DE19633751A1 - Substituted 2-arylpyridines - Google Patents

Abstract

Substituted 2-arylpyridine of formula (I) and salts thereof. In said formula (I), R<1> = SH, SO2OH, SO2C1, SO2NH2, C1-C6-Alkylthio, C1-C6-Alkyl sulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylamino-sulfonyl, Di(C1-C6-alkyl)aminosulfonyl; R<2>, R<3> = H, halogen; R<4> = H, C1-C6-alkyl, C1-C6-halogenalkyl, cyano-C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C4-halogen-alkoxy-C1-C4-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6 alkyl sulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C3-alkoxy-C1-C3-alkoxycarbonyl-C1-C6-alkyl, C2-C4-alkenyloxy-C1-C4-alkyl, C3-C4-alkinyloxy-C1-C4-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkyl, C3-C7-cycloalkyloxy-C1-C6-alkyl, C3-C7-cycloalkylthio-C1-C6-alkyl, C3-C8-alkenyl, C3-C8-alkinyl, C3-C8-halogenalkenyl, C3-C8-halogenalkinyl, C1-C6-alkoxy-C3-C8-alkenyl, C1-C6-alkoxy-C3-C8-alkinyl, C1-C6-alkylcarbonyl, C1-C6-alkylsulfonyl, C3-C6-alkenyloxy, C3-C6-alkinyloxy or eventually substituted benzyl; X = -O-, -S-, -NH-, -N(CH3)-, -CH2-; Y = chemical bond, -CO-, C(R<5>,R<6>); R<5>,R<6> = H, NO2, CN, OCH3, SCH3, halogen, C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxycarbonyl, C2-C6-alkenyl, C3-C6-alkinyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl. Application as herbicide; for plant desiccation/defoliation.

Description

The present invention relates to new substituted 2-aryl pyridines of formula I.

in which the variables have the following meanings:
n zero or 1;
R¹ mercapto, hydroxysulfonyl, chlorosulfonyl, aminosulfonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylaminosulfonyl or di- (C₁-C₆-alkyl) aminosulfonyl;
R², R³ independently of one another are hydrogen or halogen;
R⁴ hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, cyano-C₁-C₆- alkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₄-halogen alkoxy-C₁- C₄-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkyl sulfinyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄ -alkoxy-C₁-C₄-alkyl, (C₁-C₆-alkoxy) carbonyl-C₁-C₆-alkyl, C₁-C₃-alkoxy- (C₁-C₃-alkoxy) carbonyl- C₁-C₆-alkyl, C₂-C₄-alkenyloxy -C₁-C₄-alkyl, C₃-C₄-alkynyloxy-C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₆-alkyl, C₃-C₇-cycloalkyloxy-C₁-C₆-alkyl, C₃-C₇-cycloalkyl thio-C₁-C₆-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl, C₃-C₈-haloalkenyl, C₃-C₈-haloalkynyl, C₁-C₆-alkoxy-C₃-C₈-alkenyl, C₁ -C₆-alkoxy-C₃-C₈-alkynyl, (C₁-C₆-alkyl) carbonyl, C₁-C₆-alkylsulfonyl, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy or benzyl, which are unsubstituted or on the phenyl ring can carry three substituents, each selected from the group consisting of nitro, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy) carbonyl;
X is oxygen, sulfur, -NH-, -N (CH₃) - or methylene;
Y is a chemical bond, carbonyl or C (R⁵) -R⁶, where
R⁵, R⁶ independently of one another for hydrogen, nitro, cyano, methoxy, methylthio, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, (C₁-C₄-alkoxy) carbonyl, C₂-C₆-alkenyl or C₃-C₆-alkynyl stand,
as well as the agriculturally useful salts of the compounds I with R 1 = hydroxysulfonyl.

The invention also relates to

• - The use of the compounds I as herbicides or Desiccation / defoliation of plants,
• - herbicidal agents and agents for desiccation and / or Defoliation of plants which the compounds I as contain effective substances,
• - Procedures to control unwanted plant growth and for the desiccation and / or defoliation of plants with the connections I,
• - Process for the preparation of the compounds I and of herbicidal agents and agents for desiccation and / or Defoliation of Plants Using Compounds I such as
• Intermediate products of the formulas X, XVI, XXXIa, XXXIb, XXXIIa, XXXIIc, XXXVIa, XXXVIb, XXXVIIa and XXXVIIb.

WO 95/02590 describes a large number of herbicidally active 2-phenylpyridines described. Under their general formula some of the present compounds I also coincide R¹ = C₁-C₄-alkylthio, but are in the publication as Individual compounds only those with a trifluoromethyl group in the 5-position of the pyridine ring.

Since the herbicidal action known from WO 95/02590 Connections regarding harmful plants are not always complete is satisfactory, the present invention lay new herbicidal effective connections as a task with which Combat unwanted plants even better than before to let. The task also extends to the provision new desiccant / defoliant connections.

Accordingly, the substituted 2-aryl pyridines of formula I with herbicidal activity and new intermediates products X, XVI, XXXIa, XXXIb, XXXIIa, XXXIIc, XXXVIa, XXXVIb, XXXVIIa and XXXVIIb found for their manufacture.  

Furthermore, herbicidal compositions have been found which the compounds I contain and have a very good herbicidal effect. Furthermore Processes for the preparation of these agents and processes for Control of undesired plant growth with the compounds I found.

Furthermore, it was found that the compounds I also for Desiccation / defoliation of plant parts are suitable for what Cultivated plants such as cotton, potato, rapeseed, sunflower, soy beans or broad beans, especially cotton and potatoes, in Come into consideration. In this regard, means of desiccation and / or defoliation of plants, process for producing them Means and methods for the desiccation and / or defoliation of Plants with the compounds I found.

The compounds of formula I can, depending on the substitution pattern contain one or more chirality centers and then lie as enantiomer or diastereomer mixtures. Subject of Invention are both the pure enantiomers or diastereomers as well as their mixtures.

The substituted 2-arylpyridines I with R¹ = hydroxysulfonyl can come in the form of their agriculturally useful salts lie, it usually does not depend on the type of salt arrives. In general, the salts come in from such bases Consider where the herbicidal activity compared to that free compound I is not adversely affected.

Particularly suitable salts are those of the alkali metals, preferably sodium and potassium salts, the alkaline earth metals, preferably calcium and magnesium salts, which are the transition metals, preferably zinc and iron salts, and ammonium salts, where the ammonium ion, if desired, one to four C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl substituents and / or one Can carry phenyl or benzyl substituents, preferably Diiso propylammonium, tetramethylammonium, tetrabutylammonium, tri methylbenzylammonium and trimethyl (2-hydroxyethyl) ammonium salts, furthermore phosphonium salts, sulfonium salts such as preferred as tri- (C₁-C₄-alkyl) sulfonium salts, and sulfoxonium salts such as preferably tri- (C₁-C₄-alkyl) sulfoxonium salts.

The for the substituents R¹ and R⁴ to R⁶ or as radicals on one Organic molecule parts called phenyl ring represent collection terms for individual lists of the individual groups members. All carbon chains, i.e. all alkyl, Haloalkyl, cyanoalkyl, alkylcarbonyl, alkoxy, halogen alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkyl  sulfonyl, alkylamino, alkenyl, haloalkenyl, alkenyloxy, Alkynyl, haloalkynyl and alkynyloxy parts can be straight chain or be branched. Halogenated substituents are preferred have one to five identical or different halogen atoms.

Halogen is fluorine, chlorine, bromine or Iodine, especially for fluorine or chlorine.

Furthermore, for example:

