EP0968188A1 - Substituted 2-benz(o)ylpyridines, their preparation and their use as herbicides - Google Patents

Abstract

Substituted 2-benz(o)ylpyridines of formula (I) and the salts thereof, wherein n = 0, 1; x = CO, CH2, CH(C1-C4-alkyl), CH-OH, CH-CN, CH-halogen, C(halogen)2, CH-CONH2, CH-CO-O(C1-C4-alkyl), CH-O(C1-C4-alkyl), C(CN) (C1-C4-alkyl); R<1> = halogen, C1-C4-halogen alkane, C1-C4-alkylthio, C1-C4-alkyl sulfinyl, C1-C4-alkyl sulfonyl; R<2> = H, halogen; R<3> = H, NO2, OH, halogen, C1-C4-alkoxy; R<4> = H, NO2, OH, halogen, C1-C4-alkyl, C1-C4 halogen alkane, C1-C4-alkoxy; R<5> = H, NO2, CN, halogen, C1-C8-alkyl, C3-C8-alkenyl,C3-C8-alkinyl, C3-C8-cycloalkyl, C1-C8-halogen alkane, C2-C8-halogen alkenyl, C2-C8-halogen alkane, C1-C4-alkoxy-C1-C4-alkyl, C2-C4-alkenyloxy-C1-C4-alkyl, C2-C4-alkinyloxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl, cyano-C1-C8-alkyl, cyano-C2-C8-alkenyl, cyano-C3-C8-alkinyl, optionally substituted OH, SH, SO-H, -SO2-H, COOH or NH-COOH, -SO2Cl, -N(R<9>, R<10>), -NH-SO2-(C1-C8-alkyl), -N[-SO2-(C1-C8-alkyl)]2, -N(C1-C8-alkyl) [-SO2-(C1-C8-alkyl)], -SO2-N(R<9>, R<10>), -O-CO-NH-R<9>, optionally substituted CHO, -O-CHO or -NH-CHO, NH-CO-NH-R<9>, -O-CS-NH2, -OCS-N(C1-C8-alkyl)2, -CO-N(R<9>, R<10>), -CS-N (R<9>, R<10>), -CO-NH-SO2-(C1-C4-alkyl), -CO-N(C1-C4-alkyl), -SO2-(C1-C4-alkyl), hydroxycarbonyl-C1-C8-alkyl, (C1-C8-alkoxy)carbonyl-C1-C6-alkyl, -CH2-CH(halogen)-CO-N(R<9>, R<10>), -CH2-CH(halogen)-CN, -CH2-CH(halogen)-CO-(C1-C4-alkyl), optionally substituted -CH2-CH(halogen-COOH, -CH=C(halogen)-COOH or -CH=C(C1-C4-alkyl)-COOH, optionally substituted -CH=N-OH or -CH(-Y-R<15>, -Z-R<15>), (II) or (III); R<9>, R<10> = H, C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, C3-C8-alkinyl, C1-C8-halogen alkane, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl, cyano-C1-C8-alkyl, hydroxycarbonyl-C1-C4-alkyl, (C1-C4-alkoxy)carbonyl-C1-C4-alkyl, (C3-C6-cycloalkoxy)carbonyl-C1-C4-alkyl, (C1-C4-alkoxy)carbonyl-C3-C7-cycloalkyl, C1-C4-alkoxy-(C1-C4)alkoxy)-carbonyl-C1-C4-alkyl, C1-C6-alkoxy, optionally substituted phenyl or phenyl-C1-C4-alkyl or R<9> + R<10> together = optionally substituted tetramethylene, pentamethylene or ethylene oxyethylene chain; Y, Z = O, S; R<15> = C1-C8-alkyl, C1-C8 halogen alkane, C1-C4-alkoxy-C1-C4-alkyl; R<16>-R<21> = H, CN, C1-C8-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy, COOH, (C1-C8-alkoxy)carbonyl, CONH2, (C1-C8-alkyl)aminocarbonyl, di(C1-C8-alkyl)aminocarbonyl; R<6> = H, NO2, halogen, optionally substituted OH or COOH; R<7> = H, NO2, halogen, optionally substituted OH; excluding those compounds in (I) in wherein X = CH2 and R<5> = optionally substituted OH as well as R<3>, R<7> = H or R<1> = halogen as well as R<3>, R<4>, R<6>, R<7> = H. The invention further relates to the use of said substances as herbicides and for dessication/defoliation of plants.

Description

SUBSTITUTED 2-BENZ (0) YLPYRIDINE DERIVATIVES, THEIR PRODUCTION AND THEIR USE AS HERBICIDES

description

The present invention relates to new substituted 2-benz (o) ylpyridines of the formula I.

in which the variables have the following meanings:

n 0 or 1;

X carbonyl, methylene, CH (C ₁ -C ₄ alkyl), CH-OH, CH-CN, CH-halogen, C (halogen) ₂ , CH-CONH ₂ , CH-CO-0 (Cι-C ₄ - Alkyl), CH-0 (C ₁ -C ₄ alkyl) or C (CN) (C ₁ -C ₄ alkyl);

R ¹ halogen, C ¹ -C ₄ haloalkyl, C1-C ₄ alkylthio, C 1 -C ₄ alkyl sulfinyl or C 1 -C ₄ alkyl sulfonyl;

R ^{2 is} hydrogen or halogen;

R ^{3 is} hydrogen, nitro, hydroxy, halogen or -CC ₄ alkoxy;

R ^{4 is} hydrogen, nitro, hydroxy, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ alkoxy;

R ^{5 is} hydrogen, nitro, cyano, halogen, -CC ₈ alkyl,

C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, C ₃ -C ₈ cycloalkyl, d -C ₈ haloalkyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ haloalkynyl,

Ci -C ₄ alkoxy-Ci -C ₄ alkyl, C ₂ -C ₄ alkenyloxy Ci -C alkyl, C ₂ -C ₄ alkynyloxy Ci Ci ₄ alkyl, Ci -C ₄ alkylthio Ci -C ₄ - alkyl, _{Cι-C4-alkylsulfinyl-Cι-C 4} - lkyl, Cι-C ₄ alkylsulfonyl-Cι-C ₄ - alkyl, cyano -Cι-C ₈ - alkyl, cyano C ₂ -C _8- alkenyl, cyano -C ₃ -C ₈ -alkynyl, -OR ⁸ , -SR ⁸ , -SO-R ⁸ , -S0 ₂ -R ⁸ , -S0C1, -N (R9, R «), -NH- S0 ₂ - (Ci-Cβ-Al yl), -N [-S0 ₂ - (-Cι-C _β- alkyl)] ₂ , -N (Cι-C ₈ -alkyl) [-S0 ₂ - (Ci-Cβ- Alkyl)], - S0 ₂ -N (R ⁹ , R "), -NCR ¹¹ ) -CO-R ¹² , -NH-CO-OR ⁸ , -0-CO-NH-R ⁹ , -O-CO- R ¹² , -NH-CO-NH-R ⁹ , -0-CS-NH ₂ , -0-CS-N (C ₁ -C ₈ alkyl) ₂ , -CO-OR ⁸ , -CO-N (R ⁹ , R ¹ °), -CS-N (R ⁹ , R "), -CO-NH-S0 ₂ - (C ₁ -C ₄ -alkyl), -CO-N (-C-C-alkyl) -S0 ₂ - (-C-C ₄ alkyl), -CO-R ¹² , hydroxy carbonyl -Ci -C ₈ alkyl, (Ci -C ₈ alkoxy) carbonyl -Ci - C ₆ alkyl, -CH ₂ -CH (halogen) -CO-OR ⁸ , -CH -CH (halogen) -CO-N (R ⁹ , R ¹⁰ ),

-CH ₂ -CH (halogen) -CN, -CH ₂ -CH (halogen) -C0- (C ₁ -C ₄ alkyl),

-CH = C (halogen) -CO-OR ⁸ , -CH = C (C ₁ -C ₄ alkyl) -CO-OR ⁸ , -CH = N-OR ¹³ ,

-C (R ¹ ) = N-OR ¹³ , -CH (-YR ¹⁵ , -ZR ¹⁵ ), -C (R ¹⁴ ) (- YR ¹⁵ , -ZR ¹⁵ ),

in which

for hydrogen, -CC ₈ -alkyl, C ₃ -C ₈ -cycloalkyl, -C-C ₈ -halo-alkyl, cyano -C-C ₈ -alkyl, C ₁ -C ₄ -alkoxy- C ₁ -C ₄ - alkyl, Ci - C ₄ alkyl thio - Ci - C ₄ - alkyl, Ci - C ₄ - alkylsulfonyl - Ci - C - alkyl, C ₁ -C ₄ alkylsulfonyl -CC-C ₄ - alkyl, C ₃ - C ₈ alkenyl, C ₅ -C ₈ cycloalkenyl, C ₃ -C ₈ haloalkenyl, C ₃ -C ₈ alkynyl, hydroxycarbonyl - Ci - C ₄ - alkyl, (Ci - C ₈ alkoxy) carbonyl - Ci - C ₆ - alkyl, (C ₃ -C ₈ alkenyloxy) carbonyl -Ci-C _δ- alkyl, (C -C ₈ -alkynyloxy) - carbonyl -Cι-C ₆ - alkyl, Cι-C ₄ - Alkoxy- (C ₃ -C ₄ -alkoxy) carbonyl -CC-C ₄ -alkyl, (-C-C ₈ -halogenalkoxy) carbonyl -CC-C ₆ -alkyl,

(C ₃ -C ₈ -cycloalkyloxy) carbonyl-Cι-C ₆ -alkyl, (C ₁ -C ₄ alkoxy) - carbonyl- (Cι-C ₄ - alkoxy) carbonyl -Cχ-C ₄ alkyl, (C ₃ -C ₆ alkenyloxy) carbonyl - (Ci - C - alkoxy) carbonyl - Ci - C ₄ - alkyl, (C ₃ - C6 - alkynyloxy) carbonyl - (Ci -C ₄ - alkoxy) carbonyl - Ci - C ₄ - alkyl, hydroxycarbonyl - (C ₁ -C ₄ - alkoxy) carbonyl -CC-C - alkyl, oxetan-3-yloxycarbonyl - C - C ₄ - alkyl,

Phenoxycarbony 1 - Ci - C ₄ alkyl, benzyl or benzyloxycarbonyl - C ₁ -C4 alkyl, where the phenyl rings of the 3 last-mentioned radicals can each be unsubstituted or can carry one to three substituents, each selected from the group consisting of nitro, cyano, hydroxy, hydroxycarbonyl, halogen, Cι-C ₄ -alkyl, C ₄ haloalkyl, Ci -C ₄ alkoxy, C ₁ -C ₄ -halo - alkoxy, (C ₁ -C ₄ alkoxy) carbonyl, and (C -C ₄ alkoxy) carbonyl - C1-C4 alkoxy;

CH (R ²² ) CO N (R ⁹ , R ¹⁰ ), CH (R ²² ) CO R ²³ CH (R ²² ) CR ²³ , CH (R ²² ) CO CO OR ²³ ,

N OR ¹³

II CH (R ²² ) C CO OR ²³ ,

CH (R ²² ) CO N OR ²⁵

CH (R ²² ) CO OR ²³ CH (R ²² ) COCH (R ²² ) CO OR ²³

II

N OR ²⁵

R ⁹ , R ¹⁰ independently of one another for hydrogen, -CC ₈ alkyl,

C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, _{Cι-C8-halo-alkyl,} Ci _-C4 alkoxy-Cι-C ₄ - alkyl, Cι-C _{alkylthio-Cι-C4} alkyl, _Ci-C4 alkylsulfinyl -C -C - alkyl, _Ci-C4 alkylsulfonyl - Ci -C ₄ - alkyl, cyano -Cχ-C ₈ alkyl, hydroxycarbonyl ₁ -C -C ₄ -alkyl, (-C-C ₄ -alkoxy) carbonyl -Cχ-C - alkyl, (C ₃ -C -cycloalkyloxy) - carbonyl -Ci -C ₄ - alkyl, (Ci -C ₄ -alkoxy) carbonyl - C ₃ -C -cycloalkyl, -C-C ₄ -alkoxy- (C ₁ -C ₄ - alkoxy) carbonyl -C ₁ -C ₄ -alkyl, Cι-C ₆ -alkoxy, phenyl or phenyl -C ₁ -C ₄ - alkyl, where the phenyl rings of the last two radicals can be unsubstituted or can carry one to three substituents, each selected from the group consisting of nitro, cyano, hydroxy, halogen, Cχ-C ₄ haloalkyl, C 1 -C ₄ alkoxy, C 1 -C ₄ -haloalkoxy,

' ₁ -C ₄ alkoxy) carbonyl and (Ci -C ₄ alkoxy) carbonyl -C ₁ -C ₄ alkoxy

or R ⁹ and R ¹⁰ together for a tetramethylene, pentamethylene or ethyleneoxyethylene chain, each of which can carry a hydroxycarbonyl group or a (-C ₆ alkoxy) carbonyl radical;

R ^{11 represents} hydrogen, -CC ₈ alkyl, C ₃ -C ₈ alkenyl or C ₃ -C ₈ alkynyl; R ¹² , R ¹³ independently of one another for hydrogen, -CC ₈ alkyl,

C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, -C-C ₈ haloalkyl, C ₁ -C ₄ alkoxy- C ₁ -C ₄ alkyl, (C ₁ -C ₄ alkoxy) carbonyl - ^ -C- alkyl, C ₃ -C ₈ cycloalkyl, phenyl or phenyl -C ₁ -C ₄ alkyl, where the phenyl rings of the last two radicals can be unsubstituted or can carry one to three substituents, each selected from the group consisting from nitro, cyano, hydroxy, hydroxycarbonyl, halogen, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, Ci -C ₄ haloalkoxy, (C ₁ -C ₄ alkoxy) carbonyl and (C ₁ -C ₄ alkoxy) carbonyl - Ci-C ₄ alkoxy;

R ^{14 is} Ci -C ₈ alkyl;

Y, Z independently of one another for oxygen or sulfur;

R ¹⁵ for -CC ₈ alkyl, -C-C ₈ haloalkyl or Ci -C ₄ alkoxy- Ci-C -alkyl;

_R i6. _R 2i are independently hydrogen, cyano, C ₈ alkyl, C - C alkoxy-C ₁ -C ₄ - alkyl, Cι-C ₈ alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ - Alkoxy, hydroxycarbonyl, (-CC ₈ alkoxy) carbonyl, amino-carbonyl, (C 1 -C ₈ -alkyl) aminocarbonyl or di (-C ₈ -alkyl) - a inocarbonyl;

R ²² -R ²⁵ independently of one another for hydrogen, -CC ₈ alkyl,

Ci -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₃ -C ₈ alkenyl or C ₃ -C ₈ alkynyl

and

_R 26. _R 28 independently represent hydrogen or Cx-Cs-alkyl;

R ^{6 is} hydrogen, nitro, halogen, -OR ²⁹ or -CO-OR ²⁹ and R ^{7 is} hydrogen, nitro, halogen or -OR ³⁰ , where R ²⁹ and R ³⁰ each represent one of the meanings of R ⁸ ,

and the agriculturally useful salts of the compounds I, with the exception of those compounds I in which X is methylene, and

R ^{5 is} -OR ⁸ and R ³ and R ^{7 are} both hydrogen or R ^{1 is} halogen and R ³ , R ⁴ , R ⁶ and R ^{7 are} all hydrogen at the same time. The invention also relates to the use of the compounds I as herbicides or for

Desiccation / defoliation of plants, herbicidal agents and agents for desiccation and / or defoliation of plants which contain the compounds I as active substances,

Process for combating undesirable plant growth and for desiccating and / or defoliation of plants with the

Compounds I and - Process for the preparation of the compounds I and herbicidal agents and agents for desiccation and / or

Defoliation of Plants Using Compounds I.

EP-A 047 972 describes phenoxyalkanoic acid derivatives for increasing the carbohydrate incorporation in plants, the general formula of which - with a suitable choice of the variables - also compounds I with n = 0, X = methylene, R ¹ = halogen, di- or tri fluoromethyl, R ² = fluorine or chlorine, R ³ , R ⁴ , R ⁶ and R ⁷ = hydrogen and R ⁵ = ethoxy, 2-butoxy or but-3-en-2-yloxy, each substituted by a hydroxycarbonyl, certain ester, thioester or acid amide residue.

