH═CH2 IA-833 A1.2 CH2CH2CH3 CH2CH2CH3 IA-834 A1.2 CH(CH3)2 CH2CH2CH3 IA-835 A1.2 CH2CH2CH2CH3 CH2CH2CH3 IA-836 A1.2 C(CH3)3 CH2CH2CH3 IA-837 A1.2 CH2CH(CH3)2 CH2CH2CH3 IA-838 A1.2 CH(CH3)CH2CH3 CH2CH2CH3 IA-839 A1.2 CH2CHCH2 CH2CH2CH3 IA-840 A1.2 CH2CCH CH2CH2CH3 IA-841 A1.2 CH(CH3)CH═CH2 CH2CH2CH3 IA-842 A1.2 CHF2 CH2CH2CH3 IA-843 A1.2 CH2Cl CH2CH2CH3 IA-844 A1.2 CH2CH2CN CH2CH2CH3 IA-845 A1.2 CH2CH2Cl CH2CH2CH3 IA-846 A1.2 CH2CH2OH CH2CH2CH3 IA-847 A1.2 CH2CH2CH2OH CH2CH2CH3 IA-848 A1.2 CH2CH(OH)CH2OH CH2CH2CH3 IA-849 A1.2 CH2CH(OCH3)2 CH2CH2CH3 IA-850 A1.2 CH2SCH3 CH2CH2CH3 IA-851 A1.2 (CH2)3SCH3 CH2CH2CH3 IA-852 A1.2 CH2S(═O)CH3 CH2CH2CH3 IA-853 A1.2 CH2S(═O)2CH3 CH2CH2CH3 IA-854 A1.2 CH2C(═O)CH3 CH2CH2CH3 IA-855 A1.2 CH2C(═O)CH2CH3 CH2CH2CH3 IA-856 A1.2 CH2COOH CH2CH2CH3 IA-857 A1.2 CH2COOCH3 CH2CH2CH3 IA-858 A1.2 CH2COOCH2CH3 CH2CH2CH3 IA-859 A1.2 cyclo-C3H5 CH2CH2CH3 IA-860 A1.2 cyclo-C4H7 CH2CH2CH3 IA-861 A1.2 cyclo-C5H9 CH2CH2CH3 IA-862 A1.2 cyclo-C6H11 CH2CH2CH3 IA-863 A1.2 C6H5 CH2CH2CH3 IA-864 A1.2 CH(CH3)2 CH(CH3)2 IA-865 A1.2 CH2CH2CH2CH3 CH(CH3)2 IA-866 A1.2 C(CH3)3 CH(CH3)2 IA-867 A1.2 CH2CH(CH3)2 CH(CH3)2 IA-868 A1.2 CH(CH3)CH2CH3 CH(CH3)2 IA-869 A1.2 CH2CHCH2 CH(CH3)2 IA-870 A1.2 CH2CCH CH(CH3)2 IA-871 A1.2 CH(CH3)CH═CH2 CH(CH3)2 IA-872 A1.2 CHF2 CH(CH3)2 IA-873 A1.2 CH2Cl CH(CH3)2 IA-874 A1.2 CH2CH2CN CH(CH3)2 IA-875 A1.2 CH2CH2Cl CH(CH3)2 IA-876 A1.2 CH2CH2OH CH(CH3)2 IA-877 A1.2 CH2CH2CH2OH CH(CH3)2 IA-878 A1.2 CH2CH(OH)CH2OH CH(CH3)2 IA-879 A1.2 CH2CH(OCH3)2 CH(CH3)2 IA-880 A1.2 CH2SCH3 CH(CH3)2 IA-881 A1.2 (CH2)3SCH3 CH(CH3)2 IA-882 A1.2 CH2S(═O)CH3 CH(CH3)2 IA-883 A1.2 CH2S(═O)2CH3 CH(CH3)2 IA-884 A1.2 CH2C(═O)CH3 CH(CH3)2 IA-885 A1.2 CH2C(═O)CH2CH3 CH(CH3)2 IA-886 A1.2 CH2COOH CH(CH3)2 IA-887 A1.2 CH2COOCH3 CH(CH3)2 IA-888 A1.2 CH2COOCH2CH3 CH(CH3)2 IA-889 A1.2 cyclo-C3H5 CH(CH3)2 IA-890 A1.2 cyclo-C4H7 CH(CH3)2 IA-891 A1.2 cyclo-C5H9 CH(CH3)2 IA-892 A1.2 cyclo-C6H11 CH(CH3)2 IA-893 A1.2 C6H5 CH(CH3)2 IA-894 A1.2 CH2CH2CH2CH3 CH2CH2CH2CH3 IA-895 A1.2 C(CH3)3 CH2CH2CH2CH3 IA-896 A1.2 CH2CH(CH3)2 CH2CH2CH2CH3 IA-897 A1.2 CH(CH3)CH2CH3 CH2CH2CH2CH3 IA-898 A1.2 CH2CHCH2 CH2CH2CH2CH3 IA-899 A1.2 CH2CCH CH2CH2CH2CH3 IA-900 A1.2 CH(CH3)CH═CH2 CH2CH2CH2CH3 IA-901 A1.2 CHF2 CH2CH2CH2CH3 IA-902 A1.2 CH2Cl CH2CH2CH2CH3 IA-903 A1.2 CH2CH2CN CH2CH2CH2CH3 IA-904 A1.2 CH2CH2Cl CH2CH2CH2CH3 IA-905 A1.2 CH2CH2OH CH2CH2CH2CH3 IA-906 A1.2 CH2CH2CH2OH CH2CH2CH2CH3 IA-907 A1.2 CH2CH(OH)CH2OH CH2CH2CH2CH3 IA-908 A1.2 CH2CH(OCH3)2 CH2CH2CH2CH3 IA-909 A1.2 CH2SCH3 