• - C₁-C₄-alkyl for: CH₃, C₂H₅, n-propyl, CH (CH₃) ₂, n-butyl, 1-methylpropyl, 2-methylpropyl or C (CH₃) ₃, in particular for CH₃, C₂H₅, CH (CH₃) ₂ or C (CH₃) ₃;
• - C₁-C₆ alkyl for: z. B. CH₃, C₂H₅, n-propyl, CH (CH₃) ₂, n-butyl, 1-methylpropyl, 2-methylpropyl, C (CH₃) ₃, n-pentyl, 1-methyl butyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethyl propyl, n-hexyl, 1,1-dimethyl propyl, 1,2-dimethyl propyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-di methylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-di methylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethyl propyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, especially for CH₃, C₂H₅, n-propyl, CH (CH₃) ₂, n-butyl, C (CH₃) ₃, n-pentyl or n-hexyl;
• - C₁-C₄-haloalkyl for: a C₁-C₄-alkyl radical as above called partially or completely by fluorine, chlorine, Bromine and / or iodine is substituted, ie z. B. for CH₂Cl, CH (Cl) ₂, C (Cl) ₃, CH₂F, CHF₂, CF₃, CHFCl, CF (Cl) ₂, CF₂Cl, CF₂Br, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodine ethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2- fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoro ethyl, 1,2-dichloroethyl, 2,2,2-trichloroethyl, C₂F₅, 2-fluorine propyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromo propyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichlor propyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl, especially for CH₂F, CHF₂, CF₃, CH₂Cl or 2-fluoroethyl;
• - C₁-C₆-haloalkyl for: a C₁-C₆-alkyl radical as above called partially or completely by fluorine, chlorine, Bromine and / or iodine is substituted, ie z. B. for CH₂Cl, CH (Cl) ₂, C (Cl) ₃, CH₂F, CHF₂, CF₃, CHFCl, CF (Cl) ₂, CF₂Cl, CF₂Br,  1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodine ethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2- fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoro ethyl, 1,2-dichloroethyl, 2,2,2-trichloroethyl, C₂F₅, 2-fluorine propyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromo propyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichlor propyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2- chloroethyl, 1- (bromomethyl) -2-bromethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, 5,5,5-trichlor pentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl, 6,6,6-trichlorohexyl or dodeca fluorhexyl, especially for CH₂F, CHF₂, CF₃, CH₂Cl, 2-fluorine ethyl, 2-chloroethyl, 1,2-dichloroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl;
• - Cyano-C₁-C₆-alkyl for: z. B. CH₂CN, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyano but-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl, 3-cyanobut-2-yl, 4-cyanobut-2-yl, 1- (CH₂CN) -eth-1-yl, 1- (CH₂CN) -1- (CH₃) -eth- 1-yl, 1- (CH₂CN) prop-1-yl or 2-cyano-hex-6-yl, in particular for CH₂CN or 2-cyanoethyl;
• - C₃-C₇-cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, Cyclohexyl or cycloheptyl, especially for cyclopentyl or cyclohexyl;
• - C₃-C₇-Cycloalkyl-C₁-C₆-alkyl for: cyclopropyl-CH₂, 1-cyclo propyl-ethyl, 2-cyclopropyl-ethyl, 1-cyclopropyl-prop-1-yl, 2-cyclopropyl-prop-1-yl, 3-cyclopropyl-prop-1-yl, 1-cyclo propyl-but-1-yl, 2-cyclopropyl-but-1-yl, 3-cyclopropyl but-1-yl, 4-cyclopropyl-but-1-yl, 1-cyclopropyl-but-2-yl, 2-cyclopropyl-but-2-yl, 3-cyclopropyl-but-2-yl, 4-cyclo propyl-but-2-yl, 1- (cyclopropyl-CH₂) eth-1-yl, 1- (cyclo propyl-CH₂) -1- (CH₃) -eth-1-yl, 1- (cyclopropyl-CH₂) prop-1-yl, Cyclobutyl-CH₂, 1-cyclobutyl-ethyl, 2-cyclobutyl-ethyl, 1-cyclobutyl-prop-1-yl, 2-cyclobutyl-prop-1-yl, 3-cyclobutyl- prop-1-yl, 1-cyclobutyl-but-1-yl, 2-cyclobutyl-but-1-yl, 3-cyclobutyl-but-1-yl, 4-cyclobutyl-but-1-yl, 1-cyclobutyl- but-2-yl, 2-cyclobutyl-but-2-yl, 3-cyclobutyl-but-2-yl, 4-cyclobutyl-but-2-yl, 1- (cyclobutyl-CH₂) eth-1-yl, 1- (cyclo butyl-CH₂) -1- (CH₃) -eth-1-yl, 1- (cyclobutyl-CH₂) prop-1-yl, Cyclopentyl-CH₂, 1-cyclopentyl-ethyl, 2-cyclopentyl-ethyl, 1-cyclopentyl-prop-1-yl, 2-cyclopentyl-prop-1-yl, 3-cyclopen  tyl-prop-1-yl, 1-cyclopentyl-but-1-yl, 2-cyclopentyl but-1-yl, 3-cyclopentyl-but-1-yl, 4-cyclopentyl-but-1-yl, 1-cyclopentyl-but-2-yl, 2-cyclopentyl-but-2-yl, 3-cyclo pentyl-but-2-yl, 4-cyclopentyl-but-2-yl, 1- (cyclopentyl- CH₂) eth-1-yl, 1- (cyclopentyl-CH₂) -1- (CH₃) -eth-1-yl, 1- (cyclo pentyl-CH₂) prop-1-yl, cyclohexyl-CH₂, 1-cyclohexyl-ethyl, 2-cyclohexyl-ethyl, 1-cyclohexyl-prop-1-yl, 2-cyclohexyl- prop-1-yl, 3-cyclohexyl-prop-1-yl, 1-cyclohexyl-but-1-yl, 2-cyclohexyl-but-1-yl, 3-cyclohexyl-but-1-yl, 4-cyclohexyl but-1-yl, 1-cyclohexyl-but-2-yl, 2-cyclohexyl-but-2-yl, 3-cyclohexyl-but-2-yl, 4-cyclohexyl-but-2-yl, 1- (cyclo hexyl-CH₂) eth-1-yl, 1- (cyclohexyl-CH₂) -1- (CH₃) -eth-1-yl, 1- (cyclohexyl-CH₂) prop-1-yl, cycloheptyl-CH₂, 1-cycloheptyl- ethyl, 2-cycloheptyl-ethyl, 1-cycloheptyl-prop-1-yl, 2-cyclo heptyl-prop-1-yl, 3-cycloheptyl-prop-1-yl, 1-cycloheptyl but-1-yl, 2-cycloheptyl-but-1-yl, 3-cycloheptyl-but-1-yl, 4-cycloheptyl-but-1-yl, 1-cycloheptyl-but-2-yl, 2-cyclo heptyl-but-2-yl, 3-cycloheptyl-but-2-yl, 4-cycloheptyl but-2-yl, 1- (cycloheptyl-CH₂) eth-1-yl, 1- (cycloheptyl- CH₂) -1- (CH₃) -eth-1-yl or 1- (cycloheptyl-CH₂) prop-1-yl, especially for C₃-C₆-cycloalkyl-CH₂;
• - (C₁-C₆-alkyl) carbonyl for: z. B. CO-CH₃, CO-C₂H₅, CO-CH₂-C₂H₅, CO-CH (CH₃) ₂, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, CO-C (CH₃) ₃, n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutyl carbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropyl carbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentyl carbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethyl propylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1- methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl, especially for CO-CH₃ or CO-C₂H₅;
• - C₁-C₆ alkoxy for: z. B. OCH₃, OC₂H₅, n-propoxy, OCH (CH₃) ₂, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, OC (CH₃) ₃, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethyl propoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methyl pentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethyl butoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2 dimethyl butoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethyl butoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-tri  methylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methyl propoxy, especially OCH₃, OC₂H₅, OCH (CH₃) ₂ or OC (CH₃) ₃;
• - C₁-C₆-alkoxy-C₁-C₆-alkyl for: by C₁-C₆-alkoxy as before standing called substituted C₁-C₆ alkyl, so z. B. for CH₂OCH₃, CH₂OC₂H₅, CH₂OCH₂-C₂H₅, CH₂OCH (CH₃) ₂, CH₂OCH₂CH₂-C₂H₅, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, CH₂OC (CH₃) ₃, CH₂O (CH₂) ₃-C₂H₅, CH₂O (CH₂) ₄-C₂H₅, CH (CH₃) OCH₃, CH (CH₃) OC₂H₅, CH₂CH₂OCH₃, CH₂CH₂OC₂H₅, CH₂CH₂OCH₂-C₂H₅, CH₂CH₂OCH (CH₃) ₂, CH₂CH₂OCH₂CH₂-C₂H₅, 2- (1-methylpropoxy) ethyl, 2- (2-methyl propoxy) ethyl, CH₂CH₂OC (CH₃) ₃, CH₂CH₂O (CH₂) ₃-C₂H₅, CH₂CH₂O (CH₂) ₄-C₂H₅, 2- (OCH₃) propyl, 2- (OC₂H₅) propyl, 2- (OCH₂-C₂H₅) propyl, 2- [OCH (CH₃) ₂] propyl, 2- (OCH₂CH₂-C₂H₅) propyl, 2- (1-methylpropoxy) propyl, 2- (2-methylpropoxy) propyl, 2- [OC (CH₃) ₃] propyl, 3- (OCH₃) propyl, 3- (OC₂H₅) propyl, 3- (OCH₂-C₂H₅) propyl, 3- [OCH (CH₃) ₂] propyl, 3- (OCH₂CH₂-C₂H₅) propyl, 3- (1-methylpropoxy) propyl, 3- (2-methylpropoxy) propyl, 3- [OC (CH₃) ₃] propyl, 3- [O (CH₂) ₃-C₂H₅] propyl, 3- [O (CH₂) ₄-C₂H₅] propyl, 2- (OCH₃) butyl, 2- (OC₂H₅) butyl, 2- (OCH₂-C₂H₅) butyl, 2- [OCH (CH₃) ₂] butyl, 2- (OCH₂CH₂-C₂H₅) butyl, 2- (1-methylpropoxy) butyl, 2- (2-methylpropoxy) butyl, 2- [OC (CH₃) ₃] butyl, 3- (OCH₃) butyl, 3- (OC₂H₅) butyl, 3- (OCH₂-C₂H₅) butyl, 3- [OCH (CH₃) ₂] butyl, 3- (OCH₂CH₂-C₂H₅) butyl, 3- (1-methylpropoxy) butyl, 3- (2-methylpropoxy) butyl, 3- [OC (CH₃) ₃] butyl, 4- (OCH₃) butyl, 4- (OC₂H₅) butyl, 4- (OCH₂-C₂H₅) butyl, 4- [OCH (CH₃) ₂] butyl, 4- (OCH₂CH₂-C₂H₅) butyl, 4- (1-methylpropoxy) butyl, 4- (2-methylpropoxy) butyl, 4- [OC (CH₃) ₃] butyl, 4- [O (CH₂) ₃-C₂H₅] butyl, 4- [O (CH₂) ₄-C₂H₅] butyl, 5- (OCH₃) pentyl, 5- (OC₂H₅) pentyl, 5- (OCH₂-C₂H₅) pentyl, 5- [OCH (CH₃) ₂] pentyl, 5- (OCH₂CH₂-C₂H₅) pentyl, 5- (1-methyl propoxy) pentyl, 5- (2-methylpropoxy) pentyl, 5- [OC (CH₃) ₃] pentyl, 5- [O (CH₂) ₃-C₂H₅] pentyl, 5- [O (CH₂) ₄-C₂H₅] pentyl, 6- (OCH₃) hexyl, 6- (OC₂H₅) hexyl, 6- (OCH₂-C₂H₅) hexyl, 6- [OCH (CH₃) ₂] hexyl, 6- (OCH₂CH₂-C₂H₅) hexyl, 6- (1-methylpropoxy) hexyl, 6- (2-methyl propoxy) hexyl, 6- [OC (CH₃) ₃] hexyl, 6- [O (CH₂) ₃-C₂H₅] hexyl or 6- [O (CH₂) ₄-C₂H₅] hexyl, especially for CH₂OCH₃ or CH₂OC₂H₅;
• - C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl for: by OCH₃, OC₂H₅, n-propoxy, OCH (CH₃) ₂, n-butoxy, 1-methylpropoxy, 2-methyl propoxy or OC (CH₃) ₃, preferably OCH₃, substituted C₁-C₄-alkoxy-C₁-C₄-alkyl, e.g. B. for CH₂OCH₂OCH₃, CH₂OCH₂OC₂H₅, CH₂OCH₂OCH (CH₃) ₂ or CH₂OCH₂OC (CH₃) ₃;
• - C₁-C₄-haloalkoxy-C₁-C₄-alkyl for: by C₁-C₄-haloalkoxy such as OCH₂Cl, OCH (Cl) ₂, OC (Cl) ₃, OCH₂F, OCHF₂, OCF₃, OCHFCl, OCF (Cl) ₂, OCF₂Cl, OCF₂Br, 1-fluoroethoxy, 2-fluoroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoro  ethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC₂F₅, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chlorine propoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoro propoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, Heptafluoropropoxy, 1- (CH₂F) -2-fluoroethoxy, 1- (CH₂Cl) -2-chlorine ethoxy, 1- (CH₂Br) -2-bromethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy-substituted C₁-C₄-alkyl, so z. B. for 2- (OCHF₂) ethyl, 2- (OCF₃) ethyl or 2- (OC₂F₅) ethyl;
• - C₃-C₇-cycloalkyloxy-C₁-C₆-alkyl for: by C₃-C₇-cycloalkyloxy such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclo hexyloxy and cycloheptyloxy, preferably cyclopropyloxy, substituted C₁-C₆ alkyl, so z. B. for cyclopropyl-OCH₂, 1-cyclopropyloxy-ethyl, 2-cyclopropyloxy-ethyl, 1-cyclopropyloxy-prop-1-yl, 2-cyclo propyloxy-prop-1-yl, 3-cyclopropyloxy-prop-1-yl, 1-cyclo propyloxy-but-1-yl, 2-cyclopropyloxy-but-1-yl, 3-cyclopropyl oxy-but-1-yl, 4-cyclopropyloxy-but-1-yl, 1-cyclopropyloxy but-2-yl, 2-cyclopropyloxy-but-2-yl, 3-cyclopropyloxy-but- 2-yl, 4-cyclopropyloxy-but-2-yl, 1- (cyclopropyl-OCH₂ -) - eth- 1-yl, 1- (cyclopropyl-OCH₂) -1- (CH₃) -eth-1-yl, 1- (cyclopropyl- OCH₂) -prop-1-yl, 2-cyclopropyloxy-hex-6-yl, cyclobutyl-OCH₂, 1-cyclobutyloxy-ethyl, 2-cyclobutyloxy-ethyl, 1-cyclobutyl oxy-prop-1-yl, 2-cyclobutyloxy-prop-1-yl, 3-cyclobutyloxy prop-1-yl, 1-cyclobutyloxy-but-1-yl, 2-cyclobutyloxy-but- 1-yl, 3-cyclobutyloxy-but-1-yl, 4-cyclobutyloxy-but-1-yl, 1-cyclobutyloxy-but-2-yl, 2-cyclobutyloxy-but-2-yl, 3-cyclo butyloxy-but-2-yl, 4-cyclobutyloxy-but-2-yl, 1- (cyclobutyl- OCH₂) -eth-1-yl, 1- (cyclobutyl-OCH₂) -1- (CH₃) -eth-1-yl, 1- (cyclobutyl-OCH₂) prop-1-yl, 2-cyclobutyloxy-hex-6-yl, Cyclopentyl-OCH₂, 1-cyclopentyloxy-ethyl, 2-cyclopentyloxy- ethyl, 1-cyclopentyloxy-prop-1-yl, 2-cyclopentyloxy-prop- 1-yl, 3-cyclopentyloxy-prop-1-yl, 1-cyclopentyloxy-but-1-yl, 2-cyclopentyloxy-but-1-yl, 3-cyclopentyloxy-but-1-yl, 4-cyclopentyloxy-but-1-yl, 1-cyclopentyloxy-but-2-yl, 2-cyclopentyloxy-but-2-yl, 3-cyclopentyloxy-but-2-yl, 4-cyclo pentyloxy-but-2-yl, 1- (cyclopentyl-OCH₂) -eth-1-yl, 1- (cyclo pentyl-OCH₂) -1- (CH₃) -eth-1-yl, 1- (cyclopentyl-OCH₂) prop-1-yl, 2-cyclopentyloxy-hex-6-yl, cyclohexyl-OCH₂, 1-cyclohexyloxy- ethyl, 2-cyclohexyloxy-ethyl, 1-cyclohexyloxy-prop-1-yl, 2-cyclohexyloxy-prop-1-yl, 3-cyclohexyloxy-prop-1-yl, 1-cyclohexyloxy-but-1-yl, 2-cyclohexyloxy-but-1-yl, 3-cyclo hexyloxy-but-1-yl, 4 cyclohexyloxy-but-1-yl, 1-cyclohexyloxy but-2-yl, 2-cyclohexyloxy-but-2-yl, 3-cyclohexyloxy-but-2-yl,  4-cyclohexyloxy-but-2-yl, 1- (cyclohexyl-OCH₂) -eth-1-yl, 1- (cyclohexyl-OCH₂) -1- (CH₃) -eth-1-yl, 1- (cyclohexyl-OCH₂) - prop-1-yl, 2-cyclohexyloxy-hex-6-yl, cycloheptyl-OCH₂, 1-cycloheptyloxy-ethyl, 2-cycloheptyloxy-ethyl, 1-cyclo heptyloxy-prop-1-yl, 2-cycloheptyloxy-prop-1-yl, 3-cyclo heptyloxy-prop-1-yl, 1-cycloheptyloxy-but-1-yl, 2-cyclo heptyloxy-but-1-yl, 3-cycloheptyloxy-but-1-yl, 4-cyclo heptyloxy-but-1-yl, 1-cycloheptyloxy-but-2-yl, 2-cyclo heptyloxy-but-2-yl, 3-cycloheptyloxy-but-2-yl, 4-cyclo heptyloxy-but-2-yl, 1- (cycloheptyl-OCH₂) -eth-1-yl, 1- (cyclo heptyl-OCH₂) -1- (CH₃) -eth-1-yl, 1- (cycloheptyl-OCH₂) prop-1-yl or 2-cycloheptyloxy-hex-6-yl;
• - (C₁-C₄-alkoxy) carbonyl for: COOCH₃, COOC₂H₅, n-propoxy carbonyl, OCH (CH₃) ₂, n-butoxycarbonyl, 1-methylpropoxy carbonyl, 2-methylpropoxycarbonyl or OC (CH₃) ₃, in particular for COOCH₃, COOC₂H₅ or COOC (CH₃) ₃;
• - (C₁-C₆-alkoxy) carbonyl for: COOCH₃, COOC₂H₅, n-propoxy carbonyl, OCH (CH₃) ₂, n-butoxycarbonyl, 1-methylpropoxy carbonyl, 2-methylpropoxycarbonyl, OC (CH₃) ₃, n-pentoxy carbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethyl propoxycarbonyl, n-hexoxycarbonyl, 1,1-dimethylpropoxy carbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxy carbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-di methylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-di methylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-di methylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxy carbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethyl propoxycarbonyl, 1-C₂H₅-1-CH₃-propoxycarbonyl or 1-C₂H₅-2-CH₃-propoxycarbonyl, especially for COOCH₃, COOC₂H₅ or COOC (CH₃) ₃;
