# Patent

## Title
3-Heterocyclyl substituted benzoic acid derivatives

## Abstract

Disclosed are 3-heterocyclyl substituted benzoic acid derivatives of general formula (I),




in which the variables R1 to R8 and X have the meanings indicated in claim 1, and the use thereof as herbicides or for desiccating/defoliating plants.

## Background
CROSS REFERENCE TO RELATED APPLICATION
This application is a 35 USC §371 National Phase Entry Application from PCT/EP2003/008013, filed Jul. 22, 2003, and designating the U.S.
The present invention relates to 3-heterocyclyl-substituted benzoic acid derivatives and their agriculturally useful salts, to compositions comprising such compounds and to the use of the 3-heterocyclyl-substituted benzoic acid derivatives, of their salts or of compositions comprising them as herbicides, desiccants or defoliants.
In various publications, uracil-substituted benzoic acid derivatives have been described as herbicidally active compounds. Thus, for example, WO 88/10254, WO 89/03825 and WO 91/00278 describe the esters of 2-halo-5-(substituted uracil)benzoic acids and the esters of 2-cyano-5-(substituted uracil)benzoic acids which may optionally be halogen-substituted in the 4-position. WO 89/02891 and WO 93/06090 describe the amides of 2-halo-5-(substituted uracil)benzoic acids and the amides of 2-cyano-5-(substituted uracil)benzoic acids which may optionally be halogen-substituted in the 4-position, as herbicidally active substances.
Furthermore, WO 01/83459 discloses herbicidally active 3-heterocyclyl-substituted phenylsulfamoylcarboxamides of the formula A




where Het is, inter alia, an unsaturated five- or six-membered heterocyclic radical which is attached via a nitrogen atom to the phenyl ring, X1 is hydrogen, halogen or C1-C4-alkyl, X2 is hydrogen, cyano, thiocarbamoyl, halogen, C1-C4-alkyl or C1-C4-haloalkyl, X3 is, inter alia, hydrogen, C1-C6-alkyl, C1-C6-alkoxyalkyl, R′ are each independently of one another inter alia hydrogen, alkoxy, C1-C10-alkyl, C2-C10-alkenyl, C3-C10-alkynyl, C3-C7-cycloalkyl, or the two radicals R′ together with the nitrogen atom to which they are attached form a 3- to 7-membered heterocyclic ring.

It is an object of the present invention to provide novel herbicidally active compounds which allow better targeted control of unwanted plants than the known herbicides. Advantageously, the novel herbicides should be highly active against harmful plants. Moreover, a high compatibility with crop plants is desirable. It is another object to provide novel compounds having desiccant/defoliant action.
We have found, surprisingly, that these objects are achieved by 3-heterocyclyl-substituted benzoic acid derivatives of the general formula I defined below:




where:

    X is oxygen or NR9,
    R1 is a heterocyclic radical of the formulae II-A to II-H,






    R2 is hydrogen or halogen,
    R3 is halogen or cyano,
    R4, R5 independently of one another are hydrogen, C1-C4-alkyl or C1-C4-alkoxy, or R4 and R5 together are a group ═CH2,
    R6 is hydrogen, C1-C4-alkyl or C1-C4-alkoxy,
    R7, R8 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylsuifinyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl, cyano-C1-C4-alkyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl, amino-C1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, di(C1-C4-alkyl)amino-C1-C4-alkyl, aminocarbonyl-C1-C4-alkyl, (C1-C4-alkylamino)carbonyl-C1-C4-alkyl, di(C1-C4-alkyl)aminocarbonyl-C1-C4-alkyl, phenyl or C1-C4-alkylphenyl or
    R7 and R8 together with the nitrogen atom to which they are attached form a saturated or unsaturated 3-, 4-, 5-, 6- or 7-membered nitrogen heterocycle which may optionally contain one or two further heteroatoms selected from the group consisting of nitrogen, sulfur and oxygen as ring members, which may contain 1 or 2 carbonyl and/or thiocarbonyl groups as ring members and/or which may be substituted by one, two or three substituents selected from the group consisting of C1-C4-alkyl and halogen;
    R9 is hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, phenyl, phenyl-C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl,
    R10 is hydrogen, C1-C4-alkyl or amino,
    R11 is C1-C4-alkyl or C1-C4-haloalkyl,
    R12 is hydrogen or C1-C4-alkyl,
    R13, R13′ independently of one another are hydrogen or C1-C4-alkyl,
    R14 is halogen,
    R15 is hydrogen or C1-C4-alkyl,
    R16 is C1-C4-haloalkyl, C1-C4-alkylthio, C1-C4-alkylsulfonyl or C1-C4-alkylsulfonyloxy,
    R17 is hydrogen or C1-C4-alkyl,
    R18 is hydrogen, C1-C4-alkyl or amino,
    R19 is C1-C4-haloalkyl, C1-C4-alkylthio or C1-C4-alkylsulfonyl.
    R20 is hydrogen or C1-C4-alkyl,
    R21 is hydrogen, halogen or C1-C4-alkyl,
    R22 is C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-alkylsulfonyl,
    R23 is hydrogen or C1-C4-alkyl,

or

    R22 and R23 together with the atoms to which they are attached form a 5-, 6- or 7-membered saturated or unsaturated ring which may contain a heteroatom selected from the group consisting of oxygen and nitrogen as a ring-forming atom and/or which may be substituted by one, two or three radicals selected from the group consisting of C1-C4-alkyl and halogen,
    R24 is hydrogen, C1-C4-alkyl or C1-C4-haloalkyl,
    R25 is C1-C4-alkyl or C1-C4-haloalkyl,

or

    R24 and R25 together with the atoms to which they are attached form a 5-, 6- or 7-membered saturated or unsaturated ring which optionally contains an oxygen atom as ring-forming atom and/or which may be substituted by one, two or three radicals selected from the group consisting of C1-C4-alkyl and halogen,
    R26 is hydrogen, C1-C4-alkyl or C1-C4-haloalkyl,
    R27 is hydrogen, C1-C4-alkyl or C1-C4-haloalkyl,

or

    R26 and R27 together with the atoms to which they are attached form a 5-, 6- or 7-membered saturated or unsaturated ring which optionally contains an oxygen atom as ring-forming atom and/or which may be substituted by one, two or three radicals selected from the group consisting of C1-C4-alkyl and halogen,
    A1, A2, A3, A4 are each independently of one another oxygen or sulfur.


Accordingly, the present invention relates to 3-heterocyclyl-substituted benzoic acid derivatives of the formula I and their agriculturally useful salts.
The invention also relates to the tautomers of the compounds I, for example to compounds I in which R1 is a heterocyclic radical of the formula II-A, II-B, II-F or II-H.
Moreover, the present invention relates to

    
    
        the use of the compounds I and/or their salts as herbicides or for the desiccation/defoliation of plants
        herbicidal compositions comprising the compounds I and/or their salts as active substances,
        compositions for the dessication/defoliation of plants, which compositions comprise the compounds I and/or their salts as active substances, and also
        methods for controlling unwanted vegetation or for the desiccation/defoliation of plants using the compounds I and/or their salts.
    
    


Depending on the substitution pattern, the compounds of the formula I may contain one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. The invention provides both the pure enantiomers or diastereomers and mixtures thereof.
Agriculturally useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the herbicidal action and/or desiccant/defoliant action of the compounds I. Thus, particularly suitable cations are the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion, which, if desired, may carry one to four C1-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, hydrogencarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
The organic moieties mentioned in the definition of the substituents R1 to R27 or as radicals on heterocyclic rings are—like the term halo—collective terms of individual listings of the individual group members. All carbon chains, i.e. all alkyl, haloalkyl, cyanoalkyl, aminoalkyl, aminocarbonylalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy and alkenyl moieties may be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms. The term halogen denotes in each case fluorine, chlorine, bromine or iodine.
Examples of other meanings are:

    
    
