# Patent

## Title
N-aryl[1,2,4]triazolo[1,5-a]pyrazine-2-sulfonamide herbicides

## Abstract

where R.sup.3 to R.sup.6 have the meanings given in the specification. The compounds are useful as herbicides and for the desiccation/defoliation of plants.

## Background
This application is a National Stage Application of PCT/EP93/01216 filed May 14, 1993 and published as WO 93/24456 on Dec. 9, 1993.

The present invention relates to substituted isoindolones of the general formula I ##STR2## where the variables have the following meanings: R.sup.1 and R.sup.2 are -C.sub.6 -alkynyl, tri-(C.sub.1 -C.sub.6 -alkyl)silyl-C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, cyano, C.sub.1 -C.sub.6 -cyanoalkyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, formyl, C.sub.1 -C.sub.6 -alkylcarbonyl, phenylcarbonyl where the phenyl ring can be unsubstituted or can carry one to three radicals selected from a group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, halogen, cyano, nitro and trifluoromethyl, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl or C.sub.1 -C.sub.6 -haloalkyl, selected from a group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, halogen, cyano, nitro and trifluoromethyl, or R.sup.1 and R.sup.2, together with the common C atom to which they are bonded, are a three- to eight-membered saturated or unsaturated non-aromatic carbo- or heterocycle which can carry one to three N atoms and an additional oxygen or sulphur atom and also one or two carbonyl groups, and can be substituted by one to three identical or different C.sub.1 -C.sub.6 -alkyl groups; saturated or partially or completely unsaturated and can carry one to four heteroatoms, selected from a group consisting of one to four nitrogen atoms, one or two oxygen atoms and one or two sulfur atoms, where the heterocycle can carry one of the following substituents on each substitutable atom: C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkoxycarbonyl, or --C(R.sup.10).dbd.N--R.sup.11, --C(X.sup.1 R.sup.14) (X.sup.2 R.sup.15)R.sup.10, --P(R.sup.12) (R.sup.13).dbd.O, where -C.sub.4 -alkynylene chain which can in each case be unsubstituted or can carry one or two radicals selected from a group consisting of halogen, cyano, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxycarbonyl and C.sub.1 -C.sub.6 -alkylcarbonyl; -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.8 -cycloalkyl -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.2 -C.sub.6 -haloalkyl, selected from a group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -alkoxycarbonyl, -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkoximino-C.sub.1 -C.sub.6 -alkyl; selected from a group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -alkoxycarbonyl; are hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl or phenyl which can be unsubstituted or can carry one to three radicals selected from a group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.8 -alkoxycarbonyl, or where R.sup.8 and R.sup.9, together with the common nitrogen atom, form a saturated or partially or completely unsaturated 4- to 7-membered ring which can additionally contain one or two further heteroatoms as ring members, selected from a group consisting of nitrogen, oxygen and sulfur; -alkoxy)-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.6 -alkyl; -alkynyl, -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.6 -haloalkyl, selected from a group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -alkoxycarbonyl, -C.sub.7 -cycloalkoxy, C.sub.5 -C.sub.7 -cycloalkenyloxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.3 -C.sub.6 -haloalkenyloxy, C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.6 -alkoxy, -alkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkoxy, hydroxy-C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylamino-C.sub.1 -C.sub.6 -alkoxy, di-(C.sub.1 -C.sub.6 -alkyl)-amino-C.sub.1 -C.sub.6 -alkoxy, phenyl-C.sub.3 -C.sub.6 -alkynyloxy, where in each case one or two methylene groups of the alkoxy, alkenyloxy and alkynyloxy chains can be replaced by oxygen, sulfur and/or a C.sub.1 -C.sub.6 -alkylamino chain, and where the phenyl ring can be unsubstituted or can carry one to three substituents selected from a group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -alkoxycarbonyl, one to three radicals selected from a group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -alkoxycarbonyl; -alkynyl or C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl or which can be unsaturated and which, if desired, can contain a carbonyl group as a ring member, where the carbon chain can be unsubstituted or can carry one to three radicals selected from a group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, halogen, cyano, nitro, amino, C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy, carboxyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyloxy-C.sub.2 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkynyloxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -hydroxyalkyl and C.sub.1 -C.sub.6 -cyanoalkyl; unsaturated three- to five-membered carbon chain which, if desired, can contain one or two oxygen, sulfur or nitrogen atoms and/or a carbonyl group as ring members, and where the chain can be unsubstituted or can in turn carry one or two radicals selected from a group consisting of cyano, nitro, amino, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -cyanoalkyl, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl, phenyl-C.sub.1 -C.sub.6 -alkyl and 3- to 8-membered heterocyclyl-C.sub.1 -C.sub.6 -alkyl, where the heterocycle can be saturated or partially or completely unsaturated and can carry one to four heteroatoms selected from a group consisting of one to four nitrogen atoms, one or two oxygen atoms and one or two sulfur atoms; either chain --O--CH.sub.2 --CO--NH--,

and the agriculturally utilizable salts of the compounds I.

The invention additionally relates to novel intermediates of the formula II.

In addition, the invention relates to herbicides and plant growth regulators which contain these compounds as active substances.

EP-A 420,810 discloses herbicidal substituted isoindolones of the formula I': ##STR3## where R.sup.a and R.sup.b are hydrogen, alkyl, unsubstituted or substituted phenyl or, together, are an alkyl-substituted alkylene chain, R.sup.c and R.sup.d are hydrogen, alkyl or, together, are alkyl-substituted tetramethylene, R.sup.a is hydrogen or fluorine, R.sup.f is halogen and R.sup.9 is O--W--S(O).sub.m --Q or SAQ1, where W is C.sub.1 -C.sub.4 -alkylene, m is 0-2 and Q is alkyl, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl, phenyl or benzyl.

In addition, JA 01/139580 inter alia describes compounds of the formula I" ##STR4## and their use as herbicides, where R.sup.h is hydrogen or alkyl and R.sup.i is substituted O-containing heterocycles, unsubstituted or halogen-substituted alkyl, alkenyl or alkynyl, alkoxyalkyl or alkylthioalkyl.

Additionally, compounds of the formula I'" ##STR5## are to be inferred, inter alia, from DE-A 3,924,052, where R.sup.k is hydrogen or halogen, R.sup.1 is hydrogen, alkyl or halogen, R.sup.m is hydrogen or alkyl and R.sup.n is hydrogen, unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, haloalkyl, alkoxycarbonyl or (di)alkylaminocarbonyl, alkylcarbonyl or alkylsulfonyl.

In addition, JA 88/039859 inter alia discloses herbicidal compounds of the formula I"", ##STR6## where R.sup.0 is, inter alia, hydroxyl, mercapto, phenoxy, alkoxy, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, alkoxycarbonylalkoxycarbonyl or a carbonate radical. EP-A 305,333, EP-A 403,891, U.S. Pat. No. 3,992,189 and JA 03/287,766.

The selectivity of these known herbicides with respect to harmful plants can only be satisfactory, however, in a limited manner, so that it is an object of the present invention to find herbicidal compounds using which (with good tolerability for the crop plants) the harmful plants can be specifically controlled better than hitherto.

We have found that this object is achieved by the substituted isoindolones I defined at the beginning.

In addition, we have found herbicides which contain these substances and have a good herbicidal action.

Additionally, we have found that the compounds I of the invention are suitable as defoliants and desiccants, for example in cotton, potato, rape, sunflowers, soya beans or field beans.

The meanings mentioned above for the substituents R.sup.1 to R.sup.16 are collective terms for individual lists of the single group members. All alkyl, alkenyl, alkynyl, haloalkyl and haloalkoxy moieties can be straight-chain or branched. Haloalkyl and haloalkoxy radicals can carry identical or different halogen atoms.

