EP1478621A2 - Substituted aryl ketones - Google Patents

Abstract

The invention relates to novel substituted aryl ketones of formula (I), in which Z, X, R and n have the meanings as cited in the description. The invention also relates to a method for producing these substituted aryl ketones, to their use as plant treatment agents and to intermediate products for producing compounds of formula (I).

Description

Substituted aryl ketones

The invention relates to new substituted aryl ketones, processes for their preparation and their use as plant treatment agents, in particular as herbicides.

It is already known that certain substituted aryl ketones have herbicidal properties (cf. EP-A-Ö90 262, EP-A-135 191, EP-A-186 118, EP-A-186 119, EP-A-186 120, EP-A-319 075, EP-A-352 543, 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-625 505, EP-A-625 508, EP-A-636 622, US-A-5 804 532, US-A- 5 834 402, US-A-5 846 906, US- A-5 863 865, WO-A-95/31446, ^" WO-A-96/26192, WO-A-96/26193, WO-A-96/26200, WO-A-96/26206, WO-A -97/27187, WO-A-97/35850, WO-A-97/41105, WO-A-97/41116, WO-A-97/41117, WO-A-97/41118, WO-A-97 / 43270, WO-A-97/46530, WO-A-98/28981, WO-A-98/31681, WO-A-

98/31682, WO-A-99/03856, WO-A-99/07688, WO-A-99/07697, WO-A-99/10327, WO-A-99/10328, WO-A-00 / 05221, WO-A-00/21924). However, the action of these compounds is not satisfactory in all respects.

The new substituted aryl ketones of the formula (I)

in which

n represents the numbers 0, 1 or 2, R represents in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,

X ^' for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio,

Alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl, and

Z represents one of the groupings below,

in which

m represents the numbers 0 to 6,

R ^{1 stands} for hydrogen, halogen or for optionally substituted alkyl, alkylthio or aryl, or - if m stands for the numbers 2 to 6 - optionally also together with a second radical R ^{1 stands} for oxygen or alkanediyl (alkylene) .

R represents hydroxy, formyloxy, halogen, or for each optionally substituted alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylcarbonyloxyalkyloxy arylcarbonyloxyalkyloxy, Arylalkylsulfinyl, arylalkylsulfonyl or heterocyclyl bonded via nitrogen, R ^{3 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or each optionally substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkoxycarbonyl or cycloalkyl,

R ^{4 stands} for hydrogen or for optionally substituted alkyl, alkenyl,

Alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, and

R ⁵ for hydroxy, formyloxy, or for optionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, arylalkoxy, arylcarbonyloxy,

Arylcarbonylalkoxy or arylsulfonyloxy,

found.

In the definitions are the hydrocarbon chains, such as alkyl or alkanediyl

- also in connection with heteroatoms, such as in alkoxy - in each case straight-chain or branched.

Insofar as the compounds of the general formula (I) can exist in different tautomeric or stereoisomeric forms, the invention includes the respective possible tautomeric or stereoisomeric forms.

Preferred substituents or preferred ranges of the radicals present in the formulas listed above and below are defined below.

n is preferably the number 0 or 2.

R preferably represents optionally cyano-, halogen-, C ₁ -C ₄ alkoxy, C _\ - C alkylthio, alkylsulfinyl or CrC ₄ -C ₄ - alkylsulfonyl-substituted alkyl having 1 to 6 carbon atoms, for alkenyl or alkynyl, each optionally substituted by cyano or halogen, each having 2 to 6 carbon atoms, for cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or C ₁ -C alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 Carbon atoms in

The alkyl moiety, or represents in each case optionally substituted by nitro, cyano, halogen, -C ₄ - alkyl, -C ₄ - haloalkyl, Cι-C ₄ -alkoxy or C ₁ -C ₄ haloalkoxy substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part.

X preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for each optionally substituted by cyano, halogen, dC ₄ -alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfmyl or C1-C4-alkylsulfonyl

Alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl each having 1 to 6 carbon atoms in the alkyl groups.

m preferably represents the numbers 0, 1, 2 or 3.

R ¹ preferably represents hydrogen, halogen, each optionally substituted by cyano, halogen, C 1 -C ₄ alkoxy, C 1 -C ₄ alkylthio, C 1 -C ₄ alkylsulfmyl or CrC - alkylsulfonyl substituted alkyl or alkylthio, each with 1 to 6 Carbon atoms, or for phenyl, or - if m is 2 or 3 - optionally together with a second radical R ¹ for oxygen or alkanediyl (alkylene) having 3 to 5 carbon atoms.

R> 2 preferably represents hydroxyl, formyloxy, halogen, for alkoxy, alkylthio, alkylsulfmyl, each optionally substituted by cyano, halogen, .Cι-C ₄ alkoxy, CrC - alkoxycarbonyl, Cι-C alkylthio, Cι-C ₄ alkylsulfinyl or Cι-C ₄ alkylsulfonyl, Alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms, for alkenyloxy or alkynyloxy each optionally substituted by halogen, each having 3 to 6 carbon atoms, each optionally containing nitro, cyano, halogen, C 1 -C 4 -alkyl, -C-C ₄ - haloalkyl, CrC ₄ -alkoxy, Cι-C ₄ -haloalkoxy, C ₁ -C ₄ -alkylthio, CrC ₄ - haloalkylthio, Cι-C ₄ - alkylsulfinyl, CrC ₄ -haloalkylsulfinyl, CrC ₄ -

Alkylsulfonyl or C ₁ -C ₄ haloalkylsulfonyl substituted aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylcarbonyloxy, arylcarbonylalkoxy, aryl-

• sulfonyloxy, arylalkoxy, aylalkylthio, arylalkylsulfinyl or arylalkylsulfonyl, each with 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part or for pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl bonded via nitrogen.

