Herbicidal heterocycles

Compounds of Formula (1), their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation, wherein A, R1, R2a, R2b, W, Y, and Z are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (1) and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula (1).

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Description
FIELD OF THE INVENTION

This invention relates to certain pyrazoles and pyrazolines, their N-oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesired vegetation.

BACKGROUND OF THE INVENTION

The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Uncontrolled weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. For example, many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different modes of action.

World Patent Publication 95/33719 discloses compounds of Formula i as herbicides

wherein, inter alia,

A is an aromatic ring system;

R1 is H or C1-C10 alkyl;

R2 and R3 are independently H or C1-C4 alkyl;

W is O or S;

X is O, S or CR4R5;

Y is O, S, NR6 or CR4R5; and

Z is O, S or NR4.

However, it does not disclose the compounds of the present invention.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula 1 including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation:

  • wherein:
    • A is an optionally substituted aryl or heteroaromatic ring, wherein the optional substituents are selected from halogen, cyano, C1-C6 alkyl, C1-C4 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, OR8, —S(O)kR9, —C(O)R10, —C(O)OR11 and —C(O)NR12R13; two substituents of the group A may combine to form a fused 5- or 6-membered saturated or partially saturated carbocyclic or heterocyclic ring, and said fused ring system is optionally substituted with one or more R7;
    • Y is O or S;
    • Z is O, S(O)n or CR3R4;
    • W is (CR3R4)q;
    • R1 is H, C1-C12 alkyl C1-C2 haloalkyl, C3-C12 cycloalkyl C3-C12 halocycloalkyl C4-C12 alkylcycloalkyl, C4-C12 alkylhalocycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, di-(C1-C2 alkyl)amino, Cl, Br, I, —C(O)R5, —C(O)OR5, —C(O)NR5R6 or tri(C1-C4 alkyl)silyl;
    • R2a is H, C1-C4 alkyl or C1-C4 haloalkyl; and R2a only exists when the carbon atom to which it is connected is a quaternary carbon center in which case the dotted line in Formula 1, together with the parallel solid line, represents a single bond;
    • R2b is H, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, F or Cl; or
    • R1 and R2b are taken together as —C(R3R4)CH2CH2—, —C(R3R4)CH2CH2CH2— or —(CH2)mO(CH2)t—;
    • each R3 and R4 are independently H, C1-C6 alkyl or C1-C6 haloalkyl;
    • R5 is C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alynyl, C3-C6 cycloalkyl or C1-C6 haloalkyl;
    • R6 is H or C1-C6 alkyl;
    • each R7 is independently C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, halogen, CN, NO2 or hydroxy,
    • each R8 is independently C1-C4 alkyl or C1-C4 haloalkyl;
    • each R9 is independently C1-C4 alkyl or C1-C4 haloalkyl;
    • each R10 is independently C1-C4 alkyl or C1-C4 haloalkyl;
    • each R11 is independently C1-C4 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C3 haloalkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C3-C5 halocycloalkyl, C3-C6 cycloalkenyl or C4-C6 cycloalkylalkyl;
    • each R12 is independently H or C1-C2 alkyl;
    • each R13 is independently C1-C4 alkyl; or
    • R12 and R13 are taken together as —(CH2)4—, —(CH2)5— or —(CH2)2O(CH2)2—;
    • each k is independently 0, 1 or 2;
    • n is 0, 1 or 2;
    • q is 1 or 2;
    • m is 0, 1 or 2;
    • t is 0, 1 or 2; and
    • m+t is 2 or 3;
    • provided that:
  • (a) each position on the aryl or heteroaromatic ring A vicinal (ortho) to the point of attachment of the aryl or heteroaromatic ring to the Formula 1 backbone is independently substituted with fluorine or not substituted;
  • (b) when A is a phenyl ring with a fluorine substituent meta to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone, then attached at the other meta position of the phenyl ring is a substituent other than fluorine;
  • (c) when A is a phenyl ring with at least one —C(O)NR12R13 substituent, then the at least one —C(O)NR12R13 substituent is at a position other than meta to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone;
  • (d) when A is a phenyl ring, the position para to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone is unsubstituted or substituted by a substituent other than alkoxy;
  • (e) when A is a phenyl ring with a —C(O)OR11 substituent at the position para to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone, then a substituent is attached to a position on the phenyl ring meta to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone;
  • (f) when A is a pyridine ring connected at the 2-position to the remainder of the Formula 1 backbone and methyl is at the 6-position of the pyridine ring, then the pyridine ring is substituted at the 4-position;
  • (g) when A is a pyrimidine ring connected at the 2-position to the remainder of the Formula 1 backbone, and when the 4-position of the pyrimidine ring is unsubstituted or is substituted with methyl, then the substituent at the 6-position of the pyrimidine ring is other than methyl, and when a methoxy substituent is at the 4-position of the pyrimidine ring, then the substituent at the 6-position of the pyrimidine ring is other than methoxy,
  • (h) when A is an isothiazole ring connected at the 5-position to the remainder of the Formula 1 backbone, then the isothiazole ring is substituted with a substituent other than alkyl;
  • (i) when R1 is a C3-C12 alkoxy group, then the alkyl moiety of the alkoxy group is branched at the carbon atom attached to the oxygen atom;
  • (j) when R1 and R2b are taken together as —C(R3R4)CH2CH2—, —C(R3R4)CH2CH2CH2— or —(CH2)mO(CH2)t— then Z is O or CR3R4; and
  • (k) when R2b is connected to a quaternary carbon center, then R2b is H, C1-C4 alkyl or C1-C4 haloalkyl.

More particularly, this invention pertains to a compound of Formula 1, including all geometric and stereoisomers, an N-oxide or an agriculturally suitable salt thereof. This invention also relates to a herbicidal composition comprising a herbicidally effective amount of a compound of Formula 1 and at least one of a surfactant, a solid diluent or a liquid diluent. This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of Formula 1 (e.g., as a composition described herein).

DETAILS OF THE INVENTION

In the above recitations the term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. The term “1-2 alkyl” indicates that one or two of the available positions for that substituent may be alkyl. “Alkenyl” includes straight-chain or branched alkenes such as 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynes such as 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. “Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. “Saturated Carbocyclic” ring denotes a ring having a backbone consisting of carbon atoms linked to one another by single bonds; unless otherwise specified, the remaining carbon valences are occupied by hydrogen atoms.

The term “halogen”, either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F3C, ClCH2, CF3CH2 and CF3CCl2. The terms “haloalkenyl”, “haloalkynyl”, “haloalkoxy”, and the like, are defined analogously to the term “haloalkyl”. Examples of “haloalkenyl” include (Cl)2C═CHCH2 and CF3CH2CH═CHCH2. Examples of “haloalkynyl” include HC≡CCHCl, CF3C≡C, CCl3C≡C and FCH2C≡CCH2. Examples of “haloalkoxy” include CF3O, CCl3CH2O, HCF2CH2CH2O and CF3CH2O.

The total number of carbon atoms in a substituent group is indicated by the “Ci-Cj” prefix where i and j are numbers from 1 to 12. For example, C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when a compound of Formula 1 contains a heterocyclic ring, all substituents are attached to this ring through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

When a group contains a substituent which can be hydrogen, for example R3, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When a variable group is shown to be optionally attached to a position, for example (R15)p1 wherein p1 may be 0, then hydrogen may be at the position even if not recited in the variable group definition. When a position on a group is said to be “not substituted” or “unsubstituted”, then hydrogen atoms are attached to take up any free valency.

Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.

According to commonly accepted definition, the terms “aryl” and “aryl ring” denote a phenyl or benzene ring subject to optional substitution. The term “carbocyclic ring” denotes a ring wherein the atoms forming the ring backbone are selected only from carbon. The term “heteroaromatic ring” denotes a heterocyclic ring wherein each of the ring atoms is essentially in the same plane and has a p-orbital perpendicular to the ring plane, and in which (4n+2) π electrons, where n is 0 or a positive integer, are associated with the ring to comply with Hückel's Rule. The term “heterocyclic ring” denotes a ring wherein the atoms forming the ring backbone are selected from not only carbon but also heteroatoms such as oxygen, sulfur and nitrogen. For sake of illustration, heteroaromatic rings include, but are not limited to, furan, thiophene, pyrrole, pyrazole, imidazole, oxazole, thiazole, isoxazole, isothiazole, pyridine, pyridazine, pyrimidine, pyrazine and 1,3,5-triazine. The heterocyclic ring can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

The aryl or heteroaromatic ring of radical A of Formula 1 is optionally substituted by one or more substituents selected from halogen, cyano, C1-C6 alkyl, C1-C4 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, OR8, —S(O)kR9, —C(O)R10, —C(O)OR11 and —C(O)NR12R13. Furthermore for the purpose of defining the scope of the invention, by removing in effect one hydrogen radical from each of two substituent groups, the groups may be combined to form a saturated or partially saturated 5 or 6-membered ring fused to the aforementioned aryl or heteroaromatic ring, and said fused ring system is optionally substituted with one or more R7. For example, removing one hydrogen from each methyl of A-14 allows combination to form the fused dihydrofuran ring of A-56.

One skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N-oxides, as oxidation to the oxide requires an available lone electron pair on the nitrogen atom; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-19, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 139-151, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.

The salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.

Preferred for reason of better activity and/or ease of synthesis are compounds of Formula 1 above, geometric and stereoisomers thereof, N-oxides thereof and agriculturally suitable salts thereof, wherein the dotted line in Formula 1, together with the parallel solid line, represents a double bond.

For reason of better activity and/or ease of synthesis, certain substituent groups in Formula 1 are preferred. Y is preferably O. Z is preferably O, S or CH2. W is preferably CH2. R1 is preferably C1-C12 alkyl or C3-C12 cycloalkyl. More preferably, R1 is C3-C12 alkyl, preferably branched, or C3-C8 cycloalkyl. Even more preferably, R1 is branched C3-C6 alkyl or C4-C6 cycloalkyl. Most preferably, R1 is isopropyl, tert-butyl, sec-butyl (—CH(CH3)(CH2CH3)) or 3-pentyl (—CH(CH2CH3)2). R2a is preferably H. R2b is preferably H or C1-C4 alkyl. More preferably, R2b is H. A is preferably substituted phenyl or 5 or 6-membered heterocyclic ring comprising 0-3 nitrogen atoms, 0-1 oxygen atoms and 0-1 sulfur atoms in said ring. More preferably, A is A1, A2, A3, A4, A5, A6, A7 or A8 as depicted:
wherein

    • R14 is H, halogen, cyano, C1-C6 alkyl, C1-C4 haloalkyl, OR8, —S(O)kR9, —C(O)R10, —C(O)OR11 or —C(O)NR12R13; such that R14 is bound to a ring atom joined through one intervening ring atom to the ring atom linking the ring to the remainder of Formula 1;
    • each R15 is independently halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C1-C4 haloalkoxy; or
    • R14 taken together with an adjacent R15 is —(CH2)3—, —(CH2)4—, —O(CH2)2—, —O(CH2)3—, —S(CH2)2— or —S(CH2)3—, each optionally substituted with 1-3 substituents selected from CH3, CH2CH3 and F;
    • Y1 is O, S or N—H; such that when Y1 is N—H, the H of N—H may be replaced by an R14 or R15 substituent selected from alkyl, or the H of N—H may be replaced by the bond linking the ring to the remainder of Formula 1;
    • p1 is 0, 1, 2 or 3;
    • p2 is 0, 1 or 2;
    • p3 is 0 or 1;
    • provided that at least one R14 or R15 is other than H.

Preferably, A is A1, A2, A3, A4 or A6 wherein Y1 is O or S. More preferably, A is A1, A2 or A6 wherein Y1 is O or S. Most preferably, A is A1, A2 or A6 wherein Y1 is S. Preferably R14 is halogen, cyano, C1-C6 alkyl, C1-C4 haloalkyl, OR8, —S(O)kR9, —C(O)R10 or —C(O)OR11; and R15 is halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C1-C4 haloalkoxy, or R14 taken together with an adjacent R15 is —(CH2)3—, —(CH2)4—, —O(CH2)2—, —O(CH2)3—, —S(CH2)2— or —S(CH2)3—, each optionally substituted with 1-3 substituents selected from CH3, CH2CH3 and F; such that the left-hand bond is connected at the R14 position and the right-hand bond is connected at the R15 position. More preferably, R14 is halogen, C1-C6 alkyl, C1-C4 haloalkyl, OR8, —S(O)kR9, —C(O)R10 or —C(O)OR11. Even more preferably, R14 is Br, C1-C6 alkyl, CF2H, CF3, C1-C4 alkoxy, OCF3, OCF2H, —C(O)R10 or —C(O)OR11. Most preferably, R14 is Br, C1-C5 alkyl, CF2H, CF3, C1-C4 alkoxy, OCF3, OCF2H or —C(O)OCH3. Preferably, p1 is 0 or 1, p2 is 0 or 1 and p3 is 0 or 1. More preferably, R15 is halogen, C1-C2 alkyl or C1-C2 alkoxy. Even more preferably, R15 is C1-C6 alkyl or halogen. Most preferably, R15 is CH3, F, Cl or Br, or p1 is 0, p2 is 0 and p3 is 0, and when R15 is CH3, Cl or Br, it is preferably bound to a ring atom joined through two intervening ring atoms to the ring atom linking the ring to the remainder of Formula 1; for example, when A is A1, R15 being CH3 is preferably in the para position. k is preferably 0. R10 is preferably C1-C2 alkyl, and most preferably CH3. R11 is preferably C1-C2 alkyl, and most preferably CH3. R12 is preferably CH3. R13 is preferably CH3.

Compounds of the invention illustrating groups preferred for reasons of better activity and/or ease of synthesis are:

    • Preferred A. A compound of Formula 1 above, geometric and stereoisomers thereof, N-oxides thereof, and agriculturally suitable salts thereof of, wherein the optional substituents on A are selected from halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C1-C4 haloalkoxy; two or more substituents of the group A may combine to form a fused 5 or 6-membered saturated or partially saturated carbocyclic or heterocyclic ring, and said ring system is optionally substituted with one or more R7; and R1 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C9 cycloalkyl C3-C9 halocycloalkyl, C3-C12 alkylcycloalkyl, C3-C12 alkylhalocycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, Cl, Br, I, —C(O)R5, —C(O)OR5, —C(O)NR5R6 or trialkylsilane.
    • Preferred B. A compound of Formula 1 above, geometric and stereoisomers thereof, N-oxides thereof, and agriculturally suitable salts thereof, wherein A is substituted phenyl or 5 or 6-membered heterocyclic ring comprising 0-3 nitrogen atoms, 0-1 oxygen atoms and 0-1 sulfur atoms in said ring.
    • Preferred B1. A compound of Preferred B wherein
      • A is A1, A2, A3, A4, A5, A6, A7 or A8;
      • R14 is H, halogen, cyano, C1-C6 alkyl, C1-C4 haloalkyl, OR8, —S(O)kR9, —C(O)R10 or —C(O)OR11; such that R4 is bound to a ring atom joined through one intervening ring atom to the ring atom linking the ring to the remainder of Formula 1;
      • each R15 is independently halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C1-C4 haloalkoxy, or
      • R14 taken together with an adjacent R15 is —(CH2)3—, —(CH2)4—, —O(CH2)2—, —O(CH2)3—, —S(CH2)2— or —S(CH2)3—, each optionally substituted with 1-3 substituents selected from CH3, CH2CH3 and F;
      • Y1 is O, S or N—H; such that when Y1 is N—H, an alkyl R14 or R15 substituent or the linking bond may replace H of N—H;
      • p1 is 0, 1, 2 or 3;
      • p2 is 0, 1 or 2;
      • p3 is 0 or 1;
      • provided that at least one R14 or R15 is other than H.
    • Preferred B2. A compound of Preferred B1 wherein
      • Y is O;
      • Z is O, S or CH2;
      • W is CH2;
      • R1 is C1-C12 alkyl or C3-C12 cycloalkyl;
      • R2a is H; and
      • R2b is H or C1-C4 alkyl.
    • Preferred B3. A compound of Preferred B2 wherein
      • the dotted line in Formula 1, together with the parallel solid line, represents a double bond; and
      • R2b is H.
    • Preferred B4. A compound of Preferred B3 wherein
      • A is A1, A2 or A6;
      • Y1 is O or S;
      • R14 is halogen, C1-C6 alkyl, C1-C4 haloalkyl, OR8, —S(O)kR9, —C(O)R10 or —C(O)OR11;
      • R15 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C1-C4 haloalkoxy;
      • or R14 taken together with an adjacent R15 is —(CH2)3—, —(CH2)4—, —O(CH2)2—, —O(CH2)3—, —S(CH2)2—, —S(CH2)3—, each optionally substituted with 1-2 CH3, CH2CH3 or F; such that the left-hand bond is connected at the R14 position and the right-hand bond is connected at the R15 position;
      • p1 is 0 or 1; and
      • p2 is 0 or 1.
    • Preferred B5. A compound of Preferred B4 wherein
      • R1 is branched C3-C8 alkyl or C4-C6 cycloalkyl.
    • Preferred B6. A compound of Preferred B5 wherein
      • R1 is isopropyl, tert-butyl, sec-butyl or 3-pentyl.
    • Preferred B7. A compound of Preferred B4 wherein
      • Y1 is S;
      • R14 is Br, C1-C6 alkyl, CF2H, CF3, C1-C4 alkoxy, OCF3, OCF2H, —C(O)R10 or —C(O)OR11;
      • R15 is halogen, C1-C2 alkyl or C1-C2 alkoxy,
      • R10 is C1-q alkyl; and
      • R11 is C1-C2 alkyl.
    • Preferred B8. A compound of Preferred B7 wherein
      • R14 is Br, C1-C5 alkyl, CF2H, CF3, C1-C4 alkoxy, OCF3, OCF2H, or —C(O)OCH3;
    • Preferred B9. A compound of Preferred B8 wherein
      • R15 is C1-C2 alkyl.
    • Preferred B10. A compound of Preferred B9 wherein
      • p1 is 0 and
      • p2 is 0.
    • Preferred B11. A compound of Preferred B4 wherein
      • R15 is CH3.
    • Preferred B12. A compound of Preferred B11 wherein
      • p1 is 0; and
      • p2 is 0.
    • Preferred B13. A compound of Preferred B4 wherein
      • A is A1;
      • R14 is C1-C4 alkoxy,
      • R15 is CH3, F, Cl or Br and is in the para position relative to the bond connecting A to the remainder of Formula 1; and
      • p1 is 1.
    • Preferred B14. A compound of Preferred B5 wherein
      • A is selected from
      • R14 is OCH3 or OCH2CH3;
      • R15 is F, Cl or Br,
      • p1 is 0 or 1; and
      • R1 is CH(CH3)2, CH(CH3)(C2H5), C(CH3)3, CH(C2H5)2 or CH(CH3)(CH2CH2CH3).

Specifically preferred is a compound of Formula 1 selected from the group consisting of:

  • (a) 5-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone;
  • (b) 3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone;
  • (c) 5-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone;
  • (d) 3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-1-(3-methoxy-4-methylphenyl)-2-pyrrolidinone;
  • (e) 5-[3-(1-methylpropyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone; and
  • (f) 5-[3-(1-ethylpropyl)-1H-pyrazol-1-yl]-3-[3-trifluoromethyl)phenyl]-4-oxazolidinone;
  • (g) 1-(4-chloro-3-methoxyphenyl)-3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-2-pyrrolidinone; and
  • (h) 1-(4-chloro-3-methoxyphenyl)-3-[3-(1-ethylpropyl)-1H-pyrazol-1-yl]-2-pyrrolidinone.

The preferred compositions of the present invention and the preferred methods of use are those involving the above preferred compounds. Compounds of the invention are particularly useful for selective control of weeds in maize (corn) and/or rice crops.

Compounds of the Formula 1 can be readily prepared by one skilled in the art by using the reactions and techniques described in Scheme 1 to Scheme 4 below. In cases where a substituent of the starting material is not compatible with the reaction conditions described for any of the reaction schemes, the substituent can be converted to a protected form prior to the described reaction scheme and then deprotected after the reaction using commonly accepted protection/deprotection techniques (see Green, T. W and Wuts, P. G., Protecting Groups in Organic Transformations, 3rd Edition, John Wiley and Sons, New York, 1999). Otherwise, alternative approaches known to one skilled in the art are available. The definitions of A, R1, R2a, R2b, W, Y, and Z in compounds of Formulae 1-4 below are as defined in the Summary of the Invention.

As shown in Scheme 1, a compound of Formula 1 wherein Y is O can be prepared by contacting a compound of Formula 2 with 1-2 molar equivalents of a compound of Formula 3 in the presence of 1-1.5 molar equivalents of a dialkyl azodicarboxylate such as diethyl azodicarboxylate and 1-2 molar equivalents of a triarylphosphine such as triphenylphosphine.
The reaction is carried out in an inert solvent such as diethyl ether, tetrahydrofuran, methylene chloride, toluene or xylene at temperatures between −20 and 110° C., and preferably from −10° C. to ambient temperatures. The reaction time ranges from 1 hour to 4 days. The compound of Formula 1 is isolated using conventional purification methods such as extraction, concentration, chromatography and crystallization.

As shown in Scheme 2, a compound of Formula 1 wherein Y is O and Z is O or S can also be prepared by contacting a compound of Formula 2 wherein Z is O or S with a mixture prepared by mixing 1-2.5 molar equivalents of a compound of Formula 3, 1-2.5 molar equivalents of thionyl chloride and 2-5 molar equivalents of diisopropylethylamine in an inert solvent such as methylene chloride, tetrahydrofuran, diethyl ether, toluene or xylene.
The reaction is carried out at temperatures between −20 and 110° C. and preferably from 0° C. to ambient temperature. The reaction time ranges from 1 hour to 5 days. The compound of Formula 1 is isolated using conventional purification methods.

Alternatively as shown in Scheme 3, a compound of Formula 1 wherein Y is O is prepared by contacting a compound of Formula 4 with a compound of Formula 3 in the presence of a base such as N,N-diisopropylethylamine, NaH or KOC(CH3)3 or an excess of the compound of Formula 3.

(wherein X is CL Br, I, OSO2CH3 or OSO2(4-Me-Ph))

The reaction is carried out by adding 1 molar equivalent of a compound of Formula 4 to a mixture of 1-2.5 molar equivalents of a compound of Formula 3 in an inert solvent such as diethyl ether, tetrahydro furan, methylene chloride, N,N-dimethylformamide or toluene under N2 at ambient temperature. When less than about 2 molar equivalents of the Formula 3 compound is used, then about 0.5-2.5 molar equivalents of an additional base such as N,N-diisopropylethylamine, NaH or KOC(CH3)3 is optionally included in the Formula 3 mixture before addition of the Formula 4 compound. After the addition, the reaction mixture is stirred at temperatures between about −20 to 110° C., and preferably from about −10° C. to around 90° C. for a period of time ranging from 1 hour to 4 days. The reaction mixture is then poured into an excess amount of water and the aqueous layer is extracted with ethyl acetate between one to three times. The organic layers are separated from the aqueous layers, then combined and dried over a drying agent such as MgSO4 or Na2SO4 and subsequently concentrated. The residue is purified by conventional techniques such as column chromatography over silica gel with eluents such as solutions of ethyl acetate and hexanes in various ratios or solutions of methylene chloride and hexanes in various ratios to give the desired compounds of Formula 1 wherein Y is O.

As shown in Scheme 4, a compound of Formula 1 wherein Y is S is prepared by treating a compound of Formula 1 wherein Y is O with Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide) or P2S5 using methods or slight modification thereof taught in: Heterocycles 1995, 40(1), 271-8; J. Med. Chem. 1990, 33(10), 2697-706; Synthesis 1989, (5), 396-7; J. Chem. Soc., Perkin Trans. 1 1988, (7), 1663-8; Tetrahedron 1988, 44(10), 3025-36; and J. Org. Chem. 1988, 53(6), 1323-6.

Compounds of Formula 2 and Formula 4 are known in the art. Useful methods for their synthesis are compiled in European Patent Publication 0200415-A1 and World Patent Publications 94/13652, 95/33719, 97/19920, 97/20838, 97/28138 and 00/21928, and references cited therein.

Compounds of Formula 3 are either commercially available or can be prepared by one skilled in the art using literature methods or with slight modification thereof. Some examples of the above-mentioned literature methods are published in: A. R. Katritzky & C. W. Rees (editors), Comprehensive Heterocyclic Chemistry, (1984) Vol. 5, 167-304; Arnold Weissberger (editor), Heterocyclic Compounds, (1967), Vol. 22, 3-278; Chin. Chem. Lett. 1998, 9(9), 803-804; Synthesis 1998, (11), 1645-1654; Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1995, 34B(9), 811-15; European Patent Number 546420; J. Indian Chem. Soc. 1991, 68(5), 281-4; J. Heterocycl. Chem. 1990, 27(2), 205-8; Synth. Commun. 1989, 19(18), 3159-68; Synthesis 1989, (4), 320-1; J. Chem. Soc., Perkin Trans. 1 1987, (4), 885-97; J. Chem. Soc., Perkin Trans. 1 1985, (10), 2177-84; J. Org. Chem. 1986, 51(12), 2366-8; J. Chem. Soc., Perkin Trans. 1 1994, (4), 461-70; Heterocycles 1986, 24(2), 289-96; Tetrahedron Lett. 1998, 39(20), 3287-3290; Synthesis 1997, (3), 337-341; J. Am. Chem. Soc. 1993, 115(3), 1153-4; Heterocycles 1986, 24(4), 1075-8; Synthesis 1997, (10), 1140-1142; Tetrahedron Lett. 1996, 37(7), 1095-6; Synth. Commun. 1995, 25(5), 761-74; J. Org. Chen. 1988, 53(24), 5685-9; Heterocycles 1986, 24(4), 1075-8; and Synthesis 1985, (6-7), 690-1.

It is recognized that some reagents and reaction conditions described may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences into the synthesis will aid in obtaining the desired products. The use and choice of protecting groups will be apparent to one skilled in chemical synthesis.

One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula 1.

One skilled in the art will also recognize that compounds of Formula 1 and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. 1H NMR spectra are reported in ppm downfield from tetramethylsilane; s=singlet, d=doublet, t=triplet, q=quartet, m=multiplet, dd=doublet of doublets, dt=doublet of triplets, br s=broad singlet.

EXAMPLE 1 Preparation of 5-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone

To tetrahydrofuran (15 mL) at about −10° C. stirred under a nitrogen atmosphere were added diethyl azodicarboxylate (0.66 mL, 4.18 mmol), 5-hydroxy-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone (1 g, 3.8 mmol), 3-(1,1-dimethylethyl)-1H-pyrazole (0.48 g, 3.8 mmol) and triphenylphosphine (1.2 g, 4.41 mmol). After the addition, the reaction mixture was allowed to warm up to room temperature, and stirred overnight under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue taken into a small amount of methylene chloride and then filtered. The filtrate was loaded on silica gel in a medium pressure liquid chromatography column and eluted with a solution of 20% ethyl acetate and 80% hexanes followed by a solution of 33% ethyl acetate and 67% hexanes to give 0.26 g of a crude product. The crude product was further purified by medium pressure liquid chromatography (silica gel, 9% ethyl acetate/91% hexanes) to afford the title compound, a compound of this invention, as a viscous oil (130 mg).

1H NMR (CDCl3): δ 1.28 (s, 9H), 4.75 (d, 1H), 5.37 (d, 1H), 5.97 (s, 1H), 6.16 (d, 1H), 7.45 (d, 1H), 7.46-7.8 (m, 4H).

EXAMPLE 2 Preparation of 5-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone

To a stirred solution of thionyl chloride (5.3 mL, 73 mmol) in 120 mL of methylene chloride at ˜10° C. was slowly added 3-(1,1-dimethylethyl)-1H-pyrazole (11.32 g, 91 mmol). The resulting solution was stirred for ˜20 minutes and was then cooled further to ˜0° C. To this solution was added N,N-diisopropylethylamine (26.5 mL, 152 mmol) dropwise at ˜0° C. and then 5-hydroxy-3-[3-trifluoromethyl)phenyl]-4-thiazolidinone (16 g, 61 mmol) portionwise at temperatures between 0° C. and 10° C. After the addition, the reaction mixture was allowed to warm up to room temperature, and stirred at room temperature for 3 days. To the reaction mixture was then added 120 mL of concentrated sodium bicarbonate aqueous solution. The methylene chloride layer was separated and the aqueous layer was extracted twice with methylene chloride (˜120 mL each). The methylene chloride layers were combined, dried over MgSO4 and then concentrated. The residue was loaded on silica gel in a flash chromatography column and eluted with hexanes followed by methylene chloride to give 15.74 g of a crude product. The crude product was further purified by trituration in hexanes followed by filtration to give the title compound, a compound of this invention, as a tan solid (11.8 g) melting at 66-69° C.

1H NMR (CDCl3): δ 1.28 (s, 9H), 4.75 (d, 1H), 5.37 (d, 1H), 5.97 (s, 1H), 6.16 (d, 1H), 7.45 (d, 1H), 7.46-7.8 (m, 4H).

EXAMPLE 3 Preparation of 3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone

To a solution of 3-(1,1-dimethylethyl)-1H-pyrazole (0.22 g, 1.8 mmol) in N,N-dimethylformamide (20 mL) under nitrogen at room temperature was added 60% sodium hydride in mineral oil (90 mg, 2.16 mmol). After the addition, the mixture was stirred at room temperature for ˜15 minutes, and 3-hydroxy-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone methanesulfonate (0.5 g, 1.8 mmol) was added. The resulting reaction mixture was stirred at room temperature overnight and then poured into water (˜100 mL). The aqueous layer was extracted twice with ethyl acetate (˜30 mL each; brine solution was added to separate the two layers). The organic extracts were combined, dried over MgSO4 and filtered. The filtrate was concentrated and the residue purified by column chromatography (silica gel, ˜20% ethyl acetate/80% hexanes) to give the title compound, a compound of this invention, as a yellow solid (300 mg) melting at 76-78° C.

1H NMR (CDCl3): δ 1.29 (s, 9H), 2.69-2.92 (m, 2H), 3.93 (m, 1H), 4.12 (m, 1H), 5.04 (t, 1H), 6.16 (d, 1H), 7.4-7.55 (m, 3H), 7.89-8.00 (m, 2H).

EXAMPLE 4 Preparation of 5-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone

To a solution of 5-hydroxy-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone (1 g, 4.05 mmol) in tetrahydrofuran (20 mL) under nitrogen at ˜0° C., were added 3-(1,1-dimethylethyl)-1H-pyrazole (0.5 g, 4.05 mmol), triphenylphosphine (1.23 g, 4.7 mmol) and diisopropyl azodicarboxylate (0.88 mL, 4.46 mmol). After the addition, the reaction mixture was allowed to warm up slowly to room temperature and stirred at room temperature overnight. The reaction mixture was then concentrated, and the residue was purified by column chromatography (silica gel, ˜20% ethylacetate/80% hexanes) to give a crude product. The crude product was further purified by column chromatography (silica gel, ˜20% ethyl acetate/˜80% hexanes) to give the title compound, a compound of this invention, as a white solid (14 mg) melting at 95-98° C.

1H NMR (CDCl3): δ 1.26 (s, 9H), 5.57 (d, 1H), 5.79 (d, 1H), 6.08 (s, 1H), 6.20 (d, 1H), 7.45-7.6 (m, 3H), 7.8-7.9 (m, 2H).

EXAMPLE 5 Step A: Preparation of 3-(1-ethylpropyl)-1H-pyrazole

To a stirred suspension of sodium methoxide (23.6 g, 0.437 mol) in diethyl ether (˜800 mL) was added dropwise a solution of 3-ethyl-2-pentanone (49.9 g, 0.437 mol) and ethyl formate (32.4 g, 0.437 mol) in diethyl ether (˜200 mL) at temperatures between 10° C. and 20° C. After the addition, the reaction mixture was allowed to warm up to room temperature, and stirred at room temperature for 2 hours. Additional diethyl ether (˜800 mL) was then added. The reaction mixture was stirred at room temperature for one additional hour and then concentrated. The residue was suspended in a solution of ethanol (950 mL) and acetic acid (30 mL). To this suspension was added hydrazine monohydrate (24 mL, 0.49 mol). The reaction mixture was heated at reflux for 60 hours and was then allowed to cool slowly to room temperature. The reaction mixture was then concentrated. To the residue was added 200 mL of 1N hydrochloric acid, followed by ˜75 mL of concentrated hydrochloric acid until pH ˜0. The acidic aqueous solution was then washed twice with diethyl ether (˜250 mL each). The pH of the aqueous solution was then adjusted to 9-10 by addition of aqueous 50% sodium hydroxide solution The aqueous solution was then extracted twice with diethyl ether (˜300 mL each). The diethyl ether extracts were combined, dried over MgSO4 and concentrated to give the title compound as a pale yellow oil (41 g).

1H NMR (CDCl3): δ 0.84 (t, 6H), 1.5-1.8 (m, 4H), 2.53-2.65 (m, 1H), 6.06 (d, 1H), 7.52 (d, 1H).