Specific examples are: chlorine; radicals di-(C.sub.1 -C.sub.6 -alkoxy)-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyloxy-C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkynyloxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoximino-C.sub.1 -C.sub.6 -alkyl, tri-(C.sub.1 -C.sub.6 -alkyl)silyl-C.sub.2 -C.sub.6 -alkynyl and heterocyclyl-C.sub.1 -C.sub.6 -alkyl: 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, preferably methyl, ethyl, isopropyl and tert.-butyl; radical C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.2 -C.sub.6 -alkenyl: ethenyl and C.sub.3 -C.sub.6 -alkenyl such as prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl, n-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, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-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, n-hex-1-en-1-yl, n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl, 1-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 and 1-ethyl-2-methylprop-2-en-1-yl, preferably ethenyl and prop-2-en-1-yl; radical tri-(C.sub.1 -C.sub.6 -alkyl)silyl-C.sub.2 -C.sub.6 -alkynyl: ethynyl and C.sub.3 -C.sub.6 -alkynyl such as prop-1-in-1-yl, prop-2-in-3-yl; the radical C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.6 -alkoxy: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, preferably cyclopropyl, cyclopentyl and cyclohexyl; 2-cyanoeth-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-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, 1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-cyano-2-methylprop-3-yl, 2-cyano-2-methylprop-3-yl, 3-cyano-2-methylprop-3-yl, and 2-cyanomethylprop-2-yl, preferably cyanomethyl; fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 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 and 3-chloropropyl, preferably trifluoromethyl; 2-cyanoeth-1-oxy, 1-cyanoprop-1-oxy, 2-cyanoprop-1-oxy, 3-cyanoprop-1-oxy, 1-cyanoprop-2-oxy, 2-cyano-prop-2-oxy, 1-cyanobut-1-oxy, 2-cyanobut-1-oxy, 3-cyanobut-1-oxy, 4-cyanobut-1-oxy, 1-cyanobut-2-oxy, 2-cyanobut-2-oxy, 1-cyanobut-3-oxy, 2-cyanobut-3-oxy, 1-cyano-2-methylprop-3-oxy, 2-cyano-2-methylprop-3-oxy, 3-cyano-2-methylprop-3-oxy, and 2-cyanomethylprop-2-oxy, preferably cyanomethoxy; 2-hydroxyeth-1-oxy, 1-hydroxyprop-1-oxy, 2-hydroxyprop-1-oxy, 3-hydroxyprop-1-oxy, 1-hydroxyprop-2-oxy, 2-hydroxyprop-2-oxy, 1-hydroxybut-1-oxy, 2-hydroxybut-1-oxy, 3-hydroxybut-1-oxy, 4-hydroxybut-1-oxy, 1-hydroxybut-2-oxy, 2-hydroxybut-2-oxy, 1-hydroxybut-3-oxy, 2-hydroxybut-3-oxy, 1-hydroxy-2-methylprop-3-oxy, 2-hydroxy-2-methylprop-3-oxy, 3-hydroxy-2-methylprop-3-oxy and 2-hydroxymethylprop-2-oxy, preferably hydroxymethoxy; 1-phenylprop-1-oxy, 1-phenylprop-1-oxy, 3-phenylprop-1-oxy, 1-phenylbut-1-oxy, 2-phenylbut-1-oxy, 3-phenylbut-1-oxy, 4-phenylbut-1-oxy, 1-phenylbut-2-oxy, 2-phenylbut-2-oxy, 3-phenylbut-2-oxy, 4-phenylbut-2-oxy, 1-(phenylmethyl)-eth-1-oxy, 1-(phenylmethyl)-1-(methyl)-eth-1-oxy, and 1-(phenylmethyl)-prop-1-oxy, preferably benzyloxy; radicals C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.7 -cycloalkyl-C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkoxy, di- (C.sub.1 -C.sub.6 -alkoxy)-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkylamino-C.sub.1 -C.sub.6 -alkoxy and di(C.sub.1 -C.sub.6 -alkyl)-amino-C.sub.1 -C.sub.6 -alkoxy: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy, preferably C.sub.1 -C.sub.4 -alkoxy such as methoxy, ethoxy, n-propoxy and n-butoxy; the radical C.sub.3 -C.sub.6 -alkenyloxy-C.sub.1 -C.sub.6 -alkyl: prop-2-en-1-yloxy, n-buten-4-yloxy, n-buten-3-yloxy, 1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, n-penten-5-yloxy, 1-methylbut-2-en-1-yloxy, 2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy, 1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy, 3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy, 1-ethylprop-2-en-1-yloxy, n-hex-2-en-1-yloxy, n-hex-3-en-1-yloxy, n-hex-4-en-1-yloxy, n-hex-5-en-1-yloxy, 1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy, 3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy, 1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy, 3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy, 1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy, 3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy, 1,1-dimethylbut-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy, 1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy, 2,2-dimethyl-but-3-en-1-yloxy, 2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy, 1-ethylbut-2-en-1-yloxy, 1-ethylbut-3-en-1-yloxy, 2-ethylbut-2-en-1-yloxy, 2-ethyl-but-3-en-1-yloxy, 1,1,2-trimethylprop-2-en-1-yloxy, 1-ethyl-1-methylprop-2-en-1-yloxy and 1-ethyl-2-methylprop-2-en-1-yloxy, preferably ethenyloxy and prop-2-en-1-yloxy; the radical C.sub.3 -C.sub.6 -alkynyloxy-C.sub.1 -C.sub.6 -alkyl: prop-1-yn-1-yloxy, prop-2-yn-3-yloxy, n-but-1-yn-4-yloxy, n-but-2-yn-1-yloxy, n-pent-1-yn-3-yloxy, n-pent-1-yn-4-yloxy, n-pent-1-yn-5-yloxy, pent-2-yn-1-yloxy, pent-2-yn-4-yloxy, pent-2-yn-5-yloxy, 3-methylbut-1-yn-3-yloxy, 3-methylbut-1-yn-4-yloxy, n-hex-1-yn-3-yloxy, n-hex-1-yn-4-yloxy, n-hex-1-yn-5-yloxy, n-hex-1-yn-6-yloxy, n-hex-2-yn-1-yloxy, n-hex-2-yn-4-yloxy, n-hex-2-yn-5-yloxy, n-hex-2-yn-6-yloxy, n-hex-3-yn-1-yloxy, n-hex-3-yn-2-yloxy, 3-methylpent-1-yn-3-yloxy, 3-methylpent-1-yn-4-yloxy, 3-methylpent-1-yn-5-yloxy, 4-methylpent-2-yn-4-yloxy and 4-methylpent-2-yn-5-yloxy, preferably prop-2-ynyloxy; 2,3-dichloroprop-2-enyl, 3,3-dichloroprop-2-enyl, 2,3,3-trichloroprop-2-enyl, 2,3-dichlorobut-2-enyl, 2-bromoprop-2-enyl, 3-bromoprop-2-enyl, 2,3-dibromoprop-2-enyl, 3,3-dibromoprop-2-enyl, 2,3,3-tribromoprop-2-enyl and 2,3-dibromobut-2-enyl; 3-chloroprop-2-enyloxy, 2,3-dichloroprop-2-enyloxy, 3,3-dichloroprop-2-enyloxy, 2,3,3-trichloroprop-2-enyloxy, 2,3-dichlorobut-2-enyloxy, 2-bromoprop-2-enyloxy, 3-bromoprop-2-enyloxy, 2,3-dibromoprop-2-enyloxy, 3,3-dibromoprop-2-enyloxy, 2,3,3-tribromoprop-2-enyloxy and 2,3-dibromobut-2-enyloxy; 3-phenylprop-2-enyloxy, 4-phenylbut-2-en-1-yloxy; 4-phenylbut-2-yn-1-yloxy; cycloheptyloxy; cyclopent-2-enyloxy, cyclopent-3-enyloxy, cyclohex-1-enyloxy,cyclohex-2-enyloxy, cyclohex-3-enyloxy, cyclohept-1-enyloxy, cyclohept-2-enyloxy, cyclohept-3-enyloxy and cyclohept-4-enyloxy; -alkylamino-C.sub.1 -C.sub.6 -alkoxy: methylamino, ethylamino, n-propylamino, 1-methylethylamino, n-butylamino, 1-methylpropylamino, 2-methylpropylamino, 1,1-dimethylethylamino, n-pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, n-hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino and 1-ethyl-2-methylpropylamino, preferably C.sub.1 -C.sub.4 -alkylamino such as methylamino, ethylamino, n-propylamino, 1-methylethylamino, n-butylamino, 1-methylpropylamino, 2-methylpropylamino and 1,1-dimethylethylamino, preferably C.sub.1 -C.sub.6 -alkylamino-C.sub.1 -C.sub.6 -alkoxy such as methylaminomethoxy, ethylaminomethoxy, n-propylaminomethoxy, (1-methylethylamino)methoxy, n-butylaminomethoxy, (1-methylpropylamino)methoxy, (2-methylpropylamino)methoxy, (1,1-dimethylethylamino)methoxy, n-pentylaminomethoxy, (1-methylbutylamino)methoxy, (2-methylbutylamino)methoxy, (3-methylbutylamino)methoxy, (2,2-dimethylpropylamino)methoxy, (1-ethylpropylamino)methoxy, n-hexylaminomethoxy, (1,1-dimethylpropylamino)methoxy, (1,2-dimethylpropylamino)methoxy, (1-methylpentylamino)methoxy, (2-methylpentylamino)methoxy, (3-methylpentylamino)methoxy, (4-methylpentylamino)methoxy, (1,1-dimethylbutylamino)methoxy, (1,2-dimethylbutylamino)methoxy, (1,3-dimethylbutylamino)methoxy, (2,2-dimethylbutylamino)methoxy, (2,3-dimethylbutylamino)methoxy, (3,3-dimethylbutylamino)methoxy, (1-ethylbutylamino)methoxy, (2-ethylbutylamino)methoxy, (1,1,2-trimethylpropylamino)methoxy, (1,2,2-trimethylpropylamino)methoxy, (1-ethyl-1-methylpropylamino)methoxy, (1-ethyl-2-methylpropylamino)methoxy, methylaminoethoxy, ethylaminoethoxy, n-propylaminoethoxy, (1-methylethylamino)ethoxy, n-butylaminoethoxy, (1-methylpropylamino)ethoxy, (2-methylpropylamino) ethoxy, (1,1-dimethylethylamino)ethoxy, n-pentylaminoethoxy, (1-methylbutylamino)ethoxy, (2-methylbutylamino)ethoxy, (3-methylbutylamino)ethoxy, (2,2-dimethylpropylamino)ethoxy, (1-ethylpropylamino)ethoxy, n-hexylaminoethoxy, (1,1-dimethylpropylamino)ethoxy, (1,2-dimethylpropylamino)ethoxy, (1-methylpentylamino)ethoxy, (2-methylpentylamino)ethoxy, (3-methylpentylamino)ethoxy, (4-methylpentylamino)ethoxy, (1,1-dimethylbutylamino)ethoxy, (1,2-dimethylbutylamino)ethoxy, 1,3-dimethylbutylamino)ethoxy, (2,2-dimethylbutylamino)ethoxy, (2,3-dimethylbutylamino)ethoxy, (3,3-dimethylbutylamino)ethoxy, (1-ethylbutylamino)ethoxy, (2-ethylbutylamino)ethoxy, (1-ethylbutylamino)ethoxy, (2-ethylbutylamino)ethoxy, (1,1,2-trimethylpropylamino)ethoxy, (1,2,2-trimethylpropylamino)ethoxy, (1-ethyl-1-methylpropylamino)ethoxy, (1-ethyl-2-methylpropylamino)ethoxy, 2-(methylamino)propoxy, 3-(methylamino)propoxy, 2-(ethylamino)propoxy; -alkyl)amino-C.sub.1 -C.sub.6 -alkoxy: N,N-dimethylamino, N,N-diethylamino, 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-methyl-ethyl)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 and N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino, preferably