CH2CH2CH2CH3 IA-910 A1.2 (CH2)3SCH3 CH2CH2CH2CH3 IA-911 A1.2 CH2S(═O)CH3 CH2CH2CH2CH3 IA-912 A1.2 CH2S(═O)2CH3 CH2CH2CH2CH3 IA-913 A1.2 CH2C(═O)CH3 CH2CH2CH2CH3 IA-914 A1.2 CH2C(═O)CH2CH3 CH2CH2CH2CH3 IA-915 A1.2 CH2COOH CH2CH2CH2CH3 IA-916 A1.2 CH2COOCH3 CH2CH2CH2CH3 IA-917 A1.2 CH2COOCH2CH3 CH2CH2CH2CH3 IA-918 A1.2 cyclo-C3H5 CH2CH2CH2CH3 IA-919 A1.2 cyclo-C4H7 CH2CH2CH2CH3 IA-920 A1.2 cyclo-C5H9 CH2CH2CH2CH3 IA-921 A1.2 cyclo-C6H11 CH2CH2CH2CH3 IA-922 A1.2 C6H5 CH2CH2CH2CH3 IA-923 A1.2 C(CH3)3 C(CH3)3 IA-924 A1.2 CH2CH(CH3)2 C(CH3)3 IA-925 A1.2 CH(CH3)CH2CH3 C(CH3)3 IA-926 A1.2 CH2CHCH2 C(CH3)3 IA-927 A1.2 CH2CCH C(CH3)3 IA-928 A1.2 CH(CH3)CH═CH2 C(CH3)3 IA-929 A1.2 CHF2 C(CH3)3 IA-930 A1.2 CH2Cl C(CH3)3 IA-931 A1.2 CH2CH2CN C(CH3)3 IA-932 A1.2 CH2CH2Cl C(CH3)3 IA-933 A1.2 CH2CH2OH C(CH3)3 IA-934 A1.2 CH2CH2CH2OH C(CH3)3 IA-935 A1.2 CH2CH(OH)CH2OH C(CH3)3 IA-936 A1.2 CH2CH(OCH3)2 C(CH3)3 IA-937 A1.2 CH2SCH3 C(CH3)3 IA-938 A1.2 (CH2)3SCH3 C(CH3)3 IA-939 A1.2 CH2S(═O)CH3 C(CH3)3 IA-940 A1.2 CH2S(═O)2CH3 C(CH3)3 IA-941 A1.2 CH2C(═O)CH3 C(CH3)3 IA-942 A1.2 CH2C(═O)CH2CH3 C(CH3)3 IA-943 A1.2 CH2COOH C(CH3)3 IA-944 A1.2 CH2COOCH3 C(CH3)3 IA-945 A1.2 CH2COOCH2CH3 C(CH3)3 IA-946 A1.2 cyclo-C3H5 C(CH3)3 IA-947 A1.2 cyclo-C4H7 C(CH3)3 IA-948 A1.2 cyclo-C5H9 C(CH3)3 IA-949 A1.2 cyclo-C6H11 C(CH3)3 IA-950 A1.2 C6H5 C(CH3)3 IA-951 A1.2 CH2CH(CH3)2 CH2CH(CH3)2 IA-952 A1.2 CH(CH3)CH2CH3 CH2CH(CH3)2 IA-953 A1.2 CH2CHCH2 CH2CH(CH3)2 IA-954 A1.2 CH2CCH CH2CH(CH3)2 IA-955 A1.2 CH(CH3)CH═CH2 CH2CH(CH3)2 IA-956 A1.2 CHF2 CH2CH(CH3)2 IA-957 A1.2 CH2Cl CH2CH(CH3)2 IA-958 A1.2 CH2CH2CN CH2CH(CH3)2 IA-959 A1.2 CH2CH2Cl CH2CH(CH3)2 IA-960 A1.2 CH2CH2OH CH2CH(CH3)2 IA-961 A1.2 CH2CH2CH2OH CH2CH(CH3)2 IA-962 A1.2 CH2CH(OH)CH2OH CH2CH(CH3)2 IA-963 A1.2 CH2CH(OCH3)2 CH2CH(CH3)2 IA-964 A1.2 CH2SCH3 CH2CH(CH3)2 IA-965 A1.2 (CH2)3SCH3 CH2CH(CH3)2 IA-966 A1.2 CH2S(═O)CH3 CH2CH(CH3)2 IA-967 A1.2 CH2S(═O)2CH3 CH2CH(CH3)2 IA-968 A1.2 CH2C(═O)CH3 CH2CH(CH3)2 IA-969 A1.2 CH2C(═O)CH2CH3 CH2CH(CH3)2 IA-970 A1.2 CH2COOH CH2CH(CH3)2 IA-971 A1.2 CH2COOCH3 CH2CH(CH3)2 IA-972 A1.2 CH2COOCH2CH3 CH2CH(CH3)2 IA-973 A1.2 cyclo-C3H5 CH2CH(CH3)2 IA-974 A1.2 cyclo-C4H7 CH2CH(CH3)2 IA-975 A1.2 cyclo-C5H9 CH2CH(CH3)2 IA-976 A1.2 cyclo-C6H11 CH2CH(CH3)2 IA-977 A1.2 C6H5 CH2CH(CH3)2 IA-978 A1.2 CH(CH3)CH2CH3 CH(CH3)CH2CH3 IA-979 A1.2 CH2CHCH2 CH(CH3)CH2CH3 IA-980 A1.2 CH2CCH CH(CH3)CH2CH3 IA-981 A1.2 CH(CH3)CH═CH2 CH(CH3)CH2CH3 IA-982 A1.2 CHF2 CH(CH3)CH2CH3 IA-983 A1.2 CH2Cl CH(CH3)CH2CH3 IA-984 A1.2 CH2CH2CN