Step B: Preparation of 5-[3-(1-ethylpropyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone

To a stirred solution of thionyl chloride (5 mL, 68.55 mmol) in methylene chloride (100 mL) at ˜10° C. was slowly added 3-(1-ethylpropyl)-1H-pyrazole (11.74 g, 84.94 mmol). The resulting solution was stirred for ˜20 minutes and was then cooled to ˜0° C. To this solution was added N,N-diisopropylethylamine (24.7 mL, 141.8 mmol) dropwise and then 5-hydroxy-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone (14 g, 56.64 mmol), portionwise at temperatures between 0° C. and 15° C. After the addition, the reaction mixture was allowed to warm to room temperature, and then stirred at room temperature for 2 days. To the reaction mixture was then added concentrated aqueous sodium bicarbonate solution (100 mL). The methylene chloride layer was separated, and the aqueous layer was extracted twice with methylene chloride (˜100 mL each). The methylene chloride layers were combined, dried over MgSO4 and then concentrated. The residue was loaded on silica gel in a column and eluted with methylene chloride to give a crude product The crude product was further purified by trituration in hexanes followed by filtration to give the title compound, a compound of this invention, as a white solid (10.67 g) melting at 83-85° C.

1H NMR (CDCl3): δ 0.83 (t, 6H), 1.44-1.7 (m, 4H), 2.45-2.60 (m, 1H), 5.56 (m, 1H), 5.80 (m, 1H), 6.08 (s, 1H), 6.15 (d, 1H), 7.5-7.6 (m, 3H), 7.85 (m, 2H).

EXAMPLE 6 Step A: Preparation of 3-bromo-1-(4-chloro-3-methoxyphenyl)-2-pyrrolidinone

To a stirred solution of 4-chloro-3-methoxybenzeneamine (4.7 g, 29.6 mmol) in methylene chloride (100 mL) at ˜0° C. was slowly added 2,4-dibromobutyryl chloride (5.1 mL, 39 mmol). After the addition, the reaction mixture was stirred for ˜5 minutes and triethylamine (24.7 mL, 178 mmol) was then added. The resulting reaction mixture was allowed to warm up to room temperature and stirred at room temperature for 5 days. Water (˜100 mL) was then added to the reaction mixture. The organic layer was separated, dried over MgSO4 and concentrated. The residue was purified by column chromatography (silica gel ˜33% ethyl acetate/˜67% hexanes) to give the title compound as a yellow solid (3.9 g) melting at 113-115° C.

1H NMR (CDCl3): δ 2.3-2.53 (m, 1H), 2.6-2.8 (m, 1H), 3.78-4.1 (m, 5H), 4.5-4.6 (m, 1H), 6.8 (m, 1H), 7.34 (d, 1H), 7.77 (d, 1H).

Step B: Preparation of 1-(4-chloro-3-methoxyphenyl)-3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-2-pyrrolidinone

To a solution of 3-(1,1-dimethylethyl)-1H-pyrazole (0.22 g, 1.8 mmol) in N,N-dimethylformamide (20 mL) under nitrogen at room temperature was added 60% sodium hydride in mineral oil (79 mg, 2.0 mmol). After the addition, the mixture was stirred at room temperature for ˜15 minutes, and then 3-bromo-1-(4-chloro-3-methoxyphenyl)-2-pyrrolidinone (0.5 g, 1.6 mmol) was added. The resulting reaction mixture was stirred at room temperature overnight and then poured into water (˜100 mL). The aqueous layer was extracted twice with ethyl acetate (˜50 mL each). The organic extracts were combined, washed twice with water (˜100 mL each), dried over MgSO4 and filtered. The filtrate was concentrated. The residue was purified by medium pressure liquid chromatography (silica gel) using as eluant methylene chloride and then 10:1 (by volume) ethyl acetate-methylene chloride to give the title compound, a compound of this invention, as a solid (186 mg) melting at 128-130° C.

1H NMR (CDCl3): δ 1.29 (s, 9H), 2.7-2.98 (m, 2H), 3.84-4.17 (m, 5H), 5.04 (t, 1H), 6.17 (d, 1H), 6.81-6.9 (m, 1H), 7.35 (d, 1H), 7.47 (d, 1H), 7.84 (d, 1H).

EXAMPLE 7 Step A: Preparation of 2-[(dimethylamino)methylene]-5,5-dimethylcyclopentanone

A mixture of N,N-dimethylformamide dimethyl acetal (67 mL, 503 mmol) and 2,2-dimethylcyclopentanone (10 g, 90 mmol) was heated at reflux for 2 days. The reaction mixture was then cooled down to room temperature and concentrated. Water (˜380 mL) was added to the residue, and the resulting solution was extracted with methylene chloride. The organic layer was separated, dried over MgSO4 and concentrated to give the title compound (12.5 g) as a yellow-orange oil.

1H NMR (CDCl3): δ 1.03 (s, 6H), 1.68 (t, 2H), 2.74 (t, 2H), 3.06 (s, 6H), 7.19 (s, 1H).

Step B: Preparation of 2,4,5,6-tetrahydro-6,6-dimethylcyclopentapyrazole

To a solution of 2-[(dimethylamino)methylene]-5,5-dimethylcyclopentanone (12.5 g, 75 mmol) in ethanol (100 mL) at room temperature was added hydrazine hydrate (4 mL, 82.3 mmol). The reaction mixture was heated at reflux overnight. It was then cooled to room temperature and concentrated. Water (700 mL) was added to the residue, and the resulting solution was extracted twice with diethyl ether (2×250 mL). The organic extracts were combined, dried over MgSO4 and concentrated to give the title compound as an oil (10.5 g). 1H NMR indicated the oil to be ˜60% pure. It was used directly for Step C.

Step C: Preparation of 3-(5,6-dihydro-4,4-dimethyl-2(4)-cyclopentapyrazolyl)-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone

To a solution of 2,4,5,6-tetrahydro-6,6-dimethylcyclopentapyrazole (0.41 g with 60% purity, 1.8 mmol) in N,N-dimethylformamide (20 mL) under nitrogen at room temperature was added sodium hydride (60% in mineral oil, 86 mg, 2.16 mmol). The mixture was sired at room temperature under nitrogen for ˜15 minutes, and then 3-hydroxy-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone methanesulfonate (0.5 g, 1.8 mmol) was added. The resulting reaction mixture was stirred at room temperature for 72 hours. The reaction mixture was then poured into water (˜100 mL) and the aqueous layer extracted with ethyl acetate (2×30 mL; brine solution was added to separate the layers). The organic extracts were combined and concentrated to give a crude product. This crude product was further purified by column chromatography (silica gel, ˜20% ethyl acetate/˜80% hexanes) to give the title compound, a compound of this invention, as an oil, which on standing crystallized to provide a solid (69 mg) melting at 123-126° C.

1H NMR (CDCl3): δ 1.3 (s, 61), 2.21 (t, 2H), 2.61 (t, 2H), 2.7-2.87(m, 2H), 3.87-4.1 (m, 2H), 5.04 (t, 1H), 7.13 (s, 1H), 7.4-7.55 (m, 2H) 7.9-8.0 (m, 2H).

By the procedures described herein together with methods known in the art, the following compounds of Tables 1A to 6 can be prepared.

The following tables use the following well-established abbreviations: n means normal, i means iso, s means secondary, t means tertiary and c means cyclo.

TABLE 1A Z R1 A is A-1; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S 2-Me-c-Pr S 1-Me-2,2-di-Cl-c-Pr S c-Bu S 2,2-di-Cl-c-Pr S Trimethylsilyl S Si(CH3)2(t-C4H9) S C2H5 S CH3 S H S Br S I CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 2-Me-c-Pr CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Bu CH2 2,2-di-Cl-c-Pr CH2 Trimethylsilyl CH2 Si(CH3)2(t-C4H9) CH2 C2H5 CH2 CH3 CH2 H CH2 Br CH2 I O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O 2-Me-c-Pr O 1-Me-2,2-di-Cl-c-Pr O c-Bu O 2,2-di-Cl-c-Pr O Trimethylsilyl O Si(CH3)2(t-C4H9) O C2H5 O CH3 O H O Br O I S Cl S C(═O)CH3 S C(═O)OCH3 S C(═O)CH(CH3)2 S OCH3 S SCH3 S N(CH3)2 S C(═O)N(CH3)2 S C(═O)O(CH3)3 S n-C3H7 S CCl3 S CHClCH3 S SC2H5 S SCH(CH3)2 S SCH(CH3)(C2H5) S SCF3 S OCH(CH3)2 S OCH(CH3)(C2H5) S OCH(C2H5)2 S OCHF2 S C(CH3)2C2H5 S CH2C(CH3)3 S c-Pentyl S c-Hexyl S c-Octyl S CH(CH3)(n-C3H7) S CH(C2H5)(n-C3H7) S CH(n-C3H7)2 S CH(n-C4H9)2 S CH(CH3)(n-C4H9) S CH(CH3)(n-C5H11) S CH(CH3)(n-C10H21) S C(CH3)(C2H5)2 S CH2CF3 CH2 Cl CH2 C(═O)CH3 CH2 C(═O)OCH3 CH2 C(═O)CH(CH3)2 CH2 OCH3 CH2 SCH3 CH2 N(CH3)2 CH2 C(═O)N(CH3)2 CH2 C(═O)C(CH3)3 CH2 n-C3H7 CH2 CCl3 CH2 CHClCH3 CH2 SC2H5 CH2 SCH(CH3)2 CH2 SCH(CH3)(C2H5) CH2 SCF3 CH2 OCH(CH3)2 CH2 OCH(CH3)(C2H5) CH2 OCH(C2H5)2 CH2 OCHF2 CH2 C(CH3)2C2H5 CH2 CH2C(CH3)3 CH2 c-Pentyl CH2 c-Hexyl CH2 c-Octyl CH2 CH(CH3)(n-C3H7) CH2 CH(C2H5)(n-C3H7)2 CH2 CH(n-C3H7)2 CH2 CH(n-C4H9)2 CH2 CH(CH3)(n-C4H9) CH2 CH(CH3)(n-C5H11) CH2 CH(CH3)(n-C10H21) CH2 C(CH3)(C2H5)2 CH2 CH2CF3 O Cl O C(═O)CH3 O C(═O)OCH3 O C(═O)CH(CH3)2 O OCH3 O SCH3 O N(CH3)2 O C(═O)N(CH3)2 O C(═O)C(CH3)3 O n-C3H7 O CCl3 O CHClCH3 O SC2H5 O SCH(CH3)2 O SCH(CH3)(C2H5) O SCF3 O OCH(CH3)2 O OCH(CH3)(C2H5) O OCH(C2H5)2 O OCHF2 O C(CH3)2C2H5 O CH2C(CH3)3 O c-Pentyl O c-Hexyl O c-Octyl O CH(CH3)(n-C3H7) O CH(C2H5)(n-C3H7) O CH(n-C3H7)2 O CH(n-C4H9)2 O CH(CH3)(n-C4H9) O CH(CH3)(n-C5H11) O CH(CH3)(n-C10H21) O C(CH3)(C2H5)2 O CH2CF3 A is A-3; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S 2-Me-c-Pr S 1-Me-2,2-di-Cl-c-Pr S c-Bu S 2,2-di-Cl-c-Pr S Trimethylsilyl S Si(CH3)2(t-C4H9) S C2H5 S CH3 S H S Br S I S Cl S C(═O)CH3 S C(═O)OCH3 S C(═O)CH(CH3)2 S OCH3 S SCH3 S N(CH3)2 S C(═O)N(CH3)2 S C(═O)C(CH3)3 S n-C3H7 S CCl3 S CHClCH3 S SC2H5 S SCH(CH3)2 S SCH(CH3)(C2H5) S SCF3 S OCH(CH3)2 S OCH(CH3)(C2H5) S OCH(C2H5)2 S OCHF2 S C(CH3)2C2H5 S CH2C(CH3)3 S c-Pentyl S c-Hexyl S c-Octyl S CH(CH3)(n-C3H7) S CH(C2H5)(n-C3H7) S CH(n-C3H7)2 S CH(n-C4H9)2 S CH(CH3)(n-C4H9) S CH(CH3)(n-C5H11) S CH(CH3)(n-C10H21) S C(CH3)(C2H5)2 S CH2CF3 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 2-Me-c-Pr CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Bu CH2 2,2-di-Cl-c-Pr CH2 Trimethylsilyl CH2 Si(CH3)2(t-C4H9) CH2 C2H5 CH2 CH3 CH2 H CH2 Br CH2 I CH2 Cl CH2 C(═O)CH3 CH2 C(═O)OCH3 CH2 C(═O)CH(CH3)2 CH2 OCH3 CH2 SCH3 CH2 N(CH3)2 CH2 C(═O)N(CH3)2 CH2 O(═O)C(CH3)3 CH2 n-C3H7 CH2 CCl3 CH2 CHClCH3 CH2 SC2H5 CH2 SCH(CH3)2 CH2 SCH(CH3)(C2H5) CH2 SCF3 CH2 OCH(CH3)2 CH2 OCH(CH3)(C2H5) CH2 OCH(C2H5)2 CH2 OCHF2 CH2 C(CH3)2C2H5 CH2 CH2C(CH3)3 CH2 c-Pentyl CH2 c-Hexyl CH2 c-Octyl CH2 CH(CH3)(n-C3H7) CH2 CH(C2H5)(n-C3H7) CH2 CH(n-C3H7)2 CH2 CH(n-C4H9)2 CH2 CH(CH3)(n-C4H9) CH2 CH(CH3)(n-C5H11) CH2 CH(CH3)(n-C10H21) CH2 C(CH3)(C2H5)2 CH2 CH2CF3 O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O 2-Me-c-Pr O 1-Me-2,2-di-Cl-c-Pr O c-Bu O 2,2-di-Cl-c-Pr O Trimethylsilyl O Si(CH3)2(t-C4H9) O C2H5 O CH3 O H O Br O I O Cl O C(═O)CH3 O C(═O)OCH3 O C(═O)CH(CH3)2 O OCH3 O SCH3 O N(CH3)2 O C(═O)N(CH3)2 O C(═O)C(CH3)3 O n-C3H7 O CCl3 O CHClCH3 O SC2H5 O SCH(CH3)2 O SCH(CH3)(C2H5) O SCF3 O OCH(CH3)2 O OCH(C2H5) O OCH(C2H5)2 O C(CH3)2C2H5 O CH2C(CH3)3 O c-Pentyl O c-Hexyl O c-Octyl O CH(CH3)(n-C3H7) O CH(C2H5)(n-C3H7) O CH(n-C3H7)2 O CH(n-C4H9)2 O CH(CH3)(n-C4H9) O CH(CH3)(n-C5H11) O CH(CH3)(n-C10H21) O C(CH3)(C2H5)2 O CH2CF3 A is A-5; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S 2-Me-c-Pr S 1-Me-2,2-di-Cl-c-Pr S c-Bu S 2,2-di-Cl-c-Pr S Trimethylsilyl S Si(CH3)2(t-C4H9) S C2H5 S CH3 S H S Br S I S Cl S C(═O)CH3 S C(═O)OCH3 S C(═O)CH(CH3)2 S OCH3 S SCH3 S N(CH3)2 S C(═O)N(CH3)2 S C(═O)C(CH3)3 S n-C3H7 S CCl3 S CHClCH3 S SC2H5 S SCH(CH3)2 S SCH(CH3)(C2H5) S SCF3 S OCH(CH3)2 S OCH(CH3)(C2H5) S OCH(C2H5)2 S OCHF2 S C(CH3)2C2H5 S CH2C(CH3)3 S c-Pentyl S c-Hexyl S c-Octyl S CH(CH3)(n-C3H7) S CH(C2H5)(n-C3H7) S CH(n-C3H7)2 S CH(n-C4H9)2 S CH(CH3)(n-C4H9) S CH(CH3)(n-C5H11) S CH(CH3)(n-C10H21) S C(CH3)(C2H5)2 S CH2CF3 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 2-Me-c-Pr CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Bu CH2 2,2-di-Cl-c-Pr CH2 Trimethylsilyl CH2 Si(CH3)2(t-C4H9) CH2 C2H5 CH2 CH3 CH2 H CH2 Br CH2 I CH2 Cl CH2 C(═O)CH3 CH2 C(═O)OCH3 CH2 C(═O)CH(CH3)2 CH2 OCH3 CH2 SCH3 CH2 N(CH3)2 CH2 C(═O)N(CH3)2 CH2 C(═O)C(CH3)3 CH2 n-C3H7 CH2 CCl3 CH2 CHClCH3 CH2 SC2H5 CH2 SCH(CH3)2 CH2 SCH(CH3)(C2H5) CH2 SCF3 CH2 OCH(CH3)2 CH2 OCH(CH3)(C2H5) CH2 OCH(C2H5)2 CH2 OCHF2 CH2 C(CH3)2C2H5 CH2 CH2C(CH3)3 CH2 c-Pentyl CH2 c-Hexyl CH2 c-Octyl CH2 CH(CH3)(n-C3H7) CH2 CH(C2H5)(n-C3H7) CH2 CH(n-C3H7)2 CH2 CH(n-C4H9)2 CH2 CH(CH3)(n-C4H9) CH2 CH(CH3)(n-C5H11) CH2 CH(CH3)(n-C10H21) CH2 C(CH3)(C2H5)2 CH2 CH2CF3 O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O 2-Me-c-Pr O 1-Me-2,2-di-Cl-c-Pr O c-Bu O 2,2-di-Cl-c-Pr O Trimethylsilyl O Si(CH3)2(t-C4H9) O C2H5 O CH3 O H O Br O I O Cl O C(═O)CH3 O C(═O)OCH3 O C(═O)CH(CH3)2 O OCH3 O SCH3 O N(CH3)2 O C(═O)N(CH3)2 O C(═O)C(CH3)3 O n-C3H7 O CCl3 O CHClCH3 O SC2H5 O SCH(CH3)2 O SCH(CH3)(C2H5) O SCF3 O OCH(CH3)2 O OCH(C2H5) O OCH(C2H5)2 O C(CH3)2C2H5 O CH2C(CH3)3 O c-Pentyl O c-Hexyl O c-Octyl O CH(CH3)(n-C3H7) O CH(C2H5)(n-C3H7) O CH(n-C3H7)2 O CH(n-C4H9)2 O CH(CH3)(n-C4H9) O CH(CH3)(n-C5H11) O CH(CH3)(n-C10H21) O C(CH3)(C2H5)2 O CH2CF3 A is A-14; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S 2-Me-c-Pr S 1-Me-2,2-di-Cl-c-Pr S c-Bu S 2,2-di-Cl-c-Pr S Trimethylsilyl S Si(CH3)2(t-C4H9) S C2H5 S CH3 S H S Br S I S Cl S C(═O)CH3 S C(═O)OCH3 S C(═O)CH(CH3)2 S OCH3 S SCH3 S N(CH3)2 S C(═O)N(CH3)2 S C(═O)C(CH3)3 S n-C3H7 S CCl3 S CHClCH3 S SC2H5 S SCH(CH3)2 S SCH(CH3)(C2H5) S SCF3 S OCH(CH3)2 S OCH(CH3)(C2H5) S OCH(C2H5)2 S OCHF2 S C(CH3)2C2H5 S CH2C(CH3)3 S c-Pentyl S c-Hexyl S c-Octyl S CH(CH3)(n-C3H7) S CH(C2H5)(n-C3H7) S CH(n-C3H7)2 S CH(n-C4H9)2 S CH(CH3)(n-C4H9) S CH(CH3)(n-C5H11) S CH(CH3)(n-C10H21) S C(CH3)(C2H5)2 S CH2CF3 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 2-Me-c-Pr CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Bu CH2 2,2-di-Cl-c-Pr CH2 Trimethylsilyl CH2 Si(CH3)2(t-C4H9) CH2 C2H5 CH2 CH3 CH2 H CH2 Br CH2 I CH2 Cl CH2 C(═O)CH3 CH2 C(═O)OCH3 CH2 C(═O)CH(CH3)2 CH2 OCH3 CH2 SCH3 CH2 N(CH3)2 CH2 C(═O)N(CH3)2 CH2 C(═O)C(CH3)3 CH2 n-C3H7 CH2 CCl3 CH2 CHClCH3 CH2 SC2H5 CH2 SCH(CH3)2 CH2 SCH(CH3)(C2H5) CH2 SCF3 CH2 OCH(CH3)2 CH2 OCH(CH3)(C2H5) CH2 OCH(C2H5)2 CH2 OCHF2 CH2 C(CH3)2C2H5 CH2 CH2C(CH3)3 CH2 c-Pentyl CH2 c-Hexyl CH2 c-Octyl CH2 CH(CH3)(n-C3H7) CH2 CH(C2H5)(n-C3H7) CH2 CH(n-C3H7)2 CH2 CH(n-C4H9)2 CH2 CH(CH3)(n-C4H9) CH2 CH(CH3)(n-C5H11) CH2 CH(CH3)(n-C10H21) CH2 C(CH3)(C2H5)2 CH2 CH2CF3 O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O 2-Me-c-Pr O 1-Me-2,2-di-Cl-c-Pr O c-Bu O 2,2-di-Cl-c-Pr O Trimethylsilyl O Si(CH3)2(t-C4H9) O C2H5 O CH3 O H O Br O I O Cl O C(═O)CH3 O C(═O)OCH3 O C(═O)CH(CH3)2 O OCH3 O SCH3 O N(CH3)2 O C(═O)N(CH3)2 O C(═O)C(CH3)3 O n-C3H7 O CCl3 O CHClCH3 O SC2H5 O SCH(CH3)2 O SCH(CH3)(C2H5) O SCF3 O OCH(CH3)2 O OCH(C2H5) O OCH(C2H5)2 O C(CH3)2C2H5 O CH2C(CH3)3 O c-Pentyl O c-Hexyl O c-Octyl O CH(CH3)(n-C3H7) O CH(C2H5)(n-C3H7) O CH(n-C3H7)2 O CH(n-C4H9)2 O CH(CH3)(n-C4H9) O CH(CH3)(n-C5H11) O CH(CH3)(n-C10H21) O C(CH3)(C2H5)2 O CH2CF3 A is A-29; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S 2-Me-c-Pr S 1-Me-2,2-di-Cl-c-Pr S c-Bu S 2,2-di-Cl-c-Pr S Trimethylsilyl S Si(CH3)2(t-C4H9) S C2H5 S CH3 S H S Br S I S Cl S C(═O)CH3 S C(═O)OCH3 S C(═O)CH(CH3)2 S OCH3 S SCH3 S N(CH3)2 S C(═O)N(CH3)2 S C(═O)C(CH3)3 S n-C3H7 S CCl3 S CHClCH3 S SC2H5 S SCH(CH3)2 S SCH(CH3)(C2H5) S SCF3 S OCH(CH3)2 S OCH(CH3)(C2H5) S OCH(C2H5)2 S OCHF2 S C(CH3)2C2H5 S CH2C(CH3)3 S c-Pentyl S c-Hexyl S c-Octyl S CH(CH3)(n-C3H7) S CH(C2H5)(n-C3H7) S CH(n-C3H7)2 S CH(n-C4H9)2 S CH(CH3)(n-C4H9) S CH(CH3)(n-C5H11) S CH(CH3)(n-C10H21) S C(CH3)(C2H5)2 S CH2CF3 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 2-Me-c-Pr CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Bu CH2 2,2-di-Cl-c-Pr CH2 Trimethylsilyl CH2 Si(CH3)2(t-C4H9) CH2 C2H5 CH2 CH3 CH2 H CH2 Br CH2 I CH2 Cl CH2 C(═O)CH3 CH2 C(═O)OCH3 CH2 C(═O)CH(CH3)2 CH2 OCH3 CH2 SCH3 CH2 N(CH3)2 CH2 C(═O)N(CH3)2 CH2 C(═O)C(CH3)3 CH2 n-C3H7 CH2 CCl3 CH2 CHClCH3 CH2 SC2H5 CH2 SCH(CH3)2 CH2 SCH(CH3)(C2H5) CH2 SCF3 CH2 OCH(CH3)2 CH2 OCH(CH3)(C2H5) CH2 OCH(C2H5)2 CH2 OCHF2 CH2 C(CH3)2C2H5 CH2 CH2C(CH3)3 CH2 c-Pentyl CH2 c-Hexyl CH2 c-Octyl CH2 CH(CH3)(n-C3H7) CH2 CH(C2H5)(n-C3H7) CH2 CH(n-C3H7)2 CH2 CH(n-C4H9)2 CH2 CH(CH3)(n-C4H9) CH2 CH(CH3)(n-C5H11) CH2 CH(CH3)(n-C10H21) CH2 C(CH3)(C2H5)2 CH2 CH2CF3 O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O 2-Me-c-Pr O 1-Me-2,2-di-Cl-c-Pr O c-Bu O 2,2-di-Cl-c-Pr O Trimethylsilyl O Si(CH3)2(t-C4H9) O C2H5 O CH3 O H O Br O I O Cl O C(═O)CH3 O C(═O)OCH3 O C(═O)CH(CH3)2 O OCH3 O SCH3 O N(CH3)2 O C(═O)N(CH3)2 O C(═O)C(CH3)3 O n-C3H7 O CCl3 O CHClCH3 O SC2H5 O SCH(CH3)2 O SCH(CH3)(C2H5) O SCF3 O OCH(CH3)2 O OCH(C2H5) O OCH(C2H5)2 O C(CH3)2C2H5 O CH2C(CH3)3 O c-Pentyl O c-Hexyl O c-Octyl O CH(CH3)(n-C3H7) O CH(C2H5)(n-C3H7) O CH(n-C3H7)2 O CH(n-C4H9)2 O CH(CH3)(n-C4H9) O CH(CH3)(n-C5H11) O CH(CH3)(n-C10H21) O C(CH3)(C2H5)2 O CH2CF3 A is A-46; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S 2-Me-c-Pr S 1-Me-2,2-di-Cl-c-Pr S c-Bu S 2,2-di-Cl-c-Pr S Trimethylsilyl S Si(CH3)2(t-C4H9) S C2H5 S CH3 S H S Br S I S Cl S C(═O)CH3 S C(═O)OCH3 S C(═O)CH(CH3)2 S OCH3 S SCH3 S N(CH3)2 S C(═O)N(CH3)2 S C(═O)C(CH3)3 S n-C3H7 S CCl3 S CHClCH3 S SC2H5 S SCH(CH3)2 S SCH(CH3)(C2H5) S SCF3 S OCH(CH3)2 S OCH(CH3)(C2H5) S OCH(C2H5)2 S OCHF2 S C(CH3)2C2H5 S CH2C(CH3)3 S c-Pentyl S c-Hexyl S c-Octyl S CH(CH3)(n-C3H7) S CH(C2H5)(n-C3H7) S CH(n-C3H7)2 S CH(n-C4H9)2 S CH(CH3)(n-C4H9) S CH(CH3)(n-C5H11) S CH(CH3)(n-C10H21) S C(CH3)(C2H5)2 S CH2CF3 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 2-Me-c-Pr CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Bu CH2 2,2-di-Cl-c-Pr CH2 Trimethylsilyl CH2 Si(CH3)2(t-C4H9) CH2 C2H5 CH2 CH3 CH2 H CH2 Br CH2 I CH2 Cl CH2 C(═O)CH3 CH2 C(═O)OCH3 CH2 C(═O)CH(CH3)2 CH2 OCH3 CH2 SCH3 CH2 N(CH3)2 CH2 C(═O)N(CH3)2 CH2 C(═O)C(CH3)3 CH2 n-C3H7 CH2 CCl3 CH2 CHClCH3 CH2 SC2H5 CH2 SCH(CH3)2 CH2 SCH(CH3)(C2H5) CH2 SCF3 CH2 OCH(CH3)2 CH2 OCH(CH3)(C2H5) CH2 OCH(C2H5)2 CH2 OCHF2 CH2 C(CH3)2C2H5 CH2 CH2C(CH3)3 CH2 c-Pentyl CH2 c-Hexyl CH2 c-Octyl CH2 CH(CH3)(n-C3H7) CH2 CH(C2H5)(n-C3H7) CH2 CH(n-C3H7)2 CH2 CH(n-C4H9)2 CH2 CH(CH3)(n-C4H9) CH2 CH(CH3)(n-C5H11) CH2 CH(CH3)(n-C10H21) CH2 C(CH3)(C2H5)2 CH2 CH2CF3 O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O 2-Me-c-Pr O 1-Me-2,2-di-Cl-c-Pr O c-Bu O 2,2-di-Cl-c-Pr O Trimethylsilyl O Si(CH3)2(t-C4H9) O C2H5 O CH3 O H O Br O I O Cl O C(═O)CH3 O C(═O)OCH3 O C(═O)CH(CH3)2 O OCH3 O SCH3 O N(CH3)2 O C(═O)N(CH3)2 O C(═O)C(CH3)3 O n-C3H7 O CCl3 O CHClCH3 O SC2H5 O SCH(CH3)2 O SCH(CH3)(C2H5) O SCF3 O OCH(CH3)2 O OCH(C2H5) O OCH(C2H5)2 O C(CH3)2C2H5 O CH2C(CH3)3 O c-Pentyl O c-Hexyl O c-Octyl O CH(CH3)(n-C3H7) O CH(C2H5)(n-C3H7) O CH(n-C3H7)2 O CH(n-C4H9)2 O CH(CH3)(n-C4H9) O CH(CH3)(n-C5H11) O CH(CH3)(n-C10H21) O C(CH3)(C2H5)2 O CH2CF3 A is A-59; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S 2-Me-c-Pr S 1-Me-2,2-di-Cl-c-Pr S c-Bu S 2,2-di-Cl-c-Pr S Trimethylsilyl S Si(CH3)2(t-C4H9) S C2H5 S CH3 S H S Br S I S Cl S C(═O)CH3 S C(═O)OCH3 S C(═O)CH(CH3)2 S OCH3 S SCH3 S N(CH3)2 S C(═O)N(CH3)2 S C(═O)C(CH3)3 S n-C3H7 S CCl3 S CHClCH3 S SC2H5 S SCH(CH3)2 S SCH(CH3)(C2H5) S SCF3 S OCH(CH3)2 S OCH(CH3)(C2H5) S OCH(C2H5)2 S OCHF2 S C(CH3)2C2H5 S CH2C(CH3)3 S c-Pentyl S c-Hexyl S c-Octyl S CH(CH3)(n-C3H7) S CH(C2H5)(n-C3H7) S CH(n-C3H7)2 S CH(n-C4H9)2 S CH(CH3)(n-C4H9) S CH(CH3)(n-C5H11) S CH(CH3)(n-C10H21) S C(CH3)(C2H5)2 S CH2CF3 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 2-Me-c-Pr CH2 1-Me-2,2-di-01-c-Pr CH2 c-Bu CH2 2,2-di-Cl-c-Pr CH2 Trimethylsilyl CH2 Si(CH3)2(t-C4H9) CH2 C2H5 CH2 CH3 CH2 H CH2 Br CH2 I CH2 Cl CH2 C(═O)CH3 CH2 C(═O)OCH3 CH2 C(═O)CH(CH3)2 CH2 OCH3 CH2 SCH3 CH2 N(CH3)2 CH2 C(═O)N(CH3)2 CH2 C(═O)C(CH3)3 CH2 n-C3H7 CH2 CCl3 CH2 CHClCH3 CH2 SC2H5 CH2 SCH(CH3)2 CH2 SCH(CH3)(C2H5) CH2 SCF3 CH2 OCH(CH3)2 CH2 OCH(CH3)(C2H5) CH2 OCH(C2H5)2 CH2 OCHF2 CH2 C(CH3)2C2H5 CH2 CH2C(CH3)3 CH2 c-Pentyl CH2 c-Hexyl CH2 c-Octyl CH2 CH(CH3)(n-C3H7) CH2 CH(C2H5)(n-C3H7) CH2 CH(n-C3H7)2 CH2 CH(n-C4H9)2 CH2 CH(CH3)(n-C4H9) CH2 CH(CH3)(n-C5H11) CH2 CH(CH3)(n-C10H21) CH2 C(CH3)(C2H5)2 CH2 CH2CF3 O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O 2-Me-c-Pr O 1-Me-2,2-di-Cl-c-Pr O c-Bu O 2,2-di-Cl-c-Pr O Trimethylsilyl O Si(CH3)2(t-C4H9) O C2H5 O CH3 O H O Br O I O Cl O C(═O)CH3 O C(═O)OCH3 O C(═O)CH(CH3)2 O OCH3 O SCH3 O N(CH3)2 O C(═O)N(CH3)2 O C(═O)C(CH3)3 O n-C3H7 O CCl3 O CHClCH3 O SC2H5 O SCH(CH3)2 O SCH(CH3)(C2H5) O SCF3 O OCH(CH3)2 O OCH(C2H5) O OCH(C2H5)2 O C(CH3)2C2H5 O CH2C(CH3)3 O c-Pentyl O c-Hexyl O c-Octyl O CH(CH3)(n-C3H7) O CH(C2H5)(n-C3H7) O CH(n-C3H7)2 O CH(n-C4H9)2 O CH(CH3)(n-C4H9) O CH(CH3)(n-C5H11) O CH(CH3)(n-C10H21) O C(CH3)(C2H5)2 O CH2CF3