• - (C₁-C₆-alkoxy) carbonyl-C₁-C₆-alkyl for: by (C₁-C₆-alkoxy) carbonyl substituted C₁-C₆-alkyl as mentioned above, so z. B. for CH₂COOCH₃, CH₂COOC₂H₅, CH₂COOCH₂-C₂H₅, CH₂COOCH (CH₃) ₂, CH₂COOCH₂CH₂-C₂H₅, (1-methylpropoxycarbonyl) methyl, (2-methylpropoxycarbonyl) methyl, CH₂COOC (CH₃) ₃, CH₂COO (CH₂) ₃-C₂H₅, CH₂COO (CH₂) ₄-C₂H₅, CH (CH₃) COOCH₃, CH (CH₃) COOC₂H₅, CH₂CH₂COOCH₃, CH₂CH₂COOC₂H₅, CH₂CH₂COOCH₂-C₂H₅, CH₂CH₂COOCH (CH₃) ₂, CH₂CH₂COOCH₂CH₂C₂H₅, 2- (1-methylpropoxy carbonyl) ethyl, 2- (2-methylpropoxycarbonyl) ethyl, CH₂CH₂COOC (CH₃) ₃, CH₂CH₂COO (CH₂) ₃-C₂H₅, CH₂CH₂COO (CH₂) ₄-C₂H₅, 2- (COOCH₃) propyl, 2- (COOC₂H₅) propyl, 2- (COOCH₂-C₂H₅) propyl, 2- [COOCH (CH₃) ₂] propyl, 2- (COOCH₂CH₂-C₂H₅) propyl, 2- (1-methyl  propoxycarbonyl) propyl, 2- (2-methylpropoxycarbonyl) propyl, 2- [COOC (CH₃) ₃] propyl, 3- (COOCH₃) propyl, 3- (COOC₂H₅) propyl, 3- (COOCH₂-C₂H₅) propyl, 3- [COOCH (CH₃) ₂] propyl, 3- (COOCH₂CH₂-C₂H₅) propyl, 3- (1-methylpropoxycarbonyl) propyl, 3- (2-methylpropoxycarbonyl) propyl, 3- [COOC (CH₃) ₃] propyl, 3- [COO (CH₂) ₃-C₂H₅] propyl, 3- [COO (CH₂) ₄-C₂H₅] propyl, 2- (COOCH₃) butyl, 2- (COOC₂H₅) butyl, 2- (COOCH₂-C₂H₅) butyl, 2- [COOCH (CH₃) ₂] butyl, 2- (COOCH₂CH₂-C₂H₅) butyl, 2- (1-methyl propoxycarbonyl) butyl, 2- (2-methylpropoxycarbonyl) butyl, 2- [COOC (CH₃) ₃] butyl, 3- (COOCH₃) butyl, 3- (COOC₂H₅) butyl, 3- (COOCH₂-C₂H₅) butyl, 3- [COOCH (CH₃) ₂] butyl, 3- (COOCH₂CH₂-C₂H₅) butyl, 3- (1-methylpropoxycarbonyl) butyl, 3- (2-methylpropoxycarbonyl) butyl, 3- [COOC (CH₃) ₃] butyl, 4- (COOCH₃) butyl, 4- (COOC₂H₅) butyl, 4- (COOCH₂-C₂H₅) butyl, 4- [COOCH (CH₃) ₂] butyl, 4- (COOCH₂CH₂-C₂H₅) butyl, 4- (1-methyl propoxycarbonyl) butyl, 4- (2-methylpropoxycarbonyl) butyl, 4- [COOC (CH₃) ₃] butyl, 4- [COO (CH₂) ₃-C₂H₅] butyl, 4- [COO (CH₂) ₄-C₂H₅] butyl, 5- (COOCH₃) pentyl, 5- (COOC₂H₅) pentyl, 5- (COOCH₂-C₂H₅) pentyl, 5- [COOCH (CH₃) ₂] pentyl, 5- (COOCH₂CH₂-C₂H₅) pentyl, 5- (1-methylpropoxycarbonyl) pentyl, 5- (2-methylpropoxycarbonyl) pentyl, 5- [COOC (CH₃) ₃] pentyl, 5- [COO (CH₂) ₃-C₂H₅] pentyl, 5- [COO (CH₂) ₄-C₂H₅] pentyl, 6- (COOCH₃) hexyl, 6- (COOC₂H₅) hexyl, 6- (COOCH₂-C₂H₅) hexyl, 6- [COOCH (CH₃) ₂] hexyl, 6- (COOCH₂CH₂-C₂H₅) hexyl, 6- (1-methyl propoxycarbonyl) hexyl, 6- (2-methylpropoxycarbonyl) hexyl, 6- [COOC (CH₃) ₃] hexyl, 6- [COO (CH₂) ₃-C₂H₅] hexyl or 6- [COO (CH₂) ₄-C₂H₅] hexyl, especially for CH₂COOCH₃ or CH₂COOC₂H₅;
• - C₁-C₃-alkoxy- (C₁-C₃-alkoxy) carbonyl-C₁-C₆-alkyl for: by OCH₃, OC₂H₅, OCH₂-C₂H₅ or OCH (CH₃) ₂ substituted (C₁-C₃-alkoxy) carbonyl-C₁-C₆-alkyl such as CH₂COOCH₃, CH₂COOC₂H₅, CH₂COOCH₂-C₂H₅, CH₂COOCH (CH₃) ₂, CH (CH₃) COOCH₃, CH (CH₃) COOC₂H₅, CH₂CH₂COOCH₃, CH₂CH₂COOC₂H₅, CH₂CH₂COOCH₂-C₂H₅, CH₂CH₂COOCH (CH₃) ₂, 2- (COOCH₃) propyl, 2- (COOC₂H₅) propyl, 2- (COOCH₂-C₂H₅) propyl, 2- [COOCH (CH₃) ₂] propyl, 3- (COOCH₃) propyl, 3- (COOC₂H₅) propyl, 3- (COOCH₂-C₂H₅) propyl, 3- [COOCH (CH₃) ₂] propyl, 2- (COOCH₃) butyl, 2- (COOC₂H₅) butyl, 2- (COOCH₂-C₂H₅) butyl, 2- [COOCH (CH₃) ₂] butyl, 3- (COOCH₃) butyl, 3- (COOC₂H₅) butyl, 3- (COOCH₂-C₂H₅) butyl, 3- [COOCH (CH₃) ₂] butyl, 4- (COOCH₃) butyl, 4- (COOC₂H₅) butyl, 4- (COOCH₂C₂H₅) butyl, 4- [COOCH (CH₃) ₂] butyl, 5- (COOCH₃) pentyl, 5- (COOC₂H₅) pentyl, 5- (COOCH₂-C₂H₅) pentyl, 5- [COOCH (CH₃) ₂] pentyl, 6- (COOCH₃) hexyl, 6- (COOC₂H₅) hexyl, 6- (COOCH₂C₂H₅) hexyl or 6- [COOCH (CH₃) ₂] hexyl, preferably CH₂COOCH₃ or CH₂COOC₂H₅, so z. B. for CH₂COOCH₂OCH₃, CH₂COOCH₂OC₂H₅, CH₂COOCH₂OCH (CH₃) ₂ or CH₂COOCH₂OC (CH₃) ₃;  
• - (C₁-C₆-alkoxy) carbonyl-C₁-C₆-alkoxy for: by (C₁-C₆-alkoxy) carbonyl substituted C₁-C₆ alkoxy as mentioned above, so z. B. for OCH₂COOCH₃, OCH₂COOC₂H₅, OCH₂COOCH₂-C₂H₅, OCH₂COOCH (CH₃) ₂, OCH₂COOCH₂CH₂-C₂H₅, (1-methylpropoxycarbonyl) methoxy, (2-methylpropoxycarbonyl) methoxy, OCH₂COOC (CH₃) ₃, OCH₂COO (CH₂) ₃-C₂H₅, OCH₂COO (CH₂) ₄-C₂H₅, OCH (CH₃) COOCH₃, OCH (CH₃) COOC₂H₅, OCH₂CH₂COOCH₃, OCH₂CH₂COOC₂H₅, OCH₂CH₂COOCH₂-C₂H₅, OCH₂CH₂COOCH (CH₃) ₂, OCH₂CH₂COOCH₂CH₂-C₂H₅, 2- (1-methylpropoxycarbonyl) ethoxy, 2- (2-methylpropoxy carbonyl) ethoxy, OCH₂CH₂COOC (CH₃) ₃, OCH₂CH₂COO (CH₂) ₃-C₂H₅, OCH₂CH₂COO (CH₂) ₄-C₂H₅, 2- (COOCH₃) propoxy, 2- (COOC₂H₅) propoxy, 2- (COOCH₂-C₂H₅) propoxy, 2- [COOCH (CH₃) ₂] propoxy, 2- (COOCH₂CH₂-C₂H₅) propoxy, 2- (1-methylpropoxycarbonyl) propoxy, 2- (2-methylpropoxycarbonyl) propoxy, 2- [COOC (CH₃) ₃] propoxy, 3- (COOCH₃) propoxy, 3- (COOC₂H₅) propoxy, 3- (COOCH₂-C₂H₅) propoxy, 3- [COOCH (CH₃) ₂] propoxy, 3- (COOCH₂CH₂-C₂H₅) propoxy, 3- (1-methylpropoxycarbonyl) propoxy, 3- (2-methylpropoxy carbonyl) propoxy, 3- [COOC (CH₃) ₃] propoxy, 3- [COO (CH₂) ₃-C₂H₅] propoxy, 3- [COO (CH₂) ₄-C₂H₅] propoxy, 2- (COOCH₃) butoxy, 2- (COOC₂H₅) butoxy, 2- (COOCH₂-C₂H₅) butoxy, 2- [COOCH (CH₃) ₂] butoxy, 2- (COOCH₂CH₂-C₂H₅) butoxy, 2- (1-methyl propoxycarbonyl) butoxy, 2- (2-methylpropoxycarbonyl) butoxy, 2- [COOC (CH₃) ₃] butoxy, 3- (COOCH₃) butoxy, 3- (COOC₂H₅) butoxy, 3- (COOCH₂-C₂H₅) butoxy, 3- [COOCH (CH₃) ₂] butoxy, 3- (COOCH₂CH₂-C₂H₅) butoxy, 3- (1-methylpropoxycarbonyl) butoxy, 3- (2-methylpropoxycarbonyl) butoxy, 3- [COOC (CH₃) ₃] butoxy, 4- (COOCH₃) butoxy, 4- (COOC₂H₅) butoxy, 4- (COOCH₂-C₂H₅) butoxy, 4- [COOCH (CH₃) ₂] butoxy, 4- (COOCH₂CH₂-C₂H₅) butoxy, 4- (1-methyl propoxycarbonyl) butoxy, 4- (2-methylpropoxycarbonyl) butoxy, 4- [COOC (CH₃) ₃] butoxy, 4- [COO (CH₂) ₃-C₂H₅] butoxy, 4- [COO (CH₂) ₄-C₂H₅] butoxy, 5- (COOCH₃) pentoxy, 5- (COOC₂H₅) pentoxy, 5- (COOCH₂-C₂H₅) pentoxy, 5- [COOCH (CH₃) ₂] pentoxy, 5- (COOCH₂CH₂-C₂H₅) pentoxy, 5- (1-methylpropoxycarbonyl) pentoxy, 5- (2-methylpropoxycarbonyl) pentoxy, 5- [COOC (CH₃) ₃] pentoxy, 5- [COO (CH₂) ₃-C₂H₅] pentoxy, 5- [COO (CH₂) ₄-C₂H₅] pentoxy, 6- (COOCH₃) hexoxy, 6- (COOC₂H₅) hexoxy, 6- (COOCH₂-C₂H₅) hexoxy, 6- [COOCH (CH₃) ₂] hexoxy, 6- (COOCH₂CH₂-C₂H₅) hexoxy, 6- (1-methyl propoxycarbonyl) hexoxy, 6- (2-methylpropoxycarbonyl) hexoxy, 6- [COOC (CH₃) ₃] hexoxy, 6- [COO (CH₂) ₃-C₂H₅] hexoxy or 6- [COO (CH₂) ₄-C₂H₅] hexoxy, especially for OCH₂COOCH₃ or OCH₂COOC₂H₅;
• - C₁-C₆ alkylthio for: z. B. SCH₃, SC₂H₅, n-propylthio, SCH (CH₃) ₂, n-butylthio, 1-methylpropylthio, 2-methylpropylthio, SC (CH₃) ₃, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methyl butylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,  1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutyl thio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-di methylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethyl propylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methyl propylthio, especially for SCH₃ or SC₂H₅;
• - C₁-C₆-alkylthio-C₁-C₆-alkyl for: by C₁-C₆-alkylthio as Substituted C₁-C₆ alkyl mentioned above, ie z. B. for CH₂SCH₃, CH₂SC₂H₅, CH₂SCH₂-C₂H₅, CH₂SCH (CH₃) ₂, CH₂SCH₂CH₂-C₂H₅, (1-methylpropylthio) methyl, (2-methylpropylthio) methyl, CH₂SC (CH₃) ₃, CH₂S (CH₂) ₃-C₂H₅, CH₂S (CH₂) ₄-C₂H₅, CH (CH₃) SCH₃, CH (CH₃) SC₂H₅, CH₂CH₂SCH₃, CH₂CH₂SC₂H₅, CH₂CH₂SCH₂-C₂H₅, CH₂CH₂SCH (CH₃) ₂, CH₂CH₂SCH₂CH₂-C₂H₅, 2- (1-methylpropyl thio) ethyl, 2- (2-methylpropylthio) ethyl, CH₂CH₂SC (CH₃) ₃, CH₂CH₂S (CH₂) ₃-C₂H₅, CH₂CH₂S (CH₂) ₄-C₂H₅, 2- (SCH₃) propyl, 2- (SC₂H₅) propyl, 2- (SCH₂-C₂H₅) propyl, 2- [SCH (CH₃) ₂] propyl, 2- (SCH₂CH₂-C₂H₅) propyl, 2- (1-methylpropylthio) propyl, 2- (2-methylpropylthio) propyl, 2- [SC (CH₃) ₃] propyl, 3- (SCH₃) propyl, 3- (SC₂H₅) propyl, 3- (SCH₂-C₂H₅) propyl, 3- [SCH (CH₃) ₂] propyl, 3- (SCH₂CH₂-C₂H₅) propyl, 3- (1-methyl propylthio) propyl, 3- (2-methylpropylthio) propyl, 3- [SC (CH₃) ₃] propyl, 3- [S (CH₂) ₃-C₂H₅] propyl, 3- [S (CH₂) ₄-C₂H₅] propyl, 2- (SCH₃) butyl, 2- (SC₂H₅) butyl, 2- (SCH₂-C₂H₅) butyl, 2- [SCH (CH₃) ₂] butyl, 2- (SCH₂CH₂-C₂H₅) butyl, 2- (1-methylpropylthio) butyl, 2- (2-methylpropylthio) butyl, 2- [SC (CH₃) ₃] butyl, 3- (SCH₃) butyl, 3- (SC₂H₅) butyl, 3- (SCH₂-C₂H₅) butyl, 3- [SCH (CH₃) ₂] butyl, 3- (SCH₂CH₂-C₂H₅) butyl, 3- (1-methylpropylthio) butyl, 3- (2-methylpropylthio) butyl, 3- [SC (CH₃) ₃] butyl, 4- (SCH₃) butyl, 4- (SC₂H₅) butyl, 4- (SCH₂-C₂H₅) butyl, 4- [SCH (CH₃) ₂] butyl, 4- (SCH₂CH₂-C₂H₅) butyl, 4- (1-methylpropylthio) butyl, 4- (2-methylpropylthio) butyl, 4- [SC (CH₃) ₃] butyl, 4- [S (CH₂) ₃-C₂H₅] butyl, 4- [S (CH₂) ₄-C₂H₅] butyl, 5- (SCH₃) pentyl, 5- (SC₂H₅) pentyl, 5- (SCH₂-C₂H₅) pentyl, 5- [SCH (CH₃) ₂] pentyl, 5- (SCH₂CH₂-C₂H₅) pentyl, 5- (1-methylpropylthio) pentyl, 5- (2-methylpropylthio) pentyl, 5- [SC (CH₃) ₃] pentyl, 5- [S (CH₂) ₃-C₂H₅] pentyl, 5- [S (CH₂) ₄-C₂H₅] pentyl, 6- (SCH₃) hexyl, 6- (SC₂H₅) hexyl, 6- (SCH₂-C₂H₅) hexyl, 6- [SCH (CH₃) ₂] hexyl, 6- (SCH₂CH₂-C₂H₅) hexyl, 6- (1-methylpropylthio) hexyl, 6- (2-methylpropylthio) hexyl, 6- [SC (CH₃) ₃] hexyl, 6- [S (CH₂) ₃-C₂H₅] hexyl or 6- [S (CH₂) ₄-C₂H₅] hexyl, in particular for CH₂SCH₃ or CH₂SC₂H₅;  
• - C₃-C₇-Cycloalkylthio-C₁-C₆-alkyl for: by C₃-C₇-cycloalkyl thio such as cyclopropylthio, cyclobutylthio, cyclopentylthio, Cyclohexylthio and Cycloheptylthio, preferably Cyclo propylthio, substituted C₁-C₆ alkyl, so z. B. for cyclopropyl-SCH₂, 1-cyclopropylthio-ethyl, 2-cyclopropylthio-ethyl, 1-cyclopropylthio-prop-1-yl, 2-cyclopropylthio-prop-1-yl, 3-cyclopropylthio-prop-1-yl, 1-cyclopropylthio-but-1-yl, 2-cyclopropylthio-but-1-yl, 3-cyclopropylthio-but-1-yl, 4-cyclopropylthio-but-1-yl, 1-cyclopropylthio-but-2-yl, 2-cyclopropylthio-but-2-yl, 3-cyclopropylthio-but-2-yl 4-cyclopropylthio-but-2-yl, 1- (cyclopropyl-SCH₂ -) - eth-1-yl, 1- (cyclopropyl-SCH₂) -1- (CH₃) - eth-1-yl, 1- (cyclopropyl-SCH₂) -prop-1-yl, 2-cyclopropylthio- hex-6-yl, cyclobutyl-SCH₂, 1-cyclobutylthio-ethyl, 2-cyclo butylthio-ethyl, 1-cyclobutylthio-prop-1-yl, 2-cyclobutyl thio-prop-1-yl, 3-cyclobutylthio-prop-1-yl, 1-cyclobutylthio but-1-yl, 2-cyclobutylthio-but-1-yl, 3-cyclobutylthio-but- 1-yl, 4-cyclobutylthio-but-1-yl, 1-cyclobutylthio-but-2-yl, 2-cyclobutylthio-but-2-yl, 3-cyclobutylthio-but-2-yl, 4-cyclobutylthio-but-2-yl, 1- (cyclobutyl-SCH₂) -eth-1-yl, 1- (cyclobutyl-SCH₂) -1- (CH₃) -eth-1-yl, 1- (cyclobutyl-SCH₂) - prop-1-yl, 2-cyclobutylthio-hex-6-yl, cyclopentyl-SCH₂, 1-cyclopentylthio-ethyl, 2-cyclopentylthio-ethyl, 1-cyclo pentylthio-prop-1-yl, 2-cyclopentylthio-prop-1-yl, 3-cyclo pentylthio-prop-1-yl, 1-cyclopentylthio-but-1-yl, 2-cyclo pentylthio-but-1-yl, 3-cyclopentylthio-but-1-yl, 4-cyclo pentylthio-but-1-yl, 1-cyclopentylthio-but-2-yl, 2-cyclo pentylthio-but-2-yl, 3-cyclopentylthio-but-2-yl, 4-cyclo pentylthio-but-2-yl, 1- (cyclopentyl-SCH₂) -eth-1-yl, 1- (cyclo pentyl-SCH₂) -1- (CH₃) -eth-1-yl, 1- (cyclopentyl-SCH₂) -prop-1-yl, 2-cyclopentylthio-hex-6-yl, cyclohexyl-SCH₂, 1-cyclohexyl thio-ethyl, 2-cyclohexylthio-ethyl, 1-cyclohexylthio-prop- 1-yl, 2-cyclohexylthio-prop-1-yl, 3-cyclohexylthio-prop-1-yl, 1-cyclohexylthio-but-1-yl, 2-cyclohexylthio-but-1-yl, 3-cyclohexylthio-but-1-yl, 4-cyclohexylthio-but-1-yl, 1-cyclohexylthio-but-2-yl, 2-cyclohexylthio-but-2-yl, 3-cyclohexylthio-but-2-yl, 4-cyclohexylthio-but-2-yl, 1- (cyclohexyl-SCH₂) -eth-1-yl, 1- (cyclohexyl-SCH₂) -1- (CH₃) - eth-1-yl, 1- (cyclohexyl-SCH₂) prop-1-yl, 2-cyclohexylthio- hex-6-yl, cycloheptyl-SCH₂, 1-cycloheptylthio-ethyl, 2-cyclo heptylthio-ethyl, 1-cycloheptylthio-prop-1-yl, 2-cycloheptyl thio-prop-1-yl, 3-cycloheptylthio-prop-1-yl, 1-cycloheptyl thio-but-1-yl, 2-cycloheptylthio-but-1-yl, 3-cycloheptylthio- but-1-yl, 4-cycloheptylthio-but-1-yl, 1-cycloheptylthio-but- 2-yl, 2-cycloheptylthio-but-2-yl, 3-cycloheptylthio-but-2-yl, 4-cycloheptylthio-but-2-yl, 1- (cycloheptyl-SCH₂) -eth-1-yl,  1- (cycloheptyl-SCH₂) -1- (CH₃) -eth-1-yl, 1- (cycloheptyl-SCH₂) - prop-1-yl or 2-cycloheptylthio-hex-6-yl;
• - C₁-C₆ alkyl sulfinyl for: z. B. SOCH₃, SOC₂H₅, n-propylsulfinyl, SOCH (CH₃) ₂, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methyl propylsulfinyl, SOC (CH₃) ₃, n-pentylsulfinyl, 1-methylbutyl sulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexyl sulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropyl sulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethyl butylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutyl sulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutyl sulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl, especially for SOCH₃ or SOC₂H₅;
• - C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl for: by C₁-C₆-alkylsulfinyl as mentioned above substituted C₁-C₆ alkyl, so z. B. for CH₂SO-CH₃, CH₂SO-C₂H₅, CH₂SO-CH₂-C₂H₅, CH₂SO-CH (CH₃) ₂, CH₂SO-CH₂CH₂-C₂H₅, (1-methylpropylsulfinyl) methyl, (2-methyl propylsulfinyl) methyl, CH₂SO-C (CH₃) ₃, CH₂SO- (CH₂) ₃-C₂H₅, CH₂SO- (CH₂) ₄-C₂H₅, CH (CH₃) SO-CH₃, CH (CH₃) SO-C₂H₅, CH₂CH₂SO-CH₃, CH₂CH₂SO-C₂H₅, CH₂CH₂SO-CH₂-C₂H₅, CH₂CH₂SO-CH (CH₃) ₂, CH₂CH₂SO-CH₂CH₂-C₂H₅, 2- (1-methylpropylsulfinyl) ethyl, 2- (2-methylpropylsulfinyl) ethyl, CH₂CH₂SO-C (CH₃) ₃, CH₂CH₂SO- (CH₂) ₃-C₂H₅, CH₂CH₂SO- (CH₂) ₄-C₂H₅, 2- (SO-CH₃) propyl, 2- (SO-C₂H₅) propyl, 2- (SO-CH₂-C₂H₅) propyl, 2- [SO-CH (CH₃) ₂] propyl, 2- (SO-CH₂CH₂-C₂H₅) propyl, 2- (1-methyl propylsulfinyl) propyl, 2- (2-methylpropylsulfinyl) propyl, 2- [SO-C (CH₃) ₃] propyl, 3- (SO-CH₃) propyl, 3- (SO-C₂H₅) propyl, 3- (SO-CH₂-C₂H₅) propyl, 3- [SO-CH (CH₃) ₂] propyl, 3- (SO-CH₂CH₂-C₂H₅) propyl, 3- (1-methylpropylsulfinyl) propyl, 3- (2-methylpropylsulfinyl) propyl, 3- [SO-C (CH₃) ₃] propyl, 3- [SO- (CH₂) ₃-C₂H₅] propyl, 3- [SO- (CH₂) ₄-C₂H₅] propyl, 2- (SO-CH₃) butyl, 2- (SO-C₂H₅) butyl, 2- (SO-CH₂-C₂H₅) butyl, 2- [SO-CH (CH₃) ₂] butyl, 2- (SO-CH₂CH₂-C₂H₅) butyl, 2- (1-methyl propylsulfinyl) butyl, 2- (2-methylpropylsulfinyl) butyl, 2- [SO-C (CH₃) ₃] butyl, 3- (SO-CH₃) butyl, 3- (SO-C₂H₅) butyl, 3- (SO-CH₂C₂H₅) butyl, 3- [SO-CH (CH₃) ₂] butyl, 3- (SO-CH₂CH₂-C₂H₅) butyl, 3- (1-methylpropylsulfinyl) butyl, 3- (2-methylpropylsulfinyl) butyl, 3- [SO-C (CH₃) ₃] butyl, 4- (SO-CH₃) butyl, 4- (SO-C₂H₅) butyl, 4- (SO-CH₂-C₂H₅) butyl, 4- [SO-CH (CH₃) ₂] butyl, 4- (SO-CH₂CH₂-C₂H₅) butyl, 4- (1-methyl propylsulfinyl) butyl, 4- (2-methylpropylsulfinyl) butyl,  4- [SO-C (CH₃) ₃] butyl, 4- [SO- (CH₂) ₃-C₂H₅] butyl, 4- [SO- (CH₂) ₄-C₂H₅] butyl, 5- (SO-CH₃) pentyl, 5- (SO-C₂H₅) pentyl, 5- (SO-CH₂-C₂H₅) pentyl, 5- [SO-CH (CH₃) ₂] pentyl, 5- (SO-CH₂CH₂-C₂H₅) pentyl, 5- (1-methylpropylsulfinyl) pentyl, 5- (2-methylpropylsulfinyl) pentyl, 5- [SO-C (CH₃) ₃] pentyl, 5- [SO- (CH₂) ₃-C₂H₅] pentyl, 5- [SO- (CH₂) ₄-C₂H₅] pentyl, 6- (SO-CH₃) hexyl, 6- (SO-C₂H₅) hexyl, 6- (SO-CH₂-C₂H₅) hexyl, 6- [SO-CH (CH₃) ₂] hexyl, 6- (SO-CH₂CH₂-C₂H₅) hexyl, 6- (1-methyl propylsulfinyl) hexyl, 6- (2-methylpropylsulfinyl) hexyl, 6- [SO-C (CH₃) ₃] hexyl, 6- [SO- (CH₂) ₃-C₂H₅] hexyl or 6- [SO- (CH₂) ₄-C₂H₅] hexyl, especially for CH₂SO-CH₃ or CH₂SO-C₂H₅;
