Substituted benzoylisoxazoles and the use thereof as herbicides

Info

Publication number: 20050079979
Type: Application
Filed: Sep 30, 2004
Publication Date: Apr 14, 2005
Inventors: Klaus-Helmut Muller (Dusseldorf), Stefan Lehr (Langenfeld), Otto Schallner (Monheim), Hans-Georg Schwarz (Langenfeld), Heinz-Jurgen Wroblowsky (Langenfeld), Mark Drewes (Langenfeld), Dieter Feucht (Monheim), Rolf Pontzen (Leichlingen), Ingo Wetcholowsky (Cond. Estancia Marambaia)
Application Number: 10/954,396

Abstract

The invention relates to novel substituted benzoylisoxazoles of the general formula (I), in which n, A, R1, R2, R3, R4, and Z are defined herein, and to processes for their preparation and to their use as herbicides.

Description

Description

The invention relates to novel substituted benzoylisoxazoles, to processes for their preparation and to their use as herbicides.

It is already known that certain substituted benzoylisoxazoles have herbicidal properties (cf. EP-A-418 175, EP-A-487 357, EP-A-527 036, EP-A-527 037, EP-A-560 483, EP-A-609 797, EP-A-609 798, EP-A-636 622, U.S. Pat. No. 5,834,402, U.S. Pat. No. 5,863,865, WO-A-96/26192, WO-A-97/27187, WO-A-97/43270, WO-A-99/03856). However, the activity of these compounds is not entirely satisfactory.

This invention, accordingly, provides the novel compounds of the general formula (I),
in which

- n represents the number 0, 1, 2 or 3,
- A represents a single bond or represents alkanediyl (alkylene),
- R¹represents hydrogen or represents in each case optionally substituted alkyl, alkenyl or cycloalkyl,
- R²represents hydrogen, cyano, carbamoyl, halogen, or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl,
- R³represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl,
- R⁴represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl, and
- Z represents an optionally substituted 4- to 12-membered, saturated or unsaturated, monocyclic or bicyclic, heterocyclic grouping which contains 1 to 4 hetero atoms (up to 4 nitrogen atoms and optionally—alternatively or additionally—one oxygen atom or one sulphur atom, or one SO grouping or one SO₂grouping) and which additionally contains one to three oxo groups (C═O) and/or thioxo groups (C═S) as components of the heterocycle.

In the definitions, the hydrocarbon chains, such as alkyl or alkanediyl—including in combination with hetero atoms, such as alkoxy—are in each case straight-chain or branched.

- n preferably represents the number 0, 1 or 2.
- A preferably represents a single bond or represents alkanediyl (alkylene) having 1 to 4 carbon atoms.
- R¹preferably represents hydrogen, represents optionally cyano-, halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- or C₁-C₄-alkyl-sulphonyl-substituted alkyl having 1 to 6 carbon atoms, represents optionally cyano- or halogen-substituted alkenyl having 2 to 6 carbon atoms, or represents optionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms.
- R²preferably represents hydrogen, cyano, carbamoyl, halogen, represents in each case optionally cyano-, halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alky, alkylcarbonyl, alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms, or represents in each case optionally halogen-substituted alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms.
- R³preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thio-carbamoyl, halogen, represents in each case optionally halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 4 carbon atoms in the alkyl groups, or represents alkylamino, dialkylamino or dialkylaminosulphonyl having in each case up to 4 carbon atoms in the alkyl groups.
- R⁴preferably represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, represents in each case optionally halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 4 carbon atoms in the alkyl groups, or represents alkylamino, dialkylamino or dialkylaminosulphonyl having in each case up to 4 carbon atoms in the alkyl groups, and
- Z preferably represents one of the heterocyclic groupings below
  in which the dotted bond is in each case a single bond or a double bond, and each heterocyclic grouping preferably only carries two substituents of the definition R⁵and/or R⁶,
- Q represents oxygen or sulphur,
- R⁵represents hydrogen, hydroxyl, mercapto, cyano, halogen, represents in each case optionally cyano-, halogen-, C₁-C₄-alkoxy, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkylamino or dialkylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl, alkenyloxy, alkenylthio, alkinylthio or alkenylamino having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino, piperidino or morpholino, or—if two adjacent radicals R⁵and R⁵are located at a double bond—also together with the adjacent radical R⁵represents a benzo grouping, and
- R⁶represents hydrogen, hydroxyl, amino, alkylidenamino having up to 4 carbon atoms, represents in each case optionally halogen- or C₁-C₄-alkoxy-substituted alkyl, alkoxy, alkylamino, dialkylamino or alkanoylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl or alkenyloxy having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkylalkyl or cycloalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 3 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted phenyl or benzyl, or together with an adjacent radical R⁵or R⁶represents optionally halogen- or C₁-C₄-alkyl-substituted alkanediyl having 3 to 5 carbon atoms,
- where the individual radicals R⁵and R⁶—if a plurality of them are attached to the same heterocyclic grouping—can have identical or different meanings within the scope of the above definition.
- Q preferably represents oxygen (O).
- R⁵preferably represents hydrogen, hydroxyl, mercapto, cyano, fluorine, chlorine, bromine, iodine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphihyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, di-n-propylamino or di-i-propylamino, represents in each case optionally fluorine- and/or chlorine-substituted ethenyl, propenyl, butenyl, ethinyl, propinyl, butinyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino or butenylamino, represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- or i-propoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino, piperidino or morpholino, or—if two adjacent radicals R⁵and R⁵are located at a double bond—together with the adjacent radical R⁵also represents a benzo grouping.
- R⁶preferably represents hydrogen, hydroxyl, amino, represents in each case optionally fluorine- and/or chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino or dimethylamino, represents in each case optionally fluorine- and/or chlorine-substituted ethenyl, propenyl, ethinyl, propinyl or propenyloxy, represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, or represents in each case optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- or i-propoxy-substituted phenyl or benzyl, or together with an adjacent radical R⁵or R⁶represents in each case optionally methyl- and/or ethyl-substituted propane-1,3-diyl (trimethylene) or butane-1,4-diyl (tetramethylene).
- A particularly preferably represents a single bond, methylene, ethylidene (ethane-1,1-diyl) or dimethylene (ethane-1,2-diyl).
- R¹particularly preferably represents hydrogen, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
- R²particularly preferably represents hydrogen, cyano, carbamoyl, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or represents in each case optionally fluorine- and/or chlorine-substituted methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl or ethylsulphonyl.
- R³particularly preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine,-bromine, iodine, represents in each case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, represents in each case optionally fluorine- and/or chlorine-substituted methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or represents methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, dimethylaminosulphonyl or diethylaminosulphonyl.
- R⁴particularly preferably represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, represents in each case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, represents in each case optionally fluorine- and/or chlorine-substituted methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or represents methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, dimethylaminosulphonyl or diethylaminosulphonyl.
- Z particularly preferably represents the heterocyclic groupings
  R⁵particularly preferably represents hydrogen, hydroxyl, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, fluoro-n-propyl, fluoro-i-propyl, chloro-n-propyl, chloro-i-propyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, trifluoroethoxy, trichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy, fluorodichloroethoxy, methylthio, ethylthio, n- or i-propylthio, fluoroethylthio, chloroethylthio, difluoroethylthio, dichloroethylthio, chlorofluoroethylthio, chlorodifluoroethylthio, fluorodichloroethylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, dimethylamino, propenylthio, butenylthio, propinylthio, butinylthio, cyclopropyl, cyclopropylmethyl, cyclopropylmethoxy, phenyl or phenoxy.
- R⁶particularly preferably represents amino, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylamino, dimethylamino, cyclopropyl or cyclopropylmethyl, or together with R⁵represents propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) or pentane-1,5-diyl (pentamethylene).
- A very particularly preferably represents a single bond or represents methylene.
- R¹very particularly preferably represents hydrogen, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents optionally cyano-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl.
- R²very particularly preferably represents hydrogen, cyano, carbamoyl, fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or represents in each case optionally fluorine- and/or chlorine-substituted methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl.
- R³very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, methoxymethyl, methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl or dimethylaminosulphonyl.
- R⁴very particularly preferably represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxymethyl, methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl or dimethylaminosulphonyl.
- A most preferably represents methylene.
- R¹most preferably represents cyclopropyl.
- R²most preferably represents hydrogen, methoxycarbonyl or ethoxycarbonyl.
- R³most preferably represents chlorine, bromine, cyano, trifluoromethyl or methylsulphonyl.
- R⁴most preferably represents hydrogen, cyano, chlorine, nitro, methyl, trifluoromethyl, methoxy or methylsulphonyl.

Preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.

Particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.

Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.

Most preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being most preferred.

Among the meanings given as preferred, particularly preferred, very particularly preferred or most preferred, still greater emphasis is given to the compounds of the general formula (IA)
in which

- n, A, Q, R¹, R², R³, R⁴, R⁵and R⁶are each as defined above, with very particular emphasis on the compounds of the formula (IA) in which A represents methylene.

Moreover, among the meanings given as being preferred, particularly preferred, very particularly preferred or most particularly preferred, still greater emphasis is given to the compounds of the general formula (IB)
in which

- n, A, Q, R¹, R², R³, R⁴, R⁵and R⁶are each as defined above.

Furthermore, among the meanings given as being preferred, particularly preferred, very particularly preferred or most preferred, still greater emphasis is given to those compounds of the general formula (IC)
in which

- n, A, Q, R¹, R², R³, R⁴, R⁵and R⁶are each as defined above.

The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, i.e. including combinations between the given preferred ranges.

Examples of compounds of the general formula (I) according to the invention are listed in the groups below.
Group 1

Here, R³, (R⁴)_n, R⁵and R⁶each have, for example, the meanings given in the table below:

R³ (position-) (R⁴)_n R⁵ R⁶ H — CF₃ CH₃ F — CF₃ CH₃ Cl — CF₃ CH₃ Br — CF₃ CH₃ I — CF₃ CH₃ NO₂ — CF₃ CH₃ CN — CF₃ CH₃ CH₃ — CF₃ CH₃ OCH₃ — CF₃ CH₃ CF₃ — CF₃ CH₃ OCHF₂ — CF₃ CH₃ OCF₃ — CF₃ CH₃ SO₂CH₃ — CF₃ CH₃ H — OCH₃ CH₃ F — OCH₃ CH₃ Cl — OCH₃ CH₃ Br — OCH₃ CH₃ I — OCH₃ CH₃ NO₂ — OCH₃ CH₃ CN — OCH₃ CH₃ CH₃ — OCH₃ CH₃ OCH₃ — OCH₃ CH₃ CF₃ — OCH₃ CH₃ OCHF₂ — OCH₃ CH₃ OCF₃ — OCH₃ CH₃ SO₂CH₃ — OCH₃ CH₃ H — SCH₃ CH₃ F — SCH₃ CH₃ Cl — SCH₃ CH₃ Br — SCH₃ CH₃ I — SCH₃ CH₃ NO₂ — SCH₃ CH₃ CN — SCH₃ CH₃ CH₃ — SCH₃ CH₃ OCH₃ — SCH₃ CH₃ CF₃ — SCH₃ CH₃ OCHF₂ — SCH₃ CH₃ OCF₃ — SCH₃ CH₃ SO₂CH₃ — SCH₃ CH₃ H — OC₂H₅ CH₃ F — OC₂H₅ CH₃ Cl — OC₂H₅ CH₃ Br — OC₂H₅ CH₃ I — OC₂H₅ CH₃ NO₂ — OC₂H₅ CH₃ CN — OC₂H₅ CH₃ CH₃ — OC₂H₅ CH₃ OCH₃ — OC₂H₅ CH₃ CF₃ — OC₂H₅ CH₃ OCHF₂ — OC₂H₅ CH₃ OCF₃ — OC₂H₅ CH₃ SO₂CH₃ — OC₂H₅ CH₃ H — N(CH₃)₂ CH₃ F — N(CH₃)₂ CH₃ Cl — N(CH₃)₂ CH₃ Br — N(CH₃)₂ CH₃ I — N(CH₃)₂ CH₃ NO₂ — N(CH₃)₂ CH₃ CN — N(CH₃)₂ CH₃ CH₃ — N(CH₃)₂ CH₃ OCH₃ — N(CH₃)₂ CH₃ CF₃ — N(CH₃)₂ CH₃ OCHF₂ — N(CH₃)₂ CH₃ OCF₃ — N(CH₃)₂ CH₃ SO₂CH₃ — N(CH₃)₂ CH₃ H — OCH₃ F — OCH₃ Cl — OCH₃ Br — OCH₃ I — OCH₃ NO₂ — OCH₃ CN — OCH₃ CH₃ — OCH₃ OCH₃ — OCH₃ CF₃ — OCH₃ OCHF₂ — OCH₃ OCF₃ — OCH₃ SO₂CH₃ — OCH₃ H (3-) Cl CF₃ CH₃ F (3-) Cl CH₃ CH₃ Cl (3-) Cl OCH₃ CH₃ Br (3-) Cl Br Cl (3-) Cl CF₃ Cl3 NO₂ (3-) Cl CH₃ CH₃ Cl (3-) Cl SCH₃ CH₃ CH₃ (3-) Cl Cl CH₃ OCH₃ (3-) Cl OCH₃ CH₃ CF₃ (3-) Cl CF₃ CH₃ OCHF₂ (3-) Cl CH₃ CH₃ OCF₃ (3-) Cl CH₃ CH₃ SO₂CH₃ (3-) Cl OCH₃ CH₃