R ³ preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, in each case optionally substituted by cyano, halogen, CrC ₄ alkoxy, CrC - alkylthio, C 1 -C ₄ -alkylsulfinyl or CrC ₄ - alkylsulfonyl ^' alkyl, alkoxy, alkylthio, Alkylsulfinyl, alkylsulfonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups, or for optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl

Cycloalkyl of 3 to 6 carbon atoms.

R ⁴ preferably represents hydrogen, represents optionally cyano-, _halogen. dC ₄ - alkoxy, -CC ₄ -alkylthio, -C-C ₄ - alkylsulfinyl or -C-C ₄ - alkylsulfonyl substituted alkyl with 1 to 6

Carbon atoms, for alkenyl or alkynyl, each optionally substituted by cyano or halogen, each having 3 to 6 carbon atoms, for cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or C 1 -C ₄ -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 Carbon atoms in

The alkyl moiety, or represents in each case optionally substituted by nitro, cyano, halo, Cι-C ₄ - alkyl, Cι-C - haloalkyl, ^'Cι-C ₄ -alkoxy, C haloalkoxy, dC ₄ alkylthio, Cι-C ₄ - Haloalkylthio, -C-C ₄ - alkylsulfinyl, C ₁ -C -haloalkylsulfinyl, Cι-C ₄ - alkylsulfonyl or Cι-C ₄ -haloalkylsulfonyl substituted aryl or arylalkyl, each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part.

R ⁵ preferably represents hydroxy, formyloxy, alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms in the alkyl groups, optionally substituted by cyano, halogen or dC ₄ -alkoxy, for alkenyl optionally substituted by cyano or halogen - oxy or alkinyloxy having in each case 3 to 6 carbon atoms, or represents in each case optionally substituted by nitro, cyano, halogen, Ci-C ₄ - alkyl, dC ₄ - haloalkyl, _Cι-C4 alkoxy, -C ₄ -haloalkoxy, C ₁ -C ₄ -Alkylthio, dC ₄ - haloalkylthio, dd-alkylsulfinyl, -C-C ₄ -haloalkylsulfmyl, Cι-C ₄ - alkylsulfonyl or C] -C ₄ -haloalkylsulfonyl-substituted arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or axylsulfonyloxy in each of 6 or 10 Aryl group and optionally 1 to 4 carbon atoms in the alkyl part.

n particularly preferably stands for the number 2. R particularly preferably represents in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl and / or n- or i-propylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, for each optionally Ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl substituted by cyano, fluorine, chlorine and / or bromine, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl and / or n- or i- Propyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylrnethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n- , i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy and od he trifluoromethoxy substituted phenyl, naphthyl, phenylmethyl, phenylethyl or phenylpropyl.

X particularly preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or each optionally by cyano, fluorine, chlorine, methoxy, ethoxy,

Methylthio, ethylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, h-, 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, methylsulfinyl, ethylsulfmyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n - or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulfonyl or diethylaminosulfonyl.

m particularly preferably represents the numbers 0, 1 or 2. R ¹ particularly preferably represents hydrogen, fluorine, chlorine or bromine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, Methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-Butylthio, or for phenyl, or - if m is 2 - optionally also together with a second radical R ¹ for oxygen, propane-1,3-diyl or butane-1,4-diyl.

R ² particularly preferably represents hydroxyl, formyloxy, fluorine or chlorine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,

Methylsulfinyl, ethylsulfmyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyl-oxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylamino-carbonyloxy, n- or i-propylaminyloxy-oxyloxy sulfonyloxy- , n- or i-Propylsulfonyloxy, for each optionally substituted by fluorine, chlorine and or bromine ^• propenyloxy, butenyloxy, propynyloxy or butynyloxy, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio,

Ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, Ethylsulfmyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or Trifiuormethylsulfonyl substituted phenyloxy, phenylthio, Phenylsulfmyl, phenylsulphonyl, phenylcarbonyloxy, Phenylcarbonylmethoxy, phenylsulphonyloxy, phenylmethoxy, phenylmethylthio, Phenylmethylsulfϊnyl or phenylmethylsulfonyl or for pyrazolyl, imidazolyl, triazolyl bound via nitrogen.

R ³ particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio , n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-

Propoxycarbonyl, or for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally substituted by cyano, fluorine, chlorine, methyl or ethyl.

R ⁴ particularly preferably represents hydrogen, " ^• in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by cyano, fluorine, chlorine and / or bromine, for each optionally by Cyano, fluorine, chlorine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or for each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl,

Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, Difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfmyl, trifluoromethylsulfinyl, methylsulfonyl, ethyl _. sulfonyl or trifluoromethylsulfonyl substituted phenyl or phenylmethyl. R particularly preferably represents hydroxyl, formyloxy, methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylammocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, each optionally chlorine by cyano, fluorine and / or bromine-substituted.Propenyloxy, butenyloxy, propynyloxy or butynyloxy, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfmyl, trifluoromethylsulfonyl or methylifluoromethylsulfonyl, methylifluoromethylsulfonyl, or ethylsulfonyl substituted phenylmethoxy, phenylcarbonyloxy, phenylcarbonylmethoxy or phenylsulfonyloxy.

R very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i- or s-, each optionally substituted by fluorine and / or chlorine.

Butyl, for each optionally substituted by fluorine, chlorine or methyl

Cyclopropyl, cyclopentyl or cyclohexyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy,

Difluoromethoxy or trifluoromethoxy substituted phenyl or phenylethyl.

X very particularly preferably represents nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or for each optionally substituted by fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl and / or ethylsulfonyl, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl, ethylsulfonyl or dim dimethylaminosulfonyl.

m very particularly preferably stands for the number 0.