Those 2-benzylpyridines I with n = 0, X = methylene, R ¹ = halogen or trifluoroethyl, R ³ , R ⁴ and R ⁷ = hydrogen, R ⁵ = ethoxy, 2-butoxy or but-3-en-2- yloxy, each carrying a certain acid amide group, and R ⁶ = hydrogen or halogen fall under the general formula of compounds taught in DE-A 29 48 095 as herbicides and fungicides.

From the Swiss patent CH 642 075 a compound with n = 0, X = methylene, R ¹ = chlorine, R ² = hydrogen, R ³ , R ⁴ , R ⁶ and R ⁷ = hydrogen and R ⁵ = 2- (ethoxycarbonyl ) but-2-yloxy known, which is attributed to a pharmaceutical effect.

Benz (o) ylpyridines of the type of the compounds I also fall under the general formulas of herbicides described in WO 92/22203, EP-A 078 536 and EP-A 461 079.

From T. Asami et al., Biosci. Biotech. Biochem. 57 (2), 350/351 (1993) are the two benzylpyridines

with R ^a = H (No. 20) or OC ₂ Hs (No. 21) known as a photosynthesis inhibitor.

Finally, certain 3-benzoylpyridines are taught as herbicides in WO 96/17829.

Since the herbicidal properties of the above Not always completely satisfying herbicides with regard to the harmful plants, the present invention was based on new herbicidally active compounds as tasks with which undesired plants can be controlled more effectively than before. The task also extended to the provision of new desiccant / defoliant connections.

Accordingly, the present substituted 2-benz (o) yl pyridines of the formula I and their herbicidal activity have been found.

Furthermore, herbicidal compositions have been found which contain the compounds I and have a very good herbicidal action. In addition, processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.

Furthermore, it has been found that the compounds I are also suitable for the desiccation / defoliation of parts of plants, for which crop plants such as cotton, potatoes, rapeseed, sunflower, soybeans or field beans, in particular cotton, are suitable. In this regard, agents for the desiccation and / or defoliation of plants, methods for producing these agents and methods for the desiccation and / or defoliation of plants with the compounds I have been found.

Depending on the substitution pattern, the compounds of the formula I can contain one or more centers of chirality and are then present as mixtures of enantiomers or diastereomers. E / Z isomers are also possible if at least one substituent with a double bond is present. The invention relates both to the pure enantiomers or diastereomers and to their mixtures.

Agriculturally usable salts are to be understood in particular as the salts of I with those cations and acid addition salts of I with those acids which do not adversely affect the herbicidal or desiccant / defoliant effect of I. So come as cations in particular the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, which has a C 1 -C ₄ Alkyl, phenyl or benzyl substituents and, if desired, can additionally carry one to three further C 1 -C ₄ -alkyl radicals, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, preferably tri- (C 1 -C ₄ -alkyl) - Phosphonium, sulfonium ions, preferably tri- (C 1 -C ₄ alkyl) sulfonium, and sulfoxonium ions, preferably tri- (C 1 -C ₄ alkyl) sulfoxonium.

Anions of useful acid addition salts are phosphate primarily fluoride, chloride, bromide, hydrogen sulfate, sulfate, dihydrogen, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, oxalate, dodecylbenzenesulfonate, and the anions of _C1-C4 -Alkanoic acids, preferably for iate, acetate, propionate and butyrate.

The organic molecule parts mentioned for the substituents R ¹ , R ³ , R ⁴ , R ⁵ and R ⁸ to R ³⁰ or as residues on phenyl rings are collective terms for individual enumeration of the individual group members. All carbon chains, that is to say all alkyl, haloalkyl, Cyanoalkyl, oxetanyloxycarbonylalkyl, hydroxycarbonylalkyl, phenylalkyl, phenoxycarbonylalkyl, benzyloxycarbonylalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, haloalkenyl, cyanoalkenyl, alkenyloxy, alkynyl Haloalkynyl, cyanoalkynyl and alkynyloxy parts can be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms.

Halogen is fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.

Furthermore, for example:

C ₁ -C ₄ alkyl for: CH ₃ , C ₂ H ₅ , CH ₂ -C ₂ H ₅ , CH (CH ₃ ) ₂ , nC ₄ H ₉ , CH (CH ₃ ) -C ₂ H ₅ , CH ₂ -CH (CH ₃ ) ₂ or C (CH ₃ ) ₃ , especially for CH ₃ or C ₂ H ₅ ;

C ₁ -C ₄ -haloalkyl: a Cι ~ C ₄ alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, eg CH ₂ F, CHF, CF _3, CH ₂ C1, CH (C1) ₂ , C (C1) ₃ , chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, CH ₂ -CHF ₂ , CH ₂ -CF ₃ , 2-chloro-2-fluoroethyl,

2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl,

2,2, 2-trichloroethyl, C ₂ F ₅ , 2-fluoropropyl, 3-fluoropropyl,

2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl,

3, 3, 3-trifluoropropyl, 3, 3, 3-trichloropropyl, CH ₂ -C ₂ F ₅ , CF ₂ -C ₂ F ₅ , 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2- chloroethyl, 1- (bromomethyl) -2-bromethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl, in particular for CH ₂ F, CHF ₂ , CF ₃ , CH ₂ C1, 2-fluoroethyl, 2-chloroethyl or CH ₂ -CF ₃ ;

Cι ~ C ₈ alkyl for: C ₁ -C ₄ alkyl as mentioned above, or for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl , 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl , 2, 2-Dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dirne hylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1, 2-trimethylpropyl, 1, 2, 2-trimethylpropyl, 1-ethyl- l-methylpropyl or l-ethyl-2-methylpropyl, in particular for CH ₃ , C ₂ H ₅ , CH ₂ -C ₂ H ₅ , CH (CH ₃ ) ₂ , n-butyl, C (CH ₃ ) ₃ , n- Pentyl or n-hexyl;

- Cι-C ₈ -haloalkyl: a Cι-C ₈ -alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine residues so-called, for example, one of the under Cι-C ₄ haloalkyl, or for 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, decafluoropentyl, 6-fluoro-l-hexyl, 6-chloro-1-hexyl, 6-bromo-l-hexyl, 6-iodo-l-hexyl, 6, 6, 6-trichloro-1-hexyl or dodecafluorohexyl, in particular for CH ₂ F, CHF ₂ , CF ₃ , CH ₂ C1, 2-fluoroethyl, 2-chloroethyl or CH ₂ -CF ₃ ;

- Cyano-Cι-C ₈ alkyl for: for example CH ₂ CN, 1-cyanoeth-l-yl, 2-cyano-eth-l-yl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyanoprop-1-yl, l-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-l-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4- Cyanobut-l-yl, 1-cyano-but-2-yl, 2-cyanobut-2-yl, 3-cyanobut-2-yl, 4-cyanobut-2-yl, l-cyano-2-methyl-prop- 3-yl, 2-cyano-2-methyl-prop-3-yl,

3-cyano-2-methyl-prop-3-yl, 2- (CH ₂ CN) -prop-2-yl or 2-cyano-hex-6 -yl, in particular for CH CN or 2-cyanoethyl;

Oxetan- 3 -yloxycarbonyl -CC ₄ ~ alkyl for: z. B. oxetane-3 -yloxycarbonylmethyl, 2- (oxetane-3 -yloxycarbonyl) ethyl, 2- (oxetane

3 -yloxycarbonyl) prop-l-yl, 3- (oxetane-3 -yloxycarbonyl) prop-1-yl, 2- (oxetan-3 -yloxycarbonyl) but-l-yl, 3- (oxetane-3 -yloxy- carbonyl) but-1-y1, 4- (oxetan-3-yloxycarbonyl) but-1-y1, 1- (oxetan-3-yloxycarbonyl) but-2-yl, 3- (oxetan-3-yloxycarbonyl) but -2-y1, 4- (oxetan-3-yloxycarbonyl) but-2-y1, 1- (oxetan-3-yloxycarbonylmethyl) -eth-l-yl, 1- (oxetan-3-yloxycarbonylmethyl) -l- (methyl) -eth-l-yl or 1- (oxetan- 3 -yloxycarbonylmethyl) prop-1-yl, especially for oxetan- 3 -yloxycarbonylmethyl or 2 - (oxetan- 3 -yloxycarbonyl) ethyl;

Hydroxycarbonyl -CC ₄ alkyl for: CH ₂ COOH, CH (CH ₃ ) COOH, 2- (COOH) ethyl, 1- (COOH) prop-l-yl, 2- (COOH) prop-1-yl,

3- (COOH) prop-l-yl, 1- (COOH) but-l-yl, 2- (COOH) but-l-yl, 3- (COOH) but-l-yl, 4- (COOH) but -l-yl, 1- (COOH) but-2-yl, 2- (COOH) but-2-yl, 3- (COOH) but-2-yl, 4- (COOH) but-2-yl, l - (CH ₂ COOH) eth-l-yl, 1- (CH ₂ COOH) -1- (CH ₃ ) -eth-l-yl or 1- (CH ₂ COOH) prop-l-yl, especially for CH ₂ COOH or 2- (COOH) ethyl;

Hydroxycarbonyl -Cι-C ₈ alkyl for: hydroxycarbonyl -C ₁ -C ₄ alkyl as mentioned above, and for example 5- (COOH) pent-l -yl or 6- (COOH) hex-1-yl;

Phenyl-Cι-C ₄ alkyl for: benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-l-yl, 1-phenylbut-l- yl, 2-phenylbut-l-yl, 3-phenylbut-l-yl, 4-phenylbut-l-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1- (phenylmethyl) - eth-l-yl, 1- (phenylmethyl) -1- (methyl) -eth-l-yl or 1- (phenylmethyl) prop-1-yl, especially for benzyl or 2-phenylethyl;

Phenoxycarbonyl-Cι ~ C ₄ alkyl for: phenoxycarbonyl-methyl, 1- (phenoxycarbonyl) ethyl, 2- (phenoxycarbonyl) ethyl, 1- (phenoxycarbonyl) rop-1-yl, 2- (phenoxycarbonyl) prop-1-yl, 3- (phenoxycarbonyl) prop-l-yl, 1- (phenoxycarbonyl) but-1-yl, 2- (phenoxycarbonyl) but-1-yl, 3- (phenoxycarbonyl) but-l-yl, 4- (phenoxycarbonyl) but -1-yl, 1- (phenoxycarbonyl) but-2-yl, 2- (phenoxycarbonyl) but-2-yl, 3- (phenoxycarbonyl) but-2-yl, 4- (phenoxycarbonyl) but-2-yl, 1 - (Phenoxycarbonyl-methyl) - eth-l-yl, 1- (phenoxycarbonyl-methyl) -l- (methyl) -eth-l-yl or 1- (phenoxycarbonyl-methyl) prop-1-yl, especially for phenoxycarbonyl -methyl or 2- (phenoxycarbonyl) ethyl;

Benzyloxycarbonyl-Cχ-C ₄ alkyl for: benzyloxycarbonyl-methyl, 1- (benzyloxycarbonyl) ethyl, 2- (benzyloxycarbonyl) ethyl, 1- (benzyloxycarbonyl) prop-l-yl, 2- (benzyloxycarbonyl) - prop-1-yl , 3- (benzyloxycarbonyl) prop-l-yl, 1- (benzyloxycarbonyl) but-l-yl, 2- (benzyloxycarbonyl) but-l-yl, 3- (benzyl- oxycarbonyl) but-1-yl, 4- (benzyloxycarbonyl) but-l-yl, 1- (benzyloxycarbonyl) but-2-yl, 2- (benzyloxycarbonyl) but-2-yl, 3- (benzyloxycarbonyl) but-2- yl, 4- (benzyloxycarbonyl) but-2-yl, 1- (benzyloxycarbonyl-methyl) -eth-l-yl, 1- (benzyloxycarbonyl-methyl) -l- (methyl) -eth-l-yl or 1- ( Benzyloxycarbonyl - methyl) prop-l-yl, especially for benzyloxycarbonylmethyl or 2- (benzyloxycarbonyl) ethyl;

Cι-C ₄ alkoxy for: OCH ₃ , OC ₂ H ₅ , n-propoxy, OCH (CH ₃ ) ₂ , n-butoxy, 1-methylpropoxy, OCH ₂ -CH (CH ₃ ) ₂ or OC (CH ₃ ) ₃ , especially for OCH ₃ or OC ₂ H ₅ ;

Ci-C _ö alkoxy for: a -CC ₄ alkoxy radical as mentioned above, or for example n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2, 2-dimethylpropoxy, 1-ethylpropoxy, n -Hexoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3 -Dimethylbutoxy, 2, 2-dimethylbutoxy, 2, 3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy,

1,2, 2-trimethylpropoxy, 1-ethyl-l-methylpropoxy or 1-ethyl-2-methylpropoxy, in particular for OCH ₃ , OC ₂ H ₅ , OCH ₂ -CH ₅ , OCH (CH ₃ ) ₂ , n-butoxy , OC (CH ₃ ) ₃ , n-pentoxy or n-hexoxy;

Cι-C ₈ -alkoxy: a Ci-C _ß alkoxy radical as mentioned above, or for example, 0 (n-CHιs) or 0 (nC ₈ Hι), in particular Ci-Cβ-alkoxy;

C 1 -C 6 -alkalkoxy for: a C 1 -C 4 alkoxy radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 0CH ₂ F, OCHF ₂ , 0CF ₃ , 0CH ₂ C1, OCH (CD ₂ , 0C (C1) ₃ , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, OCH ₂ -CHF ₂ , OCH ₂ -CF ₃ , 2 -Chlor-2-fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2,2-di-chloro-2-fluoroethoxy, 2,2, 2-trichloroethoxy, OC ₂ Fs, 2-fluoropropoxy, 3-fluoropropoxy , 2, 2-difluoropropoxy, 2, 3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2, 3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3, 3-tri-luorpropoxy, 3,3, 3-trichloropropoxy, OCH ₂ -C ₂ F ₅ , OCF ₂ -C ₂ F ₅ , 1- (fluoromethyl) -2-fluoroethoxy, 1- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2- bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nC ₄ F ₉ , in particular for 2 -chloroethoxy or OCH -CF ₃ ; (-C-C ₄ -alkoxy) carbonyl for: CO - OCH ₃ , CO - OC ₂ H ₅ , CO - OCH ₂ - C ₂ H ₅ ,

CO-OCH (CH ₃ ) ₂ , n-butoxycarbonyl, CO-OCH (CH ₃ ) -C ₂ H ₅ ,

CO-OCH ₂ -CH (CH ₃ ) ₂ or CO-OC (CH ₃ ) ₃ , especially for CO-OCH ₃ or CO-OC ₂ H ₅ , -

(-CC ₆ -alkoxy) carbonyl for: a (C ₁ -C ₄ -alkoxy) carbonyl radical as mentioned above, or for example (n-pentoxy) carbonyl,

1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, (n-hexoxy) carbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2 -Methylpentoxycarbony1, 3-methylpentoxycarbonyl, 4-methyl-pentoxycarbonyl, 1, 1-dimethylbutoxycarbonyl, 1, 2-dimethyl-butoxycarbonyl, 1, 3-dimethylbutoxycarbonyl, 2, 2-dimethyl-butoxycarbonyl, 2,3-dirnethylbutoxycarbony1, 3,3 -Dirnethyl - butoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1, 2-trirrtethylpropoxycarbonyl, 1,2, 2-trimethylpropoxycarbonyl, 1-ethyl-l-methylpropoxycarbonyl or l-ethyl-2-methylpropoxycarbonyl, especially for COOCH ₃ , COOC ₂ H ₅ , n-propoxycarbonyl, COOCH (CH ₃ ), n-butoxycarbonyl, COOC (CH ₃ ) ₃ , n-pentoxycarbonyl or n-hexoxycarbonyl;

(-C ₈ -alkoxy) carbonyl for: a (Cχ-C ₆ -alkoxy) carbonyl radical as mentioned above, or for example CO-0 (nC ₇ Hιs) or CO-0 (nC ₈ Hχ), in particular for ( Cχ-C ₆ alkoxy) carbonyl;