Group 2

Here, R³, (R⁴)_n, R⁵and R⁶each have, for example, the meanings given for Group 1.
Group 3

Here, R³, (R⁴)_n, R⁵and R⁶each have, for example, the meanings given for Group 1.
Group 4

Here, R³, (R⁴)_n, R⁵and R⁶each have, for example, the meanings given for Group 1, and m represents the number 0, 1 or 2.
Group 5

Here, R³, (R⁴)_n, R⁵and R⁶each have, for example, the meanings given for Group 1.
Group 6

Here, R³, (R⁴)_n, R⁵and R⁶each have, for example, the meanings given for Group 1.
Group 7
Here, R³, (R⁴)_n, R⁵and R⁶each have, for example, the meanings given for Group 1.
Group 8

Here, R³, (R⁴)_n, R⁵and R⁶each have, for example, the meanings given for group 1, and m represents the number 0, 1 or 2.
Group 9

Here, R³, (R⁴)_n, R⁵and R⁶each have, for example, the meanings given in the table below:

R³ (position-) (R⁴)_n R⁵ R⁶ Cl (2-) Cl CF₃ CH₃ Cl (2-) Cl SCH₃ CH₃ Cl (2-) Cl SC₂H₅ CH₃ Cl (2-) Cl SC₃H₇ CH₃ Cl (2-) Cl SC₃H₇-i CH₃ Cl (2-) Cl CH₃ Cl (2-) Cl CH₃ Cl (2-) Cl CH₃ Cl (2-) Cl CH₃ Cl (2-) Cl CH₃ Cl (2-) Cl SCH═C═CH₂ CH₃ Cl (2-) Cl SCH₂CN CH₃ Cl (2-) Cl SCH₂CH₂CN CH₃ Cl (2-) Cl OCH₃ CH₃ Cl (2-) Cl OC₂H₅ CH₃ Cl (2-) Cl OC₃H₇ CH₃ Cl (2-) Cl OC₃H₇-i CH₃ Cl (2-) Cl OC₄H₉ CH₃ Cl (2-) Cl OCH₂CF₃ CH₃ Cl (2-) Cl CH₃ Cl (2-) Cl OC₆H₅ CH₃ Cl (2-) Cl H CH₃ Cl (2-) Cl CH₃ CH₃ Cl (2-) Cl C₂H₅ CH₃ Cl (2-) Cl C₃H₇ CH₃ Cl (2-) Cl C₃H₇-i CH₃ Cl (2-) Cl C₄H₉ CH₃ Cl (2-) Cl C₄H₉-i CH₃ Cl (2-) Cl C₄H₉-s CH₃ Cl (2-) Cl C₄H₉-t CH₃ Cl (2-) Cl CH₃ Cl (2-) Cl CH₃ Cl (2-) Cl CH═CHCH₃ CH₃ Cl (2-) Cl CH₃ Cl (2-) Cl CH₃ Cl (2-) Cl CH₃ Cl (2-) Cl N(CH₃)₂ CH₃ Cl (2-) Cl CH₃ Cl (2-) Cl Cl CH₃ Cl (2-) Cl Br CH₃ SO₂CH₃ (2-) Cl CF₃ CH₃ SO₂CH₃ (2-) Cl SCH₃ CH₃ SO₂CH₃ (2-) Cl SC₂H₅ CH₃ SO₂CH₃ (2-) Cl SC₃H₇ CH₃ SO₂CH₃ (2-) Cl SC₃H₇-i CH₃ SO₂CH₃ (2-) Cl CH₃ SO₂CH₃ (2-) Cl CH₃ SO₂CH₃ (2-) Cl CH₃ SO₂CH₃ (2-) Cl CH₃ SO₂CH₃ (2-) Cl CH₃ SO₂CH₃ (2-) Cl SCH═C═CH₂ CH₃ SO₂CH₃ (2-) Cl SCH₂CN CH₃ SO₂CH₃ (2-) Cl SCH₂CH₂CN CH₃ SO₂CH₃ (2-) Cl OCH₃ CH₃ SO₂CH₃ (2-) Cl OC₂H₅ CH₃ SO₂CH₃ (2-) Cl OC₃H₇ CH₃ SO₂CH₃ (2-) Cl OC₃H₇-i CH₃ SO₂CH₃ (2-) Cl OC₄H₉ CH₃ SO₂CH₃ (2-) Cl OCH₂CF₃ CH₃ SO₂CH₃ (2-) Cl CH₃ SO₂CH₃ (2-) Cl OC₆H₅ CH₃ SO₂CH₃ (2-) Cl H CH₃ SO₂CH₃ (2-) Cl CH₃ CH₃ SO₂CH₃ (2-) Cl C₂H₅ CH₃ SO₂CH₃ (2-) Cl C₃H₇ CH₃ SO₂CH₃ (2-) Cl C₃H₇-i CH₃ SO₂CH₃ (2-) Cl C₄H₉ CH₃ SO₂CH₃ (2-) Cl C₄H₉-i CH₃ SO₂CH₃ (2-) Cl C₄H₉-s CH₃ SO₂CH₃ (2-) Cl C₄H₉-t CH₃ SO₂CH₃ (2-) Cl CH₃ SO₂CH₃ (2-) Cl CH₃ SO₂CH₃ (2-) Cl CH═CHCH₃ CH₃ SO₂CH₃ (2-) Cl CH₃ SO₂CH₃ (2-) Cl CH₃ SO₂CH₃ (2-) Cl CH₃ SO₂CH₃ (2-) Cl N(CH₃)₂ CH₃ SO₂CH₃ (2-) Cl CH₃ SO₂CH₃ (2-) Cl Cl CH₃ SO₂CH₃ (2-) Cl Br CH₃ Cl (2-) SO₂CH₃ CF₃ CH₃ Cl (2-) SO₂CH₃ SCH₃ CH₃ Cl (2-) SO₂CH₃ SC₂H₅ CH₃ Cl (2-) SO₂CH₃ SC₃H₇ CH₃ Cl (2-) SO₂CH₃ SC₃H₇-i CH₃ Cl (2-) SO₂CH₃ CH₃ Cl (2-) SO₂CH₃ CH₃ Cl (2-) SO₂CH₃ CH₃ Cl (2-) SO₂CH₃ CH₃ Cl (2-) SO₂CH₃ CH₃ Cl (2-) SO₂CH₃ SCH═C═CH₂ CH₃ Cl (2-) SO₂CH₃ SCH₂CN CH₃ Cl (2-) SO₂CH₃ SCH₂CH₂CN CH₃ Cl (2-) SO₂CH₃ OCH₃ CH₃ Cl (2-) SO₂CH₃ OC₂H₅ CH₃ Cl (2-) SO₂CH₃ OC₃H₇ CH₃ Cl (2-) SO₂CH₃ OC₃H₇-i CH₃ Cl (2-) SO₂CH₃ OC₄H₉ CH₃ Cl (2-) SO₂CH₃ OCH₂CF₃ CH₃ Cl (2-) SO₂CH₃ CH₃ Cl (2-) SO₂CH₃ OC₆H₅ CH₃ Cl (2-) SO₂CH₃ H CH₃ Cl (2-) SO₂CH₃ CH₃ CH₃ Cl (2-) SO₂CH₃ C₂H₅ CH₃ Cl (2-) SO₂CH₃ C₃H₇ CH₃ Cl (2-) SO₂CH₃ C₃H₇-i CH₃ Cl (2-) SO₂CH₃ C₄H₉ CH₃ Cl (2-) SO₂CH₃ C₄H₉-i CH₃ Cl (2-) SO₂CH₃ C₄H₉-s CH₃ Cl (2-) SO₂CH₃ C₄H₉-t CH₃ Cl (2-) SO₂CH₃ CH₃ Cl (2-) SO₂CH₃ CH₃ Cl (2-) SO₂CH₃ CH═CHCH₃ CH₃ Cl (2-) SO₂CH₃ CH₃ Cl (2-) SO₂CH₃ CH₃ Cl (2-) SO₂CH₃ CH₃ Cl (2-) SO₂CH₃ N(CH₃)₂ CH₃ Cl (2-) SO₂CH₃ CH₃ Cl (2-) SO₂CH₃ Cl CH₃ Cl (2-) SO₂CH₃ Br CH₃ Cl (2-) Cl CF₃ Cl (2-) Cl SCH₃ Cl (2-) Cl SC₂H₅ Cl (2-) Cl SC₃H₇ Cl (2-) Cl SC₃H₇-i Cl (2-) Cl Cl (2-) Cl Cl (2-) Cl Cl (2-) Cl Cl (2-) Cl Cl (2-) Cl SCH═C═CH₂ Cl (2-) Cl SCH₂CN Cl (2-) Cl SCH₂CH₂CN Cl (2-) Cl OCH₃ Cl (2-) Cl OC₂H₅ Cl (2-) Cl OC₃H₇ Cl (2-) Cl OC₃H₇-i Cl (2-) Cl OC₄H₉ Cl (2-) Cl OCH₂CF₃ Cl (2-) Cl Cl (2-) Cl OC₆H₅ Cl (2-) Cl H Cl (2-) Cl CH₃ Cl (2-) Cl C₂H₅ Cl (2-) Cl C₃H₇ Cl (2-) Cl C₃H₇-i Cl (2-) Cl C₄H₉ Cl (2-) Cl C₄H₉-i Cl (2-) Cl C₄H₉-s Cl (2-) Cl C₄H₉-t Cl (2-) Cl Cl (2-) Cl Cl (2-) Cl CH═CHCH₃ Cl (2-) Cl Cl (2-) Cl Cl (2-) Cl Cl (2-) Cl N(CH₃)₂ Cl (2-) Cl Cl (2-) Cl Cl Cl (2-) Cl Br SO₂CH₃ (2-) Cl CF₃ SO₂CH₃ (2-) Cl SCH₃ SO₂CH₃ (2-) Cl SC₂H₅ SO₂CH₃ (2-) Cl SC₃H₇ SO₂CH₃ (2-) Cl SC₃H₇-i SO₂CH₃ (2-) Cl SO₂CH₃ (2-) Cl SO₂CH₃ (2-) Cl SO₂CH₃ (2-) Cl SO₂CH₃ (2-) Cl SO₂CH₃ (2-) Cl SCH═C═CH₂ SO₂CH₃ (2-) Cl SCH₂CN SO₂CH₃ (2-) Cl SCH₂CH₂CN SO₂CH₃ (2-) Cl OCH₃ SO₂CH₃ (2-) Cl OC₂H₅ SO₂CH₃ (2-) Cl OC₃H₇ SO₂CH₃ (2-) Cl OC₃H₇-i SO₂CH₃ (2-) Cl OC₄H₉ SO₂CH₃ (2-) Cl OCH₂CF₃ SO₂CH₃ (2-) Cl SO₂CH₃ (2-) Cl OC₆H₅ SO₂CH₃ (2-) Cl H SO₂CH₃ (2-) Cl CH₃ SO₂CH₃ (2-) Cl C₂H₅ SO₂CH₃ (2-) Cl C₃H₇ SO₂CH₃ (2-) Cl C₃H₉-i SO₂CH₃ (2-) Cl C₄H₉ SO₂CH₃ (2-) Cl C₄H₉-i SO₂CH₃ (2-) Cl C₄H₉-s SO₂CH₃ (2-) Cl C₄H₉-t SO₂CH₃ (2-) Cl SO₂CH₃ (2-) Cl SO₂CH₃ (2-) Cl CH═CHCH₃ SO₂CH₃ (2-) Cl SO₂CH₃ (2-) Cl SO₂CH₃ (2-) Cl SO₂CH₃ (2-) Cl N(CH₃)₂ SO₂CH₃ (2-) Cl SO₂CH₃ (2-) Cl Cl SO₂CH₃ (2-) Cl Br Cl (2-) SO₂CH₃ CF₃ Cl (2-) SO₂CH₃ SCH₃ Cl (2-) SO₂CH₃ SC₂H₅ Cl (2-) SO₂CH₃ SC₃H₇ Cl (2-) SO₂CH₃ SC₃H₇-i Cl (2-) SO₂CH₃ Cl (2-) SO₂CH₃ Cl (2-) SO₂CH₃ Cl (2-) SO₂CH₃ Cl (2-) SO₂CH₃ Cl (2-) SO₂CH₃ SCH═C═CH₂ Cl (2-) SO₂CH₃ SCH₂CN Cl (2-) SO₂CH₃ SCH₂CH₂CN Cl (2-) SO₂CH₃ OCH₃ Cl (2-) SO₂CH₃ OC₂H₅ Cl (2-) SO₂CH₃ OC₃H₇ Cl (2-) SO₂CH₃ OC₃H₇-i Cl (2-) SO₂CH₃ OC₄H₉ Cl (2-) SO₂CH₃ OCH₂CF₃ Cl (2-) SO₂CH₃ Cl (2-) SO₂CH₃ OC₆H₅ Cl (2-) SO₂CH₃ H Cl (2-) SO₂CH₃ CH₃ Cl (2-) SO₂CH₃ C₂H₅ Cl (2-) SO₂CH₃ C₃H₇ Cl (2-) SO₂CH₃ C₃H₇-i Cl (2-) SO₂CH₃ C₄H₉ Cl (2-) SO₂CH₃ C₄H₉-i Cl (2-) SO₂CH₃ C₄H₉-s Cl (2-) SO₂CH₃ C₄H₉-t Cl (2-) SO₂CH₃ Cl (2-) SO₂CH₃ Cl (2-) SO₂CH₃ CH═CHCH₃ Cl (2-) SO₂CH₃ Cl (2-) SO₂CH₃ Cl (2-) SO₂CH₃ Cl (2-) SO₂CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ Cl (2-) SO₂CH₃ Cl Cl (2-) SO₂CH₃ Br Cl (2-) Cl CF₃ N(CH₃)₂ Cl (2-) Cl SCH₃ N(CH₃)₂ Cl (2-) Cl SC₂H₅ N(CH₃)₂ Cl (2-) Cl SC₃H₇ N(CH₃)₂ Cl (2-) Cl SC₃H₇-i N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ Cl (2-) Cl SCH═C═CH₂ N(CH₃)₂ Cl (2-) Cl SCH₂CN N(CH₃)₂ Cl (2-) Cl SCH₂CH₂CN N(CH₃)₂ Cl (2-) Cl OCH₃ N(CH₃)₂ Cl (2-) Cl OC₂H₅ N(CH₃)₂ Cl (2-) Cl OC₃H₇ N(CH₃)₂ Cl (2-) Cl OC₃H₇-i N(CH₃)₂ Cl (2-) Cl OC₄H₉ N(CH₃)₂ Cl (2-) Cl OCH₂CF₃ N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ Cl (2-) Cl OC₆H₅ N(CH₃)₂ Cl (2-) Cl H N(CH₃)₂ Cl (2-) Cl CH₃ N(CH₃)₂ Cl (2-) Cl C₂H₅ N(CH₃)₂ Cl (2-) Cl C₃H₇ N(CH₃)₂ Cl (2-) Cl C₃H₇-i N(CH₃)₂ Cl (2-) Cl C₄H₉ N(CH₃)₂ Cl (2-) Cl C₄H₉-i N(CH₃)₂ Cl (2-) Cl C₄H₉-s N(CH₃)₂ Cl (2-) Cl C₄H₉-t N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ Cl (2-) Cl CH═CHCH₃ N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ N(CH₃)₂ Cl (2-) Cl N(CH₃)₂ Cl (2-) Cl Cl N(CH₃)₂ Cl (2-) Cl Br N(CH₃)₂ SO₂CH₃ (2-) Cl CF₃ N(CH₃)₂ SO₂CH₃ (2-) Cl SCH₃ N(CH₃)₂ SO₂CH₃ (2-) Cl SC₂H₅ N(CH₃)₂ SO₂CH₃ (2-) Cl SC₃H₇ N(CH₃)₂ SO₂CH₃ (2-) Cl SC₃H₇-i N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ SO₂CH₃ (2-) Cl SCH═C═CH₂ N(CH₃)₂ SO₂CH₃ (2-) Cl SCH₂CN N(CH₃)₂ SO₂CH₃ (2-) Cl SCH₂CH₂CN N(CH₃)₂ SO₂CH₃ (2-) Cl OCH₃ N(CH₃)₂ SO₂CH₃ (2-) Cl OC₂H₅ N(CH₃)₂ SO₂CH₃ (2-) Cl OC₃H₇ N(CH₃)₂ SO₂CH₃ (2-) Cl OC₃H₇-i N(CH₃)₂ SO₂CH₃ (2-) Cl OC₄H₉ N(CH₃)₂ SO₂CH₃ (2-) Cl OCH₂CF₃ N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ SO₂CH₃ (2-) Cl OC₆H₅ N(CH₃)₂ SO₂CH₃ (2-) Cl H N(CH₃)₂ SO₂CH₃ (2-) Cl CH₃ N(CH₃)₂ SO₂CH₃ (2-) Cl C₂H₅ N(CH₃)₂ SO₂CH₃ (2-) Cl C₃H₇ N(CH₃)₂ SO₂CH₃ (2-) Cl C₃H₇-i N(CH₃)₂ SO₂CH₃ (2-) Cl C₄H₉ N(CH₃)₂ SO₂CH₃ (2-) Cl C₄H₉-i N(CH₃)₂ SO₂CH₃ (2-) Cl C₄H₉-s N(CH₃)₂ SO₂CH₃ (2-) Cl C₄H₉-t N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ SO₂CH₃ (2-) Cl CH═CHCH₃ N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ N(CH₃)₂ SO₂CH₃ (2-) Cl N(CH₃)₂ SO₂CH₃ (2-) Cl Cl N(CH₃)₂ SO₂CH₃ (2-) Cl Br N(CH₃)₂ Cl (2-) SO₂CH₃ CF₃ N(CH₃)₂ Cl (2-) SO₂CH₃ SCH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ SC₂H₅ N(CH₃)₂ Cl (2-) SO₂CH₃ SC₃H₇ N(CH₃)₂ Cl (2-) SO₂CH₃ SC₃H₇-i N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ SCH═C═CH₂ N(CH₃)₂ Cl (2-) SO₂CH₃ SCH₂CN N(CH₃)₂ Cl (2-) SO₂CH₃ SCH₂CH₂CN N(CH₃)₂ Cl (2-) SO₂CH₃ OCH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ OC₂H₅ N(CH₃)₂ Cl (2-) SO₂CH₃ OC₃H₇ N(CH₃)₂ Cl (2-) SO₂CH₃ OC₃H₇-i N(CH₃)₂ Cl (2-) SO₂CH₃ OC₄H₉ N(CH₃)₂ Cl (2-) SO₂CH₃ OCH₂CF₃ N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ OC₆H₅ N(CH₃)₂ Cl (2-) SO₂CH₃ H N(CH₃)₂ Cl (2-) SO₂CH₃ CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ C₂H₅ N(CH₃)₂ Cl (2-) SO₂CH₃ C₃H₇ N(CH₃)₂ Cl (2-) SO₂CH₃ C₃H₇-i N(CH₃)₂ Cl (2-) SO₂CH₃ C₄H₉ N(CH₃)₂ Cl (2-) SO₂CH₃ C₄H₉-i N(CH₃)₂ Cl (2-) SO₂CH₃ C₄H₉-s N(CH₃)₂ Cl (2-) SO₂CH₃ C₄H₉-t N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ CH═CHCH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ N(CH₃)₂ Cl (2-) SO₂CH₃ N(CH₃)₂ Cl (2-) SO₂CH₃ Cl N(CH₃)₂ Cl (2-) SO₂CH₃ Br N(CH₃)₂ Cl (2-) Cl CH₃ OCH₃ Cl (2-) Cl C₂H₅ OCH₃ Cl (2-) Cl C₃H₇ OCH₃ Cl (2-) Cl SCH₃ OCH₃ Cl (2-) Cl SC₂H₅ OCH₃ Cl (2-) Cl OCH₃ OCH₃ Cl (2-) Cl OC₂H₅ OCH₃ Cl (2-) Cl CH₃ OC₂H₅ Cl (2-) Cl C₂H₅ OC₂H₅ Cl (2-) Cl C₃H₇ OC₂H₅ Cl (2-) Cl SCH₃ OC₂H₅ Cl (2-) Cl SC₂H₅ OC₂H₅ Cl (2-) Cl OCH₃ OC₂H₅ Cl (2-) Cl OC₂H₅ OC₂H₅ Cl (2-) SO₂CH₃ CH₃ OCH₃ Cl (2-) SO₂CH₃ C₂H₅ OCH₃ Cl (2-) SO₂CH₃ C₃H₇ OCH₃ Cl (2-) SO₂CH₃ SCH₃ OCH₃ Cl (2-) SO₂CH₃ SC₂H₅ OCH₃ Cl (2-) SO₂CH₃ OCH₃ OCH₃ Cl (2-) SO₂CH₃ OC₂H₅ OCH₃ Cl (2-) SO₂CH₃ CH₃ OC₂H₅ Cl (2-) SO₂CH₃ C₂H₅ OC₂H₅ Cl (2-) SO₂CH₃ C₃H₇ OC₂H₅ Cl (2-) SO₂CH₃ SCH₃ OC₂H₅ Cl (2-) SO₂CH₃ SC₂H₅ OC₂H₅ Cl (2-) SO₂CH₃ OCH₃ OC₂H₅ Cl (2-) SO₂CH₃ OC₂H₅ OC₂H₅ SO₂CH₃ (2-) Cl Cl OCH₃ SO₂CH₃ (2-) Cl Br OCH₃ SO₂CH₃ (2-) Cl CH₃ OCH₃ SO₂CH₃ (2-) Cl C₂H₅ OCH₃ SO₂CH₃ (2-) Cl C₃H₇ OCH₃ SO₂CH₃ (2-) Cl SCH₃ OCH₃ SO₂CH₃ (2-) Cl SC₂H₅ OCH₃ SO₂CH₃ (2-) Cl OCH₃ OC₂H₅ SO₂CH₃ (2-) Cl OC₂H₅ OC₂H₅ SO₂CH₃ (2-) Cl CH₃ OC₂H₅ SO₂CH₃ (2-) Cl C₂H₅ OC₂H₅ SO₂CH₃ (2-) Cl C₃H₇ OC₂H₅ SO₂CH₃ (2-) Cl SCH₃ OC₂H₅ SO₂CH₃ (2-) Cl SC₂H₅ OC₂H₅ SO₂CH₃ (2-) Cl OCH₃ OC₂H₅ CF₃ (2-) Cl Br CH₃ CF₃ (2-) Cl SCH₃ CH₃ CF₃ (2-) Cl OCH₃ CH₃ CF₃ (2-) Cl N(CH₃)₂ CH₃ CF₃ (2-) Cl CF₃ CH₃ CF₃ (2-) NO₂ Br CH₃ CF₃ (2-) NO₂ SCH₃ CH₃ CF₃ (2-) NO₂ OCH₃ CH₃ CF₃ (2-) NO₂ N(CH₃)₂ CH₃ CF₃ (2-) NO₂ CF₃ CH₃ CF₃ (2-) CH₃ Br CH₃ CF₃ (2-) CH₃ SCH₃ CH₃ CF₃ (2-) CH₃ OCH₃ CH₃ CF₃ (2-) CH₃ N(CH₃)₂ CH₃ CF₃ (2-) CH₃ CF₃ CH₃ CF₃ (2-) OCH₃ Br CH₃ CF₃ (2-) OCH₃ SCH₃ CH₃ CF₃ (2-) OCH₃ OCH₃ CH₃ CF₃ (2-) OCH₃ N(CH₃)₂ CH₃ CF₃ (2-) OCH₃ CF₃ CH₃ SO₂CH₃ (2-) NO₂ Br CH₃ SO₂CH₃ (2-) NO₂ SCH₃ CH₃ SO₂CH₃ (2-) NO₂ OCH₃ CH₃ SO₂CH₃ (2-) NO₂ N(CH₃)₂ CH₃ SO₂CH₃ (2-) NO₂ CF₃ CH₃ SO₂CH₃ (2-) CF₃ Br CH₃ SO₂CH₃ (2-) CF₃ SCH₃ CH₃ SO₂CH₃ (2-) CF₃ OCH₃ CH₃ SO₂CH₃ (2-) CF₃ N(CH₃)₂ CH₃ SO₂CH₃ (2-) CF₃ CF₃ CH₃ SO₂CH₃ (2-) SO₂CH₃ Br CH₃ SO₂CH₃ (2-) SO₂CH₃ SCH₃ CH₃ SO₂CH₃ (2-) SO₂CH₃ OCH₃ CH₃ SO₂CH₃ (2-) SO₂CH₃ N(CH₃)₂ CH₃ SO₂CH₃ (2-) SO₂CH₃ CF₃ CH₃ CN (2-) Cl Br CH₃ CN (2-) Cl SCH₃ CH₃ CN (2-) Cl OCH₃ CH₃ CN (2-) Cl N(CH₃)₂ CH₃ CN (2-) Cl CF₃ CH₃ CN (2-) NO₂ Br CH₃ CN (2-) NO₂ SCH₃ CH₃ CN (2-) NO₂ OCH₃ CH₃ CN (2-) NO₂ N(CH₃)₂ CH₃ CN (2-) NO₂ CF₃ CH₃ CN (2-) CF₃ Br CH₃ CN (2-) CF₃ SCH₃ CH₃ CN (2-) CF₃ OCH₃ CH₃ CN (2-) CF₃ N(CH₃)₂ CH₃ CN (2-) CF₃ CF₃ CH₃ CN (2-) SO₂CH₃ Br CH₃ CN (2-) SO₂CH₃ SCH₃ CH₃ CN (2-) SO₂CH₃ OCH₃ CH₃ CN (2-) SO₂CH₃ N(CH₃)₂ CH₃ CN (2-) SO₂CH₃ CF₃ CH₃ Br (2-) NO₂ Br CH₃ Br (2-) NO₂ SCH₃ CH₃ Br (2-) NO₂ OCH₃ CH₃ Br (2-) NO₂ N(CH₃)₂ CH₃ Br (2-) NO₂ CF₃ CH₃ Br (2-) CF₃ Br CH₃ Br (2-) CF₃ SCH₃ CH₃ Br (2-) CF₃ OCH₃ CH₃ Br (2-) CF₃ N(CH₃)₂ CH₃ Br (2-) CF₃ CF₃ CH₃ Br (2-) SO₂CH₃ Br CH₃ Br (2-) SO₂CH₃ SCH₃ CH₃ Br (2-) SO₂CH₃ OCH₃ CH₃ Br (2-) SO₂CH₃ N(CH₃)₂ CH₃ Br (2-) SO₂CH₃ CF₃ CH₃ Br (2-) CH₃ Br CH₃ Br (2-) CH₃ SCH₃ CH₃ Br (2-) CH₃ OCH₃ CH₃ Br (2-) CH₃ N(CH₃)₂ CH₃ Br (2-) CH₃ CF₃ CH₃ Cl (2-) OCH₃ CF₃ CH₃ Cl (2-) OCH₃ SCH₃ CH₃ Cl (2-) OCH₃ SC₂H₅ CH₃ Cl (2-) OCH₃ SC₃H₇ CH₃ Cl (2-) OCH₃ SC₃H₇-i CH₃ Cl (2-) OCH₃ CH₃ Cl (2-) OCH₃ CH₃ Cl (2-) OCH₃ CH₃ Cl (2-) OCH₃ CH₃ Cl (2-) OCH₃ CH₃ Cl (2-) OCH₃ SCH═C═CH₂ CH₃ Cl (2-) OCH₃ SCH₂CN CH₃ Cl (2-) OCH₃ SCH₂CH₂CN CH₃ Cl (2-) OCH₃ OCH₃ CH₃ Cl (2-) OCH₃ OC₂H₅ CH₃ Cl (2-) OCH₃ OC₃H₇ CH₃ Cl (2-) OCH₃ OC₃H₇-i CH₃ Cl (2-) OCH₃ OC₄H₉ CH₃ Cl (2-) OCH₃ OCH₂CF₃ CH₃ Cl (2-) OCH₃ CH₃ Cl (2-) OCH₃ OC₆H₅ CH₃ Cl (2-) OCH₃ H CH₃ Cl (2-) OCH₃ CH₃ CH₃ Cl (2-) OCH₃ C₂H₅ CH₃ Cl (2-) OCH₃ C₃H₇ CH₃ Cl (2-) OCH₃ C₃H₇-i CH₃ Cl (2-) OCH₃ C₄H₉ CH₃ Cl (2-) OCH₃ C₄H₉-i