di-(.sub.1 -C.sub.6)-alkylamino-(C.sub.1 -C.sub.2)-alkoxy such as N,N-dimethylaminomethoxy, N,N-di-ethylaminomethoxy, N,N -dipropylaminomethoxy, N,N-di-(1-methylethyl)aminomethoxy, N,N-dibutylaminomethoxy, N,N-di-(1-methylpropyl)aminomethoxy, N,N-di-(2-methylpropyl)aminomethoxy, N,N-di-(1,1-dimethylethyl)aminomethoxy, N-ethyl-N-methylaminomethoxy, N-methyl-N-propylaminomethoxy, N-methyl-N-(1-methylethyl)aminomethoxy, N-butyl-N-methylaminomethoxy, N-methyl-N-(1-methylpropyl)aminomethoxy, N-methyl-N-(2-methylpropyl)aminomethoxy, N-(1,1-dimethylethyl)-N-methylaminomethoxy, N-ethyl-N-propylaminomethoxy, N-ethyl-N-(1-methylethyl)aminomethoxy, N-butyl-N-ethylaminomethoxy, N-ethyl-N-(1-methylpropyl)aminomethoxy, N-ethyl-N-(2-methylpropyl)aminomethoxy, N-ethyl-N-(1,1-dimethylethyl)aminomethoxy, N-(1-methylethyl)-N-propylaminomethoxy, N-butyl-N-propylaminomethoxy, N-(1-methylpropyl)-N-propylaminomethoxy, N-(2-methylpropyl)-N-propylaminomethoxy, N-(1,1-dimethylethyl)-N-propylaminomethoxy, N-butyl-N-(1-methylethyl)aminomethoxy, N-(1-methylethyl)-N-(1-methylpropyl)aminomethoxy, N-(1-methylethyl)-N-(2-methylpropyl)aminomethoxy, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminomethoxy, N-butyl-N-(1-methylpropyl)aminomethoxy, N-butyl-N-(2-methylpropyl)aminomethoxy, N-butyl-N-(1,1-dimethylethyl))aminomethoxy, N-(1-methylpropyl)-N-(2-methylpropyl)aminomethoxy, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminomethoxy, N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminomethoxy, N,N-dimethylaminoethoxy, N,N-diethylaminoethoxy, N,N-di(n-propyl)aminoethoxy, N,N-di(1-methylethyl)aminoethoxy, N,N-dibutylaminoethoxy, N,N-di(1-methylpropyl)aminoethoxy, N,N-di-(2-methylpropyl)aminoethoxy, N,N-di(1,1-dimethylethyl)aminoethoxy, N-ethyl-N-methylaminoethoxy, N-methyl-N-propylaminoethoxy, N-methyl-N-(1-methylethyl)aminoethoxy, N-butyl-N-methylaminoethoxy, N-methyl-N-(1-methylpropyl)aminoethoxy, N-methyl-N-(2-methylpropyl)aminoethoxy, N-(1,1-dimethylethyl)-N-methylaminoethoxy, N-ethyl-N-propylaminoethoxy, N-ethyl-N-(1-methylethyl)aminoethoxy, N-butyl-N-ethylaminoethoxy, N-ethyl-N-(1-methylpropyl)aminoethoxy, N-ethyl-N-(2-methylpropyl)aminoethoxy, N-ethyl-N-(1,1-dimethylethyl)aminoethoxy, N-(1-methylethyl)-N-propylaminoethoxy, N-butyl-N-propylaminoethoxy, N-(1-methylpropyl)-N-propylaminoethoxy, N-(2-methylpropyl)-N-propylaminoethoxy, N-(1,1-dimethylethyl)-N-propylaminoethoxy, N-butyl-N-(1-methylethyl)aminoethoxy, N-(1-methylethyl)-N-(1-methylpropyl)aminoethoxy, N-(1-methylethyl)-N-(2-methylpropyl)aminoethoxy, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminoethoxy, N-butyl-N-(1-methylpropyl)aminoethoxy, N-butyl-N-(2-methylpropyl)aminoethoxy, N-butyl-N-(1,1-dimethylethyl)aminoethoxy, N-(1-methylpropyl)-N-(2-methylpropyl)aminoethoxy, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminoethoxy, and N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminoethoxy; ethoxymethyl, n-propoxymethyl, (1-methylethoxy)methyl, n-butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl, n-pentoxymethyl, (1-methylbutoxy)methyl, (2-methylbutoxy)methyl, (3-methylbutoxy)methyl, (2,2-dimethylpropoxy)methyl, (1-ethylpropoxy)methyl, n-hexoxymethyl, (1,1-dimethylpropoxy)methyl, (1,2-dimethylpropoxy)methyl, (1-methylpentoxy)methyl, (2-methylpentoxy)methyl, (3-methylpentoxy)methyl, (4-methylpentoxy)methyl, (1,1-dimethylbutoxy)methyl, (1,2-dimethylbutoxy)methyl, (1,3-dimethylbutoxy)methyl, (2,2-dimethylbutoxy)methyl, (2,3-dimethylbutoxy)methyl, (3,3-dimethylbutoxy)methyl, (1-ethylbutoxy)methyl, (2-ethylbutoxy)methyl, (1,1,2-trimethylpropoxy)methyl, (1,2,2-trimethylpropoxy)methyl, (1-ethyl-1-methylpropoxy)methyl, (1-ethyl-2-methylpropoxy)methyl, methoxyethyl, ethoxyethyl, n-propoxyethyl, (1-methylethoxy)ethyl, n-butoxyethyl, (1-methylpropoxy)ethyl, (2-methylpropoxy)ethyl, (1,1-dimethylethoxy)ethyl, n-pentoxyethyl, (1-methylbutoxy)ethyl, (2-methylbutoxy)ethyl, (3-methylbutoxy)ethyl, (2,2-dimethylpropoxy)ethyl, (1-ethylpropoxy)ethyl, n-hexoxyethyl, (1,1-dimethylpropoxy)ethyl, (1,2-dimethylpropoxy)ethyl, (1-methylpentoxy)ethyl, (2-methylpentoxy)ethyl, (3-methylpentoxy)ethyl, (4-methylpentoxy)ethyl, (1,1-dimethylbutoxy)ethyl, (1,2-dimethylbutoxy)ethyl, (1,3-dimethylbutoxy)ethyl, (2,2-dimethylbutoxy)ethyl, (2,3 -dimethylbutoxy)ethyl, (3,3-dimethylbutoxy)ethyl, (1-ethylbutoxy)ethyl, (2-ethylbutoxy)ethyl, (1,1,2-trimethylpropoxy)ethyl, (1,2,2-trimethylpropoxy)ethyl, 1-(ethyl-1-methylpropoxy)ethyl, (1-ethyl-2-methylpropoxy)ethyl, 2-(methoxy)propyl, 3-(methoxy)propyl, 2-(ethoxy)propyl; ethylthiomethyl, n-propylthiomethyl, (1-methylethylthio)methyl, n-butylthiomethyl, (1-methylpropylthio)methyl, (2-methylpropylthio)methyl, (1,1-dimethylethylthio) methyl, m-pentylthiomethyl, (1-methylbutylthio) methyl, (2-methylbutylthio)methyl, (3-methylbutylthio)methyl, (2,2-dimethylpropylthio)methyl, (1-ethylpropylthio)methyl, n-hexylthiomethyl, (1,1-dimethylpropylthio)methyl, (1,2-dimethylpropylthio)methyl, (1-methylpentylthio)methyl, (2-methylpentylthio)methyl, (3-methylpentylthio, methyl, (4-methylpentylthio)methyl, (1,1-dimethylbutylthio)methyl, (1,2-dimethylbutylthio)methyl, (1,3-dimethylbutylthio)methyl, (2,2-dimethylbutylthio)methyl, (2,3-dimethylbutylthio)methyl, (3,3-dimethylbutylthio)methyl, (1-ethyl butylthio)methyl, (2-ethylbutylthio)methyl, (1,1,2-trimethylpropylthio)methyl, (1,2,2-trimethylpropylthio)methyl, (1-ethyl-1-methylpropylthio)methyl, (1-ethyl-2-methylpropylthio)methyl, methylthioethyl, ethylthioethyl, n-propylthioethyl, (1-methylethylthio)ethyl, n-butylthioethyl, (1-methylpropylthio)ethyl, (2-methylpropylthio)ethyl, (1,1-dimethylethylthio)ethyl, n-pentylthioethyl, (1-methylbutylthio)ethyl, (2-methylbutylthio)ethyl, (3-methylbutylthio)ethyl, (2,2-dimethylpropylthio)ethyl, (1-ethylpropylthio)ethyl, n-hexylthioethyl, (1,1-dimethylpropylthio)ethyl, (1,2-dimethylpropylthio)ethyl, (1-methylpentylthio)ethyl, (2-methylpentylthio)ethyl, (3-methylpentylthio)ethyl, (4-methylpentylthio)ethyl, (1,1-dimethylbutylthio)ethyl, (1,2-dimethylbutylthio)ethyl, (1,3-dimethylbutylthio)ethyl, (2,2-dimethylbutylthio)ethyl, (2,3-dimethylbutylthio)ethyl, (3,3-dimethylbutylthio)ethyl, (1-ethylbutylthio)ethyl, (2- ethylbutylthio)ethyl, (1,1,2-trimethylpropylthio)ethyl, (1,2,2-trimethylpropylthio)ethyl, (1-ethyl-1-methylpropylthio)ethyl, (1-ethyl-2-methylpropylthio)ethyl, 2-(methylthio)propyl, 3-(methylthio)propyl, 2-(ethylthio)propyl; -alkoximino-C.sub.1 -C.sub.6 -alkyl: methoximino, ethoximino, n-propoximino, 1-methylethoximino, n-butoximino, 1-methylpropoximino, 2-methylpropoximino, 1,1-dimethylethoximino, n-pentoximino, 1-methylbutoximino, 2-methylbutoximino, 3-methylbutoximino, 1,1-dimethylpropoximino, 1,2-dimethylpropoximino, 2,2-dimethylpropoximino, 1-ethylpropoximino, n-hexoximino, 1-methylpentoximino, 2-methylpentoximino, 3-methylpentoximino, 4-methylpentoximino, 1,1-dimethylbutoximino, 1,2-dimethylbutoximino, 1,3-dimethylbutoximino, 2,2-dimethylbutoximino, 2,3-dimethylbutoximino, 3,3-dimethylbutoximino, 1-ethylbutoximino, 2-ethylbutoximino, 1,1,2-trimethylpropoximino, 1,2,2-trimethylpropoximino, 1-ethyl-1-methylpropoximino and 1-ethyl-2-methylpropoximino, preferably methoximinomethyl, ethoximinomethyl, n-propoximinomethyl, (1-methylethoximino)methyl, n-butoximinomethyl, (1-methylpropoximino)methyl, (2-methylpropoximino)methyl, (1,1-dimethylethoximino)methyl, n-pentoximinomethyl, (1-methylbutoximino)methyl, (2-methylbutoximino)methyl, (3-methylbutoximino)methyl, 2,2-dimethylpropoximino)methyl, (1-ethylpropoximino)methyl, n-hexoximinomethyl, (1,1-dimethylpropoximino)methyl, (1,2-dimethylpropoximino)methyl, (1-methylpentoximino)methyl, (2-methylpentoximino)methyl, (3-methylpentoximino)methyl, (4-methylpentoximino)methyl, (1,1-dimethylbutoximino)methyl, (1,2-dimethylbutoximino)methyl, (1,3-dimethylbutoximino)methyl, (2,2-dimethylbutoximino)methyl, (2,3-dimethylbutoximino)methyl, (3,3-dimethylbutoximino)methyl, (1-ethylbutoximino)methyl, (2-ethylbutoximino)methyl, (1,1,2-trimethylpropoximino)methyl, (1,2,2-trimethylpropoximino)methyl, (1-ethyl-1-methylpropoximino)methyl, (1-ethyl-2-methylpropoximino)methyl, methoximinoethyl, ethoximinoethyl, n-propoximinoethyl, (1-methylethoximino)ethyl, n-butoximinoethyl, (1-methylpropoximino)ethyl, (2-methylpropoximino)ethyl, (1,1-dimethylethoximino)ethyl, n-pentoximinoethyl, (1-methylbutoximino)ethyl, (2-methylbutoximino)ethyl, (3-methylbutoximino)ethyl, (2,2-dimethylpropoximino)ethyl, (1-ethylpropoximino)ethyl, n-hexoximino-ethyl, (1,1-dimethylpropoximino)ethyl, (1,2-dimethylpropoximino)ethyl, (1-methylpentoximino)ethyl, (2-methylpentoximino)ethyl, (3-methylpentoximino)ethyl, (4-methylpentoximino)ethyl, (1,1-dimethylbutoximino)ethyl, (1,2-dimethylbutoximino)ethyl, (1,3-dimethylbutoximino)ethyl, (2,2-dimethylbutoximino)ethyl, (2,3-dimethylbutoximino)ethyl, (3,3-dimethylbutoximino)ethyl, (1-ethylbutoximino)ethyl, (2-ethylbutoximino)ethyl, (1,1,2-trimethylpropoximino)ethyl, (1,2,2-trimethylpropoximino)ethyl, (1-ethyl-1-methylpropoximino)ethyl, (1-ethyl-2-methylpropoximino)ethyl, 2-(methoximino)propyl, 3-(methoximino)propyl, 2-(ethoximino)propyl, preferably C.sub.1 -C.sub.6 -alkoximino-C.sub.1 -C.sub.2 -alkyl such as methoximinomethyl, ethoximinomethyl, 2-methoximinoethyl and 2-ethoximinoethyl; ethoxymethoxy, n-propoxymethoxy, (1-methylethoxy)methoxy, n-butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, (1,1-dimethylethoxy)methoxy, n-pentoxymethoxy, (1-methylbutoxy)methoxy, (2-methylbutoxy)methoxy, (3-methylbutoxy)methoxy, (2,2-dimethylpropoxy)methoxy, (1-ethylpropoxy)methoxy, n-hexoxymethoxy, (1,1-dimethylpropoxy)methoxy, (1,2-dimethylpropoxy)methoxy, (1-methylpentoxy)methoxy, (2-methylpentoxy)methoxy, (3-methylpentoxy)methoxy, (4-methylpentoxy)methoxy, (1,1-dimethylbutoxy)methoxy, (1,2-dimethylbutoxy)methoxy, (1,3-dimethylbutoxy)methoxy, (2,2-dimethylbutoxy)methoxy, (2,3-dimethylbutoxy)methoxy, (3,3-dimethylbutoxy)methoxy, (1-ethylbutoxy)methoxy, (2-ethylbutoxy)methoxy, (1,1,2-trimethylpropoxy)methoxy, (1,2,2-trimethylpropoxy)methoxy, (1-ethyl-1-methylpropoxy)methoxy, (1-ethyl-2-methylpropoxy)methoxy, methoxyethoxy, ethoxyethoxy, n-propoxyethoxy, (1-methylethoxy)ethoxy, n-butoxyethoxy, (1-methylpropoxy)ethoxy, (2-methylpropoxy)ethoxy, (1,1-dimethylethoxy)ethoxy, n-pentoxyethoxy, (1-methylbutoxy)ethoxy, (2-methylbutoxy)ethoxy, (3-methylbutoxy)ethoxy, (2,2-dimethylpropoxy)ethoxy, (1-ethylpropoxy)ethoxy, n-hexoxyethoxy, (1,1-dimethylpropoxy)ethoxy, (1,2-dimethylpropoxy)ethoxy, (1-methylpentoxy)ethoxy, (2methylpentoxy)ethoxy, (3-methylpentoxy)ethoxy, (4methylpentoxy)ethoxy, (1,1-dimethylbutoxy)ethoxy, (1,2-dimethylbutoxy)ethoxy, (1,3-dimethylbutoxy)ethoxy, (2,2-dimethylbutoxy)ethoxy, (2,3-dimethylbutoxy)ethoxy, (3,3-dimethylbutoxy)ethoxy, (1-ethylbutoxy)ethoxy, (2-ethylbutoxy)ethoxy, (1,1,2-trimethylpropoxy)ethoxy, (1,2,2-trimethylpropoxy)ethoxy, (1-ethyl-1-methylpropoxy)ethoxy, (1-ethyl-2-methylpropoxy)ethoxy, 2-(methoxy)propoxy, 3-(methoxy)propoxy, 2-(ethoxy)propoxy, preferably C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkoxy such as methoxymethoxy, ethoxymethoxy, 2-methoxyethyl and 2-ethoxyethyl; ethylthiomethoxy, n-propylthiomethoxy, (1-methylethylthio)methoxy, n-butylthiomethoxy, (1-methylpropylthio)methoxy, (2-methylpropylthio)methoxy, (1,1-dimethylethylthio)methoxy, n-pentylthiomethoxy, (1-methylbutylthio)methoxy, (2-methylbutylthio)methoxy, (3-methylbutylthio)methoxy, (2,2-dimethylpropylthio)methoxy, (1-ethylpropylthio)methoxy, n-hexylthiomethoxy, (1,1-dimethylpropylthio)methoxy, (1,2-dimethylpropylthio)methoxy, (1-methylpentylthio)methoxy, (2-methylpentylthio)methoxy, (3-methylpentylthio)methoxy, (4-methylpentylthio)methoxy, (1,1-dimethylbutylthio)methoxy, (1,2-dimethylbutylthio)methoxy, (1,3-dimethylbutylthio)methoxy, (2,2-dimethylbutylthio)methoxy, (2,3-dimethylbutylthio)methoxy, (3,3-dimethylbutylthio)methoxy, (1-ethylbutylthio)methyl, (2-ethylbutylthio)methoxy, (1,1,2-trimethylpropylthio)methoxy, (1,2,2-trimethylpropylthio)methoxy, (1-ethyl-1-methylpropylthio)methoxy, (1-ethyl-2-methylpropylthio)methoxy, methylthioethoxy, ethylthioethoxy, n-propylthioethoxy, (1-methylethylthio)ethoxy, n-butylthioethoxy, (1-methylpropylthio)ethoxy, (2-methylpropylthio)ethoxy, (1,1-dimethylethylthio)ethoxy, n-pentylthioethoxy, (1-methylbutylthio)ethoxy, (2-methylbutylthio)ethoxy, (3-methylbutylthio)ethoxy, (2,2-dimethylpropylthio)ethoxy, (1-ethylpropylthio)ethoxy, n-hexylthioethoxy, (1,1-dimethylpropylthio)ethoxy, (1,2-dimethylpropylthio)ethoxy, (1-methylpentylthio)ethoxy, (2-methylpentylthio)ethoxy, (3-methylpentylthio)ethoxy, (4-methylpentylthio)ethoxy, (1,1-dimethylbutylthio)ethoxy, (1,2-dimethylbutylthio)ethoxy, (1,3-dimethylbutylthio)ethoxy, (2,2-dimethylbutylthio)ethoxy, (2,3-dimethylbutylthio)ethoxy, (3,3-dimethylbutylthio)ethoxy, (1-ethylbutylthio)ethoxy, (2-ethylbutylthio)ethoxy, (1,1,2-trimethylpropylthio)ethoxy, (1,2,2-trimethylpropylthio)ethoxy, (1-ethyl-1-methylpropylthio)ethoxy, (1-ethyl-2-methylpropylthio)ethoxy, 2-(methylthio)propoxy, 3-(methylthio)propoxy, 2-(ethylthio)propoxy, preferably C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.2 -alkoxy such as methylthiomethoxy, ethylthiomethoxy, 2-methylthioethyl and 2-ethylthioethyl; n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1,1-dimethylethylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl and 1-ethyl-2-methylpropoxycarbonyl, preferably C.sub.1 -C.sub.4 -alkylcarbonyl such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1,1-dimethylethylcarbonyl; n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1,1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1,2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n-hexylcarbonyloxy, 1-methylpentylcarbonyloxy, 2-methylpentylcarbonyloxy, 3-methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, 1,1-dimethylbutylcarbonyloxy, 1,2-dimethylbutylcarbonyloxy, 1,3-dimethylbutylcarbonyloxy, 2,2-dimethylbutylcarbonyloxy, 2,3-dimethylbutylcarbonyloxy, 3,3-dimethylbutylcarbonyloxy, 1-ethylbutylcarbonyloxy, 2-ethylbutylcarbonyloxy, 1,1,2-trimethylpropylcarbonyloxy, 1,2,2-trimethylpropylcarbonyloxy, 1-ethyl-1-methylpropylcarbonyloxy and 1-ethyl-2-methylpropoxycarbonyloxy, preferably C.sub.1 -C.sub.4 -alkylcarbonyloxy such as methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, and 1,1-dimethylethylcarbonyloxy; moieties in the radicals C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.2 -C.sub.6 -alkenyl and C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.2 -C.sub.6 -alkoxy:methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl, 1,1-dimethylethoxycarbonyl, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl and 1-ethyl-2-methylpropylcarbonyl, preferably such as C.sub.1 -C.sub.4 -alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl and 1,1-dimethylethoxycarbonyl; methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycarbonylmethyl, (1-methylethoxycarbonyl)methyl, n-butoxycarbonylmethyl, (1-methylpropoxycarbonyl)methyl, (2-methylpropoxycarbonyl)methyl, (1,1-dimethylethoxycarbonyl)methyl, n-pentoxycarbonylmethyl, (1-methylbutoxycarbonyl)methyl, (2-methylbutoxycarbonyl)methyl, (3-methylbutoxycarbonyl)methyl, (1,1-dimethylpropoxycarbonyl)methyl, (1,2-dimethylpropoxycarbonyl)methyl, (2,2-dimethylpropoxycarbonyl)methyl, (1-ethylpropoxycarbonyl)methyl, n-hexoxycarbonylmethyl, (1-methylpentoxycarbonyl)methyl, (2-methylpentoxycarbonyl)methyl, (3-methylpentoxycarbonyl)methyl, (4-methylpentoxycarbonyl)methyl, (1,1-dimethylbutoxycarbonyl)methyl, (1,2-dimethylbutoxycarbonyl)methyl, (1,3-dimethylbutoxycarbonyl)methyl, (2,2-dimethylbutoxycarbonyl)methyl, (2,3-dimethylbutoxycarbonyl)methyl, (3,3-dimethylbutoxycarbonyl)methyl, (1-ethylbutoxycarbonyl)methyl, (2-ethylbutoxycarbonyl)methyl, (1,1,2-trimethylpropoxycarbonyl)methyl, (1,2,2-trimethylpropoxycarbonyl)methyl, (1-ethyl-1-methylpropoxycarbonyl)methyl, (1-ethyl-2-methylpropylcarbonyl)methyl, methoxycarbonylethyl, ethoxycarbonylethyl, n-propoxycarbonylethyl, (1-methylethoxycarbonyl)ethyl, n-butoxycarbonylethyl, (1-methylpropoxycarbonyl)ethyl, (2-methylpropoxycarbonyl)ethyl, (1,1-dimethylethoxycarbonyl)ethyl, n-pentoxycarbonylethyl, (1-methylbutoxycarbonyl)ethyl, (2-methylbutoxycarbonyl)ethyl, (3-methylbutoxycarbonyl)ethyl, (1,1-dimethylpropoxycarbonyl)ethyl, (1,2-dimethylpropoxycarbonyl)ethyl, (2,2-dimethylpropoxycarbonyl)ethyl, (1-ethylpropoxycarbonyl)ethyl, n-hexoxycarbonylethyl, (1-methylpentoxycarbonyl)ethyl, (2-methylpentoxycarbonyl)ethyl, (3-methylpentoxycarbonyl)ethyl, (4-methylpentoxycarbonyl)ethyl, (1,1-dimethylbutoxycarbonyl)ethyl, (1,2-dimethylbutoxycarbonyl)ethyl, (1,3-dimethylbutoxycarbonyl)ethyl, (2,2)dimethylbutoxycarbonyl)ethyl, (2,3-dimethylbutoxycarbonyl)ethyl, (3,3-dimethylbutoxycarbonyl)ethyl, (1-ethylbutoxycarbonyl)ethyl, (2-ethylbutoxycarbonyl)ethyl, (1,1,2-trimethylpropoxycarbonyl)ethyl, (1,2,2-trimethylpropoxycarbonyl)ethyl, (1-ethyl-1-methylpropoxycarbonyl)ethyl, (1-ethyl-2-methylpropylcarbonyl)ethyl, 3-(methoxycarbonyl)propyl, 2-(methoxycarbonyl)propyl and 2-(ethoxycarbonyl)propyl, preferably C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.2 -alkyl such as methoxycarbonylmethyl, ethoxycarbonylmethyl, 2-methoxycarbonylethyl and 2-ethoxycarbonylethyl; heterocyclyl-C.sub.1 -C.sub.6 -alkyl group, where the heterocycle can in each case be saturated or partially or completely unsaturated and can carry one to four heteroatoms: tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, 1,2,4-oxadiazolidinyl, 1,3,4-oxadiazolidinyl, 1,2,4-thiadiazolidinyl, 1,3,4- thiadiazolidinyl, 1,2,4-triazolidinyl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofuryl, 2,4-dihydrofuryl, 2,3-dihydrothienyl, 2,4-dihydrothienyl, 2,3-pyrrolin- 2-yl, 2,4-pyrrolinyl, 2,3-isoxazolinyl, 3,4-isoxazolinyl, 4,5-isoxazolinyl, 2,3-isothiazolinyl, 3,4-isothiazolinyl, 4,5-isothiazolinyl, 2,3-dihydropyrazolyl, 3,4-dihydropyrazolyl, 4,5-dihydropyrazol-1-yl, 2,3-dihydrooxazolyl, 3,4-dihydrooxazolyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl and 1,2,4-tetrahydrotriazin-3-yl; furanyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-triazolyl, 1,3,4-triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, dihydropyran-2-yl, dihydropyran-3-yl, dihydropyran-4-yl, dihydrothiopyran-2-yl, dihydrothiopyran-3-yl, dihydrothiopyran-4-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, ##STR7##