Cι-C ₄ alkylthio for: SCH ₃ , SC ₂ H ₅ , SCH ₂ -C ₂ H ₅ , SCH (CH ₃ ) ₂ , n-butylthio, SCH (CH ₃ ) -C ₂ H ₅ , SCH ₂ -CH (CH ₃ ) ₂ or SC (CH ₃ ) ₃ , especially for SCH ₃ or SC ₂ Hs;

C 1 -C ₄ -alkoxy-C ₄ -C ₄ -alkyl for: C ₄ -C ₄ -alkoxy as mentioned above-substituted C 1 -C ₄ -alkyl, for example for CH ₂ -OCH ₃ , CH ₂ -OC ₂ H ₅ , CH ₂ -0CH ₂ -C ₂ H ₅ , CH ₂ -OCH (CH ₃ ) ₂ , n-butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, CH ₂ -OC (CH ₃ ) ₂ , 2- (methoxy) ethyl, 2- (ethoxy) ethyl, 2- (n-propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methylpropoxy) ethyl, 2- (1, 1-dimethylethoxy) ethyl, 2- (methoxy) propyl, 2- (ethoxy) propyl, 2- (n-propoxy) propyl, 2- (1- Methyl ethoxy) propyl, 2- (n-butoxy) propyl, 2- (1-methylpropoxy) propyl, 2- (2-methylpropoxy) propyl, 2- (1, 1-dimethylethoxy) propyl, 3- (methoxy) propyl , 3- (Ethoxy) propyl, 3- (n-propoxy) propyl, 3- (1-methylethoxy) propyl, 3- (n-butoxy) propyl, 3- (l-methylprooxy) propyl, 3- (2nd -Methylpropoxy) propyl, 3- (1, 1-dimethylethoxy) propyl, 2- (methoxy) butyl, 2- (ethoxy) butyl, 2- (n-propoxy) butyl, 2- (1-methylethoxy) butyl, 2- (nB utoxy) butyl, 2- (1-methylpropoxy) utyl, 2- (2-methylpropoxy) butyl, 2- (1, 1-dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl, 3- (n-propoxy) butyl, 3- (1-methylethoxy) butyl, 3- (n-butoxy ) butyl, 3- (1-methylpropoxy) butyl, 3- (2-methylpropoxy) butyl, 3- (1, 1-dimethylethoxy) butyl, 4- (methoxy) butyl, 4- (ethoxy) butyl, 4- (n-propoxy) butyl, 4- (1-methylethoxy) butyl, 4- (n-butoxy) butyl, 4- (1-methylpropoxy) butyl, 4- (2-methylprooxy) butyl or 4- (1, 1-dimethylethoxy) butyl, especially for CH ₂ -OCH ₃ or 2-methoxyethyl;

C -C ₄ alkoxy-Cχ-C ₄ -alkoxy for: Cχ-C-alkoxy substituted by Cχ-C-alkoxy as mentioned above, for example for OCH ₂ -OCH ₃ , OCH ₂ -OC ₂ H ₅ , OCH ₂ -OCH ₂ -C ₂ H ₅ , OCH ₂ -OCH (CH ₃ ) ₂ , n-butoxy methoxy, (1-methylpropoxy) methoxy, (2-methylpropoxy) methoxy, OCH ₂ -OC (CH ₃ ) ₃ , 2 - (Methoxy) ethoxy, 2- (ethoxy) ethoxy, 2- (n-propoxy) ethoxy, 2- (1-methylethoxy) ethoxy, 2- (n-butoxy) ethoxy, 2- (1-methylpropoxy) ethoxy , 2- (2-methylpropoxy) ethoxy, 2- (1, 1-dimethylethoxy) ethoxy, 2- (methoxy) propoxy, 2- (ethoxy) propoxy, 2- (n-propoxy) propoxy, 2- (l-methyl - ethoxy) propoxy, 2- (n-butoxy) propoxy, 2- (l-methylpropoxy) propoxy, 2- (2-methylpropoxy) propoxy, 2- (1, 1-dimethylethoxy) propoxy, 3- ( Methoxy) propoxy, 3- (ethoxy) propoxy, 3- (n-propoxy) ropoxy, 3- (1-methylethoxy) propoxy, 3- (n-butoxy) propoxy, 3- (1-methylpropoxy) propoxy, 3- (2-methyl-propoxy) propoxy, 3- (1, 1-dimethyl-ethoxy) propoxy, 2- (methoxy) b toxy, 2- (ethoxy) butoxy, 2- (n-propoxy) butoxy, 2 - (l-methylethoxy) butoxy, 2- (n-butoxy) butoxy, 2- (l-methylprooxy) butoxy, 2- (2-methylpropoxy) utoxy, 2- (1, 1-dimethylethoxy) butoxy, 3- (methoxy) butoxy, 3- (ethoxy) butoxy, 3- (n-propoxy) butoxy, 3- (1-methylethoxy) butoxy, 3- (n-butoxy) butoxy, 3- (1-methylpropoxy) butoxy, 3- (2-methylpropoxy) butoxy, 3- (1, 1-dimethylethoxy) butoxy, 4- (methoxy) butoxy, 4- (ethoxy) butoxy, 4- (n-propoxy) butoxy, 4- (l -Methyl- ethoxy) butoxy, 4- (n-butoxy) butoxy, 4- (1-methylpropoxy) - butoxy, 4- (2-methylpropoxy) butoxy or 4- (1, 1-dirnethyl - ethoxy) butoxy, especially for OCH -OCH ₃ or 2 methoxy ethoxy;

(Cχ-C-alkoxy) carbonyl-Cχ-C ₄ -alkyl for: C (-C-alkyl substituted by (Cχ-C-alkoxy) carbonyl as mentioned above, for example for CH ₂ COOCH ₃ , CH ₂ COOC ₂ H ₅ , CH (CH ₃ ) COOCH ₃ or 2- (COOCH ₃ ) ethyl;

(Cχ-C ₈ -alkoxy) carbonyl -Cχ-C ₆ "alkyl for: C (-Cg-alkyl substituted by (Ci -C ₈ -alkoxy) carbonyl as mentioned above, for example for CH ₂ COOCH ₃ , CH ₂ COOC ₂ H ₅ , CH (CH ₃ ) COOCH ₃ , CH (CH ₃ ) COOC ₂ H ₅ , C (CH ₃ ) ₂ COOCH ₃ or C (CH ₃ ) ₂ COOC ₂ H ₅ ; Hydroxycarbonyl- (Cχ-C ₄ -alkoxy) carbonyl-Cχ-C ₄ -alkyl for:

(Cχ-C ₄ -alkoxy) carbonyl-Cχ-C ₄ -alkyl as mentioned above, which carries a hydroxycarbonyl group, for example for

CH ₂ -COOCH ₂ -COOH, CH (CH ₃ ) -COCH ₂ -COOH, CH ₂ -COOCH (CH ₃ ) -COOH or CH (CH ₃ ) -COOCH (CH ₃ ) -COOH;

Cχ-C ₄ -alkoxy- (Cχ-C ₄ -alkoxy) carbonyl-Cχ-C ₄ -alkyl for: (Cχ-C ₄ ~ alkoxy) carbonyl-Cχ-C ₄ -alkyl as mentioned above, which is a Cχ-C ₄ -alkoxy group such as OCH ₃ , OC ₂ H ₅ , OCH ₂ -C ₂ H ₅ , OCH (CH ₃ ) ₂ , n-butoxy, OCH (CH ₃ ) -C ₂ H ₅ , OCH ₂ -CH (CH ₃ ) ₂ and OC (CH ₃ ) ₃ , for example for CH ₂ -COOCH ₂ -OCH ₃ , CH ₂ -COOCH ₂ -OC ₂ H ₅ ,

CH ₂ -COOCH ₂ -OCH (CH ₃ ) ₂ , CH ₂ -COOCH ₂ -OC (CH ₃ ) ₃ , CH ₂ -COOCH ₂ -CH ₂ -OCH ₃ ,

CH ₂ -COOCH ₂ -CH ₂ -OC ₂ H ₅ , CH (CH ₃ ) -COOCH ₂ -CH ₂ - OCH ₃ or

CH (CH ₃ ) -COOCH ₂ -CH ₂ -OC ₂ H ₅ , especially for CH ₂ -COOCH ₂ -CH ₂ -OCH ₃ , CH ₂ -COOCH ₂ -CH ₂ -OC ₂ H ₅ , CH (CH ₃ ) -COOCH ₂ -CH ₂ -OCH ₃ or

CH (CH ₃ ) -COOCH ₂ -CH ₂ -OC ₂ H ₅ ;

(Cχ-C ₄ -alkoxy) carbonyl- (Cχ-C ₄ ~ alkoxy) carbonyl-Cχ-C ₄ -alkyl for: (Cχ-C ₄ -alkoxy) carbonyl-Cχ-C ₄ ~ alkyl as mentioned above, the one (Cχ-C ₄ alkoxy) carbonyl group such as C0OCH ₃ , COOC ₂ H ₅ ,

COOCH ₂ -C ₂ H ₅ , COOCH (CH ₃ ) ₂ , COOCH ₂ - (nC ₃ H ₇ ), OCH (CH ₃ ) -C ₂ H ₅ , OCH ₂ -CH (CH ₃ ) ₂ and OC (CH ₃ ) ₃ , e.g. for CH ₂ -COOCH ₂ -COOCH ₃ , CH ₂ -COOCH ₂ -COOC ₂ H ₅ , CH ₂ -COOCH ₂ -COOCH (CH ₃ ) ₂ , CH ₂ -COOCH ₂ -COOC (CH ₃ ) ₃ , CH ₂ -COOCH ₂ -COOCH ₃ , CH ₂ -COOCH ₂ -COOC ₂ H ₅ , CH (CH ₃ ) -COOCH ₂ -COOCH ₃ , CH (CH ₃ ) -COOCH ₂ -COOC ₂ H ₅ , CH ₂ -COOCH (CH ₃ ) -COOCH ₃ , CH ₂ - COOCH (CH ₃ ) -COOC ₂ H ₅ ,

CH (CH ₃ ) -COOCH (CH ₃ ) -COOCH ₃ or CH (CH ₃ ) -COOCH (CH ₃ ) -COOC ₂ H ₅ , in particular for CH ₂ -COOCH ₂ -COOCH ₃ , CH ₂ -COOCH ₂ -COOC ₂ H ₅ , CH (CH ₃ ) -COOCH ₂ -COOCH ₃ , CH (CH ₃ ) -COOCH ₂ -COOC ₂ H ₅ , CH ₂ -COOCH (CH ₃ ) -COOCH ₃ , CH ₂ -COOCH (CH ₃ ) -COOCH ₅ ,

CH (CH ₃ ) -COOCH (CH ₃ ) -COOCH ₃ or CH (CH ₃ ) -COOCH (CH ₃ ) -COOCH ₅ ;

(Cχ-C ₈ -haloalkoxy) carbonyl-Cx-Cς-alkyl for: by (Cχ-C ₈ -haloalkoxy) carbonyl such as COOCH ₂ F, COOCHF ₂ , COOCF ₃ , COOCH ₂ CI, COOCH (CI) ₂ , COOC ( Cl) ₃ , COOCHFC1, COOCF (Cl) ₂ ,

COOCF ₂ Cl, COOCF ₂ Br, COOCHF-CH ₃ , COOCH ₂ -CH ₂ F, COOCH ₂ -CH ₂ Cl, COOCH ₂ -CH ₂ Br, COOCH ₂ -CH ₂ I, COOCH ₂ -CH ₂ F, COOCH ₂ -CF ₃ , COOCH ₂ -CHFCI, COOCH ₂ -CF ₂ Cl, COOCH ₂ -CF (Cl) ₂ , COOCH ₂ -C (CI) ₃ , COOC ₂ F5, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl, 2, 2-difluoropropoxycarbonyl, 2, 3-difluoropropoxycarbonyl, 2, 3-dichloropropoxycarbonyl, COOCH ₂ CH ₂ -CF ₃ , COOCH ₂ CH ₂ -C (Cl ) ₃ , COOCH ₂ -C ₂ F ₅ , COOCF ₂ -C ₂ F ₅ , 1- (CH ₂ F) -2-fluoroethoxycarbonyl, 1- (0CH ₂ C1) -2-chloroethoxycarbonyl, 1- (OCH ₂ Br) -2-bromethoxycarbonyl, 4-fluorobutoxycarbonyl, 4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl, COOCF ₂ CF2-C ₂ F ₅ , 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl, 5-bromopent- oxycarbonyl, 5-iodopentoxycarbonyl, 5, 5, 5-trichloropentoxycarbonyl, CO0CF ₂ - (nC ₄ Fg), 6-fluorohexoxycarbonyl, 6-chlorohexoxycarbonyl, 6-bromhexoxy carbonyl, 6-iodohexoxycarbonyl, 6, 6, 6- Trichlorhexoxycarbonyl and COOCF - (n-CsFχχ) substituted Cχ-C ₆ alkyl, e.g. for CH ₂ -COOCH ₂ -CF ₃ , CH (CH ₃ ) -COOCH ₂ -CF ₃ , CH ₂ -COOCH ₂ -C (CI ) ₃ or CH (CH ₃ ) -COOCH ₂ -C (Cl) ₃ ;

(Cχ-C ₄ -alkoxy) carbonyl-Cχ-C ₄ -alkoxy for: substituted by (Cχ-C4 ~ alkoxy) carbonyl as mentioned above

Cχ-C4-alkoxy, e.g. for OCH ₂ COOCH ₃ , OCH ₂ COOC ₂ H ₅ , OCH ₂ COOCH ₂ -C ₂ H ₅ , OCH ₂ COOCH (CH ₃ ) ₂ , OCH ₂ COOCH ₂ CH ₂ -C ₂ H ₅ , OCH ₂ COOCH (CH ₃ ) -C ₂ H ₅ , OCH ₂ COOCH ₂ -CH (CH ₃ ) ₂ , 0CH ₂ C00C (CH ₃ ) ₃ , 0CH (CH ₃ ) C0OCH ₃ , OCH (CH ₃ ) COOC ₂ H ₅ , OCH ₂ CH ₂ COOCH ₃ , OCH CH ₂ COOC ₂ H ₅ , OCH ₂ CH ₂ COOCH2-C2H ₅ , OCH ₂ CH ₂ COOCH (CH ₃ ) ₂ , OCH ₂ CH ₂ COOCH ₂ CH ₂ -C ₂ H ₅ ,

2- [COOCH (CH ₃ ) -C ₂ H ₅ ] ethoxy, 2- [COOCH ₂ -CH (CH ₃ ) ₂ ] ethoxy, OCH ₂ CH ₂ COOC (CH ₃ ) ₃ , 2- (COOCH ₃ ) propoxy, 2- (COOC ₂ H ₅ ) propoxy,

2- (COOCH ₂ -C ₂ H ₅ ) propoxy, 2- [COOCH (CH ₃ ) ₂ ] propoxy,

2- (COOCH ₂ CH2-C ₂ H ₅ ) propoxy, 2- [COOCH (CH ₃ ) -C ₂ H ₅ ] propoxy, 2- [COOCH ₂ -CH (CH ₃ ) ₂ ] propoxy, 2- [COOC ( CH ₃ ) ₃ ] propoxy,

3- (COOCH ₃ ) propoxy, 3- (COOC ₂ H ₅ ) propoxy, 3- (COOCH ₂ -C ₂ H ₅ ) propoxy,

3- [COOCH (CH ₃ ) ₂ ] propoxy, 3- (COOCH ₂ CH ₂ -C ₂ H ₅ ) propoxy,

3- [COOCH (CH ₃ ) -C ₂ H ₅ ] propoxy, 3- [C00CH ₂ -CH (CH ₃ ) ₂ ] propoxy, 3- [COOC (CH ₃ ) ₃ ] propoxy, 2- (C00CH ₃ ) butoxy, 2- (COOC ₂ H ₅ ) butoxy, 2- (COOCH ₂ -C ₂ H ₅ ) butoxy, 2- [COOCH (CH ₃ ) ₂ ] butoxy,