TABLE 1B W Z R1 R2b A is A-1 CH2 S(O) C(CH3)3 H CH2 S(O) CH(CH3)2 H CH2 S(O) CH(CH3)(C2H5) H CH2 S(O) CH(C2H5)2 H CH2 S(O) c-Pr H CH2 S(O) 1-Me-c-Pr H CH2 S(O) c-Ru H CH2 S(O) 1-Me-2,2-di-Cl-c-Pr H CH2 S C(CH3)3 H CH2 S CH(CH3)2 H CH2 S CH(CH3)(C2H5) H CH2 S c-Pr CH3 CH2 S 1-Me-c-Pr CH3 CH2 S c-Bu CH3 CH2 CH2 C(CH3)3 CH3 CH2 CH2 CH(CH3)2 CH3 CH2 CH2 CH(CH3)(C2H5) CH3 CH2 CH2 c-Pr CH3 CH2 CH2 i-Me-c-Pr CH3 CH2 CH2 c-Bu CH3 CH2 O C(CH3)3 CH3 CH2 O CH(CH3)2 CH3 CH2 O CH(CH3)(C2H5) CH3 CH2 O c-Pr CH3 CH2 O 1-Me-c-Pr CH3 CH2 O c-Pentyl CH3 CH2 O 1-Me-2,2-di-Cl-c-Pr CH3 CH(CH3) CH2 C(CH3)3 H CH(CH3) CH2 CH(CH3)2 H CH(CH3) CH2 CH(CH3)(C2H5) H CH(CH3) CH2 CH(C2H5)2 H CH(CH3) CH2 c-Pr H CH(CH3) CH2 c-Bu H CH2 CH2 CH(CH3)(n-C10H21) CH3 A is A-5 CH2 S(O) C(CH3)3 H CH2 S(O) CH(CH3)2 H CH2 S(O) CH(CH3)(C2H5) H CH2 S(O) CH(C2H5)2 H CH2 S(O) c-Pr H CH2 S(O) 1-Me-c-Pr H CH2 S(O) c-Ru H CH2 S(O) 1-Me-2,2-di-Cl-c-Pr H CH2 S C(CH3)3 H CH2 S CH(CH3)2 H CH2 S CH(CH3)(C2H5) H CH2 S c-Pr CH3 CH2 S 1-Me-c-Pr CH3 CH2 S c-Bu CH3 CH2 CH2 C(CH3)3 CH3 CH2 CH2 CH(CH3)2 CH3 CH2 CH2 CH(CH3)(C2H5) CH3 CH2 CH2 c-Pr CH3 CH2 CH2 i-Me-c-Pr CH3 CH2 CH2 c-Bu CH3 CH2 O C(CH3)3 CH3 CH2 O CH(CH3)2 CH3 CH2 O CH(CH3)(C2H5) CH3 CH2 O c-Pr CH3 CH2 O 1-Me-c-Pr CH3 CH2 O c-Pentyl CH3 CH2 O 1-Me-2,2-di-Cl-c-Pr CH3 CH(CH3) CH2 C(CH3)3 H CH(CH3) CH2 CH(CH3)2 H CH(CH3) CH2 CH(CH3)(C2H5) H CH(CH3) CH2 CH(C2H5)2 H CH(CH3) CH2 c-Pr H CH(CH3) CH2 c-Bu H CH2 CH2 CH(CH3)(n-C10H21) CH3

TABLE 1C Z R1 A is A-6; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-8; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-9; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-12; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-20; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-21; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-32; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-34; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-36; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-43; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-47; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-60; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-62; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-66; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-67; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-68; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-69; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-70; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-71; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-72; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-73; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-74; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-75; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-76; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-77; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-78; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-79; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-80; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-81; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-82; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-83; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-84; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-85; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(CH3)(CH2)2CH3 S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(CH3)(CH2)2CH3 CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(CH3)(CH2)2CH3 O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21)

TABLE 1D W is CH2; R2b is H A Z R1 A-2 S C(CH3)3 A-2 S CH(CH3)2 A-2 S CH(CH3)(C2H5) A-2 S c-Pr A-2 CH2 C(CH3)3 A-2 CH2 CH(CH3)2 A-2 CH2 CH(CH3)(C2H5) A-2 CH2 c-Pr A-2 O C(CH3)3 A-2 O CH(CH3)2 A-2 O CH(CH3)(C2H5) A-2 O c-Pr A-4 S C(CH3)3 A-4 S CH(CH3)2 A-4 S CH(CH3)(C2H5) A-4 S c-Pr A-4 CH2 C(CH3)3 A-4 CH2 CH(CH3)2 A-10 S C(CH3)3 A-10 S CH(CH3)2 A-10 S CH(CH3)(C2H5) A-10 S c-Pr A-10 CH2 C(CH3)3 A-10 CH2 CH(CH3)2 A-10 CH2 CH(CH3)(C2H5) A-10 CH2 c-Pr A-10 O C(CH3)3 A-10 O CH(CH3)2 A-10 O CH(CH3)(C2H5) A-10 O c-Pr A-11 S C(CH3)3 A-4 CH2 CH(CH3)(C2H5) A-4 CH2 c-Pr A-4 O C(CH3)2 A-4 O CH(CH3)2 A-4 O CH(CH3)(C2H5) A-4 O c-Pr A-7 S C(CH3)3 A-7 S CH(CH3)2 A-7 S CH(CH3)(C2H5) A-7 S c-Pr A-7 CH2 C(CH3)3 A-7 CH2 CH(CH3)2 A-7 CH2 CH(CH3)(C2H5) A-7 CH2 c-Pr A-7 O C(CH3)3 A-7 O CH(CH3)2 A-7 O CH(CH3)(C2H5) A-7 O c-Pr A-11 CH2 CH(CH3)(C2H5) A-11 CH2 c-Pr A-11 O C(CH3)3 A-11 O CH(CH3)2 A-11 O CH(CH3)(C2H5) A-11 O c-Pr A-13 S C(CH3)3 A-13 S CH(CH3)2 A-13 S CH(CH3)(C2H5) A-13 S c-Pr A-13 CH2 C(CH3)3 A-13 CH2 CH(CH3)2 A-13 CH2 CH(CH3)(C2H5) A-11 S CH(CH3)2 A-11 S CH(CH3)(C2H5) A-11 S c-Pr A-11 CH2 C(CH3)3 A-11 CH2 CH(CH3)2 A-15 S C(CH3)3 A-15 S CH(CH3)2 A-15 S CH(CH3)(C2H5) A-15 S c-Pr A-15 CH2 C(CH3)3 A-15 CH2 CH(CH3)2 A-17 S C(CH3)3 A-17 S CH(CH3)2 A-17 S CH(CH3)(C2H5) A-17 S c-Pr A-17 CH2 C(CH3)3 A-17 CH2 CH(CH3)2 A-17 CH2 CH(CH3)(C2H5) A-17 CH2 c-Pr A-17 O C(CH3)3 A-17 O CH(CH3)2 A-17 O CH(CH3)(C2H5) A-17 O c-Pr A-18 S C(CH3)3 A-18 S CH(CH3)2 A-18 S CH(CH3)(C2H5) A-18 S c-Pr A-18 CH2 C(CH3)3 A-18 CH2 CH(CH3)2 A-22 S C(CH3)3 A-22 S CH(CH3)2 A-22 S CH(CH3)(C2H5) A-22 S c-Pr A-22 CH2 C(CH3)3 A-22 CH2 CH(CH3)2 A-22 CH2 CH(CH3)(C2H5) A-13 CH2 c-Pr A-13 O C(CH3)3 A-13 O CH(CH3)2 A-13 O CH(CH3)(C2H5) A-13 O c-Pr A-15 CH2 CH(CH3)(C2H5) A-15 CH2 c-Pr A-15 O C(CH3)3 A-15 O CH(CH3)2 A-15 O CH(CH3)(C2H5) A-15 O c-Pr A-16 S C(CH3)3 A-16 S CH(CH3)2 A-16 S CH(CH3)(C2H5) A-16 S c-Pr A-16 CH2 C(CH3)3 A-16 CH2 CH(CH3)2 A-16 CH2 CH(CH3)(C2H5) A-16 CH2 c-Pr A-16 O C(CH3)3 A-16 O CH(CH3)2 A-16 O CH(CH3)(C2H5) A-16 O c-Pr A-18 CH2 CH(CH3)(C2H5) A-18 CH2 c-Pr A-18 O C(CH3)3 A-18 O CH(CH3)2 A-18 O CH(CH3)(C2H5) A-18 O c-Pr A-19 S C(CH3)3 A-19 S CH(CH3)2 A-19 S CH(CH3)(C2H5) A-19 S c-Pr A-19 CH2 C(CH3)3 A-19 CH2 CH(CH3)2 A-19 CH2 CH(CH3)(C2H5) A-22 CH2 c-Pr A-22 O C(CH3)3 A-22 O CH(CH3)2 A-22 O CH(CH3)(C2H5) A-22 O c-Pr A-23 S C(CH3)3 A-23 S CH(CH3)2 A-23 S CH(CH3)(C2H5) A-23 S c-Pr A-23 CH2 C(CH3)3 A-23 CH2 CH(CH3)2 A-25 S C(CH3)3 A-25 S CH(CH3)2 A-25 S CH(CH3)(C2H5) A-25 S c-Pr A-25 CH2 C(CH3)3 A-25 CH2 CH(CH3)2 A-25 CH2 CH(CH3)(C2H5) A-25 CH2 c-Pr A-25 O C(CH3)3 A-25 O CH(CH3)2 A-25 O CH(CH3)(C2H5) A-25 O c-Pr A-26 S C(CH3)3 A-26 S CH(CH3)2 A-26 S CH(CH3)(C2H5) A-26 S c-Pr A-26 CH2 C(CH3)3 A-26 CH2 CH(CH3)2 A-28 S C(CH3)3 A-28 S CH(CH3)2 A-28 S CH(CH3)(C2H5) A-28 S c-Pr A-28 CH2 C(CH3)3 A-28 CH2 CH(CH3)2 A-28 CH2 CH(CH3)(C2H5) A-19 CH2 c-Pr A-19 O C(CH3)3 A-19 O CH(CH3)2 A-19 O CH(CH3)(C2H5) A-19 O c-Pr A-23 CH2 CH(CH3)(C2H5) A-23 CH2 c-Pr A-23 O C(CH3)3 A-23 O CH(CH3)2 A-23 O CH(CH3)(C2H5) A-23 O c-Pr A-24 S C(CH3)3 A-24 S CH(CH3)2 A-24 S CH(CH3)(C2H5) A-24 S c-Pr A-24 CH2 C(CH3)3 A-24 CH2 CH(CH3)2 A-24 CH2 CH(CH3)(C2H5) A-24 CH2 c-Pr A-24 O C(CH3)3 A-24 O CH(CH3)2 A-24 O CH(CH3)(C2H5) A-24 O c-Pr A-26 CH2 CH(CH3)(C2H5) A-26 CH2 c-Pr A-26 O C(CH3)3 A-26 O CH(CH3)2 A-26 O CH(CH3)(C2H5) A-26 O c-Pr A-27 S C(CH3)3 A-27 S CH(CH3)2 A-27 S CH(CH3)(C2H5) A-27 S c-Pr A-27 CH2 C(CH3)3 A-27 CH2 CH(CH3)2 A-27 CH2 CH(CH3)(C2H5) A-28 CH2 c-Pr A-28 O C(CH3)3 A-28 O CH(CH3)2 A-28 O CH(CH3)(C2H5) A-28 O c-Pr A-30 S C(CH3)3 A-30 S CH(CH3)2 A-30 S CH(CH3)(C2H5) A-30 S c-Pr A-30 CH2 C(CH3)3 A-30 CH2 CH(CH3)2 A-33 S C(CH3)3 A-33 S CH(CH3)2 A-33 S CH(CH3)(C2H5) A-33 S c-Pr A-33 CH2 C(CH3)3 A-33 CH2 CH(CH3)2 A-33 CH2 CH(CH3)(C2H5) A-33 CH2 c-Pr A-33 O C(CH3)3 A-33 O CH(CH3)2 A-33 O CH(CH3)(C2H5) A-33 O c-Pr A-35 S C(CH3)3 A-35 S CH(CH3)2 A-35 S CH(CH3)(C2H5) A-35 S c-Pr A-35 CH2 C(CH3)3 A-35 CH2 CH(CH3)2 A-38 S C(CH3)3 A-38 S CH(CH3)2 A-38 S CH(CH3)(C2H5) A-38 S c-Pr A-38 CH2 C(CH3)3 A-38 CH2 CH(CH3)2 A-38 CH2 CH(CH3)(C2H5) A-27 CH2 c-Pr A-27 O C(CH3)3 A-27 O CH(CH3)2 A-27 O CH(CH3)(C2H5) A-27 O c-Pr A-30 CH2 CH(CH3)(C2H5) A-30 CH2 C-Pr A-30 O C(CH3)3 A-30 O CH(CH3)2 A-30 O CH(CH3)(C2H5) A-30 O c-Pr A-31 S C(CH3)3 A-31 S CH(CH3)2 A-31 S CH(CH3)(C2H5) A-31 S c-Pr A-31 CH2 C(CH3)3 A-31 CH2 CH(CH3)2 A-31 CH2 CH(CH3)(C2H5) A-31 CH2 c-Pr A-31 O C(CH3)3 A-31 O CH(CH3)2 A-31 O CH(CH3)(C2H5) A-31 O c-Pr A-35 CH2 CH(CH3)(C2H5) A-35 CH2 c-Pr A-35 O C(CH3)3 A-35 O CH(CH3)2 A-35 O CH(CH3)(C2H5) A-35 O c-Pr A-37 S C(CH3)3 A-37 S CH(CH3)2 A-37 S CH(CH3)(C2H5) A-37 S c-Pr A-37 CH2 C(CH3)3 A-37 CH2 CH(CH3)2 A-37 CH2 CH(CH3)(C2H5) A-38 CH2 c-Pr A-38 O C(CH3)3 A-38 O CH(CH3)2 A-38 O CH(CH3)(C2H5) A-38 O c-Pr A-39 S C(CH3)3 A-39 S CH(CH3)2 A-39 S CH(CH3)(C2H5) A-39 S c-Pr A-39 CH2 C(CH3)3 A-39 CH2 CH(CH3)2 A-40 CH2 CH(CH3)(C2H5) A-40 CH2 c-Pr A-40 O C(CH3)3 A-40 O CH(CH3)2 A-40 O CH(CH3)(C2H5) A-40 O c-Pr A-41 S C(CH3)3 A-41 S CH(CH3)2 A-41 S CH(CH3)(C2H5) A-41 S c-Pr A-41 CH2 C(CH3)3 A-41 CH2 CH(CH3)2 A-42 S C(CH3)3 A-42 S CH(CH3)2 A-42 S CH(CH3)(C2H5) A-42 S c-Pr A-42 CH2 C(CH3)3 A-42 CH2 CH(CH3)2 A-44 S C(CH3)3 A-44 S CH(CH3)2 A44 S CH(CH3)(C2H5) A-44 S c-Pr A-44 CH2 C(CH3)3 A-44 CH2 CH(CH3)2 A-45 S C(CH3)3 A-37 CH2 c-Pr A-37 O C(CH3)3 A-37 O CH(CH3)2 A-37 O CH(CH3)(C2H5) A-37 O c-Pr A-39 CH2 CH(CH3)(C2H5) A-39 CH2 c-Pr A-39 O C(CH3)3 A-39 O CH(CH3)2 A-39 O CH(CH3)(C2H5) A-39 O c-Pr A-40 S C(CH3)3 A-40 S CH(CH3)2 A-40 S CH(CH3)(C2H5) A-40 S c-Pr A-40 CH2 C(CH3)3 A-40 CH2 CH(CH3)2 A-41 CH2 CH(CH3)(C2H5) A-41 CH2 c-Pr A-41 O C(CH3)3 A-41 O CH(CH3)2 A-41 O CH(CH3)(C2H5) A-41 O c-Pr A-42 CH2 CH(CH3)(C2H5) A-42 CH2 c-Pr A-42 O C(CH3)3 A-42 O CH(CH3)2 A-42 O CH(CH3)(C2H5) A-42 O c-Pr A-44 CH2 CH(CH3)(C2H5) A-44 CH2 c-Pr A-44 O C(CH3)3 A-44 O CH(CH3)2 A-44 O CH(CH3)(C2H5) A-44 O c-Pr A-45 CH2 CH(CH3)(C2H5) A-45 S CH(CH3)2 A-45 S CH(CH3)(C2H5) A-45 S c-Pr A-45 CH2 C(CH3)3 A-45 CH2 CH(CH3)2 A-48 S C(CH3)3 A-48 S CH(CH3)2 A-48 S CH(CH3)(C2H5) A-48 S c-Pr A-48 CH2 C(CH3)3 A-48 CH2 CH(CH3)2 A-49 S C(CH3)3 A-49 S CH(CH3)2 A-49 S CH(CH3)(C2H5) A-49 S c-Pr A-49 CH2 C(CH3)3 A-49 CH2 CH(CH3)2 A-50 S C(CH3)3 A-50 S CH(CH3)2 A-50 S CH(CH3)(C2H5) A-50 S c-Pr A-50 CH2 C(CH3)3 A-50 CH2 CH(CH3)2 A-51 S C(CH3)3 A-51 S CH(CH3)2 A-51 S CH(CH3)(C2H5) A-51 S c-Pr A-51 CH2 C(CH3)3 A-51 CH2 CH(CH3)2 A-52 S C(CH3)3 A-52 S CH(CH3)2 A-52 S CH(CH3)(C2H5) A-52 S c-Pr A-52 CH2 C(CH3)3 A-52 CH2 CH(CH3)2 A-53 S (CH3)3 A-45 CH2 c-Pr A-45 O C(CH3)3 A-45 O CH(CH3)2 A-45 O CH(CH3)(C2H5) A-45 O c-Pr A-48 CH2 CH(CH3)(C2H5) A-48 CH2 c-Pr A-48 O C(CH3)3 A-48 O CH(CH3)2 A-48 O CH(CH3)(C2H5) A-48 O c-Pr A-49 CH2 CH(CH3)(C2H5) A-49 CH2 c-Pr A-49 O C(CH3)3 A-49 O CH(CH3)2 A-49 O CH(CH3)(C2H5) A-49 O c-Pr A-50 CH2 CH(CH3)(C2H5) A-50 CH2 c-Pr A-50 O C(CH3)3 A-50 O CH(CH3)2 A-50 O CH(CH3)(C2H5) A-50 O c-Pr A-51 CH2 CH(CH3)(C2H5) A-51 CH2 c-Pr A-51 O C(CH3)3 A-51 O CH(CH3)2 A-51 O CH(CH3)(C2H5) A-51 O c-Pr A-52 CH2 CH(CH3)(C2H5) A-52 CH2 c-Pr A-52 O C(CH3)3 A-52 O CH(CH3)2 A-52 O CH(CH3)(C2H5) A-52 O c-Pr A-53 CH2 CH(CH3)(C2H5) A-53 S CH(CH3)2 A-53 S CH(CH3)(C2H5) A-53 S c-Pr A-53 CH2 C(CH3)3 A-53 CH2 CH(CH3)2 A-54 S C(CH3)3 A-54 S CH(CH3)2 A-54 S CH(CH3)(C2H5) A-54 S c-Pr A-54 CH2 C(CH3)3 A-54 CH2 CH(CH3)2 A-55 S C(CH3)3 A-55 S CH(CH3)2 A-55 S CH(CH3)(C2H5) A-55 S c-Pr A-55 CH2 C(CH3)3 A-55 CH2 CH(CH3)2 A-56 S C(CH3)3 A-56 S CH(CH3)2 A-56 S CH(CH3)(C2H5) A-56 S c-Pr A-56 CH2 C(CH3)3 A-56 CH2 CH(CH3)2 A-57 S C(CH3)3 A-57 S CH(CH3)2 A-57 S CH(CH3)(C2H5) A-57 S c-Pr A-57 CH2 C(CH3)3 A-57 CH2 CH(CH3)2 A-58 S C(CH3)3 A-58 S CH(CH3)2 A-58 S CH(CH3)(C2H5) A-58 S c-Pr A-58 CH2 C(CH3)3 A-58 CH2 CH(CH3)2 A-61 S C(CH3)3 A-53 CH2 c-Pr A-53 O C(CH3)3 A-53 O CH(CH3)2 A-53 O CH(CH3)(C2H5) A-53 O c-Pr A-54 CH2 CH(CH3)(C2H5) A-54 CH2 c-Pr A-54 O C(CH3)3 A-54 O CH(CH3)2 A-54 O CH(CH3)(C2H5) A-54 O c-Pr A-55 CH2 CH(CH3)(C2H5) A-55 CH2 c-Pr A-55 O C(CH3)3 A-55 O CH(CH3)2 A-55 O CH(CH3)(C2H5) A-55 O c-Pr A-56 CH2 CH(CH3)(C2H5) A-56 CH2 c-Pr A-56 O C(CH3)3 A-56 O CH(CH3)2 A-56 O CH(CH3)(C2H5) A-56 O c-Pr A-57 CH2 CH(CH3)(C2H5) A-57 CH2 c-Pr A-57 O C(CH3)3 A-57 O CH(CH3)2 A-57 O CH(CH3)(C2H5) A-57 O c-Pr A-58 CH2 CH(CH3)(C2H5) A-58 CH2 c-Pr A-58 O C(CH3)3 A-58 O CH(CH3)2 A-58 O CH(CH3)(C2H5) A-58 O c-Pr A-61 CH2 CH(CH3)(C2H5) A-61 S CH(CH3)2 A-61 S CH(CH3)(C2H5) A-61 S c-Pr A-61 CH2 C(CH3)3 A-61 CH2 CH(CH3)2 A-63 S C(CH3)3 A-63 S CH(CH3)2 A-63 S CH(CH3)(C2H5) A-63 S c-Pr A-63 CH2 C(CH3)3 A-63 CH2 CH(CH3)2 A-64 S C(CH3)3 A-64 S CH(CH3)2 A-64 S CH(CH3)(C2H5) A-64 S c-Pr A-64 CH2 C(CH3)3 A-64 CH2 CH(CH3)2 A-65 S C(CH3)3 A-65 S CH(CH3)2 A-65 S CH(CH3)(C2H5) A-65 S c-Pr A-65 CH2 C(CH3)3 A-65 CH2 CH(CH3)2 A-86 S C(CH3)3 A-86 S CH(CH3)2 A-86 S CH(CH3)(C2H5) A-86 S c-Pr A-86 CH2 C(CH3)3 A-86 CH2 CH(CH3)2 A-87 S C(CH3)3 A-87 S CH(CH3)2 A-87 S CH(CH3)(C2H5) A-87 S c-Pr A-87 CH2 C(CH3)3 A-87 CH2 CH(CH3)2 A-88 S C(CH3)3 A-61 CH2 C-Pr A-61 O C(CH3)3 A-61 O CH(CH3)2 A-61 O CH(CH3)(C2H5) A-61 O c-Pr A-63 CH2 CH(CH3)(C2H5) A-63 CH2 C-Pr A-63 O C(CH3)3 A-63 O CH(CH3)2 A-63 O CH(CH3)(C2H5) A-63 O c-Pr A-64 CH2 CH(CH3)(C2H5) A-64 CH2 c-Pr A-64 O C(CH3)3 A-64 O CH(CH3)2 A-64 O CH(CH3)(C2H5) A-64 O c-Pr A-65 CH2 CH(CH3)(C2H5) A-65 CH2 c-Pr A-65 O C(CH3)3 A-65 O CH(CH3)2 A-65 O CH(CH3)(C2H5) A-65 O c-Pr A-86 CH2 CH(CH3)(C2H5) A-86 CH2 c-Pr A-86 O C(CH3)3 A-86 O CH(CH3)2 A-86 O CH(CH3)(C2H5) A-86 O c-Pr A-87 CH2 CH(CH3)(C2H5) A-87 CH2 c-Pr A-87 O C(CH3)3 A-87 O CH(CH3)2 A-87 O CH(CH3)(C2H5) A-87 O c-Pr A-88 CH2 CH(CH3)(C2H5) A-88 S CH(CH3)2 A-88 S CH(CH3)(C2H5) A-88 S c-Pr A-88 CH2 C(CH3)3 A-88 CH2 CH(CH3)2 A-89 S C(CH3)3 A-89 S CH(CH3)2 A-89 S CH(CH3)(C2H5) A-89 S c-Pr A-89 CH2 C(CH3)3 A-89 CH2 CH(CH3)2 A-90 S C(CH3)3 A-90 S CH(CH3)2 A-90 S CH(CH3)(C2H5) A-90 S c-Pr A-90 CH2 C(CH3)3 A-90 CH2 CH(CH3)2 A-88 CH2 c-Pr A-88 O C(CH3)3 A-88 O CH(CH3)2 A-88 O CH(CH3)(C2H5) A-88 O c-Pr A-89 CH2 CH(CH3)(C2H5) A-89 CH2 c-Pr A-89 O C(CH3)3 A-89 O CH(CH3)2 A-89 O CH(CH3)(C2H5) A-89 O c-Pr A-90 CH2 CH(CH3)(C2H5) A-90 CH2 c-Pr A-90 O C(CH3)3 A-90 O CH(CH3)2 A-90 O CH(CH3)(C2H5) A-90 O c-Pr

TABLE 1E A W Z R1 R2b A-1 C(CH3)2 S C(CH3)3 H A-1 C(CH3)2 S CH(CH3)2 H A-1 C(CH3)2 S CH(CH3)(C2H5) H A-1 C(CH3)2 S c-Pr H A-1 C(CH3)2 CH2 C(CH3)3 H A-1 C(CH3)2 CH2 CH(CH3)2 H A-1 C(CH3)2 CH2 CH(CH3)(C2H5) H A-1 C(CH3)2 CH2 c-Pr H A-1 C(CH3)2 O C(CH3)3 H A-1 C(CH3)2 O CH(CH3)2 H A-1 C(CH3)2 O CH(CH3) (C2H5) H A-1 C(CH3)2 O c-Pr H A-5 C(CH3)2 S C(CH3)3 H A-5 C(CH3)2 S CH(CH3)2 H A-5 C(CH3)2 S CH(CH3)(C2H5) H A-5 C(CH3)2 S c-Pr H A-5 C(CH3)2 CH2 C(CH3)3 H A-5 C(CH3)2 CH2 CH(CH3)2 H A-5 C(CH3)2 CH2 CH(CH3)(C2H5) H A-5 C(CH3)2 CH2 c-Pr H A-5 C(CH3)2 O C(CH3)3 H A-5 C(CH3)2 O CH(CH3)2 H A-5 C(CH3)2 O CH(CH3)(C2H5) H A-5 C(CH3)2 O c-Pr H A-1 C(CH3)2 S C(CH3)3 CH3 A-1 C(CH3)2 S CH(CH3)2 CH3 A-1 C(CH3)2 S CH(CH3)(C2H5) CH3 A-1 C(CH3)2 S c-Pr CH3 A-1 C(CH3)2 CH2 C(CH3)3 CH3 A-1 C(CH3)2 CH2 CH(CH3)2 CH3 A-1 C(CH3)2 CH2 CH(CH3)(C2H5) CH3 A-1 C(CH3)2 CH2 c-Pr CH3 A-1 C(CH3)2 O C(CH3)3 CH3 A-1 C(CH3)2 O CH(CH3)2 CH3 A-1 C(CH3)2 O CH(CH3)(C2H5) CH3 A-1 C(CH3)2 O c-Pr CH3 A-1 CH(CH3) S C(CH3)3 H A-1 CH(CH3) S CH(CH3)2 H A-1 CH(CH3) S CH(CH3)(C2H5) H A-1 CH(CH3) S CH(C2H5)2 H A-1 CH(CH3) S c-Pr H A-1 CH(CH3) S 1-Me-c-Pr H A-1 CH(CH3) S c-Bu H A-1 CH(CH3) S 1-Me-2,2-di-Cl-c-Pr H A-1 CH(CH3) S c-Pentyl H A-1 CH(CH3) S c-Hexyl H A-1 CH(CH3) S N(CH3)2 H A-1 CH(CH3) S SCH3 H A-1 CH(CH3) S SCH(CH3)2 H A-1 CH(CH3) CH2 C(CH3)3 CH3 A-1 CH(CH3) CH2 CH(CH3)2 CH3 A-1 CH(CH3) CH2 CH(CH3)(C2H5) CH3 A-1 CH(CH3) CH2 CH(C2H5)2 CH3 A-1 CH(CH3) CH2 c-Pr CH3 A-1 CH(CH3) CH2 1-Me-c-Pr CH3 A-1 CH(CH3) CH2 c-Bu CH3 A-1 CH(CH3) CH2 1-Me-2,2-di-Cl-c-Pr CH3 A-1 CH(CH3) CH2 c-Pentyl CH3 A-1 CH(CH3) CH2 c-Hexyl CH3 A-1 CH(CH3) O C(CH3)3 H A-1 CH(CH3) O CH(CH3)2 H A-1 CH(CH3) O CH(CH3)(C2H5) H A-1 CH(CH3) O CH(C2H5)2 H A-1 CH(CH3) O c-Pr H A-1 CH(CH3) O 1-Me-c-Pr H A-1 CH(CH3) O c-Bu H A-1 CH(CH3) O 1-Me-2,2-di-Cl-c-Pr H A-1 CH(CH3) O c-Pentyl H A-1 CH(CH3) O c-Hexyl H A-1 CH(CH3) O N(CH3)2 H A-1 CH(CH3) CH2 N(CH3)2 H A-5 CH(CH3) S C(CH3)3 H A-5 CH(CH3) S CH(CH3)2 H A-5 CH(CH3) S CH(CH3)(C2H5) H A-5 CH(CH3) S CH(C2H5)2 H A-5 CH(CH3) S c-Pr H A-5 CH(CH3) S 1-Me-c-Pr H A-s CH(CH3) S c-Bu H A-5 CH(CH3) S 1-Me-2,2-di-Cl-c-Pr H A-5 CH(CH3) S c-Pentyl H A-5 CH(CH3) S c-Hexyl H A-5 CH(CH3) S N(CH3)2 H A-5 CH(CH3) S SCH3 H A-5 CH(CH3) S SCH(CH3)2 H A-5 CH(CH3) CH2 C(CH3)3 CH3 A-5 CH(CH3) CH2 CH(CH3)2 CH3 A-5 CH(CH3) CH2 CH(CH3)(C2H5) CH3 A-5 CH(CH3) CH2 CH(C2H5)2 CH3 A-5 CH(CH3) CH2 c-Pr CH3 A-5 CH(CH3) CH2 1-Me-c-Pr CH3 A-5 CH(CH3) CH2 c-Bu CH3 A-5 CH(CH3) CH2 1-Me-2,2-di-C1-c-Pr CH3 A-5 CH(CH3) CH2 c-Pentyl CH3 A-5 CH(CH3) CH2 c-Hexyl CH3 A-5 CH(CH3) O C(CH3)3 H A-5 CH(CH3) O CH(CH3)2 H A-5 CH(CH3) O CH(CH3)(C2H5) H A-5 CH(CH3) O CH(C2H5)2 H A-5 CH(CH3) O c-Pr H A-5 CH(CH3) O 1-Me-c-Pr H A-5 CH(CH3) O c-Bu H A-5 CH(CH3) O 1-Me-2,2-di-Cl-c-Pr H A-5 CH(CH3) O c-Pentyl H A-5 CH(CH3) O c-Hexyl H A-5 CH(CH3) O N(CH3)2 H A-5 CH(CH3) CH2 N(CH3)2 H A-29 CH(CH3) S C(CH3)3 H A-29 CH(CH3) S CH(CH3)2 H A-29 CH(CH3) S CH(CH3)(C2H5) H A-29 CH(CH3) S CH(C2H5)2 H A-29 CH(CH3) S c-Pr H A-29 CH(CH3) S 1-Me-c-Pr H A-29 CH(CH3) S c-Bu H A-29 CH(CH3) S 1-Me-2,2-di-Cl-c-Pr H A-29 CH(CH3) S c-Pentyl H A-29 CH(CH3) S c-Hexyl H A-29 CH(CH3) S N(CH3)2 H A-29 CH(CH3) S SCH3 H A-29 CH(CH3) S SCH(CH3)2 H A-29 CH(CH3) CH2 C(CH3)3 H A-29 CH(CH3) CH2 CH(CH3)2 H A-29 CH(CH3) CH2 CH(CH3)(C2H5) H A-29 CH(CH3) CH2 CH(C2H5)2 H A-29 CH(CH3) CH2 c-Pr H A-29 CH(CH3) CH2 1-Me-c-Pr H A-29 CH(CH3) CH2 c-Bu H A-29 CH(CH3) CH2 1-Me-2,2-di-Cl-c-Pr H A-29 CH(CH3) CH2 c-Pentyl H A-29 CH(CH3) CH2 c-Hexyl H A-29 CH(CH3) O C(CH3)3 H A-29 CH(CH3) O CH(CH3)2 H A-29 CH(CH3) O CH(CH3)(C2H5) H A-29 CH(CH3) O CH(C2H5)2 H A-29 CH(CH3) O c-Pr H A-29 CH(CH3) O 1-Me-c-Pr H A-29 CH(CH3) O c-Bu H A-29 CH(CH3) O 1-Me-2,2-di-Cl-c-Pr H A-29 CH(CH3) O c-Pentyl H A-29 CH(CH3) O c-Hexyl H A-29 CH(CH3) O N(CH3)2 H A-29 CH(CH3) CH2 N(CH3)2 H A-1 CH2CH2 S C(CH3)3 H A-1 CH2CH2 S CH(CH3)2 H A-1 CH2CH2 S CH(CH3)(C2H5) H A-1 CH2CH2 S c-Pr H A-1 CH2CH2 CH2 C(CH3)3 H A-1 CH2CH2 CH2 CH(CH3)2 H A-1 CH2CH2 CH2 CH(CH3)(C2H5) H A-1 CH2CH2 CH2 c-Pr H A-1 CH2CH2 O C(CH3)3 H A-1 CH2CH2 O CH(CH3)2 H A-1 CH2CH2 O CH(CH3)(C2H5) H A-1 CH2CH2 O c-Pr H A-5 CH2CH2 S C(CH3)3 H A-5 CH2CH2 S CH(CH3)2 H A-5 CH2CH2 S CH(CH3)(C2H5) H A-5 CH2CH2 S c-Pr H A-5 CH2CH2 CH2 C(CH3)3 H A-5 CH2CH2 CH2 CH(CH3)2 H A-5 CH2CH2 CH2 CH(CH3)(C2H5) H A-5 CH2CH2 CH2 c-Pr H A-5 CH2CH2 O C(CH3)3 H A-5 CH2CH2 O CH(CH3)2 H A-5 CH2CH2 O CH(CH3)(C2H5) H A-5 CH2CH2 O c-Pr H A-29 CH2CH2 S C(CH3)3 H A-29 CH2CH2 S CH(CH3)2 H A-29 CH2CH2 S CH(CH3)(C2H5) H A-29 CH2CH2 S c-Pr H A-29 CH2CH2 CH2 C(CH3)3 H A-29 CH2CH2 CH2 CH(CH3)2 H A-29 CH2CH2 CH2 CH(CH3)(C2H5) H A-29 CH2CH2 CH2 c-Pr H A-29 CH2CH2 O C(CH3)3 H A-29 CH2CH2 O CH(CH3)2 H A-29 CH2CH2 O CH(CH3)(C2H5) H A-29 CH2CH2 O c-Pr H A-1 CH2 CH2 c-Pr Cl A-1 CH2 CH2 CH(CH3)2 Cl A-1 CH2 CH2 CH(CH3)(C2H5) Cl