        C1-C4-alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;
        C1-C6-alkyl: C1-C4-alkyl as mentioned above and also, for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-3-methylpropyl;
        C1-C4-haloalkyl: a C1-C4-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl; in particular difluoromethyl, trifluoromethyl;
        C1-C4-alkoxy: for example methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy;
        C1-C4-haloalkoxy: a C1-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example, OCH2F, OCHF2, OCF3, OCH2Cl, OCH(Cl)2, OC(Cl)3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2—C2F5, OCF2—C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, preferably OCHF2;
        C1-C4-alkoxy-C1-C4-alkyl: C1-C4-alkyl which is substituted by C1-C4-alkoxy as mentioned above, i.e., for example, CH2—OCH3, CH2—OC2H5, n-propoxymethyl, CH2—OCH(CH3)2, n-butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, CH2—OC(CH3)3, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(n-propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(n-butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(n-propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(n-butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl, 2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(n-butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or 4-(1,1-dimethylethoxy)butyl;
        C1-C4-alkylthio: for example SCH3, SC2H5, SCH2—C2H5, SCH(CH3)2, n-butylthio, SCH(CH3)—C2H5, SCH2—CH(CH3)2 or SC(CH3)3;
        C1-C4-alkylthio-C1-C4-alkyl: C1-C4-alkyl, which is substituted by C1-C4-alkylthio as mentioned above, i.e., for example, CH2—SCH3, CH2—HC2H5, n-propylthiomethyl, CH2—SCH(CH3)2, n-butylthiomethyl, (1-methylpropylthio)methyl, (2-methylpropylthio)methyl, CH2—SC(CH3)3, 2-(methylthio)ethyl, 2-(ethylthio)ethyl, 2-(n-propylthio)ethyl, 2-(1-methylethylthio)ethyl, 2-(n-butylthio)ethyl, 2-(1-methylpropylthio)ethyl, 2-(2-methylpropylthio)ethyl, 2-(1,1-dimethylethylthio)ethyl, 2-(methylthio)propyl, 2-(ethylthio)propyl, 2-(n-propylthio)propyl, 2-(1-methylethylthio)propyl, 2-(n-butylthio)propyl, 2-(1-methylpropylthio)propyl, 2-(2-methylpropylthio)propyl, 2-(1,1-dimethylethylthio)propyl, 3-(methylthio)propyl, 3-(ethylthio)propyl, 3-(n-propylthio)propyl, 3-(1-methylethylthio)propyl, 3-(n-butylthio)propyl, 3-(1-methylpropylthio)propyl, 3-(2-methylpropylthio)propyl, 3-(1,1-dimethylethylthio)propyl, 2-(methylthio)butyl, 2-(ethylthio)butyl, 2-(n-propylthio)butyl, 2-(1-methylethylthio)butyl, 2-(n-butylthio)butyl, 2-(1-methylpropylthio)butyl, 2-(2-methylpropylthio)butyl, 2-(1,1-dimethylethylthio)butyl, 3-(methylthio)butyl, 3-(ethylthio)butyl, 3-(n-propylthio)butyl, 3-(1-methylethylthio)butyl, 3-(n-butylthio)butyl, 3-(1-methylpropylthio)butyl, 3-(2-methylpropylthio)butyl, 3-(1,1-dimethylethylthio)butyl, 4-(methylthio)butyl, 4-(ethylthio)butyl, 4-(n-propylthio)butyl, 4-(1-methylethylthio)butyl, 4-(n-butylthio)butyl, 4-(1-methylpropylthio)butyl, 4-(2-methylpropylthio)butyl or 4-(1,1-dimethylethylthio)butyl;
        C1-C4-alkylsulfinyl (C1-C4-alkyl-S(═O)—) and the alkylsulfinyl moieties of C1-C4-alkylsulfinyl-C1-C4-alkyl: for example methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or 1,1-dimethylethylsulfinyl;
        C1-C4-alkylsulfonyl (C1-C4-alkyl-S(═O)2—) and the alkylsulfonyl moieties of C1-C4-alkylsulfonyl-C1-C4-alkyl: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl or 1,1-dimethylethylsulfonyl, preferably methylsulfonyl;
        C1-C4-alkylsulfonyloxy: for example methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1-methylethylsulfonyloxy, butylsulfonyloxy, 1-methylpropylsulfonyloxy, 2-methylpropylsulfonyloxy or 1,1-dimethylethylsulfonyloxy, preferably methylsulfonyloxy;
        cyano-C1-C4-alkyl: for example 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-cyanobut-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 or 1-(CH2CN)prop-1-yl;
        phenyl-C1-C4-alkyl: for example benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1-(benzyl)eth-1-yl, 1-(benzyl)-1-(methyl)eth-1-yl or 1-(benzyl)prop-1-yl;
        C1-C4-alkoxycarbonyl: for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl;
        (C1-C4-alkoxy)carbonyl-C1-C4-alkyl: C1-C4-alkyl which is substituted by (C1-C4-alkoxy)carbonyl as mentioned above, i.e., for example, CH2—CO—OCH3, CH2—CO—OC2H5, CH2—CO—OCH2—C2H5, CH2—CO—OCH(CH3)2, n-butoxycarbonylmethyl, CH2—CO—OCH(CH3)—C2H5, CH2—CO—OCH2—CH(CH3)2, CH2—CO—OC(CH3)3, 1-(CO—OCH3) ethyl, 1-(CO—OC2H5) ethyl, 1-(CO—OCH2—C2H5)ethyl, 1-[CO—OCH(CH3)2]ethyl, 1-(n-butoxycarbonyl)ethyl, 1-[1-methylpropoxycarbonyl]ethyl, 1-[2-methylpropoxycarbonyl]ethyl, 2-(CO—OCH3)ethyl, 2-(CO—OC2H5) ethyl, 2-(CO—OCH2—C2H5) ethyl, 2-[CO—OCH(CH3)2]ethyl, 2-(n-butoxycarbonyl)ethyl, 2-[1-methylpropoxycarbonyl]ethyl, 2-[2-methylpropoxycarbonyl]ethyl, 2-[CO—OC(CH3)3]ethyl, 2-(CO—OCH3)propyl, 2-(CO—OC2H5)propyl, 2-(CO—OCH2—C2H5) propyl, 2-[CO—OCH(CH3)2]propyl, 2-(n-butoxycarbonyl) propyl, 2-[1-methylpropoxycarbonyl]propyl, 2-[2-methylpropoxycarbonyl]propyl, 2-[CO—OC(CH3)3]propyl, 3-(CO—OCH3) propyl, 3-(CO—OC2H5)propyl, 3-(CO—OCH2—C2H5) propyl, 3-[CO—OCH(CH3)2]propyl, 3-(n-butoxycarbonyl)propyl, 3-[1-methylpropoxycarbonyl]propyl, 3-[2-methylpropoxycarbonyl]propyl, 3-[CO—OC(CH3)3]propyl, 2-(CO—OCH3)butyl, 2-(CO—OC2H5)butyl, 2-(CO—OCH2—C2H5)butyl, 2-[CO—OCH(CH3)2]butyl, 2-(n-butoxycarbonyl)butyl, 2-[1-methylpropoxycarbonyl]butyl, 2-[2-methylpropoxycarbonyl]butyl, 2-[CO—OC(CH3)3]butyl, 3-(CO—OCH3)butyl, 3-(CO—OC2H5)butyl, 3-(CO—OCH2—C2H5)butyl, 3-[CO—OCH(CH3)2]butyl, 3-(n-butoxycarbonyl)butyl, 3-[1-methylpropoxycarbonyl]butyl, 3-[2-methylpropoxycarbonyl]butyl, 3-[CO—OC(CH3)3]butyl, 4-(CO—OCH3)butyl, 4-(CO—OC2H5)butyl, 4-(CO—OCH2—C2H5)butyl, 4-[CO—OCH(CH3)2]butyl, 4-(n-butoxycarbonyl)butyl, 4-[1-methylpropoxycarbonyl]butyl, 4-[2-methylpropoxycarbonyl]butyl or 4-[CO—OC(CH3)3]butyl, preferably CH2—CO—OCH3, CH2—CO—OC2H5, 1-(CO—OCH3) ethyl or 1-(CO—OC2—H5) ethyl;
        amino-C1-C4-alkyl: for example CH2NH2, 1-aminoethyl, 2-aminoethyl, 1-aminoprop-1-yl, 2-aminoprop-1-yl, 3-aminoprop-1-yl, 1-aminobut-1-yl, 2-aminobut-1-yl, 3-aminobut-1-yl, 4-aminobut-1-yl, 1-aminobut-2-yl, 2-aminobut-2-yl, 3-aminobut-2-yl, 4-aminobut-2-yl, 1-(CH2NH2) eth-1-yl, 1-(CH2NH2)-1-(CH3) eth-1-yl or 1-(CH2NH2) prop-1-yl;
        C1-C4-alkylamino: for example H3C—NH—, H5C2—NH—, n-propyl-NH—, 1-methyl ethyl-NH-, n-butyl-NH-, 1-methylpropyl-NH-, 2-methylpropyl-NH— or 1,1-dimethylethyl-NH—;
        C1-C4-alkylamino-C1-C4-alkyl: C1-C4-alkyl which is substituted by C1-C4-alkylamino as defined above, i.e., for example, CH2CH2—NH—CH3, CH2CH2—N(CH3)2, CH2CH2—NH—C2H5 or CH2CH2—N(C2H5)2;
        di(C1-C4-alkyl)amino: N(CH3)2, N(C2H5)2, N,N-dipropylamino, N,N-di(1-methylethyl)amino, N,N-dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di-(2-methylpropyl)amino, N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino, N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)-amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;
        di(C1-C4-alkyl)amino-C1-C4-alkyl: C1-C4-alkyl which is substituted by di(C1-C4-alkyl)amino as mentioned above, i.e., for example, CH2N(CH3)2, CH2N(C2H5)2, N,N-dipropylaminomethyl, N,N-di[CH(CH3)2]aminomethyl, N,N-dibutylaminomethyl, N,N-di(1-methylpropyl)aminomethyl, N,N-di(2-methylpropyl)aminomethyl, N,N-di[C(CH3)3]aminomethyl, N-ethyl-N-methylaminomethyl, N-methyl-N-propylaminomethyl, N-methyl-N—[CH(CH3)2]aminomethyl, N-butyl-N-methylaminomethyl, N-methyl-N-(1-methylpropyl)aminomethyl, N-methyl-N-(2-methylpropyl)aminomethyl, N—[C(CH3)3]-N-methylaminomethyl, N-ethyl-N-propylaminomethyl, N-ethyl-N—[CH(CH3)2]aminomethyl, N-butyl-N-ethylaminomethyl, N-ethyl-N-(1-methylpropyl)aminomethyl, N-ethyl-N-(2-methylpropyl)aminomethyl, N-ethyl-N—[C(CH3)3]aminomethyl, N—[CH(CH3)2]-N-propylaminomethyl, N-butyl-N-propylaminomethyl, N-(1-methylpropyl)-N-propylaminomethyl, N-(2-methylpropyl)-N-propylaminomethyl, N—[C(CH3)3]-N-propylaminomethyl, N-butyl-N-(1-methylethyl)-aminomethyl, N—(CH(CH3)21-N-(1-methylpropyl)aminomethyl, N—[CH(CH3)2]-N-(2-methylpropyl)aminomethyl, N—[C(CH3)3]-N—[CH(CH3)2]aminomethyl, N-butyl-N-(1-methylpropyl)aminomethyl, N-butyl-N-(2-methylpropyl)aminomethyl, N-butyl-N—[C(CH3)3]aminomethyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminomethyl, N—[C(CH3)3]-N-(1-methylpropyl)aminomethyl, N—[C(CH3)3]-N-(2-methylpropyl)aminomethyl, N,N-dimethylaminoethyl, N,N-diethylaminoethyl, N,N-di(n-propyl)aminoethyl, N,N-di[CH(CH3)2]-aminoethyl, N,N-dibutylaminoethyl, N,N-di(1-methylpropyl)aminoethyl, N,N-di(2-methylpropyl)aminoethyl, N,N-di[C(CH3)3]aminoethyl, N-ethyl-N-methylaminoethyl, N-methyl-N-propylaminoethyl, N-methyl-N—[CH(CH3)2]aminoethyl, N-butyl-N-methylaminoethyl, N-methyl-N-(1-methylpropyl)aminoethyl, N-methyl-N-(2-methylpropyl)aminoethyl, N—[C(CH3)3]-N-methylaminoethyl, N-ethyl-N-propylaminoethyl, N-ethyl-N—[CH(CH3)2]aminoethyl, N-butyl-N-ethylaminoethyl, N-ethyl-N-(1-methylpropyl)aminoethyl, N-ethyl-N-(2-methylpropyl)aminoethyl, N-ethyl-N—[C(CH3)3]aminoethyl, N—[CH(CH3)2]-N-propylaminoethyl, N-butyl-N-propylaminoethyl, N-(1-methylpropyl)-N-propylaminoethyl, N-(2-methylpropyl)-N-propylaminoethyl, N—[C(CH3)3]-N-propylaminoethyl, N-butyl-N—[CH(CH3)2]aminoethyl, N—[CH(CH3)2]-N-(1-methylpropyl)aminoethyl, N—[CH(CH3)2]-N-(2-methylpropyl)aminoethyl, N—[C(CH3)3]-N—[CH(CH3)2]aminoethyl, N-butyl-N-(1-methylpropyl)aminoethyl, N-butyl-N-(2-methylpropyl)aminoethyl, N-butyl-N—[C(CH3)3]aminoethyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminoethyl, N—[C(CH3)3]-N-(1-methylpropyl)aminoethyl or N—[C(CH3)3]-N-(2-methylpropyl)aminoethyl;
        aminocarbonyl-C1-C4-alkyl: for example CH2CONH2, 1-(CONH2)ethyl, 2-(CONH2)ethyl, 1-(CONH2)prop-1-yl, 2-(CONH2)prop-1-yl, 3-(CONH2)prop-1-yl, 1-(CONH2)but-1-yl, 2-(CONH2)but-1-yl, 3-(CONH2)but-1-yl, 4-(CONH2)but-1-yl, 1-(CONH2)but-2-yl, 2-(CONH2)but-2-yl, 3-(CONH2)but-2-yl, 4-(CONH2)but-2-yl, 1-(CH2CONH2)eth-1-yl, 1-(CH2CONH2)-1-(CH3)-eth-1-yl or 1-(CH2CONH2)prop-1-yl;
        (C1-C4-alkylamino)carbonyl-C1-C4-alkyl: C1-C4-alkyl which is substituted by (C1-C4-alkylamino)carbonyl as mentioned above, i.e., for example, CH2—CO—NH—CH3, CH2—CO—NH—C2H5, CH2—CO—NH—CH2—C2H5, CH2—CO—NH—CH(CH3)2, CH2—CO—NH—CH2CH2—C2H5, CH2—CO—NH—CH(CH3)—C2H5, CH2—CO—NH—CH2—CH(CH3)2, CH2—CO—NH—C(CH3)3, CH(CH3)—CO—NH—CH3, CH(CH3)—CO—NH—C2H5, 2-(CO—NH—CH3)ethyl, 2-(CO—NH—C2H5)ethyl, 2-(CO—NH—CH2—C2H5)ethyl, 2-[CH2—CO—NH—CH(CH3)2]ethyl, 2-(CO—NH—CH2CH2—C2H5)ethyl, 2-[CO—NH—CH(CH3)—C2H5]ethyl, 2-[CO—NH—CH2—CH(CH3)2]ethyl, 2-[CO—NH—C(CH3)3]ethyl, 2-(CO—NH—CH3)propyl, 2-(CO—NH—C2H5)propyl, 2-(CO—NH—CH2—C2H5)propyl, 2-[CH2—CO—NH—CH(CH3)2]propyl, 2-(CO—NH—CH2CH2—C2H5)propyl, 2-[CO—NH—CH(CH3)—C2H5]propyl, 2-[CO—NH—CH2—CH(CH3)2]propyl, 2-[CO—NH—C(CH3)3]propyl, 3-(CO—NR—CH3)propyl, 3-(CO—NH—C2H5)propyl, 3-(CO—NH—CH2—C2H5)propyl, 3-[CH2—CO—NH—CH(CH3)2]propyl, 3-(CO—NH—CH2CH2—C2H5)propyl, 3-[CO—NH—CH(CH3)—C2H5]propyl, 3-[CO—NH—CH2—CH(CH3)2]Propyl 3-[CO—NH—C(CH3)3]propyl, 2-(CO—NH—CH3)butyl, 2-(CO—NH—C2H5)butyl, 2-(CO—NH—CH2—C2H5)butyl, 2-[CH2—CO—NH—CH(CH3)2]butyl, 2-(CO—NH—CH2CH2—C2H5)butyl, 2-[CO—NH—CH(CH3)—C2H5]butyl, 2-[CO—NH—CH2—CH(CH3)2]butyl, 2-[CO—NH—C(CH3)3]butyl, 3-(CO—NH—CH3)butyl, 3-(CO—NH—C2H5)butyl, 3-(CO—NH—CH2—C2H5)butyl, 3-[CH2—CO—NH—CH(CH3)2]butyl, 3-(CO—NH—CH2CH2—C2H5)butyl, 3-[CO—NH—CH(CH3)—C2H5]butyl, 3-[CO—NH—CH2—CH(CH3)2]butyl, 3-[CO—NH—C(CH3)3]butyl, 4-(CO—NH—CH3)butyl, 4-(CO—NH—C2H5)butyl, 4-(CO—NH—CH2—C2H5)butyl, 4-[CH2—CO—NH—CH(CH3)2]butyl, 4-(CO—NH—CH2CH2—C2H5)butyl, 4-[CO—NH—CH(CH3)—C2H5]butyl, 4-[CO—NH—CH2—CH(CH3)2]butyl or 4-[CO—NH—C(CH3)3]butyl,
        di(C1-C4-alkyl)aminocarbonyl-C1-C4-alkyl: C1-C4-alkyl which is substituted by di(C1-C4-alkyl)aminocarbonyl as mentioned above, i.e., for example, di(C1-C4-alkyl)aminocarbonylmethyl, 1- or 2-di(C1-C4-alkyl)aminocarbonylethyl, 1-, 2- or 3-di(C1-C4-alkyl)aminocarbonylpropyl;
        C1-C4-alkylphenyl: phenyl which is substituted by C1-C4-alkyl as mentioned above, i.e., for example, 2-tolyl, 3-tolyl, 4-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2-(n-propyl)phenyl, 3-(n-propyl)phenyl, 4-(n-propyl)phenyl, 2-(1-methylethyl)phenyl, 3-(1-methylethyl)phenyl, 4-(1-methylethyl)phenyl, 2-(n-butyl)phenyl, 3-(n-butyl)phenyl, 4-(n-butyl)phenyl, 2-(1-methylpropyl)phenyl, 3-(1-methylpropyl)phenyl, 4-(1-methylpropyl)phenyl, 2-(2-methylpropyl)phenyl, 3-(2-methylpropyl)phenyl, 4-(2-methylpropyl)phenyl, 2-(1,1-dimethylethyl)phenyl, 3-(1,1-dimethylethyl)phenyl, 4-(1,1-dimethylethyl)phenyl;
        C3-C6-alkenyl: a monounsaturated aliphatic hydrocarbon radical having 3 to 6 carbon atoms which is preferably not attached via an olefinic carbon atom, for example prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-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, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1-methylbut-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-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-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-methylpent-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-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-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-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl;
        C3-C6-alkynyl: an aliphatic hydrocarbon radical which contains a triple bond and 3 to 6 carbon atoms and which is preferably not attached via a carbon atom of the triple bond, for example propargyl (2-propynyl), 1-propynyl, but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl.
    
    


With respect to the use of the compounds of the formula I according to the invention as herbicides or as compounds with desiccant/defoliant action, the variables X, R2 to R6 are preferably as defined below, in each case independently of one another and in particular in combination:

    X is oxygen,
    R2 is hydrogen, fluorine or chlorine,
    R3 is chlorine or cyano, in particular chlorine,
    R4, R5 independently of one another are hydrogen or C1-C4-alkyl, in particular hydrogen or methyl,
    R6 is hydrogen or C1-C4-alkyl, in particular hydrogen or methyl.