2- (COOCH ₂ CH ₂ -C ₂ H ₅ ) butoxy, 2- [COOCH (CH ₃ ) -CH ₅ ]] butoxy, 2- [COOCH ₂ -CH (CH ₃ ) ₂ ] butoxy, 2- [COOC ( CH ₃ ) ₃ ] butoxy,

3- (COCH ₃ ) butoxy, 3- (COOC ₂ H ₅ ) butoxy, 3- (COOCH ₂ -C ₂ H ₅ ) butoxy,

3- [COOCH (CH ₃ ) ₂ ] butoxy, 3- (COOCH ₂ CH ₂ -C ₂ H ₅ ) butoxy, 3- [COOCH (CH ₃ ) -C ₂ H ₅ ] butoxy, 3- [COOCH ₂ -CH (CH ₃ ) ₂ ] butoxy,

3- [COOC (CH ₃ ) ₃ ] butoxy, 4- (COOCH ₃ ) butoxy, 4- (COOC ₂ H ₅ ) butoxy, 4- (COOCH ₂ -C ₂ H ₅ ) butoxy, 4- [COOCH (CH ₃ ) ₂ ] butoxy,

4- (COOCH ₂ CH ₂ -C ₂ H ₅ ) butoxy, 4- [COOCH (CH ₃ ) -C ₂ H ₅ ] butoxy,

4- [COOCH ₂ -CH (CH ₃ ) ₂ ] butoxy or 4- [1, 1-C00C (CH ₃ ) ₃ ] butoxy, especially for 0CH ₂ -C00CH ₃ , OCH ₂ -COOC ₂ H ₅ , 0CH ₂ -COOCH ₂ -C ₂ H ₅ ,

OCH ₂ - COOCH (CH ₃ ) ₂ , OCH ₂ - CO0CH ₂ - CH ₂ - C ₂ H ₅ , 0CH ₂ - COOCH (CH ₃ ) - C ₂ H ₅ , OCH ₂ - C00CH - CH (CH ₃ ) ₂ , OCH ₂ - COOCH2 - CH ₂ CH ₂ "C ₂ H ₅ , OCH (CH ₃ ) - COOCH ₃ , OCH (CH ₃ ) - COOC ₂ H ₅ , OCH (CH ₃ ) - COOCH ₂ - C ₂ H ₅ , OCH (CH ₃ ) - COOCH (CH ₃ ) ₂ , OCH (CH ₃ ) - CO0CH ₂ - CH ₂ - C ₂ H ₅ , OCH (CH ₃ ) - COOCH (CH ₃ ) - C ₂ H ₅ , OCH (CH ₃ ) -COOCH ₂ -CH (CH ₃ ) ₂ , OCH (CH ₃ ) -COOC (CH ₃ ) ₃ or

OCH (CH ₃ ) -COOCH ₂ -CH ₂ CH ₂ -C ₂ H ₅ ;

Cχ-C4-alkylthio-Cχ-C ₄ alkyl: by Cχ-C4-alkylthio as mentioned above substituted _Cχ-C4 alkyl, eg CH ₂ -SCH _3, CH ₂ -SC ₂ H _5, n- Propyl thiomethyl, CH ₂ -SCH (CH ₃ ) ₂ , n-butylthiomethyl, (1-methyl-propyl thio) ethyl, (2-methyl-propyl thio) methyl, CH ₂ -SC (CH ₃ ) ₃ , 2-methylthioethyl , 2-ethyl thioethyl, 2- (n-propylthio) ethyl, 2- (1-methylethylthio) ethyl,

2- (n-butylthio) ethyl, 2- (1-methyl-propylthio) ethyl,

2- (2-methylpropylthio) ethyl, 2- (1, 1-dimethylethylthio) ethyl,

2- (methylthio) propyl, 3- (methylthio) propyl, 2- (ethylthio) propyl, 3- (ethylthio) propyl, 3- (propylthio) propyl,

3- (butylthio) propyl, 4- (methylthio) butyl, 4- (ethylthio) butyl,

4- (n-propylthio) butyl or 4- (n-butylthio) butyl, especially for 2- (methylthio) ethyl;

- Cχ-C -Alkylsulfinyl for: SO-CH ₃ , SOC ₂ H ₅ , SO-CH ₂ -C ₂ H ₅ , SO-CH (CH ₃ ) ₂ , n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or SO -C (CH ₃ ) ₃ , especially for S0-CH ₃ or SO-C ₂ H ₅ ;

- Cχ-C ₄ -alkylsulfinyl-Cχ-C-alkyl for: Cχ-C ₄ -alkylsulfinyl as mentioned above, preferably SO-CH ₃ , substituted Cχ-C ₄ ~ alkyl, so for example for CH -SO-CH ₃ or 2-methylsulfinylethyl;

- Cχ-C-Alkylsulfonyl for: S0 ₂ -CH ₃ , S0 -CH ₅ , S0 ₂ -CH ₂ -C ₂ H ₅ , S0 ₂ -CH (CH ₃ ) ₂ , n-butylsulfonyl, 1-methylpropylsulfonyl, S0 ₂ -CH ₂ -CH (CH ₃ ) ₂ or S0 ₂ -C (CH ₃ ) ₃ , in particular for S0 ₂ -CH ₃ or SO ₂ -C ₂ H ₅ ;

- Cχ-C ₄ -alkylsulfonyl-Cχ-C ₄ -alkyl for: by C durch-C ₄ -alkylsulfonyl as mentioned above, preferably Sθ ₂ "CH ₃ , substituted Cχ-C ₄ ~ alkyl, so for example for CH ₂ " Sθ ₂ -CH or 2 -methylsulfonylethyl;

- (Cχ-C ₈ alkyl) aminocarbonyl for: e.g. CO-NH-CH ₃ , CO-NH-C ₂ H ₅ , CO-NH-CH ₂ -C ₂ H ₅ , CO-NH-CH (CH ₃ ) ₂ , CO-NH-CH ₂ CH ₂ -C ₂ H ₅ , CO-NH-CH (CH ₃ ) CH ₅ , CO-NH-CH ₂ -CH (CH ₃ ) ₂ , CO-NH-C (CH ₃ ) ₃ , n-pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutyl-a inocarbonyl, 3-methylbutylaminocarbonyl, 2, 2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl, 1, 1-dimethylpropylaminocarbonyl 2-dimethyl-propyla inocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentyl inocarbonyl, 3-methylpentylaminocarbonyl, 4-methyl-pentylaminocarbonyl, 1, 1-dimethylbutylaminocarbonyl, 1, 2-di-methylbutylaminocarbonyl, 1, 3-dimethylbutylaminocarbonyl 2-dimethylbutylaminocarbonyl, 2, 3-dimethylbutylaminocarbonyl, 3, 3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1, 1, 2-trimethylpropylaminocarbonyl, 1,2, 2-trimethylpropylaminylcarbonyl l-methylpropylaminocarbonyl or l-ethyl-2-me thylpropylamino carbonyl, especially for CO-NH-CH ₃ , CO-NH-C ₂ H ₅ , n-propyl-aminocarbonyl, C0-NH-CH (CH ₃ ) 2, n-butylaminocarbonyl, CO-NH-C (CH ₃ ) ₃ , n-pentylaminocarbonyl or n-hexylaminocarbonyl;

Di (Cx-C ₈ -alkyl) aminocarbonyl for: e.g. CO-N (CH ₃ ) ₂ , CO-N (C ₂ H ₅ ) ₂ , CO-N (CH ₂ -C ₂ H ₅ ) ₂ , CO-N [CH (CH ₃ ) ₂ ] ₂ , CO-N (nC ₄ H ₉ ) ₂ ,

CO-N [CH (CH ₃ ) -C ₂ H ₅ ] ₂ , CO-N [CH ₂ -CH (CH ₃ ) ₂ ] ₂ CO-N [C (CH ₃ ) ₃ ] ₂ , CO-N (CH ₃ ) -CH ₅ , CO-N (CH ₃ ) -CH ₂ -C ₂ H ₅ , CO- (CH ₃ ) -CH (CH ₃ ) ₂ , CO-N (CH ₃ ) - (nC ₄ H ₉ ) , CO-N (CH ₃ ) -CH (CH ₃ ) -C ₂ H ₅ , CO-N (CH ₃ ) -CH ₂ -CH (CH ₃ ) ₂ , CO- (CH ₃ ) -C (CH ₃ ) ₃ , CO-N (C ₂ H ₅ ) -CH ₂ -C ₂ H ₅ , CO-N (C ₂ H ₅ ) -CH (CH ₃ ) ₂ , CO-N (C ₂ H ₅ ) - (nC ₄ H ₉ ),

CO-N (C ₂ H ₅ ) -CH (CH ₃ ) -C ₂ H ₅ , CO-N (C ₂ H ₅ ) -CH ₂ -CH (CH ₃ ) ₂ , CO-N (C ₂ H ₅ ) -C (CH ₃ ) ₃ , N- [CH (CH ₃ ) ₂ ] -N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N- [1-methylpropyD -N-propylaminocarbonyl, N- [2-methylpropyl] - N-propylaminocarbonyl, N- [C (CH ₃ ) ₃ ] -N-propylaminocarbonyl, N-butyl-N- [1-methyl-ethyl] aminocarbonyl, N- [CH (CH ₃ ) ₂ ] -N- (1- methylpropyl) aminocarbonyl, N- [CH (CH ₃ ) ₂ ] -N- [2-methylpropyl] aminocarbonyl, N- [C (CH ₃ ) ₃ ] -N- [CH (CH ₃ ) ₂ ] aminocarbonyl, N-butyl -N- [(1-methylpropyl] aminocarbonyl, N-butyl-N- [2-methylpropyl] aminocarbonyl, N-butyl-N- [C (CH ₃ ) ₃ ] aminocarbonyl, N- [1-methyl - propyl] -N- [2-methylpropyl] aminocarbonyl, N- [C (CH ₃ ) ₃ ] -N- [1-methylpropyl] aminocarbonyl or N- [C (CH ₃ ) ₃ ] -N- [2-methylpropyl ] aminocarbonyl, especially for CO-N (CH ₃ ) ₂ or CO-N (C ₂ H ₅ ) ₂ ;

C ₃ -C ₈ alkenyl for: e.g. prop-2-en-l-yl, n-buten-4-yl, l-methyl-prop-2-en-l-yl, 2-methyl-prop-2- en-l-yl, 2-butene-1-yl, n-penten-3-yl, n-penten-4-yl, l-methyl-but-2-en-l-yl, 2-methyl-but- 2-en-l-yl, 3-methyl-but-2-en-l-yl, 1-methyl-but-3-en-l-yl, 2-methyl-but-3-en-l-yl, 3-methyl-but-3-en-l-yl, 1, l-dimethyl-prop-2-en-l-yl, 1, 2-dimethyl-prop-2-en-1-yl, l-ethyl prop-2-en-l-yl, n-hex-3-en-l-yl, n-hex-4-en-1-yl, n-hex-5-en-l-yl, l-methyl pent-3-en-l-yl, 2-methyl-pent-3-en-l-yl, 3-methyl-pent-3-en-l-yl, 4-methyl-pent-3-en-l- yl, l-methyl-pent-4-en-l-yl, 2-methyl-pent-4-en-l-yl, 3-methyl-pent-4-en-l-yl, 4-methyl-pent 4-en-l-yl, 1,1-dimethyl-but-2-en-l-yl, 1, l-dimethyl-but-3-en-l-yl, 1, 2-dimethyl-but- 2-en-1-yl, 1, 2-dimethyl-but-3-en-1-yl, 1,3-dimethyl-but-2-en-1-yl, 1, 3-dimethyl-but- 3-en-l-yl, 2,2-dimethyl-but-3-en-l-yl, 2,3-dimethyl-but-2-en-l-yl, 2,3-dimethyl but-3-en-l-yl, 3, 3-dimethyl-but-2-en-l-yl, 1-ethyl-but-2-en-l-yl, l-ethyl-but-3-en- l-yl, 2-ethyl-but-2-en-l-yl , 2-ethyl-but-3-en-l-yl, 1,1, 2-trimethyl-prop-2-en-l-yl, l-ethyl-l-methyl-prop-2-en-l-yl , l-ethyl-2-methyl-prop-2-en-l-yl, n-hept-2-en-l-yl, n-hept-3 -en-l-yl, n-oct-2-ene - 1-yl or n-oct-3 -en-l-yl, in particular for prop-2 -en-l-yl or n-buten-4-yl;

C -C ₈ haloalkenyl for: C -C ₆ alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 2-chloroallyl, 3-chloroallyl, 2, 3-dichloroallyl , 3, 3-dichlorallyl, 2,3,3-trichlorallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3 , 3-tribromoallyl or 2,3-dibromobut-2-enyl, especially for 2-chloroallyl or 3,3-dichlorallyl;

C ₂ -C ₈ haloalkenyl for: 1-chlorovinyl, 2 -chlorovinyl, 1,2-dichlorovinyl, 1, 2, 2 -trichlorovinyl or one of the abovementioned C ₃ -C ₈ -halogenalkenyl radicals;

Cyano-C ₂ -C ₈ -alkenyl for: for example 2-cyanovinyl, 3-cyanoallyl, 4-cyano-but-2-enyl, 4-cyano-but-3-enyl or 5-cyano-pent-4-enyl, preferably 3-cyanoallyl or 4-cyano-but-2-enyl, in particular for 3-cyanoallyl;

C ₂ -C ₄ alkenyloxy-Cχ-C ₄ alkyl for: by C ₂ -C ₄ alkenyloxy such as vinyloxy, prop-2-enyloxy, but-l-en-3-yloxy, but-l-en-4 -yloxy, n-but-2-enyloxy, n-but-3-enyloxy, l-methyl-prop-2-enyloxy or 2-methyl-prop-2-enyloxy - preferably allyloxy,

2-methylprop-2-en-l-yloxy, but-l-en-3-yloxy, but-l-en-4-yloxy or but-2-en-l-yloxy - substituted Cχ-C ₄ -alkyl, for example for vinyloxymethyl, allyloxymethyl, 2- (allyloxy) ethyl or but-l-en-4-yloxymethyl;

(C ₃ -C ₆ -Alkenyloxy) carbonyl- (Cχ-C ₄ -alkoxy) carbonyl-Cχ-C ₄ -alkyl for: (Cχ-C ₄ -alkoxy) carbonyl-Cχ-C ₄ -alkyl as mentioned above, the a (C ₃ -C ₆ ~ alkenyloxy) carbonyl group such as prop-1-en-l-yl-O-CO, prop-2-en-l-yl-O-CO, 1-methylethenyl-O-CO, n- Buten-1-yl-O-CO, n-buten-2-yl-O-CO, n-buten-3-yl-