TABLE 2 Z R1 A is A-1; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 A is A-5; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21) A is A-29; W is CH2; R2b is H S C(CH3)3 S CH(CH3)2 S CH(CH3)(C2H5) S CH(C2H5)2 S c-Pr S 1-Me-c-Pr S c-Bu S 1-Me-2,2-di-Cl-c-Pr S c-Pentyl S c-Hexyl S N(CH3)2 S SCH3 S SCH(CH3)2 CH2 C(CH3)3 CH2 CH(CH3)2 CH2 CH(CH3)(C2H5) CH2 CH(C2H5)2 CH2 c-Pr CH2 1-Me-c-Pr CH2 c-Bu CH2 1-Me-2,2-di-Cl-c-Pr CH2 c-Pentyl CH2 c-Hexyl O C(CH3)3 O CH(CH3)2 O CH(CH3)(C2H5) O CH(C2H5)2 O c-Pr O 1-Me-c-Pr O c-Bu O 1-Me-2,2-di-Cl-c-Pr O c-Pentyl O c-Hexyl O N(CH3)2 CH2 N(CH3)2 CH2 CH(CH3)(n-C10H21)

TABLE 3 W is CH2; R2b is H A Z R1 A-1 S C(CH3)3 A-1 S CH(CH3)2 A-1 S CH(CH3)(C2H5) A-1 S c-Pr A-1 CH2 C(CH3)3 A-1 CH2 CH(CH3)2 A-1 CH2 CH(CH3)(C2H5) A-1 CH2 c-Pr A-1 O C(CH3)3 A-1 O CH(CH3l )2 A-1 O CH(CH3)(C2H5) A-1 O c-Pr A-5 S C(CH3)3 A-5 S CH(CH3)2 A-5 S CH(CH3)(C2H5) A-5 S c-Pr A-5 CH2 C(CH3)3 A-5 CH2 CH(CH3)2 A-5 CH2 CH(CH3)(C2H5) A-5 CH2 c-Pr A-5 O C(CH3)3 A-5 O CH(CH3)2 A-5 O CH(CH3)(C2H5) A-5 O c-Pr A-29 S C(CH3)3 A-29 S CH(CH3)2 A-29 S CH(CH3)(C2H5) A-29 S c-Pr A-29 CH2 C(CH3)3 A-29 CH2 CH(CH3)2 A-29 CH2 CH(CH3)(C2H5) A-29 CH2 c-Pr A-29 O C(CH3)3 A-29 O CH(CH3)2 A-29 O CH(CH3)(C2H5) A-29 O c-Pr

TABLE 4 A W Z R3 R4 A-1 CH2 S CH3 CH3 A-1 CH2 CH2 CH3 CH3 A-1 CH2 O CH3 CH3 A-1 CH2 S CH3 H A-29 CH2 CH2 CH3 CH3 A-29 CH2 O CH3 CH3 A-29 CH2 S CH3 H A-29 CH2 CH2 CH3 H A-1 CH2 CH2 CH3 H A-1 CH2 O CH3 H A-5 CH2 S CH3 CH3 A-5 CH2 CH2 CH3 CH3 A-5 CH2 O CH3 CH3 A-5 CH2 S CH3 H A-5 CH2 CH2 CH3 H A-5 CH2 O CH3 H A-29 CH2 S CH3 CH3 A-29 CH2 O CH3 H A-1 CH2 S H H A-1 CH2 CH2 H H A-1 CH2 O H H A-5 CH2 S H H A-5 CH2 CH2 H H A-5 CH2 O H H A-29 CH2 S H H A-29 CH2 CH2 H H

Formulation/Utility

Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible (“wettable”) or water-soluble. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated”). Encapsulation can control or delay release of the active ingredient. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.

The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersible and Water- 5-90 0-94 1-15 soluble Granules, Tablets and Powders. Suspensions, Emulsions, 5-50 40-95  0-15 Solutions (including Emulsifiable Concentrates) Dusts 1-25 70-99  0-5  Granules and Pellets 0.01-99     5-99.99 0-15 High Strength Compositions 90-99  0-10 0-2 

Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J., as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.

Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, propylene carbonate, dibasic esters, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol, benzyl and tetrahydrofurfuryl alcohol.

Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. Pat. No. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and World Patent Publication 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701 and U.S. Pat. No. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see T. S. Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture” in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989.

In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A1-A5 below.

EXAMPLE A

High Strength Concentrate Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%.

EXAMPLE B

Wettable Powder Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.

EXAMPLE C

Granule Compound 1 10.0% attapulgite granules (low volatile matter, 90.0%. 0.71/0.30 mm; U.S.S. No. 25-50 sieves)

EXAMPLE D

Extruded Pellet Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.

EXAMPLE E

Granule Compound 117 10.0% attapulgite granules (low volatile matter, 90.0%. 0.71/0.30 mm; U.S.S. No. 25-50 sieves)

Test results indicate that the compounds of the present invention are highly active preemergent and postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Many of the compounds of this invention, by virtue of selective metabolism in crops versus weeds, or by selective activity at the locus of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective control of grass and broadleaf weeds within a crop/weed mixture. One skilled in the art will recognize that the preferred combination of these selectivity factors within a compound or group of compounds can readily be determined by performing routine biological and/or biochemical assays. Compounds of this invention may show tolerance to important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.

As the compounds of the invention have both preemergent and postemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth, the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation.

A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is about 0.001 to about 20 kg/ha with a preferred range of about 0.004 to about 1.0 kg/ha One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.

Compounds of this invention, properly formulated for application onto agricultural land or crops, are especially useful for prevention of weed growth in cultivated rice crops such as flooded paddy rice or dryland seeded or upland rice. These general groupings of rice crop cultivation methods include transplanted (i.e. transplanted into a flooded field (paddy)), water-seeded (i.e. seeded onto a flooded field so the seeds are positioned at or near the soil surface), broadcast dry-seeded (i.e. seeded onto the surface of the soil (typically prepared by cultivation) of a dry field, which is then flooded), and dry soil planted (i.e. seeded into the soil (so that the soil covers the seeds) of a dry field) with flood (i.e. the field is subsequently flooded) or without flood (i.e. the field is not subsequently flooded, and the rice crop relies instead on natural rainfall or non-flood irrigation).

The formulated compounds of the invention can be applied (i.e. contacted to the weeds or their environment) using a variety of methods, timings, or their combination(s), which allow the user to choose that which is most appropriate for the particular rice culture. The compounds can be applied: to soil or flood waters before transplants or seed are planted; at time of transplanting or seed planting; after transplanting or seed planting; after seed planting but before crop and/or weeds emerge; or after planting and the crop and/or weeds have emerged. The compounds can be applied, for example, as a treatment spray mixture, mixed with solid fertilizer or alone, or included in irrigation water. Applications to the soil can be enhanced by shallow mixing of the compounds into the soil with tillage equipment. The compound(s), alone or in mixture, can be applied directly to flood waters of the paddy as a liquid spray, suspension concentrate, or prepared granule or dispersible solid. The compounds can be applied over the top of the rice crop to emerged weed foliage and flood waters, or as a granule that can be broadcast-distributed onto the soil surface or into the flood, or they can incorporated in the soil before planting.

Applications of the compounds of the invention can be timed to coincide with specific stages of weed and/or crop growth dependent upon the rice culture practiced. The compounds can be applied to soil or flood waters: before crops are planted, at time of planting, after the crop is planted but before emergence, or after the crop emerges.

The compounds can be applied to the paddy by various means including, but not limited to: introduction or injection at the water source; manual or mechanical-equipment aided distribution from within or upon the levees; and dispersal or delivery by boat, airplane or helicopter.

Compounds of this invention, properly formulated for application onto agricultural land or crops, are also especially useful for prevention of weed growth in nonflooded crops such as maize when applied to the soil before weeds emerge or shortly after their emergence, either before or after the crop emerges. Applications to the soil can be made before, during, or after planting, and can be enhanced by shallow mixing of the compounds into the soil with tillage equipment. The formulated compounds can be applied to the soil, for example, as a treatment spray mixture, mixed with solid fertilizer or included in irrigation water.

Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides and fungicides, and other agricultural chemicals such as fertilizers. Compounds of this invention can also be used in combination with commercial herbicide safeners such as benoxacor, dichlormid and furilazole to increase safety to certain crops. Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes. A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bifenox, bilanafos, bispyribac and its sodium salt, bromacil, bromobutide, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim butylate, cafenstrole, caloxydim (BAS 620H), carbetamide, carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl chlornitrofen, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clethodin, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cunyluron, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethofumesate, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, fluchloralin, flufenacet, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, glyphosate-sesquisodium, glyphosate-trimesium, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, isoproturon, isouron, isoxaben, isoxaflutole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its dimethylammonium, potassium and sodium salts, MCPA-isoctyl, MCPB and its sodium salt, MCPB-ethyl, mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamitron, metazachlor, methabenzthiauron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, methyl [[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]-amino]oxy]acetate (AKH-7088), methyl 5-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]-amino]sulfonyl]-1-(2-pyridinyl)-1H-pyrazole-4-carboxylate (NC-330), metobenzuron, metobromuron, metolachlor, S-metholachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pendimethalin, pentanochlor, pentoxazone, perfluidone, phenmedipham, picloram, picloram-potassium, picolinafen, piperofos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim (BAS625H, 2-[1-[[2-(4-chlorophenoxy)propoxy]imino]butyl]-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen-1-one), prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propyzamde, prosulfocarb, prosulfuron, pyraflufen-ethyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicaib, pyridate, pyrimiobac-methyl, pyrithiobac, pyrithiobac-sodium, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimufuron, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiafluamide (BAY 11390), thiazopyr, thifensulfiron-methyl, thiobencarb, tiocarbazil, tralkoxydim, tri-allate, triasulfron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron and vernolate.

Especially useful herbicide mixture partners for the compounds of the invention in rice crops are the sulfonylurea herbicides azimsulfuron, bensulfuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, cinosulfuron, cyclosulfamuron, halosulfuron-methyl, imazosulfuron and pyrazosulfuron-ethyl, and the nonsulfonylurea herbicides bispyribac-sodium, carfentrazone-ethyl, molinate, propanil, quinchlorac, thiobencarb and triclopyr. Other herbicides useful in combination with the compounds of the invention for control of undesired vegetation in rice crops include, but are not limited to, anilofos, benfuresate, benzofenap, bispyribac-sodium, bromobutid, cafenstrole, copper(II) sulfate, cyhalofop-butyl, dimepiperate, epoprodan, etobenzanid, fenoxaprop-ethyl, fentrazamide, indanofan, mefenacet, pretilachlor, profoxydim, pyrazolate, pyributicarb and thenylchlor.

To achieve complete knockdown and residual weed control in maize crops, mixtures of the Formula 1 compounds of this invention with the following herbicides may be especially useful: acetochlor, atrazine, dicamba, dimethenamid, foramsulfuron, flufenacet, flumetsulam, glyphosate, isoxaflutole, mesotrione, metolachlor, metribuzin, nicosulfuron, rimsulfuron, simazine and sulcotrione.

Combination of these companion herbicides with the novel herbicidal compounds of the invention may provide reduction of injury (i.e. safening) on crops and greater control of weeds than expected from additive effects (i.e. synergism). Daimuron and quinoclamine are examples of companion herbicides safening the novel compounds of the invention on crops and also providing greater than expected control of certain weeds. Particularly preferred are mixtures of Index Table A Compound 1 with daimuron and mixtures of Index Table A Compound 1 with quinoclamine.

The following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables A1 to B for compound descriptions. The abbreviation “Ex.” stands for “Example” and is followed by a number indicating in which example the compound is prepared.

INDEX TABLE A1* Cmpd. No. (R)p Y Z R1 R2b m.p. (° C.) 1 (Ex. 1,2) 3-CF3 O S t-C4H9 H  66-69* 2 3-CF3 O S trimethylsilyl H oil* 3 (Ex. 3) 3-CF3 O CH2 t-C4H9 H 76-78 4 3-CF3 O CH2 trimethylsilyl H 93-95 5 3-CF3 O CH2 CH(C2H5)2 H oil* 6 3-CF3 O CH2 CH(CH3)2 H oil* 7 3-CF3 O CH2 CH(CH3)(C2H5) H oil* 8 3-CF3 O CH2 cyclopropyl H oil* 9 (Ex.4) 3-CF3 O O t-C4H9 H 95-98 10 (Ex. 7) 3-CF3 O CH2 C(CH3)2CH2CH2 123-126 11 3-CF3 O CH2 CH(CH3)CH2CH2 91-92 12 3-CF3 O CH2 cyclopropyl Cl 90-92 13 3-CF3 O CH2 CH(CH3)(C2H5) Cl oil* 14 3-CF3 O CH2 t-C4H9 Cl  97-101 15 3-CF3 O CH2 H H 86-88 16 3-CF3 O CH2 CH3 H oil* 17 3-CF3 O CH2 CH(CH3)2 CH3 65-68 18 3-CF3 O S H H oil* 19 3-CF3 O S CH3 H 93-95 20 3-CF3 O S CH(CH3)(C2H5) H oil* 21 3-CF3 O S CH(C2H5)2 H oil* 22 3-CF3 S CH2 t-C4H9 H 82-85 23 3-CF3 O S CH(CH3)2 H oil* 24 3-CF3 O O CH(CH3)(C2H5) H 59-61 25 (Ex. 5) 3-CF3 O O CH(C2H5)2 H 83-85 26 3-CF3 O S cyclopropyl H oil* 27 3-CF3 O O CH(CH3)2 H oil* 28 3-CF3 O O cyclopropyl H oil* 29 3-CF3 O S(O) t-C4H9 H 156-159 30 3-OCF3 O S t-C4H9 H oil* 31 3-0CF3 O S CH(CH3)2 H oil* 32 3-OCF3 O S CH(CH3)(C2H5) H oil* 33 3-Br O CH2 t-C4H9 H oil* 34 3,4-Cl O CH2 t-C4H9 H oil* 35 3-Br-4-CH3 O CH2 t-C4H9 H oil* 36 3-OCF2H O S t-C4H9 H oil* 37 3-CF3 O S cyclobutyl H oil* 38 3-OCF3 O S cyclobutyl H oil* 39 3-CF3 O O cyclobutyl H 88-90 40 3-OCF3 O 5 CH(CH3)(C2H5) H oil* 41 3-Cl-4-CH3 O CH2 t-C4H9 H oil* 42 3-OCH3-4-CH3 O CH2 t-C4H9 H 122-124 43 3-Cl O CH2 t-C4H9 H oil* 44 3-OCF2H O S CH(CH3)2 H oil* 45 3-OCF2H O S cyclobutyl H oil* 46 3-Cl-4-F O CH2 t-C4H9 H oil* 47 3-CF3-4-CH3 O CH2 t-C4H9 H oil* 48 3-OCF2CF2H O CH2 t-C4H9 H oil* 49 3-OCF3 O CH2 t-C4H9 H oil* 50 3-OCF3 O S cyclohexyl H oil* 51 3-CF3 O O cyclohexyl H 91-94 52 3-CF3 O S cyclohexyl H oil* 53 3-CH3-4-Cl O CH2 t-C4H9 H oil* 54 3,5-di-CF3 O CH2 t-C4H9 H oil* 55 3,5-di-Cl O CH2 t-C4H9 H oil* 56 3-Br-4-Cl O CH2 t-C4H9 H oil* 57 3-OCH3 O CH2 t-C4H9 H 97-99 58 3-CF3 O CH2 OCH(CH3)(C2H5) H oil* 59 3-CF3 O CH2 OCH(CH3)2 H oil* 60 3-CF3 O CH2 OCH3 H oil* 61 3-CF3 O CH2 OCH2CH3 H oil* 62 3-CF3 O O 1-methylcyclopropyl H 65-67 63 3-OCF3 O S 1-methylcyclopropyl H 53-55 64 3-CF3 O S 1-methylcyclopropyl H 50-54 65 3-OCF3 O O CH(CH3)2 H 55-58 66 3-OCF3 O O t-C4H9 H 42-43 67 3-OCF3 O O CH(CH3)(C2H5) H 45-49 68 3-OCF3 O O CH(C2H5)2 H 35-37 69 3-OCF3 O O 1-methylcyclopropyl H 59-62 70 3-OCH(CH3)2 O CH2 t-C4H9 H 80-84 71 3,5-di-OCH3 O CH2 t-C4H9 H oil* 72 3-CO2C2H5 O CH2 t-C4H9 H oil* 73 3-CO2CH3 O CH2 t-C4H9 H oil* 74 3,5-di-Cl-4-CH3 O CH2 t-C4H9 H oil* 75 3-Br-4-F O CH2 t-C4H9 H oil* 76 3-OCF2H OCH2 t-C4H9 H oil* 77 3,4-di-CH3-5-Br O CH2 t-C4H9 H oil* 78 3-Br-4-CH3-5-F O CH2 t-C4H9 H oil* 79 3-OCF2H-4-CH3 O CH2 t-C4H9 H oil* 80 3-OCH3-4-CH3 O CH2 CH(CH3)(C2H5) H 65-68 81 3-OCH3-4-CH3 O CH2 CH(C2H5)2 H 55-57 82 3-OCH(CH3)2 O CH2 CH(CH3)2 H 50-53 83 3-OCH(CH3)2 O CH2 CH(CH3)(C2H5) H oil* 84 3-OCH(CH3)2 O CH2 CH(C2H5)2 H oil* 85 3-OCH3-4-CH3 O CH2 CH(CH3)2 H 89-91 86 3-SCH3 O CH2 t-C4H9 H 65-69 87 3-COCH3 O CH2 t-C4H9 H oil* 88 3-I O CH2 t-C4H9 H 112-114 89 3-CF3 O O CH(CH3)(CH2)2CH3 H oil* 90 3-OCF3 O S CH(CH3)(CH2)2CH3 H oil* 91 3-OCF3 O O CH(CH3)(CH2)2CH3 H oil* 92 3-CF3 O S CH(CH3)(CH2)2CH3 H oil* 93 3-SCF3 O CH2 t-C4H9 H 56-57 94 3-OC(O)CF3 O CH2 t-C4H9 H 201-203 95 3-OCH3 O CH2 CH(CH3)(C2H5) H oil* 96 3-OCH3 O CH2 CH(C2H5)2 H oil* 97 3-OCF3 O O CH(CH3)(CH2)3CH3 H oil* 98 3-CF3 O O CH(CH3)(CH2)3CH3 H oil* 99 3-OCH3 O CH2 CH(CH3)(CH2)2CH3 H oil* 100 3-CF3 O CH2 CH(CH3)(CH2)2CH3 H oil* 101 3-S(O)CF3 O CH2 t-C4H9 H oil* 102 3-S(O)2CH3 O CH2 t-C4H9 H 134-136 103 3-CF3 O S CH(CH3)(CH2)3CH3 H oil* 104 3-CN OCH2 t-C4H9 H 160-164 105 3,4-CH2CH2CH2 O CH2 t-C4H9 H 108-110 106 3-OC2H5-4-CH3 OCH2 t-C4H9 H oil* 107 3-O(CH2)2CH3-4-CH3 O CH2 t-C4H9 H oil* 108 3-C(CH2)2I-4-CH3 O CH2 t-C4H9 H oil* 109 3-O(CH2)2Cl-4-CH3 O CH2 t-C4H9 H oil* 110 3-OCH(CH3)2-4-CH3 O CH2 t-C4H9 H oil* 111 3-CH(CH3)2 O CH2 t-C4H9 H 108-110 112 3-CH3 O CH2 t-C4H9 H 118-119 113 3-OCF3 O O CH((CH2)3CH3)2 H oil* 114 3-CF3 O O CH((CH2)3CH3)2 H 52-54 115 3-OCF3 O S CH((CH2)3CH3)2 H 64-65 116 3-CF3 O S CH((CH2)3CH3)2 H 54-55 117 (Ex. 6) 3-OCH3-4-Cl O CH2 t-C4H9 H 128-130 118 3-OCH3-4-Cl O CH2 CH(C2H5)2 H oil* 119 3-OCH3-4-Cl O CH2 CH(CH3)(C2H5) H 71-74 120 3-OCH3-4-Cl O CH2 CH(CH3)2 H 93-95 121 3-OCH3-4-Cl O CH2 CH(CH3)(CH2)2CH3H 85-88 122 3-I-4-CH3 O CH2 t-C4H9 H oil* 123 3-CO2(CH2)2CH3 O CH2 t-C4H9 H oil* 124 3-CO2CH(CH3)2 O CH2 t-C4H9 H oil* 125 3-OC2H5 O CH2 CH(C2H5)2 H 81-82 126 3-OC2H5 O CH2 CH(CH3)(C2H5) H 71-72 127 3-OCH(CH3)(C2H5) O CH2 t-C4H9 H 50-51 128 3-OC2H5 O CH2 CH(CH3)2 H 78-79 129 3-OC2H5 O CH2 CH(CH3)(CH2)2CH3 H 70-71 130 3-OC2H5 O CH2 t-C4H9 H 125-126 131 3-OCF2H O O CH(C2H5)2 H oil* 132 3-OCF2H O O CH(CH3)(CH2)2CH3 H oil* 133 3-OCF2H O O t-C4H9 H 74-75 134 3-OCF2H O O CH(CH3)(C2H5) H oil* 140 3-OCH3-4-Br O CH2 CH(CH3)2 H 100-105 141 3-OCH3-4-Br O CH2 t-C4H9 H 135-137 142 3-OCH3-4-Br O CH2 CH(CH3)(C2H5) H oil* 143 3-OCH3-4-Br O CH2 CH(C2H5)2 H oil* 144 3-CF3-4-F O CH2 CH(C2H5)2 H oil* 145 3-CF3-4-F O CH2 CH(CH3)(C2H5) H oil* 146 3-CF3-4-F O CH2 t-C4H9 H oil*
*see Index Table B for 1H NMR data.

INDEX TABLE A2* Cmpd. No. (R)p Z R1 R2a R2b m.p. (° C.) 135 3-CF3 CH2 t-C4H9 H H oil*
*see Index Table B for 1H NMR data.

INDEX TABLE A3* Cmpd. No. Z R1 R2b m.p. (° C.) 136 CH2 t-C4H9 H oil*
*see Index Table B for 1H NMR data.

INDEX TABLE A4 Cmpd. No. (R)p Z R1 R2b m.p. (° C.) 137 4-CH3-6-OCH3 CH2 t-C4H9 H 120-122

INDEX TABLE A5* Cmpd. No. (R)p Z R1 R2b m.p. (° C.) 138 4,6-di-CH3 CH2 t-C4H9 H oil* 139 4-CH3 CH2 t-C4H9 H oil*
*see Index Table B for 1H NMR data.