• - C₁-C₆ alkylsulfonyl for: z. B. SO₂CH₃, SO₂C₂H₅, n-propyl sulfonyl, SO₂CH (CH₃) ₂, n-butylsulfonyl, 1-methylpropyl sulfonyl, 2-methylpropylsulfonyl, SO₂C (CH₃) ₃, n-pentyl sulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethyl propylsulfonyl, n-hexylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 1-methylpentylsulfonyl, 2-methyl pentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentyl sulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutyl sulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutyl sulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutyl sulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropyl sulfonyl, especially for SO₂CH₃ or SO₂C₂H₅;
• - C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl for: by C₁-C₆-alkylsulfonyl as mentioned above substituted C₁-C₆ alkyl, so z. B. for CH₂SO₂-CH₃, CH₂SO₂-C₂H₅, CH₂SO₂-CH₂-C₂H₅, CH₂SO₂-CH (CH₃) ₂, CH₂SO₂-CH₂CH₂-C₂H₅, (1-methylpropylsulfonyl) methyl, (2-methyl propylsulfonyl) methyl, CH₂SO₂-C (CH₃) ₃, CH₂SO₂- (CH₂) ₃-C₂H₅, CH₂SO₂- (CH₂) ₄-C₂H₅, CH (CH₃) SO₂-CH₃, CH (CH₃) SO₂-C₂H₅, CH₂CH₂SO₂-CH₃, CH₂CH₂SO₂-C₂H₅, CH₂CH₂SO₂-CH₂-C₂H₅, CH₂CH₂SO₂-CH (CH₃) ₂, CH₂CH₂SO₂-CH₂CH₂-C₂H₅, 2- (1-methylpropyl sulfonyl) ethyl, 2- (2-methylpropylsulfonyl) ethyl, CH₂CH₂SO₂-C (CH₃) ₃, CH₂CH₂SO₂- (CH₂) ₃-C₂H₅, CH₂CH₂SO₂- (CH₂) ₄-C₂H₅, 2- (SO₂-CH₃) propyl, 2- (SO₂-C₂H₅) propyl, 2- (SO₂-CH₂-C₂H₅) propyl, 2- [SO₂-CH (CH₃) ₂] propyl, 2- (SO₂-CH₂CH₂-C₂H₅) propyl, 2- (1-methyl propylsulfonyl) propyl, 2- (2-methylpropylsulfonyl) propyl, 2- [SO₂-C (CH₃) ₃] propyl, 3- (SO₂-CH₃) propyl, 3- (SO₂-C₂H₅) propyl, 3- (SO₂-CH₂-C₂H₅) propyl, 3- [SO₂-CH (CH₃) ₂] propyl, 3- (SO₂-CH₂CH₂-C₂H₅) propyl, 3- (1-methylpropylsulfonyl) propyl, 3- (2-methylpropylsulfonyl) propyl, 3- [SO₂-C (CH₃) ₃] propyl, 3- [SO₂- (CH₂) ₃-C₂H₅] propyl, 3- [SO₂- (CH₂) ₄-C₂H₅] propyl,  2- (SO₂-CH₃) butyl, 2- (SO₂-C₂H₅) butyl, 2- (SO₂-CH₂-C₂H₅) butyl, 2- [SO₂-CH (CH₃) ₂] butyl, 2- (SO₂-CH₂CH₂-C₂H₅) butyl, 2- (1-methyl propylsulfonyl) butyl, 2- (2-methylpropylsulfonyl) butyl, 2- [SO₂-C (CH₃) ₃] butyl, 3- (SO₂-CH₃) butyl, 3- (SO₂-C₂H₅) butyl, 3- (SO₂-CH₂-C₂H₅) butyl, 3- [SO₂-CH (CH₃) ₂] butyl, 3- (SO₂-CH₂CH₂-C₂H₅) butyl, 3- (1-methylpropylsulfonyl) butyl, 3- (2-methylpropylsulfonyl) butyl, 3- [SO₂-C (CH₃) ₃] butyl, 4- (SO₂-CH₃) butyl, 4- (SO₂-C₂H₅) butyl, 4- (SO₂-CH₂-C₂H₅) butyl, 4- [SO₂-CH (CH₃) ₂] butyl, 4- (SO₂-CH₂CH₂-C₂H₅) butyl, 4- (1-methyl propylsulfonyl) butyl, 4- (2-methylpropylsulfonyl) butyl, 4- [SO₂-C (CH₃) ₃] butyl, 4- [SO₂- (CH₂) ₃-C₂H₅] butyl, 4- [SO₂- (CH₂) ₄-C₂H₅] butyl, 5- (SO₂-CH₃) pentyl, 5- (SO₂-C₂H₅) pentyl, 5- (SO₂-CH₂-C₂H₅) pentyl, 5- [SO₂-CH (CH₃) ₂] pentyl, 5- (SO₂-CH₂CH₂-C₂H₅) pentyl, 5- (1-methyl propylsulfonyl) pentyl, 5- (2-methylpropylsulfonyl) pentyl, 5- [SO₂-C (CH₃) ₃] pentyl, 5- [SO₂- (CH₂) ₃-C₂H₅] pentyl, 5- [SO₂- (CH₂) ₄-C₂H₅] pentyl, 6- (SO₂-CH₃) hexyl, 6- (SO₂-C₂H₅) hexyl, 6- (SO₂-CH₂-C₂H₅) hexyl, 6- [SO₂-CH (CH₃) ₂] hexyl, 6- (SO₂-CH₂CH₂-C₂H₅) hexyl, 6- (1-methylpropylsulfonyl) hexyl, 6- (2-methylpropylsulfonyl) hexyl, 6- [SO₂-C (CH₃) ₃] hexyl, 6- [SO₂- (CH₂) ₃-C₂H₅] hexyl or 6- [SO₂- (CH₂) ₄-C₂H₅] hexyl, in particular for CH₂SO₂-CH₃ or CH₂SO₂-C₂H₅;
• - C₁-C₆-alkylaminosulfonyl for: z. B. H₃C-NHSO₂-, H₅C₂-NHSO₂-, n-propyl-NHSO₂-, (CH₃) ₂CH-NHSO₂-, n-butyl-NHSO₂-, 1-methyl propyl-NHSO₂-, 2-methylpropyl-NHSO₂-, (CH₃) ₃C-NHSO₂-, n-pentyl-NHSO₂-, 1-methylbutyl-NHSO₂-, 2-methylbutyl-NHSO₂-, 3-methylbutyl-NHSO₂-, 2,2-dimethylpropyl-NHSO₂-, 1-ethyl propyl-NHSO₂-, n-hexyl-NHSO₂-, 1,1-dimethylpropyl-NHSO₂-, 1,2-dimethylpropyl-NHSO₂-, 1-methylpentyl-NHSO₂-, 2-methyl pentyl-NHSO₂-, 3-methylpentyl-NHSO₂-, 4-methylpentyl-NHSO₂-, 1,1-dimethylbutyl-NHSO₂-, 1,2-dimethylbutyl-NHSO₂-, 1,3-di methylbutyl-NHSO₂-, 2,2-dimethylbutyl-NHSO₂-, 2,3-dimethyl butyl-NHSO₂-, 3,3-dimethylbutyl-NHSO₂, 1-ethylbutyl-NHSO₂-, 2-ethylbutyl-NHSO₂-, 1,1,2-trimethylpropyl-NHSO₂-, 1,2,2-tri methylpropyl-NHSO₂-, 1-ethyl-1-methylpropyl-NHSO₂- or 1-ethyl-2-methylpropyl-NHSO₂-, especially for H₃C-NHSO₂- or H₅C₂-NHSO₂-;
• - Di- (C₁-C₆-alkyl) aminosulfonyl for: z. B. (CH₃) ₂N-SO₂-, (C₂H₅) ₂N-SO₂-, N, N-dipropylamino-SO₂-, N, N-di (1-methyl ethyl) amino-SO₂-, N, N-dibutylamino-SO₂-, N, N-di (1-methyl propyl) amino-SO₂-, N, N-di (2-methylpropyl) amino-SO₂-, N, N-Di (1,1-dimethylethyl) amino-SO₂-, N-ethyl-N-methyl amino-SO₂-, N-methyl-N-propylamino-SO₂-, N-methyl-N- (1- methylethyl) amino-SO₂-, N-butyl-N-methylamino-SO₂-, N-methyl-N- (1-methylpropyl) amino-SO₂-, N-methyl-N- (2-methyl  propyl) amino-SO₂-, N- (1,1-dimethylethyl) -N-methylamino-SO₂-, N-ethyl-N-propylamino-SO₂-, N-ethyl-N- (1-methylethyl) amino- SO₂-, N-butyl-N-ethylamino-SO₂-, N-ethyl-N- (1-methylpropyl) amino-SO₂-, N-ethyl-N- (2-methylpropyl) amino-SO₂-, N-ethyl-N- (1,1-dimethylethyl) amino-SO₂-, N- (1-methylethyl) -N-propyl amino-SO₂-, N-butyl-N-propylamino-SO₂-, N- (1-methylpropyl) -N- propylamino-SO₂-, N- (2-methylpropyl) -N-propylamino-SO₂-, N- (1,1-dimethylethyl) -N-propylamino-SO₂-, N-butyl-N- (1- methylethyl) amino-SO₂-, N- (1-methylethyl) -N- (1-methyl propyl) amino-SO₂-, N- (1-methylethyl) -N- (2-methylpropyl) amino-SO₂-, N- (1,1-dimethylethyl) -N- (1-methylethyl) amino-SO₂-, N-butyl-N- (1-methylpropyl) amino-SO₂-, N-butyl-N- (2-methyl propyl) amino-SO₂-, N-butyl-N- (1,1-dimethylethyl) amino-SO₂-, N- (1-methylpropyl) -N- (2-methylpropyl) amino-SO₂-, N- (1,1-di methylethyl) -N- (1-methylpropyl) amino-SO₂- or N- (1,1-di methylethyl) -N- (2-methylpropyl) amino-SO₂-, especially for (CH₃) ₂N-SO₂- or (C₂H₅) ₂N-SO₂-;
• - C₂-C₆-alkenyl for: vinyl and C₃-C₆-alkenyl such as prop-1-en-1-yl, Allyl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl, n-butene 3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, n-pentene 1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl but-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut- 2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethyl-prop-2-en-1-yl, 1,2-di methyl-prop-1-en-1-yl, 1,2-dimethyl-prop-2-en-1-yl, 1-ethyl prop-1-en-2-yl, 1-ethylprop-2-en-1-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5- en-1-yl, 1-methyl-pent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methyl pent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2- en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methyl pent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4- en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethyl-but-2-en-1-yl, 1,1-dimethyl-but-3-en-1-yl, 1,2-dimethyl-but-1-en-1-yl, 1,2-dimethyl-but-2-en-1-yl, 1,2-dimethyl-but-3-en-1-yl, 1,3-dimethyl-but-1-en-1-yl, 1,3-dimethyl-but-2-en-1-yl, 1,3-dimethyl-but-3-en-1-yl, 2,2-dimethyl-but-3-en-1-yl, 2,3-dimethyl-but-1-en-1-yl, 2,3-dimethyl-but-2-en-1-yl, 2,3-dimethyl-but-3-en-1-yl, 3,3-dimethyl-but-1-en-1-yl, 3,3-dimethyl-but-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3- en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethyl but-3-en-1-yl, 1,1,2-trimethyl-prop-2-en-1-yl, 1-ethyl-1-  methyl-prop-2-en-1-yl, 1-ethyl-2-methyl-prop-1-en-1-yl and 1-ethyl-2-methyl-prop-2-en-1-yl, especially for allyl;
• - C₃-C₈-alkenyl for: C₃-C₆-alkenyl as mentioned above, or e.g. B. for n-hept-2-en-1-yl, n-hept-3-en-1-yl, n-oct-2-en-1-yl, n-oct-3-en-1-yl, especially for allyl;
• - C₃-C₈-haloalkenyl for: C₃-C₈-alkenyl as above ge is called partially or completely by fluorine, chlorine, bromine and / or iodine is substituted, e.g. B. for 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-tri chlorallyl, 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 3-chloroallyl;
• - C₁-C₆-alkoxy-C₃-C₈-alkenyl for: by C₁-C₆-alkoxy such as Substituted C₃-C₈ alkenyl mentioned above, that is z. B. for 3- (methoxy) allyl;
• - C₃-C₆-alkenyloxy for: z. B. Prop-1-en-1-yloxy, alkyloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n-buten-3-yloxy, 1-methylprop-1-en-1-yloxy, 2-methylprop 1-en-1-yloxy, 1-methylprop-2-en-1-yloxy, 2-methylprop-2-en- 1-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yl oxy, n-penten-4-yloxy, 1-methylbut-1-en-1-yloxy, 2-methyl but-1-en-1-yloxy, 3-methylbut-1-en-1-yloxy, 1-methylbut-2- en-1-yloxy, 2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yl oxy, 1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy, 3-methylbut-3-en-1-yloxy, 1,1-dimethyl-prop-2-en-1-yloxy, 1,2-dimethyl-prop-1-en-1-yloxy, 1,2-dimethyl-prop-2-en-1-yl oxy, 1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, n-hex-1-en-1-yloxy, n-hex-2-en-1-yloxy, n-hex-3-en-1-yloxy, n-hex-4-en-1-yloxy, n-hex-5-en-1-yloxy, 1-methylpent-1-en- 1-yloxy, 2-methylpent-1-en-1-yloxy, 3-methylpent-1-en-1-yl oxy, 4-methylpent-1-en-1-yloxy, 1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy, 3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy, 1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy, 3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy, 1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy, 3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy, 1,1-dimethyl-but-2-en-1-yloxy, 1,1-dimethyl-but-3-en-1-yloxy, 1,2-dimethyl-but-1-en-1-yloxy, 1,2-dimethyl-but-2-en-1-yloxy, 1,2-dimethyl-but-3-en-1-yloxy, 1,3-dimethyl-but-1-en-1-yloxy, 1,3-dimethyl-but-2-en-1-yloxy, 1,3-dimethyl-but-3-en-1-yloxy, 2,2-dimethyl-but-3-en-1-yloxy, 2,3-dimethyl-but-1-en-1-yloxy, 2,3-dimethyl-but-2-en-1-yloxy, 2,3-dimethyl-but-3-en-1-yloxy, 3,3-dimethyl-but-1-en-1-yloxy,  3,3-dimethyl-but-2-en-1-yloxy, 1-ethylbut-1-en-1-yloxy, 1-ethylbut-2-en-1-yloxy, 1-ethylbut-3-en-1-yloxy, 2-ethyl but-1-en-1-yloxy, 2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en- 1-yloxy, 1,1,2-trimethyl-prop-2-en-1-yloxy, 1-ethyl-1-methyl prop-2-en-1-yloxy, 1-ethyl-2-methyl-prop-1-en-1-yloxy or 1-ethyl-2-methyl-prop-2-en-1-yloxy, especially for allyl oxy;
• - C₂-C₄-alkenyloxy-C₁-C₄-alkyl for: by C₃-C₄-alkenyloxy such as Vinyloxy, allyloxy, but-1-en-3-yloxy, but-1-en-4-yloxy, But-2-en-1-yloxy, 1-methylprop-2-enyloxy or 2-methyl prop-2-enyloxy substituted C₁-C₄ alkyl, for example for vinyloxymethyl, allyloxymethyl, 2-allyloxyethyl or But-1-en-4-yloxymethyl, especially for 2-allyloxyethyl;
• - C₃-C₆-alkynyl for: z. B. Prop-1-in-1-yl, propargyl, n-but-1- in-1-yl, n-but-1-in-3-yl, n-but-1-in-4-yl, n-but-2-in-1-yl, n-pent-1-in-1-yl, n-pent-1-in-3-yl, n-pent-1-in-4-yl, n-pent 1-in-5-yl, n-pent-2-in-1-yl, n-pent-2-in-4-yl, n-pent-2-in 5-yl, 3-methyl-but-1-yn-3-yl, 3-methyl-but-1-yn-4-yl, n-hex 1-in-1-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-1-yl, 3-methyl-pent-1-in-3-yl, 3-methyl pent-1-in-4-yl, 3-methyl-pent-1-in-5-yl, 4-methyl-pent-1- in-1-yl, 4-methyl-pent-2-in-4-yl or 4-methyl-pent-2-in 5-yl, especially for propargyl;
• - C₃-C₈-haloalkynyl: C₃-C₈-alkynyl as mentioned above, partially or completely by fluorine, chlorine, bromine and / or iodine is substituted, e.g. B. for 1,1-difluoro prop-2-in-1-yl, 4-fluorobut-2-in-1-yl, 4-chlorobut-2-in-1-yl, 1,1-difluorobut-2-in-1-yl, 5-fluoropent-3-in-1-yl or 6-fluorine hex-4-in-1-yl;
• - C₁-C₆-alkoxy-C₃-C₈-alkynyl for: by C₁-C₆-alkoxy as above called substituted C₃-C₈ alkynyl, so z. B. for 3-methoxy prop-2-in-1-yl;
• - C₃-C₈-alkynyloxy for: z. B. propargyloxy, prop-2-in-1-yloxy, n-but-1-in-1-yloxy, n-but-1-in-3-yloxy, n-but-1-in-4-yloxy, n-but-2-in-1-yloxy, n-pent-1-in-1-yloxy, n-pent-1-in-3-yloxy, n-pent-1-in-4-yloxy, n-pent-1-in-5-yloxy, n-pent-2-in-1-yl oxy, n-pent-2-yn-4-yloxy, n-pent-2-yn-5-yloxy, 3-methyl but-1-in-3-yloxy, 3-methyl-but-1-in-4-yloxy, n-hex-1-in-1-yl oxy, n-hex-1-in-3-yloxy, n-hex-1-in-4-yloxy, n-hex-1-in-5-yl oxy, n-hex-1-in-6-yloxy, n-hex-2-in-1-yloxy, n-hex-2-in-4-yl  oxy, n-hex-2-in-5-yloxy, n-hex-2-in-6-yloxy, n-hex-3-in-1-yl oxy, n-hex-3-in-2-yloxy, 3-methylpent-1-in-1-yloxy, 3-methyl pent-1-in-3-yloxy, 3-methylpent-1-in-4-yloxy, 3-methylpent-1- in-5-yloxy, 4-methylpent-1-in-1-yloxy, 4-methylpent-2-in-4-yl or 4-methylpent-2-in-5-yloxy, especially for propargyl oxy;
• - C₃-C₄-alkynyloxy-C₁-C₄-alkyl for: by C₃-C₄-alkynyloxy such as Propargyloxy, but-1-in-3-yloxy, but-1-in-4-yloxy, but-2-in-1- yloxy, 1-methylprop-2-inyloxy and 2-methylprop-2-inyloxy, preferably propargyloxy, substituted C₁-C₄ alkyl, that is for example for propargyloxymethyl or 2-propargyloxy ethyl, especially for 2-propargyloxyethyl.