O-CO, 1-methyl-prop-l-en-l-yl-O-CO, 2-methyl-prop-l-en-l-yl-O-CO, l-methyl-prop-2-en- l-yl-O-CO, 2-methyl-prop-2-en-l-yl-O-CO, n-penten-1-yl-O-CO, n-penten-2-yl-O-CO, n-penten-3-yl-O-CO, n-penten-4-yl-O-CO, 1-methyl-but-l-en-1-yl-O-CO, 2-methyl-but-l- en-l-yl-O-CO, 3-methyl-but-l-en-l-yl-O-CO, l-methyl-but-2-en-l-yl-O-CO, 2-methyl- but-2-en-l-yl-0-CO, 3-methyl-but-2-en-l-yl-0-CO, l-methyl-but-3-en-l-yl-O-CO, 2-methyl-but-3-en-l-yl-0-CO, 3-methyl-but-3-en-l-yl-0-CO, 1, l-dimethyl-prop-2-en-l- yl-O-CO, 1, 2-dimethyl-prop-1-en-l-yl-O-CO, 1, 2-dimethyl-prop-2-en-l-yl-0-CO, l-ethyl prop-l-en-2-yl-O-CO, l-ethyl-prop-2-en-l-yl-O-CO, n-hex-1-en-l-yl-O-CO, n- Hex-2-en-l-yl-O-CO, n-hex-3-en-l-yl- O-CO, n-hex-4-en-l-yl-O-CO, n-hex-5-en-l-yl-0-C0, 1-methyl-pent-l-en-l-yl- O-CO, 2-methyl-pent-l-en-l-yl-O-CO, 3-methyl-pent-1-en-l-yl-O-CO, 4-methyl-pent-l-en- l-yl-O-CO, 1-methyl-pent-2-en-l-yl-O-CO, 2-methyl-pent-2-en-l-yl-0-C0, 3-methyl-pent- 2-en-l-yl-O-CO, 4-methyl-pent-2-en-l-yl-0-CO, 1-methyl-pent-3-en-l-yl-O-CO, 2- Methyl-pent-3-en-l-yl-0-CO, 3-methyl-pent-3-en-l-yl-O-CO, 4-methyl-pent-3-en-l-yl-0- CO, 1-methyl-pent-4-en-l-yl-O-CO, 2-methyl-pent-4-en-l-yl-0-CO, 3-methyl-pent-4-en-l- yl-O-CO, 4-methyl-pent-4-en-l-yl-0-CO, 1,1-dimethyl-but-2-en-l-yl-O-CO, 1, l- Dimethyl-but-3-en-l-yl-O-CO, 1,2-dimethyl-but-l-en-l-yl-O-CO, 1,2-dimethyl-but-2-en-l- yl-O-CO, l, 2-dimethyl-but-3-en-l-yl-0-CO, 1, 3-dimethyl-but-1-en-l-yl-O-CO, 1, 3- Dimethyl-but-2-en-l-yl-0-CO, 1,3-dimethyl-but-3-en-l-yl-O-CO, 2,2-dimethyl-but-3-en- l-yl-O-CO, 2,3-dimethyl-but-l-en-l-yl-O-CO, 2, 3-dimethyl-but-2-en-l-yl-O-CO, 2, 3-dimethyl-but-3-en-1-yl-0-CO, 3, 3-dimethyl-but-1-en-1-yl-O-CO, 3, 3-dimethyl-b ut-2-en-l-yl-0-CO, 1-ethyl-but-l-en-l-yl-O-CO, l-ethyl-but-2-en-l-yl-O-CO, 1-ethyl-but-3-en-l-yl-O-CO, 2-ethyl-but-l-en-l-yl-O-CO, 2-ethyl-but-2-en-l-yl- O-CO, 2-ethyl-but-3-en-l-yl-0-CO, 1,1,2-trimethyl-prop-2-en-l-yl-O-CO, l-ethyl- l-methyl-prop-2-en-l-yl-O-CO, l-ethyl-2-methyl-prop-l-en-l-yl-O-CO and l-ethyl-2-methyl-prop- 2-en-l-yl-0-CO, e.g. for CH ₂ -COOCH ₂ -COOCH2-CH = CH ₂ , CH ₂ -COOCH (CH ₃ ) -COOCH ₂ -CH = CH ₂ , CH (CH ₃ ) -COOCH (CH ₃ ) -COOCH ₂ -CH = CH ₂ or CH (CH ₃ ) -COOCH (CH ₃ ) -COOCH ₂ -CH = CH ₂ ;

(C ₃ -C ₈ alkenyloxy) carbonyl -Cx-C _ß- alkyl for: Cχ-C ₆ alkyl which has a (C ₃ -C ₆ alkenyloxy) carbonyl radical - as mentioned above - or, for example, n -Hept-2 -en-1 -yl-O-CO, n-hept-3 -en-l-yl - O-CO, n-Oct-2-en-l-yl-O-CO or n-Oct -3-en-l-yl-O-CO, for example for allyloxycarbonylmethyl, 2- (allyloxycarbonyl) ethyl or but-1-en- 4 -yloxycarbonylmethyl;

C ₃ -C ₈ alkynyl for: for example propargyl, n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-l-yl, n- Pent-l-in-3-yl, n-pent-l-in-4-yl, n-pent-l-in-5-yl, n-pent-2-in-l-yl, n-pent 2-in-4-yl, n-pent-2-in-5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n- Hex-1-in-3-yl, n-hex-1-in-4-yl, n-hex-1-in-5-yl, n-hex-1-in-6-yl, n-hex 2-in-1-yl, n-hex-2-in-4-yl, n-hex-2-in-5-yl, n-hex-2-in-6-yl, n-hex-3- in-1-yl, n-hex-3-in-2-yl, 3-methyl-pent-1-in-3-yl, 3-methyl-pent-1-in-4-yl, 3-methyl pent-l-in-5-yl, 4-methyl-pent-2-in-4-yl or 4-methyl-pent-2-in-5-yl, in particular for propargyl; C ₂ -C ₈ haloalkynyl for: ethynyl or C ₃ -Cg alkynyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for l, l-difluoroprop-2-in -l-yl, 4-fluorobut-2-in-l-yl, 4-chlorobut-2-in-l-yl, 1, 1-difluorobut-2-in-l-yl, 5-fluoropent-3 -in-1-yl or 6-fluorohex-4-in-1-yl;

Cyano-C ₃ -C ₈ -alkynyl for: e.g. 1-cyanopropargy1, 3-cyanopropargyl, 4-cyanobut-2-in-l-yl, 5-cyanopent-3 -in-l-yl or 6-cyanohex- 4-in-1-yl;

C ₂ -C ₄ alkynyloxy-Cχ-C ₄ -alkyl for: by C ₂ -C ₄ -alkynyloxy such as ethynyloxy, propargyloxy, n-but-1-yn-3-yloxy, n-but-1-yn 4 -yloxy and n-but-2-yn-l-yloxy, substituted Cχ-C ₄ alkyl, for example for CH ₂ -OC≡CH, CH ₂ -OCH ₂ -C ≡CH or 2 - (propargyloxy) ethyl;

(C ₃ -C ₆ -alkynyloxy) carbonyl- (Cχ-C ₄ -alkoxy) carbonyl-Cχ-C -alkyl for: (Cχ-C ₄ -alkoxy) carbonyl-Cχ-C ₄ -alkyl as mentioned above, one (C ₃ -C ₆ alkynyloxy) carbonyl group such as propargyl-O-CO, prop-2-in-1-yl-O-CO, n-but-1-in-1-yl-O-CO , n-But-l-in-3-yl-O-CO, n-But-l-in-4-yl-O-CO, n-But-2-in-l-yl-O-CO, n Pent-1-in-1-yl-O-CO, n-pent-1-in-3-yl-O-CO, n-pent-1-in-4-yl-O-CO, n-pent -l-in-5-yl-O-CO, n-pent-2-in-l-yl-O-CO, n-pent-2-in-4-yl-O-CO, n-pent-2 -in-5-yl-0-CO, 3-methylbut-l-in-3-yl-O-CO, 3-methylbut-l-in-4-yl-0-CO, n-hex-1 -in-1-yl-O-CO, n-hex-1-in-3-yl-O-CO, n-hex-1-in-4-yl-O-CO, n-hex-1-in -5-yl-O-CO, n-hex-1-in-6-yl-O-CO, n-hex-2-in-1-yl-O-CO, n-hex-2-in-4 -yl-0-CO, n-Hex-2-in-5-yl-O-CO, n-Hex-2-in-6-yl-0-CO, n-Hex-3-in-l-yl -O-CO, n-

Hex-3-in-2-yl-0-CO, 3-methylpent-l-in-l-yl-O-CO, 3-methylpent-l-in-3-yl-O-CO, 3- Methylpent-l-in-4-yl-0-CO, 3-methylpent-l-in-5-yl-O-CO, 4-methylpent-l-in-l-yl-O-CO, 4- Methyl pent-2-in-4-yl-0-CO and 4-methylpent-2-in-5-yl-O-C0, for example for CH ₂ -COOCH ₂ -COOCH ₂ -C≡CH,

CH ₂ -COOCH (CH ₃ ) -COOCH ₂ -C≡ CH, CH (CH ₃ ) -COOCH ₂ -COOCH ₂ -C≡CH or CH (CH ₃ ) -COOCH (CH ₃ ) -COOCH ₂ -C≡CH ;

(C ₃ -C ₈ alkynyloxy) carbonyl-Cχ-C ₆ -alkyl for: Cχ-C ₆ -alkyl, which preferably has a (C ₃ -Cg-alkynyloxy) carbonyl radical as mentioned above, in particular CO-OCH ₂ - C≡CH, But-l-in-3-yl-O-CO, But-l-in-4-yl-O-CO or But-2-in-l-yl-O-CO, for example for CH ₂ -CO-OCH ₂ -C≡CH or 2- (propargyloxycarbonyl) ethyl; C ₃ -C ₈ cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl,

Cyclohexyl, cycloheptyl or cyclooctyl, especially for

Cyclopentyl or cyclohexyl;

(C ₃ -C Cycloalkyloxy) carbonyl -Cχ-C ₄ alkyl for: eg cyclopropyloxycarbonylmethyl, cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, cycloheptyloxycarbonylmethyl, 1- (cyclopropyloxycarbonyl) ethyl, 1- (cyclobutyloxycarbonyl) ethyl - (Cyclopentyloxycarbonyl) ethyl, 1- (cyclohexyloxycarbonyl) ethyl, 1- (cyclo-heptyloxycarbonyl) ethyl, 2- (cyclopropyloxycarbonyl) ethyl, 2- (cyclobutyloxycarbonyl) ethyl, 2- (cyclopentyloxycarbonyl) ethyl, 2- ( Cyclohexyloxycarbonyl) ethyl, 2- (cyclo-heptyloxycarbonyl) ethyl, 3- (cyclopropyloxycarbonyl) propyl, 3- (cyclobutyloxycarbonyl) propyl, 3- (cyclopentyloxycarbonyl) propyl, 3- (cyclohexyloxycarbonyl) propyl, 3- (cyclo-heptyloxycarbonyl) propyl, 4- (cyclopropyloxycarbonyl) butyl, 4- (cyclobutyloxycarbonyl) butyl, 4- (cyclopentyloxycarbonyl) butyl, 4- (cyclohexyloxycarbonyl) butyl or 4- (cycloheptyloxycarbonyl) butyl, especially for cyclopentyloxycarbonylmethyl, cyclohexyloxycarbo nylmethyl or 2- (cyclopentyloxycarbonyl) ethyl;

(C ₃ -C ₈ -cycloalkyloxy) carbonyl-Cx-C _ß -alkyl for: e.g. cyclopropyloxycarbonylmethyl, cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, cycloheptyloxycarbonylmethyl, cyclooctyloxycarbonylmethyl, 1- (cyclopropyloxy) 1- (cyclopropyloxy) 1- (cyclopropyloxy) cyclo ethyl, 1- (cyclopentyloxycarbonyl) ethyl, 1- (cyclohexyloxycarbonyl) ethyl, 1- (cycloheptyloxycarbonyl) ethyl, 1- (cyclooctyloxycarbonyl) ethyl, 2- (cyclopropyloxycarbonyl) ethyl, 2- (cyclobutyloxycarbonyl) ethyl, 2- (cyclopentyloxycarbonyl) ethyl, 2- (cyclohexyloxycarbonyl) ethyl, 2- (cycloheptyloxycarbonyl) ethyl, 2- (cyclooctyloxycarbonyl) ethyl, 3- (cyclopropyloxycarbonyl) propyl, 3- (cyclobutyloxycarbonyl) propyl, 3- (cyclopentyloxycarbonyl) propyl, 3- ( Cyclohexyloxycarbonyl) propyl, 3- (cycloheptyloxycarbonyl) ropyl, 3- (cyclooctyloxycarbonyl) propyl, 4- (cyclopropyloxycarbonyl) butyl, 4- (cyclobutyloxycarbonyl) butyl, 4- (cyclopentyloxycarbonyl) butyl, 4- (cyclohexylox ycarbonyl) butyl, 4- (cycloheptyloxycarbonyl) butyl,

4- (cyclooctyloxycarbonyl) butyl, 5- (cyclopropyloxycarbonyl) pentyl, 5- (cyclobutyloxycarbonyl) pentyl, 5 - (cyclopentyloxycarbonyl) pentyl, 5- (cyclohexyloxycarbonyl) pentyl, 5- (cycloheptyloxycarbonyl) pentyl, 5- (cyclooctyloxycarbonyl) pentyl 6- (cyclopropyloxycarbonyl) hexyl, 6- (cyclobutyloxycarbonyl) hexyl, 6 - (cyclopentyloxycarbonyl) hexyl, 6- (cyclohexyloxycarbonyl) hexyl, 6 - (cycloheptyloxycarbonyl) exyl or 6 - (Cyclooctyloxycarbonyl) hexyl, especially for cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl or 2 - (cyclopentyloxycarbonyl) ethyl;

- C ₅ -C ₈ cycloalkenyl for: cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3-enyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohept- 1-enyl, cyclohept-2-enyl, cyclohept-3-enyl, cyclohept-4-enyl, cyclooct-1-enyl, cyclooct-2-enyl, cyclooct-3-enyl or cyclooct-4-enyl, especially for cyclo- pent-1-enyl, cyclopent-2-enyl, cyclohex-1-enyl or cyclo-hex-2-enyl;

(0χ -C ₄ alkoxy) carbonyl -C ₃ -C ₇ - cycloalkyl for: eg methoxycarbonylcyclopentyl, ethoxycarbonylcyclopentyl, methoxycarbonyl ^■ cyclohexyl or ethoxycarbonylcyclohexyl.

With regard to the use of the substituted 2-benz (o) ylpyridines I as herbicides and / or as desiccant / defoliant compounds, the variables preferably have the following meanings, individually or in combination:

n zero;

X carbonyl or methylene, especially methylene;

R ¹ Cχ-C ₄ haloalkyl, especially trifluoromethyl;

R ² halogen, especially chlorine;

R ³ halogen, especially chlorine;

R ⁴ halogen, especially chlorine;

R ⁵ -OR ⁸ , -CO-OR ⁸ , -CO-N (R ⁹ , R ¹⁰ ) or -CH = N-0R ¹³ , in particular -OR ⁸ ;

R ^{6 is} hydrogen or halogen, especially hydrogen;

R ^{7 is} hydrogen or halogen, especially hydrogen;

R ^{8 is} hydrogen, Cχ-C ₈ alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl,

Hydroxycarbonyl -0χ-C4 - alkyl, (0 -C ₈ alkoxy) carbonyl -Cx - Ce - alkyl, (C ₃ -C ₈ alkenyloxy) carbonyl -Cχ-Cβ-alkyl, (C ₃ -C ₈ alkynyl - oxy) carbonyl -Cχ-C ₆ -alkyl, Cχ-C ₄ -alkoxy- (C -C ₄ - alkoxy) carbonyl-Cχ-C ₄ -alkyl, (Cχ-C ₄ -alkoxy) carbonyl- (Cχ-C ₄ - alkoxy) carbonyl - C ₁ -C ₄ - alkyl, CH ₂ CO CO OR ²³ CH (R ²² ) CO 0 (

CO OR ²³

CH (R ²² ) CO N (R ⁹ , R ¹⁰ ), CH (R ²² ) CO CO OR ²³ ,

N OR ¹³

CH (R ²² ) C CO OR ²³ .

CH (R ²² ) CO N OR ²⁵

| or

CH (R ²² ) CO OR ²³

CH (R ²² ) C OCH (R ²² ) CO OR ²³

N OR ²⁵

especially hydrogen, Cχ-C ₈ alkyl, C ₃ -C ₈ alkenyl, C ₃ - C ₈ alkynyl, (Cx - C ₈ alkoxy) carbonyl - Cx - C ₆ - alkyl, -CH (R ²² ) - CO-N (R ⁹ , R ^{! 0} ), -CH (R ²² ) -CO-CO-OR ²³ or

N OR ¹³

I CH (R ²² ) C CO OR ²³ :

R ⁹ , R ^{10 are} hydrogen, Cχ-C ₈ -alkyl or (Cχ-C-alkoxy) carbonyl-Cχ-C - alkyl, in particular Cχ-C ₈ -alkyl;

R ^{13 is} hydrogen, Cχ-C ₈ -alkyl, C ₃ -C ₈ -alkenyl, C ₃ -C ₈ -alkynyl or (Cχ-C ₄ -alkoxy) carbonyl-Cχ-C ₄ -alkyl, in particular Cχ-C ₈ - Alkyl;

R ^{22 is} hydrogen, Cχ-C ₈ alkyl, C ₃ -C ₈ alkenyl or C ₃ -C ₈ alkynyl, in particular Cχ-C ₈ alkyl;

R ^{23 is} hydrogen, Cχ-C ₈ alkyl, C ₃ -C ₈ alkenyl or C ₃ -C ₈ alkynyl, in particular Cχ-C ₈ alkyl;

R ^{25 is} hydrogen, Cχ-C ₈ alkyl, C ₃ -C ₈ alkenyl or C ₃ -C ₈ alkynyl, especially Cχ-C ₈ alkyl. The substituted 2-benz (o) ylpyridines of the formula I can be obtained in various ways, for example by one of the following processes:

Procedure A>

Reaction of substituted pyridines of the formula II with benzyl nitriles of the formula III in the presence of a base {cf. e.g. R.J. Wolters et al. , J. Pharmaceut. Sciences £ 4. / 2013 (1975); Z.-T. Huang et al., Synth. Commun. 21: 591 (1993); H. Yamanaka and S. Ohba, Heterocycles 3_1, 895 (1990):

^{11 XI1} I {X = CH (CN)}

{L = halogen or

Cχ-C ₆ alkoxy}

Usually one works in an inert solvent or diluent, especially a dipolar aprotic solvent, e.g. in N, N-dimethylformamide, N-methylpyrrolidone or in an ether such as diethyl ether, 1,2-ethoxyethane, tetrahydrofuran and dioxane.