In a preferred embodiment of the invention, R4 or R5 is hydrogen and the other radical R4 or R5 is C1-C4-alkyl, in particular methyl or R4, R5 are each methyl.
Very particular preference is given to compounds of the formula I where
R2 is hydrogen, chlorine or fluorine,
R3 is chlorine or cyano,
R6 is hydrogen and
X is oxygen.
Particular emphasis is given to the following embodiments of the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I:

    1. In a particularly preferred embodiment, R1 in formula I is a heterocyclic radical of the formula II-A. Hereinbelow, such compounds are also referred to as compounds I-A. In the compounds I-A, X and R2 to R8 preferably and in particular have the meanings mentioned as being preferred and particularly preferred, respectively. In particular, in formula II-A,
    
        R10 is C1-C4-alkyl or amino, in particular methyl or amino,
        R11 is C1-C4-haloalkyl, in particular trifluoromethyl, and
        R12 is hydrogen.
    
    
    2. In a further preferred embodiment, R1 in formula I is a heterocyclic radical of the formula II-B. Hereinbelow, such compounds are also referred to as compounds I-B. In the compounds I-B, X and R2 to R8 preferably and in particular have the meanings given as being preferred and particularly preferred, respectively. In particular, in formula. II-B. R13, R13′ are each independently of one another C1-C4-alkyl, in particular methyl.
    3. In a further preferred embodiment, R1 in formula I is a heterocyclic radical of the formula II-C. Hereinbelow, such compounds are also referred to as compounds I-C. In the compounds I-C, X and R2 to R8 preferably and in particular have the meanings given as being preferred and particularly preferred, respectively. In particular, in formula II-C,
    
        R14 is fluorine or chlorine, in particular chlorine,
        R15 is hydrogen or C1-C4-alkyl, in particular hydrogen,
        R16 is C1-C4-haloalkyl, C1-C4-alkylsulfonyl or C1-C4-alkylsulfonyloxy, in particular trifluoromethyl, methylsulfonyl or methylsulfonyloxy.
    
    
    4. In a further preferred embodiment, R1 in formula I is a heterocyclic radical of the formula II-D. Hereinbelow, such compounds are also referred to as compounds I-D. In the compounds I-D, X and R2 to R8 preferably and in particular have the meanings given as being preferred and particularly preferred, respectively. In particular, in formula II-D,
    
        R18 is hydrogen, methyl or amino,
        R19 is C1-C4-haloalkyl or C1-C4-alkylsulfonyl, in particular trifluoromethyl or methylsulfonyl,
        R20 is hydrogen.
    
    
    5. In a further preferred embodiment, R1 in formula I is a heterocyclic radical of the formula II-E. Hereinbelow, such compounds are also referred to as compounds I-E. In the compounds I-E, X and R2 to R8 preferably and in particular have the meanings given as being preferred and particularly preferred, respectively. In particular, in formula II-E,
    
        R21 is halogen or C1-C4-alkyl, in particular chlorine or bromine,
        R22 is C1-C4-haloalkyl, C1-C4-haloalkoxy or C1-C4-alkylsulfonyl, in particular trifluoromethyl, difluoromethyloxy or methylsulfonyl,
        R23 is C1-C4-alkyl, in particular methyl.
    
    
    6. In a further preferred embodiment, R1 in formula I is a heterocyclic radical of the formula II-F. Hereinbelow, such compounds are also referred to as compounds I-F. In the compounds I-F, X and R2 to R8 preferably and in particular have those meanings which have been mentioned as being preferred and particularly preferred, respectively. In particular in formula II-F,
    
        R24 is hydrogen, methyl, difluoromethyl or trifluoromethyl,
        R25 is methyl or trifluoromethyl,
        
            or
        
        
        R24 and R25 together are a chain of the formula —(CH2)4—.
    
    
    7. In a further preferred embodiment, R1 in formula I is a heterocyclic radical of the formula II-G. Hereinbelow, such compounds are also referred to as compounds I-G. In the compounds I-G, X and R2 to R8 preferably and in particular have the meanings given as being preferred and particularly preferred, respectively. In particular, in formula II-G, A1, A2 are each oxygen.
    8. In a further preferred embodiment, R1 in formula I is a heterocyclic radical of the formula II-H. Hereinbelow, such compounds are also referred to as compounds I-H. In the compounds I-H, X and R2 to R8 preferably and in particular have those meanings which have been mentioned as preferred and particularly preferred, respectively. In particular, in formula II-H,
    
        A3, A4 are as defined above and are preferably each oxygen,
        R26, R27 are each independently of one another C1-C4-alkyl or C1-C4-haloalkyl, in particular methyl or difluoromethyl or trifluoromethyl, or
        R26 and R27 together are a chain of the formula —CH2—O—(CH2)2— or —(CH2)4—.
    
    


Very particular preference is given to the compounds of the formula I, where
R1 is II-A where R10=CH3 or amino, R11=CF3 and


    
    
        R12=hydrogen,

R2 is hydrogen or fluorine,

R3 is chlorine or cyano,

R6 is hydrogen and

X is oxygen.

    
    


Very particular preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Aa (≡I where R1=II-A, R10=methyl, R11=trifluoromethyl and R12=hydrogen, R2=F, R3=Cl, R6=H, X=O), where R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Aa.1 to I-Aa.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.