CH(CH3)CH2CH3 IA-985 A1.2 CH2CH2Cl CH(CH3)CH2CH3 IA-986 A1.2 CH2CH2OH CH(CH3)CH2CH3 IA-987 A1.2 CH2CH2CH2OH CH(CH3)CH2CH3 IA-988 A1.2 CH2CH(OH)CH2OH CH(CH3)CH2CH3 IA-989 A1.2 CH2CH(OCH3)2 CH(CH3)CH2CH3 IA-990 A1.2 CH2SCH3 CH(CH3)CH2CH3 IA-991 A1.2 (CH2)3SCH3 CH(CH3)CH2CH3 IA-992 A1.2 CH2S(═O)CH3 CH(CH3)CH2CH3 IA-993 A1.2 CH2S(═O)2CH3 CH(CH3)CH2CH3 IA-994 A1.2 CH2C(═O)CH3 CH(CH3)CH2CH3 IA-995 A1.2 CH2C(═O)CH2CH3 CH(CH3)CH2CH3 IA-996 A1.2 CH2COOH CH(CH3)CH2CH3 IA-997 A1.2 CH2COOCH3 CH(CH3)CH2CH3 IA-998 A1.2 CH2COOCH2CH3 CH(CH3)CH2CH3 IA-999 A1.2 cyclo-C3H5 CH(CH3)CH2CH3 IA-1000 A1.2 cyclo-C4H7 CH(CH3)CH2CH3 IA-1001 A1.2 cyclo-C5H9 CH(CH3)CH2CH3 IA-1002 A1.2 cyclo-C6H11 CH(CH3)CH2CH3 IA-1003 A1.2 C6H5 CH(CH3)CH2CH3 IA-1004 A1.2 CH2CHCH2 CH2CHCH2 IA-1005 A1.2 CH2CCH CH2CHCH2 IA-1006 A1.2 CH(CH3)CH═CH2 CH2CHCH2 IA-1007 A1.2 CHF2 CH2CHCH2 IA-1008 A1.2 CH2Cl CH2CHCH2 IA-1009 A1.2 CH2CH2CN CH2CHCH2 IA-1010 A1.2 CH2CH2Cl CH2CHCH2 IA-1011 A1.2 CH2CH2OH CH2CHCH2 IA-1012 A1.2 CH2CH2CH2OH CH2CHCH2 IA-1013 A1.2 CH2CH(OH)CH2OH CH2CHCH2 IA-1014 A1.2 CH2CH(OCH3)2 CH2CHCH2 IA-1015 A1.2 CH2SCH3 CH2CHCH2 IA-1016 A1.2 (CH2)3SCH3 CH2CHCH2 IA-1017 A1.2 CH2S(═O)CH3 CH2CHCH2 IA-1018 A1.2 CH2S(═O)2CH3 CH2CHCH2 IA-1019 A1.2 CH2C(═O)CH3 CH2CHCH2 IA-1020 A1.2 CH2C(═O)CH2CH3 CH2CHCH2 IA-1021 A1.2 CH2COOH CH2CHCH2 IA-1022 A1.2 CH2COOCH3 CH2CHCH2 IA-1023 A1.2 CH2COOCH2CH3 CH2CHCH2 IA-1024 A1.2 cyclo-C3H5 CH2CHCH2 IA-1025 A1.2 cyclo-C4H7 CH2CHCH2 IA-1026 A1.2 cyclo-C5H9 CH2CHCH2 IA-1027 A1.2 cyclo-C6H11 CH2CHCH2 IA-1028 A1.2 C6H5 CH2CHCH2 IA-1029 A1.2 CH2CCH CH2CCH IA-1030 A1.2 CH(CH3)CH═CH2 CH2CCH IA-1031 A1.2 CHF2 CH2CCH IA-1032 A1.2 CH2Cl CH2CCH IA-1033 A1.2 CH2CH2CN CH2CCH IA-1034 A1.2 CH2CH2Cl CH2CCH IA-1035 A1.2 CH2CH2OH CH2CCH IA-1036 A1.2 CH2CH2CH2OH CH2CCH IA-1037 A1.2 CH2CH(OH)CH2OH CH2CCH IA-1038 A1.2 CH2CH(OCH3)2 CH2CCH IA-1039 A1.2 CH2SCH3 CH2CCH IA-1040 A1.2 (CH2)3SCH3 CH2CCH IA-1041 A1.2 CH2S(═O)CH3 CH2CCH IA-1042 A1.2 CH2S(═O)2CH3 CH2CCH IA-1043 A1.2 CH2C(═O)CH3 CH2CCH IA-1044 A1.2 CH2C(═O)CH2CH3 CH2CCH IA-1045 A1.2 CH2COOH CH2CCH IA-1046 A1.2 CH2COOCH3 CH2CCH IA-1047 A1.2 CH2COOCH2CH3 CH2CCH IA-1048 A1.2 cyclo-C3H5 CH2CCH IA-1049 A1.2 cyclo-C4H7 CH2CCH IA-1050 A1.2 cyclo-C5H9 CH2CCH IA-1051 A1.2 cyclo-C6H11 CH2CCH IA-1052 A1.2 C6H5 CH2CCH IA-1053 A1.2 CH(CH3)CH═CH2 CH(CH3)CH═CH2 IA-1054 A1.2 CHF2 CH(CH3)CH═CH2 IA-1055 A1.2 CH2Cl CH(CH3)CH═CH2 IA-1056 A1.2 CH2CH2CN CH(CH3)CH═CH2 IA-1057 A1.2 CH2CH2Cl CH(CH3)CH═CH2 IA-1058 A1.2 CH2CH2OH CH(CH3)CH═CH2 IA-1059 A1.2 CH2CH2CH2OH