As bases come e.g. the alkali metal hydrides, amides, carbonates and hydrogen carbonates, and also nitrogen bases such as triethylamine, pyridine and 4-dimethylaminopyridine, into consideration. In addition, the alkali metal salts of bulky alcohols such as potassium tert. -butylate can be used.

The reaction temperature is usually 0 to 150 ° C.

The reactants are usually used in approximately stoichiometric amounts, but an excess of one of the components, e.g. in view of the complete conversion of the other component being advantageous.

The substituted pyridines II and benzyl nitriles III are either known and in some cases even commercially available, or can be easily prepared by methods known per se. For the production of benzyl nitriles from benzyl halides, see, for example, VG Telang and CJ Smith, J. Pharm. j> 9_, 1521 (1970). Procedure B>

Partial hydrolysis of compounds I with X = CH (CN), e.g. in conc. Sulfuric acid {cf. e.g. R.J. Wolters et al. , J. Pharm.

Be. £ -4, 2013 (1975)}, to subst. 2 -Benz (o) ylpyridinen I with X =

CH-CONH ₂ , their alcoholysis {cf. Here too, for example, RJ Wolters et al.} leads to 2-benz (o) ylpyridines I with X = CH-CO-0 (Cχ-C-alkyl):

The hydrolysis with conc. Sulfuric acid is usually carried out at 0 to 50 ° C, preferably at room temperature.

The subsequent alcoholysis is preferably carried out in excess alcohol HO (Cχ-C ₄ -alkyl) as solvent, but other inert solvents / diluents can also be used. Alcoholysis is catalyzed by mineral acids such as hydrogen chloride.

Usually one works at 0 to 150 ° C, preferably at the boiling point of the alcohol HO (Cχ-C ₄ alkyl).

Procedure C>

Hydrolysis of 2-benz (o) ylpyridines of the formula I in which X is CH-CN, CH-CONH ₂ or CH-CO-0 (Cχ-C ₄ -alkyl) in the presence of an aqueous acid:

As acids e.g. Mineral acids such as hydrochloric acid, hydrobromic acid and sulfuric acid or organic acids such as trifluoroacetic acid can be used.

Water is preferably used as the solvent, to which, if desired, an inert cosolvent, e.g. Acetic acid or dimethyl sulfoxide is added.

Usually one works at temperatures from 0 to 150 ° C, preferably at the boiling point of the solvent.

As a rule, the carboxylic acids formed as intermediates cannot be isolated and usually decarboxylate spontaneously under the specified reaction conditions. Procedure D>

Oxidation of 2-benz (o) ylpyridines of the formula I {X = CH-CN} with (air) oxygen in the presence of a base {cf. e.g.

M.S. Kharasch and G. Sosnovsky, Tetrahedron 3_, 97 (1958);

H.G. Aurich, Tetrahedron Lett. H, 657 (1964);

S.S. Kulp, Org. Prep. and Proced. 2, 137 (1970);

A. Donetti et al. , Synthesis 1980, 1009;

J.F. Wolfe et al., J. Het. Chem. 2, 1061 (1987);

H. Yamanaka and S. Ohba, Heterocycles 31, 895 (1990)}:

I {X = CH-CN} I {X = CO}

The base comes e.g. the alkali metal hydrides, amides, carbonates and bicarbonates, and also nitrogen bases such as triethylamine, pyridine and 4-dimethylaminopyridine, into consideration. In addition, the alkali metal salts of bulky alcohols such as potassium tert. -butylate can be used.

Both protic, e.g. Alcohols such as methanol and ethanol, as well as dipolar aprotic solvents, e.g. Dimethyl sulfoxide or ethers such as tetrahydrofuran and dioxane.

The reaction is usually carried out at temperatures between 0 and 50 ° C, preferably at room temperature. If desired, the course of the reaction can be accelerated with a phase transfer catalyst such as triethylbenzylammonium chloride.

Procedure E>

Reduction of 2-benz (o) ylpyridines I {X = CO} with complex hydrides such as NaBH ₄ and LiAlH ₄ or by means of catalytic hydrogenation in the presence of a transition metal catalyst, for example Raney nickel or platinum / carbon, in a manner known per se {cf. e.g. C. Vaccher et al., J. Het. Chem. 2j5, 811-815 (1989); GR Newkome et al., J. Org. Chem. 41, 2961-2971 (1984); A. Garcia et al., Tetrahedron Lett. 14: 1797-1798 (1993); M. Takeshita et al. , Heterocycles 3_5_, 879-884 (1993); M. Takemoto et al., Chem. Pharm. Bull. .42., 802-805 (1994)}: I {X = CO} {X = CH-OH}

Process products I with X = CH-OH can then in the presence of a base with alkyl halides X- (Cχ-C-alkyl), wherein

X represents chlorine, bromine or iodine, are alkylated {cf. e.g.

D.E. Beattie et al., J. Med. Chem. 2_0, 714-718 (1977);

J. Crosby et al. , Tetrahedron Lett. 3JL 3849-3852 (1989);

S. Jriuchijima et al., J. Am. Chem. Soc. 9L, 4280 (1974); S. Sakuraba et al., Tetrahedron: Asymmetry 4 _. , 1457-1460 (1993);

Ya.G. BaL'on et al., Ükr. Khim. Zh. (Russ. Ed.) 5_7_, 191-195

(1991)}:

{X = CH-OH} I {X = CH-0 (Cχ-C ₄ alkyl)}

As bases come e.g. the alkali metal hydroxides such as sodium hydroxide, the alkali metal hydrides such as sodium hydride, the alkali metal amides such as sodium amide or the alkali metal salts of alcohols such as potassium tert. -butylate into consideration.

As a rule, one works in an inert solvent / diluent, both dipolar aprotic solvents, e.g. N, N-dimethylformamide, dimethyl sulfoxide or ethers such as diethyl ether, tetrahydrofuran and 1,4-dioxane, as well as protic solvents, e.g. Alcohols such as tert. -Butanol.

The reaction is normally carried out at a reaction temperature of 0 to 150 ° C, preferably at 20 to 100 ° C. Procedure E)

Nucleophilic benzoylation of halopyridines of the formula IV with benzaldehydes V in the presence of a base and a catalyst {cf. e.g. H. Stetter, Angew. Chem. 33: 695 (1976);

A. Miyashita et al. Chem. Pharm. Bull. 38 / 1147-1152 (1990) A. Miyashita et al. ibid 4H, 43-48 and 2627-2631 (1992);

IV VI {X = CO}

{Shark = CI, Br, J}

For example, the alkali metal hydrides such as sodium hydride or the alkali metal amides such as sodium amide can be used as bases.

Suitable solvents are e.g. dipolar aprotic solvents, e.g. N, N-dimethylformamide, dimethyl sulfoxide or cyclic ethers such as tetrahydrofuran and 1,4-dioxane.

In particular, (substituted) (benz) imidazolium salts and (substituted) (benz) thiazolium salts, e.g. 1,3-dimethylimidazolium chloride, 1,3-dimethylimidazolium bromide, 1,3-dimethylimidazolium iodide, 1,3-benzimidazolium chloride, 1,3-benzimidazolium bromide and 1,3-dimethylbenzimidazolium iodide.

The amount of the catalyst can be up to 50%, preferably 5 to 20%, based on the molar amount of the halopydridine used.

The reaction is usually carried out at temperatures from 0 to 150 ° C., preferably at temperatures from 20 to 100 ° C. Procedure G)

Reaction of halopyridines IV with benzyl magnesium halides VI or benzyl zinc halides VII, if appropriate in the presence of a transition metal catalyst {cf. e.g. I E. Negishi et al., J. Org. Chem. 41, 1821 (1977) and M. Kumada et al., Tetrahedron Lett. 21, 845 (1980)}:

VI {M = Mg} I {X = CH ₂ ; VII {M = Zn} n = 0}

The compounds VI and VII can easily be prepared from the corresponding benzyl halides and magnesium or zinc, for example according to M. Gaudemar, Bull. Soc. Chim. Fr., 1962, p. 974.

Suitable catalysts are in particular nickel catalysts, for example Ni [P (phenyl) ₃ ] ₄ or Ni [P (phenyl) ₃ ] ₂ C1 ₂ , and palladium catalysts, for example Pd [P (phenyl) ₃ ] ₄ , Pd [ P (phenyl) ₃ ] C1, Pd [1,2-bis (diphenylphosphino) ethane] Cl ₂ , Pd [1,4-bis (diphenylphosphino) butane] Cl ₂ or Pd [1,1 'bis - (diphenylphosphino) ferrocene] CI.

The reaction is usually carried out in an inert organic solvent, e.g. in an ether such as diethyl ether and tetrahydrofuran.

Usually one works at 0 to 150 ° C, preferably at 20 to 100 ° C.

Procedure H)

Oxidation of substituted 2 -benz (o) ylpyridines of the formula I, in which n is zero, in a manner known per se {cf. e.g.

A. Albini and S. Pietra, Heterocyclic N-Oxides, CRC-Press Inc.,

Boca Raton, USA 1991; H.S. Mosher et al. , Org. Synth. Coll. Vol. IV, 1963, p. 828;

E.C. Taylor et al. , Org. Synth. Coll. Vol. IV, 1963, p. 704;

T.W. Bell et al., Org. Synth. ££, 226 (1990)}:

Oxidation I {n = 0} ► I {n = 1} Among the oxidizing agents customary for the oxidation of the pyridine ring, reference may be made, for example, to peracetic acid, pertrifluoroacetic acid, perbenzoic acid, m-chloroperbenzoic acid, monopermaleic acid, magnesium monoperphthalate, sodium perborate, oxones (contains peroxidisulfate), tungsten acid and hydrogen peroxide.

Suitable solvents are e.g. Water, sulfuric acid, carboxylic acids such as acetic acid and trifluoroacetic acid and halogenated hydrocarbons such as dichloromethane and chloroform.

The oxidation is usually successful at temperatures from 0 ° C to the boiling point of the reaction mixture.

The oxidizing agent is normally used in at least equimolar amounts, based on the starting compound. In individual cases, a large excess of oxidizing agent can also offer advantages.

Unless otherwise stated, all of the processes described above are expediently carried out at atmospheric pressure or under the autogenous pressure of the respective reaction mixture.

The reaction mixtures are generally worked up in a manner known per se. Unless stated otherwise in the processes described above, the valuable products are obtained e.g. after dilution of the reaction solution with water by filtration, crystallization or solvent extraction, or by removing the solvent, distributing the residue in a mixture of water and a suitable organic solvent and working up the organic phase onto the product.

The substituted 2-benz (o) ylpyridines I can be obtained in the preparation as isomer mixtures which, however, if desired, can be separated into the largely pure isomers if desired by the customary methods such as crystallization or chromatography, including on an optically active adsorbate. Pure optically active isomers can advantageously be prepared from corresponding optically active starting products.

Agricultural salts of the compounds I can be reacted with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride, or by reaction with an acid of the corresponding anion, preferably the Hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid are formed.

Salts of I, the metal ion of which is not an alkali metal ion, can also be prepared in a conventional manner by salting the corresponding alkali metal salt, as can ammonium, phosphonium, sulfonium and sulfoxonium salts using ammonia, phosphonium, sulfonium or sulfoxonium hydroxides.

The compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides. The herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.

Taking into account the versatility of the application methods, the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants. For example, the following crops are suitable: Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea libericaus), Cucumodison , Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoealumisisumisum , Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus eommunis, Ribes sylvestre, Ricinus eommunis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (see vulgar), Theobroma cacao, Trifolium pr atense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods. The substituted 2-benz (o) ylpyridines I are also suitable for the desiccation and / or defoliation of plants.

As desiccants, they are particularly suitable for drying out the above-ground parts of crops such as potatoes, rapeseed, sunflower and soybeans. This enables a fully mechanical harvesting of these important crops.

Also of economic interest is the ease of harvesting, which is made possible by the temporally concentrated decrease or decrease in the adhesive strength on the tree in the case of citrus fruits, olives or other types and varieties of pome, stone and nuts. The same mechanism, that is to say the promotion of the formation of separating tissue between the fruit or leaf and shoot part of the plants, is also essential for a well controllable defoliation of useful plants, in particular cotton.

In addition, the shortening of the time interval in which the individual cotton plants ripen leads to increased fiber quality after the harvest.

The compounds I or the compositions comprising them can be, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, and also high-strength aqueous, oily or other suspensions or dispersions, emulsions,

Oil dispersions, pastes, dusts, sprinkles or granules by spraying, atomizing, dusting, scattering or pouring can be used. The application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.

The following are essentially considered as inert auxiliaries: mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. to

Preparation of emulsions, pastes or oil dispersions can use the substituted 2-benz (o) ylpyridines I as such or in an oil or solvent dissolved, can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, it is also possible to prepare concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.

The alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl polyglycol ether, alkyl aryl polyether alcohols, isotridecyl ethoxylated, polyethylenethoxy alcohol, fatty alcohol alcohol, fatty alcohol Polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol ester, lignin sulfite waste liquor or methyl cellulose.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.

Granules, e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers. Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite and diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate and ammonium nitrate , Urea and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.

The concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range. In general, the formulations contain about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient I. The active ingredients are in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum). The following formulation examples illustrate the preparation of such preparations:

I. 20 parts by weight of compound no. 2 are dissolved in a mixture which is alkylated from 80 parts by weight

Benzene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide in 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide in 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.

II. 20 parts by weight of compound no. 108 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide on 1 Mole of castor oil consists. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.

III. 20 parts by weight of active ingredient no. 118 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.

IV. 20 parts by weight of active ingredient no. 460 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active ingredient.

V. 3 parts by weight of active ingredient No. 369 are mixed with 97 parts by weight of finely divided kaolin. In this way, a dusting agent is obtained which contains 3% by weight of the active ingredient. VI. 20 parts by weight of active ingredient No. 470 are with

2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic

Mineral oil mixed intimately. A stable oily dispersion is obtained.

VII. 1 part by weight of compound no. 490 is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. The mixture can then be diluted with water to the desired active ingredient concentration. A stable emulsion concentrate is obtained.

.. VIII 1 part by weight of compound No. 491 is dissolved in a mixture containing 31 (= nonionic emulsifier based on ethoxylated castor oil; BASF AG) 80 parts by weight of cyclohexane and 20 parts by weight of Wettol ^® EM consists. Then it can be diluted with water to the desired active ingredient concentration. A stable emulsion concentrate is obtained.

The active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).

The application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.) depending on the control target, the season, the target plants and the growth stage.

To broaden the spectrum of activity and to achieve synergistic effects, the substituted 2-benz (o) yl-pyridines I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together. For example, 1, 2, 4-thiadiazoles, 1, 3, 4-thiadiazoles, amides, aminophosphoric acid and their derivatives, aminotriazoles, anilides, aryloxy / heteroaryloxyalkanoic acids and their derivatives, benzoic acid and their derivatives, benzothiadiazinones, 2- (Hetaroyl / aroyl) -1, 3 -cyclohexane diones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF ₃ - phenyl derivatives, carbamates, quinolinecarboxylic acids and their derivatives, chloroacetanilides, cyclohexane-1, 3-dione derivatives, diazines, dichloropropionic acid and their derivatives, dihydrobenzuranofurane-3-one, dihydrobenzane furansane , Dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3, 4, 5, 6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryl ester phenoxy - Acetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and their derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and üracile into consideration.