TABLE 1





No.
R4
R5
R7
R8



















1
H
H
H
H


2
H
H
H
CH3


3
H
H
H
CH2CH3


4
H
H
H
CH2CH2CH3


5
H
H
H
CH2CH2CH2CH3


6
H
H
H
CH(CH3)2


7
H
H
H
CH2CH(CH3)2


8
H
H
H
CH(CH3)CH2CH3


9
H
H
H
C(CH3)3


10
H
H
H
CH2OCH3


11
H
H
H
CH2CH2OCH3


12
H
H
H
CH2OCH2CH3


13
H
H
H
CH2CH2OCH2CH3


14
H
H
H
CH(CH3)CH2OCH3


15
H
H
H
CH2CH2Cl


16
H
H
H
CH2CH2SCH3


17
H
H
H
CH2CH2S(O)CH3


18
H
H
H
CH2CH2S(O)2CH3


19
H
H
H
CH2CH2CN


20
H
H
H
CH2CH2CO2CH3


21
H
H
H
CH2CH2CO2CH2CH3


22
H
H
H
CH2CH2NH2


23
H
H
H
CH2CH2N(CH3)2


24
H
H
H
CH2CH2N(CH2CH3)2


25
H
H
H
CH2CH═CH2


26
H
H
H
C(CH3)═CH2


27
H
H
H
CH2CH═CHCH3


28
H
H
H
C(CH3)CH═CHCH3


29
H
H
H
CH2C≡CH


30
H
H
H
CH(CH3)C≡CH


31
H
H
H
CH2C≡CHCH3


32
H
H
H
Ph










33
H
H
—(CH2)4—


34
H
H
—(CH2)5—


35
H
H
—(CH2)2NH(CH2)2—


36
H
H
—(CH2)2NCH3(CH2)2—


37
H
H
—(CH2)2O(CH2)2—


38
H
H
—CH2CH═CHCH2—


39
H
H
—CH2CH═CHCH2CH2—


40
H
H
—CH═CHCH2CH2CH2—











41
H
H
CH3
H


42
H
H
CH3
CH3


43
H
H
CH3
CH2CH3


44
H
H
CH3
CH2CH2CH3


45
H
H
CH3
CH2CH2CH2CH3


46
H
H
CH3
CH(CH3)2


47
H
H
CH3
CH2CH(CH3)2


48
H
H
CH3
CH(CH3)CH2CH3


49
H
H
CH3
C(CH3)3


50
H
H
CH3
CH2OCH3


51
H
H
CH3
CH2CH2OCH3


52
H
H
CH3
CH2OCH2CH3


53
H
H
CH3
CH2CH2OCH2CH3


54
H
H
CH3
CH(CH3)CH2OCH3


55
H
H
CH3
CH2CH2Cl


56
H
H
CH3
CH2CH2SCH3


57
H
H
CH3
CH2CH2S(O)CH3


58
H
H
CH3
CH2CH2S(O)2CH3


59
H
H
CH3
CH2CH2CN


60
H
H
CH3
CH2CH2CO2CH3


61
H
H
CH3
CH2CH2CO2CH2CH3


62
H
H
CH3
CH2CH2NH2


63
H
H
CH3
CH2CH2N(CH3)2


64
H
H
CH3
CH2CH2N(CH2CH3)2


65
H
H
CH3
CH2CH═CH2


66
H
H
CH3
C(CH3)═CH2


67
H
H
CH3
CH2CH═CHCH3


68
H
H
CH3
C(CH3)CH═CHCH3


69
H
H
CH3
CH2C≡CH


70
H
H
CH3
CH(CH3)C≡CH


71
H
H
CH3
CH2C≡CHCH3


72
H
H
CH3
Ph


73
H
H
CH2CH3
H


74
H
H
CH2CH3
CH3


75
H
H
CH2CH3
CH2CH3


76
H
H
CH2CH3
CH2CH2CH3


77
H
H
CH2CH3
CH2CH2CH2CH3


78
H
H
CH2CH3
CH(CH3)2


79
H
H
CH2CH3
CH2CH(CH3)2


80
H
H
CH2CH3
CH(CH3)CH2CH3


81
H
H
CH2CH3
C(CH3)3


82
H
H
CH2CH3
CH2OCH3


83
H
H
CH2CH3
CH2CH2OCH3


84
H
H
CH2CH3
CH2OCH2CH3


85
H
H
CH2CH3
CH2CH2OCH2CH3


86
H
H
CH2CH3
CH(CH3)CH2OCH3


87
H
H
CH2CH3
CH2CH2Cl


88
H
H
CH2CH3
CH2CH2SCH3


89
H
H
CH2CH3
CH2CH2S(O)CH3


90
H
H
CH2CH3
CH2CH2S(O)2CH3


91
H
H
CH2CH3
CH2CH2CN


92
H
H
CH2CH3
CH2CH2CO2CH3


93
H
H
CH2CH3
CH2CH2CO2CH2CH3


94
H
H
CH2CH3
CH2CH2NH2


95
H
H
CH2CH3
CH2CH2N(CH3)2


96
H
H
CH2CH3
CH2CH2N(CH2CH3)2


97
H
H
CH2CH3
CH2CH═CH2


98
H
H
CH2CH3
C(CH3)═CH2


99
H
H
CH2CH3
CH2CH═CHCH3


100
H
H
CH2CH3
C(CH3)CH═CHCH3


101
H
H
CH2CH3
CH2C≡CH


102
H
H
CH2CH3
CH(CH3)C≡CH


103
H
H
CH2CH3
CH2C≡CHCH3


104
H
H
CH2CH3
Ph


105
H
H
CH2CH2CH3
H


106
H
H
CH2CH2CH3
CH3


107
H
H
CH2CH2CH3
CH2CH3


108
H
H
CH2CH2CH3
CH2CH2CH3


109
H
H
CH2CH2CH3
CH2CH2CH2CH3


110
H
H
CH2CH2CH3
CH(CH3)2


111
H
H
CH2CH2CH3
CH2CH(CH3)2


112
H
H
CH2CH2CH3
CH(CH3)CH2CH3


113
H
H
CH2CH2CH3
C(CH3)3


114
H
H
CH2CH2CH3
CH2OCH3


115
H
H
CH2CH2CH3
CH2CH2OCH3


116
H
H
CH2CH2CH3
CH2OCH2CH3


117
H
H
CH2CH2CH3
CH2CH2OCH2CH3


118
H
H
CH2CH2CH3
CH(CH3)CH2OCH3


119
H
H
CH2CH2CH3
CH2CH2Cl


120
H
H
CH2CH2CH3
CH2CH2SCH3


121
H
H
CH2CH2CH3
CH2CH2S(O)CH3


122
H
H
CH2CH2CH3
CH2CH2S(O)2CH3


123
H
H
CH2CH2CH3
CH2CH2CN


124
H
H
CH2CH2CH3
CH2CH2CO2CH3


125
H
H
CH2CH2CH3
CH2CH2CO2CH2CH3


126
H
H
CH2CH2CH3
CH2CH2NH2


127
H
H
CH2CH2CH3
CH2CH2N(CH3)2


128
H
H
CH2CH2CH3
CH2CH2N(CH2CH3)2


129
H
H
CH2CH2CH3
CH2CH═CH2


130
H
H
CH2CH2CH3
C(CH3)═CH2


131
H
H
CH2CH2CH3
CH2CH═CHCH3


132
H
H
CH2CH2CH3
C(CH3)CH═CHCH3


133
H
H
CH2CH2CH3
CH2C≡CH


134
H
H
CH2CH2CH3
CH(CH3)C≡CH


135
H
H
CH2CH2CH3
CH2C≡CHCH3


136
H
H
CH2CH2CH3
Ph


137
H
H
CH(CH3)2
H


138
H
H
CH(CH3)2
CH3


139
H
H
CH(CH3)2
CH2CH3


140
H
H
CH(CH3)2
CH2CH2CH3


141
H
H
CH(CH3)2
CH2CH2CH2CH3


142
H
H
CH(CH3)2
CH(CH3)2


143
H
H
CH(CH3)2
CH2CH(CH3)2


144
H
H
CH(CH3)2
CH(CH3)CH2CH3


145
H
H
CH(CH3)2
C(CH3)3


146
H
H
CH(CH3)2
CH2OCH3


147
H
H
CH(CH3)2
CH2CH2OCH3


148
H
H
CH(CH3)2
CH2OCH2CH3


149
H
H
CH(CH3)2
CH2CH2OCH2CH3


150
H
H
CH(CH3)2
CH(CH3)CH2OCH3


151
H
H
CH(CH3)2
CH2CH2Cl


152
H
H
CH(CH3)2
CH2CH2SCH3


153
H
H
CH(CH3)2
CH2CH2S(O)CH3


154
H
H
CH(CH3)2
CH2CH2S(O)2CH3


155
H
H
CH(CH3)2
CH2CH2CN


156
H
H
CH(CH3)2
CH2CH2CO2CH3


157
H
H
CH(CH3)2
CH2CH2CO2CH2CH3


158
H
H
CH(CH3)2
CH2CH2NH2


159
H
H
CH(CH3)2
CH2CH2N(CH3)2


160
H
H
CH(CH3)2
CH2CH2N(CH2CH3)2


161
H
H
CH(CH3)2
CH2CH═CH2


162
H
H
CH(CH3)2
C(CH3)═CH2


163
H
H
CH(CH3)2
CH2CH═CHCH3


164
H
H
CH(CH3)2
C(CH3)CH═CHCH3


165
H
H
CH(CH3)2
CH2C≡CH


166
H
H
CH(CH3)2
CH(CH3)C≡CH


167
H
H
CH(CH3)2
CH2C≡CHCH3


168
H
H
CH(CH3)2
Ph


169
H
H
CH2CH═CH2
H


170
H
H
CH2CH═CH2
CH3


171
H
H
CH2CH═CH2
CH2CH3


172
H
H
CH2CH═CH2
CH2CH2CH3


173
H
H
CH2CH═CH2
CH2CH2CH2CH3


174
H
H
CH2CH═CH2
CH(CH3)2


175
H
H
CH2CH═CH2
CH2CH(CH3)2


176
H
H
CH2CH═CH2
CH(CH3)CH2CH3


177
H
H
CH2CH═CH2
C(CH3)3


178
H
H
CH2CH═CH2
CH2OCH3


179
H
H
CH2CH═CH2
CH2CH2OCH3


180
H
H
CH2CH═CH2
CH2OCH2CH3


181
H
H
CH2CH═CH2
CH2CH2OCH2CH3


182
H
H
CH2CH═CH2
CH(CH3)CH2OCH3


183
H
H
CH2CH═CH2
CH2CH2Cl


184
H
H
CH2CH═CH2
CH2CH2SCH3


185
H
H
CH2CH═CH2
CH2CH2S(O)CH3


186
H
H
CH2CH═CH2
CH2CH2S(O)2CH3


187
H
H
CH2CH═CH2
CH2CH2CN


188
H
H
CH2CH═CH2
CH2CH2CO2CH3


189
H
H
CH2CH═CH2
CH2CH2CO2CH2CH3


190
H
H
CH2CH═CH2
CH2CH2NH2


191
H
H
CH2CH═CH2
CH2CH2N(CH3)2


192
H
H
CH2CH═CH2
CH2CH2N(CH2CH3)2


193
H
H
CH2CH═CH2
CH2CH═CH2


194
H
H
CH2CH═CH2
C(CH3)═CH2


195
H
H
CH2CH═CH2
CH2CH═CHCH3


196
H
H
CH2CH═CH2
C(CH3)CH═CHCH3


197
H
H
CH2CH═CH2
CH2C≡CH


198
H
H
CH2CH═CH2
CH(CH3)C≡CH


199
H
H
CH2CH═CH2
CH2C≡CHCH3


200
H
H
CH2CH═CH2
Ph


201
CH3
H
H
H


202
CH3
H
H
CH3


203
CH3
H
H
CH2CH3


204
CH3
H
H
CH2CH2CH3


205
CH3
H
H
CH2CH2CH2CH3


206
CH3
H
H
CH(CH3)2


207
CH3
H
H
CH2CH(CH3)2


208
CH3
H
H
CH(CH3)CH2CH3


209
CH3
H
H
C(CH3)3


210
CH3
H
H
CH2OCH3


211
CH3
H
H
CH2CH2OCH3


212
CH3
H
H
CH2OCH2CH3


213
CH3
H
H
CH2CH2OCH2CH3


214
CH3
H
H
CH(CH3)CH2OCH3


215
CH3
H
H
CH2CH2Cl


216
CH3
H
H
CH2CH2SCH3


217
CH3
H
H
CH2CH2S(O)CH3


218
CH3
H
H
CH2CH2S(O)2CH3


219
CH3
H
H
CH2CH2CN


220
CH3
H
H
CH2CH2CO2CH3


221
CH3
H
H
CH2CH2CO2CH2CH3


222
CH3
H
H
CH2CH2NH2


223
CH3
H
H
CH2CH2N(CH3)2


224
CH3
H
H
CH2CH2N(CH2CH3)2


225
CH3
H
H
CH2CH═CH2


226
CH3
H
H
C(CH3)═CH2


227
CH3
H
H
CH2CH═CHCH3


228
CH3
H
H
C(CH3)CH═CHCH3


229
CH3
H
H
CH2C≡CH


230
CH3
H
H
CH(CH3)C≡CH


231
CH3
H
H
CH2C≡CHCH3


232
CH3
H
H
Ph










233
CH3
H
—(CH2)4—


234
CH3
H
—(CH2)5—


235
CH3
H
—(CH2)2NH(CH2)2—


236
CH3
H
—(CH2)2NCH3(CH2)2—


237
CH3
H
—(CH2)2O(CH2)2—


238
CH3
H
—CH2CH═CHCH2—


239
CH3
H
—CH2CH═CHCH2CH2—


240
CH3
H
—CH═CHCH2CH2CH2—











241
CH3
H
CH3
H


242
CH3
H
CH3
CH3


243
CH3
H
CH3
CH2CH3


244
CH3
H
CH3
CH2CH2CH3


245
CH3
H
CH3
CH2CH2CH2CH3


246
CH3
H
CH3
CH(CH3)2


247
CH3
H
CH3
CH2CH(CH3)2


248
CH3
H
CH3
CH(CH3)CH2CH3


249
CH3
H
CH3
C(CH3)3


250
CH3
H
CH3
CH2OCH3


251
CH3
H
CH3
CH2CH2OCH3


252
CH3
H
CH3
CH2OCH2CH3


253
CH3
H
CH3
CH2CH2OCH2CH3


254
CH3
H
CH3
CH(CH3)CH2OCH3


255
CH3
H
CH3
CH2CH2Cl


256
CH3
H
CH3
CH2CH2SCH3


257
CH3
H
CH3
CH2CH2S(O)CH3


258
CH3
H
CH3
CH2CH2S(O)2CH3


259
CH3
H
CH3
CH2CH2CN


260
CH3
H
CH3
CH2CH2CO2CH3


261
CH3
H
CH3
CH2CH2CO2CH2CH3


262
CH3
H
CH3
CH2CH2NH2


263
CH3
H
CH3
CH2CH2N(CH3)2


264
CH3
H
CH3
CH2CH2N(CH2CH3)2


265
CH3
H
CH3
CH2CH═CH2


266
CH3
H
CH3
C(CH3)═CH2


267
CH3
H
CH3
CH2CH═CHCH3


268
CH3
H
CH3
C(CH3)CH═CHCH3


269
CH3
H
CH3
CH2C≡CH


270
CH3
H
CH3
CH(CH3)C≡CH


271
CH3
H
CH3
CH2C≡CHCH3


272
CH3
H
CH3
Ph


273
CH3
H
CH2CH3
H


274
CH3
H
CH2CH3
CH3


275
CH3
H
CH2CH3
CH2CH3


276
CH3
H
CH2CH3
CH2CH2CH3


277
CH3
H
CH2CH3
CH2CH2CH2CH3


278
CH3
H
CH2CH3
CH(CH3)2


279
CH3
H
CH2CH3
CH2CH(CH3)2


280
CH3
H
CH2CH3
CH(CH3)CH2CH3


281
CH3
H
CH2CH3
C(CH3)3


282
CH3
H
CH2CH3
CH2OCH3


283
CH3
H
CH2CH3
CH2CH2OCH3


284
CH3
H
CH2CH3
CH2OCH2CH3


285
CH3
H
CH2CH3
CH2CH2OCH2CH3


286
CH3
H
CH2CH3
CH(CH3)CH2OCH3


287
CH3
H
CH2CH3
CH2CH2Cl


288
CH3
H
CH2CH3
CH2CH2SCH3


289
CH3
H
CH2CH3
CH2CH2S(O)CH3


290
CH3
H
CH2CH3
CH2CH2S(O)2CH3


291
CH3
H
CH2CH3
CH2CH2CN


292
CH3
H
CH2CH3
CH2CH2CO2CH3


293
CH3
H
CH2CH3
CH2CH2CO2CH2CH3


294
CH3
H
CH2CH3
CH2CH2NH2


295
CH3
H
CH2CH3
CH2CH2N(CH3)2


296
CH3
H
CH2CH3
CH2CH2N(CH2CH3)2


297
CH3
H
CH2CH3
CH2CH═CH2


298
CH3
H
CH2CH3
C(CH3)═CH2


299
CH3
H
CH2CH3
CH2CH═CHCH3


300
CH3
H
CH2CH3
C(CH3)CH═CHCH3


301
CH3
H
CH2CH3
CH2C≡CH


302
CH3
H
CH2CH3
CH(CH3)C≡CH


303
CH3
H
CH2CH3
CH2C≡CHCH3


304
CH3
H
CH2CH3
Ph


305
CH3
H
CH2CH2CH3
H


306
CH3
H
CH2CH2CH3
CH3


307
CH3
H
CH2CH2CH3
CH2CH3


308
CH3
H
CH2CH2CH3
CH2CH2CH3


309
CH3
H
CH2CH2CH3
CH2CH2CH2CH3


310
CH3
H
CH2CH2CH3
CH(CH3)2


311
CH3
H
CH2CH2CH3
CH2CH(CH3)2


312
CH3
H
CH2CH2CH3
CH(CH3)CH2CH3


313
CH3
H
CH2CH2CH3
C(CH3)3


314
CH3
H
CH2CH2CH3
CH2OCH3


315
CH3
H
CH2CH2CH3
CH2CH2OCH3


316
CH3
H
CH2CH2CH3
CH2OCH2CH3


317
CH3
H
CH2CH2CH3
CH2CH2OCH2CH3


318
CH3
H
CH2CH2CH3
CH(CH3)CH2OCH3


319
CH3
H
CH2CH2CH3
CH2CH2Cl


320
CH3
H
CH2CH2CH3
CH2CH2SCH3


321
CH3
H
CH2CH2CH3
CH2CH2S(O)CH3


322
CH3
H
CH2CH2CH3
CH2CH2S(O)2CH3


323
CH3
H
CH2CH2CH3
CH2CH2CN


324
CH3
H
CH2CH2CH3
CH2CH2CO2CH3


325
CH3
H
CH2CH2CH3
CH2CH2CO2CH2CH3


326
CH3
H
CH2CH2CH3
CH2CH2NH2


327
CH3
H
CH2CH2CH3
CH2CH2N(CH3)2


328
CH3
H
CH2CH2CH3
CH2CH2N(CH2CH3)2


329
CH3
H
CH2CH2CH3
CH2CH═CH2


330
CH3
H
CH2CH2CH3
C(CH3)═CH2


331
CH3
H
CH2CH2CH3
CH2CH═CHCH3


332
CH3
H
CH2CH2CH3
C(CH3)CH═CHCH3


333
CH3
H
CH2CH2CH3
CH2C≡CH


334
CH3
H
CH2CH2CH3
CH(CH3)C≡CH


335
CH3
H
CH2CH2CH3
CH2C≡CHCH3


336
CH3
H
CH2CH2CH3
Ph


337
CH3
H
CH(CH3)2
H


338
CH3
H
CH(CH3)2
CH3


339
CH3
H
CH(CH3)2
CH2CH3


340
CH3
H
CH(CH3)2
CH2CH2CH3


341
CH3
H
CH(CH3)2
CH2CH2CH2CH3


342
CH3
H
CH(CH3)2
CH(CH3)2


343
CH3
H
CH(CH3)2
CH2CH(CH3)2


344
CH3
H
CH(CH3)2
CH(CH3)CH2CH3


345
CH3
H
CH(CH3)2
C(CH3)3


346
CH3
H
CH(CH3)2
CH2OCH3


347
CH3
H
CH(CH3)2
CH2CH2OCH3


348
CH3
H
CH(CH3)2
CH2OCH2CH3


349
CH3
H
CH(CH3)2
CH2CH2OCH2CH3


350
CH3
H
CH(CH3)2
CH(CH3)CH2OCH3


351
CH3
H
CH(CH3)2
CH2CH2Cl


352
CH3
H
CH(CH3)2
CH2CH2SCH3


353
CH3
H
CH(CH3)2
CH2CH2S(O)CH3


354
CH3
H
CH(CH3)2
CH2CH2S(O)2CH3


355
CH3
H
CH(CH3)2
CH2CH2CN


356
CH3
H
CH(CH3)2
CH2CH2CO2CH3


357
CH3
H
CH(CH3)2
CH2CH2CO2CH2CH3


358
CH3
H
CH(CH3)2
CH2CH2NH2


359
CH3
H
CH(CH3)2
CH2CH2N(CH3)2


360
CH3
H
CH(CH3)2
CH2CH2N(CH2CH3)2


361
CH3
H
CH(CH3)2
CH2CH═CH2


362
CH3
H
CH(CH3)2
C(CH3)═CH2


363
CH3
H
CH(CH3)2
CH2CH═CHCH3


364
CH3
H
CH(CH3)2
C(CH3)CH═CHCH3


365
CH3
H
CH(CH3)2
CH2C≡CH


366
CH3
H
CH(CH3)2
CH(CH3)C≡CH


367
CH3
H
CH(CH3)2
CH2C≡CHCH3


368
CH3
H
CH(CH3)2
Ph


369
CH3
H
CH2CH═CH2
H


370
CH3
H
CH2CH═CH2
CH3


371
CH3
H
CH2CH═CH2
CH2CH3


372
CH3
H
CH2CH═CH2
CH2CH2CH3


373
CH3
H
CH2CH═CH2
CH2CH2CH2CH3


374
CH3
H
CH2CH═CH2
CH(CH3)2


375
CH3
H
CH2CH═CH2
CH2CH(CH3)2


376
CH3
H
CH2CH═CH2
CH(CH3)CH2CH3


377
CH3
H
CH2CH═CH2
C(CH3)3


378
CH3
H
CH2CH═CH2
CH2OCH3


379
CH3
H
CH2CH═CH2
CH2CH2OCH3


380
CH3
H
CH2CH═CH2
CH2OCH2CH3


381
CH3
H
CH2CH═CH2
CH2CH2OCH2CH3


382
CH3
H
CH2CH═CH2
CH(CH3)CH2OCH3


383
CH3
H
CH2CH═CH2
CH2CH2Cl


384
CH3
H
CH2CH═CH2
CH2CH2SCH3


385
CH3
H
CH2CH═CH2
CH2CH2S(O)CH3


386
CH3
H
CH2CH═CH2
CH2CH2S(O)2CH3


387
CH3
H
CH2CH═CH2
CH2CH2CN


388
CH3
H
CH2CH═CH2
CH2CH2CO2CH3


389
CH3
H
CH2CH═CH2
CH2CH2CO2CH2CH3


390
CH3
H
CH2CH═CH2
CH2CH2NH2


391
CH3
H
CH2CH═CH2
CH2CH2N(CH3)2


392
CH3
H
CH2CH═CH2
CH2CH2N(CH2CH3)2


393
CH3
H
CH2CH═CH2
CH2CH═CH2


394
CH3
H
CH2CH═CH2
C(CH3)═CH2


395
CH3
H
CH2CH═CH2
CH2CH═CHCH3


396
CH3
H
CH2CH═CH2
C(CH3)CH═CHCH3


397
CH3
H
CH2CH═CH2
CH2C≡CH


398
CH3
H
CH2CH═CH2
CH(CH3)C≡CH


399
CH3
H
CH2CH═CH2
CH2C≡CHCH3


400
CH3
H
CH2CH═CH2
Ph


401
CH3
CH3
H
H


402
CH3
CH3
H
CH3


403
CH3
CH3
H
CH2CH3


404
CH3
CH3
H
CH2CH2CH3


405
CH3
CH3
H
CH2CH2CH2CH3


406
CH3
CH3
H
CH(CH3)2


407