R, ι ^' very particularly preferably represents hydrogen, each methyl optionally substituted by fluorine or chlorine,

, Ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, or for phenyl, or - if m is 2 - optionally together with a second radical R ¹ for oxygen, propane l, 3-diyl or butane-1,4-diyl.

R ² very particularly preferably represents hydroxyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, each optionally substituted by fluorine or chlorine, Acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylammocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propyl for propenyloxy, butenyloxy, propynyloxy or butynyloxy each optionally substituted by fluorine, chlorine and / or bromine, for each optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy , n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfmyl, trifluoromethylsulfmyl, methylsulfonyl, ethyl sulfonyl or trifluoromethylsulfonyl substituted phenyloxy, phenylthio, phenylcarbonyloxy, phenyl-- carbonylmethoxy, phenylsulfonyloxy, phenylmethoxy or phenylmethylthio or for pyrazolyl or imidazolyl bound via nitrogen.

R very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n-, each optionally substituted by fluorine or chlorine. or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or for cyclopropyl which is optionally substituted by fluorine, chlorine or methyl.

R ⁴ very particularly preferably represents hydrogen, in each case methyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl , Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine, chlorine and / or bromine, for each optionally by fluorine, Chloro or methyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or for each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, Methoxy, ethoxy, n- or i-propoxy,

Difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfmyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl or phenyl substituted phenyl.

R) 5 very particularly preferably represents hydroxy, for in each case optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylammocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, for propenyloxy, butenyloxy, propynyloxy or butynyloxy, each optionally substituted by fluorine, chlorine and / or bromine or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy,

Difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfmyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl, phenylcarbonyloxy, phenylcarbonyloxy, phenylcarbonyloxy-, phenyl- carbonyl- methoxy- phenyl- methoxy- phenyl-

X most preferably represents fluorine, chlorine, bromine, iodine, methoxy, methylthio, methylsulfonyl or trifluoromethyl.

R most preferably represents methyl, ethyl, n-propyl, i-propyl, n-butyl, i-

Butyl, t-butyl, 1,1,1-trifluoroethyl or phenyl.

R ¹ most preferably represents hydrogen or methyl.

R most preferably represents hydroxy, chlorine or n-pyrazolyl.

R ³ most preferably represents hydrogen or methyl.

R ⁴ most preferably represents methyl or ethyl. R ⁵ most preferably represents hydroxy, propargyloxy, n-propylsulfonyloxy, tosyloxy, (benzoyl) methoxy, (ethoxycarbonyl) methoxy, or benzyloxy optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl.

Compounds of formula (I) in which

R represents methyl, ethyl, n-, i-propyl, n-, i-, s-, t-butyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl, propargyl, benzyl or phenyl which is optionally substituted by fluorine, chlorine, nitro, cyano .

X represents fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl or nitro,

n stands for 0 or 2 and

Z have the meaning given above,

are particularly highlighted.

Compounds of formula (I) in which

R for methyl,

X is trifluoromethyl, n is 2 and

Z have the meanings given above

are also particularly highlighted.

Compounds of formula (I) in which R for methyl,

X is bromine, n is 2 and

Z have the meanings given above,

are also particularly highlighted.

Compounds of the formula (Ia)

in which

n, X, R, R ³ and R ^{4 have} the meanings given above.

Compounds of the formula (Ib)

in which

n, X, R,> 3 "and R have the meanings given above and

R, 5 'has the meanings given for R with the exception of hydroxy. Compounds of the formula (Ic)

in which

n, X and R have the meanings given above.

Compounds of the formula (Id)

in which

n, X and R have the meanings given above, and

R ^{2 has} the meanings given above for R ² with the exception of hydroxy.

The aforementioned definitions of the substituents can be combined with one another in any manner. Individual definitions can also be omitted.

According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred. According to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

According to the invention, very particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

The general definitions given above or those specified in preferred areas apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation.

These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.

The new substituted aryl ketones of the formula (I) are notable for strong and selective herbicidal activity.

The new substituted aryl ketones of the formula (I) are obtained if carboxylic acids of the general formula (II),

in which

n, R and X have the meaning given above - or reactive derivatives thereof, such as corresponding acid halides, acid cyanides or esters -

with compounds of the general formula (III)

H-Z (III) in which

Z has the meaning given above,

if appropriate in the presence of a dehydrating agent and if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,

and, if appropriate, after carrying out the process according to the invention on the compounds of the general formula (I) thus obtained as part of the definition of the substituent, subsequent reactions (for example substitution, oxidation or reduction reactions) for conversion into other compounds of the general formula (I) carried out according to usual methods.

If, for example, 4-chloro-2- (ethylsulfinylmethyl) benzoic acid and cyclohexan-1,3-dione are used as starting materials, the course of the reaction in the process according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the carboxylic acids to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (II), n, R and X have preferably those meanings which have already been given above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred, very particularly preferred or most preferred for n, R and X.

Some of the starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. J. Med. Chem. 21 (1978), 529-536; J. Org. Chem. 36 (1971) , 3636-3638; DE-A-20 65 636; US-37 33 364; manufacturing examples). Individual compounds of formula (II) are new and the subject of the present application.

Formula (III) provides a general definition of the compounds to be used further as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (III), Z preferably has the meaning which has already been given for Z in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred, very particularly preferred or most preferred , The starting materials of the general formula (III) are known organic synthetic chemicals.

The process according to the invention for the preparation of the compounds of the formula (I) is preferably carried out using one or more reaction auxiliaries. The usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries. These preferably include alkali metal or alkaline earth metal, acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide , Sodium or potassium, methanol,

-ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; continue too basic organic nitrogen compounds, such as trimethylamine, tri-, ethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine , Pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5 -Ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, N-ethyl-piperidine, N-methyl-morpholine, N-ethyl-morpholine, 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).