It may also be useful to apply the compounds I alone or in combination with other herbicides, mixed with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used to remedy nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.

Manufacturing examples

Example 1: 3-Chloro-2 - [1- (4-chlorophenyl) -1-cyanomethyl] -5- trifluoromethylpyridine (Method A)

1.65 g of an 80% suspension of sodium hydride in mineral oil was washed with 30 ml of anhydrous N, N-dimethylformamide to remove the mineral oil. 25 ml of N, N-dimethylformamide were added to the sodium hydride obtained, after which a solution of 7.6 g of 4-chlorobenzyl cyanide in 25 ml of N, N-dimethylformamide was added dropwise within 20 minutes. It was created under

Gas evolution a red suspension, which was stirred for a further 15 minutes. Subsequently, 10.8 g of 2,3-dichloro-5-trifluoromethylpyridine were added dropwise to the reaction mixture in the course of 20 minutes with an exothermic reaction. After the addition had ended, the mixture was stirred for a further 20 minutes and the reaction mixture was then stirred into 2 l of water. The product was extracted with three times 200 ml of tert from the aqueous phase. Butyl methyl ether. The combined organic phases were finally dried over magnesium sulfate and then concentrated. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane / ethyl acetate = 4: 1). Yield: 6.9 g (42%) of a colorless oil; ^! H-NMR (270 MHz; in CDC1 ₃ ): δ [ppm] = 5.78 (s, 1H), 7, 36 (d, 2H),

7.45 (d, 2H), 7.98 (s, 1H), 8.84 (s, 1H).

Example 2: 3-Chloro-2 - [1- (2,3-dichlorophenyl) -1-cyanomethyl] -5-trifluoromethylpyridine (Process A)

Analogously to Example 1, 10.0 g of a colorless oil were obtained from 1.65 g of sodium hydride suspension, 9.3 g of 2,3-dichlorobenzyl cyanide and 10.8 g of 2,3-dichloro-5-trifluoromethylpyridine. Yield: 55%;

1H-NMR (400 MHz; in CDC1 ₃ ): δ [ppm] = 6.20 (s, lH), 7.30 (t, lH), 7.50-7.56 (m, 2H), 8, 03 (s, lH), 8.78 (s, lH).

Example 3: 2 - [1-Carbamoy1 - 1 - (4-chlorophenyl) methyl] -3-chloro-5-trifluoromethylpyridine (Method B)

6.0 g of 3-chloro-2 - [1- (4-chlorophenyl) -1-cyanomethyl] -5-trifluoromethylpyridine (prepared according to Example 1) were stirred in 30 ml of 96% sulfuric acid at 23 ° C. for 16 hours. The reaction mixture was then carefully stirred into 200 ml of ice-water, the product crystallizing out. The solid was separated, washed successively with water and n-hexane and then dried. Yield: 5.5 g (87%) of colorless crystals; M.p .: 135-136 ° C.

Example 4: 3-Chloro-2 - [1- (4-chlorophenyl) -1-methoxycarbonylmethyl] -5-trifluoromethylpyridine (Method B)

In a solution of 3.0 g of 2 - [1-carbamoyl-l- (4-chlorophenyl) methyl] -3-chloro-5-trifluoromethylpyridine (prepared according to Example 3) in 100 ml of anhydrous methanol was hydrogen chloride gas for 5 hours initiated. The mixture was then stirred for a further 16 hours, during which excess hydrogen chloride was removed by introducing nitrogen. After the methanol had been separated off, the crude product was purified by chromatography on silica gel (mobile phase: cyclohexane / tert-butyl methyl ether = 50: 1). Yield: 1.3 g (42%) of colorless crystals; M.p .: 103-104 ° C.

Example 5: 3-Chloro-2 - (4-chlorobenzyl) -5-trifluoromethylpyridine (Process C)

4.3 g of 3-chloro-2- [1- (4-chlorophenyl) -1-cyanomethyl] -5-trifluoromethylpyridine (prepared according to Example 1) were refluxed in 50 ml of 47% aqueous hydrogen bromide solution for 3 hours heated and then stirred at 23 ° C for 68 hours. The mixture was then poured into 500 ml of ice water. After stirring for a further 30 minutes, the resulting solids content separated, washed with water and finally dried. Yield: 3.0 g (75%) of colorless crystals; M.p .: 54-56 ° C).

Example 6: 3 -Chlor -2- (2, 3 -dichlorobenzyl) -5- trifluoromethylpyridine (Process C)

Analogously to Example 5, 6.3 g of a colorless oil were obtained from 7.9 g of 3-chloro-2 - [1- (2,3-di-chlorophenyl) -1-cyanomethyl] -5-trifluoromethylpyridine (prepared according to Example 2) . Yield: 86%; ^φ iH-NMR (270 MHz; in CDC1 ₃ ): δ [ppm] = 4.50 (s, 2H), 7.02 (d, lH), 7.15 (t, lH), 7.40 (d , lH), 7.93 (s, lH), 8.67 (s, lH).

Example 7: 3-Chloro-2 - (4-chlorobenzoyl) -5-trifluoromethylpyridine

3.0 g of an 80% suspension of sodium hydride in mineral oil was washed with anhydrous dioxane to remove the mineral oil. To the sodium hydride obtained was added first 100 ml of dioxane and then, under a nitrogen atmosphere, 21.6 g of 2,3-dichloro-5-trifluoromethylpyridine, 14.1 g of p-chlorobenzaldehyde and 2.24 g of 1,3-dimethylimidazolium iodide in succession. This reaction mixture was stirred at 50 ° C for one hour and at 23 ° C for 65 hours. For working up, the mixture was diluted with 200 ml of water, after which it was concentrated to half the volume. The product was then extracted with three times 50 ml of methylene chloride. The combined organic phases were washed with 50 ml of water, dried over sodium sulfate and finally concentrated. The crude product was cleaned by means of vacuum distillation. Yield: 22.4 g (70%) of a yellow liquid; Boiling range: 126-139 ° C / 0.65 mbar; Purity: 95%; iH-NMR (270 MHz; in CDC1 ₃ ): δ [ppm] = 7.48 (d, 2H), 7.79 (d, 2H), 8.12 (S, 1H), 8.83 (S, 1H).

Example 8: 3-Chloro-2 - (4-chlorobenzoyl) -5- trifluoromethylpyridine (Method D)

A solution of 2.0 was added to a solution of 2.0 g of 3-chloro-2 - [1- (4-chlorophenyl) -1-cyano-methyl] -5-trifluoromethylpyridine (prepared according to Example 1) in 20 ml of dimethyl sulfoxide Potassium carbonate was added to 3 ml of water, after which the mixture was stirred at 23 ° C. for three days with air. For working up, the reaction mixture was poured into 200 ml of water. Thereafter, the valuable product was extracted with three times 80 ml of tert. Butyl methyl ether. The combined organic phases were washed twice with 50 ml of water each time, dried over sodium sulfate and finally concentrated. The black oil obtained was cleaned by means of

Kugelrohr distillation under vacuum. Yield: 1.2 g (62%) of a light yellow oil; Boiling range: 110-120 ° C (0.3 mbar); ^ ^• H-NMR see Ex. 7.

Example 9: 3-Chloro-2 - (4-chlorobenzoyl) -5- trifluoromethylpyridine (process A + D)

16.5 g of an 80% suspension of sodium hydride in mineral oil were washed with anhydrous N, N-dimethylformamide to remove the mineral oil. The sodium hydride was then mixed with 100 ml of N, N-dimethylformamide and then dropwise with a solution of 37.9 g of 4-chlorobenzyl cyanide in 100 ml of N, N-dimethylformamide (exothermic). After the addition had ended, the mixture was stirred for a further 15 minutes. Subsequently, 54.0 g of 2,3-dichloro-5-trifluoromethylpyridine were added dropwise to the reaction mixture, which heated up strongly and was kept at about 50 ° C. by external cooling. After the addition had ended, the mixture was stirred at 23 ° C. for a further 20 hours. Air (dried over Blaugel) was then passed through the mixture for 4 days. For working up, the reaction mixture was poured into 600 ml of ice water. The product of value was then extracted with three 200 ml portions of tert. Butyl methyl ether. The combined organic phases were washed twice with 100 ml of water each time, dried over sodium sulfate and finally concentrated. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane / tert-butyl methyl ether = 9: 1). Yield: 50.1 g (62%) of a light yellow oil; Purity (GC): 94.6%; ⁱ H-NMR see Example 7.

Example 10: 3-Chlorine -2 - [1- (4-chlorophenyl) -1-hydroxymethyl] -5-trifluoromethylpyridine (Method E)

0.36 g of sodium borohydride was added in portions with ice-cooling to a solution of 6.0 g of 3-chloro-2 - (4-chlorobenzoyl) -5-trifluoromethylpyridine in 10 ml of anhydrous ethanol. After stirring for 20 hours at 23 ° C., 50 ml of 10% hydrochloric acid were carefully added dropwise to the reaction mixture. The ethanol was then evaporated. The product was then extracted with three times 30 ml of tert. Butyl methyl ether. The combined organic phases were dried over sodium sulfate and then concentrated. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane / tert-butyl methyl ether = 9: 1). Yield: 3.6 g (60%) of a colorless oil;

^X H-NMR (270 MHz; in CDC1 ₃ ): δ [ppm] = 5.02 (d, 1H), 6.02 (d, 1H), 7.33-7.41 (m, 4H), 7 , 91 (s, 1H), 8.81 (s, 1H). Example 11: 3-Chloro-2- [1- (4-chlorophenyl) -1-methoxymethyl] -5-tri-fluoromethylpyridine (Method E)

0.2 g of an 80% suspension of sodium hydride in mineral oil was washed with anhydrous N, N-dimethylformamide to remove the mineral oil. First, the sodium hydride was mixed with 50 ml of N, N-dimethylformamide and then dropwise with a solution of 2.1 g of 3-chloro-2- [1- (4-chlorophenyl) -1-hydroxymethyl] -5-trifluoromethylpyridine 10 ml of N, N-dimethylformamide. The mixture was then stirred for a further 15 minutes. After dropwise addition of 1.1 g of methyl iodide, the mixture was stirred at 23 ° C. for a further 20 hours. The reaction mixture was then poured into 200 ml of ice water. The product was extracted with three times 70 ml of tert from the aqueous phase. -Butyl methyl ether. The combined organic phases were washed twice with 50 ml of water each time, dried over sodium sulfate and finally concentrated. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane / tert-butyl methyl ether = 100: 1). Yield: 1.1 g (50%) of a colorless oil. iH-NMR (270 MHz; in CDC1 ₃ ): δ [ppm] = 3.44 (s, 3H), 5.83 (s, lH), 7.33 (d, 2H), 7.48 (d, 2H), 7.90 (S, 1H), 8.85 (s, 1H).

Example 12: 3-Chloro-2- (4-chlorobenzoyl) -5- trifluoromethylpyridine (Method F)

21.6 g of 2,3-dichloro-5-trifluoromethylpyridine and 14.1 g of 4-chlorobenzaldehyde were added to a suspension of 3.0 g of sodium hydride (80% by weight suspension in mineral oil) in 100 ml of anhydrous dioxane with stirring and 2.24 g of 1,3-dimethylimidazolium iodide. The mixture was then stirred (under a nitrogen atmosphere) at 50 ° C. for 11 hours and then at 22 ° C. for 60 hours. After the reaction mixture had been diluted with 200 ml of water, the dioxane was largely distilled off under reduced pressure. The product was extracted from the residue with three times 100 ml of methylene chloride. The combined organic phases were washed with 50 ml of water, dried over sodium sulfate and finally concentrated. Distillation of the residue at 0.65 mbar (boiling range: 126-139 ° C) gave 22.4 g of a colorless oil. Yield: 70% (purity: approx. 95%); ⁱ H-NMR see Example 7. Example 13: 3-Chloro-2 - [1- (2,3-dichloro-4-ethoxyphenyl) -1-cyano-methyl] -5- trifluoromethylpyridine (Process A)

Precursor: 2,3-dichloro-4-methoxybenzyl bromide

55.0 g of 2,3-dichloroanisole were dissolved in 155 ml of glacial acetic acid at 30 ° C. and 9.6 g of paraformaldehyde were added. Then 65 ml of a 30% by weight solution of HBr in glacial acetic acid were added, and the mixture was then stirred at 90 ° C. for 5 hours. The reaction mixture was then allowed to cool and then poured into 800 ml of ice water. The crystallized crude product was separated off, washed with water and recrystallized from n-hexane. Yield: 21 g (78%) of white crystals; M.p .: 101-102 ° C.

Precursor: 2,3-dichloro-4-methoxybenzyl cyanide

A solution of 68 g of 2,3-dichloro-4-methoxybenzylbromide in 220 ml of dimethyl sulfoxide was added dropwise to a suspension of 15 g of anhydrous sodium cyanide in 250 ml of anhydrous dimethyl sulfoxide. The mixture was then heated to the reflux temperature for 5 hours under a nitrogen atmosphere. The cooled reaction mixture was poured into 1.5 l of ice water, after which the solid product formed was separated off, washed with water and purified by stirring with petroleum ether (at 40-60 ° C.). Yield: 51 g (94%) of white crystals; M.p .: 118-119 ° C.

Analogously to Example 1, using 38.9 g of 2,3-dichloro-5-trifluoromethylpyridine, 38.9 g of 2,3-dichloro-4-methoxybenzylnitrile, 5.95 g of an 80 wt. - Sodium hydride suspension in mineral oil and 220 ml dimethylformamide 39.2 g white crystals. Yield: 55%; M.p .: 174-176 ° C.

Example 14: 3-Chloro-2- [2,3-dichloro-4-hydroxybenzyl) -5-trifluoromethylpyridine (Method C)

Analogously to Example 5, 20 g of valuable product (white crystals) were obtained from 38 g of 3-chloro-2- [1 - (2, 3-dichloro-4-methoxyphenyl) -1-cyanomethyl] - 5-trifluoromethylpyridine. Yield: 60%; M.p .: 159-161 ° C.

Example 15: Methyl 2 - [2,3-dichloro-4- ([3-chloro-5-trifluoromethylpyridin-2-yl] methyl) phenoxy] acetic acid

2.0 g of 3-chloro-2- (2,3-dichloro-4-hydroxybenzyl) -5-trifluoromethyl-pyridine, 1.5 g of anhydrous potassium carbonate and 1.0 g of methyl bromoacetate were mixed in 60 ml of anhydrous dimethylformamide for 16 hours at 23 ° C stirred. Then the reaction mixture was poured in 400 ml ice water. The resulting solid product was separated, washed with water and purified by stirring in n-hexane. Yield: 2.4 g (100%; white crystals); M.p .: 110-111 ° C.

In addition to the compounds described above, Tables 1 and 2 also list further substituted 2-benz (o) ylpyridines I, which were likewise prepared or can be prepared by one of the processes described:

Table 1

- $?

45

Table 2

Examples of use (herbicidal activity)

The herbicidal activity of the substituted 2-benz (o) ylpyridines I was demonstrated by the following greenhouse tests:

Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels. The seeds of the test plants were sown separately according to species.

In pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles. The tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.

For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment. The application rate for post-emergence treatment was 0.125, 0.0625, 0.0078 or 0.0039 kg / ha a.S. (active substance).

The plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species. The trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.

Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.

The plants used in the greenhouse experiments are composed of the following types:

At application rates of 7.8 and 3.9 g / ha a.S. Compounds No. 118 and 369 showed very good herbicidal activity against Abutilon theophrasti, Solanum nigrum, Polygonum persicaria and Veronica spec.

Compound no.460 showed at application rates of 0.125 and 0.0625 kg / ha a.S. a very good selective herbicidal action against Abutilon theophrasti, Solanum nigrum and Veronica spec. in the soybean crop, which itself was little harmed.