CH₃ Cl (2-) OCH₃ C₄H₉-s CH₃ Cl (2-) OCH₃ C₄H₉-t CH₃ Cl (2-) OCH₃ CH₃ Cl (2-) OCH₃ CH₃ Cl (2-) OCH₃ CH═CHCH₃ CH₃ Cl (2-) OCH₃ CH₃ Cl (2-) OCH₃ CH₃ Cl (2-) OCH₃ CH₃ Cl (2-) OCH₃ N(CH₃)₂ CH₃ Cl (2-) OCH₃ CH₃ Cl (2-) OCH₃ Cl CH₃ Cl (2-) OCH₃ Br CH₃ SO₂CH₃ (2-) OCH₃ CF₃ CH₃ SO₂CH₃ (2-) OCH₃ SCH₃ CH₃ SO₂CH₃ (2-) OCH₃ SC₂H₅ CH₃ SO₂CH₃ (2-) OCH₃ SC₃H₇ CH₃ SO₂CH₃ (2-) OCH₃ SC₃H₇-i CH₃ SO₂CH₃ (2-) OCH₃ CH₃ SO₂CH₃ (2-) OCH₃ CH₃ SO₂CH₃ (2-) OCH₃ CH₃ SO₂CH₃ (2-) OCH₃ CH₃ SO₂CH₃ (2-) OCH₃ CH₃ SO₂CH₃ (2-) OCH₃ SCH═C═CH₂ CH₃ SO₂CH₃ (2-) OCH₃ SCH₂CN CH₃ SO₂CH₃ (2-) OCH₃ SCH₂CH₂CN CH₃ SO₂CH₃ (2-) OCH₃ OCH₃ CH₃ SO₂CH₃ (2-) OCH₃ OC₂H₅ CH₃ SO₂CH₃ (2-) OCH₃ OC₃H₇ CH₃ SO₂CH₃ (2-) OCH₃ OC₃H₇-i CH₃ SO₂CH₃ (2-) OCH₃ OC₄H₉ CH₃ SO₂CH₃ (2-) OCH₃ OCH₂CF₃ CH₃ SO₂CH₃ (2-) OCH₃ CH₃ SO₂CH₃ (2-) OCH₃ OC₆H₅ CH₃ SO₂CH₃ (2-) OCH₃ H CH₃ SO₂CH₃ (2-) OCH₃ CH₃ CH₃ SO₂CH₃ (2-) OCH₃ C₂H₅ CH₃ SO₂CH₃ (2-) OCH₃ C₃H₇ CH₃ SO₂CH₃ (2-) OCH₃ C₃H₇-i CH₃ SO₂CH₃ (2-) OCH₃ C₄H₉ CH₃ SO₂CH₃ (2-) OCH₃ C₄H₉-i CH₃ SO₂CH₃ (2-) OCH₃ C₄H₉-s CH₃ SO₂CH₃ (2-) OCH₃ C₄H₉-t CH₃ SO₂CH₃ (2-) OCH₃ CH₃ SO₂CH₃ (2-) OCH₃ CH₃ SO₂CH₃ (2-) OCH₃ CH═CHCH₃ CH₃ SO₂CH₃ (2-) OCH₃ CH₃ SO₂CH₃ (2-) OCH₃ CH₃ SO₂CH₃ (2-) OCH₃ CH₃ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ CH₃ SO₂CH₃ (2-) OCH₃ CH₃ SO₂CH₃ (2-) OCH₃ Cl CH₃ SO₂CH₃ (2-) OCH₃ Br CH₃ Cl (2-) OCH₃ CF₃ Cl (2-) OCH₃ SCH₃ Cl (2-) OCH₃ SC₂H₅ Cl (2-) OCH₃ SC₃H₇ Cl (2-) OCH₃ SC₃H₇-i Cl (2-) OCH₃ Cl (2-) OCH₃ Cl (2-) OCH₃ Cl (2-) OCH₃ Cl (2-) OCH₃ Cl (2-) OCH₃ SCH═C═CH₂ Cl (2-) OCH₃ SCH₂CN Cl (2-) OCH₃ SCH₂CH₂CN Cl (2-) OCH₃ OCH₃ Cl (2-) OCH₃ OC₂H₅ Cl (2-) OCH₃ OC₃H₇ Cl (2-) OCH₃ OC₃H₇-i Cl (2-) OCH₃ OC₄H₉ Cl (2-) OCH₃ OCH₂CF₃ Cl (2-) OCH₃ Cl (2-) OCH₃ OC₆H₅ Cl (2-) OCH₃ H Cl (2-) OCH₃ CH₃ Cl (2-) OCH₃ C₂H₅ Cl (2-) OCH₃ C₃H₇ Cl (2-) OCH₃ C₃H₇-i Cl (2-) OCH₃ C₄H₉ Cl (2-) OCH₃ C₄H₉-i Cl (2-) OCH₃ C₄H₉-s Cl (2-) OCH₃ C₄H₉-t Cl (2-) OCH₃ Cl (2-) OCH₃ Cl (2-) OCH₃ CH═CHCH₃ Cl (2-) OCH₃ Cl (2-) OCH₃ Cl (2-) OCH₃ Cl (2-) OCH₃ N(CH₃)₂ Cl (2-) OCH₃ Cl (2-) OCH₃ Cl Cl (2-) OCH₃ Br SO₂CH₃ (2-) OCH₃ CF₃ SO₂CH₃ (2-) OCH₃ SCH₃ SO₂CH₃ (2-) OCH₃ SC₂H₅ SO₂CH₃ (2-) OCH₃ SC3H₇ SO₂CH₃ (2-) OCH₃ SC₃H₇-i SO₂CH₃ (2-) OCH₃ SO₂CH₃ (2-) OCH₃ SO₂CH₃ (2-) OCH₃ SO₂CH₃ (2-) OCH₃ SO₂CH₃ (2-) OCH₃ SO₂CH₃ (2-) OCH₃ SCH═C═CH₂ SO₂CH₃ (2-) OCH₃ SCH₂CN SO₂CH₃ (2-) OCH₃ SCH₂CH₂CN SO₂CH₃ (2-) OCH₃ OCH₃ SO₂CH₃ (2-) OCH₃ OC₂H₅ SO₂CH₃ (2-) OCH₃ OC₃H₇ SO₂CH₃ (2-) OCH₃ OC₃H₇-i SO₂CH₃ (2-) OCH₃ OC₄H₉ SO₂CH₃ (2-) OCH₃ OCH₂CF₃ SO₂CH₃ (2-) OCH₃ SO₂CH₃ (2-) OCH₃ OC₆H₅ SO₂CH₃ (2-) OCH₃ H SO₂CH₃ (2-) OCH₃ CH₃ SO₂CH₃ (2-) OCH₃ C₂H₅ SO₂CH₃ (2-) OCH₃ C₃H₇ SO₂CH₃ (2-) OCH₃ C₃H₇-i SO₂CH₃ (2-) OCH₃ C₄H₉ SO₂CH₃ (2-) OCH₃ C₄H₉-i SO₂CH₃ (2-) OCH₃ C₄H₉-s SO₂CH₃ (2-) OCH₃ C₄H₉-t SO₂CH₃ (2-) OCH₃ SO₂CH₃ (2-) OCH₃ SO₂CH₃ (2-) OCH₃ CH═CHCH₃ SO₂CH₃ (2-) OCH₃ SO₂CH₃ (2-) OCH₃ SO₂CH₃ (2-) OCH₃ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ SO₂CH₃ (2-) OCH₃ Cl SO₂CH₃ (2-) OCH₃ Br Cl (2-) OCH₃ CF₃ N(CH₃)₂ Cl (2-) OCH₃ SCH₃ N(CH₃)₂ Cl (2-) OCH₃ SC₂H₅ N(CH₃)₂ Cl (2-) OCH₃ SC₃H₇ N(CH₃)₂ Cl (2-) OCH₃ SC₃H₇-i N(CH₃)₂ Cl (2-) OCH₃ N(CH₃)₂ Cl (2-) OCH₃ N(CH₃)₂ Cl (2-) OCH₃ N(CH₃)₂ Cl (2-) OCH₃ N(CH₃)₂ Cl (2-) OCH₃ N(CH₃)₂ Cl (2-) OCH₃ SCH═C═CH₂ N(CH₃)₂ Cl (2-) OCH₃ SCH₂CN N(CH₃)₂ Cl (2-) OCH₃ SCH₂CH₂CN N(CH₃)₂ Cl (2-) OCH₃ OCH₃ N(CH₃)₂ Cl (2-) OCH₃ OC₂H₅ N(CH₃)₂ Cl (2-) OCH₃ OC₃H₇ N(CH₃)₂ Cl (2-) OCH₃ OC₃H₇-i N(CH₃)₂ Cl (2-) OCH₃ OC₄H₉ N(CH₃)₂ Cl (2-) OCH₃ OCH₂CF₃ N(CH₃)₂ Cl (2-) OCH₃ N(CH₃)₂ Cl (2-) OCH₃ OC₆H₅ N(CH₃)₂ Cl (2-) OCH₃ H N(CH₃)₂ Cl (2-) OCH₃ CH₃ N(CH₃)₂ Cl (2-) OCH₃ C₂H₅ N(CH₃)₂ Cl (2-) OCH₃ C₃H₇ N(CH₃)₂ Cl (2-) OCH₃ C₃H₇-i N(CH₃)₂ Cl (2-) OCH₃ C₄H₉ N(CH₃)₂ Cl (2-) OCH₃ C₄H₉-i N(CH₃)₂ Cl (2-) OCH₃ C₄H₉-s N(CH₃)₂ Cl (2-) OCH₃ C₄H₉-t N(CH₃)₂ Cl (2-) OCH₃ N(CH₃)₂ Cl (2-) OCH₃ N(CH₃)₂ Cl (2-) OCH₃ CH═CHCH₃ N(CH₃)₂ Cl (2-) OCH₃ N(CH₃)₂ Cl (2-) OCH₃ N(CH₃)₂ Cl (2-) OCH₃ N(CH₃)₂ Cl (2-) OCH₃ N(CH₃)₂ N(CH₃)₂ Cl (2-) OCH₃ N(CH₃)₂ Cl (2-) OCH₃ Cl N(CH₃)₂ Cl (2-) OCH₃ Br N(CH₃)₂ SO₂CH₃ (2-) OCH₃ CF₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ SCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ SC₂H₅ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ SC₃H₇ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ SC₃H₇-i N(CH₃)₂ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ SCH═C═CH₂ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ SCH₂CN N(CH₃)₂ SO₂CH₃ (2-) OCH₃ SCH₂CH₂CN N(CH₃)₂ SO₂CH₃ (2-) OCH₃ OCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ OC₂H₅ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ OC₃H₇ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ OC₃H₇-i N(CH₃)₂ SO₂CH₃ (2-) OCH₃ OC₄H₉ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ OCH₂CF₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ OC₆H₅ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ H N(CH₃)₂ SO₂CH₃ (2-) OCH₃ CH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ C₂H₅ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ C₃H₇ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ C₃H₇-i N(CH₃)₂ SO₂CH₃ (2-) OCH₃ C₄H₉ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ C₄H₉-i N(CH₃)₂ SO₂CH₃ (2-) OCH₃ C₄H₉-s N(CH₃)₂ SO₂CH₃ (2-) OCH₃ C₄H₉-t N(CH₃)₂ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ CH═CHCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ N(CH₃)₂ SO₂CH₃ (2-) OCH₃ Cl N(CH₃)₂ SO₂CH₃ (2-) OCH₃ Br N(CH₃)₂ Cl (2-) OCH₃ CH₃ OCH₃ Cl (2-) OCH₃ C₂H₅ OCH₃ Cl (2-) OCH₃ C₃H₇ OCH₃ Cl (2-) OCH₃ SCH₃ OCH₃ Cl (2-) OCH₃ SC₂H₅ OCH₃ Cl (2-) OCH₃ OCH₃ OCH₃ Cl (2-) OCH₃ OC₂H₅ OCH₃ Cl (2-) OCH₃ CH₃ OC₂H₅ Cl (2-) OCH₃ C₂H₅ OC₂H₅ Cl (2-) OCH₃ C₃H₇ OC₂H₅ Cl (2-) OCH₃ SCH₃ OC₂H₅ Cl (2-) OCH₃ SC₂H₅ OC₂H₅ Cl (2-) OCH₃ OCH₃ OC₂H₅ Cl (2-) OCH₃ OC₂H₅ OC₂H₅ SO₂CH₃ (2-) OCH₃ Cl OCH₃ SO₂CH₃ (2-) OCH₃ Br OCH₃ SO₂CH₃ (2-) OCH₃ CH₃ OCH₃ SO₂CH₃ (2-) OCH₃ C₂H₅ OCH₃ SO₂CH₃ (2-) OCH₃ C₃H₇ OCH₃ SO₂CH₃ (2-) OCH₃ SCH₃ OCH₃ SO₂CH₃ (2-) OCH₃ SC₂H₅ OCH₃ SO₂CH₃ (2-) OCH₃ OCH₃ OC₂H₅ SO₂CH₃ (2-) OCH₃ OC₂H₅ OC₂H₅ SO₂CH₃ (2-) OCH₃ CH₃ OC₂H₅ SO₂CH₃ (2-) OCH₃ C₂H₅ OC₂H₅ SO₂CH₃ (2-) OCH₃ C₃H₇ OC₂H₅ SO₂CH₃ (2-) OCH₃ SCH₃ OC₂H₅ SO₂CH₃ (2-) OCH₃ SC₂H₅ OC₂H₅ SO₂CH₃ (2-) OCH₃ OCH₃ OC₂H₅