The substituted isoindolones I can be present in the form of their agriculturally utilizable salts, the type of salt generally being unimportant. Suitable salts are usually the salts of those bases which do not have an adverse effect on the herbicidal action of I.

Suitable basic salts are particularly those of the alkali metals, preferably the sodium and potassium salts, those of the alkaline earth metals, preferably calcium, magnesium and barium salts, and those of the transition metals, preferably manganese, copper, zinc and iron salts, as well as the ammonium salts which can carry one to three C.sub.1 -C.sub.4 -alkyl or hydroxy-C.sub.1 -C.sub.4 -alkyl substituents and/or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium and trimethyl(2-hydroxyethyl)ammonium salts, the phosphonium salts, the sulfonium salts, preferably tri-(C.sub.1 -C.sub.4)-alkylsulfonium salts, and the sulfoxonium salts, preferably tri-(C.sub.1 -C.sub.4)-alkylsulfoxonium salts.

In respect of the use of the isoindolones I of the invention as compounds which have herbicidal and defoliant/desiccant activity, the variables preferably have the following meanings: group 1.01-1.66 (Table 1) or 2), (Table 6), group 12.01-12.17 (Table 12), group 17.01-17.12 (Table 13) or (Table 14),

where the substituents R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 can be combined with one another in any desired manner, with the proviso that either R.sup.1 and R.sup.2 are hydrogen and R.sup.4 is simultaneously fluorine, or R.sup.1 and R.sup.2 are hydrogen. ______________________________________ No.              R.sup.1, R.sup.2 ______________________________________ 1.01             H 1.02             CH.sub.3 1.03             C.sub.2 H.sub.5 1.04             n-C.sub.3 H.sub.7 1.05             CH(CH.sub.3).sub.2 1.06             n-C.sub.4 H.sub.9 1.07             i-C.sub.4 H.sub.9 1.08             s-C.sub.4 H.sub.9 1.09             C(CH.sub.3).sub.3 1.10             n-C.sub.5 H.sub.11 1.11             n-C.sub.6 H.sub.13 1.12             CH.sub.2 --CH.dbd.CH.sub.2 1.13             CH.sub.2 --CH.dbd.CHCH.sub.3 1.14             CH.sub.2 --C.tbd.CH 1.15             CH.sub.2 C.tbd.C--SiCH.sub.3 1.16             CH.sub.2 OCH.sub.3 1.17             (CH.sub.2).sub.3 --OCH.sub.3 1.18             (CH.sub.2).sub.3 --OC.sub.2 H.sub.5 1.19             CN 1.20             (CH).sub.2 --CN 1.21             COOCH.sub.3 1.22             COOC.sub.2 H.sub.5 1.23             COO(n-C.sub.3 H.sub.7) 1.24             COO--CH(CH.sub.3).sub.2 1.25             COO(n-C.sub.4 H.sub.9) 1.26             COO(i-C.sub.4 H.sub.9) 1.27             COO(s-C.sub.4 H.sub.9) 1.28             COO--C(CH.sub.3).sub.3 1.29             CHO 1.30             COCH.sub.3 1.31             COC.sub.2 H.sub.5 1.32             CO--CH(CH.sub.3).sub.2 1.33             CO-phenyl 1.34             CO-(4-Cl-phenyl) 1.35             CO-(4F-phenyl) 1.36             CO-(2,4-Cl.sub.2 -phenyl) 1.37             CH.sub.2 --COOCH.sub.3 1.38             (CH.sub.2).sub.2 --COOCH.sub.3 1.39             (CH.sub.2).sub.4 --COOC.sub.2 H.sub.5 1.40             CH.dbd.CH--COOCH.sub.3 1.41             CH.dbd.CH--COOC.sub.2 H.sub.5 1.42             Cyclopropyl 1.43             Cyclobutyl 1.44             Cyclopentyl 1.45             Cyclohexyl 1.46             Cycloheptyl 1.47             Cyclooctyl 1.48             (CH.sub.2).sub.3 --Cl 1.49             (CH.sub.2).sub.3 --F 1.50             Phenyl 1.51             4-Cl-phenyl 1.52             4-F-phenyl 1.53             3-F-phenyl 1.54             2-F-phenyl 1.55             2-Cl-phenyl 1.56             3-Cl-phenyl 1.57             4-CH.sub.3 -phenyl 1.58             4-Br-phenyl 1.59             4-OCH.sub.3 -phenyl 1.60             4-NO.sub.2 -phenyl 1.61             3-CF.sub.3 -phenyl 1.62             4-CF.sub.3 -phenyl 1.63             2-CF.sub.3 -phenyl 1.64             2,4-Cl.sub.2 -phenyl 1.65             3,4-Cl.sub.2 -phenyl 1.66             2-Cl,4-F-phenyl ______________________________________ ______________________________________ No.  R.sup.1, R.sup.2 ______________________________________ 2.01 --(CH.sub.2).sub.2 -- 2.02 --(CH.sub.2).sub.4 -- 2.03 --(CH.sub.2).sub.5 -- 2.04 --(CH.sub.2).sub.6 -- ______________________________________ ______________________________________ No.                 R.sup.3 ______________________________________ 3.01                H 3.02                CH.sub.3 3.03                C.sub.2 H.sub.5 3.04                n-C.sub.3 H.sub.7 3.05                i-C.sub.3 H.sub.7 3.06                n-C.sub.4 H.sub.9 3.07                i-C.sub.4 H.sub.9 3.08                s-C.sub.4 H.sub.9 3.09                C(CH.sub.3).sub.3 3.10                n-C.sub.5 H.sub.11 3.11                n-C.sub.6 H.sub.13 ______________________________________ ______________________________________ No.                   R.sup.4 ______________________________________ 4.01                  H 4.02                  F 4.03                  Cl 4.04                  Br 4.05                  I ______________________________________ ______________________________________ No.                   R.sup.5 ______________________________________ 5.01                  F 5.02                  Cl 5.03                  Br 5.04                  I 5.05                  CN 5.06                  NO.sub.2 5.07                  CF.sub.3 5.08                  H ______________________________________ ______________________________________ No.       R.sup.5, R.sup.6 ______________________________________ 56.01     --O--CH.sub.2 --CO--N(CH.sub.3)-- 56.02     --O--CH.sub.2 --CO--NH-- 56.03     --O--CH.sub.2 CO--N(CH.sub.2 C.tbd.CH)-- 56.04     --OCH(CH.sub.3)--CO--N(CH.sub.2 C.tbd.CH) 56.05     --O--CH(CH.sub.3)--CO--N(i-C.sub.3 H.sub.7)-- 56.06     --O--CH.sub.2 --CO--N(i-C.sub.3 H.sub.7)-- 56.07     --S--CH.sub.2 --CO--N(CH.sub.2 C.tbd.CH)-- 56.08     --CH.sub.2 --CH.sub.2 --CO--N(CH.sub.2 C.tbd.CH)-- 56.09     --O--CO--N(CH.sub.3)-- 56.10     --O--CO--N(CH.sub.2 C.tbd.CH)-- 56.11     --S--CO--N(CH.sub.3)-- 56.12     --S--CO--N(CH.sub.2 C.tbd.CH)-- 56.13     --N.dbd.CH--CO--N(CH.sub.2 C.tbd.CH)-- 56.14     --N.dbd.CH--CO--N(CH.sub.3)-- 56.15     --N.dbd.CH--CO--N(i-C.sub.3 H.sub.7) 56.16     --O--(CH.sub.2).sub.2 --C(.dbd.N--OCH.sub.3)-- 56.17     --O--(CH.sub.2).sub.2 --C(.dbd.N--OC.sub.2 H.sub.5)-- 56.18     --O--CO--CH.sub.2 --N(CH.sub.2 C.tbd.CH)-- 56.19     --O--CO--CH(CH.sub.3)--N--(CH.sub.2 C.tbd.CH)-- 56.20     --O--CO--CH.sub.2 --N(i-C.sub.3 H.sub.7)-- 56.21     --O--CO--CH(CH.sub.3 --N(i-C.sub.3 H.sub.7)-- 56.22     --CH.dbd.CH--N--(CH.sub.2 C.tbd.CH)-- 56.23     --CH.dbd.CH--N(iC.sub.3 H.sub.7)-- 56.24     --CH.dbd.C(CH.sub.3)--N(CH.sub.2 C.tbd.CH)-- 56.25     --C(CH.sub.3).dbd.CH--N(CH.sub.2 C.tbd.CH)-- 56.26     --S--C(O-iC.sub.3 H.sub.7).dbd.N-- 56.27     --S--C(OCH.sub.2 C.tbd.CH).dbd.N-- 56.28     --O--CH.sub.2 --CH.sub.2 --N(CH.sub.2 C.tbd.CH)-- 56.29     --O--CH.sub.2 --CH(CH.sub.3)--N(CH.sub.2 C.tbd.CH)-- 56.30     --O--CH.sub.2 --CH(CF.sub.3)--N(CH.sub.2 C.tbd.CH)-- 56.31     --S--CH.sub.2 --CO--N(CH.sub.3)-- ______________________________________ ______________________________________ No.            R.sup.6 ______________________________________ 6.01           A-CO--B 6.02           C(R.sup.10).dbd.O 6.03           C(R.sup.10).dbd.S 6.04           C(R.sup.10).dbd.N(R.sup.11) 6.05           C(X.sup.1 R.sup.17)(X.sup.2 R.sup.18)R.sup.10 6.06           P(R.sup.12)(R.sup.13).dbd.O 6.07           CHR.sup.10 --CHR.sup.11 --CO--B ______________________________________ ______________________________________ No.            A ______________________________________ A.01           --CH.dbd.CH-- A.02           --CH.dbd.CH--CH.sub.2 -- A.03           --CH.dbd.CCl-- A.04           --CH.dbd.CBr-- A.05           --CH.dbd.CI-- A.06           --CH.dbd.C(CH.sub.3)-- A.07           --CH.dbd.C(C.sub.2 H.sub.5)-- A.08           --CH.dbd.C(CN)-- A.09           --CH.dbd.C(COOCH.sub.3)-- A.10           --CH.dbd.C(COOC.sub.2 H.sub.5)-- A.11           --CH.dbd.C(OCOCH.sub.3)-- A.12           --CH.dbd.C(COCH.sub.3)-- A.13           --C.tbd.C-- A.14           --C.tbd.C--CH.sub.2 -- A.15           --C.tbd.C--CH.sub.2 --CH.sub.2 -- A.16           --C.tbd.C--CH(CH.sub.3)-- A.17           --C(CH.sub.3).dbd.CH-- A.18           --C(CH.sub.3).dbd.CCl A.19           --C(CH.sub.3).dbd.CBr-- A.20           --C(CH.sub.3).dbd.C(CH.sub.3)-- A.21           --C(CH.sub.3).dbd.C(CN)-- A.22           --CH.dbd.CF-- A.23           --CH.sub.2 -- A.24           --CH.sub.2 --CH.sub.2 A.25           --CH.sub.2 CH(CN)-- A.26           --CH.sub.2 --CHCl-- A.27           --CH.sub.2 --CHBr-- A.28           --CH.sub.2 --CHF-- A.29           --CH.sub.2 --CH(CH.sub.3)-- A.30           --CH.sub.2 CH(COOCH.sub.3)-- A.31           --CH.sub.2 --CH(COCH.sub.3)-- A.32           --(CH.sub.2).sub.3 -- A.33           --(CH.sub.2).sub.4 -- ______________________________________ ______________________________________ No.             