INDEX TABLE B Cmpd. No. 1H NMR Dataa 1 δ 1.28(s, 9H), 4.75(d, 1H), 5.37(d, 1H), 5.97(s, 1H), 6.16(d, 1H), 7.45(d, 1H), 7.46-7.8(m, 4H). 2 δ 0.26(s, 9H), 4.78(d, 1H), 5.35(d, 1H), 6.13(s, 1H), 6.41(d, 1H), 7.43-7.8(m, 5H). 5 δ 0.83(t, 6H), 1.44-1.8(m, 4H), 2.44-2.6(m, 1H), 2.65-2.98(m, 2H), 3.9-4.18(m, 2H), 5.06(t, 1H), 6.08(d, 1H), 7.4-7.56(m, 3H), 7.9-8(m, 2H). 6 δ 1.25(d, 6H), 2.7-3.1(m, 3H), 3.9-4.2(m, 2H), 5.05(t, 1H), 6.17(d, 1H), 7.4-7.55(m, 3H), 7.95-8(m, 2H). 7 δ 0.87(t, 3H), 1.2(d, 3H), 1.5-1.74(m, 2H), 2.7-2.98(m, 3H), 3.95-4(m, 1H), 4.03-4.14(m, 1H), 5.05(t, 1H), 6.11(d, 1H), 7.4-7.55(m, 3H), 7.95-8(m, 2H). 8 δ 0.64-0.74(m, 2H), 0.8-0.95(m, 2H), 1.87-2(m, 1H), 2.64-3(m, 2H), 3.87-4.2(m, 2H), 5(t, 1H), 5.93(d, 1H), 7.4-7.55(m, 3H), 7.87-8(m, 2H). 13 δ 0.9(m, 3H), 1.3(m, 3H), 1.8(m, 2H), 2.8(m, 3H), 3.9(m, 1H), 4.1(m, 1H), 5.0(t, 1H), 7.4-7.6(m, 3H), 7.9(m, 2H). 16 δ 2.3(s, 3H), 2.7-3.0(m, 2H), 3.9-4.1(m, 2H), 5.0(t, 1H), 6.1(s, 1H), 7.4-7.5(m, 3H), 7.9(m, 1H), 8.0(s, 1H). 18 δ 4.8(m, 1H), 5.4(m, 1H), 6.1(s, 1H), 6.3(m, 1H), 7.5-7.7(m, 4H), 7.8-7.9(m, 2H). 20 δ 0.9(m, 3H), 1.3(m, 3H), 1.6(m, 2H), 2.8(m, 1H), 4.8(m, 1H), 5.3(m, 1H), 6.0(s, 1H), 6.1(s, 1H), 7.5-7.6(m, 3H), 7.7-7.8(m, 2H). 21 δ 0.8(m, 6H), 1.6(m, 4H), 2.5(m, 1H), 4.8(m, 1H), 5.3(m, 1H), 6.0(s, 1H), 6.1(s, 1H), 7.5-7.6(m, 3H), 7.7-7.8(m, 2H). 23 δ 1.2(d, 6H), 3.0(m, 1H), 4.8(m, 1H), 5.7(m, 1H), 6.0(s, 1H), 6.1(s, 1H), 7.5-7.6(m, 3H), 7.7-7.8(m, 2H). 26 δ 0.7(m, 2H), 0.9(m, 2H), 1.9(m, 1H), 4.8(d, 1H), 5.3(d, 1H), 5.9(s, 1H), 6.0(s, 1H), 7.5(m, 3H), 7.7-7.8(m, 2H). 27 δ 1.2(d, 6H), 2.9(m, 1H), 5.6(s, 1H), 5.8(m, 1H), 6.1(s, 1H), 6.2(m, 1H), 7.5(m, 3H), 7.9(m, 2H). 28 δ 0.7(m, 2H), 0.9(m, 2H), 1.9(m, 1H), 5.6(m, 1H), 5.8(m, 1H), 5.9(m, 1H), 6.1(m, 1H), 7.5(m, 3H), 7.9(m, 2H). 30 δ 1.28(s, 9H), 4.73(d, 1H), 5.37(d, 1H), 5.96(s, 1H), 6.17(d, 1H), 7.15-7.2(m, 1H), 7.4-7.5(m, 4H). 31 δ 1.24(d, 6H), 2.9-3.1(m, 1H), 4.78(d, 1H), 5.35(d, 1H), 6.0(s, 1H), 6.15(d, 1H), 7.15-7.2(m, 1H), 7.4-7.6(m, 4H). 32 δ 0.87(t, 3H), 1.22(d, 3H), 2.5-2.7(m, 2H), 2.7-2.9(m, 1H), 4.78(d, 1H), 5.35(d, 1H), 6.0(s, 1H), 6.1(d, 1H), 7.15-7.2(m, 1H), 7.4-7.6(m, 4H). 33 δ 1.3(s, 9H), 2.6-2.9(m, 2H), 3.8(m, 1H), 4.0(m, 1H), 5.0(t, 1H), 6.1(s, 1H), 7.2-7.3(m, 2H), 7.4(m, 1H), 7.6(m, 1H), 7.9(m, 1H). 34 δ 1.3(s, 9H), 2.6-2.9(m, 2H), 3.8(m, 1H), 4.0(m, 1H), 5.0(t, 1H), 6.2(s, 1H), 7.4(m, 2H), 7.5(m, 1H), 7.8(s, 1H). 35 δ 1.3(s, 9H), 2.4(s, 3H), 2.6-2.9(m, 2H), 3.7(m, 1H), 4.0(m, 1H), 5.0(t, 1H), 6.2(m, 1H), 7.2(m, 1H), 7.4(m, 1H), 7.6(m, 1H), 7.9(m, 1H). 36 δ 1.28(s, 9H), 4.73(d, 1H), 5.35(d, 1H), 5.96(s, 1H), 6.16(d, 1H), 6.57(t, 1H), 7.04(d, 1H), 7.3-7.5(m, 4H). 37 δ 1.8-2.4(m, 6H), 3.58(m, 1H), 4.79(d, 1H), 5.38(d, 1H), 6.02(s, 1H), 6.20(d, 1H), 7.48-7.6(m, 3H), 7.7-7.9(m, 2H). 38 δ 1.8-2.4(m, 6H), 3.55(m, 1H), 4.76(d, 1H), 5.35(d, 1H), 6.01(s, 1H), 6.20(d, 1H), 7.16(m, 1H), 7.4-7.55(m, 4H). 40 δ 0.88(t, 3H), 1.22(d, 3H), 1.5-1.7(m, 2H), 2.78(m, 1H), 4.78(d, 1H), 5.3(d, 1H), 6(s, 1H), 6.11(d, 1H), 6.53(t, 1H), 7.05(d, 1H), 7.3-7.5(m, 4H). 41 δ 1.3(s, 9H), 2.4(s, 3H), 2.6-2.9(m, 2H), 3.4(m, 1H), 4.1(m, 1H), 5.0(t, 1H), 5.2(s, 1H), 7.2(m, 1H), 7.5(m, 2H), 7.7(m, 1H). 43 δ 1.3(s, 9H), 2.6-2.9(m, 2H), 3.8(m, 1H), 4.0(m, 1H), 5.0(t, 1H), 6.2(m, 1H), 7.2(m, 1H), 7.3(m, 1H), 7.4(m, 1H), 7.6(m, 1H), 7.8(m, 1H). 44 δ 1.24(d, 6H), 2.98(m, 1H), 4.75(d, 1H), 5.33(d, 1H), 6.04(s, 1H), 6.14(d, 1H), 6.55(t, 1H), 7.05(d, 1H), 7.34-7.5(m, 4H). 45 δ 1.8-2.4(m, 6H), 3.58(m, 1H), 4.76(d, 1H), 5.32(d, 1H), 6.02(s, 1H), 6.20(d, 1H), 6.54(t, 1H), 7.05(d, 1H), 7.35-7.5(m, 4H). 46 δ 1.3(s, 9H), 2.6-2.8(m, 2H), 3.9-4.1(m, 2H), 5.3(t, 1H), 6.2(m, 1H), 7.3(t, 1H), 7.6(m, 2H), 8.0(m, 1H). 47 δ 1.3(s, 9H), 2.5(s, 3H), 2.6-2.8(m, 2H), 3.9-4.1(m, 2H), 5.3(t, 1H), 6.2(m, 1H), 7.4(m, 1H), 7.6(m, 1H), 7.8(m, 1H), 8.1(m, 1H). 48 δ 1.3(s, 9H), 2.6-2.7(m, 2H), 3.9-4.1(m, 2H), 5.3(t, 1H), 6.2(m, 1H), 7.1(m, 1H), 7.5(m, 1H), 7.6(m, 2H), 7.9(m, 1H). 49 δ 1.3(s, 9H), 2.5-2.7(m, 2H), 3.8-4.1(m, 2H), 5.3(t, 1H), 6.2(m, 1H), 7.1(m, 1H), 7.4(m, 1H), 7.6(m, 2H), 7.9(m, 1H). 50 δ 1.2-2.05(m, 10H), 2.6-2.7(m, 1H), 4.76(d, 1H), 5.32(d, 1H), 6.0(s, 1H), 6.12(d, 1H), 7.1-7.2(m, 1H), 7.4-7.55(m, 4H). 52 δ 1.2-2.1(m, 10H), 2.6-2.75(m, 1H), 4.78(d, 1H), 5.35(d, 1H), 6.0(s, 1H), 6.12(d, 1H), 7.47(d, 1H), 7.5-7.6(m, 2H), 7.7-7.9(m, 2H). 53 δ 1.3(s, 9H), 2.4(s, 3H), 2.6-2.8(m, 2H), 3.9-4.1(m, 2H), 5.3(t, 1H), 6.2(m, 1H), 7.4(m, 1H), 7.5(m, 1H), 7.6(m, 1H), 7.7(m, 1H). 54 δ 1.3(s, 9H), 2.6-2.8(m, 2H), 3.9-4.2(m, 2H), 5.3(t, 1H), 6.2(m, 1H), 7.6(m, 1H), 8.4(m, 1H). 55 δ 1.3(s, 9H), 2.6-2.8(m, 2H), 3.9-4.1(m, 2H), 5.3(t, 1H), 6.2(m, 1H), 7.3(m, 1H), 7.6(s, 1H), 7.8(m, 2H). 56 δ 1.3(s, 9H), 2.7-2.9(m, 2H), 3.9(m, 1H), 4.0(m, 1H), 5.0(t, 1H), 8.2(m, 1H), 7.4(m, 2H), 7.6(m, 1H), 8.0(m, 1H). 58 δ 0.9(m, 3H), 1.3(m, 5H), 2.7(m, 1H), 2.9(m, 1H), 3.9(m, 1H), 4.1(m, 1H), 4.4(m, 1H), 4.9(t, 1H), 5.7(s, 1H), 7.5(m, 3H), 7.9(m, 2H). 59 δ 1.3(m, 6H), 2.7(m, 1H), 2.9(m, 1H), 3.9(m, 1H), 4.1(m, 1H), 4.6(m, 1H), 4.8(t, 1H), 5.7(s, 1H), 7.5(m, 3H), 7.9(m, 2H). 60 δ 2.7(m, 1H), 2.9(m, 1H), 3.8(s, 3H), 3.9(m, 1H), 4.1(m, 1H), 4.9(t, 1H), 5.7(s, 1H), 7.5(m, 3H), 7.9(m, 2H). 61 δ 1.4(t, 3H), 2.7(m, 1H), 2.9(m, 1H), 3.9(m, 1H), 4.1(m, 3H), 4.9(t, 1H), 5.7(s, 1H), 7.5(m, 3H), 7.9(m, 2H). 71 δ 1.29(s, 9H), 2.62-2.90(m, 2H), 3.79-3.90(m, 7H), 4.0-4.08(m, 1H), 5.03(t, 1H), 6.15(d, 1H), 6.31(t, 1H), 6.93(d, 2H), 7.47(d, 1H). 72 δ 1.3-1.4(m, 12H), 2.8(m, 2H), 3.9(m, 1H), 4.1(m, 1H), 4.4(m, 2H), 6.1(m, 2H), 7.5(m, 2H), 7.9(m, 1H), 8.1(m, 2H). 73 δ 1.3(s, 9H), 2.8(m, 2H), 3.9(m, 4H), 4.1(m, 1H), 5.0(t, 1H), 6.1(m, 1H), 7.5(m, 2H), 7.8(m, 1H), 8.1(m, 2H). 74 δ 1.3(s, 9H), 2.4(s, 3H), 2.7-2.9(m, 2H), 3.8(m, 1H), 4.0(m, 1H), 5.0(t, 1H), 6.2(m, 1H), 7.5(m, 1H), 7.7(m, 2H). 75 δ 1.3(s, 9H), 2.6-2.9(m, 2H), 3.7(m, 1H), 4.0(m, 1H), 5.0(t, 1H), 6.2(m, 1H), 7.1(m, 1H), 7.4(m, 1H), 7.6(m, 1H), 7.9(m, 1H). 76 δ 1.3(s, 9H), 2.6-2.9(m, 2H), 3.8(m, 1H), 4.0(m, 1H), 5.0(t, 1H), 6.1(m, 1H), 6.9(m, 1H), 7.4(m, 1H), 7.5(m, 3H), 7.6(m, 1H). 77 δ 1.3(s, 9H), 2.3(s, 6H), 2.6-2.9(m, 2H), 3.8(m, 1H), 4.0(m, 1H), 5.0(t, 1H), 6.2(m, 1H), 7.5(m, 2H), 7.7(m, 1H). 78 δ 1.3(s, 9H), 2.3(s, 3H), 2.7-2.9(m, 2H), 3.8(m, 1H), 4.0(m, 1H), 5.0(t, 1H), 6.2(m, 1H), 7.4(m, 1H), 7.5(m, 1H), 7.7(m, 1H). 79 δ 1.3(s, 9H), 2.3(s, 3H), 2.6-2.9(m, 2H), 3.8(m, 1H), 4.0(m, 1H), 5.0(t, 1H), 6.1(m, 1H), 7.2-7.3(m, 3H), 7.4(m, 1H), 7.7(m, 1H). 83 δ 0.88(t, 3H), 1.23(d, 3H), 1.33(d, 6H), 1.5-1.7(m, 2H), 2.65-2.9(m, 3H), 3.84-3.97(m, 1H), 3.98-4.1(m, 1H), 4.5-4.65(m, 1H), 5.03(t, 1H), 6.1(d, 1H), 6.74(m, 1H), 7.1-7.55(m, 4H). 84 δ 0.83(t, 6H), 1.33(d, 6H), 1.5-1.8(m, 4H), 2.45-2.6(m, 1H), 2.65-2.9(m, 2H), 3.8-4.1(m, 2H), 4.5-4.65(m, 1H), 5.03(t, 1H), 6.07(d, 1H), 6.74(m, 1H), 7.1-7.55(m, 4H). 87 δ 1.29(s, 9H), 2.62(s, 3H), 2.65-2.92(m, 2H), 3.84-4.15(m, 2H), 5.05(t, 1H), 6.17(bs, 1H), 7.43-7.53(m, 2H), 7.78(d, 1H), 8.02(d, 1H) 8.2(s, 1H). 88 δ 1.29(s, 9H), 2.62-2.90(m, 2H), 3.80-3.90(m, 1H), 3.98-4.10(m, 1H), 5.0(t, 1H), 6.15(d, 1H), 7.11(t, 1H), 7.46(d, 1H), 7.5(d, 1H) 7.67(d, 1H). 89 δ 0.85(t, 3H), 1.17-1.65(m, 7H), 2.78-2.9(m, 1H), 5.58(d, 1H), 5.8(d, 1H), 6.07(s, 1H), 6.15(d, 1H), 7.5-7.6(m, 3H), 7.82-7.92(m, 2H). 90 δ 0.87(t, 3H), 1.17-1.65(m, 7H), 2.78-2.9(m, 1H), 4.75(d, 1H), 5.32(d, 1H), 6.0(s, 1H), 6.11(d, 1H), 7.1(m, 1H), 7.4-7.57(m, 4H). 91 δ 0.86(t, 3H), 1.17-1.65(m, 7H), 2.78-2.9(m, 1H), 5.55(bs, 1H), 5.77(bs, 1H), 6.05(s, 1H), 6.15(d, 1H), 7.14(d, 1H), 7.4-7.55(m, 3H), 7.64(s, 1H). 92 δ 0.87(t, 3H), 1.19-1.7(m, 7H), 2.78-2.97(m, 1H), 4.8(m, 1H), 5.35(d, 1H), 6.0(d, 1H), 6.11(d, 1H), 7.45-7.6(m, 3H), 7.7-7.9(m, 2H). 95 δ 0.88(t, 3H), 1.23(d, 3H), 1.47-1.74(m, 2H), 2.64-2.9(m, 3H), 3.8-4.1(m, 5H), 5.04(t, 1H), 6.11(d, 1H), 6.75(dd, 1H), 7.15(dd, 1H), 7.28(t, 1H), 7.44-7.54(m, 2H). 96 δ 0.83(t, 6H), 1.47-1.78(m, 4H), 2.47-2.6(m, 1H), 2.65-2.9(m, 2H), 3.81-4.1(m, 5H), 5.04(t, 1H), 6.07(d, 1H), 6.75(dd, 1H), 7.16(dd, 1H), 7.28(t, 1H), 7.42-7.54(m, 2H). 97 δ 0.8(m, 3H), 1.2-1.4(m, 9H), 2.8(m, 1H), 5.6(m, 1H), 5.8(m, 1H), 6.1(m, 1H), 6.2(m, 1H), 7.1(m, 1H), 7.5(m, 3H), 7.6(m, 1H). 98 δ 0.9(m, 3H), 1.2-1.4(m, 9H), 3.8(m, 1H), 5.6(m, 1H), 5.8(m, 1H), 6.1(m, 1H), 6.2(m, 1H), 7.5-7.6(m, 3H), 7.8-7.9(m, 2H). 99 δ 0.8(t, 3H), 1.2-1.6(m, 5H), 2.6-2.9(m, 3H), 3.8(s, 3H), 3.9(m, 1H), 4.01(m, 1H), 5.0(t, 1H), 6.1(m, 1H), 6.7(m, 1H), 7.1(m, 1H), 7.3(m, 1H) 7.5(m, 2H). 100 δ 0.9(m, 3H), 1.2-1.7(m, 7H), 2.7-3.0(m, 3H), 3.9(m, 1H), 4.1(m, 1H), 5.0(t, 1H), 6.1(m, 1H), 7.4-7.6(m, 3H), 7.8-8.0(m, 2H). 101 δ 1.3(s, 9H), 2.7-2.9(m, 2H), 3.9(m, 1H), 4.1(m, 1H), 5.0(t, 1H), 6.1(m, 1H), 7.5(m, 1H), 7.6(m, 2H), 8.1(m, 2H). 103 δ 0.9(m, 3H), 1.2-1.7(m, 7H), 2.9(m, 1H), 4.8(m, 1H), 5.3(m, 1H), 6.0(m, 1H), 6.1(s, 1H), 7.5-7.6(m, 3H), 7.7-7.9(m, 2H). 106 δ 1.3(s, 9H), 1.4(t, 3H), 2.2(s, 3H), 2.6-2.8(m, 2H), 3.8(m, 1H), 3.9-4.1(m, 3H), 5.0(t, 1H), 6.2.(m, 1H), 6.7(m, 1H), 7.1(m, 1H), 7.4(m, 1H), 7.6(m, 1H). 107 δ 1.0(t, 3H), 1.3(s, 9H), 1.8(m, 2H), 2.2(s, 3H), 2.6-2.8(m, 2H), 3.8-4.1(m, 4H), 5.0(t, 1H), 6.2(m, 1H), 6.8(m, 1H), 7.1(m, 1H), 7.5(m, 1H), 7.6(m, 1H). 108 δ 1.3(s, 9H), 2.2(s, 3H), 2.6-2.8(m, 2H), 3.4(m, 2H), 3.9(m, 1H), 4.0(m, 1H), 4.2(t, 2H), 5.0(t, 1H), 6.2(m, 1H), 6.8(m, 1H), 7.2(m, 1H), 7.5(m, 1H), 7.6(m, 1H). 109 δ 1.3(s, 9H), 2.2(s, 3H), 2.7-2.9(m, 2H), 3.9(m, 3H), 4.1(m, 1H), 4.3(m, 2H), 5.1(t, 1H), 6.2(m, 1H), 6.9(m, 1H), 7.2(m, 1H), 7.5(m, 1H), 7.7(m, 1H). 110 δ 1.3(m, 15H), 2.2(s, 3H), 2.7(m, 2H), 3.8(m, 1H), 4.0(m, 1H), 4.5(m, 1H), 5.0.(t, 1H), 6.2(m, 1H), 6.8(m, 1H), 7.2(m, 1H), 7.4(m, 1H), 7.6(m, 1H). 113 δ 0.8(m, 6H), 1.1-1.4(m, 8H), 1.5-1.7(m, 4H), 2.7(m, 1H), 5.5(s, 1H), 5.8(m, 1H), 6.1(d, 2H), 7.1(m, 1H), 7.5(m, 3H), 7.6(m, 1H). 118 δ 0.8(m, 6H), 1.5-1.8(m, 4H), 2.5(m, 1H), 2.7-2.9(m, 2H), 3.8-4.1(m, 5H), 5.0(t, 1H), 6.1(m, 1H), 6.8(m, 1H), 7.4(m, 1H), 7.5(m, 1H), 7.9(m, 1H). 122 δ 1.29(s, 9H), 2.41(s, 3H), 2.69-2.85(m, 2H), 3.78-3.90(m, 1H), 3.98-4.19(m, 1H), 4.0(t, 1H), 6.15(d, 1H), 7.22(d, 1H), 7.47(d, 1H) 7.6(dd, 1H); 8.10(d, 1H). 123 δ 1.0(t, 3H), 1.3(s, 9H), 1.8(m, 2H), 2.8(m, 2H), 3.9(m, 1H), 4.1(m, 1H), 4.3(t, 2H), 5.0(t, 1H), 6.2(s, 1H), 7.5(m, 2H), 7.9(m, 1H), 8.1(m, 2H). 124 δ 1.3(s, 9H), 1.4(d, 6H), 2.8(m, 2H), 3.9(m, 1H), 4.1(m, 1H), 5.0(t, 1H), 5.2(m, 1H), 6.1.(s, 1H), 7.5(m, 2H), 7.9(m, 1H), 8.1(m, 2H). 131 δ 0.8(m, 6H), 1.5-1.7(m, 4H), 2.5(m, 1H), 5.5(m, 1H), 5.8(m, 1H), 6.1(d, 2H), 7.0(m, 1H), 7.4(m, 3H), 7.5(m, 2H). 132 δ 0.8(m, 3H), 1.2-1.4(m, 7H), 2.8(m, 1H), 5.5(m, 1H), 5.8(m, 1H), 6.1(m, 1H), 6.2(m, 1H), 7.0(m, 1H), 7.4(m, 3H), 7.5(m, 2H). 134 δ 0.8(t, 3H), 1.2(d, 3H), 1.5-1.7(m, 2H), 2.7(q, 1H), 5.5(m, 1H), 5.7(m, 1H), 6.1(s, 1H), 6.2(m, 1H), 7.0(m, 1H), 7.4-7.6(m, 5H). 135 δ 1.29(s, 9H), 2.18-2.28(m, 2H), 2.64-2.9(m, 2H), 3.75-4(m, 4H), 4.97(t, 1H), 7.4-7.55(m, 2H), 7.8-8(m, 2H). 136 δ 1.3(s, 9H), 3.8(m, 2H), 3.7(m, 1H), 4.0(m, 4H), 5.1(t, 1H), 6.2(m, 1H), 7.2(m, 1H), 7.4(m, 2H), 7.7(m, 2H), 8.2(m, 1H). 138 δ 1.3(s, 9H), 2.3(s, 3H), 2.4(s, 3H), 2.5-2.7(m, 2H), 3.9(m, 1H), 4.3(m, 1H), 5.3(t, 1H), 6.2(s, 1H), 6.8(s, 1H), 7.6(s, 1H), 7.9(s, 1H). 139 δ 1.3(s, 9H), 2.4(s, 3H), 2.6-2.8(m, 2H), 4.0(m, 1H), 4.3(m, 1H), 5.3(m, 1H), 6.2(m, 1H), 7.0(m, 1H), 7.6(m, 1H), 8.2-8.3(m, 2H). 142 δ 0.87(t, 3H), 1.24(d, 3H), 1.4-1.8(m, 2H), 2.6-3.0(m, 3H), 3.8-4.1(m, 5H), 5.03(t, 1H), 6.14(m, 1H), 6.78(m, 1H), 7.5(m, 2H), 7.81(m, 1H). 143 δ 0.83(t, 6H), 1.4-1.8(m, 4H), 2.5-2.97(m, 3H), 3.8-4.1(m, 5H), 5.03(t, 1H), 6.1(m, 1H), 6.79(m, 1H), 7.5(m, 2H), 7.81(m, 1H). 144 δ 0.82(t, 6H), 1.5-1.75(m, 4H), 2.55(m, 1H), 2.7-2.97(m, 2H), 3.93(m, 1H), 4.05(m, 1H), 5.03(t, 1H), 6.08(d, 1H), 7.21(d, 1H), 7.51(d, 1H), 7.88-7.98(m, 2H). 145 δ 0.87(t, 3H), 1.22(d, 3H), 1.4-1.74(m, 2H), 2.7-3.0(m, 3H), 3.93(m, 1H), 4.05(m, 1H), 5.03(t, 1H), 6.11(d, 1H), 7.2(d, 1H), 7.5(m, 1H), 7.9-7.98(m, 2H). 146 δ 1.28(s, 9H), 2.65-2.95(m, 2H), 3.8-4.18(m, 2H), 5.03(t, 1H), 6.16(d, 1H), 7.2(m, 1H), 7.46(d, 1H), 7.8-8.0(m, 7H).
a1H NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-doublet of doublets, (dt)-doublet of triplets, (br s)-broad singlet.

Test A

Seeds of barnyardgrass (Echinochloa crus-galli), crabgrass (Digitaria spp.), giant foxtail (Setaria viridis), morningglory (Ipomoea spp.), redroot pigweed (Amaranthus retroflexus) and velvetleaf (Abutilon theophrasti) were planted into a sandy loam soil and treated preemergence by soil drench with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, these crop and weed species were also treated postemergence sprayed to runoff with test chemicals formulated in the same manner.

Plants ranged in height from two to eighteen cm and were in the one- to two-leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately eleven days, after which time all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test results.

TABLE A Postemergence Rate Rate 250 g/ha 1000 g/ha COM- Rate 500 g/ha COM- POUND COMPOUND POUND 3 1 4 5 6 7 9 10 11 12 13 14 15 16 26 27 28 88 3 Barnyardgrass 20 60 0 90 90 90 80 20 20 0 0 0 10 0 90 70 60 30 10 Crabgrass 0 10 0 10 10 10 20 10 0 0 0 0 10 10 30 20 20 20 0 Giant foxtail 0 30 0 20 60 80 30 10 0 0 0 0 10 0 50 50 80 40 10 Morningglory 10 90 0 10 0 10 10 10 10 0 0 0 30 20 20 0 10 10 10 Pigweed 60 20 20 10 40 10 20 20 70 0 20 0 0 0 40 20 20 80 10 Velvetleaf 0 10 0 0 0 30 0 0 0 0 0 0 0 0 10 0 0 0 0 Rate 2000 g/ha COMPOUND 1 4 5 6 7 9 10 11 12 13 14 15 16 26 27 28 88 Barnyardgrass 90 0 90 90 90 90 10 40 0 0 0 10 10 90 80 60 80 Crabgrass 10 0 10 20 20 10 10 10 0 0 0 10 20 20 60 40 40 Giant foxtail 30 0 20 90 100 100 10 50 0 0 0 10 30 100 90 90 90 Morningglory 90 0 10 10 10 10 20 10 0 0 0 20 20 50 20 20 30 Pigweed 90 30 80 70 80 80 100 90 0 70 20 0 0 80 80 80 100 Velvetleaf 30 0 40 0 30 40 50 0 0 0 0 10 20 10 20 50 0 Preemergence Rate 250 g/ha Rate 500 g/ha COMPOUND COMPOUND 3 1 4 5 6 7 9 10 11 12 13 14 15 16 26 Barnyardgrass 100 90 10 100 100 100 100 100 100 0 0 0 10 10 100 Crabgrass 100 90 50 100 100 100 90 90 100 0 0 0 80 100 100 Giant foxtail 100 90 10 100 100 100 100 90 100 0 20 0 50 80 100 Morningglory 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 Pigweed 100 100 70 100 100 100 100 100 100 0 80 40 30 80 100 Velvetleaf 0 10 0 20 20 20 20 20 0 0 0 0 30 10 50 Rate 500 g/ha Rate 1000 g/ha Rate 2000 g/ha COMPOUND COMPOUND COMPOUND 27 28 88 3 1 4 5 6 7 9 10 11 12 Barnyardgrass 100 100 40 100 100 80 100 100 100 100 100 100 0 Crabgrass 100 90 80 100 100 70 100 100 100 100 100 100 60 Giant foxtail 100 100 70 100 100 100 100 100 100 100 100 100 30 Morningglory 0 0 0 0 80 0 0 0 10 0 20 0 0 Pigweed 100 100 100 100 100 80 100 100 100 100 100 100 40 Velvetleaf 20 10 0 0 70 0 30 20 0 10 10 20 0 Rate 2000 g/ha COMPOUND 13 14 15 16 26 27 28 88 Barnyardgrass 10 0 10 70 100 100 100 100 Crabgrass 80 0 100 100 100 90 100 100 Giant foxtail 90 0 100 90 100 100 100 100 Morningglory 20 0 0 20 30 20 0 30 Pigweed 100 70 100 100 100 100 100 100 Velvetleaf 0 0 100 100 40 10 10 30

Test B

Seeds selected from barnyardgrass (Echinochloa crus-galli), Surinam grass (Brachiaria decumbens), cocklebur (Xanthium strumarium), corn (Zea mays), crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), pigweed (Amaranthus retroflexus), rice (Oryza sativa) and velvetleaf (Abutilon theophrasti) were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.

At the same time, plants selected from these crop and weed species and also blackgrass (Alopecurus myosuroides), wheat (Triticum aestivum) and wild oat (Avena fatua) were treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Plant species in the flooded paddy test consisted of rice (Oryza sativa), smallflower flatsedge (Cyperus difformis), duck salad (Heteranthera limosa) and barnyardgrass (Echinochloa crus-galli) grown to the 2-leaf stage for testing. Treated plants and controls were maintained in a greenhouse for 13 to 15 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