The process according to the invention is optionally carried out using a dehydrating agent. The usual chemicals suitable for binding water come into consideration here.

Examples of these are dicyclohexylcarbodumide, carbonyl-bis-imidazole and propanephosphonic anhydride.

Dicyclohexylcarbodumide and propanephosphonic anhydride may be mentioned as particularly suitable dehydrating agents.

The process according to the invention for the preparation of the compounds of general

Formula (I) is preferably carried out using one or more diluents. Inert organic solvents are particularly suitable as diluents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, 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 or 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 hexamethyl triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide.

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under increased or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger 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. The work-up is carried out using customary methods (cf. the manufacturing examples).

The compounds of formula (II)

in which X stands for CF ₃ ,

n and R have the meanings given above are new and the subject of the present application.

Compounds of formula (II) in which

X is CF ₃ , n is 0, 1 or 2 and R is methyl

are particularly preferred.

Compounds of formula (II) in which

X is bromine, n is 0, 1 or 2 and

R represents methyl

are also particularly preferred.

The compounds of formula (VI)

in which

X stands for CF ₃ , R ^{6 represents} alkyl, benzyl or AUyl, and R has the meanings given above,

are new and the subject of the present application.

Compounds of formula (VI) in which

X stands for CF ₃ ,

RR ⁶⁶ for MMeethyyll ,, EE1thyl, Allyl or Benzyl stands and

R represents methyl, ethyl, allyl or benzyl

are particularly preferred.

The new compounds of the formulas (II) and (VI) are suitable for the preparation of active compounds for pharmaceutical, biological and agricultural purposes.

They are particularly suitable for the preparation of compounds of the formula (I).

The new carboxylic acids of the general formula (II) are obtained if halomethylbenzoic acid esters of the general formula (IV)

in which

X has the meaning given above, R ^{6 represents} alkyl (in particular methyl or ethyl), benzyl or allyl, and

X ^{I represents} halogen (especially chlorine or bromine), with mercapto compounds of the general formula (N),

HS-R (V) in which

R has the meaning given above,

- or with alkali metal salts, such as sodium or potassium salts, of compounds of the formula (V) -

optionally in the presence of one or more reaction aids, e.g. Potassium carbonate, triethylamine or sodium hydride, and optionally in the presence of one or more diluents, e.g. Tetrahydrofuran, acetonitrile or N, N-dimethylformamide, at temperatures between 0 ° C. and 150 ° C., and optionally the carboxylic acid esters of the general formula (VI) thus obtained,

in which

R, R _> 6 and X have the meanings given above,

with oxygenating agents, such as hydrogen peroxide, optionally in the presence of one or more diluents, such as acetic acid and / or water, at temperatures between 0 ° C. and 120 ° C., and the esters thus obtained by customary methods, for example by reaction with aqueous sodium hydroxide and then converted into the carboxylic acids of the formula (II) using hydrochloric acid (cf. the preparation examples). Some of the compounds of the formula (NT) are known and / or can be prepared by known processes. Individual compounds of formula (VI) are new and the subject of the present application.

The active compounds according to the invention can be used as defoliants, desiccants, herbicides and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. 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 e.g. can be used in the following plants:

Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda,

Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lamium, Lammium Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala,

Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linurn, Lycopersicon,

Νicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus,. Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa,

Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.

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

Depending on the concentration, the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on paths and squares with and without tree cover. The active compounds according to the invention for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm,

Cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land as well as for selective weed control in annual crops.

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

In certain concentrations or application rates, the active compounds according to the invention can also be used to control animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds. According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds. ^"

The treatment of the plants and plant parts according to the invention with the active substances directly or by action on their ^{'environment,} habitat or storage space by the customary treatment methods, for example by dipping, spraying, evaporation, fogging, scattering, painting on and the case of propagation material, in particular with seeds , still by single or multi-layer wrapping.

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and femst encapsulations in polymers

Substances.

These formulations are made in a known manner, e.g. by mixing

the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, thus emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as a stretching agent, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as

Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Possible solid carriers are: e.g. Ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, as solid carriers, are suitable for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,

Coconut shells, corn cobs and tobacco stalks; as emulsifying and or foaming agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite waste liquor and

Methylcellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho- lipids such as cephalins and lecithins and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known herbicides and / or with substances which improve crop tolerance (“safeners”) for weed control, ready-to-use formulations or tank mixes being possible mixtures with weed control compositions which contain one or more known herbicides and a safener are also possible.

Known herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium),

Ametryne, Amicarbazone, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine,

Azafenidin, Azimsulfüron, Beflubutamid, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl), Bentazon, Benzfendizone, Benzobicyclon, Benzofenap, Benzoylprop

(-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylates, cafenstrole,

Caloxydim, carbetamides, carfentrazone (-ethyl), chloromethoxyfen, chloramben,

Chloridazon, Chlorimuron (-ethyl), Chlomitrofen, Chlorsulf ron, Chlortoluron, Cinidon (-ethyl), Cinmethylin, Cinosulfuron, Clefoxydim, Clethodim, Clodinafop (- propargyl), Clomazone, Clomeprop, Clopyralid, Clanopyrasulfuron - sulam (-methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron,

Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, Desmedipham, Diallate, Dicamba, Dichloroprop (-P), diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diuronid, diphenamide, diphenamide, diphenamide, diphenamid, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (- methyl), Ethofümesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop (-P-ethyl), Fentrazamide, Flamprop (-isopropyl, -isopropyl-L, -methyl), Flazasulfuron Florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flufenacet, Flufenpyr, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumet-sulam, Fluometuron, Fluorochloridone, Fluoroglycupox (methyl Fluprop-acil, Flurpyrsulfüron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr

(-butoxypropyl, -meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthimide, Fomesafen, Foramsulfuron, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl, -P- methyl), hexazinone, imazamethabenz (-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imaza- quin, imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, iso-propalin, isoproturon, isourox, isouron, isouron, isouron, Isoxaflutole, Isoxapyrifop, Ketospiradox, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Mesotione, Meta itron, Metazachlor, Methab enzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachox, Metobromonuron, Metronuron, Metosulamuronuron, Metosulamuronuret, -methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalinox, pendimethalinox Pethoxamide, phenmedipham, Picolinafen, Piperophos, Preilachlor, Primisulfuron (-methyl), Profluazol, Profoxydim, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone (-sodium), Propyzamide,

Prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxime, pyributicarb, pyridate, pyridatol, pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchloracin, quinchlorac oclamine, Quizalofop (-P-ethyl, -P-tefuryl), Rimsulfüron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Tepraloxynine, Then Terbuthylazine, Terbuthylazine, Terbuthylazine . Thiafluamides, thiazopyr, thidiazimin, thifensulfüron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallates, triasulfüron, tribenuron (-methyl), triclopyr, tri-diphane, trifluralin, trifloxysulfuron, trifitosulfuron, trifitosulfuron, trifitosulfuron, trifitosulfuron, trifitosulfuron, trifitosulfuron, trifitosulfuron.

Known safeners are also suitable for the mixtures, for example AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA-24, dichlormid, Dymron, Fenclorim, Fenchlorazol (-ethyl) , Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), MCPA, Mecoprop (-P), Mefenpyr (-diethyl), MG-191, Oxabetrinil, PPG-1292, R-29148.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents to 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 usual way, e.g. by pouring, spraying, spraying, sprinkling.

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

The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.

As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wildly coming or treated by conventional biological breeding methods, such as crossing or protoplast fusion plant species and plant varieties and their parts. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically

Modified Organisms) and their parts. The term "parts" or "parts of plants" or "plant parts" was explained above.

Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant cultivars are understood to mean plants with certain properties (“traits”) which have been obtained by conventional breeding, by mutagenesis, or else by recombinant DNA techniques. These can be varieties, bio and genotypes.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, growing season, nutrition), the treatment according to the invention can also give rise to superadditive ("synergistic") effects. For example, reduced application rates and / or widening of the spectrum of action and / or an increase in the action of the substances and agents which can be used according to the invention - also in combination with other agrochemicals

Active ingredients, better growth of crops, increased tolerance of crops to high or low temperatures, increased tolerance of crops to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher Nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the effects that are actually to be expected.

The preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, by virtue of the genetic engineering modification, received genetic material which contained them Gives plants special beneficial valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher nutritional value the harvest products, higher shelf life and / or workability of the harvest products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicides

Agents. Examples of transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted. The ^" traits" are particularly emphasized the increased defense of the plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes CryΙA (a), CryΙA (b) , CryΙA (c), CrylLA, CrylllA, CryIILB2, Cry9c Cry2Ab, Cry3Bb and CryLF as well as their combinations) are produced in the plants (hereinafter referred to as "Bt plants"). The increased resistance is also particularly emphasized as properties ("traits") of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, phytoalexins, elicitors as well as resistance genes and correspondingly expressed proteins and toxins. As traits, the increased tolerance of the plants to certain herbicidal active substances is particularly emphasized , for example imidazolinones, sulfonylureas, glyphosate or phosphinothricin (for example "PAT" -. gene) Genes conferring traits can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD® (e.g.

Corn, Cotton, Soybean), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® (Cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinothricin, e.g. rapeseed), IMI® (tolerance against imidazolinones) and

STS® (tolerance to sulfonylureas e.g. maize). The herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfϊeld® (e.g. maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").

The plants listed can be treated according to the invention particularly advantageously with the compounds of the general formula I or the active compound mixtures according to the invention, the synergistic effects mentioned above occurring with the transgenic plants or plant cultivars in addition to the good control of the weed plants. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.

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

Preparation Examples:

example 1

A mixture of 3.50 g (12.4 mmol) of 2-methylsulfonylmethyl-4-trifluoromethylbenzoic acid, 1.39 g (12.4 mmol) of 1-ethyl-5-hydroxy-1H-pyrazole, 3.07 g ( 14.9 mmol) of dicyclohexylcarbodumide and 75 ml of acetonitrile is stirred for 15 hours at room temperature (approx. 20 ° C.). Then 3.45 ml of triethylamine and 0.35 ml of trimethylsilyl cyanide are added to this mixture and the reaction mixture is stirred for 15 hours at room temperature. The mixture is then concentrated under reduced pressure, the residue is stirred with saturated aqueous sodium carbonate solution, diethyl ether is added and the mixture is filtered. The aqueous phase of the filtrate is separated off, acidified with 2N hydrochloric acid and extracted with methylene chloride. The organic extraction solution is washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, the residue is digested with diethyl ether / petroleum ether and the crystalline product is isolated by suction.

3.8 g (81.5% of theory) of (1-ethyl-5-hydroxy-1H-pyrazol-4-yl) - (2-methylsulfonylmethyl-4-trifluoromethyl-phenyl) -methanone are obtained. LogP = 1.88. Example 2

A mixture of 1.00 g (2.66 mmol) (l-ethyl-5-hydroxy-1H-pyrazol-4-yl) - (2-methylsulfonylmethyl-4-trifluoromethyl-phenyl) -methanone, 0.66 g ( 2.66 mmol) 4-bromo-benzyl bromide, 0.485 gl, 8-diazabicyclo [5.4.0] -undec-7-ene (DBU) and 50 ml toluene are heated to reflux with stirring for 2 hours and then concentrated under reduced pressure. The residue is shaken with 2N hydrochloric acid / ethyl acetate, the organic phase is dried with sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, the residue is digested with hexane / diethyl ether / isopropanol and the crystalline product is isolated by suction.