The benzyl group (as one of the meanings of R⁴) is before preferably unsubstituted or carries a nitro, halogen, C₁-C₄-alkyl-, C₁-Coxy-alkoxy- or (C₁-C₄-alkoxy) carbonyl- Substituents.

With regard to the use of the substituted 2-arylpyridines I as herbicides and / or as desiccant / defoliant compounds, the variables preferably have the following meanings, individually or in combination:
n zero;
R¹-mercapto, hydroxysulfonyl, chlorosulfonyl, aminosulfonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl, especially C₁-C₆-alkylsulfonyl;
R² halogen, especially chlorine;
R³ is hydrogen or halogen, preferably halogen, especially fluorine or chlorine;
R⁴ hydrogen, C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl, (C₁- C₆-alkoxy) carbonyl-C₁-C₆-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl, C₃-C₈-alkenyloxy or C₃-C₈-alkynyloxy, especially hydrogen, C₁-C₆-alkyl, cyano-C₁-C₆ -alkyl, (C₁-C₆-alkoxy) carbonyl-C₁-C₆-alkyl, C₃-C₈-alkenyl or C₃-C₈-alkynyl;
X oxygen;
Y is a chemical bond or C (R⁵) -R⁶, where R⁵ and R⁶ are independently hydrogen, C₁-C₄-alkyl or (C₁-C₄-alkoxy) carbonyl, especially a chemical bond or methylene.