Group 10

Here, R³, (R⁴)_n, R⁵and R⁶have, for example, the meanings given for Group 9.
Group 11

Here, R³, (R⁴)_n, R⁵and R⁶have, for example, the meanings given for Group 9.
Group 12

Here, R³, (R⁴)_n, R⁵and R⁶have, for example, the meanings given for Group 9, and m represents the number 0, 1 or 2.
Group 13

Here, R³, (R⁴)_n, R⁵and R⁶have, for example, the meanings given for Group 9.
Group 14

Here, R³, (R⁴)_n, R⁵and R⁶have, for example, the meanings given for Group 9.
Group 15

Here, R³, (R⁴)_n, R⁵and R⁶have, for example, the meanings given for Group 9.
Group 16

Here, R³, (R⁴)_n, R⁵and R⁶have, for example, the meanings given for Group 9, and m represents the number 0, 1 or 2.

The novel substituted benzoylisoxazoles of the general formula (I) have strong and selective herbicidal activity.

The novel substituted benzoylisoxazoles of the general formula (I) are obtained when

- (a) benzoylisoxazoles of the general formula (II)
  in which
- n, A, R¹, R², R³and R⁴are each as defined above and
- X represents halogen
- are reacted with heterocycles of the general formula (III)
  H-Z (III)
  in which
- Z is as defined above,
- if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
- or when
- if R²is hydrogen
- (b) benzoyl ketones of the general formula (IV)
  in which
- n, A, R¹, R³, R⁴and Z are each as defined above
- are reacted with a trialkyl orthoformate or an N,N-dimethylformamide dialkyl acetal and subsequently with hydroxylamine or an acid adduct thereof,
- if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
- or when
- if R²represents optionally substituted alkoxycarbonyl
- (c) benzoyl ketones of the general formula (IV)
  in which
- n, A, R¹, R³, R⁴and Z are each as defined above are reacted with an alkyl cyanoformate and then with hydroxylamine or an acid adduct thereof, or with an alkyl chloro-hydroximino-acetate, if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
- or when
- if R²represents alkylthio
- (d) benzoyl ketones of the general formula (IV)
  in which
- n, A, R¹, R³, R⁴and Z are each as defined above
- are reacted with carbon disulphide and with an alkylating agent and then with hydroxylamine or an acid adduct thereof,
- if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
- and electrophilic or nucleophilic substitutions and/or oxidations or reductions within the scope of the definition of the substituents are, if appropriate, subsequently carried out in a customary manner on the compounds of the formula (I) obtained according to processes (a) to (d).

The compounds of the formula (I) can be converted by customary methods into other compounds of the formula (I) according to the above definition, for example by nucleophilic substitution (for example R⁵:Cl→OC₂H₅, SCH₃) or by oxidation (for example R⁵:CH₂SCH₃→CH₂S(O)CH₃).

In the preparation of compounds of the general formula (I), it is also possible that compounds of the general formula (IE)
in which

- n, A, R¹, R², R³, R⁴and Z are each as defined above
- are formed in certain amounts.

The compounds of the general formula (IE) also form, as novel substances, part of the subject-matter of the present application.

Using, for example, (3-chloromethyl-4-trifluoromethyl-phenyl)-(3,5-dimethyl-iso-xazol-4-yl)-methanone and 4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of the reaction in the process (a) according to the invention can be illustrated by the following formula scheme:

Using, for example, 1-[2-chloro-3-(3,4-dimethyl-5-oxo-4,5-dihydro-[1,2,4-triazol-1-yl-methyl)-phenyl]-pentane-1,3-dione, N,N-dimethyl-formamide diethyl acetal and hydroxylamine as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following formula scheme:

Using, for example, 1-[2-chloro-3-(4-ethoxy-3-ethyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl-methyl)-phenyl]-3-cyclopropyl-propane1,3-dione, ethyl cyanoformate and hydroxylamine as starting materials, the course of the reaction in the process (c) according to the invention can be illustrated by the following formula scheme:

Using, for example, 1-[2-chloro-3-(4-methyl-3-methylthio-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl-methyl)-phenyl]-3-cyclopropyl-propane-1,3-dione, carbon disulphide, methyl bromide and hydroxylamine as starting materials, the course of the reaction in the process (d) according to the invention can be illustrated by the following formula scheme:

The formula (II) provides a general definition of the benzoylisoxazoles to be used as starting materials in the process (a) according to the invention for preparing compounds of the general formula (I). In the general formula (II), n, A, R¹, R², R³and R⁴each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for n, A, R¹, R², R³and R⁴; X preferably represents fluorine, chlorine, bromine or iodine, in particular chlorine or bromine.

Except for ethyl 4-(2-bromo-methyl-benzoyl)-5-cyclopropyl-isoxazole-3-carboxylate (cf WO-A-95/31446), the starting materials of the general formula (II) have hitherto not been disclosed in the literature; except for ethyl 4-(2-bromomethyl-benzoyl)-5-cyclopropyl-isoxazole-3-carboxylate, they also form, as novel substances, part of the subject-matter of the present application.

The novel benzoylisoxazoles of the general formula (II) are obtained when benzoylisoxazoles of the general formula (V)
in which

- n, A, R¹, R², R³and R⁴are each as defined above
- are reacted with a side-chain halogenating agent, such as, for example, N-bromo-succinimide or N-chloro-succinimide, under UV light or in the presence of a reaction auxiliary, such as, for example, 2,2′-azo-bis-isobutyonitrile, in the presence of a diluent, such as, for example, carbon tetrachloride, at temperatures between 0° C. and 100° C. (cf. WO-A-95/31446; Preparation Examples).