CH(CH3)CH═CH2 IA-1060 A1.2 CH2CH(OH)CH2OH CH(CH3)CH═CH2 IA-1061 A1.2 CH2CH(OCH3)2 CH(CH3)CH═CH2 IA-1062 A1.2 CH2SCH3 CH(CH3)CH═CH2 IA-1063 A1.2 (CH2)3SCH3 CH(CH3)CH═CH2 IA-1064 A1.2 CH2S(═O)CH3 CH(CH3)CH═CH2 IA-1065 A1.2 CH2S(═O)2CH3 CH(CH3)CH═CH2 IA-1066 A1.2 CH2C(═O)CH3 CH(CH3)CH═CH2 IA-1067 A1.2 CH2C(═O)CH2CH3 CH(CH3)CH═CH2 IA-1068 A1.2 CH2COOH CH(CH3)CH═CH2 IA-1069 A1.2 CH2COOCH3 CH(CH3)CH═CH2 IA-1070 A1.2 CH2COOCH2CH3 CH(CH3)CH═CH2 IA-1071 A1.2 cyclo-C3H5 CH(CH3)CH═CH2 IA-1072 A1.2 cyclo-C4H7 CH(CH3)CH═CH2 IA-1073 A1.2 cyclo-C5H9 CH(CH3)CH═CH2 IA-1074 A1.2 cyclo-C6H11 CH(CH3)CH═CH2 IA-1075 A1.2 C6H5 CH(CH3)CH═CH2 IA-1076 A1.2 CHF2 CHF2 IA-1077 A1.2 CH2Cl CHF2 IA-1078 A1.2 CH2CH2CN CHF2 IA-1079 A1.2 CH2CH2Cl CHF2 IA-1080 A1.2 CH2CH2OH CHF2 IA-1081 A1.2 CH2CH2CH2OH CHF2 IA-1082 A1.2 CH2CH(OH)CH2OH CHF2 IA-1083 A1.2 CH2CH(OCH3)2 CHF2 IA-1084 A1.2 CH2SCH3 CHF2 IA-1085 A1.2 (CH2)3SCH3 CHF2 IA-1086 A1.2 CH2S(═O)CH3 CHF2 IA-1087 A1.2 CH2S(═O)2CH3 CHF2 IA-1088 A1.2 CH2C(═O)CH3 CHF2 IA-1089 A1.2 CH2C(═O)CH2CH3 CHF2 IA-1090 A1.2 CH2COOH CHF2 IA-1091 A1.2 CH2COOCH3 CHF2 IA-1092 A1.2 CH2COOCH2CH3 CHF2 IA-1093 A1.2 cyclo-C3H5 CHF2 IA-1094 A1.2 cyclo-C4H7 CHF2 IA-1095 A1.2 cyclo-C5H9 CHF2 IA-1096 A1.2 cyclo-C6H11 CHF2 IA-1097 A1.2 C6H5 CHF2 IA-1098 A1.2 CH2Cl CH2Cl IA-1099 A1.2 CH2CH2CN CH2Cl IA-1100 A1.2 CH2CH2Cl CH2Cl IA-1101 A1.2 CH2CH2OH CH2Cl IA-1102 A1.2 CH2CH2CH2OH CH2Cl IA-1103 A1.2 CH2CH(OH)CH2OH CH2Cl IA-1104 A1.2 CH2CH(OCH3)2 CH2Cl IA-1105 A1.2 CH2SCH3 CH2Cl IA-1106 A1.2 (CH2)3SCH3 CH2Cl IA-1107 A1.2 CH2S(═O)CH3 CH2Cl IA-1108 A1.2 CH2S(═O)2CH3 CH2Cl IA-1109 A1.2 CH2C(═O)CH3 CH2Cl IA-1110 A1.2 CH2C(═O)CH2CH3 CH2Cl IA-1111 A1.2 CH2COOH CH2Cl IA-1112 A1.2 CH2COOCH3 CH2Cl IA-1113 A1.2 CH2COOCH2CH3 CH2Cl IA-1114 A1.2 cyclo-C3H5 CH2Cl IA-1115 A1.2 cyclo-C4H7 CH2Cl IA-1116 A1.2 cyclo-C5H9 CH2Cl IA-1117 A1.2 cyclo-C6H11 CH2Cl IA-1118 A1.2 C6H5 CH2Cl IA-1119 A1.2 CH2CH2CN CH2CH2CN IA-1120 A1.2 CH2CH2Cl CH2CH2CN IA-1121 A1.2 CH2CH2OH CH2CH2CN IA-1122 A1.2 CH2CH2CH2OH CH2CH2CN IA-1123 A1.2 CH2CH(OH)CH2OH CH2CH2CN IA-1124 A1.2 CH2CH(OCH3)2 CH2CH2CN IA-1125 A1.2 CH2SCH3 CH2CH2CN IA-1126 A1.2 (CH2)3SCH3 CH2CH2CN IA-1127 A1.2 CH2S(═O)CH3 CH2CH2CN IA-1128 A1.2 CH2S(═O)2CH3 CH2CH2CN IA-1129 A1.2 CH2C(═O)CH3 CH2CH2CN IA-1130 A1.2 CH2C(═O)CH2CH3 CH2CH2CN IA-1131 A1.2 CH2COOH CH2CH2CN IA-1132 A1.2 CH2COOCH3 CH2CH2CN IA-1133 A1.2 CH2COOCH2CH3 CH2CH2CN IA-1134 A1.2 cyclo-C3H5 CH2CH2CN IA-1135 A1.2 cyclo-C4H7 CH2CH2CN IA-1136 A1.2 cyclo-C5H9 CH2CH2CN IA-1137 A1.2 cyclo-C6H11 CH2CH2CN IA-1138 