The compounds of the formula Ia are very particularly preferred (I with n = zero; R¹ = methylsulfonyl; R² = chlorine, R³ = fluorine and X = oxygen), in particular the compounds of Table 1:

Furthermore, the substituted 2-arylpyridines are of the formulas Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ik, Im and In especially before trains, especially

• - The compounds Ib.1 to Ib.363, which differ from the corresponding compounds Ia.1 to Ia.363 only in that R³ is chlorine:
• - The compounds Ic.1 to Ic.363, which differ from the corresponding compounds Ia.1 to Ia.363 only in that R³ is hydrogen:
• - The compounds Id.1 to Id.363, which differ from the corresponding compounds Ia.1 to Ia.363 only in that R¹ is ethylsulfonyl:
• - The compounds Ie.1 to Ie.363, which differ from the corresponding compounds Ia.1 to Ia.363 only in that R¹ is ethylsulfonyl and R³ is chlorine:
• - The compounds If.1 to If.363, which differ from the corresponding compounds Ia.1 to Ia.363 only in that R¹ is ethylsulfonyl and R³ is hydrogen:
• - The compounds Ig.1 to Ig.363, which differ from the corresponding compounds Ia.1 to Ia.363 only in that R¹ is methylsulfinyl:
• - The compounds Ih.1 to Ih.363, which differ from the corresponding compounds Ia.1 to Ia.363 only in that R¹ is methylsulfinyl and R³ is chlorine:
• - The compounds Ii.1 to Ii.363, which differ from the corresponding compounds Ia.1 to Ia.363 only in that R¹ is methylsulfinyl and R³ is hydrogen:
• - The compounds Ik.1 to Ik.363, which differ from the corresponding compounds Ia.1 to Ia.363 only in that R¹ is methylthio:
• - The compounds Im.1 to Im.363, which differ from the corresponding compounds Ia.1 to Ia.363 only in that R¹ is methylthio and R³ is chlorine:
• - The compounds In.1 to In.363, which differ from the corresponding compounds Ia.1 to Ia.363 only in that R¹ is methylthio and R³ is hydrogen:

The substituted 2-arylpyridines of the formula I are various available way, for example according to one of the following Method:

Procedure A)

Oxidation of substituted 2-arylpyridines of the formula I, in where n is zero and the substituents R¹ and R⁴ and X and Y contain no oxidizable sulfur, known per se Manner {cf. e.g. B. A. Albini & S. Pietra, Heterocyclic N-Oxides, CRC-Press Inc., Boca Raton, USA 1991; H.S. Mosher et al., Org. Synth. Coll. Vol. IV 1963, page 828; E.C. Taylor et al., Org. Synth. Coll. Vol. IV 1963, page 704; T.W. Bell et. al., Org. Synth. 69, page 226 (1990)}:

Among the oxidations customary for the oxidation of the pyridine ring Examples are peracetic acid, trifluoroperacetic acid, perbenzoic acid, m-chloroperbenzoic acid, monopermalein acid, magnesium monoperphthalate, sodium perborate, Oxone® (contains peroxydisulphate), tungstic acid and hydrogen peroxide referenced.

Suitable solvents are e.g. B. water, sulfuric acid, Carboxylic acids such as acetic acid and trifluoroacetic acid as well halogenated hydrocarbons such as dichloromethane and Chloroform.

The oxidation normally takes place at temperatures of 0 ° C to the boiling point of the reaction mixture.

The oxidizer is usually in at least equimolar amounts, based on the starting compound, used. Generally there is an excess Oxidants proven to be particularly advantageous.  

Procedure B)

Oxidation of substituted 2-arylpyridines of the formula I, in which R¹ is C₁-C₆-alkylthio or C₁-C₆-alkylsulfinyl and the variables R⁴, X and Y contain no oxidizable sulfur, in a manner known per se {cf. e.g. B. C.S. Giam et al., Org. Prep. Proced. Int. 13 (2), p. 137 (1981); S.G. Woods et al., J. Heterocycl. Chem. 21, N1, 97-101 (1984); S.G. Woods, U.S. 4,616,087; N. Finch et al., J. Med. Chem. 21 (12), 1269-1274 (1978); H. Ban-Oganowska, Pd. J. Chem. 67 (9), 1609-1613 (1993); A.D. Dunn & R. Norrie, J. Prakt. Chem./Chem.-Ztg. 335, 269-272 (1993)}:

Regarding suitable solvents, oxidizing agents and reak tion temperatures, reference is made to the information given in process A).

For the production of valuable products I with R¹ = alkylsulfinyl it is recommended not to exceed 1.1 equivalents of the Use oxidizing agent. For the preparation of I with R¹ = Alkylsulfonyl it is necessary to have at least one equivalent or use at least two equivalents of the oxidizing agent, each after whether one of the corresponding compounds I with R¹ = Alkylthio or with R1 = alkylsulfinyl.  

Process C)

Transition metal-catalyzed cross-coupling reaction of 2-halopyridines II (Hal = chlorine or bromine) with metal organic compounds of formula III on known per se Manner {cf. e.g. B. WO 95/02580 and there on pages 21 and 22 cited literature}:

M¹ stands for B (OH) ₂, magnesium chloride, bromide or iodide, Zinc chloride, bromide or iodide, lithium, copper or tin tri (C₁-C₄-alkyl), preferably for B (OH) ₂, magnesium chloride, bromide or iodide, zinc chloride, bromide or iodide.

Alternatively, instead of the boronic acids III {M¹ = B (OH) ₂} the Boroxine IV are used.

Palladium catalysts in particular come as catalysts such as tetrakis (triphenylphosphine) palladium (O), bis (triphenyl phosphine) palladium (II) chloride, 1,4-bis (diphenylphosphino) - butane-palladium (II) chloride, 1,2-bis (diphenylphosphino) ethane palladium (II) chloride, palladium (II) acetate + triphenylphosphine, Palladium (II) acetate + tri- (o-tolyl) phosphine or palladium on activated carbon, and nickel catalysts such as bis (triphenyl phosphine) nickel (II) chloride, 1,3-bis (diphenylphosphino) propane nickel (II) chloride or nickel (II) acetylacetonate.

For the preparation of II, reference is made to the explanations in process G (XXXIVa → XXXIVb → → II).

Starting from V are the substituted 2-arylpyridines of the formula I (X = O) then available according to synthesis scheme (1):

Implementations of this type are known per se, for example from the following literature:

Ether cleavage of phenol alkyl ethers:

• 1. WO 95/02590, page 35, example 1, synthesis step 2;
• 2. A.V. Blokhin et al., Khim. Heterotics Soedin 9, 1226-1229 (1990);
• 3. B. Singh et al., J. Heterocycl. Chem. 28 (4), 933-937 (1991);
• 4. C.A. Howard et al., Angew. Chem. Int. Ed. 31 (8), 1028-1030 (1992);
• 5. T. Katsunori et al., Bull. Chem. Soc. Jpn. 63, 3132-3140 (1990);
• 6. M. Hamana et al., Chem. And. Pharm. Bull. 25 (6), 1256-1264 (1977);

Nitration of phenols:

• 1. WO 95/02590, page 35, example 1, synthesis step 3;
• 2. P. Keller, Bull. Soc. Chim. Fr. 131 (1), 27-29 (1994);

Reduction of nitrophenols:

• 1. WO 95/02590, page 35, example 1, synthesis step 4;
• 2. U.S. 4,959,492;
• 3. K.J. Stutts et al., J. Org. Chem. 54, 3740 (1989);
• 4. P.K. Arora et al., Ind. J. Chem. B 18, 199-200 (1979);

Reaction of aminophenols with phosgene derivatives:

• 1. R.J. Nachman, J. Heterocyclic Chem. 19, 1545 (1982);

Alkylation of benzoxazolones:

• 1. J.J. D'Amico et al., J. Heterocyclic Chem. 25, 1487 (1988);
• 2. W.J. Close et al., J. Am. Chem. Soc. 71, 1265 (1949);
• 3. M. Yamato et al., Chem. And. Pharm. Bull. 31: 1733 (1983);
• 4. U.S. 4,640,707;
• 5. BG 40 729;
• 6. U.S. 4,790,868;
• 7. P. Depreux et al., Heterocycles 36, 1051 (1993);
• 8. G. Pilli et al., Pharmaceutical Research 43, 1351 (1993);
• 9. A. Benarab et al., Tetrahedron Lett. 34, 7567 (1993);

Reaction of aminophenols with α-halocarboxylic acid (derivatives) n:

• 1. X. Huang et al., Synthesis 1984, 851;
• 2. D.R. Shridhar et al., Org. Prep. Proced. Int. 14, 195 (1982);
• 3. U.S. 4,307,091;
• 4. DB 3 901 461;
• 5. D. Kikel et al., J. Heterocyclic Chem. 30, 597 (1993);
• 6. H. Tawada et al., Chem. Pharm. Bull. 38, 1238 (1990);
• 7. Kawakita, T. et al., Chem. Pharm. Bull. 40: 624 (1992);  
• 8. WO 95/02590, page 35, example 1, synthesis steps 5 and 6;

Alkylation of benzoxazinones:

• 1.KU.P. Rao et al., Ind. J. Chem. B 24, 1120 (1985);
• 2. JP-A 61/140 572;
• 3. U.S. 4,640,707;
• 4. JP-A 63/107 970;
• 5. U.S. 4,792,605;
• 6. WO 95/02590, page 35, example 1, synthesis step 6.

The aminophenol VIII can also be combined with oxalic acid (derivatives) XI such as Oxalic acid chloride and (optionally substituted) malein acid anhydride are implemented:

Such implementations are also known per se, for example from the following literature:

• 1. U.S. 4,826,833;
• 2. N. Kawahara et al., Heterocycles 24, 2803 (1986);
• 3. D.R. Shridhar et al., Ind. J. Chem. B 24, 992 (1985);
• 4. C.O. Okafor et al., J. Chem. Soc., Perkin Trans. 1, 1993, 159

Procedure D)

The substituted 2-arylpyridines I, in which X is oxygen, Sulfur, -NH- or -N (CH₃) - means can be according to synthesis Create scheme (3):

The p-fluorophenylpyridines of the formula XII are, for example, ana log process C) by transition metal-catalyzed cross cup planning reaction of II with XVII

producible.