CH3
CH3
H
CH2CH(CH3)2


408
CH3
CH3
H
CH(CH3)CH2CH3


409
CH3
CH3
H
C(CH3)3


410
CH3
CH3
H
CH2OCH3


411
CH3
CH3
H
CH2CH2OCH3


412
CH3
CH3
H
CH2OCH2CH3


413
CH3
CH3
H
CH2CH2OCH2CH3


414
CH3
CH3
H
CH(CH3)CH2OCH3


415
CH3
CH3
H
CH2CH2Cl


416
CH3
CH3
H
CH2CH2SCH3


417
CH3
CH3
H
CH2CH2S(O)CH3


418
CH3
CH3
H
CH2CH2S(O)2CH3


419
CH3
CH3
H
CH2CH2CN


420
CH3
CH3
H
CH2CH2CO2CH3


421
CH3
CH3
H
CH2CH2CO2CH2CH3


422
CH3
CH3
H
CH2CH2NH2


423
CH3
CH3
H
CH2CH2N(CH3)2


424
CH3
CH3
H
CH2CH2N(CH2CH3)2


425
CH3
CH3
H
CH2CH═CH2


426
CH3
CH3
H
C(CH3)═CH2


427
CH3
CH3
H
CH2CH═CHCH3


428
CH3
CH3
H
C(CH3)CH═CHCH3


429
CH3
CH3
H
CH2C≡CH


430
CH3
CH3
H
CH(CH3)C≡CH


431
CH3
CH3
H
CH2C≡CHCH3


432
CH3
CH3
H
Ph










433
CH3
CH3
—(CH2)4—


434
CH3
CH3
—(CH2)5—


435
CH3
CH3
—(CH2)2NH(CH2)2—


436
CH3
CH3
—(CH2)2NCH3(CH2)2—


437
CH3
CH3
—(CH2)2O(CH2)2—


438
CH3
CH3
—CH2CH═CHCH2—


439
CH3
CH3
—CH2CH═CHCH2CH2—


440
CH3
CH3
—CH═CHCH2CH2CH2—











441
CH3
CH3
CH3
H


442
CH3
CH3
CH3
CH3


443
CH3
CH3
CH3
CH2CH3


444
CH3
CH3
CH3
CH2CH2CH3


445
CH3
CH3
CH3
CH2CH2CH2CH3


446
CH3
CH3
CH3
CH(CH3)2


447
CH3
CH3
CH3
CH2CH(CH3)2


448
CH3
CH3
CH3
CH(CH3)CH2CH3


449
CH3
CH3
CH3
C(CH3)3


450
CH3
CH3
CH3
CH2OCH3


451
CH3
CH3
CH3
CH2CH2OCH3


452
CH3
CH3
CH3
CH2OCH2CH3


453
CH3
CH3
CH3
CH2CH2OCH2CH3


454
CH3
CH3
CH3
CH(CH3)CH2OCH3


455
CH3
CH3
CH3
CH2CH2Cl


456
CH3
CH3
CH3
CH2CH2SCH3


457
CH3
CH3
CH3
CH2CH2S(O)CH3


458
CH3
CH3
CH3
CH2CH2S(O)2CH3


459
CH3
CH3
CH3
CH2CH2CN


460
CH3
CH3
CH3
CH2CH2CO2CH3


461
CH3
CH3
CH3
CH2CH2CO2CH2CH3


462
CH3
CH3
CH3
CH2CH2NH2


463
CH3
CH3
CH3
CH2CH2N(CH3)2


464
CH3
CH3
CH3
CH2CH2N(CH2CH3)2


465
CH3
CH3
CH3
CH2CH═CH2


466
CH3
CH3
CH3
C(CH3)═CH2


467
CH3
CH3
CH3
CH2CH═CHCH3


468
CH3
CH3
CH3
C(CH3)CH═CHCH3


469
CH3
CH3
CH3
CH2C≡CH


470
CH3
CH3
CH3
CH(CH3)C≡CH


471
CH3
CH3
CH3
CH2C≡CHCH3


472
CH3
CH3
CH3
Ph


473
CH3
CH3
CH2CH3
H


474
CH3
CH3
CH2CH3
CH3


475
CH3
CH3
CH2CH3
CH2CH3


476
CH3
CH3
CH2CH3
CH2CH2CH3


477
CH3
CH3
CH2CH3
CH2CH2CH2CH3


478
CH3
CH3
CH2CH3
CH(CH3)2


479
CH3
CH3
CH2CH3
CH2CH(CH3)2


480
CH3
CH3
CH2CH3
CH(CH3)CH2CH3


481
CH3
CH3
CH2CH3
C(CH3)3


482
CH3
CH3
CH2CH3
CH2OCH3


483
CH3
CH3
CH2CH3
CH2CH2OCH3


484
CH3
CH3
CH2CH3
CH2OCH2CH3


485
CH3
CH3
CH2CH3
CH2CH2OCH2CH3


486
CH3
CH3
CH2CH3
CH(CH3)CH2OCH3


487
CH3
CH3
CH2CH3
CH2CH2Cl


488
CH3
CH3
CH2CH3
CH2CH2SCH3


489
CH3
CH3
CH2CH3
CH2CH2S(O)CH3


490
CH3
CH3
CH2CH3
CH2CH2S(O)2CH3


491
CH3
CH3
CH2CH3
CH2CH2CN


492
CH3
CH3
CH2CH3
CH2CH2CO2CH3


493
CH3
CH3
CH2CH3
CH2CH2CO2CH2CH3


494
CH3
CH3
CH2CH3
CH2CH2NH2


495
CH3
CH3
CH2CH3
CH2CH2N(CH3)2


496
CH3
CH3
CH2CH3
CH2CH2N(CH2CH3)2


497
CH3
CH3
CH2CH3
CH2CH═CH2


498
CH3
CH3
CH2CH3
C(CH3)═CH2


499
CH3
CH3
CH2CH3
CH2CH═CHCH3


500
CH3
CH3
CH2CH3
C(CH3)CH═CHCH3


501
CH3
CH3
CH2CH3
CH2C≡CH


502
CH3
CH3
CH2CH3
CH(CH3)C≡CH


503
CH3
CH3
CH2CH3
CH2C≡CHCH3


504
CH3
CH3
CH2CH3
Ph


505
CH3
CH3
CH2CH2CH3
H


506
CH3
CH3
CH2CH2CH3
CH3


507
CH3
CH3
CH2CH2CH3
CH2CH3


508
CH3
CH3
CH2CH2CH3
CH2CH2CH3


509
CH3
CH3
CH2CH2CH3
CH2CH2CH2CH3


510
CH3
CH3
CH2CH2CH3
CH(CH3)2


511
CH3
CH3
CH2CH2CH3
CH2CH(CH3)2


512
CH3
CH3
CH2CH2CH3
CH(CH3)CH2CH3


513
CH3
CH3
CH2CH2CH3
C(CH3)3


514
CH3
CH3
CH2CH2CH3
CH2OCH3


515
CH3
CH3
CH2CH2CH3
CH2CH2OCH3


516
CH3
CH3
CH2CH2CH3
CH2OCH2CH3


517
CH3
CH3
CH2CH2CH3
CH2CH2OCH2CH3


518
CH3
CH3
CH2CH2CH3
CH(CH3)CH2OCH3


519
CH3
CH3
CH2CH2CH3
CH2CH2Cl


520
CH3
CH3
CH2CH2CH3
CH2CH2SCH3


521
CH3
CH3
CH2CH2CH3
CH2CH2S(O)CH3


522
CH3
CH3
CH2CH2CH3
CH2CH2S(O)2CH3


523
CH3
CH3
CH2CH2CH3
CH2CH2CN


524
CH3
CH3
CH2CH2CH3
CH2CH2CO2CH3


525
CH3
CH3
CH2CH2CH3
CH2CH2CO2CH2CH3


526
CH3
CH3
CH2CH2CH3
CH2CH2NH2


527
CH3
CH3
CH2CH2CH3
CH2CH2N(CH3)2


528
CH3
CH3
CH2CH2CH3
CH2CH2N(CH2CH3)2


529
CH3
CH3
CH2CH2CH3
CH2CH═CH2


530
CH3
CH3
CH2CH2CH3
C(CH3)═CH2


531
CH3
CH3
CH2CH2CH3
CH2CH═CHCH3


532
CH3
CH3
CH2CH2CH3
C(CH3)CH═CHCH3


533
CH3
CH3
CH2CH2CH3
CH2C≡CH


534
CH3
CH3
CH2CH2CH3
CH(CH3)C≡CH


535
CH3
CH3
CH2CH2CH3
CH2C≡CHCH3


536
CH3
CH3
CH2CH2CH3
Ph


537
CH3
CH3
CH(CH3)2
H


538
CH3
CH3
CH(CH3)2
CH3


539
CH3
CH3
CH(CH3)2
CH2CH3


540
CH3
CH3
CH(CH3)2
CH2CH2CH3


541
CH3
CH3
CH(CH3)2
CH2CH2CH2CH3


542
CH3
CH3
CH(CH3)2
CH(CH3)2


543
CH3
CH3
CH(CH3)2
CH2CH(CH3)2


544
CH3
CH3
CH(CH3)2
CH(CH3)CH2CH3


545
CH3
CH3
CH(CH3)2
C(CH3)3


546
CH3
CH3
CH(CH3)2
CH2OCH3


547
CH3
CH3
CH(CH3)2
CH2CH2OCH3


548
CH3
CH3
CH(CH3)2
CH2OCH2CH3


549
CH3
CH3
CH(CH3)2
CH2CH2OCH2CH3


550
CH3
CH3
CH(CH3)2
CH(CH3)CH2OCH3


551
CH3
CH3
CH(CH3)2
CH2CH2Cl


552
CH3
CH3
CH(CH3)2
CH2CH2SCH3


553
CH3
CH3
CH(CH3)2
CH2CH2S(O)CH3


554
CH3
CH3
CH(CH3)2
CH2CH2S(O)2CH3


555
CH3
CH3
CH(CH3)2
CH2CH2CN


556
CH3
CH3
CH(CH3)2
CH2CH2CO2CH3


557
CH3
CH3
CH(CH3)2
CH2CH2CO2CH2CH3


558
CH3
CH3
CH(CH3)2
CH2CH2NH2


559
CH3
CH3
CH(CH3)2
CH2CH2N(CH3)2


560
CH3
CH3
CH(CH3)2
CH2CH2N(CH2CH3)2


561
CH3
CH3
CH(CH3)2
CH2CH═CH2


562
CH3
CH3
CH(CH3)2
C(CH3)═CH2


563
CH3
CH3
CH(CH3)2
CH2CH═CHCH3


564
CH3
CH3
CH(CH3)2
C(CH3)CH═CHCH3


565
CH3
CH3
CH(CH3)2
CH2C≡CH


566
CH3
CH3
CH(CH3)2
CH(CH3)C≡CH


567
CH3
CH3
CH(CH3)2
CH2C≡CHCH3


568
CH3
CH3
CH(CH3)2
Ph


569
CH3
CH3
CH2CH═CH2
H


570
CH3
CH3
CH2CH═CH2
CH3


571
CH3
CH3
CH2CH═CH2
CH2CH3


572
CH3
CH3
CH2CH═CH2
CH2CH2CH3


573
CH3
CH3
CH2CH═CH2
CH2CH2CH2CH3


574
CH3
CH3
CH2CH═CH2
CH(CH3)2


575
CH3
CH3
CH2CH═CH2
CH2CH(CH3)2


576
CH3
CH3
CH2CH═CH2
CH(CH3)CH2CH3


577
CH3
CH3
CH2CH═CH2
C(CH3)3


578
CH3
CH3
CH2CH═CH2
CH2OCH3


579
CH3
CH3
CH2CH═CH2
CH2CH2OCH3


580
CH3
CH3
CH2CH═CH2
CH2OCH2CH3


581
CH3
CH3
CH2CH═CH2
CH2CH2OCH2CH3


582
CH3
CH3
CH2CH═CH2
CH(CH3)CH2OCH3


583
CH3
CH3
CH2CH═CH2
CH2CH2Cl


584
CH3
CH3
CH2CH═CH2
CH2CH2SCH3


585
CH3
CH3
CH2CH═CH2
CH2CH2S(O)CH3


586
CH3
CH3
CH2CH═CH2
CH2CH2S(O)2CH3


587
CH3
CH3
CH2CH═CH2
CH2CH2CN


588
CH3
CH3
CH2CH═CH2
CH2CH2CO2CH3


589
CH3
CH3
CH2CH═CH2
CH2CH2CO2CH2CH3


590
CH3
CH3
CH2CH═CH2
CH2CH2NH2


591
CH3
CH3
CH2CH═CH2
CH2CH2N(CH3)2


592
CH3
CH3
CH2CH═CH2
CH2CH2N(CH2CH3)2


593
CH3
CH3
CH2CH═CH2
CH2CH═CH2


594
CH3
CH3
CH2CH═CH2
C(CH3)═CH2


595
CH3
CH3
CH2CH═CH2
CH2CH═CHCH3


596
CH3
CH3
CH2CH═CH2
C(CH3)CH═CHCH3


597
CH3
CH3
CH2CH═CH2
CH2C≡CH


598
CH3
CH3
CH2CH═CH2
CH(CH3)C≡CH


599
CH3
CH3
CH2CH═CH2
CH2C≡CHCH3


600
CH3
CH3
CH2CH═CH2
Ph









Very particular preference is also given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Ab (≡I where R1=II-A, R10=methyl, R11=trifluoromethyl and R12=hydrogen, R2=H, R3=Cl, R6=H, X=O), where R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Ab.1 to I-Ab.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Very particular preference is also given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Ac (≡I where R1=II-A, R10=amino, R11=trifluoromethyl and R12=hydrogen, R2=F, R3=Cl, R6=H, X=O), where R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Ac.1 to I-Ac.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Very particular preference is also given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Ad (≡I where R1=II-A, R10=amino, R11=trifluoromethyl and R12=hydrogen, R2=H, R3=Cl, R6=H, X=O), where R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Ad.1 to I-Ad.600, in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-B preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Ba (≡I where R1=II-B, R13′, R13 are each methyl, R2=F, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Ba.1 to I-Ba.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-B preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Bb (≡I where R1=II-B, R13′, R13 are each methyl, R2=H, R3=Cl; R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Bb.1 to I-Bb.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-C preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Ca (≡I where R1=II-C, R14=chlorine, R15, R17=hydrogen, R16=trifluoromethyl, R2=F; R3=Cl; R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Ca.1 to I-Ca.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-C preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Cb (≡I where R1=II-C, R14=chlorine, R15, R17=hydrogen, R16=trifluoromethyl, R2=H; R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Cb.1 to I-Cb.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-C preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Cc (≡I where R1=II-C, R14=chlorine, R15, R17=hydrogen, R16=methylsulfonyl, R2=F, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Cc.1 to I-Cc.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-C preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Cd (≡I where R1=II-C, R14=chlorine, R15, R17=hydrogen, R16=methylsulfonyl; R2=H, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Cd.1 to I-Cd.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-C preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Ce (≡I where R1=II-C, R14=chlorine, R15, R17=hydrogen, R16=methylsulfonyloxy, R2=F, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Ce.1 to I-Ce.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-C preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Cf (≡I where R1=II-C, R14=chlorine, R15, R17=hydrogen, R16=methylsulfonyloxy, R2=H, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Cf.1 to I-Cf.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-D preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Da (≡I where R1=II-D, R18, R20=hydrogen, R19=trifluoromethyl, R2=F, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Da.1 to I-Da.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-D preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Db (≡I where R1=II-D, R18, R20=hydrogen, R19=trifluoromethyl, R2=H, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Db.1 to I-Db.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-D preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Dc (≡I where R1=II-D, R18=methyl, R19=trifluoromethyl, R20=hydrogen, R2=F, R3=Cl; R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Dc.1 to I-Dc.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-D preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Dd (≡I where R1=II-D, R18=methyl, R19=trifluoromethyl, R20=hydrogen; R2=H, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Dd.1 to I-Dd.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-D preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-De (≡I where R1=II-D, R18=amino, R19=methylsulfonyl, R20=hydrogen; R2=F, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-De.1 to I-De.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-D preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Df (≡I where R1=II-D, R18=amino, R19=methylsulfonyl, R20=hydrogen, R2=H, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Df.1 to I-Df.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-E preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Ea (≡I where R1=II-E, R21=chlorine, R22=trifluoromethyl, R23=methyl, R2=F, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Ea.1 to I-Ea.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-E preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Eb (≡I where R1=II-E, R21=bromine, R22=trifluoromethyl, R23=methyl, R2=Cl, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Eb.1 to I-Eb.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-E preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Ec (≡I where R1=II-E, R21=chlorine, R22=trifluoromethyl, R23=methyl; R2=H, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Ec.1 to I-Ec.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-E preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Ed (≡I where R1=II-E, R21=chlorine, R22=difluoromethoxy, R23=methyl, R2=F, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Ed.1 to I-Ed.