A1.2 C6H5 CH2CH2CN IA-1139 A1.2 CH2CH2Cl CH2CH2Cl IA-1140 A1.2 CH2CH2OH CH2CH2Cl IA-1141 A1.2 CH2CH2CH2OH CH2CH2Cl IA-1142 A1.2 CH2CH(OH)CH2OH CH2CH2Cl IA-1143 A1.2 CH2CH(OCH3)2 CH2CH2Cl IA-1144 A1.2 CH2SCH3 CH2CH2Cl IA-1145 A1.2 (CH2)3SCH3 CH2CH2Cl IA-1146 A1.2 CH2S(═O)CH3 CH2CH2Cl IA-1147 A1.2 CH2S(═O)2CH3 CH2CH2Cl IA-1148 A1.2 CH2C(═O)CH3 CH2CH2Cl IA-1149 A1.2 CH2C(═O)CH2CH3 CH2CH2Cl IA-1150 A1.2 CH2COOH CH2CH2Cl IA-1151 A1.2 CH2COOCH3 CH2CH2Cl IA-1152 A1.2 CH2COOCH2CH3 CH2CH2Cl IA-1153 A1.2 cyclo-C3H5 CH2CH2Cl IA-1154 A1.2 cyclo-C4H7 CH2CH2Cl IA-1155 A1.2 cyclo-C5H9 CH2CH2Cl IA-1156 A1.2 cyclo-C6H11 CH2CH2Cl IA-1157 A1.2 C6H5 CH2CH2Cl IA-1158 A1.2 CH2CH2OH CH2CH2OH IA-1159 A1.2 CH2CH2CH2OH CH2CH2OH IA-1160 A1.2 CH2CH(OH)CH2OH CH2CH2OH IA-1161 A1.2 CH2CH(OCH3)2 CH2CH2OH IA-1162 A1.2 CH2SCH3 CH2CH2OH IA-1163 A1.2 (CH2)3SCH3 CH2CH2OH IA-1164 A1.2 CH2S(═O)CH3 CH2CH2OH IA-1165 A1.2 CH2S(═O)2CH3 CH2CH2OH IA-1166 A1.2 CH2C(═O)CH3 CH2CH2OH IA-1167 A1.2 CH2C(═O)CH2CH3 CH2CH2OH IA-1168 A1.2 CH2COOH CH2CH2OH IA-1169 A1.2 CH2COOCH3 CH2CH2OH IA-1170 A1.2 CH2COOCH2CH3 CH2CH2OH IA-1171 A1.2 cyclo-C3H5 CH2CH2OH IA-1172 A1.2 cyclo-C4H7 CH2CH2OH IA-1173 A1.2 cyclo-C5H9 CH2CH2OH IA-1174 A1.2 cyclo-C6H11 CH2CH2OH IA-1175 A1.2 C6H5 CH2CH2OH IA-1176 A1.2 CH2CH2CH2OH CH2CH2CH2OH IA-1177 A1.2 CH2CH(OH)CH2OH CH2CH2CH2OH IA-1178 A1.2 CH2CH(OCH3)2 CH2CH2CH2OH IA-1179 A1.2 CH2SCH3 CH2CH2CH2OH IA-1180 A1.2 (CH2)3SCH3 CH2CH2CH2OH IA-1181 A1.2 CH2S(═O)CH3 CH2CH2CH2OH IA-1182 A1.2 CH2S(═O)2CH3 CH2CH2CH2OH IA-1183 A1.2 CH2C(═O)CH3 CH2CH2CH2OH IA-1184 A1.2 CH2C(═O)CH2CH3 CH2CH2CH2OH IA-1185 A1.2 CH2COOH CH2CH2CH2OH IA-1186 A1.2 CH2COOCH3 CH2CH2CH2OH IA-1187 A1.2 CH2COOCH2CH3 CH2CH2CH2OH IA-1188 A1.2 cyclo-C3H5 CH2CH2CH2OH IA-1189 A1.2 cyclo-C4H7 CH2CH2CH2OH IA-1190 A1.2 cyclo-C5H9 CH2CH2CH2OH IA-1191 A1.2 cyclo-C6H11 CH2CH2CH2OH IA-1192 A1.2 C6H5 CH2CH2CH2OH IA-1193 A1.2 CH2CH(OH)CH2OH CH2CH(OH)CH2OH IA-1194 A1.2 CH2CH(OCH3)2 CH2CH(OH)CH2OH IA-1195 A1.2 CH2SCH3 CH2CH(OH)CH2OH IA-1196 A1.2 (CH2)3SCH3 CH2CH(OH)CH2OH IA-1197 A1.2 CH2S(═O)CH3 CH2CH(OH)CH2OH IA-1198 A1.2 CH2S(═O)2CH3 CH2CH(OH)CH2OH IA-1199 A1.2 CH2C(═O)CH3 CH2CH(OH)CH2OH IA-1200 A1.2 CH2C(═O)CH2CH3 CH2CH(OH)CH2OH IA-1201 A1.2 CH2COOH CH2CH(OH)CH2OH IA-1202 A1.2 CH2COOCH3 CH2CH(OH)CH2OH IA-1203 A1.2 CH2COOCH2CH3 CH2CH(OH)CH2OH IA-1204 A1.2 cyclo-C3H5 CH2CH(OH)CH2OH IA-1205 A1.2 cyclo-C4H7 CH2CH(OH)CH2OH IA-1206 A1.2 cyclo-C5H9 CH2CH(OH)CH2OH IA-1207 A1.2 cyclo-C6H11 CH2CH(OH)CH2OH IA-1208 A1.2 C6H5 CH2CH(OH)CH2OH IA-1209 A1.2 