Implementations of this type are known per se, for example from the following literature:

Nitration of fluoroaromatics:

• 1. WO 95/02590, page 39, example 3, synthesis step 2;
• 2. E.A. Bliss et al., J. Chem. Soc. Perkin Trans. 1, 2217, (1987);
• 3. J.S. Amato et al., J. Heterocyclic Chem. 16, 1153 (1979);

Reaction of o-fluoronitrobenzenes with amines:

• 1. WO 95/02590, page 39, example 3, synthesis step 3; page 43, Example 9, Synthesis Step 1; Page 44, example 11;
• 2. T. Wagner-Jauregg et al., Chem. Ber. 89, 253 (1956);
• 3. A.L. Levy et al., J. Am. Chem. Soc. 77: 2899 (1955);
• 4. G. Lang et al., U.S. 4,910,341;

Reaction of o-fluoronitrobenzenes with mercaptans:

• 1. J. Slade et al., J. Med. Chem. 28, 1517 (1985);
• 2. M.E. Leblanc et al., J. Fluor. Chem. 17, 233-248 (1981);

Reaction of o-fluoronitrobenzenes with alcohols:

• 1. M. Enomoto et al., U.S. 4,970,322 & U.S. 4,877,444;
• 2. E. Akimoto et al., JP-A 61/180 746;

Reduction of nitroaromatics with subsequent cyclocondensation:

• 1. G. Theodoridis et al., J. Heterocyclic Chem. 28, 849 (1991);
• 2. N. Kawahara et al., Heterocycles 16, 729 (1981);
• 3. V. Evdokimoff, Gazz. Chim. Italian 90, 1133 (1960);
• 4. R.L. Wear et al., J. Am. Chem. Soc. 72: 2893 (1950);
• 5. U.S. 4,734,124;
• 6. Enomoto et al., U.S. 4,970,322 & U.S. 4,877,444;
• 7. V.N. Lisitsyn et al., Zh. Organ. XIMII 25: 1095 (1990);
• 8. Makosza M. et al., Tetrahedron 51, 7263 (1995).

For the implementation of XIVb with phosgene (derivatives) and alkylation of Compound I with R⁴ = H see the one cited in process C) Literature.  

Procedure E)

The substituted 2-arylpyridines of the formula I in which X Methylene and Y mean a chemical bond, can be according to Create synthesis scheme (4):

From XIII {production s. Synthesis scheme (3)} is obtained by nucleophilic aromatic substitution of fluorine by a Malonic acid tert-butyl ester residue and subsequent acidic Hydrolysis with decarboxylation of the phenylacetic acid derivative XX. With its reduction occurs {as in the case of XVI; see. Synthesis scheme (3)} spontaneous cyclokendensation to I {n = 0; R⁴ = H; X = CH₂; Y = binding}. Such implementations are also pending known, for example from the following literature:

Implementation of fluoronitroaromatics with malonic esters:

• 1. G.J. Quallich et al., Synthesis, 51-53 (1993);
• 2. J.A. Walker, U.S. 4,398,035;
• 3. H. Burghard et al., J. Pharm. Sci. 69: 933 (1980);
• 4. F.J. Goetz et al., J. Org. Chem. 48, 2468 (1983);
• 5. N. Ogawa et al., J. Pharm. Soc. Yep 107, 111 (1987);

Hydrolysis and decarboxylation of phenylmalonic esters:

• 1. J.G. Atkinson et al., Tetrahedron Lett., 2857 (1979);
• 2. M.M. Elshafie Sayed, Chimia 36, 343 (1982);
• 3. M.A.E. Bowman et al., Org. Prep. Proced. Int. 1990, 22: 636;
• 4. D. Barrett et al., J. Org. Chem. 60, 3928 (1995);

Reduction of the nitro group and cyclocondensation:

• 1. G. Gallagher Jr. et al., J. Med. Chem. 28, 1533 (1985);
• 2. A.L. Davis et al., J. Med. Chem. 16: 1043 (1973);
• 3. J.W. Cook et al., J. Chem. Soc., 3904 (1952);
• 4. E. Giovannini et al., Helv. Chim. Acta 31, 1392 (1948);
• 5. P. Lewer, J. Chem. Soc., Perkin Trans. 1, 4, 753 (1987);

N-alkylation of indolones:

• 1. T.A. Blizzard et al., J. Org. Chem. 54, 2657 (1989);
• 2. T.C. Crawford, U.S. 4,652,658;
• 3. K. Isshiki et al., J. Antibiot. 40, 1202 (1987);
• 4. D.W. Robertson et al., J. Med. Chem. 32, 1476 (1989);
• 5. G.M. Karp et al., J. Org. Chem. 57, 4765 (1992).

Procedure F)

The substituted 2-arylpyridines of the formula I, in which X and Y Mean CH₂, can be prepared according to synthesis scheme (5):

Transition metal-catalyzed cross-coupling reaction of halogen pyridine II with a boronic acid or trialkyltin compound Formula XXIII leads to the aldehyde XXIV. XXIV is also obtained by reaction of II with the Metallorganyl XXI and hydrolysis of the reaction product XXII.

XXIV itself is then involved in a Wittig-Horner-Emmons reaction converted the phosphonic ester XXV to the cinnamon tester XXVI, whose Hydrogenation, nitration and hydrolysis to the carboxylic acid (ester) n XXVIII leads.

For the implementations shown, the following is an example References:

Transition metal-catalyzed cross-coupling reactions:

• 1. WO 95/02580 and the one cited on pages 21 and 22 Literature;
• 2. A. Kasahara et al., Bull. Chem. Soc. Yep 55: 2434 (1982);  
• 3. H. Jendralla et al., Ann., 1253 (1995);

Acetal hydrolysis:

• 1. S. Linke in Houben-Weyl, Methods of Organic Chemistry, Bd E3, Stuttgart · New York 1983, pages 362 ff. And those there literature cited;

Wittig-Horner-Emmons reaction:

• 1. M.E. Niyazymbetov et al., Tetrahedron Lett. 29: 3007 (1988);
• 2. M.W. Rathke et al., J. Org. Chem. 50, 2624 (1985);
• 3. G. Cainelli et al., J. Chem. Soc., Perkin Trans. 1, 2516 (1980);
• 4. A. Fuentes et al., Tetrahedron Lett. 28: 2951 (1987);
• 5. W.C. Still et al., Tetrahedron Lett. 24, 4405 (1983);

Reduction of cinnamon testers to dihydrocinnamon testers:

• 1. J.K. Youn et al., Tetrahedron Lett. 1986, 27: 2409;
• 2. A. Nose et al., Chem. Pharm. Bull. 38, 2097 (1990);
• 3. H.J. Liu et al., Synthetic Commun. 15: 695 (1985);
• 4. J.W. Tillev et al., J. Med. Chem. 34, 1125 (1991);
• 5. S. Ram et al., Synth. Commun. 22: 2683 (1992);

Nitration of dihydrocinnamic acid esters:

• 1. G. Theodoridis et al., J. Heterocyclic Chem. 28, 849 (1991);
• 2. M. Tominaga et al., Chem. Pharm. Bull. 34, 682 (1986);

Reduction and cyclocondensation:

• 1. G. Theodoridis et al., J. Heterocyclic Chem. 28, 849 (1991);
• 2. N. Kawahara et al., Heterocycles 16, 729 (1981);
• 3. R.C. Fuson et al., J. Am. Chem. Soc. 76: 1169 (1954);
• 4. S. Niwas et al., Synthesis 12, 1027 (1983);
• 5. J.C. Pelletier et al., J. Org. Chem. 52, 616 (1987);
• 6. T. Kolasa et al., J. Org. Chem. 55, 4246 (1990);
• 7. Makosza, M. et al., Tetrahedron 51, 7263 (1995);

Alkylation of quinolinones:

• 1. H. Suginome et al., J. Org. Chem. 55, 4933 (1990);
• 2. D.M. Fink et al., Tetrahedron Lett. 33: 2103 (1992);
• 3. W.K. Anderson et al., J. Med. Chem. 31, 2097 (1988);
• 4. M. Tominaga et al., Chem. And Pharm. Bull. 29, 2166 (1981);
• 5. J.L. Mokrosz et al., Arch. Pharm. 327, 529 (1994).

In the way shown in synthesis scheme (5) can be also the compounds I, in which Y carbonyl or C (R⁵) -R⁶ (R⁵ and R⁶ ≠ H) means produce. Either then XXV uses a more functionalized compound or  alkylation is carried out at a later stage in the α-position only then to the carbonyl group or oxidized.

Procedure G)

The reduction of the nitro group on the pyridine can be both before and after the alkylation of the benzoxazinone XXXIIa. Starting from XXIX you get depending on Reduk agent, its amount and the reduction conditions XXXa or XXXb.

All individual steps are known, for example from the following the publications:

• - Reduction of nitropyridines with hydrogen: F. Janssens et al., J. Med. Chem. 28 (12), p. 1943 (1985);
• - Reduction of nitropyridines with iron: B.A. Fox et al., Org. Synth. 44, p. 34 (1964);
• - Reduction of nitropyridines with tin (II) chloride: L.A. Perez-Medina et al., J. Am. Chem. Soc. 69, p. 2574 (1947);
• - Reduction of nitropyridines with hydrazine: G. J. Clark et al., Aust. J. Chem. 34, p. 927 (1981);
• - Reduction of nitropyridines with tin: K. Wojciechowski et al., Synthesis 8, 651-653 (1986);
• - Reduction of nitropyridines with low-valent titanium compound dungen: M. Malinowski, B. Soc. Chim. Belg. 97 (1), 51-53 (1988);
• - Reduction of nitropyridines with baker's yeast: Takeshita, M. et al., Heterocycles 31 (12), 2201-2204 (1990);
• - Reduction of nitropyridines with zinc: K. Goerlitzer et al., Arch. Pharm. 324 (10), 785-796 (1991);
• - Reduction of nitropyridines with sodium dithionite: F.G. Fischer et al., Ann. Chem. 651, p. 49 (1962);
• - Diazotization of aminopyridines with isoamyl nitrite and reaction the diazonium salts with dimethyl disulfide or diphenyl disulfide: C.S. Giam et al., J. Chem. Soc., Chem. Commun. 16, p. 756 (1980);
• T. Yasumitsu et al., J. Org. Chem. 46, 3564-3567 (1981).

The starting compounds XXIX are based on those in synthesis scheme (1) shown way from compounds XXXIII

by ether cleavage and nitration of the phenols obtained in this way available.

The compounds XXXIII are in turn analogous to process C) Transition-metal-catalyzed cross-coupling reaction of 2-halo gene 5-nitropyridines of the formula XXXIVa (Hal = chlorine or bromine)

with organometallic compounds of the formula III or Boroxins IV accessible.

Reduction of the compounds XXXIVa {cf. e.g. B. J. Med. Chem. 16, 319-327 (1973)}, on the other hand, leads to the corresponding 5-amino-2-halopyridines XXXIVb

from which by diazotization - preferably with a nitrous oxide acid esters such as tert-butyl nitrite and isopentyl nitrite - and subsequent implementation of the diazonium salt with a symmetri aliphatic disulfide (C₁-C₆-alkyl) -S-S- (C₁-C₆-alkyl) the 2-halopyridines II (R¹ = C₁-C₆-alkylthio) available are (see also the conversion of XXXIId into I {n = 0; R¹ = C₁-C₆ alkylthio; X = O; Y = C (R⁵) -R⁶}).

The 2-halopyridines II with R¹ = C₁-C₆-alkylthio can then ßend to the corresponding compounds with R¹ = C₁-C₆-alkyl sulfinyl or C₁-C₆-alkylsulfonyl are oxidized, as under Process B) for the compounds I with R¹ = C₁-C₆-alkylthio has been described.  

Procedure H)

I {n = 0; R¹ = C₁-C₆ alkylthio; R⁴ ≠ H; X = X ′; Y = C (R⁵) -R⁶}
X 'represents oxygen, sulfur, -NH-, -N (CH₃) -.

For the individual implementations, see the procedures D) and G) literature cited.

The 2- (4-fluoro-3-nitrophenyl) -5-nitropyridines XXXV are through Nitration of the corresponding 2- (4-fluorophenyl) -5-nitropyridines available {cf. for this, the one listed in method D) Literature}. The 2- (4-fluorophenyl) -5-nitropyridines in turn are z. B. analogous to method C) by cross-coupling reaction the 2-halogen-5-nitropyridine XXXIV accessible with XVII.

Usually the substituted 2-arylpyridines are I after one of the above-mentioned synthetic methods. From innkeeper However, there may be economic or procedural reasons be more convenient, some compounds I from similar 2-aryl pyridines, which, however, differ in the meaning of a residue divide, manufacture.

Unless otherwise stated, the individual ver drive specified starting compounds either known or on in a manner known per se or in analogy to one of the descriptions available process.

The reaction mixtures are generally worked up by methods known per se, for example
by diluting the reaction solution with water and then isolating the product by means of 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-arylpyridines I can in the preparation are obtained as mixtures of isomers, but if desired after the usual methods such as crystallization or chromato graph, also on an optically active adsorbate, in the far pure isomers can be separated. Pure optical active isomers can advantageously be optically identified produce active starting products.

Agricultural salts of the compounds I can by reaction with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride will.  

Salts of I whose metal ion is not an alkali metal ion can also by salting the corresponding alkali metal salt in be manufactured, as well as 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 pure isomers - as herbicides. The herbicides containing I Agents fight plant growth on non-cultivated areas very well, especially with high application rates. In crops like wheat, rice, Corn, soybeans and cotton act against weeds and damage grasses without significantly damaging the crops. This The effect occurs especially at low application rates.

Depending on the respective application method, you can the compounds I or herbicidal compositions comprising them still in a number of crops for disposal unwanted plants can be used. Be considered for example the following cultures:

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 liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Tpomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, 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 communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds I can also be used in cultures which through breeding including genetic engineering methods against the The effects of herbicides are tolerant.  

The substituted 2-arylpyridines I are also suitable for the desiccation and / or defoliation of plants.

As desiccants, they are particularly suitable for drying out the aerial parts of crops such as potatoes, rapeseed, Sunflower and soybean. So that a completely mechani harvests these important crops.

Ease of harvest is also of economic interest, which are caused by the temporally concentrated falling or decreasing of the Adhesion to the tree with citrus fruits, olives or other other types and varieties of pome, stone and shell fruit becomes. The same mechanism, that is, the promotion of training Formation of separating tissue between the fruit or leaf and sprout part of the plants is also for a well controlled defoliation of useful plants, especially cotton.

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

The compounds I or the compositions containing them can for example in the form of directly sprayable aqueous solutions gene, powders, suspensions, also high-proof aqueous, oily or other suspensions or dispersions, emulsions, Oil dispersions, pastes, dusts, spreading agents or granules laten by spraying, atomizing, dusting, scattering or Pouring can be applied. The application forms depend on the uses; in any case, they should, if possible finest distribution of the active ingredients according to the invention Afford.

The following are essentially considered as inert auxiliaries: Mineral oil fractions from medium to high boiling point such as Kerosene and diesel oil, as well as coal tar oils and vegetable oils or of animal origin, aliphatic, cyclic and aromatic cal hydrocarbons, e.g. B. 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 solution medium, e.g. B. amines such as N-methylpyrrolidone and water.