B ______________________________________ B.01            H B.02            OH B.03            OCH.sub.3 B.04            OC.sub.2 H.sub.5 B.05            O-n-C.sub.3 H.sub.7 B.06            O-i-C.sub.3 H.sub.7 B.07            O-n-C.sub.3 H.sub.9 B.08            O-i-C.sub.4 H.sub.9 B.09            O-s-C.sub.4 H.sub.9 B.10            O-tert.-C.sub.4 H.sub.9 B.11            O-n-C.sub.5 H.sub.11 B.12            O-n-C.sub.6 H.sub.13 B.13            O--CH.sub.2 CH.dbd.CH.sub.2 B.14            O--CH(CH.sub.3)CH.dbd.CH.sub.2 B.15            O--CH--CH.dbd.CH--CH.sub.2 B.16            O--CH.sub.2 --C.tbd.CH B.17            O--CH(CH.sub.3)--C.tbd.CH B.18            O--CH.sub.2 --C.tbd.C--CH.sub.3 B.19            O-cyclopropyl B.20            O-cyclobutyl B.21            O-cyclopentyl B.22            O-cyclohexyl B.23            O--CH.sub.2 --CF.sub.3 B.24            O--CH.sub.2 CCl.sub.3 B.25            O--(CH.sub.2).sub.3 --Br B.26            O-phenyl B.27            O-(2-F-phenyl) B.28            O-(2-Cl-phenyl) B.29            O-(2-Br-phenyl) B.30            O-(3-F-phenyl) B.31            O-(3-Cl-phenyl) B.32            O-(3-Br-phenyl) B.33            O-(4-F-phenyl) B.34            O-(4-Cl-phenyl) B.35            O-(4-Br-phenyl) B.36            O-(4-OCH.sub.3 -phenyl) B.37            O-(4-CN-phenyl) B.38            O-(4-COOCH.sub.3 -phenyl) B.39            O-(CH.sub.3 -phenyl) B.40            O-(2,4-Cl.sub.2 -phenyl) B.41            O-(2,4-(CH.sub.3).sub.2 -phenyl) B.42            O-CH.sub.2 CN B.43            O-CH.sub.2 CH.dbd.CCl.sub.2 B.44            O-CH.sub.2 CH.dbd.CHCl B.45            O-CH.sub.2 OCH.sub.3 B.46            O--CH.sub.2 OC.sub.2 H.sub.5 B.47            O--C.sub.2 H.sub.4 OCH.sub.3 B.48            O--C.sub.2 H.sub.4 OC.sub.2 H.sub.5 B.49            O--CH(CH.sub.3)--OCH.sub.3 B.50            O--CH(CH.sub.3)--OC.sub.2 H.sub.5 B.51            OCH.sub.2 C.dbd.NOCH.sub.3 B.52            O--C.sub.2 H.sub.5 C.dbd.NOCH.sub.3 B.53            O--CH.sub.2 C.dbd.NOC.sub.2 H.sub.5 B.54            O--C(O)CH.sub.3 B.55            O--C(O)C.sub.2 H.sub.5 B.56            O--C.sub.2 H.sub.4 C.dbd.NOC.sub.2 H.sub.5 B.57            SCH.sub.3 B.58            SC.sub.2 H.sub.5 B.59            S-n-C.sub.3 H.sub.7 B.60            S-i-C.sub.3 H.sub.7 B.61            S--CH.sub.2 CH.dbd.CH.sub.2 B.62            S--CH.sub.2 C.tbd.CH B.63            S-phenyl B.64            S-CH.sub.2 CN B.65            S--CH.sub.2 OCH.sub.3 B.66            CH.sub.3 B.67            C.sub.2 H.sub.7 B.68            n-C.sub.3 H.sub.7 B.69            i-C.sub.3 H.sub.7 B.70            n-C.sub.4 H.sub.9 B.71            i-C.sub.4 H.sub.9 B.72            s-C.sub.4 H.sub.9 B.73            tert.-C.sub.4 H.sub.9 B.74            n-C.sub.5 H.sub.11 B.75            n-C.sub.6 H.sub.13 B.76            CH.sub.2 CH.dbd.CH.sub.2 B.77            CH.sub.2 C.tbd.CH B.78            CH(CH.sub.3)CH.dbd.CH.sub.2 B.79            CH(CH.sub.3)C.tbd.CH B.80            CH.sub.2 Cl B.81            CH.sub.2 Br B.82            CHCl.sub.2 B.83            CF.sub.3 B.84            Cyclopropyl B.85            Cyclobutyl B.86            Cyclopentyl B.87            CyclohexyL B.88            Phenyl B.89            2-F-phenyl B.90            3-F-phenyl B.91            4-F-phenyl B.92            2-Cl-phenyl B.93            4-Cl-phenyl B.94            2,4-Cl.sub.2 -phenyl B.95            CH.sub.2 --OCH.sub.3 B.96            CH(OCH.sub.3).sub.2 B.97            CH.sub.2 --SCH.sub.3 B.98            NH.sub.2 B.99            NHCH.sub.3 B.100           NH-n-C.sub.3 H.sub.7 B.101           NH-i-C.sub.3 H.sub.7 B.102           NH-n-C.sub.4 H.sub.9 B.103           N(CH.sub.3).sub.2 B.104           N(C.sub.2 H.sub.5).sub.2 B.105           N(CH.sub.3)C.sub.2 H.sub.5 B.106           N(n-C.sub.3 H.sub.7).sub.2 B.107           NH--CH.sub.2 CH.dbd.CH.sub.2 B.108           NH--CH(CH.sub.3)--CH.dbd.CH.sub.2 B.109           NH--CH.sub.2 --C.tbd.CH B.110           NH--CH(CH.sub.3)--C.tbd.CH B.111           N(CH.sub.3)--CH.sub.2 CH.dbd.CH B.112           N(CH.sub.3)--CH.sub.2 C.tbd.CH B.113           NH-cyclopropyl B.114           NH-cyclobutyl B.115           NH-cyclopentyl B.116           NH-cyclohexyl B.117           N(CH.sub.3)-cyclohexyl B.118           N(C.sub.2 H.sub.5)-cyclohexyl B.119           NH-COCH.sub.3 B.120           NH--COC.sub.2 H.sub.5 B.121           NH--COOCH.sub.3 B.122           NH--CH.sub.2 OCH.sub.3 B.123           NH--(CH.sub.2).sub.2 CCH.sub.3 B.124           N-piperidinyl B.125           N-pyrrolidinyl B.126           N-morpholino B.127           N-piperazinyl B.128           NH-phenyl B.129           NH-(2-CH.sub.3 -phenyl) B.130           NH-(2-F-phenyl) B.131           NH-(4-F-phenyl) B.132           NH-(2-Cl-phenyl) B.133           NH-(4-Cl-phenyl) B.134           NH-(2,4-Cl.sub.2 -phenyl) B.135           O--CO--OCH.sub.3 B.136           O--CO--OC.sub.2 H.sub.5 B.137           O--CH.sub.2 --COOCH.sub.3 B.138           O--CH(CH.sub.3)--COOCH.sub.3 ______________________________________ ______________________________________ No.               R.sup.10 ______________________________________ 10.01             H 10.02             CH.sub.3 10.03             C.sub.2 H.sub.5 10.04             n-C.sub.3 H.sub.7 10.05             i-C.sub.3 H.sub.7 10.06             n-C.sub.4 H.sub.9 10.07             i-C.sub.4 H.sub.9 10.08             s-C.sub.4 H.sub.9 10.09             tert.-C.sub.4 H.sub.9 10.10             n-C.sub.5 H.sub.11 10.11             n-C.sub.6 H.sub.13 10.12             CH.sub.2 --CH.dbd.CH.sub.2 10.13             CH.sub.2 --C.tbd.CH 10.14             CF.sub.3 10.15             CCl.sub.3 10.16             Cyclopropyl 10.17             Cyclobutyl 10.18             Cyclopentyl 10.19             Cyclohexyl 10.20             CN 10.21             CO--OCH.sub.3 10.22             CO--OC.sub.2 H.sub.5 ______________________________________ ______________________________________ No.          R.sup.11 ______________________________________ 11.001       H 11.002       CH.sub.3 11.003       C.sub.2 H.sub.5 11.004       n-C.sub.3 H.sub.7 11.005       CH(CH.sub.3).sub.2 11.006       n-C.sub.4 H.sub.9 11.007       n-C.sub.5 H.sub.11 11.008       n-C.sub.6 H.sub.13 11.009       CH.sub.2 CH.dbd.CH.sub.2 11.010       CH(CH.sub.3)--CH.dbd.CH.sub.2 11.011       CH.sub.2 --CH.dbd.CH--CH.sub.2 11.012       CH.sub.2 --C.tbd.CH 11.013       CH(CH.sub.3)--C.tbd.CH 11.014       CH.sub.2 --C.tbd.C--CH.sub.3 11.015       Cyclopropyl 11.016       Cyclobutyl 11.017       Cyclopentyl 11.018       Cyclohexyl 11.019       Cycloheptyl 11.020       (CH.sub.2).sub.2 Cl 11.021       CH.sub.2 Cl 11.022       Phenyl 11.023       2-F-phenyl 11.024       3-F-phenyl 11.025       4-F-phenyl 11.026       2-Cl-phenyl 11.027       3-Cl-phenyl 11.028       4-Cl-phenyl 11.029       2-Br-phenyl 11.030       3-Br-phenyl 11.031       4-Br-phenyl 11.032       2-CH.sub.3 -phenyl 11.033       3-CH.sub.3 -phenyl 11.034       4-CH.sub.3 -phenyl 11.035       2-CF.sub.3 -phenyl 11.036       3-CF.sub.3 -phenyl 11.037       4-CF.sub.3 -phenyl 11.038       2-OCH.sub.3 -phenyl 11.039       3-OCH.sub.3 -phenyl 11.040       4-OCH.sub.3 -phenyl 11.041       4-NO.sub.2 -phenyl 11.042       4-CN-phenyl 11.043       2,4-Cl.sub.2 -phenyl 11.044       2,4-(CH.sub.3).sub.2 -phenyl 11.045       CH.sub.2 --OCH.sub.3 11.046       (CH.sub.2).sub.2 --OC.sub.2 H.sub.5 11.047       OH 11.048       OCH.sub.2 COOCH.sub.3 11.049       OCH.sub.2 COOC.sub.2 H.sub.5 11.050       OCH.sub.2 COO--CH(CH.sub.3).sub.2 11.051       OCH.sub.2 COO--C(CH.sub.3).sub.3 11.052       O--CH.sub.2 CH.dbd.CH.sub.2 11.053       O--CH(CH.sub.3)CH.dbd.CH.sub.2 11.054       O--CH.sub.2 C.tbd.CH 11.055       O--CH(CH.sub.3)--C.tbd.CH 11.056       O--CH.sub.2 --C.tbd.C--CH.sub.3 11.057       O--CH.sub.2 --CH.dbd.CH--CH.sub.3 11.058       O-cyclopentyl 