The intermediates of the general formula (V) are known and/or can be prepared by processes known per se (cf. WO-A-95/31446; Preparation Examples).

The formula (III) provides a general definition of the heterocycles further to be used as starting materials in the process (a) according to the invention for preparing compounds of the general formula (I). In the general formula (III), Z preferably has that meaning which has already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred for Z.

The starting materials of the general formula (III) are known and/or can be prepared by processes known per se.

The formula (IV) provides a general defintion of the benzoyl ketones to be used as starting materials in the processes (b), (c) and (d) according to the invention for preparing compounds of the general formula (I). In the general formula (IV), n, A, R¹, R³, R⁴and Z each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for n, A, R¹, R³, R⁴and Z.

The starting materials of the general formula (IV) have hitherto not been disclosed in the literature; they also, as novel substances, form part of the subject-matter of the present application.

The novel benzoyl ketones of the general formula (IV) are obtained when ketones of the general formula (VI)
in which

- R¹is as defined above,
- are reacted with benzoic acid derivatives of the general formula (VII)
  in which
- n, A, R³, R⁴and Z are each as defined above, and
- Y represents halogen (in particular fluorine, chlorine or bromine) or represents optionally substituted alkoxy (in particular methoxy, ethoxy or ethoxyethoxy),
- if appropriate in the presence of a reaction auxiliary, such as, for example, sodium hydride, and if appropriate in the presence of a diluent, such as, for example, tetra-hydrofuran, at temperatures between 0° C. and 100° C. (cf. the Preparation Examples).

The benzoic acid derivatives of the general formula (VII) required as intermediates are known and/or can be prepared by processes known per se (cf. DE-A-38 39 480, DE-A-42 39 296, EP-A-597 360, EP-A-609 734, DE-A-43 03 676, EP-A-617 026, DE-A-44 05 614, U.S. Pat. No. 5,378,681).

The benzoic acid derivatives of the general formula (VII) are obtained when halogeno(alkyl)benzoic acid derivatives of the general formula (VIII)
in which

- n, A, R³and R⁴are each as defined above and
- X represents halogen (in particular fluorine, chlorine or bromine) and
- Y¹represents optionally substituted alkoxy (in particular methoxy, ethoxy or ethoxyethoxy),
- are reacted with compounds of the general formula (III),
  H-Z (III)
  in which
- Z is as defined above,
- if appropriate in the presence of a reaction auxiliary, such as, for example, sodium hydride, triethylamine or potassium carbonate, and if appropriate in the presence of a diluent, such as, for example, acetone, acetonitrile, N,N-dimethylformamide or N,N-dimethyl-acetamide, at temperatures between 50° C. and 200° C. (cf. the Preparation Examples).

The halogeno(alkyl)benzoic acid derivatives of the formula (VIII) required as intermediates are known and/or can be prepared by processes known per se (cf. EP-A-90 369, EP-A-93 488, EP-A-399 732, EP-A-480 641, EP-A-609 798, EP-A-763 524, DE-A-21 26 720, WO-A-93/03722, WO-A-97/38977, U.S. Pat. No. 3,978,127, U.S. Pat. No. 4,837,333).

The process (b) according to the invention for preparing the compounds of the formula (I) is carried out using orthoformic esters or N,N-dimethylformamide acetals. These compounds preferably contain alkyl groups having 1 to 4 carbon atoms, in particular methyl or ethyl. Examples which may be mentioned are trimethyl orthoformate, triethyl orthoformate, N,N-dimethyl-formamide dimethyl acetal and N,N-dimethyl-formamide diethyl acetal.

The process (c) according to the invention for preparing the compounds of the formula (I) is carried out using alkyl cyanoformates or alkyl chloro-hydroximino-acetates. These compounds preferably contain alkyl groups having 1 to 4 carbon atoms, in particular methyl or ethyl. Examples which may be mentioned are methyl cyanoformate, ethyl cyanoformate, methyl chloro-hydroximino-acetate and ethyl chloro-hydroximino-acetate.

The process (d) according to the invention for preparing the compounds of the formula (I) is carried out using (carbon disulphide and) alkylating agents. These compounds preferably contain alkyl groups having 1 to 4 carbon atoms, in particular methyl or ethyl. Examples which may be mentioned are methyl chloride, methyl bromide, methyl iodide, dimethyl sulphate, ethyl chloride, ethyl bromide, ethyl iodine and diethyl sulphate.

The processes (b), (c) and—if appropriate—(d) according to the invention for preparing the compounds of the formula (I) are carried out using hydroxylamine or an acid adduct thereof. A preferred acid adduct which may be mentioned is hydroxylamine hydrochloride.

The processes according to the invention for preparing the compounds of the general formula (I) are preferably carried out using diluents. Suitable diluents for carrying out the processes (a), (b), (c) and (d) according to the invention are, in addition to water, especially inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate, sulphoxides, such as dimethyl sulphoxide, alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water or pure water.

Suitable reaction auxiliaries for the processes (a), (b), (c) and (d) according to the invention are, in general, the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, such as, for example, sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hyride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or -t-butoxide or potassium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine tributylaamine ethyl-diisopropylamine N,N-dimethyl-cyclohexylamine, dicyclohexylamine ethyl-dicyclohexylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethylpyridine, 5-ethyl-2-methyl-pyridine, 4-di-methylamino-pyridine, N-methylpiperidine, 1,4-diazabicyclo[2.2.2]-octane (DABCO), 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).

When carrying out the processes (a), (b), (c) and (d) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the processes are carried out at temperatures between 0° C. and 150° C., preferably between 10° C. and 120° C.

The processes according to the invention are generally carried out under atmospheric pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure—in general between 0.1 bar and 10 bar.

For carrying out the processes according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible for one of the components to be used in a relatively large excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for several hours. Work-up is carried out by customary methods (cf. the Preparation Examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed killers. By weeds in the broadest sense there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in connection with the following plants:

- Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
- Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoca, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
- Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
- Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.

However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.

Depending on the concentration, the compounds according to the invention are suitable for total weed control, for example on industrial terrain and rail tracks and on paths and areas with or without tree growth. Equally, the compounds according to the invention can be employed for controlling weeds in perennial crops, for example forests, ornamental tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns and turf and pastures and for selective weed control in annual crops.

The compounds of the formula (I) according to the invention have strong herbicidal activity and a broad activity spectrum when used on the soil and on above-ground parts of plants. To a certain extent they are also suitable for selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both by the pre-emergence and by the post-emergence method.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic substances impregnated with active compound, and microencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is to say liquid solvents and/or solid carriers, optionally with the use of surfactants, that is to say emulsifiers and/or dispersants and/or foam formers.

If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Liquid solvents which are mainly suitable are: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl-formamide and dimethyl sulphoxide, and water.

Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic meals, and granules of organic material, such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, aryl-sulphonates and protein hydrolysates; suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.

Tackifiers, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils.

It is possible to use dyestuffs, such as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.

Possible components for the mixtures are known herbicides, for example acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl), benfuresate, bensulfuron(-methyl), bentazone, benzobicyclon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac-(-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl), chlomethoxy-fen, chloramben, chloridazon, chlorimuron(-ethyl), chlornitrofen, chlorosulfuron, chlorotoluron, cinidon(-ethyl), cinmethylin, cinosulfuron, clethodim, clodinafop-(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, di-methenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-(-P-ethyl), flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl), flazasulffiron, fluazifop(-P-butyl), fluazolate, flucarbazone, flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam, flupropacil, flurpyrsulfuron-(-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr(-meptyl), flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen, glufosinate(-animonium), glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl), haloxyfop-(-P-methyl), hexazinone, imazamethabenz-(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron(-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron, meto-bromuron, (alpha-)metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxazi-clomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone, phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron(-methyl), procarbazone, prometryn, propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate, pyrazo-sulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac-(-methyl), pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb, tio-carbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin, triflusulfuron and tritosulfuron.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering.

The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a relatively wide range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and the use of the active compounds according to the invention can be seen from the examples below.

PREPARATION EXAMPLES Example 1

(Process (a))

At room temperature (about 20° C.), a solution of 1.20 g (33% pure, i.e. 2.8 mMol) of methyl 4-(3-bromomethyl-5-trifluoromethyl-benzoyl)-5-cyclopropyl-isoxazole-3-carboxylate in 10 ml of N,N-dimethyl-formamide is added dropwise with stirring to a mixture of 0.44 g (2.8 mMol) of 4-ethoxy-5-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 84 mg (2.8 mMol) of sodium hydride (75% pure) and 20 ml of N,N-dimethyl-formamide, and the reaction mixture is stirred at room temperature for 30 minutes. The mixture is then diluted with saturated aqueous sodium chloride solution to about twice its original volume and extracted twice with ethyl acetate. The combined organic extract solutions are dried with sodium sulphate and filtered. The filtrate is concentrated under water pump vacuum and the residue is purified by column chromatography (silica gel, hexane/ethyl acetate, vol.: 7/3).

This gives 0.45 g (96% of theory based on 33% pure starting material) of (5-cyclo-propyl-3-methoxycarbonyl-isoxazol-4-yl)-[2-(4-ethoxy-3-ethyl-5-oxo-4,5-dihydro-[1,2,4]-triazol-1-yl-methyl)-4-trifluoromethyl-phenyl]-methanone as an amorphous product.

logP (determined at pH=2.3): 3.56.

Example 2

(process (b))

A mixture of 1.5 g (36 mMol) of 1-cyclopropyl-3-[2-(4-methyl-3-methylthio-5-oxo-4,5-dihydro-[1,2,4]-triazol-1-yl-methyl)4trifluoromethyl-phenyl]-propane-1,3-dione, 0.56 g (46 mMol) of N,N-dimethyl-formamide dimethyl acetal and 15 ml of toluene is stirred at 90° C. for 60 minutes. The mixture is then concentrated under water pump vacuum, the residue is taken up in 15 ml of ethanol and the mixture is, after addition of 0.25 g (36 mMol) of hydroxylamine hydrochloride, stirred at room temperature (about. 20° C.) for two hours. The mixture is concentrated under water pump vacuum, the residue is shaken with methylene chloride/water and the organic phase is separated off, washed with saturated aqueous sodium chloride solution, dried with sodium sulphate and filtered. The filtrate is concentrated under water pump vacuum and the residue is purified by column chromatography (silica gel, ethyl acetate/hexane, vol: 1/1).

This gives 0.20 g (13% of theory) of (5-cyclopropyl-isoxazol-4-yl)-[2-(4-methyl-3-methylthio-5-oxo-4,5-dihydro-[1,2,4]-triazol-1-yl-methyl)-4-trifluoromethyl-phenyl]-methanone as an amorphous product.

logP (determined at pH=2.3): 2.94.

Analogously to Examples 1 and 2, and in accordance with the general description of the preparation process according to the invention, it is also possible to prepare, for example, the compounds of the general formula (I)—or of the formulae (IA), (IB), (IC) or (ID)—listed in Tables 1 and 1a below.