Aqueous use forms can be made from emulsion concentrates, Suspensions, pastes, wettable powders or water dispersants granules can be prepared by adding water. For The production of emulsions, pastes or oil dispersions Substrates as such or dissolved in an oil or solvent,  using wetting agents, adhesives, dispersants or emulsifiers in water be homogenized. But it can also be made from an active substance, Wetting, adhesive, dispersing or emulsifying agents and possibly Concentrates containing solvents or oil are produced, which are suitable for dilution with water.

The surface-active substances (adjuvants) are the alkali, Alkaline earth metal, ammonium salts of aromatic sulfonic acids, e.g. B. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of Fet 10565 00070 552 001000280000000200012000285911045400040 0002019633751 00004 10446 acids, alkyl and alkylarylsulfonates, alkyl, Lauryl ether and fatty alcohol sulfates, as well as sulfated salts Hexa-, hepta- and octadecanols as well as fatty alcohol glycol ether, Condensation products of sulfonated naphthalene and its Derivatives with formaldehyde, condensation products of naphthalene or the naphthalenesulfonic acids with phenol and formaldehyde, poly oxyethylene octylphenol ether, ethoxylated isooctyl, octyl or Nonylphenol, alkylphenyl, tributylphenyl polyglycol ether, alkyl aryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or Polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, Sorbitol esters, lignin sulfite waste liquors or methyl cellulose in Consideration.

Powders, materials for spreading and dusts can be mixed or joint grinding of the active substances with a solid Carrier are manufactured.

Granules, e.g. B. coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers be put. Solid carriers are mineral soils like pebbles acids, silica gels, silicates, talc, kaolin, limestone, lime, Chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and Magnesium sulfate, magnesium oxide, ground plastics, fertilizers agents such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or others solid carriers.

The concentrations of the active ingredients I in the ready-to-use Preparations can be varied in a wide range. in the generally the formulations contain from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one Active ingredient. The active ingredients are in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum) set.  

The following formulation examples illustrate the manufacturer such preparations:

• I. 20 parts by weight of compound no. Ik.1 are in one Dissolved mixture that alkylated from 80 parts by weight Benzene, 10 parts by weight of the adduct of 8 up 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 There is ethylene oxide in 1 mole of castor oil. By pouring and finely distribute the solution in 100,000 parts by weight of water an aqueous dispersion is obtained which contains 0.02% by weight of the Contains active ingredient.
• II. 20 parts by weight of compound no. Ia.1 are in a Dissolved mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the plant approximately 7 moles of ethylene oxide to 1 mole of isooctyl phenol and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By one pour and finely distribute the solution in 100000 weight divide water you get an aqueous dispersion that Contains 0.02% by weight of the active ingredient.
• III. 20 parts by weight of active ingredient No. In.1 are in a Dissolved mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction from the boiling point 210 to 280 ° C and 10 parts by weight of the addition product of 40 moles of ethylene oxide with 1 mole of castor oil consists. By pouring in and finely distributing the solution an aqueous solution is obtained in 100,000 parts by weight of water Dispersion containing 0.02% by weight of the active ingredient.
• IV. 20 parts by weight of active ingredient No. Ic.2 are with 3 parts by weight of the sodium salt of diisobutyl naphthalene-α-sulfonic acid, 17 parts by weight of sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel well ver mixes and ground in a hammer mill. By fine Distribute 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 contains.  
• V. 3 parts by weight of active ingredient no. Ia.301 with 97 parts by weight of finely divided kaolin mixed. You get in this way a dusting agent containing 3% by weight of the active ingredient contains.
• VI. 20 parts by weight of active ingredient no. Ic.301 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 share sodium salt of a phenol-urea-formaldehyde Condensates and 68 parts by weight of a paraffinic Mineral oil mixed intimately. A stable oily is obtained Dispersion.
• VII. 1 part by weight of active ingredient No. Ik.301 is in a Dissolved mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and There are 10 parts by weight of ethoxylated castor oil. Man receives a stable emulsion concentrate.
• VIII. 1 part by weight of active ingredient No. In.301 is in a Dissolved mixture consisting of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (= non-ionic emulsifier based on ethoxylated castor oil; BASF AG) be stands. A stable emulsion concentrate is obtained.

The application of the active ingredients I or the herbicidal compositions can pre-emergence or post-emergence. Are the Active ingredients for certain crops less tolerable, so application techniques can be used in which the herbicidal agents are sprayed with the help of sprayers, that the leaves of sensitive crops if possible not to be taken while the active ingredients are on the leaves including growing unwanted plants or the uncovered Floor space (post-directed, lay-by).

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

To broaden the spectrum of activity and to achieve syner The substituted 2-arylpyridines I with numerous representatives of other herbicides or growth regulating drug groups mixed and applied together will. For example, 1,2,4-thia come as mixing partner diazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and their Derivatives, aminotriazoles, anilides, aryloxy / heteroaryloxyalkane acids and their derivatives, benzoic acid and their derivatives, benzo  thiadiazinone, 2- (hetaroyl / aroyl) -1,3-cyclohexanedione, hetero aryl-aryl-ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, Carbamates, quinoline carboxylic acid and their derivatives, chloroacet anilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropion acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, Dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, Halogenated carboxylic acids and their derivatives, ureas, 3-phenyl uracile, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydro phthalimides, oxadiazoles, oxiranes, phenols, aryloxy and hetero aryloxyphenoxypropionic acid esters, phenylacetic acid and their Derivatives, 2-phenylpropionic acid and their derivatives, pyrazoles, Phenylpyrazoles, pyridazines, pyridinecarboxylic acid and their Derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, Triazines, triazinones, triazolinones, triazolecarboxamides and Uracile into consideration.

It may also be useful to use the compounds I alone or in combination with other herbicides also with others Plant protection products mixed, to apply together, at for example with means to control pests or phytopathogenic fungi or bacteria. It is also of interest the miscibility with mineral salt solutions, which are used to eliminate Nutritional and trace element deficiencies are used. It can non-phytotoxic oils and oil concentrates can also be added.

Examples of use (herbicidal activity)

The herbicidal activity of the substituted 2-aryllpyridines 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 or suspended in water emulsified active ingredients directly after sowing using fine ver dividing nozzles applied. The vessels were lightly sprinkled, to promote germination and growth, and then with through visible plastic covers until the plants have grown were. This cover causes the test to germinate evenly plant, unless this is affected by the active ingredients has been.

The test plants were used for post-emergence treatment depending on the growth form, only up to a height of 3 to 15 cm attracted and only then with the suspended in water or treated emulsified active ingredients. The test plants were therefor  either sown directly and grown in the same containers or they were first grown separately as seedlings and some Planted into the test tubes days before treatment.

The plants became species-specific at temperatures from 10 to 25 ° C or 20 to 35 ° C kept. The trial period extended yourself over 2 to 4 weeks. During this time, the plants cared for, and their response to each treatment was evaluated.

It was rated on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the above-ground parts and 0 no damage or normal Growth course.

Examples of use (desiccative / defolian effectiveness)

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

The young cotton plants got soaked with water preparations of the active ingredients [with the addition of 0.15 wt .-% of Fatty alcohol alkoxylate Plurafac® LF 700 (a low-foaming, non-ionic Surfactant from BASF AG), based on the Spray liquor] treated with leaves. The amount of water applied was converted 1000 l / ha. After 13 days, the number of thrown leaves and the degree of defoliation determined in%.

No leaf fall occurred in the untreated control plants.

Claims (18)

1. Substituted 2-arylpyridines of the general formula I in which the variables have the following meanings:
n zero or 1;
R¹ mercapto, hydroxysulfonyl, chlorosulfonyl, amino sulfonyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylaminosulfonyl or di- (C₁-C₆-alkyl) aminosulfonyl;
R², R³ independently of one another are hydrogen or halogen;
R⁴ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, cyano-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₄-haloalkoxy-C₁-C₄ -alkyl, C₁-C₆-alkylthio- C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄- alkoxy -C₁-C₄-alkyl, (C₁-C₆-alkoxy) carbonyl-C₁-C₆-alkyl, C₁-C₃-alkoxy- (C₁-C₃-alkoxy) carbonyl-C₁-C₆-alkyl, C₂-C₄-alkenyloxy-C₁ -C₄-alkyl, C₃-C₄-alkynyloxy-C₁-C₄- alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₆-alkyl, C₃-C₇-cycloalkyloxy-C₁-C₆-alkyl, C₃-C₇ -Cycloalkyl thio-C₁-C₆-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl, C₃-C₈-haloalkenyl, C₃-C₈-haloalkynyl, C₁-C₆-alkoxy-C₃-C₈-alkenyl, C₁-C₆- Alkoxy-C₃-C₈-alkynyl, (C₁-C₆-alkoxy) carbonyl, C₁-C₆-alkylsulfonyl, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy or benzyl, which are unsubstituted or on the phenyl ring one to three Can carry substituents, each selected from the group consisting of nitro, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy) carbonyl;
X is oxygen, sulfur, -NH-, -N (CH₃) - or methylene;
Y is a chemical bond, carbonyl or C (R⁵) -R⁶, where
R⁵, R⁶ independently of one another for hydrogen, nitro, cyano, methoxy, methylthio, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, (C₁-C₄-alkoxy) carbonyl, C₂-C₆-alkenyl or C₃-C₆-alkynyl stand,
and the agriculturally useful salts of the compounds I with R 1 = hydroxysulfonyl. 2. Substituted 2-arylpyridines of formula I according to claim 1, wherein the variables have the following meanings:
n zero;
R¹ mercapto, hydroxysulfonyl, chlorosulfonyl, amino sulfonyl, C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl or C₁-C₆ alkylsulfonyl;
R², R³ independently of one another halogen;
R⁴ hydrogen, C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkyl thio-C₁-C₆-alkyl, (C₁ -C₆-alkoxy) carbonyl-C₁-C₆-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl, C₃-C₆-alkenyloxy or C₃-C₆-alkynyloxy;
X oxygen;
Y is a chemical bond or C (R⁵) -R⁶, where
R⁵, R⁶ are independently hydrogen, C₁-C₄-alkyl or (C₁-C₄-alkoxy) carbonyl. 3. Substituted 2-arylpyridines of the formula I according to claim 1, where n is zero, R¹ is C₁-C₆-alkylsulfonyl, R² is chlorine, R³ for fluorine or chlorine, X for oxygen, Y for one chemical bond or for methylene and R⁴ for hydrogen, C₁-C₆-alkyl, cyano-C₁-C₆-alkyl, (C₁-C₆-alkoxy) carbonyl- C₁-C₆-alkyl, C₃-C₈-alkenyl or C₃-C₈-alkynyl. 4. Use of the substituted 2-arylpyridines of the formula I. and the agriculturally useful salts of I, according to Claim 1, as a herbicide or for desiccation and / or Defoliation of plants.   5. Herbicidal composition containing a herbicidally effective amount at least one substituted 2-arylpyridine 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. 6. means for the desiccation and / or defoliation of plants, containing a desiccant and / or defoliantly effective amount at least one substituted 2-arylpyridine 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. 7. Process for the preparation of herbicidally active agents, characterized in that a herbicidally effective amount at least one substituted 2-arylpyridine 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 mixes. 8. Process for the production of desiccant and / or defoliant effective means, characterized in that one desiccant and / or defoliant effective amount of at least one substituted 2-arylpyridine of formula I or a country economically usable salt of I, according to claim 1, and at least one inert liquid and / or solid Carrier and, if desired, at least one upper surfactant mixes. 9. a method for controlling undesirable plant growth, characterized in that a herbicidally effective amount at least one substituted 2-arylpyridine of the formula I. or an agriculturally useful salt of I, according to Claim 1, on plants, their habitat or on seeds can act. 10. Process for the desiccation and / or defoliation of plants, characterized in that a desiccant and / or defoliant effective amount of at least one substituted 2-arylpyridine of formula I or an agricultural usable salt of I, according to claim 1, on plants can act.   11. The method according to claim 10, characterized in that Cotton treated. 12. Process for the preparation of substituted 2-arylpyridines of formula I according to claim 1, wherein n is 1 and R¹ is C₁-C₆ alkylsulfonyl and the variables R⁴, X and Y contain no oxidizable sulfur, characterized net that correspondingly substituted 2-arylpyridines, at where n means zero, in an inert solution / ver oxidizing agent. 13. Process for the preparation of substituted 2-arylpyridines of the formula I according to claim 1, in which R¹ is C₁-C₆-alkyl is sulfinyl or C₁-C₆-alkylsulfonyl and the variables R⁴, X and Y contain no oxidizable sulfur characterized in that correspondingly substituted 2-aryl pyridines, but in which R¹ is C₁-C₆-alkylthio or C₁-C₆-alkyl sulfinyl means in an inert solution / Diluent oxidized. 14. A process for the preparation of substituted 2-arylpyridines of the formula I according to claim 1, in which R¹ is C₁-C₆-alkyl thio and X is oxygen, sulfur, -NH- or -N (CH₃) -, characterized in that 5-Amino-2-arylpyridines XXXVIIa were substituted accordingly wherein R², R³, R⁵ and R⁶ have the meanings given in claim 1 and X 'represents oxygen, sulfur, -NH- or -N (CH₃) -, in the presence of a base with R⁴-Cl or R⁴-Br,
the process product XXXVIIb diazotized in an inert solvent / diluent and the diazonium salt thus prepared is reacted with an aliphatic disulfide (C₁-C₆-alkyl) -SS- (C₁-C₄-alkyl). 15. 2- (p-hydroxyphenyl) pyridines of the formulas X, XXXIa and XXXIb wherein the substituents R¹, R², R³, R⁵ and R⁶ have the meanings given in claim 1. 16. 2-aryl-5-nitropyridines of the formulas XXXIIa and XXXIIc wherein the substituents R² to R⁶ have the meanings given in claim 1. 17. 5-Amino-2-arylpyridines of the formulas XXXVIIa and XXXVIIb wherein the substituents R² to R⁶ have the meanings given in claim 1 and X 'represents oxygen, sulfur, -NH- or -N (CH₃) -. 18. 2- (m-nitrophenyl) pyridines of formulas XVI, XXXVIa and XXXVIb wherein the substituents R¹, R², R³, R⁵ and R⁶ have the meanings given in claim 1 and X 'represents oxygen, sulfur, -NH- or -N (CH₃) -.