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-E preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Ee (≡I where R1=II-E, R21=chlorine, R22=difluoromethoxy, R23=methyl, R2=H, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Ee.1 to I-Ee.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-E preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Ef (≡I where R1=II-E, R21=bromine, R22=difluoromethoxy, R23=methyl, R2=Cl, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Ef.1 to I-Ef.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-E preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Eg (≡I where R1=II-E, R21=chlorine, R22=methylsulfonyl, R23=methyl; R2=F, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Eg.1 to I-Eg.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-E preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Eh (≡I where R1=II-E, R21=bromine, R22=methylsulfonyl, R23=methyl, R2=Cl, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Eh.1 to I-Eh.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-F preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Fb (≡I where R1=II-F, R24=difluoromethyl, R25=methyl, R2=Cl, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Fb.1 to I-Fb.600 in which the variables R4 R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-F preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Fb (≡I where R1=II-E, R24=difluoromethyl, R25=methyl, R2=Cl, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Fb.1 to I-Fb.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-F preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Fc (≡I where R1=II-F, R24, R25=(CH2)4, R2=F, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Fc.1 to I-Fc.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-F preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Fd (≡I where R1=II-F, R24, R25=(CH2)4, R2=Cl, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Fd.1 to I-Fd.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-G preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Ga (≡I where R1=II-G, A1, A2 are each oxygen, R2=F, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Ga.1 to I-Ga.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-G preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Gb (≡I where R1=II-G, A1, A2 are each oxygen, R2=H, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Gb.1 to I-Gb.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-H preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Ha (≡I where R1=II-H, A3 and A4 are each oxygen, R26=difluoromethyl, R27=methyl; R2=F, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Ha.1 to I-Ha.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-H preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Hb (≡I where R1=II-H, A3 and A4 are each oxygen, R26 and R27 together are tetramethylene, R2=F, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Hb.1 to I-Hb.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




Among the compounds I-H preference is given to the 3-heterocyclyl-substituted benzoic acid derivatives of the formula I-Hc (≡I where R1=II-H, A3 and A4 are each oxygen, R26 and R27 together are tetramethylene, R2=H, R3=Cl, R6=H, X=O) in which R4, R5, R7 and R8 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds I-Hc.1 to I-Hc.600 in which the variables R4, R5, R7 and R8 together have the meanings given in one row of Table 1.




The 3-heterocyclyl-substituted benzoic acid derivatives according to the invention can be prepared similarly to known processes. If no targeted synthesis of the isolation of pure isomers is carried out, the product may be obtained as a mixture of isomers. The mixtures can, if desired, be separated into the substantially pure isomers using methods customary for this purpose such as crystallization or chromatography, including chromatography on an optically active adsorbate. Pure optically active isomers can also be prepared, for example, from appropriate optically active starting materials.
In general, the 3-heterocyclyl-substituted compounds of the formula I are prepared by reacting a 3-heterocyclyl-substituted benzoic acid derivative of the formula III




where R1, R2, R3, R4, R5 and X are as defined above, if appropriate in the presence of a coupling agent, or by reacting the acid halide which corresponds to III, with a sulfamide of the formula IV





where R6, R7 and R8 are as defined above. Processes for activating carboxylic acids are known, for example, from Houben-Weyl, Methoden der organischen Chemie [Methods of organic chemistry], Vol. E5 (1985), part 1, p. 587 ff. and Vol. E5 (1985), part II, p. 934 ff. The reaction of activated carboxylic acids III or carbonyl halides of III can be carried out analogously to the preparation of carboxylsulfamides described in WO 01/83459, for example in the manner described on p. 31 f.

Preferably, the carboxylic acid III is initially activated by reaction with a coupling agent. The activated carboxylic acid III is then, generally without prior isolation, reacted with the sulfamide IV. Suitable coupling agents are, for example, N,N′-carbonyldiimidazole or carbodiimides, such as dicyclohexylcarbodiimide. These are generally employed in at least equimolar amount and up to a fourfold excess, based on the carboxylic acid III. If appropriate, the resulting reaction mixture of carboxylic acid III and coupling agent is heated and then allowed to cool to room temperature. The reaction is usually carried out in a solvent. Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, ethers, for example dialkyl ethers such as diethyl ether or methyl tert-butyl ether, or cyclic ethers, such as tetrahydrofuran or dioxane, carboxamides, such as dimethylformamide, N-methyllactams, such as N-methylpyrrolidone, nitriles, such as acetonitrile, aromatic hydrocarbons, such as toluene, aromatic amines, such as pyridine, or mixtures of these. This is followed by addition of the sulfamide IV. In general, the sulfamide IV is dissolved in the solvent which is also used for activating the carboxylic acid.
Alternatively, the carboxylic acid III can also initially be converted into the acid halide which corresponds to III, by using an inorganic acid halide, preferably by using an acid chloride such as thionyl chloride, phosphoryl chloride, phosphorus pentachloride, oxalyl chloride or phosphorus trichloride, and the acid halide formed is, if appropriate, isolated and then reacted with the sulfamide IV. If required, the reactivity of the thionyl chloride is increased by adding catalytic amounts of dimethylformamide. The halogenating agent is usually employed in at least equimolar amount, based on the carboxylic acid. The reaction partner thionyl chloride, phosphorus trichloride or phosphoryl chloride may simultaneously act as solvent. Suitable solvents are furthermore solvents which are inert under the reaction conditions, for example chlorinated hydrocarbons, such as methylene chloride and 1,2-dichloroethane, aromatic hydrocarbons, such as benzene or toluene, aliphatic and cycloaliphatic hydrocarbons, such as hexane, petroleum ether and cyclohexane, and mixtures thereof. The reaction temperature is generally between room temperature and the boiling point of the solvent. After the reaction has ended, excess halogenating agent is generally removed. The resulting acid chloride of III is then reacted with the sulfamide IV. In general, the sulfamide IV is dissolved in the solvent which was also used for preparing the carbonyl halide, unless the solvent is one of the acid halides mentioned above.
It is, of course, also possible to use other methods for activating the carboxylic acid. Such methods are described in the prior art.
The molar ratio of carboxylic acid III or the activated carboxylic acid which corresponds to III or of the acid chloride which corresponds to III to the sulfamide IV is generally at least 0.9:1, preferably at least 1:1. If appropriate, it may also be advantageous to employ a slight excess of sulfamide IV, for example in excesses up to 30%, based on the carboxylic acid III.
The reaction is usually carried out in the presence of a base which is preferably employed in an equimolar amount or an up to fourfold excess, based on the carboxylic acid III. Suitable bases are, for example, amines, such as 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), pyridine or triethylamine. If appropriate, it may be advantageous to carry out the reaction in the presence of a catalytic amount of 4-dimethylaminopyridine (DMAP). The added base is generally 5-10 mol %, based on the activated carboxylic acid III.
In general, the reaction temperature is in the range from 0° C. to the boiling point of the reaction mixture. Work-up can be carried out in a manner known per se.
The compounds of the formula IV can be obtained by processes known per se, for example by the processes described by G. Hamprecht in Angew. Chem. 93 (1981), 151-163 or by the processes described in WO 01/83459, DE 102 21 910.9 or in Houben-Weyl, Vol. E11 (1985), p. 1019.
3-Heterocyclyl-substituted benzoic acid derivatives of the formula III are known in the prior art or can be prepared similarly to known processes, frequently from the esters that correspond to III.
In this case, the esters are converted into the corresponding carboxylic acids III according to known processes by hydrolysis in acidic media using strong mineral acids, such as concentrated hydrochloric acid or sulfuric acid, or organic acids, such as glacial acetic acids, or mixtures thereof. Alternatively, esters can also be hydrolyzed in an alkaline media using bases such as alkali metal hydroxides, for example sodium hydroxide or potassium hydroxide in the presence of water.
Solvents suitable both for the acid- and the base-catalyzed hydrolysis of esters include, for example, chlorinated aliphatic or alicyclic hydrocarbons, such as methylene chloride or 1,2-dichloroethane, or alcohols. In the case of the acid-catalyzed hydrolysis, the reaction partner usually simultaneously acts as solvent and is therefore employed in excess, based on the ester. The reaction temperature is usually between room temperature and the boiling point of the solvent.
Esters of the carboxylic acid III where R1 is a heterocyclic radical of the formula II-A are known, for example, from U.S. Pat. No. 6,207,830 and DE 197 41 411. Esters of carboxylic acids of the formula III where R1 is a heterocyclic radical of the formula II-C are known from WO 97/11059. Esters of carboxylic acids of the formula III where R1 is a radical II-E are known, for example, from WO 92/06962 and JP 09059113. Esters of carboxylic acids of the formula II-F are known, for example, from JP 61069776. Compounds III which are not explicitly described in these publications can be prepared similarly to these processes.
If the esters of carboxylic acids of the formula III are not known, they can be prepared, for example, by reacting a 3-heterocyclyl-substituted benzoic acid of the formula V




where R1, R2 and R3 are defined above with an α-aminocarboxylic acid ester or an α-hydroxycarboxylic acid ester of the formula VI

HXC(R4)(R5)COOR′  (VI)

where X, R4 and R5 are as defined above and R′ is lower alkyl, in the presence of a dehydrating agent, such as N,N′-carbonyldiimidazole or dicyclohexylcarbodiimide. Alternatively, it is also possible to initially convert the benzoic acid of the formula V into its acid halide, followed by reaction with the compound of the formula VI.