11.059       O-cyclohexyl 11.060       O-cyclopent-3-enyl 11.061       O-cyclohex-3-enyl 11.062       O--(CH.sub.2).sub.2 --Cl 11.063       O--(CH.sub.2).sub.2 --Cl 11.064       O--(CH.sub.2)--F 11.065       O--CH.sub.2 --CF.sub.3 11.066       O--(CH.sub.2).sub.2 --Br 11.067       O--CH.sub.2 --CH.dbd.CHCl 11.068       O--CH.sub.2 --C(Cl).dbd.CH.sub.2 11.069       O--CH.sub.2 --C(Br).dbd.CH.sub.2 11.070       O--CH.sub.2 --CH.dbd.C(Cl)--CH.sub.3 11.071       O--CH.sub.2 --C(Cl).dbd.CCl.sub.2 11.072       O--CH.sub.2 -cyclopropyl 11.073       O--CH.sub.2 -cyclobutyl 11.074       O--CH.sub.2 -cyclopentyl 11.075       O--CH.sub.2 -cyclohexyl 11.076       O--CH.sub.2 -cycloheptyl 11.077       O--CO--CH.sub.3 11.078       O--CO--C.sub.2 H.sub.5 11.079       O--CH.sub.2 --CN 11.080       O--(CH.sub.2).sub.3 --CN 11.081       O--CH.sub.2 --OCH.sub.3 11.082       O--CH.sub.2 --OC.sub.2 H.sub.5 11.083       O--(CH.sub.2).sub.2 --OCH.sub.3 11.084       O--(CH.sub.2).sub.2 --OC.sub.2 H.sub.5 11.085       O--(CH.sub.2).sub.3 --OC.sub.2 H.sub.5 11.086       O--(CH.sub.2).sub.2 --CO--OCH.sub.3 11.087       O--(CH.sub.2).sub.2 --CO--OC.sub.2 H.sub.5 11.088       O--C(CH.sub.3)--CO--OCH.sub.3 11.089       O--C(CH.sub.3)--CO--OC.sub.2 H.sub.5 11.090       O--(CH.sub.2).sub.2 --OH 11.091       O--CH.sub.2 --SCH.sub.3 11.092       O--(CH.sub.2).sub.2 --N(CH.sub.3).sub.2 11.093       O--(CH.sub.2).sub.2 --N(C.sub.2 H.sub.5).sub.2 11.094       O--CH.sub.2 -phenyl 11.095       O--(CH.sub.2).sub.2 -phenyl 11.096       O--(CH.sub.2).sub.3 -phenyl 11.097       O--(CH.sub.2).sub.4 -phenyl 11.098       O--(CH.sub.2).sub.4 -(4-Cl-phenyl) 11.099       O--(CH.sub.2).sub.4 -(4-CH.sub.3 -phenyl) 11.100       O--(CH.sub.2).sub.4 -(4-CH.sub.3 -phenyl) 11.101       O--(CH.sub.2).sub.4 -(4-F-phenyl) 11.102       O--CH.sub.2 CH.dbd.CH-phenyl 11.103       O--CH.sub.2 CH.dbd.CH-(4-F-phenyl) 11.104       O--CH.sub.2 CH.dbd.CH-(4-Cl-phenyl) 11.105       O--CH.sub.2 CH.dbd.CH-(3-OCH.sub.3 - phenyl) 11.106       O--(CH.sub.2).sub.2 --CH.dbd.CH-(4-F- phenyl) 11.107       O--(CH.sub.2).sub.2 --CH.dbd.CH-(4-Cl- phenyl) 11.108       O--(CH.sub.2)--CH.dbd.CH-(3,4- Cl.sub.2 -phenyl) 11.109       O--CH.sub.2 --CH.dbd.C(CH.sub.3)-(4-F- phenyl) 11.110       O--CH.sub.2 --C.tbd.C--CH.sub.2 -phenyl 11.111       O--(CH.sub.2).sub.2 --O-phenyl 11.112       O--(CH.sub.2).sub.2 --OCH.sub.2 -phenyl 11.113       O--(CH.sub.2).sub.2 --OCH.sub.2 -(4-F- phenyl) 11.114       O--CH.sub.2 CH.dbd.CH--CH.sub.2 --O- phenyl 11.115       O--CH.sub.2 --C.tbd.C--CH.sub.2 --O-phenyl 11.116       O--CH.sub.2 --C.tbd.C--CH.sub.2 --O-(4-F- phenyl) 11.117       O--(CH.sub.2).sub.2 --SCH.sub.2 -phenyl 11.118       O--(CH.sub.2).sub.2 --SCH.sub.2 -(4-Cl- phenyl) 11.119       O--(CH.sub.2).sub.2 --N(CH.sub.3)--CH.sub.2 - phenyl 11.120       NH.sub.2 11.121       NH--CH.sub.3 11.122       NH--C.sub.2 H.sub.5 11.123       NH-n-C.sub.3 H.sub.7 11.124       NH-i-C.sub.3 H.sub.7 11.125       NH-n-C.sub.4 H.sub.9 11.126       NH-i-C.sub.4 H.sub.9 11.127       NH-s-C.sub.4 H.sub.9 11.128       NH--C(CH.sub.3).sub.3 11.129       NH-cyclopropyl 11.130       NH-cyclobutyl 11.131       NH-cyclopentyl 11.132       NH-cyclohexyl 11.133       NH-cyclohepty 11.134       N(CH.sub.3).sub.2 11.135       N(C.sub.2 H.sub.5).sub.2 11.136       NH--CH.sub.2 CH.dbd.CH.sub.2 11.137       NH--CH.sub.2 C.tbd.CH 11.138       NH--CH.sub.2 --CF.sub.3 11.139       NH--CO--CH.sub.3 11.140       NH--COC.sub.2 H.sub.5 11.141       NH--CO--OCH.sub.3 11.142       NH--CO--OC.sub.2 H.sub.5 11.143       NH--COO--C(CH.sub.3).sub.3 11.144       N-pyrrolidinyl 11.145       N-piperidinyl 11.146       N-morpholino 11.147       N-piperazinyl 11.148       NH-phenyl 11.149       NH-(4-Cl-phenyl) 11.150       NH-(4-F-phenyl) 11.151       NH-(4-OCH.sub.3 -phenyl) 11.152       NH-(2,4-Cl.sub.2 -phenyl) 11.153       CH.sub.2 --OCH.sub.3 11.154       (CH.sub.2).sub.2 --OCH.sub.3 ______________________________________ ______________________________________ No.               R.sup.12, R.sup.13 ______________________________________ 12.01             OCH.sub.3 12.02             OC.sub.2 H.sub.5 12.03             O--CH(CH.sub.3).sub.2 12.04             O-nC.sub.3 H.sub.7 12.05             O-nC.sub.4 H.sub.9 12.06             O-iC.sub.4 H.sub.9 12.07             O-sC.sub.4 H.sub.9 12.08             O--C(CH.sub.3).sub.3 12.09             Phenyl 12.10             2-Cl-phenyl 12.11             3-Cl-phenyl 12.12             2-F-phenyl 12.13             3-F-phenyl 12.14             4-F-phenyl 12.15             4-NO.sub.2 -phenyl 12.16             2,4-Cl.sub.2 -phenyl 12.17             2-F,4-CN-phenyl ______________________________________ ______________________________________ No.             R.sup.17, R.sup.18 ______________________________________ 17.01           CH.sub.3 17.02           C.sub.2 H.sub.5 17.03           n-C.sub.3 H.sub.7 17.04           i-C.sub.3 H.sub.7 17.05           n-C.sub.4 H.sub.9 17.06           i-C.sub.4 H.sub.9 17.07           s-C.sub.4 H.sub.9 17.08           C(CH.sub.3).sub.3 17.09           n-C.sub.5 H.sub.11 17.10           n-C.sub.6 H.sub.13 17.11           CH.sub.2 CH.dbd.CH.sub.2 17.12           CH(CH.sub.3)--CH.dbd.CH.sub.2 ______________________________________ ______________________________________ No.       R.sup.17 and R.sup.18 together ______________________________________ 18.01     --(CH.sub.2).sub.2 -- 18.02     --CH(CH.sub.3)--CH.sub.2 -- 18.03     --CH(C.sub.2 H.sub.5)--CH.sub.2 -- 18.04     --CH(CH.sub.3)--CH--(CH.sub.3)-- 18.05     --C(CH.sub.3).sub.2 --CH.sub.2 -- 18.06     --CH(CH.dbd.CH.sub.2)--CH.sub.2 -- 18.07     --CH(CH.sub.2 Cl)--CH.sub.2 -- 18.08     --CH(CH.sub.2 Br)--CH.sub.2 -- 18.09     --CH(CH.sub.2 OH)--CH.sub.2 -- 18.10     --CH(CH.sub.2 OCH.sub.3)--CH.sub.2 -- 18.11     --CH(CH.sub.2 OC.sub.2 H.sub.5)--CH.sub.2 -- 18.12     --CH(CH.sub.2 OCH.sub.2 CH.dbd.CH.sub.2)--CH.sub.2 -- 18.13     --CH(CH.sub.2 OCH.sub.2 C.tbd.CH)--CH.sub.2 -- 18.14     --CH(COOH)--CH.sub.2 -- 18.15     --CH(COOCH.sub.3)--CH.sub.2 -- 18.16     --CH(COOC.sub.2 H.sub.5)--CH.sub.2 -- 18.17     --CH(COO-n-C.sub.3 H.sub.7)--CH.sub.2 -- 18.18     --CH(COO--CH(CH.sub.3).sub.2)--CH.sub.2 -- 18.19     --CH(COO-n-C.sub.4 H.sub.9)--CH.sub.2 -- 18.20     --CH(COO-n-C.sub.5 H.sub.11)--CH.sub.2 -- 18.21     --CH(COO-n-C.sub.6 H.sub.13)--CH.sub.2 -- 18.22     --(CH.sub.2).sub.3 -- 18.23     --CH(CH.sub.3)--(CH.sub.2).sub.2 -- 18.24     --CH.sub.2 --CH(CH.sub.3)--CH.sub.2 -- 18.25     --CH(C.sub.2 H.sub.5)--(CH.sub.2).sub.2 -- 18.26     --CH.sub.2 --CH(C.sub.2 H.sub.5)--CH.sub.2 -- 18.27     --CH(CH.sub.3)--CH.sub.2 --CH(CH.sub.3)-- 18.28     --CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 -- 18.29     --CH(CH.sub.2 OH)--(CH.sub.2).sub.2 -- 18.30     --CH.sub.2 --CH(CH.sub.2 OH)--CH.sub.2 -- 18.31     --CH(CH.sub.2 OCH.sub.3)--(CH.sub.2).sub.2 -- 18.32     --CH(CH.sub.2 OCH.sub.2 CH.dbd.CH.sub.2)--(CH.sub.2).sub.2 -- 18.33     --CH(CH.sub.2 O--CO--CH.sub.3)--CH.sub.2 -- 18.34     --CH(CH.sub.2 OCH.sub.2 C.tbd.CH)--(CH.sub.2).sub.2 -- 18.35     --CH(CH.sub.2 OC(O)CH.sub.3)--(CH.sub.2).sub.2 -- 18.36     --CH.sub.2 --CH(CH.sub.2 OCH.sub.3)--CH.sub.2 -- 18.37     --CH.sub.2 --CH(CH.sub.2 OCH.sub.2 CH.dbd.CH.sub.2)--CH.sub.2 -- 18.38     --CH.sub.2 --CH(CH.sub.2 OCH.sub.2 C.tbd.CH)--CH.sub.2 -- 18.39     --CH.sub.2 --CH(CH.sub.2 OC(O)CH.sub.3)--CH.sub.2 -- 18.40     --CH(CH.sub.2 Cl)--(CH.sub.2).sub.2 18.41     --CH.sub.2 --CH(CH.sub.2 Cl)--CH.sub.2 -- 18.42     --C(CH.sub.3)--(COOCH.sub.3)--CH.sub.2 -- 18.43     --C(CH.sub.3)--(COOC.sub.2 H.sub.5)--CH.sub.2 -- 18.44     --C(CH.sub.3)(COO-n-C.sub.3 H.sub.7)--CH.sub.2 -- 18.45     --C(CH.sub.3)(COO-n-C.sub.4 H.sub.6)--CH.sub.2 -- 18.46     --CH(CH.sub.2 CN)--CH.sub.2 -- 18.47     --CH(CH.sub.2 CN)--(CH.sub.2).sub.2 -- 18.48     --CH.sub.2 --CH(CH.sub.2 CN)--CH.sub.2 -- 18.49     --CH.sub.2 --O--CH.sub.2 -- 18.50     --CH.sub.2 --NH--CH.sub.2 -- 18.51     --CH.sub.2 --N(CH.sub.3)--CH.sub.2 -- 18.52     --(CH.sub.2).sub.4 -- 18.53     --CH.sub.2 --CH.dbd.CH--CH.sub.2 -- 18.54     --CH.sub.2 --O--(CH.sub.2).sub.2 -- 18.55     --CO--CH.sub.2 -- 18.56     --CO--(CH.sub.2).sub.2 -- 18.57     --CH.sub.2 --CO--CH.sub.2 -- 18.58     --CO--C(CH.sub.3).sub.2 -- 18.59     --CO--O--CH.sub.2 -- 18.60     --CH.sub.2 --S--CH.sub.2 18.61     --CH(CH.sub.2 O--CO--CH.sub.3)--CH.sub.2 -- ______________________________________