TABLE 1a Examples of the compounds of the formula (I) or (ID) Ex.- (position) (position) (position) No. R¹ R² R³ (R⁴)_n -A-Z physical data ID-1 H (2) Cl (4) Cl logP = 2.48^a) ID-2 H (2) OCH₃ (4) Cl logP = 2.46^a) ID-3 H (2) Cl (4) ID-4 H (2) OCH₃ (4) Cl ID-5 H (2) Cl (4) Cl ID-6 H (2) Cl (4) Cl ID-7 H (2) Cl (4) Cl ID-8 H (2) Cl (4) Cl ID-9 H (2) Cl (4) Cl ID-10 H (2) OCH₃ (4) Cl ID-11 H (2) Cl (4) SO₂CH₃ ID-12 H (2) Cl (4) SO₂CH₃ ID-13 H (2) SO₂CH₃ (4) Cl ID-14 H (2) SO₂CH₃ (4) Cl ID-15 H (2) Cl (4) CF₃ ID-16 H (2) Cl (4) CF₃ ID-17 H (2) NO₂ (4) CF₃ ID-18 H (2) NO₂ (4) CF₃ ID-19 H (2) OCH₃ (4) CF₃ ID-20 H (2) OCH₃ (4) CF₃ ID-21 H (2) Cl (4) CN ID-22 H (2) Cl (4) CN ID-23 H (2) OCH₃ (4) CN ID-24 H (2) OCH₃ (4) CN ID-25 H (2) Cl (4) F ID-26 H (2) Cl (4) F ID-27 H H — ID-28 H H — ID-29 H (4) F — ID-30 H (4) F — ID-31 H (4) Cl — ID-32 H (4) Cl — ID-33 H (4) F — ID-34 H (4) Cl — ID-35 H (4) Br — ID-36 H (4) I — ID-37 H (4) NO₂ — ID-38 H (4) CN — ID-39 H (4) CF₃ — ID-40 H (4) SO₂CH₃ — ID-41 H (4) OCH₃ — ID-42 H (4) OCF₃ — ID-43 H (4) OCHF₂ — ID-44 H (4) SCH₃ — ID-45 H (4) SOCH₃ — ID-46 (2) Cl (4) Cl ID-47 (2) OCH₃ (4) Cl ID-48 (2) Cl (4) Cl ID-49 (2) OCH₃ (4) Cl ID-50 SCH₃ (2) Cl (4) Cl ID-51 SCH₃ (2) OCH₃ (4) Cl ID-52 SCH₃ (2) Cl (4) Cl ID-53 SCH₃ (2) OCH₃ (4) Cl ID-54 H (2) Cl (4) Cl ID-55 H (2) OCH₃ (4) Cl ID-56 H (2) Cl (4) Cl ID-57 H (2) OCH₃ (4) Cl ID-58 H (4) CF₃ — ID-59 H (4) CF₃ — ID-60 H (4) CF₃ — ID-61 H (2) Cl (4) Cl ID-62 H (2) OCH₃ (4) Cl ID-63 H (2) Cl (4) Cl ID-64 H (2) OCH₃ (4) Cl ID-65 H (2) Cl (4) Cl ID-66 H (2) OCH₃ (4) Cl ID-67 H (2) NO₂ (4) SO₂CH₃ ID-68 H (2) NO₂ (4) SO₂CH₃ ID-69 H (2) Cl (4) SO₂CH₃ ID-70 H (2) NO₂ (4) SO₂CH₃ ID-71 H (2) NO₂ (4) CF₃ ID-72 H (2) NO₂ (4) CF₃ ID-73 H (2) NO₂ (4) CF₃ ID-74 H (2) Cl (4) SO₂CH₃ ID-75 H (2) NO₂ (4) SO₂CH₃ ID-76 H (2) NO₂ (4) CF₃ ID-77 H (2) Cl (4) SO₂CH₃ ID-78 H (2) NO₂ (4) SO₂CH₃ ID-79 H (2) NO₂ (4) CF₃

The logP values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using a reverse-phase column (C 18). Temperature: 43° C.

(a) Mobile phases for the determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile—the corresponding data in Table 1 are labelled ^a).

(b) Mobile phases for the determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile—the corresponding data in Table 1 are labelled ^b).

Calibration was carried out using unbranched alkan-2-ones (with from 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by the retention times using linear interpolation between two successive alkanones).

The lambda-max values were determined in the maxima of the chromatographic signals, using the UV spectra from 200 nm to 400 nm.

Starting Materials of the Formula (II)

Example (II-1)

A mixture of 3.0 g (8.5 Mol) of methyl 5-cyclopropyl-4-(2-methyl-4-trifluoro-methyl-benzoyl)-isoxazole-4-carboxylate, 1.5 g (8.5 mMol) of N-bromo-succinimide, 0.15 g of 2,2′-azo-bis-isobutyronitrile and 45 ml of carbon tetrachloride is heated under reflux for two hours and, after cooling, filtered. The filtrate is diluted with methylene chloride to about twice its original volume, washed with 20% strength aqueous sodium hydrogen sulphite solution, dried with sodium sulphate and filtered. From the filtrate, the solvent is carefully distilled off under water pump vacuum.

This gives 2.5 g (68% of theory) of methyl 5-cyclopropyl-4-(2-bromomethyl-4-trifluoromethyl-benzoyl)-isoxazole-4-carboxylate as an amorphous product which can be reacted further without any purification.

Analogously to Example (II-1), it is also possible to prepare, for example, the compounds of the formula (II) listed in Table 2 below.

TABLE 2 (II) Examples of the compounds of the formula (II) Ex.- (position) (position) physical No. R¹ R² (position) R³ (R⁴)_n A—X data II-2 (4) Br — (2) CH₂Br II-3 (4) Cl — (2) CH₂Br II-4 (4) CH₃ — (2) CH₂Br II-5 (4) CN — (2) CH₂Br II-6 (4) OCH₃ — (2) CH₂Br II-7 (4) SCH₃ — (2) CH₂Br II-8 (4) SO₂CH₃ — (2) CH₂Br II-9 (4) SO₂N(CH₃)₂ — (2) CH₂Br II-10 SCH₃ (4) CF₃ — (2) CH₂Br II-11 (4) OCHF₂ — (2) CH₂Br II-12 (4) OCF₃ — (2) CH₂Br II-13 (4) NO₂ — (2) CH₂Br II-14 (4) Cl (2) Cl (3) CH₂Br II-15 H (4) Cl (2) Cl (3) CH₂Br II-16 (4) Cl (2) Cl (3) CH₂Br II-17 H — (3) CH₂Br II-18 H H — (3) CH₂Br II-19 H (4) Cl (2) OCH₃ (3) CH₂Br II-20 H (4) CH₃ (3) OCH₃ (2) CH₂Br II-21 H (4) CN (3) OCH₃ (2) CH₂Br II-22 H (4) SO₂CH₃ (3) CH₂OCH₃ (2) CH₂Br II-23 H (4) CF₃ (3) CH₂OCH₃ (2) CH₂Br II-24 H (4) F (2) Cl (3) CH₂Br

Starting Materials of the Formula (IV)

Example (IV-1)

A mixture of 0.94 g (11 mMol) of cyclopropyl methyl ketone, 0.35 g (11 mMol) of sodium hydride (75% pure) and 15 ml of tetrahydrofiran is stirred at 20° C. for 30 minutes. A solution of 2.0 g (5.5 mMol) of 4-methyl-5-methylthio-2-(2-methoxy-carbonyl-5-trifluoromethyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one in 8 ml of tetrahydrofuran is then added dropwise and, after addition of 0.2 g of dibenzo-18-crone-6, the reaction mixture is heated under reflux for 60 minutes. After cooling to room temperature, the mixture is diluted with 100 ml of ethyl acetate, shaken with saturated aqueous ammonium chloride solution, dried with sodium sulphate and filtered through silica gel. From the filtrate, the solvent is carefully distilled off under water pump vacuum.

This gives 1.5 g (66% of theory) of 1-cyclopropyl-3-[4-methyl-3-methylthio-5-oxo-4,5-dihydro-[1,2,4]-triazol-1-yl-methyl)-phenyl]-propane-1,3-dione as an amorphous product which can be reacted further without purification.

Starting Materials of the Formula (VII)

Example (VII-1)

10 g (49 mMol) of 2-methyl-4-trifluoromethyl-benzoic acid are dissolved in 150 ml of ethanol and admixed with 1 ml of conc. sulphuric acid. The mixture is heated under reflux for 24 hours and then concentrated, the residue is taken up in methylene chloride and the mixture is extracted with saturated aqueous sodium bicarbonate solution. The methylene chloride phase is dried over sodium sulphate and concentrated under water pump vacuum.

This gives 9 g (80% of theory) of ethyl 2-methyl-4-trifluoromethyl-benzoate as an amorphous residue.

9 g (39 mMol) of ethyl 2-methyl-4-trifluoromethyl-benzoate are dissolved in 200 ml of carbon tetrachloride and admixed with 7 g (39 nMol) of N-bromo-succinimide and 0.1 g of dibenzoyl peroxide. After 6 hours of heating under reflux, the succinimide which has separated off is filtered off, and the filtrate is concentrated under water pump vacuum.

This gives 12 g of an amorphous residue which, in addition to ethyl 2-bromomethyl-4-trifluoromethyl-benzoate, contains 17% of ethyl 2,2-dibromomethyl-4-trifluoro-methyl-benzoate and 12% of ethyl 2-methyl-4-trifluoromethyl-benzoate.

4 g of ethyl 2-bromomethyl-4-trifluoromethyl-benzoate (about 70% pure) and 2.28 g (12.8 mMol) of 5-bromo-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 150 ml of acetonitrile and the solution is admixed with 5.3 g (38.4 Mol) of potassium carbonate and heated under reflux with vigorous stirring for 2 hours. The reaction mixture is taken up in water and repeatedly extracted with methylene chloride. The combined methylene chloride phases are dried over sodium sulphate, concentrated under water pump vacuum and chromatographed.

This gives 2 g (38% of theory) of 5-bromo-4-methyl-2-(2-ethoxycarbonyl-5-trifluoromethyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one as an amorphous product.

¹H-NMR (CDCl₃, 8): 5.46 ppm.

Example (VII-2)

6.7 g (40 Mol) of 4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one are initially charged in 150 ml of acetonitrile and stirred with 11 g (80 mMol) of potassium carbonate. The mixture is heated to 50° C., and a solution of 13.1 g (44 mMol) of methyl 3-bromomethyl-2,4-dichloro-benzoate in 20 ml of acetonitrile is then added dropwise with stirring, and the reaction mixture is heated with stirring and at reflux for another 15 hours. The mixture is then concentrated under water pump vacuum and the residue is taken up in methylene chloride, washed with 1N hydrochloric acid, dried with sodium sulphate and filtered. The filtrate is concentrated under reduced pressure, the residue is digested with petroleum ether and the resulting crysalline product is isolated by filtration with suction.

This gives 14.9 g (97% of theory) of 4-methyl-5-trifluoromethyl-2-(2,6-dichloro-3-methoxycarbonyl-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 109° C.

Analogously to the Examples (VII-1) and (VII-2), it is also possible to prepare, for example, the compounds of the general formula (VII) listed in Table 3 below.