TABLE B Postemergence Rate 62 g/ha Rate 125 g/ha COMPOUND COMPOUND 9 109 125 1 2 3 4 5 6 7 8 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 Barnyardgrass 0 0 0 0 0 0 0 50 0 20 0 0 0 0 0 0 0 0 0 0 0 60 90 0 20 70 100 0 20 0 0 100 100 80 0 0 0 90 Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Surinam grass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 200 20 0 0 20 0 0 0 0 0 0 0 0 0 0 Cocklebur 10 60 30 60 20 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 20 80 70 20 40 20 60 50 0 0 0 70 60 60 0 0 40 20 Corn 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 0 0 0 0 0 0 0 50 0 0 0 0 0 0 60 50 20 0 0 0 0 20 30 40 20 60 60 0 20 20 0 50 0 80 0 0 0 80 Foxtail, Giant 0 0 0 30 0 0 0 20 0 0 0 0 0 0 0 20 0 0 0 0 0 50 20 0 20 20 20 20 0 0 0 10 0 0 0 0 0 60 Lambsquarters 70 80 100 90 80 80 50 80 0 30 30 0 0 0 0 0 0 0 80 60 10 90 100 90 80 90 100 80 50 60 0 90 70 80 70 90 0 90 Morningglory 0 90 50 50 — 0 0 0 0 0 0 0 0 0 0 30 0 0 0 10 20 60 70 30 20 0 90 0 0 0 0 40 10 20 0 0 0 30 Pigweed 70 50 30 90 0 70 20 10 0 20 0 0 0 0 — — — — 0 0 0 90 70 80 70 80 70 0 40 30 30 100 20 40 70 90 90 90 Velvetleaf 0 0 0 50 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 10 10 20 20 20 0 0 20 0 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rate 125 g/ha COMPOUND 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 Barnyardgrass 80 100 0 90 0 60 0 40 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 100 90 90 0 0 0 30 30 0 0 0 0 Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 70 0 0 0 0 0 0 0 0 Surinam grass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 30 20 0 0 0 0 0 0 0 0 0 Cocklebur 10 40 0 30 0 40 0 20 20 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 70 20 0 0 50 0 0 0 80 20 0 0 0 0 Corn 0 0 0 0 — 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 0 0 0 0 Crabgrass 0 60 0 60 0 50 0 0 0 0 0 0 0 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 50 90 0 0 0 0 0 0 0 0 0 Foxtail, Giant 60 30 0 70 0 50 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 20 0 0 0 0 20 0 0 0 0 Lambsquarters 0 80 70 70 0 70 50 20 0 0 70 0 30 70 80 0 40 0 0 80 0 0 0 0 0 60 70 60 90 90 100 80 0 0 0 0 0 70 0 0 Morningglory 20 10 0 10 0 60 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 20 20 20 0 20 0 0 Pigweed 20 60 60 40 0 80 50 0 0 0 50 0 30 0 0 0 80 0 0 90 0 0 0 0 0 50 40 0 0 0 0 0 0 30 20 20 80 50 30 70 Velvetleaf 0 0 0 0 0 50 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 30 50 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rate 125 g/ha COMPOUND 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 20 50 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Surinam grass 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Cocklebur 0 30 70 90 0 10 10 40 0 0 20 0 20 20 20 30 0 0 10 — — — — — — — — — 90 70 20 40 30 0 0 Corn 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 0 0 0 0 0 0 0 20 0 0 0 30 20 40 10 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 Foxtail, Giant 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Lambsquarters 0 0 10 20 20 10 50 30 0 0 100 90 90 90 80 80 0 80 80 80 30 0 20 0 0 0 0 0 100 90 30 90 100 0 30 Morningglory 0 30 40 80 0 0 10 0 0 0 20 0 40 0 50 10 0 10 0 0 0 0 0 0 0 0 0 0 90 50 0 100 30 0 20 Pigweed 70 70 70 70 0 0 60 60 0 0 90 60 60 80 20 0 0 20 90 0 80 0 0 0 0 0 0 0 60 20 0 70 90 0 60 Velvetleaf 0 0 40 80 0 0 0 20 0 0 0 0 10 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 50 0 0 50 50 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 40 Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 Rate 125 g/ha COMPOUND 113 114 115 116 117 118 119 120 121 122 123 124 126 127 128 129 130 131 132 133 134 136 137 138 139 140 141 142 Barnyardgrass 0 0 0 0 40 0 30 0 0 0 0 0 0 0 0 0 0 80 0 80 90 0 0 0 0 0 0 0 Blackgrass 0 0 0 0 0 0 0 0 0 — — 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Surinam grass 0 30 20 0 30 30 20 20 30 0 0 0 0 0 70 0 0 0 0 0 20 0 0 0 0 0 0 0 Cocklebur 0 50 20 30 90 60 90 90 70 30 30 20 0 0 0 0 20 30 0 10 30 0 0 0 0 60 40 60 Corn 0 0 20 20 0 20 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 40 20 20 20 30 40 40 30 30 — 0 0 0 0 0 0 0 60 0 40 20 0 0 0 0 20 20 40 Foxtail, Giant 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 30 0 0 0 0 0 30 30 Lambsquarters 30 90 0 70 90 90 90 60 80 90 0 20 100 30 0 100 90 90 70 100 100 0 0 0 0 70 90 70 Morningglory 0 30 0 30 70 40 30 50 50 20 0 0 0 0 0 0 70 20 0 0 10 0 0 10 0 0 0 70 Pigweed 100 90 50 50 80 70 60 60 50 30 0 0 30 0 0 0 80 80 0 80 60 0 0 0 0 60 80 60 Velvetleaf 0 0 0 20 70 40 30 20 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 50 40 Wheat 30 20 40 20 30 20 20 10 50 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild Oat 40 30 30 30 40 30 0 30 30 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 Rate 125 g/ha Rate 250 g/ha Rate 500 g/ha COMPOUND COMPOUND COMPOUND 143 144 145 146 9 10 109 125 1 2 3 4 5 6 7 8 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 Barnyardgrass 0 0 0 0 60 0 0 80 50 0 70 0 90 60 100 0 0 0 0 0 0 0 0 0 0 0 100 100 80 90 100 100 80 60 Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 0 0 0 0 0 0 0 20 0 0 0 0 Surinam grass 0 0 0 0 0 0 20 0 0 0 20 0 0 0 20 0 0 0 0 0 0 0 0 0 0 10 0 0 20 20 50 40 20 20 Cocklebur 0 0 0 0 20 0 70 70 80 60 30 0 20 0 0 10 0 0 0 0 0 0 0 0 20 20 90 80 20 80 40 70 60 30 Corn 0 0 0 0 0 0 0 0 60 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 50 50 60 70 10 Crabgrass 0 0 0 0 0 0 0 0 40 0 40 0 50 30 70 0 0 0 0 60 70 50 60 0 0 20 80 70 40 40 90 90 20 40 Foxtail, Giant 30 20 0 0 0 0 20 0 60 0 30 0 70 0 70 0 0 0 0 0 30 30 30 0 0 0 90 60 0 80 80 80 50 30 Lambsquarters 80 100 80 80 80 100 90 100 100 80 100 80 90 60 80 50 0 0 0 0 0 0 0 80 70 70 90 100 90 100 100 100 80 90 Morningglory 30 0 0 0 10 0 100 100 100 0 30 0 10 0 70 0 0 0 0 70 80 0 0 0 10 30 60 80 30 80 40 100 10 50 Pigweed 70 50 0 0 80 0 60 70 100 100 90 50 80 90 80 10 0 0 0 — — — — 0 0 0 90 90 90 100 100 100 60 60 Velvetleaf 50 0 0 0 0 0 80 0 60 0 0 40 10 20 50 0 0 0 0 0 0 0 0 0 20 20 20 60 30 30 0 20 20 0 Wheat 0 0 0 0 0 0 0 0 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 50 50 0 0 0 0 0 0 0 0 0 0 0 Rate 500 g/ha COMPOUND 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 58 59 60 61 62 63 64 Barnyardgrass 60 0 100 100 90 0 0 40 100 100 100 100 100 70 100 70 100 100 0 0 0 80 90 0 0 0 0 0 0 0 0 0 0 0 60 50 Blackgrass 0 0 20 0 0 0 0 0 0 0 0 0 0 0 50 0 0 0 0 0 0 60 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Surinam grass 0 0 20 0 10 0 0 0 50 0 0 0 0 0 0 0 0 0 0 0 0 90 0 0 0 0 0 0 0 0 0 0 0 0 0 40 Cocklebur 0 0 70 70 60 10 0 40 60 30 80 0 50 0 60 0 70 40 0 0 0 30 50 0 0 0 20 10 0 0 0 0 0 0 50 70 Corn 0 0 0 0 0 0 0 0 70 20 0 10 50 0 40 0 20 0 0 0 0 0 0 0 20 10 0 0 0 0 0 0 0 0 0 20 Crabgrass 30 50 100 40 100 0 0 0 100 100 100 70 90 40 80 50 40 0 0 0 0 40 50 20 0 0 0 0 0 0 0 0 0 0 60 50 Foxtail, Giant 30 0 80 20 60 20 0 0 90 80 80 0 90 0 70 0 60 0 0 0 0 0 50 0 0 0 0 0 0 0 0 0 0 0 50 30 Lambsquarters 70 20 90 80 90 80 100 80 100 90 90 90 90 60 100 80 60 0 70 90 80 50 80 90 0 80 30 0 90 0 0 0 0 60 80 80 Morningglory 0 0 90 30 20 10 0 20 40 40 20 0 20 20 100 0 0 0 0 0 0 30 0 0 0 10 20 30 10 0 0 0 0 0 40 60 Pigweed 30 30 100 60 60 80 90 90 100 90 80 90 80 80 100 80 0 0 0 50 0 30 0 80 0 90 0 0 90 0 0 0 0 40 70 70 Velvetleaf 0 20 0 0 0 0 0 0 60 0 70 0 0 0 80 0 0 0 0 0 0 40 0 0 0 0 0 0 0 0 0 0 0 0 50 30 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild Oat 0 0 0 0 0 0 0 0 20 0 0 0 0 0 40 0 0 0 0 0 0 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rate 500 g/ha COMPOUND 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 98 99 100 Barnyardgrass 100 100 100 100 90 0 0 70 90 0 0 90 0 0 0 10 0 0 0 80 50 0 30 90 80 80 90 70 0 0 30 90 0 0 0 Blackgrass 0 0 0 0 70 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Surinam grass 40 30 30 30 0 0 30 0 0 0 0 10 0 0 0 0 10 0 0 10 0 0 0 0 0 30 10 10 0 0 0 0 0 0 0 Cocklebur 30 20 60 80 20 0 20 90 90 0 0 20 20 20 30 80 100 20 10 20 100 0 0 30 30 60 80 80 50 0 20 20 — — — Corn 0 0 0 0 0 0 0 0 40 0 0 0 0 0 0 0 10 0 0 0 30 0 0 10 0 10 10 10 0 0 0 0 0 0 0 Crabgrass 100 100 100 100 30 0 30 30 50 0 0 40 0 0 0 40 30 10 0 10 50 0 0 0 60 50 90 50 0 0 20 70 20 0 0 Foxtail, Giant 0 60 40 40 0 0 20 50 50 0 0 30 0 0 0 0 0 0 0 10 20 0 0 60 70 40 40 30 0 0 0 40 20 0 0 Lambsquarters 70 90 100 100 80 0 50 0 70 0 80 40 20 10 10 90 90 70 60 60 90 50 50 100 100 100 100 90 80 20 90 90 80 70 80 Morningglory 0 0 0 0 0 30 20 50 20 0 60 20 0 0 40 90 100 10 10 30 80 0 0 70 40 70 80 50 10 0 20 50 0 0 0 Pigweed 0 0 0 0 0 0 60 60 90 90 90 80 80 80 70 80 90 10 10 70 90 0 40 100 90 90 90 60 20 10 60 90 100 0 0 Velvetleaf 0 20 20 20 0 0 20 60 70 0 50 0 0 0 0 70 90 0 0 10 50 0 0 40 0 40 30 20 10 0 0 10 20 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 0 0 0 0 0 0 0 0 0 0 0 Wild Oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 20 0 0 0 0 20 0 0 0 0 0 0 0 0 0 Rate 500 g/ha COMPOUND 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 126 127 128 129 Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 20 0 20 0 20 90 90 100 60 90 0 0 0 80 0 80 60 Blackgrass 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 60 0 0 0 0 0 — 0 — 0 0 0 0 Surinam grass 0 0 0 0 0 0 0 20 0 0 40 100 0 30 100 20 40 40 50 40 40 0 0 0 0 0 100 0 Cocklebur — — — — — 90 100 40 90 30 0 0 70 60 70 50 100 100 100 100 100 90 80 90 70 60 50 30 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 20 0 20 0 20 30 0 0 0 0 0 0 0 Crabgrass 0 0 0 0 0 0 0 0 0 0 30 30 40 30 30 40 40 40 100 70 60 0 0 0 0 0 60 0 Foxtail, Giant 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 20 0 0 50 0 0 0 0 60 0 60 0 Lambsquarters 0 0 50 0 0 100 100 80 90 90 20 30 100 100 0 90 100 100 100 90 90 100 20 40 100 50 0 100 Morningglory 0 0 0 0 0 100 70 70 100 60 0 50 30 60 0 30 100 60 80 90 70 100 0 30 50 0 0 0 Pigweed 0 0 0 0 0 90 90 40 90 70 0 80 100 100 60 70 100 70 80 80 90 70 0 30 100 0 100 60 Velvetleaf 0 0 0 0 0 80 70 60 80 70 0 0 0 0 0 30 70 70 60 50 30 0 0 20 0 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 20 40 30 30 50 20 30 20 40 20 50 0 0 0 0 0 0 0 Wild Oat 0 0 0 0 0 0 0 0 0 0 60 60 40 50 60 50 70 60 50 60 50 0 0 0 0 0 0 0 Rate 500 g/ha COMPOUND 130 131 132 133 134 136 137 138 139 140 141 142 143 144 145 146 Barnyardgrass 90 100 30 100 100 0 0 0 0 80 80 60 70 0 90 90 Blackgrass 20 0 0 0 0 0 0 0 0 0 40 0 0 0 0 0 Surinam grass 40 30 0 40 60 0 0 0 0 0 0 0 0 0 0 0 Cocklebur 50 70 0 30 30 0 0 0 0 90 100 90 100 30 0 0 Corn 0 20 0 0 20 0 0 0 0 0 0 30 0 0 0 0 Crabgrass 30 90 90 80 90 0 0 0 0 80 40 60 80 40 0 60 Foxtail, Giant 40 50 0 50 60 0 90 0 0 70 50 90 80 40 40 70 Lambsquarters 100 100 80 100 100 0 0 0 0 100 100 100 100 100 100 100 Morningglory 80 80 0 30 40 0 0 30 0 100 70 100 100 30 0 0 Pigweed 100 90 30 100 80 0 0 30 0 90 100 80 90 100 80 70 Velvetleaf 30 30 0 30 10 0 0 0 0 60 70 70 70 0 30 0 Wheat 0 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 Wild Oat 0 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Preemergence Rate 62 g/ha Rate 125 g/ha COMPOUND COMPOUND 9 10 109 125 1 2 3 4 5 6 7 8 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 Barnyardgrass 0 0 0 100 50 0 80 0 60 100 100 0 0 0 0 0 0 0 0 0 0 0 0 60 0 0 20 100 100 30 50 0 40 Surinam grass 0 20 20 70 0 0 40 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 20 30 0 20 80 40 0 0 0 40 Cocklebur 0 — 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 — 0 0 0 — 0 0 0 0 0 0 0 0 0 Corn 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 Crabgrass 0 100 100 100 0 0 70 0 90 70 70 30 0 0 0 0 0 0 0 0 0 0 0 100 0 70 100 100 100 0 20 0 20 Foxtail, Giant 30 80 20 100 50 0 40 0 80 20 70 40 0 0 0 0 0 0 0 0 0 0 70 70 30 50 90 100 100 0 20 0 70 Lambsquarters 90 100 100 100 100 80 100 0 100 100 100 0 0 0 0 0 0 0 0 — 0 0 — — 100 100 100 100 100 100 100 0 100 Morningglory 0 0 0 50 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 — 0 0 0 90 0 0 0 0 0 0 0 0 0 Pigweed 80 90 100 100 100 20 100 0 80 100 100 20 0 0 0 0 0 0 0 0 0 0 0 0 90 100 100 100 100 100 100 0 100 Rice 0 0 0 50 — — — — 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 40 0 0 0 0 Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 50 0 — — 0 0 0 0 0 0 0 0 0 0 0 0 Rate 125 g/ha COMPOUND 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 58 59 60 61 Barnyardgrass 100 80 30 0 0 100 0 70 50 100 40 100 60 80 80 0 0 0 100 0 80 0 0 0 0 0 0 0 0 0 Surinam grass 30 40 30 0 0 70 0 0 20 60 0 90 0 0 70 0 0 0 0 0 0 0 0 0 0 30 0 60 0 0 Cocklebur 0 — 0 0 0 0 0 — 0 0 0 0 — 0 0 0 0 0 0 0 0 0 — 0 0 0 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass 100 60 0 100 0 100 0 0 0 100 0 100 0 0 30 0 0 0 0 100 100 100 0 0 0 30 0 20 — 0 Foxtail, Giant 30 70 20 0 0 100 40 0 30 70 0 100 0 10 100 0 0 0 0 20 0 90 0 0 0 50 0 0 0 0 Lambsquarters 100 100 90 20 0 100 100 100 100 100 100 100 100 100 100 100 0 100 100 0 100 100 100 0 0 100 0 0 0 — Morningglory 0 0 0 0 0 0 0 0 0 0 0 80 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Pigweed 100 100 100 30 — 100 100 100 100 100 100 100 100 100 0 100 100 0 100 0 0 0 100 0 — 100 0 0 0 0 Rice 0 0 0 0 0 90 0 0 0 40 0 90 0 30 60 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 70 0 0 0 0 0 0 0 100 0 — 0 0 0 0 — 0 0 0 Rate 125 g/ha COMPOUND 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 Barnyardgrass 0 50 50 90 100 60 100 20 — 10 100 100 30 100 100 20 0 70 0 100 100 100 100 100 0 100 100 80 Surinam grass 0 0 30 0 20 20 0 20 0 40 0 50 0 60 80 0 0 70 80 90 90 70 80 60 0 80 70 60 Cocklebur 0 0 0 0 — 0 0 0 0 0 0 0 0 30 0 0 0 0 0 0 0 0 0 40 0 0 0 0 Corn 0 0 0 0 0 0 0 0 — 0 0 0 0 0 0 0 0 0 0 0 0 20 0 20 0 30 20 0 Crabgrass 0 0 40 20 0 20 — 0 90 50 100 100 20 100 100 60 0 100 100 100 100 100 100 100 0 100 100 90 Foxtail, Giant 0 50 0 20 20 40 — 0 90 90 100 100 0 100 100 0 0 0 100 100 100 100 100 80 80 100 100 90 Lambsquarters 100 100 100 100 100 100 100 90 100 100 100 100 100 100 100 90 100 100 100 100 100 100 — 100 100 100 100 100 Morningglory 0 0 0 0 — 0 0 0 20 0 0 0 0 0 0 0 0 0 60 30 0 0 0 90 0 0 0 0 Pigweed 100 100 100 100 100 100 100 60 100 100 100 100 80 100 100 90 80 100 100 100 100 100 100 100 100 100 100 90 Rice 0 0 0 0 0 40 0 0 30 20 0 30 0 50 70 0 0 50 60 50 70 20 0 100 0 70 0 0 Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 90 0 50 0 0 0 0 0 70 0 0 0 20 0 0 0 0 Rate 125 g/ha COMPOUND 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 Barnyardgrass 50 100 30 0 0 90 100 30 0 0 0 30 0 0 0 0 90 0 0 30 30 0 90 0 0 0 0 100 100 Surinam grass 20 70 0 0 0 60 50 0 0 0 0 0 0 0 0 0 100 0 0 50 0 0 10 0 0 0 0 100 0 Cocklebur 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 30 0 0 0 0 0 0 0 0 0 0 70 0 Corn 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 30 0 0 0 0 0 0 0 20 0 0 20 30 Crabgrass 90 100 50 20 0 100 100 20 0 0 0 90 0 0 0 0 100 0 0 100 100 70 100 0 0 0 0 100 100 Foxtail, Giant 80 90 50 20 0 100 100 20 0 0 0 0 0 0 0 0 40 0 0 0 0 0 100 0 0 0 0 100 40 Lambsquarters 100 100 100 60 0 100 100 20 60 100 100 100 0 100 100 60 100 100 100 100 0 30 100 0 30 0 0 100 100 Morningglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 100 0 0 0 0 0 30 0 0 0 0 80 40 Pigweed 80 90 80 0 0 100 100 0 0 0 70 40 0 0 70 0 100 80 20 100 100 0 100 0 30 0 0 100 100 Rice 0 0 0 0 0 90 70 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 40 20 Rate 250 g/ha Rate 125 g/ha COM- COMPOUND POUND 119 120 121 122 123 124 126 127 128 129 130 131 132 133 134 136 137 138 139 140 141 142 143 144 145 146 9 10 Barnyardgrass 100 100 40 0 0 70 100 0 100 100 100 100 100 100 100 0 0 0 0 100 100 100 100 80 70 90 60 100 Surinam grass 100 40 0 50 0 0 100 0 100 90 100 100 80 100 90 0 0 70 0 100 100 100 80 0 0 40 70 30 Cocklebur 30 20 10 0 0 0 50 0 0 0 0 0 0 0 0 0 0 0 — 20 70 0 0 0 0 0 0 0 Corn 0 20 20 0 0 0 30 0 30 20 50 40 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 30 Crabgrass 100 100 10 100 0 30 100 100 100 100 100 100 100 100 100 0 0 100 0 100 100 100 100 100 100 100 100 100 Foxtail, Giant 100 100 0 20 0 50 100 70 100 100 100 100 100 100 100 0 0 80 0 100 100 100 100 100 100 100 90 100 Lambsquarters 100 100 100 100 0 100 100 90 100 100 100 100 100 100 100 100 0 100 100 100 100 100 100 100 100 100 100 100 Morningglory 50 70 20 0 0 0 70 0 70 0 50 0 0 0 0 0 0 90 0 0 90 20 20 0 0 0 0 0 Pigweed 100 100 100 100 0 80 100 0 100 100 100 100 70 100 100 0 0 100 0 100 100 100 100 100 100 100 100 100 Rice 10 20 0 0 0 0 70 0 100 30 100 70 0 90 100 0 30 0 0 20 30 20 0 0 0 0 0 0 Velvetleaf 30 20 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 60 70 20 60 0 0 0 0 0 Rate 250 g/ha COM- Rate 500 g/ha POUND COMPOUND 109 125 1 2 3 4 5 6 7 8 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 Barnyardgrass 50 100 100 0 100 0 100 100 100 70 0 0 0 0 0 0 0 0 0 0 100 100 80 100 100 100 100 100 100 20 100 100 Surinam grass 90 100 0 0 70 0 20 30 20 70 0 0 0 0 0 20 0 0 0 20 0 20 50 20 80 80 70 0 70 0 60 70 Cocklebur 0 50 40 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 100 0 90 0 Corn 0 40 20 0 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 70 0 0 0 0 0 Crabgrass 100 100 100 0 100 0 100 100 100 100 0 0 0 0 0 0 0 0 0 0 — 100 100 100 100 100 100 90 100 0 100 100 Foxtail, Giant 100 100 100 0 80 0 100 100 100 90 0 0 0 0 0 0 0 0 0 0 100 100 100 50 100 100 100 90 100 0 100 90 Lambsquarters 100 100 100 90 100 0 100 100 100 100 0 0 0 0 0 60 0 0 — 60 — — 100 100 100 100 100 100 100 100 100 100 Morningglory 0 80 40 0 0 0 0 0 0 0 0 0 0 0 0 30 0 0 0 0 0 100 0 60 0 90 0 0 0 30 90 0 Pigweed 100 100 100 80 100 0 100 100 100 100 0 0 0 0 0 0 0 0 0 0 100 90 100 100 100 100 100 100 100 70 100 100 Rice 0 100 — — — — 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 0 0 80 40 40 0 0 0 Velvetleaf 60 40 30 0 0 0 0 0 0 0 0 0 0 0 0 70 20 0 — 0 0 0 0 0 0 0 0 0 0 20 40 0 Rate 500 g/ha COMPOUND 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 58 59 60 61 Barnyardgrass 100 80 60 60 100 100 100 100 100 100 100 100 100 100 80 0 0 100 90 80 100 90 0 0 50 70 90 0 0 Surinam grass 60 60 20 0 100 0 60 20 90 0 100 20 100 80 0 0 0 0 30 20 0 0 0 0 30 0 80 0 0 Cocklebur 0 — 0 0 0 — 0 0 0 0 70 0 — 0 0 0 0 0 0 0 0 0 0 — — 0 0 0 0 Corn 0 0 0 0 0 0 0 0 60 0 20 0 20 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 Crabgrass 100 100 — 100 100 100 100 100 100 0 100 90 100 100 0 0 80 0 100 100 100 0 0 0 100 80 90 0 0 Foxtail, Giant 100 80 70 0 100 100 100 100 100 60 100 100 100 100 0 0 0 90 100 50 100 0 0 0 90 70 70 0 0 Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 90 100 100 100 0 0 100 0 100 0 — Morningglory 0 0 0 0 0 0 0 0 60 0 100 0 0 0 — 0 0 30 0 0 0 0 0 0 0 0 0 0 0 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 0 100 0 100 30 100 0 0 100 0 0 100 0 Rice 0 0 0 0 90 0 10 0 100 0 100 70 100 60 0 20 0 20 0 0 0 0 0 0 0 0 50 0 0 Velvetleaf 0 0 100 0 0 0 0 0 0 0 90 0 0 0 0 0 0 0 100 0 0 0 0 0 0 0 0 0 0 Rate 500 g/ha COMPOUND 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 Barnyardgrass 90 90 90 100 100 100 100 40 — 90 100 100 90 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 Surinam grass 0 30 60 20 20 50 0 20 0 40 70 90 20 100 100 40 0 90 90 100 100 90 100 90 60 100 100 100 Cocklebur 0 0 10 20 0 0 0 20 0 0 60 90 0 70 0 0 0 0 0 90 0 0 0 90 0 0 0 0 Corn 0 0 20 0 0 20 20 0 — 20 0 30 0 20 70 0 0 0 20 30 20 20 20 30 20 60 20 0 Crabgrass 90 100 100 70 40 80 20 0 100 100 100 100 70 100 100 90 30 100 100 100 100 100 100 100 100 100 100 100 Foxtail, Giant 80 90 90 70 40 40 20 0 100 100 100 100 60 100 100 0 10 60 100 100 100 100 100 100 100 100 100 100 Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 — 100 100 100 100 100 Morningglory 0 0 10 0 20 0 0 0 80 0 90 100 0 0 100 0 0 100 100 100 0 — 0 100 0 0 0 0 Pigweed 100 100 100 100 100 100 100 90 100 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Rice 30 0 0 20 20 40 30 0 30 40 0 40 0 70 90 0 0 90 90 90 100 100 100 100 0 100 100 10 Velvetleaf 0 0 0 20 20 0 0 0 0 30 90 100 0 70 0 0 0 90 70 80 0 0 0 100 0 0 0 0 Rate 500 g/ha COMPOUND 90 91 92 93 94 95 96 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 Barnyardgrass 100 100 100 100 0 100 100 90 100 100 100 0 0 0 0 100 30 0 100 0 100 100 0 0 0 0 100 100 Surinam grass 80 80 70 70 0 90 80 0 20 20 80 0 0 0 0 100 70 30 100 40 0 30 0 0 0 0 100 90 Cocklebur 0 0 0 0 0 60 30 0 0 0 0 0 0 0 0 100 20 0 0 70 0 0 0 0 0 0 100 0 Corn 20 30 0 0 0 50 20 0 30 20 70 0 0 0 0 30 0 0 0 0 30 30 0 30 0 0 30 30 Crabgrass 100 100 100 100 30 100 100 100 100 100 100 90 60 0 30 100 100 0 100 100 100 100 0 0 0 0 100 100 Foxtail, Giant 100 100 100 90 0 100 100 90 100 70 100 0 0 0 20 60 40 20 50 50 0 100 0 0 0 0 100 100 Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 0 100 100 100 100 100 100 100 100 100 100 0 100 0 0 100 100 Morningglory 0 0 0 0 0 60 80 0 0 0 0 0 0 0 0 100 100 0 0 0 0 30 0 30 0 0 100 100 Pigweed 100 100 100 80 0 100 100 40 100 100 100 0 0 100 100 100 100 60 100 100 100 100 0 100 0 0 100 100 Rice 0 0 0 0 20 100 100 30 20 20 — 0 0 0 0 100 0 0 0 0 0 100 0 0 0 0 70 0 Velvetleaf 0 0 0 0 70 50 50 0 0 0 0 0 0 0 0 100 0 0 70 80 0 0 0 0 0 0 100 90 Rate 500 g/ha COMPOUND 119 120 121 122 123 124 126 127 128 129 130 131 132 133 134 136 137 138 139 140 141 142 143 144 145 146 Barnyardgrass 100 100 100 100 0 100 100 100 100 100 100 100 100 100 100 0 40 100 0 100 100 100 100 100 100 100 Surinam grass 100 100 40 70 0 40 100 70 100 100 100 100 100 100 100 0 50 100 0 100 100 100 90 70 60 100 Cocklebur 30 40 30 0 0 0 70 0 60 0 50 30 30 0 0 0 80 100 0 60 100 60 30 0 0 0 Corn 40 50 50 0 0 0 50 0 60 30 70 50 0 90 90 0 0 20 0 20 20 20 20 20 0 0 Crabgrass 100 100 100 100 60 100 100 100 100 100 100 100 100 100 100 70 80 100 0 100 100 100 100 100 100 100 Foxtail, Giant 100 100 100 30 0 100 100 100 100 100 100 100 100 100 100 0 0 100 0 100 100 100 100 100 100 100 Lambsquarters 100 100 100 100 60 100 100 100 100 100 100 100 100 100 100 100 0 100 100 100 100 100 100 100 100 100 Morningglory 70 100 30 0 0 60 100 0 90 0 100 90 0 0 0 0 0 100 0 100 100 50 70 0 0 40 Pigweed 100 100 100 100 70 100 100 100 100 100 100 100 100 100 100 60 0 100 100 100 100 100 100 100 100 100 Rice 20 30 0 0 0 0 100 50 100 50 100 100 50 100 100 0 70 100 0 40 50 40 30 0 80 0 Velvetleaf 70 40 20 0 0 0 60 0 50 0 50 40 30 — 0 0 80 0 0 80 100 90 80 0 0 20 Flooded Paddy Rate 1000 g/ha COMPOUND 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 Barnyardgrass 100 100 70 100 100 100 100 100 100 60 0 0 0 0 0 80 0 60 100 100 100 0 100 100 0 90 100 0 100 100 100 0 Ducksalad 90 100 50 100 100 100 80 100 100 90 0 0 0 0 0 60 0 80 100 100 100 100 100 100 0 100 100 0 100 100 100 0 Rice 40 90 0 50 90 90 90 100 60 40 0 0 0 0 0 40 0 0 100 90 90 0 90 90 0 50 50 0 90 90 100 0 Flatsedge 90 100 90 100 100 100 100 100 100 100 30 0 0 0 0 90 0 90 100 100 100 0 100 100 0 100 100 30 100 100 100 0 Rate 1000 g/ha COMPOUND 34 35 41 42 46 47 50 51 52 53 54 55 56 57 58 59 60 61 93 94 138 139 Barnyardgrass 100 60 70 100 100 70 100 100 100 100 80 100 80 100 90 100 0 0 100 0 100 20 Ducksalad 100 0 70 100 70 20 100 100 100 30 30 80 20 100 70 70 50 30 100 0 90 0 Rice 30 0 40 100 90 70 60 30 50 20 0 0 0 90 20 20 0 0 50 0 90 0 Flatsedge 100 100 100 100 — 100 100 100 100 90 90 100 90 100 80 90 0 20 100 0 90 70

Test C

Seeds of plant species selected from bermudagrass (Cynodon dactylon), Surinam grass (Brachiaria decumbens), cocklebur (Xanthium strumarium), corn (Zea mays), crabgrass (Digitaria sanguinalis), woolly cupgrass (Eriochloa villosa), giant foxtail (Setaria faberii), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), kochia (Kochia scoparia), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), yellow nutsedge (Cyperus esculentus), pigweed (Amaranthus retroflexus), common ragweed (Ambrosia elatior), soybean (Glycine max) and velvetleaf (Abutilon theophrasti) were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.

At the same time, plants selected from these crop and weed species and also winter barley (Hordeum vulgare), blackgrass (Alopecurus myosuroides), canarygrass (Phalaris minor), chickweed (Stellaria media), downy brome (Bromus tectorum), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum), wheat (Triticum aestivum), wild oat (Avena fatua) and windgrass (Apera spica-venti) were treated with postemergence applications of some of the test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Plant species in the flooded paddy test consisted of rice (Oryza sativa), smallflower flatsedge (Cyperus difformis), duck salad (Heteranthera limosa) and barnyardgrass (Echinochloa crus-galli) grown to the 2-leaf stage for testing. Treated plants and controls were maintained in a greenhouse for 12 to 14 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table C, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