The reaction conditions correspond substantially to the conditions mentioned above for the reaction of III with IV. The reaction is usually carried out in a solvent. Suitable solvents are chlorinated hydrocarbons, such as methylene chloride and 1,2-dichloroethane, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran and dioxane, or mixtures of these. The reaction with a compound of the formula VI is usually carried out at a temperature between room temperature and the boiling point of the solvent. The resulting ester of III is then hydrolyzed, giving the desired 3-heterocyclyl-substituted carboxylic acid III. With respect to the practice of the hydrolysis, reference is made to what was said above.
The carboxylic acid V can be prepared, for example, according to WO 01/083459 or the prior art cited therein, or similarly to the processes described therein. If appropriate, the ester described in the prior art has to be converted by known methods into the carboxylic acid V. With respect to the acid- or base-catalyzed hydrolysis of esters, reference is made to what was said above. The following publications are expressly referred to:
WO 88/10254, WO 89/02891, WO 89/03825, WO 91/00278 (compounds of the formula V or their esters where R1 is a heterocyclic radical of the formula II-A), EP 0 584 655, WO 00/050409 (the esters of the compounds of the formula V where R1 is a heterocyclic radical of the formula II-B), WO 96/39392, WO 97/07104 (compounds of the formula V and/or the ester corresponding to V, where R1 is a heterocyclic radical of the formula II-D), WO 92/06962 (compounds of the formula V where R1 is a heterocyclic radical of the formula II-E).
The compounds I and their agriculturally useful salts are suitable—both as isomer mixtures and in the form of the pure isomers—as herbicides. Herbicides containing I permit very good control of plant growth on uncultivated areas. In crops such as wheat, rice, corn, soybean and cotton, they are effective against broad-leaved weeds and harmful grasses without significantly damaging the crops. This effect occurs in particular at low application rates.
Depending on the particular application method, the compounds I or the herbicidal compositions comprising them may be used in a further number of crops for eliminating unwanted plants. Suitable are, for example, the following crops:
Allium cepa, Ananas 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, Ipomoea 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. 
The compounds I may also be used in crops which are tolerant to the action of herbicides as a result of breeding, including the use of genetic engineering methods.
Furthermore, the compounds I and their agriculturally useful salts are suitable for the desiccation and/or defoliation of plants.
As desiccants, they are particularly suitable for drying out the above-ground parts of crops, such as potatoes, rape, sunflower and soybeans. This permits completely mechanical harvesting of these important crops.
Also of commercial interest is

    
    
        the concentrated dropping of fruits or the reduction of their adhesion to the plant, for example, in the case of citrus fruits, olives or other species and varieties of pomes, drupes and hard-shelled fruit, since because of this, the harvesting of these fruits is made easier, and
        the controlled defoliation of useful plants, in particular cotton.
    
    


The dropping brought about by the use of novel active compounds of the formula I depends on the formation of abscission tissue between fruit or leaf part, and shoot part of the plants.
The defoliation of cotton is of very particular commercial interest, since it makes the harvest easier. At the same time, the shortening of the period in which the individual plants ripen leads to an improved quality of the harvested fiber material.
The compounds I or the herbicidal compositions comprising them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, including highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusting agents, broadcasting agents or granules, by spraying, nebulizing, dusting, broadcasting or pouring, or for seed dressing or mixing with the seed. The application forms depend on the intended uses; they should in any case ensure very fine distribution of the active ingredients according to the invention.
The herbicides contain a herbicidally effective amount of at least one active compounds of the formula I and auxiliaries which are usually used in formulating crop protection agents.
Suitable inert auxiliaries are essentially:
mineral oil fractions having a medium to high boiling point, such as kerosine and diesel oil, and coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffins, tetrahydronaphthalene, alkylated naphthalenes and derivatives thereof, alkylated benzenes and derivatives thereof, alcohols, such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones, such as cyclohexanone, and strongly polar solvents, for example amines, such as N-methylpyrrolidone, and water.
Aqueous application forms can be prepared from emulsion concentrates, from suspensions, pastes, wettable powders or water-dispersible granules by adding water. For the preparation of emulsions, pastes or oil dispersions, the 3-heterocyclyl-substituted benzoic acid derivatives I, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, adherents, dispersants or emulsifiers. However, it is also possible to prepare concentrates which consist of active ingredients, wetting agents, adherents, dispersants or emulsifiers and possibly solvent or oil, which are suitable for dilution with water.
Suitable surfactants are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, e.g. lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and fatty acids, alkylsulfonates and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ether, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors and methylcellulose.
Powders, broadcasting agents and dusting agents can be prepared by mixing or milling the active ingredients together with a solid carrier.
Granules, for example coated, impregnated and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, kieselguhr, calcium sulfate, magnesium sulfate, magnesium oxide, milled plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and vegetable products, such as grain flour, bark meal, wood meal and nutshell meal, cellulosic powders and other solid carriers.
The concentrations of the active ingredients I in the ready-to-use formulations may be varied within wide ranges. In general, the formulations contain from about 0.001 to 98, preferably from 0.01 to 95, % by weight of at least one active ingredient I. The active ingredients are used in a purity of from 90 to 100%, preferably from 95 to 100% (according to the NMR spectrum).
The compounds I according to the invention can be formulated, for example, as follows:

    I. 20 parts by weight of a compound I are dissolved in a mixture which consists of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of from 8 to 10 mol of ethylene oxide with 1-mol of N-monoethanololeamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion which contains 0.02% by weight of the active ingredient is obtained.
    II. 20 parts by weight of a compound I are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide with 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion which contains 0.02% by weight of the active ingredient is obtained.
    III. 20 parts by weight of a compound I are dissolved in a mixture which consists of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction boiling within the range from 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion which contains 0.02% by weight of the active ingredient is obtained.
    IV. 20 parts by weight of a compound I are thoroughly mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid obtained from a sulfite waste liquor and 60 parts by weight of silica gel powder, and the mixture is milled in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor which contains 0.1% by weight of the active ingredient is obtained.
    V. 3 parts by weight of a compound I are mixed with 97 parts by weight of finely divided kaolin. A dusting agent which contains 3% by weight of the active ingredient is obtained in this manner.
    VI. 20 parts by weight of a compound I are thoroughly mixed with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.
    VII. 1 part by weight of a compound I is dissolved in a mixture which consists of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.
    VIII. 1 part by weight of a compound I is dissolved in a mixture which consists of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM31 (=nonionic emulsifier based on ethoxylated castor oil; BASF AG). A stable emulsion concentrate is obtained.


The active compounds I or the herbicidal compositions can be applied by the preemergence or postemergence method. The herbicidal compositions or active compounds can also be applied by sowing crop seed which has been pretreated with the herbicidal compositions or active compounds. If the active ingredients are less well tolerated by certain crops, it is possible to use application methods in which the herbicides are sprayed with the aid of the sprayers in such a way that the leaves of the sensitive crops are as far as possible not affected, while the active compounds reach the leaves of undesirable plants growing underneath or the uncovered soil surface (post-directed, lay-by).
The application rates of active compound I are from 0.001 to 3.0, preferably from 0.01 to 1.0, kg/ha of active ingredient (a.i.), depending on the aim of control, the season, the target plants and the state of growth.
In order to broaden the action spectrum and to achieve synergistic effects, the 3-heterocyclyl-substituted benzoic acid derivatives I may be mixed with many members of other groups of herbicidal or growth-regulating active ingredients and applied together with them.
Examples of suitable components of the mixture are 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and derivatives thereof, aminotriazoles, anilides, aryloxy-/hetaryloxyalkanoic acids and derivatives thereof, benzoic acid and derivatives thereof, benzothiadiazinones, 2-(hetaroyl/aroyl)-1,3-cyclohexanediones, hetarylarylketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and derivatives thereof, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and derivatives thereof, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and derivatives thereof, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and derivatives thereof, 2-phenylpropionic acid and derivatives thereof, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and derivatives thereof, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolcarboxamides and uracils.
It may also be useful to apply the compounds I together, alone or in combination with other herbicides, also as a mixture with further crop protection agents, for example with pesticides or agents for controlling phytopathogenic fungi or bacteria. The miscibility with mineral salt solutions which are used for eliminating nutrient and trace element deficiencies is also of interest. Nonphytotoxic oils and oil concentrates can also be added.
The examples below are intended to illustrate the invention without limiting it.


PREPARATION EXAMPLES
Example 1
(S)-2-[2-Chloro-5-(3-methyl-2,6-dioxo-4-trifluoro methyl-3,6-dihydro-2H-pyrimidin-1-yl)-4-fluorobenzoyloxy]propionic acid N,N-dimethylsulfamide (S-enantiomer of compound I-Aa. 242)




1.1: 2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoic acid
13.9 g (34 mmol) of isopropyl 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoate (CAS No. 105756-82-9, U.S. Pat. No. 5,176,735, U.S. Pat. No. 4,943,309, WO 88/10254) were dissolved in 100 ml of glacial acetic acid and 100 ml of conc. HCl, and the mixture was heated at 70° C. for 15 hours. The acetic acid was removed under reduced pressure, the residue was taken up in water and the resulting precipitate was filtered off with suction. Drying gave 11.3 g of the uracilcarboxylic acid which was used for the next step without further purification.
1H-NMR (DMSO-d6) δ (ppm)=8.1 (d, 1H), 7.8 (d, 1H), 6.6 (s, 1H), 3.4 (s, 3H).
1.2: Methyl (S)-2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoro methyl-3,6-dihydro-2H-pyrimidin-1-yl)-4-fluorobenzoyloxy]propionate
5.0 g (13.64 mmol) of uracilcarboxylic acid from 1.1 in 50 ml of thionyl chloride were heated at reflux for 3 h, and unreacted thionyl chloride was then removed under reduced pressure. The resulting acid chloride was then dissolved in 50 ml of methylene chloride, and the resulting solution was, at 0-5° C., added dropwise with stirring to a solution of 1.6 g (15.01 mmol) of methyl (S)-lactate, 0.2 g (1.36 mmol) of 4-dimethylaminopyridine (DMAP) and 1.7 g (16.37 mmol) of triethylamine in 80 ml of CH2Cl2. The mixture was allowed to warm to room temperature and stirred at room temperature for another 16 hours. The reaction mixture was then concentrated and chromatographed on silica gel using cyclohexane/ethyl acetate 70/30. The solvent was evaporated under reduced pressure, giving 5.85 g of the ester.
1H-NMR (DMSO-d6) δ (ppm)=8.0 (d, 1H), 7.4 (d, 1H), 6.4 (s, 1H), 5.4 (q, 1H), 4.8 (s, 3H), 3.6 (s, 3H), 1.5 (d, 3H).
1.3: (S)-2-Chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-4-fluorobenzoyloxy]propionic acid
25 ml of glacial acetic acid and 25 ml of conc. HCl were added to 3.6 g (8 mmol) of the ester from 1.2, the mixture was heated at 60° C. for 4 hours and then stirred at room temperature for 8 hours. The acetic acid was removed under reduced pressure and the reaction mixture was diluted with water and extracted three times with in each case about 150 ml of ethyl acetate. The combined organic phases were then dried over Na2SO4 and concentrated under reduced pressure, giving 3.3 g of acid.
1H-NMR (DMSO-d6) δ (ppm)=8.0 (d, 1H), 7.4 (d, 1H), 6.4 (s, 1H), 5.4 (q, 1H), 3.5 (s, 3H), 1.6 (d, 3H).
1.4: (S)-2-[2-Chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-4-fluorobenzoyloxy]propionic acid N,N-dimethylsulfamide
0.45 g (1.03 mmol) of the acid from 1.3 in 10 ml of thionyl chloride was heated at reflux for 3 hours and excess thionyl chloride was then removed under reduced pressure and the resulting acid chloride was dissolved in about 5 ml of CH2Cl2. This solution was, at about 5° C., added dropwise to a solution of 0.13 g (1.03 mmol) of N,N-dimethylsulfamide, 0.23 g (2.23 mmol) of triethylamine and a catalytic amount of DMAP in 20 ml of CH2Cl2. The reaction mixture was stirred at room temperature for 14 hours and then concentrated under reduced pressure. The residue was taken up in ethyl acetate and washed with about 200 ml of 10% strength hydrochloric acid. Chromatography on silica gel using cyclohexane/ethyl acetate 70/30 gave 0.16 g of the title compound of m.p. 207-208° C.
1H-NMR: see Table 2
Example 2
2-[2-Chloro-5-(3-methyl-2,6-dioxo-4-trifluoro-methyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoyloxy]-2-methyl-propionic acid N-methyl-N-allylsulfamide (compound I-Ab.465)
0.33 g (2.2 mmol) of N-methyl-N-allylsulfamide, 0.27 g of 4-dimethylaminopyridine and 0.64 ml of triethylamine were dissolved in 10 ml of dichloromethane. A solution of 0.98 g (2.2 mmol) of 2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoro-methyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoyloxy]-2-methyl-propionyl chloride (CAS No. 160152-72-7) in dichloromethane was then added dropwise. The solution was stirred for 3 days and then concentrated, and the residue was taken up in ethyl acetate. The organic phase was washed with 10% strength hydrochloric acid and water and dried over sodium sulfate, the drying agent was filtered off and the filtrate was concentrated. Column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2:1) gave 0.21 g of the title compound of melting point 161-164° C.
Example 3
(S)-2-[2-Chloro-5-(3-methyl-2,6-dioxo-4-trifluoro-methyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoyloxy]propionic acid N-methyl-N-allylsulfamide (S enantiomer of compound I-Ab.265)
3.1: Methyl (S)-2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoro-methyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoyloxy]propionate
7.0 g (20 mmol) of 2-chloro-5-(3-methyl-2,6-dioxo-4-tri-fluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoic acid (CAS No. 120890-58-6) were dissolved in 50 ml of thionyl chloride. The reaction mixture was then heated under reflux for 3 hours, and the resulting solution of the acid chloride was concentrated. 2.3 g (22 mmol) of methyl (S)-lactate, 2.46 g (20 mmol) of 4-dimethylaminopyridine and 2.44 g (20 mmol) of triethylamine were then dissolved in 50 ml of dichloromethane, and a solution of the acid chloride obtained above in dichloromethane was then added dropwise at 0° C. The reaction mixture was stirred at room temperature for 16 hours, and the solution was then concentrated. Column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2:1) gave 7.0 g of methyl (S)-2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-di-hydro-2H-pyrimidin-1-yl)benzoyloxy]propionate of melting point 59-60° C.
3.2: (S)-2-[2-Chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoyloxy]propionic acid
7.0 g (16 mmol) of methyl (S)-2-[2-chloro-5-(3-methyl-2,6-di-oxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoyl-oxy]propionate from example 3.1 were dissolved in 50 ml of acetic acid, 50 ml of conc. hydrochloric acid were added and the solution was heated under reflux for 4 hours. Most of the acetic acid was distilled off, and the solution that remained was poured onto ice-water. The aqueous phase was extracted three times with ethyl acetate, the organic phase was dried over sodium sulfate, the drying agent was filtered off and the filtrate was concentrated to dryness, which gave 5.7 g of (S)-2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoyloxy]propionic acid.
3.3: (S)-2-[2-Chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoyloxy]propionyl chloride
5.7 g (14 mmol) of (S)-2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoyloxy]-propionic acid from example 3.2 were dissolved in 50 ml of thionyl chloride, and the reaction mixture was heated under reflux for 3.5 hours. The solution was allowed to cool and concentrated, which gave 5.9 g of (S)-2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoyloxy]propionyl chloride.
3.4: (S)-2-[2-Chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoyloxy]propionic acid N-methyl-N-allylsulfamide
0.33 g (2.2 mmol) of N-methyl-N-allylsulfamide, 0.27 g of 4-dimethylaminopyridine and 0.67 ml of triethylamine were dissolved in 10 ml of dichloromethane, and a solution of 0.98 g (2.2 mmol) of (S)-2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoro-methyl-3,6-dihydro-2H-pyrimidin-1-yl)benzoyloxy]propionyl chloride from example 3.3 in 10 ml of dichloromethane was added dropwise. The solution was stirred for 16 hours and then concentrated, and the resulting residue was dissolved in ethyl acetate. The organic phase was washed with 10% strength hydrochloric acid and water and dried over sodium sulfate, the drying agent was filtered off and the filtrate was concentrated. Column chromatography on silica gel gave 0.26 g of the title compound.
Example 4
2-[2-Chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-4-fluorobenzoyloxy]-2-methyl-propionic acid N,N-dimethyl-N-allylsulfamide (compound I-Aa.442)
4.1: Methyl 2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoro-methyl-3,6-dihydro-2H-pyrimidin-1-yl)-4-fluorobenzoyloxy]-2-methylpropionate
0.61 g (5.2 mmol) of methyl 2-hydroxy-2-methylpropionate, 70 mg (0.5 mmol) of 4-N-pyrrolidinopyridine and 0.87 ml (6.2 mmol) of triethylamine were dissolved in 50 ml of tetrahydrofuran, and a solution of 2 g (5.2 mmol) of the acid chloride from example 1.2 in 50 ml of tetrahydrofuran were then added dropwise. The solution was stirred for 16 hours and then concentrated, and the residue was then dissolved in ethyl acetate. The organic phase was washed with 10% strength citric acid and water and dried over sodium sulfate, the drying agent was filtered off and the filtrate was concentrated. Column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2:1) gave 1.0 g of methyl 2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-4-fluorobenzoyloxy]-2-methyl-propionate.
4.2: 2-[2-Chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-4-fluorobenzoyloxy]-2-methyl-propionic acid
1.0 g (2.1 mmol) of methyl 2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-4-fluoro-benzoyloxy]-2-methylpropionate from example 4.1 was dissolved in 50 ml of acetic acid, 50 ml of conc. hydrochloric acid were added and the reaction mixture was heated under reflux for 5 hours. Most of the acetic acid was distilled off, and the solution that remained was poured into ice-water. The precipitate was filtered off and dried, which gave 0.65 g of 2-[2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-4-fluorobenzoyloxy]-2-methylpropionic acid.
4.3: 2-[2-Chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-di-hydro-2H-pyrimidin-1-yl)-4-fluorobenzoyloxy]-2-methylpropionic acid N,N-dimethylsulfamide
0.65 g (1.4 mmol) of 2-[(2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimdin-1-yl)-4-fluorobenzoyloxy]-2-methylpropionic acid from example 4.2 was dissolved in 30 ml of thionyl chloride, the reaction mixture was heated under reflux for 3 hours and the resulting solution of the acid chloride was then concentrated. 0.18 g (1.4 mmol) of N,N-dimethylsulfamide, 0.07 g (1.4 mmol) of 4-dimethylaminopyridine and 0.35 ml (3.5 mmol) of triethylamine were dissolved in 10 ml of dichloromethane, and a solution of the acid chloride which had been prepared beforehand in 10 ml of dichloromethane was then added dropwise. The solution was stirred for 16 hours and then concentrated, and the residue was then dissolved in ethyl acetate. The organic phase was washed with 10% strength hydrochloric acid and water, the organic phase was dried over sodium sulfate, the drying agent was filtered off and the filtrate was concentrated. Column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2:1) gave 0.30 g of the title compound of melting point 211-213° C.
In addition to the benzoic acid derivatives of the formula I described above, Table 2 below lists further compounds of the formula I which were prepared analogously.