0.55 g (38% of theory) [l-ethyl-5- (4-bromophenyl-methoxy) -lH-pyrazol-4-yl] - (2-methylsulfonylmethyl-4-trifluoromethylphenyl) - methanone. LogP = 3.76.

Analogously to Examples 1 and 2 and in accordance with the general description of the production process according to the invention, it is also possible, for example, to prepare the compounds of the general formula (I) listed in Tables 1 and 2 below.

Table 1:

Table 2

Notes on the "Physical data" column in Tables 1 and 2: Either the logP value, the melting point or a characteristic NMR signal are given.

The logP values specified in the tables were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal 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 - corresponding measurement results are marked in Table 1 with a). (b) eluents for determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^D ). The calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).

The lambda maximums were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.

The melting points given in the tables were determined using standard laboratory methods using a device from Büchi, Melting point B-545, in melting point determination tubes. The melting point is given in ° C.

The determination of the -NMR data was carried out on a 300 MHz device as

Solvent was used CDCI3. The characteristic signal of the CH ₂ group between the central phenyl ring and the rest -S (O) _n R is given.

Starting materials of formula (II):

Example (II-1) - Level 1

A mixture of 15 g (50.5 mmol) of 2-bromomethyl-4-trifluoromethyl-benzoic acid, methyl ester, 4.24 g (60.6 mmol) of sodium methyl mercaptide and 100 ml of acetonitrile is heated under reflux for 90 minutes with stirring. Then the

The mixture is suctioned off through a silica gel frit, washed with petroleum ether and the solvent is carefully distilled off from the filtrate under reduced pressure. 12 g (90% of theory) of 2-methylthiomethyl-4-trifluoromethyl-benzoic acid methyl ester are obtained.

Level 2

12.0 g (45.45 mmol) of 2-methylthiomethyl-4-trifluoromethyl-benzoic acid methyl ester are taken up in 150 ml of acetic acid and stirred at room temperature with 10.2 g of a 35% aqueous hydrogen peroxide solution (0.10 mol H ₂ O ₂ ) added dropwise. The mixture is then heated to 100 ° C. for 90 minutes with stirring and then to approximately that. poured double the amount of ice. The product obtained in crystalline form is isolated by suction. 9.1 g (68% of theory) of 2-methylsulfonylmethyl-4-trifluoromethylbenzoic acid methyl ester are obtained.

level 3

A mixture of 9.0 g (30.4 mmol) of 2-methylsulfonylmethyl-4-trifluoromethylbenzoic acid methyl ester, 50 ml of 40% aqueous sodium hydroxide solution and 50 ml of water is heated to 90 ° C. for 60 minutes. After cooling, it is diluted with water to about twice the volume, with conc. Acidified hydrochloric acid and the crystalline product isolated by suction.

7.15 g (83% of theory) of 2-methylsulfonyfmethyl-4-trifluoromethylbenzoic acid are obtained. Application 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 specified amount is given

Amount of emulsifier and dilute the concentrate with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation so that the desired one

Amount of active ingredient is applied per unit area. The active ingredient concentration in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:

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

In this test, for example, the compounds according to Preparation Example 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 show , 22 and 23 with good tolerance to crops such as maize and soybeans, strong activity against weeds. 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 with a height of 5 to 15 cm are sprayed with the active substance preparation in such a way that the desired quantities of active substance are applied per unit area. The concentration of the spray liquor is chosen so that in

1000 1 water / ha the desired. Active ingredient quantities are applied.

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

It means:

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

In this test, for example, the compounds according to the preparation example show

1, 2, 3, 5, 18, 19, 20 and 23 with good tolerance to crop plants, such as e.g. Corn and wheat, strong weed control.

Claims

Patentansprflche

1. Compounds of formula (I)

in which n stands for the numbers 0, 1 or 2,

R represents optionally substituted alkyl, alkenyl, alkynyl,

Cycloalkyl, cycloalkylalkyl, aryl or axylalkyl, X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkoxy,

Alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl, and Z represents one of the following groups

where m stands for the numbers 0 to 6,

R ^{1 represents} hydrogen, halogen or optionally substituted alkyl, alkylthio or aryl, or - if m represents the numbers 2 to 6 - optionally together with a second radical R ^{1 represents} oxygen or alkanediyl ( Alkylene),

R ² for hydroxyl, formyloxy, halogen, or for optionally substituted alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylamino carbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, aryloxy, arylthio, arylsulfmyl, arylsulfonyl, arylcarbonyloxy, arylcarbonylalkoxy, arylsulfonyloxy, arylalkoxy, arylalkylthio, arylalkylsulfinyl, arylalkylsulfonyl or linked via nitrogenlyllyl,

R ^{3 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl or cycloalkyl, R ^{4 represents} hydrogen or optionally substituted

Alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, and R ^{5 represents} hydroxyl, formyloxy, or optionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy,

Alkynyloxy, arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulfonyloxy.