CH2CH(OCH3)2 CH2CH(OCH3)2 IA-1210 A1.2 CH2SCH3 CH2CH(OCH3)2 IA-1211 A1.2 (CH2)3SCH3 CH2CH(OCH3)2 IA-1212 A1.2 CH2S(═O)CH3 CH2CH(OCH3)2 IA-1213 A1.2 CH2S(═O)2CH3 CH2CH(OCH3)2 IA-1214 A1.2 CH2C(═O)CH3 CH2CH(OCH3)2 IA-1215 A1.2 CH2C(═O)CH2CH3 CH2CH(OCH3)2 IA-1216 A1.2 CH2COOH CH2CH(OCH3)2 IA-1217 A1.2 CH2COOCH3 CH2CH(OCH3)2 IA-1218 A1.2 CH2COOCH2CH3 CH2CH(OCH3)2 IA-1219 A1.2 cyclo-C3H5 CH2CH(OCH3)2 IA-1220 A1.2 cyclo-C4H7 CH2CH(OCH3)2 IA-1221 A1.2 cyclo-C5H9 CH2CH(OCH3)2 IA-1222 A1.2 cyclo-C6H11 CH2CH(OCH3)2 IA-1223 A1.2 C6H5 CH2CH(OCH3)2 IA-1224 A1.2 CH2SCH3 CH2SCH3 IA-1225 A1.2 (CH2)3SCH3 CH2SCH3 IA-1226 A1.2 CH2S(═O)CH3 CH2SCH3 IA-1227 A1.2 CH2S(═O)2CH3 CH2SCH3 IA-1228 A1.2 CH2C(═O)CH3 CH2SCH3 IA-1229 A1.2 CH2C(═O)CH2CH3 CH2SCH3 IA-1230 A1.2 CH2COOH CH2SCH3 IA-1231 A1.2 CH2COOCH3 CH2SCH3 IA-1232 A1.2 CH2COOCH2CH3 CH2SCH3 IA-1233 A1.2 cyclo-C3H5 CH2SCH3 IA-1234 A1.2 cyclo-C4H7 CH2SCH3 IA-1235 A1.2 cyclo-C5H9 CH2SCH3 IA-1236 A1.2 cyclo-C6H11 CH2SCH3 IA-1237 A1.2 C6H5 CH2SCH3 IA-1238 A1.2 (CH2)3SCH3 (CH2)3SCH3 IA-1239 A1.2 CH2S(═O)CH3 (CH2)3SCH3 IA-1240 A1.2 CH2S(═O)2CH3 (CH2)3SCH3 IA-1241 A1.2 CH2C(═O)CH3 (CH2)3SCH3 IA-1242 A1.2 CH2C(═O)CH2CH3 (CH2)3SCH3 IA-1243 A1.2 CH2COOH (CH2)3SCH3 IA-1244 A1.2 CH2COOCH3 (CH2)3SCH3 IA-1245 A1.2 CH2COOCH2CH3 (CH2)3SCH3 IA-1246 A1.2 cyclo-C3H5 (CH2)3SCH3 IA-1247 A1.2 cyclo-C4H7 (CH2)3SCH3 IA-1248 A1.2 cyclo-C5H9 (CH2)3SCH3 IA-1249 A1.2 cyclo-C6H11 (CH2)3SCH3 IA-1250 A1.2 C6H5 (CH2)3SCH3 IA-1251 A1.2 CH2S(═O)CH3 CH2S(═O)CH3 IA-1252 A1.2 CH2S(═O)2CH3 CH2S(═O)CH3 IA-1253 A1.2 CH2C(═O)CH3 CH2S(═O)CH3 IA-1254 A1.2 CH2C(═O)CH2CH3 CH2S(═O)CH3 IA-1255 A1.2 CH2COOH CH2S(═O)CH3 IA-1256 A1.2 CH2COOCH3 CH2S(═O)CH3 IA-1257 A1.2 CH2COOCH2CH3 CH2S(═O)CH3 IA-1258 A1.2 cyclo-C3H5 CH2S(═O)CH3 IA-1259 A1.2 cyclo-C4H7 CH2S(═O)CH3 IA-1260 A1.2 cyclo-C5H9 CH2S(═O)CH3 IA-1261 A1.2 cyclo-C6H11 CH2S(═O)CH3 IA-1262 A1.2 C6H5 CH2S(═O)CH3 IA-1263 A1.2 CH2S(═O)2CH3 CH2S(═O)2CH3 IA-1264 A1.2 CH2C(═O)CH3 CH2S(═O)2CH3 IA-1265 A1.2 CH2C(═O)CH2CH3 CH2S(═O)2CH3 IA-1266 A1.2 CH2COOH CH2S(═O)2CH3 IA-1267 A1.2 CH2COOCH3 CH2S(═O)2CH3 IA-1268 A1.2 CH2COOCH2CH3 CH2S(═O)2CH3 IA-1269 A1.2 cyclo-C3H5 CH2S(═O)2CH3 IA-1270 A1.2 cyclo-C4H7 CH2S(═O)2CH3 IA-1271 A1.2 cyclo-C5H9 CH2S(═O)2CH3 IA-1272 A1.2 cyclo-C6H11 CH2S(═O)2CH3 IA-1273 A1.2 C6H5 CH2S(═O)2CH3 IA-1274 A1.2 CH2C(═O)CH3 CH2C(═O)CH3 IA-1275 A1.2 CH2C(═O)CH2CH3 CH2C(═O)CH3 IA-1276 A1.2 CH2COOH CH2C(═O)CH3 IA-1277 A1.2 CH2COOCH3 CH2C(═O)CH3 IA-1278 A1.2 CH2COOCH2CH3 CH2C(═O)CH3 IA-1279 A1.2 cyclo-C3H5 CH2C(═O)CH3 IA-1280 