TABLE B Flooded Paddy Rate 16 g/ha Rate 31 g/ha Rate 62 g/ha COMPOUND COMPOUND COMPOUND 24 30 42 91 130 131 10 24 30 42 91 130 131 1 2 3 4 5 6 7 8 10 11 17 19 20 21 22 23 24 25 26 27 28 30 Barnyardgrass 80 60 50 0 50 50 0 100 80 70 0 70 60 20 0 20 0 20 0 0 0 0 0 0 0 70 40 40 80 100 100 0 20 0 100 Ducksalad 50 0 80 0 20 20 0 50 50 90 0 70 70 60 40 20 0 0 0 0 0 0 0 30 0 100 80 50 50 60 100 0 0 0 70 Rice 20 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 20 20 0 30 0 0 0 0 Flatsedge 100 90 100 0 90 90 30 100 90 100 0 100 90 90 70 90 0 90 80 80 30 50 90 20 0 90 80 100 100 100 100 90 90 80 90 Rate 62 g/ha COMPOUND 31 32 34 36 37 38 39 40 42 43 44 45 46 48 49 50 51 52 53 54 55 56 58 59 62 63 64 65 66 67 68 69 70 71 72 Barnyardgrass 80 20 0 100 70 100 80 100 100 30 90 70 0 20 100 0 20 30 20 0 0 0 0 0 0 20 20 40 70 60 90 30 60 0 0 Ducksalad 70 50 20 80 20 50 20 90 100 0 50 50 0 0 50 0 0 20 20 0 0 0 0 0 0 20 0 0 30 50 100 0 100 0 40 Rice 30 0 0 30 0 20 0 20 20 0 80 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 20 0 20 0 0 Flatsedge 100 100 70 100 100 100 90 100 100 90 90 90 80 90 100 80 40 90 80 0 40 80 0 0 0 90 100 0 100 100 100 100 90 80 60 Rate 62 g/ha COMPOUND 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 Barnyardgrass 30 0 70 40 0 0 30 0 20 30 60 80 40 0 0 30 20 30 0 50 0 70 80 0 0 0 0 0 0 0 0 0 30 20 0 0 Ducksalad 70 0 70 30 0 0 0 80 80 20 40 90 90 0 0 0 0 80 80 80 0 70 80 0 0 0 0 0 0 0 0 0 0 0 0 0 Rice 0 0 0 20 0 0 0 — 0 0 20 0 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 Flatsedge 90 0 90 90 70 0 90 90 90 90 90 90 90 0 0 90 80 100 0 90 0 90 90 30 60 0 70 20 0 0 0 40 80 30 0 40 Rate 62 g/ha COMPOUND 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 Barnyardgrass 0 0 0 0 0 0 0 40 50 30 20 0 0 0 0 65 35 0 40 30 90 100 40 90 100 0 0 0 Ducksalad 10 0 0 0 0 0 0 0 — 0 70 0 20 20 0 40 60 0 60 20 90 80 0 50 60 0 0 0 Rice 0 0 0 0 0 0 0 20 0 20 0 — 0 0 0 0 0 0 0 0 50 0 0 60 0 0 0 0 Flatsedge 50 50 20 0 0 0 0 100 0 0 90 100 0 30 0 100 100 0 90 70 90 90 90 100 90 0 0 0 Rate 62 g/ha Rate 125 g/ha COMPOUND COMPOUND 138 140 141 142 143 144 145 146 1 2 3 4 5 6 7 8 10 11 17 19 20 21 22 23 24 25 26 27 28 30 31 32 34 Barnyard- 0 50 70 80 55 100 30 75 80 0 80 0 70 20 20 0 0 20 0 0 100 50 80 80 100 100 50 60 0 100 80 100 40 grass Ducksalad 0 20 85 30 45 50 20 40 90 0 80 0 0 20 0 20 20 20 70 0 100 90 80 80 100 100 80 0 0 100 90 80 50 Rice 0 0 0 0 0 20 0 15 0 0 0 0 60 30 20 0 0 0 0 0 20 20 20 20 20 20 40 40 20 20 60 30 0 Flatsedge 90 90 90 95 90 85 40 60 100 90 100 0 90 90 90 90 80 90 70 0 100 90 100 100 100 100 90 90 80 100 100 100 90 Rate 125 g/ha COMPOUND 36 37 38 39 40 42 43 44 45 46 48 49 50 51 52 53 54 55 56 58 59 62 63 64 65 66 67 68 69 71 72 73 Barnyardgrass 100 100 100 80 100 100 80 100 100 20 40 100 40 20 60 30 0 50 30 0 0 20 40 80 80 100 70 100 30 0 50 70 Ducksalad 90 80 90 60 100 100 20 90 80 0 20 70 70 0 — 40 0 40 0 0 0 0 20 30 0 90 90 100 0 20 80 90 Rice 80 0 30 0 40 40 0 80 50 0 0 — 0 0 0 0 0 0 0 0 0 0 20 20 40 0 40 30 20 0 20 20 Flatsedge 100 100 100 100 100 100 100 100 100 90 90 100 90 90 90 90 0 90 80 0 0 90 100 100 100 100 100 100 100 100 90 100 Rate 125 g/ha COMPOUND 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 95 96 97 98 99 100 101 102 103 104 105 106 107 Barnyardgrass 0 — 90 0 0 40 60 80 60 70 — 90 30 70 100 70 60 50 100 50 70 80 40 0 0 0 40 0 0 0 0 50 30 Ducksalad 0 80 80 0 0 30 100 90 30 40 90 100 0 50 10 0 — 0 100 90 90 90 0 0 0 0 90 0 0 0 0 0 0 Rice 0 0 40 0 0 20 50 0 30 20 0 60 0 20 20 0 0 20 0 — 20 0 20 50 50 50 80 0 — 0 0 60 0 Flatsedge 0 90 90 70 0 90 90 90 90 100 90 100 0 100 90 90 100 70 100 100 100 90 90 80 90 70 90 30 80 0 90 90 50 Rate 125 g/ha COMPOUND 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 Barnyardgrass 0 0 0 0 0 0 0 0 0 80 60 70 50 20 0 0 0 100 100 0 100 50 100 100 70 90 100 0 Ducksalad 0 0 20 0 0 0 0 0 0 100 60 20 100 0 20 20 20 95 100 0 70 30 90 100 20 100 90 0 Rice 0 0 30 0 0 0 0 0 0 30 0 40 20 0 0 0 0 10 20 0 30 0 20 15 20 70 60 0 Flatsedge 0 50 50 60 50 0 0 0 0 100 100 100 100 100 80 30 20 100 100 0 90 80 100 100 90 100 100 20 Rate 125 g/ha Rate 250 g/ha COMPOUND COMPOUND 136 137 138 140 141 142 143 144 145 146 1 2 3 4 5 6 7 8 10 11 17 19 20 21 22 23 24 25 26 27 Barnyardgrass 0 0 40 100 100 100 100 100 65 100 30 0 100 0 70 60 100 40 40 30 0 0 100 50 100 100 100 100 80 60 Ducksalad 0 0 20 75 95 90 75 50 25 65 90 0 80 — 50 20 70 40 90 20 80 0 100 90 80 100 100 100 100 0 Rice 0 0 0 30 25 25 30 20 0 50 0 0 50 0 70 80 60 60 10 20 0 0 60 70 20 70 30 60 80 40 Flatsedge 0 0 90 90 90 95 95 85 80 95 100 100 100 60 100 90 90 100 100 90 80 0 100 90 100 100 100 100 95 100 Rate 250 g/ha COMPOUND 28 30 31 32 34 36 37 38 39 40 42 43 44 45 46 48 49 50 51 52 53 54 55 56 58 59 62 63 64 65 66 Barnyardgrass 40 100 90 100 80 100 100 100 100 100 100 100 100 100 50 100 100 70 90 70 70 20 100 30 0 0 20 70 80 100 100 Ducksalad 70 100 100 100 70 100 90 90 70 100 100 30 100 100 20 70 90 80 40 40 50 0 50 0 0 0 0 80 90 30 100 Rice 20 80 90 100 0 90 30 50 0 70 70 0 90 70 0 20 30 0 0 0 0 0 0 0 0 0 50 40 80 90 50 Flatsedge 100 100 100 100 90 100 100 100 100 100 100 100 100 100 90 100 100 90 100 100 90 0 90 90 0 0 90 100 100 100 100 Rate 250 g/ha COMPOUND 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 95 96 98 Barnyardgrass 100 100 100 100 0 50 100 0 80 90 0 0 90 90 90 100 70 100 100 100 70 100 100 90 100 100 60 100 100 30 Ducksalad 100 100 0 100 30 90 100 0 — 80 0 0 90 100 90 90 100 100 100 100 50 60 40 90 90 100 100 100 100 0 Rice 60 30 40 60 0 40 50 0 30 80 0 0 20 70 80 60 70 30 80 0 20 30 20 0 20 30 20 70 50 50 Flatsedge 100 100 100 90 100 90 100 0 100 90 80 0 90 90 90 90 100 100 100 70 100 100 90 100 100 100 100 100 100 90 Rate 250 g/ha COMPOUND 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 Barnyardgrass 20 0 50 0 20 0 20 90 70 0 70 70 20 20 0 0 0 0 90 100 70 80 20 0 0 0 100 100 Ducksalad 0 0 100 0 0 0 0 100 0 0 70 70 0 20 0 0 0 0 100 100 90 100 60 30 60 40 100 100 Rice 50 50 80 0 20 0 20 60 0 0 0 70 0 20 0 0 0 0 — 20 50 30 0 0 0 0 40 20 Flatsedge 100 70 90 30 100 0 90 100 60 30 80 100 90 100 0 0 0 0 100 100 100 100 100 80 50 30 100 100 Rate 250 g/ha Rate 500 g/ha COMPOUND COMPOUND 127 128 129 130 131 132 133 134 135 136 137 138 140 141 142 143 144 145 146 1 2 3 4 5 6 7 8 10 Barnyardgrass 20 100 80 100 100 100 100 100 0 0 0 100 100 100 100 100 100 85 100 100 0 100 0 100 100 100 70 80 Ducksalad 50 100 90 90 100 40 100 100 0 0 0 60 95 100 100 95 95 80 80 100 0 90 20 90 60 90 70 90 Rice 0 30 0 80 80 20 90 90 0 0 0 30 35 30 45 50 45 20 50 50 0 60 0 70 80 80 60 60 Flatsedge 80 100 90 90 100 90 100 100 90 0 0 100 95 95 95 95 95 95 95 100 100 100 90 100 100 100 100 100 Rate 500 g/ha COMPOUND 11 17 19 20 21 22 23 24 25 26 27 28 30 31 32 34 36 37 38 39 40 42 43 44 45 46 48 49 Barnyardgrass 80 70 0 100 100 100 100 100 100 100 70 70 100 100 100 80 100 100 100 100 100 100 100 100 100 60 100 100 Ducksalad 30 80 0 100 100 80 100 100 100 100 70 90 100 100 100 80 100 100 100 80 100 100 80 100 100 50 90 100 Rice 30 0 0 70 70 40 100 60 80 80 70 20 80 90 100 20 90 90 80 70 90 80 30 90 100 40 50 90 Flatsedge 100 80 30 100 100 100 100 100 100 95 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Rate 500 g/ha COMPOUND 50 51 52 53 54 55 56 58 59 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 Barnyardgrass 80 — 100 100 20 100 30 20 30 80 100 100 100 100 100 100 100 100 80 80 100 0 100 90 20 60 90 90 90 100 Ducksalad 90 70 100 60 0 50 0 0 0 0 100 90 90 100 100 100 20 100 30 90 100 0 90 100 30 0 90 100 100 100 Rice 50 0 60 0 0 0 0 0 20 50 40 90 90 100 90 100 80 90 60 50 60 0 40 80 30 0 50 90 80 80 Flatsedge 100 100 100 100 80 100 90 30 30 100 100 100 100 100 100 100 100 90 100 100 100 40 100 90 80 90 90 100 90 100 Rate 500 g/ha COMPOUND 83 84 85 86 87 88 89 90 91 92 93 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 Barnyardgrass 100 100 100 100 100 100 100 100 100 100 70 100 100 100 50 60 60 90 0 40 0 60 100 80 20 90 80 30 Ducksalad 100 100 100 — 100 60 90 90 70 100 100 100 100 0 0 0 40 100 0 90 0 0 100 70 0 90 70 0 Rice 80 90 100 20 80 70 40 20 40 30 80 90 60 20 50 80 80 90 0 20 0 30 90 20 0 20 80 0 Flatsedge 100 100 100 — 100 100 100 100 100 100 100 100 100 90 90 100 90 100 60 100 0 90 100 100 90 100 100 90 Rate 500 g/ha COMPOUND 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 140 Barnyardgrass 60 0 0 0 0 90 100 80 — 80 100 0 0 100 100 50 100 100 100 100 100 100 100 20 0 0 100 100 Ducksalad 30 0 0 0 0 100 100 100 100 90 60 70 80 100 100 80 100 90 100 100 80 100 100 0 0 0 100 95 Rice 70 0 0 0 0 30 30 50 80 0 0 0 0 60 60 0 70 35 — 90 90 90 90 0 0 0 70 50 Flatsedge 100 0 0 0 0 100 100 100 100 100 100 90 90 100 100 90 100 90 90 100 90 100 100 90 0 0 100 95 Rate 500 g/ha Rate 1000 g/ha COMPOUND COMPOUND 141 142 143 144 145 146 2 3 4 5 6 7 8 135 Barnyardgrass 100 100 100 100 100 100 80 100 90 100 100 100 100 30 Ducksalad 100 100 100 100 80 90 90 100 60 100 100 100 100 30 Rice 35 55 60 75 60 85 70 90 20 90 90 100 80 0 Flatsedge 95 95 100 95 95 95 100 100 90 100 100 100 100 100 Postemergence Rate 31 g/ha Rate 62 g/ha COMPOUND COMPOUND 21 36 37 81 106 109 20 21 25 30 36 37 38 40 68 69 80 81 85 91 106 107 109 117 119 120 121 122 131 140 141 142 143 Barley, Winter — — — — — — — — — 0 — — — — — — — 0 — — — — — — — — — Bermudagrass 50 0 0 0 0 0 60 50 60 70 0 0 0 0 0 — 0 0 0 20 0 0 0 0 0 0 0 0 20 30 40 30 20 Blackgrass — — — — — — — — — 0 — — — — — — — 0 — — — — — — — — — Surinam grass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 — 0 0 0 20 0 0 0 0 0 0 0 0 0 30 20 20 20 Downy Brome — — — — — — — — — 0 — — — — — — — 20 — — — — — — — — — Canarygrass — — — — — — — — — 0 — — — — — — — 0 — — — — — — — — — Chickweed 30 0 0 0 — — 50 50 60 50 0 0 0 0 30 — 20 20 20 70 — 50 — — — — — — — 90 90 — 100 Cocklebur 20 0 0 0 30 0 30 20 40 20 0 0 0 0 0 — 20 0 40 0 30 0 40 0 50 0 0 20 0 40 70 30 20 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 — 0 0 50 0 0 0 0 0 20 30 0 0 0 0 0 0 0 Crabgrass 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 — 0 0 30 20 0 0 0 0 30 0 0 0 — 40 60 40 40 Cupgrass, 0 0 0 0 0 0 0 0 40 0 0 0 0 0 0 — 0 0 30 20 10 0 0 0 0 0 0 0 10 40 30 40 40 Woolly Foxtail, Giant 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 — 0 0 20 20 0 0 0 0 0 0 0 0 20 — — 90 30 Foxtail, Green — — — — — — — — — 0 — — — — — — — 10 — — — — — — — — — Goosegrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 — 0 0 10 20 0 0 0 10 0 0 0 0 40 20 20 30 30 Johnsongrass 0 0 0 0 0 0 0 30 0 0 0 0 0 0 0 — 0 0 30 20 0 0 0 0 0 0 0 0 0 30 20 20 0 Kochia 30 20 0 40 70 80 70 40 50 50 60 0 60 20 50 — 0 50 40 70 70 70 80 80 60 50 70 90 60 40 10 40 40 Lambsquarters 70 50 20 0 80 70 70 80 80 80 60 20 30 20 60 — 10 60 70 100 80 50 70 75 90 50 90 100 100 80 70 80 90 Morningglory 0 0 0 50 90 60 0 50 50 0 0 0 0 0 50 — 50 60 60 0 90 60 100 100 80 0 50 20 — 60 70 20 90 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 — 0 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Pigweed 50 30 0 0 70 70 60 70 80 80 30 0 0 0 60 — 20 0 60 70 70 50 70 60 40 0 20 40 20 30 70 80 70 Ragweed, 0 0 0 0 — 0 0 20 0 — 0 0 0 0 0 — 0 0 0 0 0 — 0 — — — — — — 50 20 50 20 Common Ryegrass — — — — — — — — — 0 — — — — — — — 10 — — — — — — — — — Soybean 0 0 0 50 70 60 0 30 0 0 0 0 0 0 0 — 50 60 60 0 70 0 70 50 40 30 50 40 20 70 90 60 60 Velvetleaf 20 0 0 20 30 20 20 30 30 30 0 0 0 0 0 — 20 20 40 0 60 30 40 20 0 0 0 0 20 20 50 50 40 Wheat — — — — — — — — — 0 — — — — — — — 10 — — — — — — — — — Wild Oat — — — — — — — — — 0 — — — — — — — 30 — — — — — — — — — Windgrass — — — — — — — — — 0 — — — — — — — 20 — — — — — — — — — Rate 125 g/ha Rate 250 g/ha COMPOUND COMPOUND 20 21 25 30 36 37 38 40 68 69 80 81 85 91 106 107 109 117 119 120 121 122 131 140 141 142 143 20 25 30 36 37 38 40 Barley, Winter — — — — — — — — — 0 — — — — — — — 0 — — — — — — — — — — — — — — — — Bermudagrass 90 50 70 80 0 0 0 20 0 — 0 0 0 20 0 0 10 50 0 0 0 0 60 40 60 40 40 90 90 80 70 0 30 60 Blackgrass — — — — — — — — — 0 — — — — — — — 0 — — — — — — — — — — — — — — — — Surinam grass 0 0 0 0 0 0 0 0 0 — 0 0 20 20 0 0 0 0 0 0 0 0 — 30 40 30 20 0 0 0 0 0 0 0 Downy Brome — — — — — — — — — 0 — — — — — — — 40 — — — — — — — — — — — — — — — — Canarygrass — — — — — — — — — 0 — — — — — — — 0 — — — — — — — — — — — — — — — — Chickweed 50 50 70 60 0 0 0 0 40 — 20 20 70 80 — 100 — — — — — — — 100 100 100 100 70 80 70 50 0 0 0 Cocklebur — 30 60 30 0 0 0 0 0 — 30 20 70 0 80 30 60 80 70 30 0 20 0 70 — 60 40 60 60 30 0 0 0 0 Corn 0 0 0 20 0 0 0 0 0 — 0 0 50 0 0 0 40 0 20 30 0 0 10 0 0 0 0 0 20 30 20 0 0 20 Crabgrass 0 0 30 30 0 0 0 0 0 — 0 0 30 20 0 0 0 0 30 0 40 0 80 70 60 70 40 0 70 30 30 0 0 0 Cupgrass, 0 0 40 30 0 0 0 0 0 — 0 0 30 20 30 0 0 30 0 0 0 20 60 60 50 50 40 0 60 40 0 0 0 0 Woolly Foxtail, Giant 0 0 30 0 0 0 0 0 0 — 0 0 20 20 0 0 0 0 0 0 0 0 40 80 — — 80 70 80 30 20 0 0 0 Foxtail, Green — — — — — — — — — 30 — — — — — — — 20 — — — — — — — — — — — — — — — — Goosegrass 20 0 20 0 0 0 0 0 0 — 0 0 10 20 0 0 10 40 0 0 20 0 60 40 40 30 60 40 60 30 0 0 0 0 Johnsongrass 0 50 20 0 0 0 0 0 0 — 0 0 40 20 0 0 0 0 0 0 0 0 20 30 30 30 10 80 50 0 0 0 0 20 Kochia 70 40 70 70 70 20 60 50 70 — 0 50 60 70 90 80 90 85 70 80 70 90 80 90 80 90 80 70 70 70 80 70 70 60 Lambsquarters 70 80 90 90 70 20 30 40 80 — — — 90 100 80 100 100 80 90 90 90 100 100 90 100 90 90 80 100 90 70 50 70 50 Morningglory 20 60 — 0 0 0 0 0 60 — 60 80 80 0 90 100 100 100 90 80 70 40 70 90 90 100 100 20 80 40 20 0 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 — 20 0 — 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 30 0 0 0 Pigweed 70 70 90 80 60 0 0 0 70 — 40 0 70 70 80 50 70 75 70 0 70 60 70 80 70 80 70 80 100 90 60 0 0 50 Ragweed, 30 50 0 — 0 0 0 0 0 — 0 0 20 0 90 — 90 — — — — — — 80 80 70 70 30 30 — 30 0 40 30 Common Ryegrass — — — — — — — — — 0 — — — — — — — 20 — — — — — — — — — — — — — — — — Soybean 20 30 20 0 0 0 0 0 0 — 60 70 60 0 70 10 70 70 40 50 60 40 30 80 90 90 70 20 30 0 0 0 0 0 Velvetleaf 30 30 40 30 0 0 0 0 0 — 20 20 40 0 60 40 70 35 0 0 0 0 20 20 50 70 40 30 50 50 30 0 0 0 Wheat — — — — — — — — — 0 — — — — — — — 10 — — — — — — — — — — — — — — — — Wild Oat — — — — — — — — — 0 — — — — — — — 30 — — — — — — — — — — — — — — — — Windgrass — — — — — — — — — 0 — — — — — — — 30 — — — — — — — — — — — — — — — — Rate 250 g/ha Rate 500 g/ha COMPOUND COMPOUND 68 69 80 81 85 91 106 107 109 117 119 120 121 122 131 140 141 142 143 25 30 38 40 68 69 80 85 91 107 Barley, Winter — 0 — — — — — — — 0 — — — — — — — — — — — — — — 10 — — — — Bermudagrass 20 — 0 0 80 40 20 0 20 50 0 0 0 0 90 70 60 60 70 90 90 70 70 40 — 20 90 60 0 Blackgrass — 0 — — — — — — — 20 — — — — — — — — — — — — — — 20 — — — — Surinam grass 0 — 0 0 20 30 0 0 0 0 0 0 0 0 40 90 60 30 50 0 60 0 0 0 — 0 60 30 0 Downy Brome — 0 — — — — — — — — — — — — — — — — — — — — — — 0 — — — — Canarygrass — 0 — — — — — — — 20 — — — — — — — — — — — — — — 0 — — — — Chickweed 70 — 30 60 100 80 — 100 — — — — — — — — 100 — — 90 90 0 0 80 — 60 100 90 100 Cocklebur 0 — 30 50 90 0 90 30 — 85 70 80 20 40 30 80 70 90 90 60 50 20 0 50 — 40 90 20 80 Corn 0 — 0 0 50 0 20 0 — 0 20 30 0 0 20 0 0 0 0 30 40 0 30 0 — 0 60 0 0 Crabgrass 0 — 0 0 40 30 0 0 0 10 30 40 40 0 80 70 60 70 70 90 90 30 0 60 — 30 70 60 20 Cupgrass, 0 — 0 0 60 40 40 0 0 40 0 0 30 20 70 70 50 50 60 70 80 0 0 30 — 0 70 40 0 Woolly Foxtail, Giant 0 — 0 0 40 40 10 0 0 30 0 0 20 0 50 90 80 90 80 90 80 0 0 0 — 20 70 40 0 Foxtail, Green — 30 — — — — — — — 30 — — — — — — — — — — — — — — 60 — — — — Goosegrass 0 — 0 20 20 30 10 0 10 70 0 0 20 0 70 80 50 50 60 60 40 0 20 0 — 0 60 40 0 Johnsongrass 0 — 0 0 40 30 0 0 0 0 0 0 0 0 — 50 30 30 30 90 90 30 30 20 — 0 70 70 0 Kochia 70 — 30 70 80 90 100 80 90 85 90 90 70 100 80 90 80 90 90 70 90 70 70 70 — 50 90 90 85 Lambsquarters 80 — — 80 100 100 100 100 100 95 90 90 100 100 100 90 — 100 90 100 90 70 70 100 — 90 100 100 100 Morningglory 60 — 60 80 80 60 100 100 — 100 100 90 70 90 80 100 — 100 100 100 40 20 0 70 — 100 90 90 100 Nutsedge 0 — 20 0 — 0 0 0 0 0 0 0 0 0 0 20 0 0 0 0 0 0 20 0 — 20 90 20 0 Pigweed 70 — — 60 90 90 80 55 70 90 90 60 70 100 90 80 70 90 70 100 100 0 50 100 — 70 100 100 90 Ragweed, 0 — 50 0 20 0 — — — — — — — — — 90 80 90 90 40 — 40 40 30 — 80 90 40 50 Common Ryegrass — 0 — — — — — — — 30 — — — — — — — — — — — — — — 30 — — — — Soybean 0 — 70 90 70 0 80 20 70 85 80 60 60 50 30 90 100 90 100 30 0 0 0 20 — 90 70 0 25 Velvetleaf 0 — 20 20 40 0 70 50 — 35 10 0 20 0 20 70 50 80 80 50 60 0 20 30 — 20 40 0 80 Wheat — 0 — — — — — — — 10 — — — — — — — — — — — — — — 0 — — — — Wild Oat — 0 — — — — — — — 30 — — — — — — — — — — — — — — 20 — — — — Windgrass — 0 — — — — — — — 40 — — — — — — — — — — — — — — 20 — — — — Rate 500 g/ha COMPOUND 117 119 120 121 122 131 140 141 142 143 Barley, Winter 20 — — — Bermudagrass 95 0 70 0 0 90 90 100 80 80 Blackgrass 40 — — — Surinam grass 15 20 0 0 0 40 — 60 30 70 Downy Brome 40 — — — Canarygrass 20 — — — Chickweed — — — — — — — 100 — — Cocklebur 100 — 90 40 70 30 100 100 90 90 Corn 10 50 50 40 0 30 0 0 20 30 Crabgrass 10 60 90 60 0 90 70 70 70 70 Cupgrass, 45 20 0 60 20 80 70 70 70 70 Woolly Foxtail, Giant 60 80 70 60 40 80 90 — 90 90 Foxtail, Green 50 — — — Goosegrass 100 30 60 50 0 80 — 70 70 70 Johnsongrass 0 0 0 0 0 30 50 40 30 30 Kochia 90 90 90 90 100 90 90 90 90 90 Lambsquarters 100 100 100 100 100 100 100 100 100 100 Morningglory 100 — 100 100 100 100 100 100 100 100 Nutsedge 0 0 50 0 0 0 — 0 20 0 Pigweed 100 — 90 90 100 100 80 100 90 90 Ragweed, 90 — — — — — 90 90 100 90 Common Ryegrass 60 — — — Soybean 90 90 60 70 60 50 90 100 90 100 Velvetleaf 60 20 0 40 20 30 70 80 80 90 Wheat 20 — — — Wild Oat 30 — — — Windgrass 60 — — — Preemergence Rate 16 g/ha COM- Rate 31 g/ha Rate 62 g/ha POUND COMPOUND COMPOUND 43 21 25 27 28 34 36 37 42 43 49 70 73 81 90 101 106 109 124 138 8 20 21 22 25 27 28 30 31 Bermudagrass 20 60 90 30 20 0 100 60 — 40 0 80 60 100 0 40 100 100 0 60 0 70 100 30 100 90 50 100 90 Surinam grass 0 0 20 0 20 0 20 0 0 0 0 20 20 0 0 0 30 0 0 0 0 0 0 0 40 50 20 20 50 Cocklebur 0 0 0 0 0 0 0 0 — 20 0 0 20 0 0 0 70 0 0 0 0 0 0 0 0 0 — 0 0 Corn 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 20 0 20 0 30 40 Crabgrass 90 100 90 90 0 90 80 40 20 0 30 90 60 80 90 100 100 80 20 70 0 90 50 100 100 90 100 100 Cupgrass, 0 40 60 50 30 0 30 0 0 0 20 0 20 0 0 0 60 10 0 0 0 0 80 40 80 50 50 70 50 Woolly Foxtail, Giant 0 0 20 0 0 30 90 50 30 0 0 0 20 30 0 0 0 0 0 50 0 0 80 30 90 70 0 80 40 Goosegrass 0 80 100 40 40 20 90 60 — 0 0 30 60 90 20 10 100 90 0 20 0 80 80 90 100 90 80 100 100 Johnsongrass 0 30 30 0 0 0 50 20 — 0 0 0 0 0 10 0 30 0 0 0 0 0 70 20 70 20 50 30 30 Kochia 20 90 60 0 0 100 70 40 20 70 50 0 20 100 0 0 100 90 0 60 0 90 90 100 50 100 40 — — Lambsquarters 100 90 100 100 100 90 100 100 20 100 100 — — 100 10 0 100 100 45 100 100 90 100 100 100 100 100 100 100 Morningglory 0 0 0 0 0 0 0 0 — 0 0 0 30 0 0 0 80 30 0 30 20 0 20 0 20 20 0 30 30 Nightshade 0 80 20 0 0 0 0 0 0 0 0 20 50 70 0 0 100 50 0 0 0 30 90 0 100 0 0 80 80 Nutsedge 0 20 0 30 50 0 0 0 — 0 30 0 0 0 0 0 10 0 0 0 0 0 50 0 0 60 50 20 40 Pigweed 20 30 100 100 70 0 0 0 0 100 70 0 0 100 0 0 70 20 0 0 20 0 80 100 60 0 70 90 30 Ragweed, 0 — 0 — — 0 0 0 — 0 0 0 30 30 0 0 80 10 0 0 0 — — — 70 — — 0 30 Common Soybean 0 30 20 0 0 0 30 0 20 0 0 0 0 30 0 0 80 20 0 — 0 0 40 30 0 30 0 30 0 Sunflower 0 20 0 0 0 0 0 0 — 0 0 0 40 0 0 0 70 40 0 0 0 0 60 0 30 20 20 0 20 Velvetleaf 0 0 0 0 0 0 0 0 — 0 0 0 20 0 0 20 90 50 0 0 0 0 0 0 30 0 0 0 0 Rate 62 g/ha COMPOUND 32 33 34 36 37 38 39 40 42 43 44 45 49 50 51 52 56 62 63 64 67 70 71 72 73 75 76 79 80 81 Bermudagrass 50 90 80 100 70 60 90 80 — 50 90 50 100 100 90 100 40 40 100 100 100 100 30 0 70 100 100 100 100 100 Surinam grass 70 0 0 70 0 0 0 0 70 0 0 0 0 20 30 0 0 0 20 0 0 60 30 0 50 10 50 0 20 20 Cocklebur 0 0 0 30 — 0 0 20 — 100 — — 0 — 0 0 0 0 0 0 0 0 0 0 70 0 0 0 0 0 Corn 40 0 0 20 0 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 0 Crabgrass 100 80 60 100 90 90 90 100 90 40 100 90 100 100 70 90 30 0 100 100 100 100 40 90 90 90 100 100 100 100 Cupgrass, 60 20 20 60 0 0 0 60 20 30 30 0 30 20 50 30 0 30 20 30 90 70 0 0 60 60 50 90 90 30 Woolly Foxtail, Giant 70 50 30 0 60 80 0 90 50 0 0 30 0 60 70 60 0 0 20 0 100 100 0 30 80 90 100 0 0 90 Goosegrass 100 80 80 100 90 80 80 90 — 50 90 90 100 80 80 90 60 80 100 100 100 90 30 20 80 90 100 80 100 100 Johnsongrass 30 0 0 90 30 40 0 50 — 0 0 0 0 0 20 0 0 20 0 30 30 0 0 0 20 0 20 0 20 0 Kochia — 100 100 100 50 30 0 60 50 90 70 20 90 0 40 0 50 0 70 90 90 80 80 30 80 100 100 100 100 100 Lambsquarters 100 100 90 100 100 90 100 100 100 100 100 60 100 20 60 0 100 — — — 100 100 — 0 — 100 100 100 100 100 Morningglory 30 0 0 0 0 — 0 0 — 0 0 0 0 20 — — 0 0 0 40 0 20 0 0 30 0 10 0 0 0 Nightshade 50 0 0 30 0 0 0 0 0 0 0 0 0 0 0 30 0 0 30 30 0 30 0 30 60 0 0 20 90 100 Nutsedge — 0 0 0 20 0 0 0 — 0 0 — 40 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Pigweed 70 0 100 0 0 0 0 0 60 100 0 0 100 30 20 0 0 0 0 0 80 0 0 50 0 100 100 0 0 40 Ragweed, 0 0 0 0 0 0 0 0 — 0 0 0 0 20 0 0 0 0 0 0 0 20 0 30 70 0 0 60 90 30 Common Soybean 50 0 0 30 0 0 0 — 50 0 0 0 0 — — 20 0 0 0 0 0 0 0 0 0 0 0 0 — 100 Sunflower 0 0 0 0 0 0 0 0 — 0 0 20 20 20 0 — 0 0 0 20 0 0 0 0 50 0 20 0 30 0 Velvetleaf 0 0 0 0 0 0 0 0 — 0 0 0 0 0 0 0 0 0 0 0 0 20 0 0 20 0 10 0 0 10 Rate 62 g/ha COMPOUND 82 83 84 85 86 87 88 89 90 91 92 93 95 96 99 100 101 106 107 109 111 117 118 119 120 121 122 124 127 Bermudagrass 100 100 100 100 10 100 100 10 0 10 20 0 100 100 90 90 40 100 85 100 60 100 100 100 100 100 100 60 90 Surinam grass 10 40 0 30 20 40 40 0 0 0 0 0 40 50 0 0 0 90 0 0 0 10 0 100 90 20 0 0 0 Cocklebur 0 0 0 60 0 0 0 0 0 0 0 0 0 0 0 0 0 90 0 0 0 0 0 — 0 0 0 0 0 Corn 0 0 0 30 0 40 0 10 0 0 0 0 10 0 0 20 0 0 0 0 0 0 0 30 0 0 0 0 0 Crabgrass 100 100 90 100 0 100 100 20 80 100 60 80 100 100 100 100 100 100 100 100 80 100 100 100 100 100 90 90 50 Cupgrass, 70 80 60 100 30 90 60 0 0 10 0 0 50 60 0 0 0 100 50 90 0 80 40 100 100 80 0 30 0 Woolly Foxtail, Giant 30 0 10 60 0 30 0 0 40 10 20 0 0 100 10 90 40 0 100 0 0 100 0 50 50 20 0 0 0 Goosegrass 90 100 20 100 20 100 100 95 100 90 60 20 100 100 80 80 100 100 10 100 40 100 100 100 100 100 90 0 10 Johnsongrass 40 20 0 — 20 90 10 50 10 20 50 0 30 20 0 0 10 70 — 10 0 45 0 90 20 60 0 15 0 Kochia 0 60 80 100 70 100 70 20 0 20 0 0 100 100 80 0 0 100 70 100 0 90 80 100 100 100 100 40 0 Lambsquarters 100 100 100 100 100 100 100 80 100 90 80 0 100 100 100 90 0 100 90 100 70 100 100 100 100 100 100 50 20 Morningglory 20 0 0 50 0 0 10 0 0 0 0 0 0 0 0 0 0 90 0 90 0 0 0 60 60 0 0 0 0 Nightshade 0 0 30 80 0 0 30 0 0 0 0 0 0 0 0 0 0 100 80 90 0 100 100 100 100 10 0 0 0 Nutsedge 0 0 0 50 0 20 0 0 0 0 0 0 0 0 0 0 0 10 0 0 0 0 0 0 40 0 0 0 0 Pigweed 0 90 90 100 70 0 0 0 60 0 0 0 100 0 0 0 0 100 90 20 80 100 75 50 100 20 0 0 0 Ragweed, 0 0 0 90 0 0 0 0 0 0 0 0 0 0 0 0 0 100 0 90 0 100 60 100 100 0 0 0 0 Common Soybean 0 0 0 20 0 0 0 0 0 0 0 0 0 0 0 0 0 100 30 80 0 100 40 60 60 0 0 0 0 Sunflower 0 0 0 40 0 20 10 0 0 0 0 0 0 0 0 0 0 70 0 70 0 35 0 40 60 10 0 0 0 Velvetleaf 30 0 0 70 0 10 0 0 0 0 0 0 0 0 0 0 20 100 40 100 0 80 20 60 80 0 0 0 0 Rate 62 g/ha Rate 125 g/ha COMPOUND COMPOUND 128 129 130 131 132 133 134 138 140 141 142 143 144 145 8 20 21 22 25 27 28 30 31 32 33 34 36 37 Bermudagrass 100 100 100 100 100 100 100 70 100 100 100 100 100 60 70 100 100 100 100 100 100 100 100 90 100 90 100 80 Surinam grass 90 80 100 100 90 100 100 0 0 10 0 0 0 0 0 0 30 40 80 50 60 40 50 80 0 0 70 0 Cocklebur 0 0 0 0 — 0 0 0 30 0 0 — 50 0 0 0 0 0 0 0 0 0 0 — 0 0 — 0 Corn 0 0 40 100 0 100 — 0 20 0 0 30 30 0 0 30 20 20 20 20 30 40 40 50 0 0 40 40 Crabgrass 100 100 100 100 100 100 100 70 100 100 100 100 100 100 70 100 100 100 100 100 100 100 100 100 100 70 100 90 Cupgrass, 100 90 100 100 90 100 100 40 100 100 90 90 100 20 40 50 80 70 100 80 70 70 60 70 90 20 100 0 Woolly Foxtail, Giant 20 20 90 90 70 90 90 80 100 100 100 100 100 100 20 0 90 0 70 100 100 60 50 50 100 0 100 70 Goosegrass 100 100 100 100 100 100 100 80 100 100 100 100 100 90 20 100 100 90 100 100 100 100 100 100 100 80 100 90 Johnsongrass 60 20 0 30 50 80 100 0 0 0 0 0 0 0 0 20 90 30 90 50 70 40 60 40 0 0 90 30 Kochia 100 0 100 100 — 100 100 90 100 100 100 100 90 100 0 100 90 100 100 100 100 — — — 100 100 100 100 Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Morningglory 30 0 70 0 0 0 0 30 70 30 90 30 — 0 30 30 20 0 30 20 0 30 30 40 0 0 0 0 Nightshade 20 0 100 90 0 0 0 0 100 100 90 100 100 0 0 70 100 0 100 0 70 90 90 50 — 0 50 0 Nutsedge 20 0 30 0 0 70 60 0 20 0 0 0 0 0 0 0 60 0 0 60 50 — 50 50 0 0 30 20 Pigweed 70 20 100 90 0 50 100 30 100 100 100 100 100 100 80 30 100 50 100 100 100 50 100 20 0 100 0 0 Ragweed, 100 0 100 0 0 0 0 0 100 100 0 90 0 0 0 — — — 70 — — 90 90 0 0 0 30 20 Common Soybean — 10 30 0 20 0 0 30 50 70 30 70 50 20 0 0 80 40 30 40 40 70 0 50 0 0 50 — Sunflower 20 0 60 20 0 0 0 0 30 30 10 60 40 0 0 40 70 0 40 20 40 80 30 0 0 0 0 0 Velvetleaf 10 0 60 20 0 0 20 0 60 70 10 70 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 20 Rate 125 g/ha COMPOUND 38 39 40 42 43 44 45 49 50 51 52 56 62 63 64 67 70 71 72 73 75 76 79 80 81 82 83 84 Bermudagrass 90 90 100 — 60 100 90 100 100 100 100 50 70 100 100 100 100 90 90 100 100 100 100 100 100 90 100 100 Surinam grass 0 0 80 90 0 80 0 0 30 30 20 0 30 20 50 0 70 30 30 70 40 60 20 70 50 80 50 0 Cocklebur 0 — 20 — 100 0 0 0 0 0 0 0 0 0 0 0 0 0 30 — 0 0 0 50 0 10 0 0 Corn 0 0 20 40 0 0 0 0 0 — 0 0 0 0 0 0 0 0 0 0 0 20 0 30 0 20 0 0 Crabgrass 100 100 100 100 90 100 100 100 100 100 100 30 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Cupgrass, 0 20 90 100 30 90 30 60 20 50 50 0 50 60 50 70 100 80 10 80 80 100 90 100 30 90 90 90 Woolly Foxtail, Giant 0 0 0 100 0 100 40 100 0 0 70 0 0 90 50 100 100 90 70 100 100 100 0 100 100 0 100 80 Goosegrass 90 90 100 — 90 100 100 100 90 90 90 80 90 100 100 100 100 90 70 100 100 100 90 100 100 100 100 80 Johnsongrass 50 0 100 — 50 60 0 0 40 20 40 0 40 60 70 60 10 0 0 30 0 30 0 60 20 50 30 0 Kochia 70 50 90 100 100 100 60 90 0 50 20 70 60 100 100 100 90 90 100 100 100 100 100 100 100 90 90 100 Lambsquarters 100 100 100 100 100 100 100 100 50 100 80 100 — — — 100 100 — 100 — 100 100 100 100 100 100 100 100 Morningglory 0 0 0 — 0 0 0 0 30 0 0 0 0 20 40 0 0 0 30 30 0 30 0 20 20 10 0 20 Nightshade 0 0 0 100 0 0 0 30 0 0 30 0 0 60 70 70 50 20 10 80 0 30 50 100 100 10 50 50 Nutsedge 0 0 0 — 30 30 0 50 0 20 0 0 0 0 0 40 0 30 0 30 0 0 0 20 0 0 0 0 Pigweed 0 0 100 100 0 0 0 100 20 0 0 90 0 100 100 90 20 0 100 0 100 100 10 0 100 70 50 0 Ragweed, 20 0 0 — 30 0 0 30 30 0 0 0 0 50 50 20 60 0 0 80 0 0 100 100 100 0 0 0 Common Soybean 0 0 20 50 40 0 0 40 0 0 20 0 0 0 20 0 10 0 0 40 0 0 0 30 — 10 0 0 Sunflower 0 0 0 — 0 0 20 20 30 0 0 0 0 0 20 0 20 0 20 50 0 20 0 30 0 20 30 10 Velvetleaf 0 0 0 — 0 0 0 0 0 0 0 0 0 0 0 50 0 0 0 50 0 20 0 40 30 10 30 0 Rate 125 g/ha COMPOUND 85 86 87 88 89 90 91 92 93 95 96 99 100 101 106 107 109 111 117 118 119 120 121 122 124 127 128 129 Bermudagrass 100 30 100 100 90 100 100 20 90 100 100 90 90 100 100 100 100 90 100 100 100 100 100 100 80 100 100 100 Surinam grass 30 20 100 30 10 10 30 0 10 40 90 0 0 20 90 0 80 0 10 10 100 100 80 0 0 0 100 80 Cocklebur 60 0 0 0 0 0 0 0 0 0 20 0 — 0 90 0 30 0 10 0 — 0 20 0 0 0 10 0 Corn 30 0 70 10 25 0 0 10 0 10 20 0 — 0 0 0 0 0 30 0 30 0 20 0 0 0 20 20 Crabgrass 100 90 100 100 100 100 100 80 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 70 100 100 Cupgrass, 100 30 100 90 0 10 70 10 20 100 95 0 20 20 100 60 90 20 100 90 100 100 100 20 50 50 100 100 Woolly Foxtail, Giant 100 0 100 100 0 0 30 0 20 0 0 20 10 40 40 100 20 0 0 100 100 50 100 0 20 0 90 60 Goosegrass 100 90 100 100 100 100 100 75 100 100 100 80 90 100 100 70 100 85 100 100 100 100 100 100 40 30 100 100 Johnsongrass 50 20 90 10 70 70 80 65 — 30 30 0 90 40 100 20 50 0 50 40 100 80 90 0 20 0 90 70 Kochia 100 90 100 90 70 40 90 40 0 100 100 90 0 0 100 70 100 0 100 100 100 100 100 100 60 0 100 100 Lambsquarters 100 100 100 100 100 100 100 100 70 100 100 100 100 100 100 100 100 85 100 100 100 100 100 100 100 80 100 100 Morningglory 90 0 0 10 0 0 0 0 0 0 0 20 0 0 100 0 100 0 10 20 90 60 10 0 0 0 60 0 Nightshade 90 0 10 20 0 0 0 0 0 0 10 0 0 90 100 90 100 0 100 100 100 100 90 0 20 0 40 0 Nutsedge 70 0 20 0 0 0 0 0 0 0 0 0 0 0 80 0 0 0 0 0 20 80 0 0 0 0 70 0 Pigweed 100 100 0 10 0 0 0 0 20 0 0 90 0 0 100 0 70 20 100 100 50 100 50 20 0 0 70 100 Ragweed, 100 0 0 0 0 0 0 0 0 0 0 0 0 100 100 30 100 0 100 — 100 100 90 0 0 0 100 0 Common Soybean 40 0 20 10 0 0 0 0 0 0 0 0 0 0 100 30 90 0 100 60 80 70 60 0 0 0 — 20 Sunflower 70 20 20 40 0 0 0 0 0 0 0 0 0 0 80 0 90 0 40 50 40 90 30 0 0 0 100 0 Velvetleaf 70 0 10 10 0 0 0 0 0 0 0 0 0 50 100 50 100 0 90 100 100 100 20 10 0 0 20 0 Rate 125 g/ha Rate 250 g/ha COMPOUND COMPOUND 130 131 132 133 134 138 140 141 142 143 144 145 8 20 22 25 27 28 30 31 32 33 34 36 37 38 39 40 Bermudagrass 100 100 100 100 100 70 100 100 100 100 100 100 70 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Surinam grass 100 100 100 100 100 0 0 20 0 0 0 50 50 0 60 80 80 60 40 60 80 90 0 100 90 0 0 90 Cocklebur — 0 0 0 0 0 30 60 30 50 60 20 0 0 0 100 0 0 0 30 0 0 0 30 0 20 — — Corn 80 100 10 — 20 0 20 30 0 30 50 20 0 30 20 20 30 30 50 40 50 0 0 80 40 0 0 50 Crabgrass 100 100 100 100 100 100 100 100 100 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Cupgrass, 100 100 100 100 100 60 100 100 100 100 100 100 50 90 100 100 100 100 90 90 90 100 80 100 100 0 90 90 Woolly Foxtail, Giant 100 100 70 100 100 100 100 100 100 100 100 100 90 100 0 100 0 0 90 60 100 0 50 100 100 100 0 100 Goosegrass 100 100 100 100 100 90 100 100 100 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Johnsongrass 90 70 80 100 100 30 20 0 0 60 90 10 0 50 40 90 50 70 90 90 90 0 0 100 90 90 70 100 Kochia 100 100 100 100 100 100 100 100 100 100 100 100 20 100 100 100 100 100 — — — 100 100 100 100 90 70 100 Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Morningglory — 60 — 0 0 80 90 100 100 100 0 100 30 40 0 100 30 0 80 40 50 0 0 50 30 0 0 0 Nightshade 100 100 0 0 10 50 100 100 100 100 100 10 0 90 40 90 0 90 100 100 90 0 0 90 0 60 0 40 Nutsedge 80 90 0 — 70 0 40 0 0 0 0 0 0 50 0 40 80 50 40 70 50 0 0 30 30 0 0 50 Pigweed 100 90 30 100 100 50 100 100 100 100 100 100 100 100 50 90 100 50 90 80 70 60 40 100 100 0 0 0 Ragweed, 100 0 0 0 0 0 — 100 100 100 0 0 — — — 70 — — 90 90 90 0 0 50 60 40 0 30 Common Soybean 30 0 20 0 0 60 80 100 70 80 50 30 20 60 40 50 50 40 70 0 60 0 0 50 50 0 0 40 Sunflower 60 20 20 0 0 0 50 40 20 80 40 0 0 60 0 70 20 40 80 40 70 30 0 30 60 60 0 30 Velvetleaf 60 30 — 20 20 0 70 70 90 70 0 0 20 20 0 70 0 0 0 30 0 0 0 40 20 20 0 30 Rate 250 g/ha COMPOUND 44 45 49 50 51 52 56 62 63 64 67 70 71 72 73 75 76 79 80 81 82 83 84 85 86 87 88 89 Bermudagrass 100 100 100 100 100 100 90 100 100 100 100 100 100 90 100 100 100 100 100 100 100 100 100 100 90 100 100 90 Surinam grass 80 40 70 50 70 30 0 60 70 90 100 70 50 80 70 60 80 60 100 100 70 90 30 100 20 100 70 30 Cocklebur 30 20 0 0 0 — 0 0 30 20 20 0 30 10 80 0 20 0 0 20 20 30 0 60 0 0 20 10 Corn 0 0 0 0 0 20 0 0 20 30 0 0 0 0 0 0 20 0 0 0 10 0 0 60 0 70 70 30 Crabgrass 100 100 100 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Cupgrass, 100 70 70 90 80 60 0 90 60 90 100 100 100 80 100 100 100 100 100 100 90 100 90 100 90 100 100 40 Woolly Foxtail, Giant 100 40 100 20 100 90 20 100 100 100 70 100 0 70 100 70 20 0 40 100 100 60 100 100 80 100 100 0 Goosegrass 100 100 100 100 100 100 90 100 100 100 100 100 100 80 100 100 100 100 100 100 100 100 90 100 100 100 100 100 Johnsongrass 90 50 50 70 60 90 0 60 100 90 100 50 0 0 50 30 40 0 60 20 50 30 0 80 40 100 40 70 Kochia 100 90 100 0 50 30 100 90 100 100 90 100 100 90 100 100 100 100 100 100 100 90 100 100 100 100 100 90 Lambsquarters 100 100 100 70 100 100 100 — — — 100 100 — 100 — 100 100 100 100 100 100 100 100 100 100 100 100 100 Morningglory 20 0 0 30 — 0 0 0 30 40 0 0 0 10 100 0 30 30 100 20 20 0 20 90 0 0 30 0 Nightshade 0 0 50 0 0 30 0 0 60 90 80 70 30 30 100 0 40 50 100 100 30 60 100 100 0 60 80 0 Nutsedge 60 60 0 0 30 20 0 20 20 50 0 0 70 20 50 50 20 0 0 0 10 0 0 70 0 20 0 0 Pigweed 20 0 100 20 100 30 0 0 100 100 80 0 100 0 40 100 0 20 0 100 100 100 100 100 0 100 40 50 Ragweed, 50 30 30 40 0 40 0 0 50 80 70 80 0 70 100 0 0 100 100 100 50 0 0 100 0 0 0 0 Common Soybean 30 0 50 0 20 20 0 0 0 20 0 20 0 0 70 0 0 0 50 100 30 0 0 40 0 20 10 0 Sunflower 20 20 30 30 30 0 0 0 40 50 0 60 0 20 70 0 30 50 60 0 70 0 30 70 20 20 20 0 Velvetleaf 20 20 30 0 30 0 0 0 30 20 0 0 0 10 60 0 20 20 70 80 10 0 0 80 0 10 10 0 Rate 250 g/ha COMPOUND 90 91 92 93 95 96 99 100 101 106 107 109 111 117 118 119 120 121 122 124 127 128 129 130 131 132 133 134 Bermudagrass 100 100 85 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Surinam grass 40 30 20 30 50 100 0 0 40 100 0 90 0 75 30 100 100 100 20 10 20 100 90 100 100 100 100 100 Cocklebur 0 0 20 0 0 30 0 0 50 100 0 30 0 50 0 20 30 50 0 0 0 40 0 0 30 0 0 0 Corn 10 10 30 0 40 40 0 20 60 40 0 0 0 45 10 60 20 70 0 0 30 40 30 90 100 70 100 100 Crabgrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Cupgrass, 60 90 50 70 100 100 10 20 100 100 80 100 60 100 100 100 100 100 100 60 90 100 100 100 100 100 100 100 Woolly Foxtail, Giant 40 30 100 20 0 0 20 40 100 100 100 90 30 100 100 90 60 60 0 85 100 90 80 100 100 100 100 100 Goosegrass 100 100 100 100 100 100 90 100 100 100 80 100 100 100 100 100 100 100 100 60 100 100 100 100 100 100 100 100 Johnsongrass 100 90 70 10 60 50 0 90 90 100 50 50 0 50 70 100 100 100 0 30 0 100 100 100 80 100 100 100 Kochia 80 90 70 30 100 100 90 90 0 100 85 100 0 100 100 100 100 100 100 90 0 100 100 100 100 100 100 100 Lambsquarters 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Morningglory 0 0 0 0 0 20 20 0 100 100 0 100 0 100 90 100 100 50 100 0 0 70 — 90 90 0 20 0 Nightshade 0 0 20 0 0 60 0 0 100 100 90 100 0 100 100 100 100 100 30 100 0 90 10 100 100 20 20 30 Nutsedge 0 0 0 0 — 10 0 0 0 100 0 0 0 0 0 30 100 0 0 0 0 100 50 100 90 0 90 90 Pigweed 100 0 100 20 0 0 20 20 10 90 0 80 20 100 100 90 50 60 20 50 0 80 60 100 100 70 100 100 Ragweed, 0 0 0 0 0 40 0 0 100 100 60 100 0 100 80 100 100 90 20 0 10 100 100 100 0 0 0 0 Common Soybean 0 0 30 0 0 50 0 0 50 100 40 90 0 100 65 100 80 90 0 0 0 60 20 40 40 20 0 0 Sunflower 10 0 40 0 0 50 0 0 30 90 40 90 0 60 60 40 100 50 0 0 0 100 10 70 20 20 0 0 Velvetleaf 0 0 0 0 0 30 0 0 90 100 50 100 0 100 100 100 100 100 20 0 10 30 0 60 70 0 20 20 Rate 250 g/ha Rate 500 g/ha COMPOUND COMPOUND 138 140 141 142 143 144 145 8 20 22 25 30 31 32 33 38 39 40 44 45 49 50 51 52 56 62 63 64 Bermudagrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Surinam grass 100 90 20 50 70 0 90 60 40 90 80 60 70 90 100 90 80 100 90 70 80 50 70 50 0 80 100 100 Cocklebur 0 90 70 30 50 60 50 0 50 0 70 80 30 0 0 60 0 60 100 90 20 0 0 30 100 0 30 30 Corn 30 30 30 0 30 50 40 0 30 30 50 50 60 60 40 0 70 90 70 0 0 0 0 40 0 20 40 40 Crabgrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Cupgrass, 100 100 100 100 100 100 100 80 100 100 100 100 100 90 100 90 100 100 100 100 100 90 100 100 70 90 100 100 Woolly Foxtail, Giant 100 100 100 100 100 100 100 100 0 100 90 100 100 100 30 100 100 100 90 90 100 100 100 30 90 100 100 30 Goosegrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Johnsongrass 40 100 0 100 90 100 20 0 100 40 100 100 100 90 100 90 90 100 100 100 90 90 90 100 0 100 100 100 Kochia 100 100 100 100 100 100 100 70 100 100 100 — — — 100 100 90 100 100 100 100 20 80 60 100 90 100 100 Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 70 100 100 100 — — — Morningglory 80 100 100 100 100 30 100 30 40 0 90 80 50 80 0 0 0 0 40 0 30 30 20 30 0 0 40 60 Nightshade 90 100 100 100 100 100 20 0 90 80 100 100 100 100 100 90 0 70 30 40 90 60 60 50 20 0 100 90 Nutsedge 40 60 0 0 0 0 0 0 50 20 0 40 90 60 0 70 40 60 100 100 0 70 30 40 0 70 100 50 Pigweed 50 100 100 100 100 100 100 100 60 100 90 100 90 80 100 30 100 100 100 30 100 90 30 100 100 100 100 100 Ragweed, 30 100 100 100 100 30 0 80 — — 100 100 100 100 30 100 20 70 50 60 90 40 0 50 20 0 90 90 Common Soybean 100 100 100 100 80 70 30 20 60 40 60 70 0 60 0 0 0 40 30 0 80 40 30 60 0 0 40 30 Sunflower 50 60 40 80 80 40 50 30 70 0 70 100 40 70 60 60 0 40 30 70 80 60 30 50 0 0 60 60 Velvetleaf 0 90 70 100 90 20 0 20 20 0 20 30 30 40 0 20 0 50 60 30 40 0 30 0 20 20 50 50 Rate 500 g/ha COMPOUND 67 70 71 72 75 76 79 80 82 83 84 85 86 87 88 89 91 92 93 95 96 99 100 107 111 117 118 119 Bermudagrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 90 100 100 100 100 100 100 100 100 100 100 Surinam grass 100 80 90 50 60 100 100 100 100 100 80 100 30 100 100 65 80 35 70 100 100 90 30 0 10 100 50 100 Cocklebur 50 20 30 70 0 20 30 100 40 0 0 60 0 0 20 10 10 20 20 0 30 0 0 0 0 85 0 50 Corn 100 20 30 0 0 80 0 60 30 10 0 80 30 80 100 30 10 40 30 40 50 20 20 10 0 50 35 90 Crabgrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Cupgrass, 100 100 100 70 100 100 100 100 100 100 100 100 100 100 100 70 100 50 80 100 100 100 100 80 60 100 100 100 Woolly Foxtail, Giant 100 100 100 90 100 90 0 50 100 0 100 100 100 100 100 100 100 100 60 100 100 70 100 100 80 100 100 100 Goosegrass 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Johnsongrass 100 70 40 40 30 100 0 70 60 30 0 100 50 100 100 100 100 100 10 90 70 90 100 50 25 90 100 100 Kochia 100 100 100 100 — 100 100 100 100 100 100 100 100 100 100 100 100 100 80 100 100 100 100 100 0 100 100 100 Lambsquarters 100 100 — 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Morningglory 20 40 0 100 0 30 70 100 80 0 20 100 — 0 30 0 0 0 20 0 20 20 0 100 0 100 100 100 Nightshade 60 70 30 60 50 60 90 100 100 100 100 100 10 90 80 30 10 80 10 45 80 10 0 90 0 100 100 100 Nutsedge 20 0 70 20 50 20 0 0 40 0 0 90 0 20 10 0 0 0 0 70 70 90 0 0 0 0 0 30 Pigweed 80 100 100 100 100 100 100 40 0 100 90 100 100 100 100 100 100 50 80 60 50 70 100 100 50 30 100 100 Ragweed, 70 100 30 90 60 0 100 100 100 100 0 100 0 0 20 0 0 40 0 10 70 0 0 70 0 100 100 100 Common Soybean 0 20 0 20 50 0 50 100 60 10 0 100 0 30 30 30 0 100 20 30 70 0 0 60 0 100 90 100 Sunflower 30 60 20 60 50 30 60 60 80 70 30 70 20 30 20 60 10 55 20 10 50 0 0 70 0 65 70 100 Velvetleaf 30 10 0 40 0 50 50 100 30 40 0 100 70 20 20 10 0 0 20 0 40 0 0 100 0 100 100 100 Rate 500 g/ha COMPOUND 120 121 122 127 128 129 130 131 132 133 134 140 141 142 143 144 145 Bermudagrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Surinam grass 100 100 60 100 100 100 100 100 100 100 100 100 100 100 70 90 100 Cocklebur 30 100 0 20 70 0 0 30 0 0 0 — 100 60 55 60 60 Corn 60 90 0 30 60 30 100 100 90 100 100 30 30 10 30 60 40 Crabgrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Cupgrass, 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Woolly Foxtail, Giant 100 100 0 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Goosegrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Johnsongrass 100 100 20 0 100 100 100 100 100 100 100 100 100 100 90 100 90 Kochia 100 100 100 0 100 100 100 100 100 100 100 100 100 100 100 100 100 Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Morningglory 100 70 — 20 80 0 — 90 0 30 0 100 100 100 100 30 — Nightshade 100 100 90 100 100 60 100 100 20 90 90 100 100 100 100 100 90 Nutsedge 100 0 0 0 100 90 100 100 90 90 100 70 50 20 0 0 0 Pigweed 70 100 100 0 100 100 100 100 100 100 100 100 100 100 100 100 100 Ragweed, 100 100 100 10 100 100 100 100 0 0 40 100 100 100 100 50 20 Common Soybean 100 100 0 0 — 20 60 40 30 0 20 100 100 100 100 70 60 Sunflower 100 70 30 0 100 10 70 20 — 0 20 90 100 80 90 70 50 Velvetleaf 100 100 20 30 50 10 60 70 0 30 20 90 100 100 100 20 20