Examples of use (desiccant / defolian effectiveness)

Young, 4-leafed (without cotyledons) cotton plants served as test plants, which were grown under greenhouse conditions (relative humidity 50 to 70%; day / night temperature 27/20 ° C.).

The young cotton plants were dripping wet ( 'relative the addition of 0.15 wt .-% of the fatty alcohol alkoxylate Plurafac LF 700 ^{® 1} on the spray mixture) treated with aqueous preparations of the active ingredients. The amount of water applied was the equivalent of 1000 l / ha. After 13 days, the number of leaves dropped and the degree of defoliation in% were determined.

No leaf fall occurred in the untreated control plants.

¹⁾ a foam-like, nonionic surfactant from BASF AG

Claims

claims

1. Substituted 2-benz (o) ylpyridines of the general formula I

R ³ R ⁴

in which the variables have the following meanings:

n 0 or 1;

X carbonyl, methylene, CH (C ₁ -C ₄ alkyl), CH-OH, CH-CN,

CH-halogen, C (halogen) ₂ , CH-CONH _2; CH-CO-0 (C ₁ -C ₄ alkyl), CH-0 (-C-C ₄ alkyl) or C (CN) (C ₁ -C ₄ alkyl);

R ¹ halogen, C1-C ₄ -haloalkyl, -CC alkylthio, -C-C ₄ alkyl sulfinyl or Ci -C ₄ alkyl sulfonyl;

R ^{2 is} hydrogen or halogen;

R ^{3 is} hydrogen, nitro, hydroxy, halogen or C ₁ -C ₄ alkoxy;

R ^{4 is} hydrogen, nitro, hydroxy, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or Ci -C ₄ alkoxy;

R ^{5 is} hydrogen, nitro, cyano, halogen, -CC ₈ alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, C ₃ -C ₈ cycloalkyl, Ci-Cs haloalkyl, C ₂ - C ₈ haloalkenyl, C-halo -C ₈ alkynyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ - alkyl, C -C ₄ alkenyloxy Cι-C ₄ alkyl, C ₂ -C ₄ - Alkynyloxy -CC ₄ - alkyl, -C ₄ -alkyl thio-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfonyl-Cχ-C ₄ -alkyl, Ci -C ₄ -alkylsulfonyl-Ci -C ₄ - alkyl, cyano -Ci - C ₈ alkyl, cyano-C ₂ -C ₈ - alkenyl, cyano-C ₃ -C ₈ - alkynyl, -OR ⁸ , -SR ⁸ , -SO-R ⁸ , - S0 ₂ -R ⁸ , -S0 ₂ C1, -N (R ⁹ , R ¹⁰ ), -NH-SO ₂ - (-Cι-C ₈ -alkyl), -N [-S0 ₂ - (C ₁ -C ₈ - Alkyl)] ₂ , -NtCi-Ca-alkyl) [-S0 ₂ - (Ci-Ca-alkyl)], -S0 ₂ -N (R ⁹ , R ¹ °),

-N (R ¹¹ ) -CO-R ¹² , -NH-CO-OR ⁸ , -0-CO-NH-R ⁹ , -O-CO-R ¹² , -NH-CO-NH-R ⁹ , -O -CS-NH ₂ , -0-CS-N (-CC ₈ alkyl) ₂ , -CO-OR ⁸ , -CO-N (R ⁹ , R ¹⁰ ), -CS-N (R ⁹ , R ¹⁰ ), -CO-NH- S0 ₂ - (C _! -C ₄ -alkyl), -CO-N (-C-C ₄ -alkyl) -S0 ₂ - (-C-C ₄ -alkyl), -CO-R ¹² , Hydroxy carbonyl -C ₈ alkyl, (C ₈ alkoxy) carbonyl -C ₆ alkyl, -CH ₂ -CH (halogen) -CO-OR ⁸ , -CH ₂ -CH (halogen) -CO-N (R ⁹ , R ¹⁰ ), -CH ₂ -CH (halogen) -CN, -CH ₂ -CH (Halogen) -CO- (C ₁ -C ₄ -alkyl), -CH = C (halogen) -CO-OR ⁸ , -CH = C (-CC ₄ -alkyl) -CO-OR ⁸ , -CH = N-OR ¹³ , -C (R ¹ ) = N-OR ¹³ , -CH (-YR ¹⁵ , -ZR ¹⁵ ), -C (R ¹⁴ ) (-YR ¹⁵ , -ZR ¹⁵ ),

> where

for hydrogen, -CC ₈ alkyl, C ₃ -C ₈ cycloalkyl,

Cι-C ₈ haloalkyl, cyano-Cι-C ₈ alkyl, C ₁ -C ₄ alkoxy C ₁ -C ₄ alkyl, Ci-C -alkylthio-C ₁ -C ₄ alkyl, C ₄ -C -Alkylsulfinyl -Ci -C ₄ alkyl, Ci -C -alkylsulfonyl -Ci -C ₄ - alkyl, C ₃ -C ₈ alkenyl, C ₅ -C ₈ cycloalkenyl, C ₃ -C ₈ haloalkenyl, C ₃ - C ₈ -alkynyl, hydroxycarbonyl-Ci-C ₄ -alkyl, (Ci-C ₈ -alkoxy) carbonyl-Ci-C _δ -alkyl, (C ₃ -C ₈ -alkenyloxy) - carbonyl-Ci-Cε-alkyl, ( C ₃ -C ₈ alkynyloxy) carbonyl -Cχ-C ₆ -alkyl, -C-C ₄ -alkoxy- (Ci-C ₄ -alkoxy) carbonyl -Cι-C ₄ -alkyl, (Ci-C ₈ -haloalkoxy) carbonyl -Ci Ce alkyl, (C ₃ -C ₈ cycloalkyloxy) carbonyl -Ci Cβ alkyl, (Ci-C ₄ alkoxy) carbonyl - (Ci -C ₄ alkoxy) carbonyl -C ₁ -C _4- alkyl, (C ₃ -C 6 alkenyloxy) carbonyl- (Ci-C ₄ alkoxy) carbonyl -C ₁ -C ₄ alkyl,

(C ₃ -C _δ alkynyloxy) carbonyl - (Ci-C ₄ alkoxy) carbonyl - Ci-C ₄ alkyl, hydroxycarbonyl - (Ci -C ₄ alkoxy) carbonyl - Ci-C ₄ alkyl, oxetane-3 -yloxycarbonyl -Ci -C ₄ alkyl, phenoxycarbonyl -C ₁ -C ₄ alkyl, benzyl or benzyloxycarbonyl -C ₁ -C ₄ alkyl, the phenyl rings of the last 3 radicals each being unsubstituted or having one to three substituents can, each selected from the group consisting of nitro, cyano, hydroxy, hydroxycarbonyl, halogen, -CC ₄ alkyl, C ₁ -C ₄ haloalkyl, -C-C ₄ alkoxy, -C-C ₄ haloalkoxy, (Cι -C ₄ alkoxy) carbonyl and (-C-C ₄ alkoxy) carbonyl -C ₁ -C ₄ - alkoxy;

CH (R ²² ) CO N (R ⁹ , R ¹⁰ ), CH (R ²² ) CO R ²³ , N OR ¹³ CH (R ²² ) CR ²³ , CH (R ²² ) CO CO OR ²³ , N OR ¹³

CH (R ²² ) C CO OR ²³ ,

CH (R ²² ) CO N OR ²⁵

CH (R ²² ) CO OR ²³ CH (R ²² ) COCH (R ²² ) CO OR ²³

N OR ²⁵

R ⁹ , R ¹⁰ independently of one another for hydrogen, -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, Ci-Cβ -haloalkyl, Cι-C -Alkoxy -CC ₄ alkyl, -C ₄ alkyl thio-Ci -C ₄ alkyl, Ci -C -alkylsfinyl -Ci -C ₄ alkyl, -C-C ₄ alkylsulfonyl -CC ₄ -alkyl, cyano -Cι-C ₈ -alkyl, hydroxycarbonyl -Ci -C ₄ - alkyl, (Ci -C ₄ alkoxy) carbonyl -Ci -C ₄ - alkyl, (C ₃ -C ₇ cycloalkyloxy) carbonyl - Ci -C ₄ alkyl, (Ci -C ₄ alkoxy) carbonyl -C ₃ -C ₇ cycloalkyl, -C-C ₄ alkoxy-

(Ci -C ₄ - alkoxy) carbonyl -C -C alkyl, -C ₆ alkoxy, phenyl or phenyl -C ₁ -C ₄ alkyl, the phenyl rings of the last two radicals being unsubstituted or having one to three substituents can, each selected from the group consisting of nitro, cyano, hydroxy, halogen, C1-C ₄ -haloalkyl, -C-C ₄ alkoxy, -C ~ C ₄ -haloalkoxy, (Cι-C ₄ alkoxy) carbonyl and (Cι -C alkoxy) carbonyl - Cχ-C ₄ alkoxy

or R ⁹ and R ¹⁰ together for a tetramethylene, pentamethylene or ethyleneoxyethylene chain, which can each carry a hydroxycarbonyl group or a (Ci-Cε-alkoxy) carbonyl radical;

R ^{11 is} hydrogen, C] .- Ca alkyl, C ₃ -C ₈ alkenyl or C ₃ -C ₈ alkynyl; R ¹² , R ¹³ independently of one another for hydrogen, -C ₈ alkyl, C ₃ -C ₈ alkenyl, C ₃ -Ca alkynyl, C ₈ -C haloalkyl, Ci -C alkoxy-Ci -C - alkyl , (Ci -C -alkoxy) carbonyl - Ci -C ₄ - alkyl, C ₃ -C ₈ cycloalkyl, phenyl or phenyl -C ₁ -C ₄ - alkyl, the phenyl rings of the last two radicals being unsubstituted or one to three may carry substituents, each selected from the group consisting of nitro, cyano, hydroxy, hydroxycarbonyl, halogen, C ₁ -C ₄ haloalkyl, Cι-C ₄ alkoxy, C ₁ -C ₄ -haloalkoxy, (C ₁ -C ₄ -Alkoxy) carbonyl and (C1-C ₄ -alkoxy) carbonyl -

C ₁ -C ₄ alkoxy;

R ^{14 is} Ci -C ₈ alkyl;

Y, Z independently of one another for oxygen or sulfur;

R ¹⁵ is Cι-C ₈ -alkyl, C ₈ haloalkyl or C ₁ -C ₄ alkoxy Cι-C alkyl;

i6. 2i independently hydrogen, cyano, C ₈ alkyl, Ci- C ₄ -alkoxy-C ₁ -C ₄ - alkyl, _Cι-C8 alkoxy, Ci - C _{4 alkoxy-Ci-C4} alkoxy , Hydroxycarbonyl, (-C ₈ alkoxy) carbonyl, aminocarbonyl, (C ₃ -C ₈ alkyl) aminocarbonyl or di (-C ₈ alkyl) aminocarbonyl;

_R 22. _R 25 independently of one another for hydrogen, Cχ-C ₈ alkyl, Ci - C ₄ alkoxy -CC-alkyl, C ₃ -C ₈ alkenyl or C ₃ -C ₈ alkynyl

and R ²⁶ -R ^{28 are} independently hydrogen or -CC ₈ alkyl;

R ^{6 is} hydrogen, nitro, halogen, -OR ²⁹ or -CO-OR ²⁹ and R ^{7 is} hydrogen, nitro, halogen or -OR ³⁰ , where

R ²⁹ and R ³⁰ each represent one of the meanings of R ⁸ ,

and the agriculturally useful salts of the compounds I, with the exception of those compounds I in which X is methylene, and

R ^{5 is} -OR ⁸ and R ³ and R ^{7 are} both hydrogen or

R ¹ for halogen and R ³ , R ⁴ , R ⁶ and R ⁷ all simultaneously represent hydrogen.

2. Substituted 2 -Benz (o) ylpyridines of the formula I according to

Claim 1, wherein the variables have the following meanings:

n zero;

X carbonyl or methylene;

R ¹ Ci-C ₄ haloalkyl;

R ² , R ³ , R ⁴ independently of one another halogen;

R ⁵ -OR ⁸ , -CO-OR ⁸ , -CO-N (R ⁹ , R ¹⁰ ) or -CH = N-OR ¹³ ;

R ⁶ , R ^{7 are} hydrogen or halogen;

R ^{8 is} hydrogen, -CC ₈ alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, hydroxycarbonyl - Ci - C ₄ - alkyl, (Ci - C ₈ alkoxy) carbonyl - Ci - C ₆ - alkyl, (C ₃ - C ₈ - alkenyloxy) carbonyl - Ci - C ₆ - alkyl, (C ₃ - C ₈ - alkynyloxy) carbonyl - Ci - Cζ - alkyl, Ci - C - alkoxy - (Ci - C ₄ - alkoxy) carbonyl -Cι-C ₄ - alkyl, (Ci -C ₄ alkoxy) - carbonyl - (Ci - C ₄ - alkoxy) carbonyl - Ci - C ₄ - alkyl,

CH (R ²² ) CO N (R ⁹ , R ¹⁰ ), CH (R ²² ) CO CO OR ²³ ,

N OR ¹³

CH (R ²² ) C CO OR ²³

CH (R ²² ) CO N OR ²⁵ or CH (R ²² ) CO OR ²³

CH (R ²² ) C OCH (R ²² ) CO OR ²³

II '

N OR ²⁵

R ⁹ , R ¹⁰ independently of one another hydrogen, -CC ₈ alkyl or

(Ci - C ₄ alkoxy) carbonyl - Ci - C ₄ alkyl; R ^{13 is} hydrogen, -CC ₈ alkyl, C ₃ -C ₈ -alkenyl, C ₃ -C ₈ -alkynyl or (C ₁ -C ₄ -alkoxy) carbonyl -CC ₄ -alkyl;

_{22/23 #R} 25 independently of one another are hydrogen, C ₈ alkyl, C ₃ -C ₈ -alkenyl or C ₃ -C ₈ alkynyl.

3. Use of the substituted 2-benz (o) ylpyridines of the formula I and the agriculturally useful salts of I, according to claim 1, as herbicides or for the desiccation and / or defoliation of plants.

4. Herbicidal composition containing a herbicidally effective amount of at least one substituted 2-benz (o) ylpyridine of the formula I or an agriculturally useful salt of I, according to claim 1, and at least one inert liquid and / or solid carrier and, if desired, at least one surface-active Material.

5. Agent for the desiccation and / or defoliation of plants, containing a desiccant and / or defoliant effective amount of at least one substituted 2-benz (o) ylpyridine of the formula I or an agriculturally useful salt of I, according to claim 1, and at least one inert liquid and / or solid carrier and, if desired, at least one surface-active substance.

6. A process for the preparation of herbicidally active agents, characterized in that a herbicidally effective amount of at least one substituted 2-benz (o) ylpyridine of the formula I or an agriculturally useful salt of I, according to claim 1, and at least one inert liquid and / or solid carrier and, if desired, mixes at least one surface-active substance.

7. A process for the preparation of desiccant and / or defoliant agents, characterized in that a desiccant and / or defoliantly effective amount of at least one substituted 2-benz (o) ylpyridine of the formula I or an agriculturally useful salt of I, according to claim 1, and at least one inert liquid and / or solid carrier and, if desired, at least one surfactant.

8. A method for controlling unwanted vegetation, characterized in that a herbicidally effective amount of at least one substituted 2-benz (o) ylpyridine of the formula I or an agriculturally useful salt

5 of I, according to claim 1, on plants, their habitat or on seeds.

9. A process for the desiccation and / or defoliation of plants, characterized in that a desiccant and / or

10 defoliantly effective amount of at least one substituted

2-Benz (o) ylpyridins of formula I or an agriculturally useful salt of I, according to claim 1, can act on plants.

15 10. The method according to claim 9, characterized in that cotton is treated.

11. A process for the preparation of substituted 2-benz (o) yl-pyridines of the formula I according to claim 1, in which X is 20 methylene or CH-CN, characterized in that substituted pyridines of the formula II

in the presence of a base with benzyl nitriles of the formula III

30 R ³ R ⁴

III

R ⁷ R ⁶

35 reacted and the process product I with X = CH-CN if necessary saponified and decarboxylated using aqueous acid.

40

45