A1.2 cyclo-C4H7 CH2C(═O)CH3 IA-1281 A1.2 cyclo-C5H9 CH2C(═O)CH3 IA-1282 A1.2 cyclo-C6H11 CH2C(═O)CH3 IA-1283 A1.2 C6H5 CH2C(═O)CH3 IA-1284 A1.2 CH2C(═O)CH2CH3 CH2C(═O)CH2CH3 IA-1285 A1.2 CH2COOH CH2C(═O)CH2CH3 IA-1286 A1.2 CH2COOCH3 CH2C(═O)CH2CH3 IA-1287 A1.2 CH2COOCH2CH3 CH2C(═O)CH2CH3 IA-1288 A1.2 cyclo-C3H5 CH2C(═O)CH2CH3 IA-1289 A1.2 cyclo-C4H7 CH2C(═O)CH2CH3 IA-1290 A1.2 cyclo-C5H9 CH2C(═O)CH2CH3 IA-1291 A1.2 cyclo-C6H11 CH2C(═O)CH2CH3 IA-1292 A1.2 C6H5 CH2C(═O)CH2CH3 IA-1293 A1.2 CH2COOH CH2COOH IA-1294 A1.2 CH2COOCH3 CH2COOH IA-1295 A1.2 CH2COOCH2CH3 CH2COOH IA-1296 A1.2 cyclo-C3H5 CH2COOH IA-1297 A1.2 cyclo-C4H7 CH2COOH IA-1298 A1.2 cyclo-C5H9 CH2COOH IA-1299 A1.2 cyclo-C6H11 CH2COOH IA-1300 A1.2 C6H5 CH2COOH IA-1301 A1.2 CH2COOCH3 CH2COOCH3 IA-1302 A1.2 CH2COOCH2CH3 CH2COOCH3 IA-1303 A1.2 cyclo-C3H5 CH2COOCH3 IA-1304 A1.2 cyclo-C4H7 CH2COOCH3 IA-1305 A1.2 cyclo-C5H9 CH2COOCH3 IA-1306 A1.2 cyclo-C6H11 CH2COOCH3 IA-1307 A1.2 C6H5 CH2COOCH3 IA-1308 A1.2 CH2COOCH2CH3 CH2COOCH2CH3 IA-1309 A1.2 cyclo-C3H5 CH2COOCH2CH3 IA-1310 A1.2 cyclo-C4H7 CH2COOCH2CH3 IA-1311 A1.2 cyclo-C5H9 CH2COOCH2CH3 IA-1312 A1.2 cyclo-C6H11 CH2COOCH2CH3 IA-1313 A1.2 C6H5 CH2COOCH2CH3 IA-1314 A1.2 cyclo-C3H5 cyclo-C3H5 IA-1315 A1.2 cyclo-C4H7 cyclo-C3H5 IA-1316 A1.2 cyclo-C5H9 cyclo-C3H5 IA-1317 A1.2 cyclo-C6H11 cyclo-C3H5 IA-1318 A1.2 C6H5 cyclo-C3H5 IA-1319 A1.2 cyclo-C4H7 cyclo-C4H7 IA-1320 A1.2 cyclo-C5H9 cyclo-C4H7 IA-1321 A1.2 cyclo-C6H11 cyclo-C4H7 IA-1322 A1.2 C6H5 cyclo-C4H7 IA-1323 A1.2 cyclo-C5H9 cyclo-C5H9 IA-1324 A1.2 cyclo-C6H11 cyclo-C5H9 IA-1325 A1.2 C6H5 cyclo-C5H9 IA-1326 A1.2 cyclo-C6H11 cyclo-C6H11 IA-1327 A1.2 C6H5 cyclo-C6H11 IA-1328 A1.2 C6H5 C6H5
- wherein
- Q1 denotes hydrogen, chlorine, bromine, fluorine or cyano;
- Q3 denotes CF3 or bromine; and
- A in each case corresponds to a row of the Table below,
- and/or an enantiomer, a salt, and/or an N-oxide thereof.
7: The compound of claim 6, wherein Re and Rf each independently are CH3, CH2CH3, CH2CH2CH3 or CH(CH3)2.
8: The compound of claim 6,
- wherein
- Q1 denotes chlorine;
- Q3 denotes CF3;
- and/or an enantiomer, a salt, and/or an N-oxide thereof.
9: The compound of claim 8, wherein Re and Rf are CH2CH3.
10: The compound of claim 8, wherein Re and Rf are CH(CH3)2.
11: The compound of claim 6,
- wherein
- Q1 denotes cyano;
- Q3 denotes CF3;
- and/or an enantiomer, a salt, and/or an N-oxide thereof.
12: The compound of claim 11, wherein Re and Rf are CH(CH3)2.