Test D

Four plastic pots (ca. 16-cm diameter) per rate were partially filled with sterilized Tama silt loam soil comprised of a 35:50:15 ratio of sand, silt and clay and 2.6% organic matter. Separate plantings for each of the four pots were as follows. Seeds from the U.S. of Heteranthera limosa (Hl), Monochoria vaginalis (Mv), Ammania auriculata (Aa), and Sphenoclea zeylanica (Sz) were planted into one 16-cm pot for each rate. Seeds from the U.S. of Cyperus iria (Ci), Leptochloa fascicularis (Lf), one stand of 9 or 10 direct-seeded rice seedlings (Oryza sativa cv. ‘Japonica—M202’; Oss), and one stand of 6 trasplanted rice seedlings (Oryza saliva cv. ‘Japonica—M202’; Ost) were planted into one 16-cm pot for each rate. Seeds from the U.S. of Cyperus difformis (Cd), Alisma plantago-aquatica (Ap), and Scirpus mucronatus (Sm) were planted into one 16-cm pot for each rate. Seeds from the U.S. of Echinochloa crus-galli (Ecg), Echinochloa oryzicola (Eor), Echinochloa oryzoides (Eoz) and Echinochloa colonum (Ecc) were planted into one 16-cm pot for each rate. Plantings were sequential so that crop and weed species were at the 2.0 to 2.5-leaf stage at time of treatment.

Potted plants were grown in a greenhouse with day/night temperature settings of 29.5/26.7° C., and supplemental balanced lighting was provided to maintain a 16-hour photoperiod. Test pots were maintained in the greenhouse until test completion.

Chemical treatments consisting of Compound 1 of Index Table A (Cmpd 1), daimuron (Cmpd D), quinoclamine (Cmpd Q) and combinations thereof were formulated in acetone. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Effects of treatments on rice and weeds were visually evaluated by comparison to untreated controls after 21 days. Plant response ratings are reported on a 0 to 100 scale; where 0 is no effect and 100 is complete control. ND means no data.

Colby's equation was used to calculate the expected additive herbicidal effect of the mixtures of Compound 1 with daimuron (Cmpd D) and quinoclamine (Cmpd Q). Colby's equation (Colby, S. R. “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations,” Weeds, 15(1), pp 20-22 (1967)) calculates the expected additive effect of herbicidal mixtures, and for two active ingredients is of the form:
Pa+b=Pa+Pb−(PaPb/100)
wherein

    • Pa+b is the percentage effect of the mixture expected from additive contribution of the individual components,
    • Pa is the observed percentage effect of the first active ingredient at the same use rate as in the mixture, and
    • Pb is the observed percentage effect of the second active ingredient at the same use rate as in the mixture.

Plant response ratings and additive effects expected from the Colby Equation are shown in Table D.

TABLE D Effect of Compound 1, Daimuron, Quinoclamine and Combinations for Controlling Weeds in Rice in Greenhouse Test* Application Rate (g/ha) Oss Ost Sz Hl Mv Cmpd 1 Cmpd D Cmpd Q Obs. Exp. Obs. Exp. Obs. Exp. Obs. Exp. Obs. Exp.  32 0 0 40 — 15 — 100 — ND — 100 —  64 0 0 40 — 0 — 100 — 40 — 100 — 125 0 0 70 — 0 — 100 — 90 — 100 — 250 0 0 100 — 20 — 100 — 100 — 100 — 500 0 0 100 — 60 — 100 — 100 — 100 —  0 500 0 0 — 0 — 20 — 30 — 30 —  32 500 0 0 40 0 15 100 100 0 ND 100 100  64 500 0 35 40 20 0 100 100 40 58 100 100 125 500 0 45 70 20 0 100 100 80 93 100 100 250 500 0 65 100 40 20 100 100 100 100 100 100 500 500 0 85 100 50 60 100 100 100 100 100 100  0 0 500 0 — 0 — 0 — 0 — 0 —  32 0 500 20 40 0 15 100 100 ND ND 100 100  64 0 500 45 40 20 0 100 100 ND 40 100 100 125 0 500 65 70 20 0 100 100 85 90 100 100 250 0 500 85 100 30 20 100 100 100 100 100 100 500 0 500 100 100 70 60 100 100 100 100 100 100 Application Rate (g/ha) Aa Lf Ci Sm Cd Cmpd 1 Cmpd D Cmpd Q Obs. Exp. Obs. Exp. Obs. Exp. Obs. Exp. Obs. Exp.  32 0 0 85 — 90 — 95 — 60 — 100 —  64 0 0 95 — 100 — 100 — 100 — 100 — 125 0 0 100 — 100 — 100 — 100 — 100 — 250 0 0 100 — 100 — 100 — 100 — 100 — 500 0 0 100 — 100 — 100 — 100 — 100 —  0 500 0 0 — 0 — 0 — ND — 60 —  32 500 0 95 85 98 90 98 95 95 ND 100 100  64 500 0 100 95 98 100 100 100 100 ND 100 100 125 500 0 100 100 100 100 100 100 100 ND 100 100 250 500 0 100 100 100 100 100 100 100 ND 100 100 500 500 0 100 100 100 100 100 100 100 ND 100 100  0 0 500 0 — 0 — 0 — 0 — 35 —  32 0 500 90 85 85 90 100 95 90 60 100 100  64 0 500 100 95 100 100 100 100 100 100 100 100 125 0 500 100 100 100 100 100 100 100 100 100 100 250 0 500 100 100 100 100 100 100 100 100 100 100 500 0 500 100 100 100 100 100 100 100 100 100 100 Application Rate (g/ha) Ap Ecg Eor Eoz Ecc Cmpd 1 Cmpd D Cmpd Q Obs. Exp. Obs. Exp. Obs. Exp. Obs. Exp. Obs. Exp.  32 0 0 100 — 0 — 0 — 20 — 0 —  64 0 0 100 — 85 — 30 — 100 — 100 — 125 0 0 100 — 100 — 40 — 100 — 100 — 250 0 0 100 — 100 — 100 — 100 — 100 — 500 0 0 100 — 100 — 100 — 100 — 100 —  0 500 0 0 — 0 — 0 — 0 — 0 —  32 500 0 85 100 0 0 0 0 60 20 60 0  64 500 0 100 100 100 85 65 30 100 100 100 100 125 500 0 100 100 100 100 100 40 100 100 100 100 250 500 0 100 100 100 100 100 100 100 100 100 100 500 500 0 100 100 100 100 100 100 100 100 100 100  0 0 500 60 — 0 — 30 — 0 — 0 —  32 0 500 100 100 40 0 0 30 100 20 40 0  64 0 500 100 100 100 85 35 51 100 100 85 100 125 0 500 100 100 100 100 75 58 100 100 100 100 250 0 500 100 100 100 100 100 100 100 100 100 100 500 0 500 100 100 100 100 100 100 100 100 100 100
*Obs. is observed effect. Exp. is additive effect expected by calculation according to Colby, S. R. “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations,” Weeds, 15(1), pp 20-22 (1967).

As can be seen from the results listed in Table C for this test, mixtures of daimuron and quinoclamine with Compound 1 reduced phytotoxicity on direct-seeded rice (Oss), daimuron being more effective than quinoclamine in this regard. In contrast to the safening on rice, these combinations generally retain excellent effect for controlling weeds. The results suggest some synergism of mixtures of Compound 1 with daimuron on Ammania auriculata (Aa) and mixtures of Compound 1 with quinoclamine on Ammania auriculata (Aa) and Scirpus mucronatus (Sm). Mixtures of Compound 1 with daimuron showed synergism on all four Echinochloa species, E. crus-galli (Ecg), E. oryzicola (Eor), E. oryzoides (Eoz) and E. colonum (Ecc), while mixtures of Compound 1 with quinoclamine show synergism on two species, E. crus-galli (Ecg) and E. oryzoides (Eoz). The synergism on Echinochloa species with safening on direct-seeded rice is particularly surprising, as both Echinochloa species and rice are grasses.

Claims

1. A compound selected from Formula 1, an N-oxide or an agriculturally suitable salt thereof, wherein:

A is an optionally substituted aryl or heteroaromatic ring, wherein the optional substituents are selected from halogen, cyano, C1-C6 alkyl, C1-C4 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, OR8, —S(O)kR9, —C(O)R10, —C(O)OR11 and —C(O)NR12R13; two substituents of the group A may combine to form a fused 5- or 6-membered saturated or partially saturated carbocyclic or heterocyclic ring, and said fused ring system is optionally substituted with one or more R7;
Y is O or S;
Z is O, S(O)n or CR3R4;
W is (CR3R4)q;
R1 is H, C1-C12 alkyl, C1-C12 haloalkyl, C3-C12 cycloalkyl, C3-C12 halocycloalkyl, C4-C12 alkylcycloalkyl, C4-C12 alkylhalocycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, di-(C1-C2 alkyl)amino, Cl, Br, I, —C(O)R5, —C(O)OR5, —C(O)NR5R6 or tri(C1-C4 alkyl)silyl;
R2a is H, C1-C4 alkyl or C1-C4 haloalkyl; and R2a only exists when the carbon atom to which it is connected is a quaternary carbon center in which case the dotted line in Formula 1, together with the parallel solid line, represents a single bond;
R2b is H, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, F or Cl; or
R1 and R2b are taken together as —C(R3R4)CH2CH2—, —C(R3R4)CH2CH2CH2— or —(CH2)mO(CH2)t—;
each R3 and R4 are independently H, C1-C6 alkyl or C1-C6 haloalkyl;
R5 is C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl or C1-C6 haloalkyl;
R6 is H or C1-C6 alkyl;
each R7 is independently C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, halogen, CN, NO2 or hydroxy;
each R8 is independently C1-C4 alkyl or C1-C4 haloalkyl;
each R9 is independently C1-C4 alkyl or C1-C4 haloalkyl;
each R10 is independently C1-C4 alkyl or C1-C4 haloalkyl;
each R11 is independently C1-C4 alkyl, C1-C3 haloalkyl, 4 alkenyl, C2-haloalkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C3-C5 halocycloalkyl, C3-C6 cycloalkenyl or C4-C6 cycloalkylalkyl;
each R12 is independently H or C1-C2 alkyl;
each R13 is independently C1-C4 alkyl; or
R12 and R13 are taken together as —(CH2)4—, —(CH2)5— or —(CH2)2O(CH2)2—;
each k is independently 0, 1 or 2;
n is 0, 1 or 2;
q is 1 or 2;
m is 0, 1 or 2;
t is 0, 1 or 2; and
m+t is 2 or 3;
provided that:
(a) each position on the aryl or heteroaromatic ring A vicinal (ortho) to the point of attachment of the aryl or heteroaromatic ring to the Formula 1 backbone is independently substituted with fluorine or not substituted;
(b) when A is a phenyl ring with a fluorine substituent meta to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone, then attached at the other meta position of the phenyl ring is a substituent other than fluorine;
(c) when A is a phenyl ring with at least one —C(O)NR12R13 substituent, then the at least one —C(O)NR12R13 substituent is at a position other than meta to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone;
(d) when A is a phenyl ring, the position para to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone is unsubstituted or substituted by a substituent other than alkoxy,
(e) when A is a phenyl ring with a —C(O)OR11 substituent at the position para to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone, then a substituent is attached to a position on the phenyl ring meta to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone;
(f) when A is a pyridine ring connected at the 2-position to the remainder of the Formula 1 backbone and methyl is at the 6-position of the pyridine ring, then the pyridine ring is substituted at the 4-position;
(g) when A is a pyrimidine ring connected at the 2-position to the remainder of the Formula 1 backbone, and when the 4-position of the pyrimidine ring is unsubstituted or is substituted with methyl, then the substituent at the 6-position of the pyrimidine ring is other than methyl, and when a methoxy substituent is at the 4-position of the pyrimidine ring, then the substituent at the 6-position of the pyrimidine ring is other than methoxy,
(h) when A is an isothiazole ring connected at the 5-position to the remainder of the Formula 1 backbone, then the isothiazole ring is substituted with a substituent other than alkyl;
(i) when R1 is a C3-C12 alkoxy group, then the alkyl moiety of the alkoxy group is branched at the carbon atom attached to the oxygen atom;
(j) when R1 and R2b are taken together as —C(R3R4)CH2CH2—, —C(R3R4)CH2CH2CH2— or —(CH2)mO(CH2)t— then Z is O or CR3R4; and
(k) when R2b is connected to a quaternary carbon center, then R2b is H, C1-C4 alkyl or C1-C4 haloalkyl.

2. The compound of claim 1 wherein A is substituted phenyl or 5 or 6-membered heterocyclic ring comprising 0-3 nitrogen atoms, 0-1 oxygen atoms and 0-1 sulfur atoms in said ring.

3. The compound of claim 2 wherein

A is
R14 is H, halogen, cyano, C1-C6 alkyl, C1-C4 haloalkyl, OR8, —S(O)kR9, —C(O)R10 or —C(O)OR11; such that R14 is bound to a ring atom joined through one intervening ring atom to the ring atom lining the ring to the remainder of Formula 1;
each R15 is independently halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C1-C4 haloalkoxy; or
R14 taken together with an adjacent R15 is —(CH2)3—, —(CH2)4—, —O(CH2)2—, —O(CH2)3—, —S(CH2)2— or —S(CH2)3—, each optionally substituted with 1-3 substituents selected from CH3, CH2CH3 and F;
Y1 is O, S or N—H; such that when Y1 is N—H, the H of N—H may be replaced by an R14 or R15 substituent selected from alkyl, or the H of N—H may be replaced by the bond linking the ring to the remainder of Formula 1;
p1 is 0, 1, 2 or 3;
p2 is 0, 1 or 2;
p3 is 0 or 1;
provided that at least one R14 or R15 is other than H.

4. The compound of claim 3 wherein

Y is O;
Z is O, S or CH2;
W is CH2;
R1 is C1-C12 alkyl or C3-C12 cycloalkyl;
R2a is H; and
R2b is H or C1-C4 alkyl.

5. The compound of claim 4 wherein the dotted line in Formula 1, together with the parallel solid line, represents a double bond; and

R2b is H.

6. The compound of claim 5 wherein

A is A1, A2 or A6;
Y1 is O or S;
R14 is halogen, C1-C6 alkyl, C1-C4 haloalkyl, OR8, —S(O)kR9, —C(O)R10 or —C(O)OR11;
R15 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C1-C4 haloalkoxy,
or R14 taken together with an adjacent R15 is —(CH2)3—, —(CH2)4—, —O(CH2)2—, —O(CH2)3—, —S(CH2)2— or —S(CH2)3—, each optionally substituted with 1-2 CH3, CH2CH3 or F; such that the left-hand bond is connected at the R14 position and the right-hand bond is connected at the R15 position;
p1 is 0 or 1; and
p2 is 0 or 1.

7. The compound of claim 6 wherein

R1 is branched C3-C8 alkyl or C4-C6 cycloalkyl.

8. The compound of claim 7 wherein

R1 is isopropyl, tert-butyl, sec-butyl or 3-pentyl.

9. The compound of claim 6 wherein

Y1 is S; and
R14 is Br, C1-C6 alkyl, CF2H, CF3, C1-C4 alkoxy, OCF3, OCF2H, —C(O)R10 or —C(O)OR11;
R15 is halogen, C1-C2 alkyl or C1-C2 alkoxy;
R10 is C1-C2 alkyl; and
R11 is C1-C2 alkyl.

10. The compound of claim 9 wherein

R14 is Br, C1-C5 alkyl, CF2H, CF3, C1-C4 alkoxy, OCF3, OCF2H or —C(O)OCH3.

11. The compound of claim 10 wherein

R15 is C1-C2 alkyl.

12. The compound of claim 11 wherein

p1 is 0; and
p2 is 0.

13. The compound of claim 6 wherein

R15 is CH3.

14. The compound of claim 13 wherein

p1 is 0, and
p2 is 0.

15. The compound of claim 6 wherein

A is A1;
R14 is C1-C4 alkoxy;
R15 is CH3, F, Cl or Br and is in the para position relative to the bond connecting A to the remainder of Formula 1; and
p1 is 1.

16. The compound of claim 1 which is selected from the group consisting of:

(a) 5-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone;
(b) 3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone;
(c) 5-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone;
(d) 3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-1-(3-methoxy-4-methylphenyl)-2-pyrrolidinone;
(e) 5-[3-(1-methylpropyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone;
(f) 5-[3-(1-ethylpropyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone;
(g) 1-(4-chloro-3-methoxyphenyl)-3-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-2-pyrrolidinone; and
(h) 1-(4-chloro-3-methoxyphenyl)-3-[3-(1-ethylpropyl)-1H-pyrazol-1-yl]-2-pyrrolidinone.

17. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 1 and at least one of a surfactant, a solid diluent or a liquid diluent.

18. A composition of claim 17 further comprising a herbicidally effective amount of daimuron.

19. A composition of claim 17 further comprising a herbicidally effective amount of quinoclamine.

20. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of claim 1.

Patent History
Publication number: 20060229205
Type: Application
Filed: May 31, 2006
Publication Date: Oct 12, 2006
Inventors: Clifford Cotterman (Newark, DE), Chi-Ping Tseng (Wilmington, DE)
Application Number: 11/443,673
Classifications
Current U.S. Class: 504/230.000; 544/209.000; 544/238.000; 544/331.000; 546/269.700; 546/275.100; 504/236.000; 504/239.000; 504/266.000; 504/270.000; 504/280.000; 548/311.100
International Classification: A01N 43/66 (20060101); A01N 43/58 (20060101); A01N 43/54 (20060101); A01N 43/78 (20060101); A01N 43/76 (20060101); A01N 43/56 (20060101); C07D 417/02 (20060101); C07D 413/02 (20060101); C07D 403/02 (20060101);