2. Compounds of formula (I) according to claim 1, in which ^' n represents the numbers 0 or 2,

R represents optionally cyano-, halogen-, C ₁ -C ₄ -alkoxy, C ₄ - alkylthio, Cι-C ₄ - alkylsulfinyl or C ₄ -alkylsulfonyl-substituted alkyl having 1 to 6 carbon atoms, represents optionally cyano- or halogen-substituted Alkenyl or alkynyl each having 2 to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or dC-alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by Nitro, cyano, halogen, d-

C -alkyl, dd-haloalkyl, -CC ₄ -alkoxy or -CC -halo alkoxy-substituted aryl or arylalkyl, each with 6 or 10

Carbon atoms in the aryl group and optionally 1 to 4

Carbon atoms in the alkyl part,

X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for each optionally by cyano, halogen, d-

C ₄ -alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfmyl or C1-C4-alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl each having 1 to 6 carbon atoms in the alkyl groups, m for the numbers 0, 1, 2 or 3,

R ¹ for hydrogen, halogen, each optionally substituted by cyano, halogen, dC ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl substituted alkyl or alkylthio each with 1 to 6 carbon atoms, or for phenyl, or - if m is 2 or 3 - optionally together with a second

R ^{1 is} oxygen or alkanediyl (alkylene) having 3 to 5 carbon atoms, R ^{2 is} hydroxyl, formyloxy, halogen, each optionally by cyano, halogen, dC ₄ alkoxy, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ - alkylthio, dC ₄ alkylsulfinyl or C _r

C - alkylsulfonyl-substituted alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms, for each optionally substituted by halogen, alkenyloxy or alkynyloxy each having 3 to 6 carbon atoms, each in each case optionally by nitro, cyano, Halogen, dC - alkyl, dC -haloalkyl, -C-C ₄ alkoxy, dC ₄ -haloalkoxy, Cι-C ₄ - alkyl hio, C ₁ -C ₄ -haloalkylthio, dC ₄ - alkylsulfinyl, C _r C ₄ - haloalkylsulfinyl, C 1 -C ₄ alkylsulfonyl or C 1 -C ₄ haloalkyl sulfonyl substituted aryloxy, arylthio, arylsulfinyl, arylsulfonyl, Arylcarbonyloxy, arylcarbonylalkoxy, arylsulfonyloxy, arylalkoxy, arylalkylthio, arylalkylsulfmyl or arylalkylsulfonyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part or for pyrrolyl, pyrazolyl, imidazolyl bonded via nitrogen,

Triazolyl, tetrazolyl, R ^{3 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, each optionally substituted by cyano, halogen, -C-C ₄ alkoxy, d- C ₄ alkylthio, dC ₄ - alkylsulfinyl or dC - alkylsulfonyl substituted ized alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or

Alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups, or cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or dC ₄ alkyl, R ^{4 is} hydrogen, optionally substituted by cyano, halogen, dC ₄ alkoxy , dC - alkylthio, -C-C ₄ - alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl substituted alkyl having 1 to 6 carbon atoms, for each optionally substituted by cyano or halogen substituted alkenyl or alkynyl each having 3 to 6 carbon atoms, each optionally substituted by cyano , Halogen or dC-alkyl substituted cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, or for in each case optionally by nitro, cyano, halogen, dC ₄ -alkyl,

-C-C ₄ haloalkyl, dC ₄ -alkoxy, C ₁ -C ₄ -haloalkoxy, Cι-C ₄ - alkylthio, Cι-C ₄ -haloalkylthio, dC ₄ -alkylsulfinyl, dC ₄ - haloalkylsulfinyl, Cι-C ₄ -alkylsulfonyl or dC ₄ -haloalkyl-sulfonyl-substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4

Carbon atoms in the alkyl part, R ⁵ for hydroxy, formyloxy, for alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy, each with 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by cyano, halogen or C ₄ -C alkoxy, for each optionally by cyano or halogen substituted

Alkenyloxy or alkynyloxy having in each case 3 to 6 carbon atoms, or represents in each case optionally substituted by nitro, cyano, halogen, C ₄ - alkyl, dC ₄ haloalkyl, Cι-C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, dC -

Alkylthio, _{Cι-C4-haloalkylthio,} Cι-C ₄ -Alkylsulfmyl, dC - haloalkylsulfinyl, Cι-C ₄ - alkylsulfonyl or C ₄ haloalkyl sulfonyl substituted arylalkoxy, arylcarbonyloxy, arylcarbonyl alkoxy or arylsulfonyloxy having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the

Alkyl part stands.

3. Compounds of formula (I) according to claim 1, in which

n stands for the number 2,

R for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, n- or i-propylsulfmyl, methylsulfonyl, ethylsulfonyl and / or n- or i-Propylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, each optionally by Cyano, fluorine, chlorine and / or bromine-substituted ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl,

Ethyl and / or n- or i-propyl substituted cyclopropyl, cyclo- butyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylethyl, cyclopentylmethyl or cyclohexylmethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy and / or trifluoromethoxy substituted phenyl, naphthyl, phenylmethyl, phenylethyl or phenylpropyl, X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl , Fluorine, chlorine, bromine, iodine, or for each optionally by cyano, fluorine, chlorine, methoxy,

Ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl 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, methylsulfinyl, ethylsulfmyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl , n- or i-Propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulfonyl or diethylaminosulfonyl, m represents the numbers 0, 1 or 2 .

R ^{1 represents} hydrogen, fluorine, chlorine or bromine, each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl _, substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, or for phenyl, or - if m is 2 - optionally together with a second radical R ^{1 is} oxygen, propane-1,3-diyl or butane-1,4-diyl, R ^{2 is} hydroxy, Formyloxy, fluorine or chlorine, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, ethoxycarbonyloxy, ethoxycarbonyloxy, or i-propoxycarbonyloxy, methylammocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, for propenyloxy, butenyloxy, propynyloxy or butynyloxy, each optionally substituted by fluorine, chlorine and / or bromine each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,

Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfmyl, trifluoromethylsulfmyl, methylsulfonyl or trifluoromethylsulfonyl, Phenylthio, Phenylsulfinyl, Phenylsulfonyl, Phenylcarbonyloxy, Phenylcarbonyhnethoxy, Phenylsulfonyloxy, Phenylmethoxy, Phenylmethylthio, Phenylmethylsulfinyl or Phenylmethylsulfonyl or stands for Pyrazolyl bound via nitrogen, Imidazolyl, Triazolyl, for hydrogen, chloroyl, cyano, carboyl, cyano, cyano, cyano, chloroyl, cyano