13: A method for the control of insects, acarids or nematodes by contacting the insect, acarid or nematode or their food supply, habitat, breeding ground or their locus with a pesticidally effective amount of compound of formula I as defined in claim 2.
14: A method for the control of insects, acarids or nematodes by contacting the insect, acarid or nematode or their food supply, habitat, breeding ground or their locus with a pesticidally effective amount of a compound of formula I as defined in claim 6.
15: A method for the control of insects, acarids or nematodes by contacting the insect, acarid or nematode or their food supply, habitat, breeding ground or their locus with a pesticidally effective amount of a compound of formula I as defined in claim 7.
16: A method for the control of insects, acarids or nematodes by contacting the insect, acarid or nematode or their food supply, habitat, breeding ground or their locus with a pesticidally effective amount of a compound of formula I as defined in claim 8.
17: A method for the control of insects, acarids or nematodes by contacting the insect, acarid or nematode or their food supply, habitat, breeding ground or their locus with a pesticidally effective amount of a compound of formula I as defined in claim 9.
18: A method for the control of insects, acarids or nematodes by contacting the insect, acarid or nematode or their food supply, habitat, breeding ground or their locus with a pesticidally effective amount of a compound of formula I as defined in claim 10.
19: A method for the control of insects, acarids or nematodes by contacting the insect, acarid or nematode or their food supply, habitat, breeding ground or their locus with a pesticidally effective amount of a compound of formula I as defined in claim 11.
20: A method for the control of insects, acarids or nematodes by contacting the insect, acarid or nematode or their food supply, habitat, breeding ground or their locus with a pesticidally effective amount of a compound of formula I as defined in claim 12.
Type: Application
Filed: Jun 13, 2016
Publication Date: Jan 19, 2017
Inventors: Thomas SCHMIDT (Neustadt), Michael PUHL (Lampertheim), Joachim DICKHAUT (Heidelberg), Henricus Maria Martinus BASTIAANS (Usingen), Michael RACK (Eppelheim), Deborah L. CULBERTSON (Fuquay Varina, NC), Douglas D. ANSPAUGH (Apex, NC), Franz-Josef BRAUN (Durham, NC), Toni BUCCI (Fuquay Varina, NC), Henry Van Tuyl COTTER (Raleigh, NC), David G. KUHN (Apex, NC), Hassan OLOUMI-SADEGHI (Raleigh, NC)
Application Number: 15/180,628