TABLE 2





No.
1H-NMR δ [ppm],
m.p. [° C.]







S-enantiomer
(CDCl3): 8.7(br., 1H), 8.0(m, 1H),
207–208


of
7.5(d, 1H), 6.4(s, 1H), 5.4(m, 1H),


the
3.5(s, 3H), 2.9(s, 6H), 1.6(d, 3H).


compound


I-Aa.242


S-enantiomer
(CDCl3): 8.7(br., 1H), 8.0(m, 1H),
170–171


of
7.5(d, 1H), 6.4(s, 1H), 5.4(m, 1H),


the
3.5(s, 3H), 3.4(q, 2H), 2.9(s, 3H),


compound
1.6(d, 3H), 1.3(t, 3H),


I-Aa.243


S-enantiomer
(CDCl3): 8.7(br., 1H), 8.0(m, 1H),
164–165


of
7.5(d, 1H), 6.4(s, 1H), 5.4(m, 1H),


the
4.2(m, 1H), 3.5(s, 3H), 2.9(s, 3H),


compound
1.6(d, 3H), 1.3(d, 6H).


I-Aa.246


S-enantiomer
(CDCl3): 8.7(br., 1H), 8.0(m, 1H),
132–134


of
7.5(d, 1H), 6.4(s, 1H), 5.4(m, 1H),


the
3.6–3.4(m, 7H), 3.3(s, 3H), 2.9(s,


compound
3H), 1.6(d, 3H).


I-Aa.251


S-enantiomer
(CDCl3): 8.7(br., 1H), 8.0(m, 1H),
129–130


of
7.5(d, 1H), 6.4(s, 1H), 5.9–5.8(m, 1H),


the
5.5–5.1(m, 3H), 3.9(d, 1H), 3.5(s, 3H),


compound
2.9(s, 3H), 1.6(d, 3H).


I-Aa.265


S-enantiomer
(CDCl3): 8.7(br., 1H), 8.0(m, 1H),


of
7.5(d, 1H), 6.4(s, 1H), 5.4(m, 1H),


the
4.2(m, 2H), 3.5(s, 3H), 2.9(s, 3H),


compound
2.3(m, 1H), 1.6(d, 3H).


I-Aa.269


I-Ab.465
(DMSO-d6): 11.7(br. s, 1H), 7.9(m, 1H),
161–164



7.7(m, 1H), 7.6(m, 1H), 6.6(s, 1H),



5.8(m, 1H), 5.3–5.2(m, 2H), 3.8(d,



2H), 3.4(s, 3H), 2.8(s, 3H), 1.6(s,



6H).


I-Ab.469
(DMSO-d6): 11.7(br. s, 1H), 7.9(m, 1H),



7.7(m, 1H), 7.6(m, 1H), 6.6(s, 1H),



4.1(d, 2H), 3.4(s, 3H), 3.3(t, 3H),



2.8(s, 3H), 1.6(s, 6H).


I-Ab.442
(DMSO-d6): 11.7(br. s, 1H), 7.9(m, 1H),



7.7(m, 1H), 7.6(m, 1H), 6.6(s, 1H),



4.0(m, 1H), 3.4(s, 3H), 2.8(s, 6H),



1.6(s, 6H).


S-enantiomer

oil


of


compound


I-Ab.248


S-enantiomer

oil


of


compound


I-Ab.242


S-enantiomer

oil


of


compound


I-Ab.243


S-enantiomer

oil


of


compound


I-Ab.265


I-Ab.443

193–194


I-Ab.446

177–179


I-Ab.448

140–142


I-Aa.442
(DMSO-d6): 11.63(s, 1H), 8.13(d, 1H),
211–213



7.91(d, 1H), 6.63(s, 1H), 3.42(s, 3H),



2.84(s, 6H), 1.61(s, 6H)









Use Examples
The herbicidal activity of the 3-heterocyclyl-substituted benzoic acid derivatives I was demonstrated by the following greenhouse experiments:
The cultivation containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.
For the preemergence treatment, directly after sowing the active compounds, which had been suspended or emulsified in water, were applied by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this was adversely affected by the active compounds.
For the postemergence treatment, the test plants were first grown to a height of 3-15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. The test plants were for this purpose either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to the treatment. The application rate for the postemergence treatment was 7.8 or 3.9 g of a.i. (active ingredient)/ha.
Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.
Evaluation was carried out using a scale from 0.0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts, and 0 means no damage, or normal course of growth.
The plants used in the greenhouse experiments were of the following species:














Scientific name
Common name









Amaranthus retroflexus
redroot pigweed



Chenopodium album
lambsquarters




(goosefoot)










Applied by the postemergence method, the S enantiomer of the compound I-Aa.246 showed excellent herbicidal activity against the abovementioned plants.
Use Examples
Desiccant/Defoliant Action
The test plants used were young cotton plants with 4 leaves (without cotyledons) which had been grown under greenhouse conditions (re1. atmospheric humidity 50-70%; day/night temperature 27/20° C.).
The young cotton plants were subjected to foliar treatment to runoff point with aqueous preparations of the active compounds (with addition of 0.15% by weight, based on the spray mixture, of the fatty alcohol alkoxylate Plurafac® LF 7001)). The amount of water applied was 1000 l/ha (converted). After 13 days, the number of leaves shed and the degree of defoliation in % were determined. 1) a low-foam, nonionic surfactant from BASF AG
The untreated control plants did not shed any leaves.

## Claims

1. A 3-heterocyclyl-substituted benzoic acid compound of the formula I




wherein:
X is oxygen or NR9,
R1 is a heterocyclic radical of the formulae II-A to II-D,




R2 is hydrogen or halogen,
R3 is halogen or cyano,
R4, R5 independently of one another are hydrogen, C1-C4-alkyl or C1-C4-alkoxy, or R4 and R5 together are a group ═CH2,
R6 is hydrogen, C1-C4-alkyl or C1-C4-alkoxy,
R7, R8 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl, cyano-C1-C4-alkyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl, amino-C1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, di(C1-C4-alkyl)amino-C1-C4-alkyl, aminocarbonyl-C1-C4-alkyl, (C1-C4-alkylamino)carbonyl-C1-C4-alkyl, di(C1-C4-alkyl)aminocarbonyl-C1-C4-alkyl, phenyl or C1-C4-alkylphenyl or
R9 is hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, phenyl, phenyl-C1-C4-alkyl, C3-C6-alkenyl or C3-C6-alkynyl,
R10 is hydrogen, C1-C4-alkyl or amino,
R11 is C1-C4-alkyl or C1-C4-haloalkyl,
R12 is hydrogen or C1-C4-alkyl,
R13, R13′ independently of one another are hydrogen or C1-C4-alkyl,
R14 is halogen,
R15 is hydrogen or C1-C4-alkyl,
R16 is C1-C4-haloalkyl, C1-C4-alkylthio, C1-C4-alkylsulfonyl or C1-C4-alkylsulfonyloxy,
R17 is hydrogen or C1-C4-alkyl,
R18 is hydrogen, C1-C4-alkyl or amino,
R19 is C1-C4-haloalkyl, C1-C4-alkylthio or C1-C4-alkylsulfonyl,
R20 is hydrogen or C1-C4-alkyl,
R21 is hydrogen, halogen or C1-C4-alkyl, or an agriculturally useful salt thereof.

2. A benzoic acid compound as claimed in claim 1 where R2 is fluorine, chlorine or hydrogen.

3. A benzoic acid compound as claimed in claim 1 where R3 is chlorine or cyano.

4. A benzoic acid compound as claimed in claim 1 where X is oxygen.

5. A benzoic acid compound as claimed in claim 1 where R6 is hydrogen.

6. A benzoic acid compound as claimed in claim 1 where R1 is a heterocyclic radical of the formula II-A in which R10 is C1-C4-alkyl or amino, R11 is C1-C4-haloalkyl and R12 is hydrogen.

7. A benzoic acid compound as claimed in claim 1 where R1 is a heterocyclic radical of the formula II-B in which R13 and R13′ are each independently of one another C1-C4-alkyl.

8. A benzoic acid compound as claimed in claim 1 where R1 is a heterocyclic radical of the formula II-C in which R14 is fluorine or chlorine, R15 is hydrogen and R16 is C1-C4-haloalkyl, C1-C4-alkylsulfonyl or C1-C4-alkylsulfonyloxy.

9. A benzoic acid compound as claimed in claim 1 where R1 is a heterocyclic radical of the formula II-D in which R18 is hydrogen, methyl or amino, R19 is C1-C4-haloalkyl or C1-C4-alkylsulfonyl and R19 is hydrogen.

10. A benzoic acid compound as claimed in claim 1 where
R2 is hydrogen, chlorine or fluorine,
R3 is chlorine or cyano,
R6 is hydrogen and
X is oxygen.

11. A benzoic acid compound as claimed in claim 1 where R4 or R5 is hydrogen and the other radical R4 or R5 is C1-C4-alkyl or R4, R5 are each methyl.

12. A composition comprising a herbicidally effective amount of at least one 3-heterocyclyl-substituted benzoic acid compound of the formula I or an agriculturally useful salt thereof as claimed in claim 1 and at least one inert liquid and/or solid carrier and, if desired, at least one surfactant.

13. A composition for the desiccation/defoliation of plants, comprising an effective amount of at least one 3-heterocyclyl-substituted benzoic acid compound of the formula I or an agriculturally useful salt thereof as claimed in claim 1 which acts as a desiccant/defoliant and at least one inert liquid and/or solid carrier and, if desired, at least one surfactant.

14. A method for controlling unwanted vegetation, which comprises applying a herbicidally effective amount of at least one 3-heterocyclyl-substituted benzoic acid compound of the formula I or an agriculturally useful salt thereof as claimed in claim 1 to act on plants, their habitat and/or on seed.

15. A method for the desiccation/defoliation of plants, which comprises applying an amount which is effective as a desiccant/defoliant of at least one 3-heterocyclyl-substituted benzoic acid compound of the formula I or an agriculturally useful salt thereof as claimed in claim 1 to act on plants.

16. A method for controlling unwanted vegetation or for the desiccation/defoliation of plants, comprising applying to plants, the habitat of the plants or seeds of the plants an agriculturally effective amount of a compound or salt of claim 1.