Bromine, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,

Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i- Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, R ⁴ for hydrogen, for each methyl, ethyl, n- or i- substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl or ethylsulfonyl Propyl, n-, i-, s- or t-butyl, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by cyano, fluorine, chlorine and / or bromine, for each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, _cyclohexyl. Cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy , Ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, trifluoromethylsulfmyl, methylsulfonyl or trifluoromethylsulfonyl R ^{5 represents} hydroxyl, formyloxy, methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or i- each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy Butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylammocarbonyloxy, ethylaminocarbonyloxy, n- or i-propyl- aminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, for propenyloxy, butenyloxy, propynyloxy or butynyloxy, each optionally substituted by cyano, fluorine, chlorine and / or bromine, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i- Propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted phenylmethoxy, phenylcarbonyloxy, phenylcarbonylmethoxy or phenylsulfonyloxy.

Compounds of formula (I) according to claim 1, wherein

R stands for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, each optionally substituted by fluorine and / or chlorine, for cyclopropyl, cyclopentyl or cyclohexyl, each optionally substituted by fluorine, chlorine or methyl , or represents phenyl or phenylmethyl, X which is optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy for nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine,

Bromine, iodine, or for methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, optionally substituted by fluorine, chlorine, methoxy, ethoxy, methylthio ^" , ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl and / or ethylsulfonyl,

Ethylsulfonyl, dimethylamino or dimethylaminosulfonyl, m stands for the number 0, R ¹ stands for hydrogen, each optionally substituted by fluorine or chlorine

Methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, or for phenyl, or - if m is 2

- optionally together with a second radical R ¹ for oxygen, propane-1, 3-diyl or butane-1,4-diyl, R ² stands for hydroxy, -. , for methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propyl hio, acetyloxy, propionyloxy, n- or i, each optionally substituted by fluorine or chlorine -Butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylammocarbonyloxy, ethylammocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, each optionally substituted by fluorine, chlorine and / or bromine, / or bromine, / or bromine Butenyloxy, propynyloxy or butynyloxy, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, Ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted Ph enyloxy, phenylthio, phenylcarbonyloxy, phenylcarbonylmethoxy, phenylsulfonyloxy, phenylmethoxy or phenylmethylthio or for pyrazolyl or imidazolyl bonded via nitrogen, R ³ stands for hydrogen, fluorine, chlorine, bromine, for methyl, ethyl, n- which is optionally substituted by fluorine or chlorine, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,

Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethyl sulfmyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or for cyclopropyl optionally substituted by fluorine, chlorine or methyl, R ⁴ represents hydrogen, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for propenyl, butenyl, propynyl or butynyl, optionally substituted by fluorine, chlorine and / or bromine, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopenthenethyl or cyclohexylmethyl, each optionally substituted by fluorine, chlorine or methyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine,

Methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfmethylsulfonyl, trifluoromethyl , Ethylsulfonyl or trifluoromethylsulfonyl substituted phenyl or

Phenylmethyl, R ⁵ stands for hydroxy, for methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyl, which are optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy - oxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylammocarbonyloxy, ethylammocarbonyloxy, n- or i-propylamino-carbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, each optionally substituted by fluorine, chlorine and / or bromine Propenyloxy, butenyloxy, propynyloxy or butynyloxy, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i Propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl,

Ethylsulfonyl or trifluoromethylsulfonyl substituted phenylmethoxy, phenylcarbonyloxy, phenylcarbonylmethoxy or phenylsulfonyloxy.

A process for the preparation of compounds of formula (I) according to claim

1, characterized in that compounds of the formula (II),

in which n, R and X have the meaning given in claim 1 - or reactive derivatives thereof, such as, for example, corresponding acid halides, acid cyanides or esters -

with compounds of the general formula (III),

H-Z (III)

in which

Z has the meaning given in claim 1,

if appropriate in the presence of a dehydrating agent and if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents, and, if appropriate, after carrying out the process according to the invention on the compounds of the general formula (I) thus obtained, carrying out subsequent reactions for conversion into other compounds of the general formula (I).

Compounds of the formula (II),

in which

X represents CF ₃ , n and R have the meanings given in claim 1.

Compounds of the formula (VI)

in which

X stands for CF ₃ ,

R ^{6 represents} alkyl, benzyl or allyl, and

R has the meanings given in claim 1.

Agent characterized by a content of at least one compound of the formula (I) according to one of Claims 1 to 4.

9. Use of compounds of formula (I) according to one of claims 1 to 4 or of agents according to claim 8 for controlling unwanted plants.

10. A method for controlling unwanted plants, characterized in that at least one compound of the formula (I) according to one of claims 1 to 4 or agent according to claim 8 is allowed to act on undesired plants and / or their habitat.

11. Use of compounds of formula (I) according to claim 1 for

Manufacture of pesticides.

12. A process for the preparation of compounds of the formula (II) according to claim 6, characterized in that compounds of the formula (IV),

in which

X has the meaning given in claim 1,

R ^{6 represents} alkyl, benzyl or allyl, and X ^{1 represents} halogen,

with mercapto compounds of the general formula (N),

HS-R (V) in which

R has the meaning given in claim 1, - or with alkali metal salts of compounds of the formula (V) -

if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents, and if appropriate the carboxylic acid esters of the general formula (NI) thus obtained,

in which

R, R and X have the meanings given above,

with oxygenating agents, if appropriate in the presence of one or more ner thinners, and the esters thus obtained are converted into the compounds of the formula (II) by customary methods.