TABLE 3 (VII) Examples of the compounds of the formula (VII) Ex. (position) (position) (position) physical No. R³ (R⁴)_n —A—Z Y data VII-3 (2-) Cl (4-) Cl OCH₃ m.p.: 229° C. logP = 2.27^a VII-4 (2-) Cl (4-) Cl OCH₃ m.p.: 120° C. logP = 2.38^a VII-5 (2-) Cl (4-) Cl OCH₃ m.p.: 127° C. logP = 2.55^a VII-6 (2-) Cl (4-) Cl OCH₃ m.p.: 121° C. logP = 2.04^a VII-7 (2-) Cl (4-) Cl OCH₃ m.p.: 68° C. logP = 2.73^a VII-8 (2-) Cl (4-) Cl OCH₃ m.p.: 129° C. logP = 2.72^a VII-9 (2-) Cl (4-) Cl OCH₃ m.p.: 164° C. logP = 2.18^a VII-10 (2-) Cl (4-) Cl OCH₃ m.p.: 158° C. logP = 1.55^a VII-11 (2-) Cl (4-) Cl OCH₃ m.p.: 106° C. logP = 2.16^a VII-12 (2-) Cl (4-) Cl OCH₃ m.p.: 126° C. logP = 2.11^a VII-13 (2-) Cl (4-) Cl OCH₃ m.p.: 146° C. logP = 1.65^a VII-14 (2-) Cl (4-) Cl OCH₃ m.p.: 178° C. logP = 1.86^a VII-15 (2-) Cl (4-) Cl OCH₃ m.p.: 97° C. logP = 2.36^a VII-16 (2-) Cl (4-) Cl OCH₃ m.p.: 99° C. logP = 2.73^a VII-17 (2-) Cl (4-) Cl OCH₃ m.p.: 56° C. logP = 3.08^a VII-18 (2-) Cl (4-) Cl OCH₃ m.p.: 102° C. logP = 3.05^a VII-19 (2-) Cl (4-) Cl OCH₃ m.p.: 131° C. logP = 2.70^a VII-20 (2-) Cl (4-) Cl OCH₃ m.p.: 135° C. logP = 1.97^a VII-21 (2-) Cl (4-) Cl OCH₃ m.p.: 143° C. logP = 2.42^a VII-22 (2-) Cl (4-) Cl OCH₃ m.p.: 85° C. logP = 2.58^a VII-23 (2-) Cl (4-) Cl OCH₃ logP = 1.98^a VII-24 (2-) Cl (4-) Cl OCH₃ logP = 2.07^a VII-25 (2-) Cl (4-) Cl OCH₃ m.p.: 157° C. logP = 2.94^a VII-26 (4-) CF₃ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.53 ppm. VII-27 (4-) NO₂ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.48 ppm. VII-28 (4-) NO₂ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.30 ppm. VII-29 (4-) SO₂CH₃ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.61 ppm. VII-30 (4-) Cl — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.08 ppm. VII-31 (4-) Cl — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.17 ppm. VII-32 (4-) Cl — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.00 ppm VII-33 (4-) SO₂CH₃ — OC₂H₅ logP = 1.53^a VII-34 (4-) Br — OC₂H₅ logP = 3.24^a VII-35 (4-) Br — OC₂H₅ logP = 3.40^a VH-36 (4-) F — OC₂H₅ logP = 2.41^a VII-37 (4-) F — OC₂H₅ logP = 2.45^a VII-38 (4-) Br — OC₂H₅ logP = 2.06^a VII-39 (4-) Br — OC₂H₅ logP = 2.64^a VII-40 (4-) Br — OC₂H₅ logP = 3.23^a VII-41 (4-) Br — OC₂H₅ logP = 3.02^a VII-42 (4-) Cl — OC₂H₅ logP = 3.23^a VII-43 (4-) Cl — OC₂H₅ logP = 3.31^a VII-44 (4-) Cl — OC₂H₅ logP = 3.14^a VII-45 (4-) NO₂ — OC₂H₅ logP = 2.42^a VII-46 (4-) NO₂ — OC₂H₅ logP = 2.82^a VII-47 (4-) CF₃ — OC₂H₅ logP = 3.48^a VII-48 (4-) CF₃ — OC₂H₅ logP = 3.38^a VII-49 (4-) CF₃ — OC₂H₅ logP = 3.02^a VII-50 (4-) CF₃ — OC₃H₇ logP = 3.91^a VII-51 (4-) OCH₃ — OC₂H₅ VII-52 (4-) OCH₃ — OC₂H₅ VII-53 (4-) CF₃ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.37 ppm. VII-54 (4-) CF₃ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.37 ppm. VII-55 — — OC₂H₅ VII-56 — — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.37 ppm. VII-57 — — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.40 ppm. VII-58 (4-) Br — OC₂H₅ logP = 2.95^a VII-59 (4-) Br — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.31 ppm. VII-60 (4-) Br — OC₂H₅ logP = 2.44^a VII-61 (4-) F — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.35 ppm. VII-62 (4-) F — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.53 ppm. VII-63 (4-) F — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.40 ppm. VII-64 (4-) F — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.36 ppm. VII-65 (4-) Br — OC₂H₅ logP = 3.34^a VII-66 (4-) Br — OC₂H₅ logP = 3.38^a VII-67 (4-) Br — OC₂H₅ logP = 3.31^a VII-68 (4-) Br — OC₂H₅ logP = 2.16^a VII-69 (4-) Br — OC₂H₅ logP = 2.41^a VII-70 (4-) CF₃ — OC₂H₅ logP = 3.51^a VII-71 (4-) CF₃ — OC₂H₅ logP = 3.54^a VII-72 (4-) Br — OC₂H₅ logP = 2.36^a VII-73 (4-) Br — OC₂H₅ logP = 2.88^a VII-74 (4-) CF₃ — OC₂H₅ logP = 2.68^a VII-75 (4-) Br — OC₂H₅ logP = 2.80^a VII-76 (4-) CF₃ — OC₂H₅ logP = 3.87^a VII-77 (4-) CF₃ — OC₂H₅ logP = 2.88^a VII-78 (4-) CF₃ — OC₂H₅ logP = 2.60^a VII-79 (4-) CF₃ — OC₂H₅ logP = 3.35^a VII-80 (4-) Br — OC₂H₅ logP = 2.86^a VII-81 (4-) Cl — OC₂H₅ logP = 2.83^a VII-82 (4-) Br — OC₂H₅ logP = 2.60^a VII-83 (4-) CF₃ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.36 ppm. VII-84 (4-) CF₃ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.37 ppm. VII-85 (4-) CF₃ — OC₂H₅ logP = 2.79² VII-86 (4-) CF₃ — OC₂H₅ logP = 3.67^a VII-87 (4-) CF₃ — OC₂H₅ logP = 3.80^a VII-88 (3-) CH₃ — OC₂H₅ logP = 2.54^a VII-89 (4-) — OC₂H₅ logP = 1.82^a VII-90 (4-) CF₃ — OC₂H₅ logP = 2.93^a VII-91 (4-) CF₃ — OC₂H₅ logP = 3.08^a VII-92 (4-) CF₃ — OC₂H₅ logP = 3.04^a VII-93 (4-) CF₃ — OC₂H₅ logP = 3.45^a VII-94 (4-) F — OC₂H₅ logP = 2.21^a VII-95 (4-) F — OC₂H₅ logP = 2.96^a VII-96 (4-) F — OC₂H₅ logP = 2.05^a VII-97 (4-) F — OC₂H₅ logP = 2.50^a VII-98 (4-) F — OC₂H₅ logP = 2.89^a VII-99 (4-) CF₃ — OC₂H₅ logP = 2.91^a VII-100 (4-) Cl — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.39 ppm. VII-101 (4-) Cl — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.50 ppm. VII-102 (4-) Cl — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.49 ppm. VII-103 (4-) CF₃ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.29 ppm. VII-104 (4-) CF₃ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.53 ppm. VII-105 (4-) CF₃ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.34 ppm. VII-106 (4-) SO₂CH₃ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.39 ppm. VII-107 (4-) SO₂CH₃ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.43 ppm. VH-108 (4-) SO₂CH₃ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.40 ppm. VII-109 (4-) SO₂CH₃ — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.38 ppm. VII-110 (4-) Br — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.49 ppm. VII-111 — — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.3 ppm. VII-112 — — OC₂H₅ ¹H-NMR (CDCl₃, δ): 5.44 ppm. VII-113 (4-) CF₃ — OC₂H₅ logP = 2.58^a VII-114 (4-) SO₂CH₃ — OCH₃ logP = 1.53^a VII-115 (4-) SO₂CH₃ — OCH₃ logP = 1.59^a VII-116 (4-) I — OCH₃ logP = 2.68^a VII-117 (4-) CF₃ — OCH₃ logP = 2.74^a VII-118 (4-) CF₃ — OCH₃ logP = 2.65^a VII-119 (4-) CF₃ — OC₂H₅ logP = 2.96^a VII-120 — — OCH₃ m.p.: 106° C. VII-121 (4-) CF₃ — OCH₃ logP = 3.37^a VII-122 (4-) CF₃ — OCH₃ logP = 3.29^a VII-123 (4-) CF₃ — OCH₃ logP = 3.26^a VII-124 (4-) Cl (2-) OCH₃ OCH₃ ¹H-NMR (DMSO-D₆, δ): 4.44 ppm. VII-125 (4-) Cl (2-) OCH₃ OCH₃ ¹H-NMR (DMSO-D₆, δ): 4.66 ppm. VII-126 (4-) Cl (2-) OCH₃ OCH₃ ¹H-NMR (DMSO-D₆, δ): 4.95 ppm.

The logP values given in Table 3 were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using a reverse-phase column (C 18). Temperature: 43° C.

(a) Mobile phases for the determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile—the corresponding data in Table 3 are labelled ^a).

(b) Mobile phases for the determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile—the corresponding data in Table 3 are labelled ^b).

Calibration was carried out using unbranched alkan-2-ones (with from 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by the retention times using linear interpolation between two successive alkanones).

The lambda-max values were determined in the maxima of the chromatographic signals, using the UV spectra from 200 nm to 400 nm.

Use Examples Example A

Pre-Emergence Test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the preparation of active compound such that the particular amount of active compound desired is applied per unit area. The concentration of the spray liquor is chosen so that the particular amount of active compound desired is applied in 1000 litres of water per hectare.

After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.

The figures denote:

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds of preparation examples 3 and 4 exhibit strong action against weeds, whilst being tolerated well by crop plants, such as, for example, maize.

Example B

Post-Emergence Test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with the preparation of active compound such that the particular amounts of active compound desired are applied per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 1000 1 of water/ha.

After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.

The figures denote:

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds of Preparation Examples 3 and 4 exhibit very strong activity against weeds, whilst being tolerated well by crop plants, such as, for example, wheat.

Claims

1-21. (canceled)

22. A compound of the Formula (IE) in which

n represents the number 0, 1 or 2,

A represents a single bond or represents alkanediyl (alkylene) having 1 to 4 carbon atoms,

R1 represents hydrogen, represents optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl having 1 to 6 carbon atoms, represents optionally cyano- or halogen-substituted alkenyl having 2 to 6 carbon atoms, or represents optionally cyano-, halogen- or C1-C4-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,

R2 represents hydrogen, cyano, carbamoyl, halogen, represents in each case optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy or alkoxycarbonyl having in each case up to 6 carbon atoms, or represents optionally halogen-substituted alkylthio, alkylsulphinyl or alkylsulphonyl having 1 to 6 carbon atoms,

R3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, represents in each case optionally halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 4 carbon atoms in the alkyl groups, or represents alkylamino, dialkylamino or dialkylaminosulphonyl having in each case up to 4 carbon atoms in the alkyl groups,

R4 represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, represents in each case optionally halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 4 carbon atoms in the alkyl groups, or represents alkylamino, dialkylamino or dialkylaminosulphonyl having in each case up to 4 carbon atoms in the alkyl groups, and

Z represents one of the heterocyclic groupings below

in which the dotted bond is in each case a single bond or a double bond, and each heterocyclic grouping preferably only carries two substituents of the definition R5 and/or R6,

Q represents oxygen or sulphur,

R5 represents hydrogen, hydroxyl, mercapto, cyano, halogen, represents in each case optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkylamino or dialkylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl, alkenyloxy, alkenylthio or alkenylamino having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino, piperidino or morpholino, or—if two adjacent radicals R5 and R5 are located at a double bond—also together with the adjacent radical R5 represents a benzo grouping, and

R6 represents hydrogen, hydroxyl, amino, alkylidenamino having up to 4 carbon atoms, represents in each case optionally halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylamino, dialkylamino or alkanoylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl or alkenyloxy having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkylalkyl or cycloalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 3 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenyl or benzyl, or together with an adjacent radical R5 or R6 represents optionally halogen- or C1-C4-alkyl-substituted alkanediyl having 3 to 5 carbon atoms,

where the individual radicals R5 and R6—if a plurality of them are attached to the same heterocyclic grouping—can have identical or different meanings within the scope of the above said definition of said radicals.

23. A compound of the Formula (II) in which

n represents the number 0, 1, 2 or 3,

A represents alkanediyl (alkylene),

R1 represents hydrogen or represents in each case optionally substituted alkyl, alkenyl or cycloalkyl,

R2 represents hydrogen, cyano, carbamoyl, halogen, or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl,

R3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl,

R4 represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl, and

X represents halogen,

excluding ethyl 4-(2-bromo-methyl-benzoyl)-5-cyclopropyl-isoxazole-3-carboxylate.

24. A compound of the Formula (IV) in which

n represents the number 0, 1, 2 or 3,

A represents alkanediyl (alkylene),

R1 represents hydrogen or represents in each case optionally substituted alkyl, alkenyl or cycloalkyl,

R3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl,

R4 represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl, and

Z represents an optionally substituted 4- to 12-membered, saturated or unsaturated, monocyclic or bicyclic, heterocyclic grouping which contains 1 to 4 hetero atoms (up to 4 nitrogen atoms and optionally—alternatively or additionally—one oxygen atom or one sulphur atom, or one SO grouping or one S02 grouping) and which additionally contains one to three oxo groups (C═O) and/or thioxo groups (C═S) as components of the heterocycle.