The substituted isoindolones I are obtainable in various ways, in fact preferably by one of the following processes: and/or with a dehydrating agent: ##STR8## The dehydration is carried out in an inert organic solvent, suitable solvents for this purpose being, for example, aliphatic hydrocarbons such as n-hexane, aromatic hydrocarbons such as toluene such as toluene and o-, m- or p-xylene, chlorinated hydrocarbons such as dichloromethane and chlorobenzene, ethers such as diethyl ether, tetrahydrofuran, dioxane and diglyme, amides such as dimethylformamide and N-methylpyrrolidone or sulfoxides such as dimethyl sulfoxide. forms an azeotrope with water, in particular in toluene or dichloromethane, and the resulting water of reaction is continuously removed from the reaction mixture, for example by means of a Dean-Stark apparatus. particular sulfuric acid and hydrohalic acids such as hydrochloric acid, sulfonic acids such as p-toluenesulfonic acid, or acidic inorganic salts such as potassium hydrogen sulfate. phosphorus pentoxide. preferably from 20.degree. C. to the boiling point of the reaction mixture. reaction is expediently carried out at atmospheric pressure or under the autogenous pressure of the respective solvent. prepared from tetrahydrophthalimides III under the action of a suitable organometallic compound IV, Grignard reagents being particularly suitable: ##STR9## M is a metal atom which can be halogenated, in particular halogenated magnesium, particularly preferably magnesium iodide. Grignard reaction (cf., for example, U.S. Pat. No. 3,992,189, Houben-Weyl, Methoden d. Organischen Chemie (Methods of Organic Chemistry), Vol. 13/2a, Georg Thieme Verlag, Stuttgart 1973, p. 53 et seq. and R. C. Larock, Comprehensive Organic Transformations, Verlag Chemie, Weinheim 1989, p. 553 et seq. and the references cited therein). advantageous to work in the presence of a Lewis acid, a complexing agent or an additional base. trifluoride etherate. [18]crown-6, amides such as tetramethylethylenediamine, ureas such as 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone or hexamethylphosphoramide (cf., for example, Houben-Weyl, Methoden der Organischen Chemie (Methods of Organic Chemistry), Vol. E14a/2, Stuttgart 1991, p. 426 et seq.; A. I. Meyers and B. A. Lefkin, Tetrahedron Lett. (1987), 28, 1745; M. Yamaguchi and I. Hirao, J. Org. Chem. (1985), 50, 1975 and R. C. Larock, Comprehensive Organic Transformations, Verlag Chemie, Weinheim 1989, p. 553 et seq. and the references in each case indicated therein). tetrabutylammonium bromide or other organic nitrogen bases. the autogenous pressure of the respective solvent. references already cited above, reference may also be made to W. Flitsch and S. R. Schindler, Synthesis (1975), 685 and the literature cited therein. compound V with an aniline VI: ##STR10## This reaction is expediently carried out in the manner described in R. Scheffold and P. Dabs, Helv. Chim. Acta (1967) 50, 794 and the references cited therein. IX ##STR11## The reaction is carried out without solvent or in an inert solvent or diluent, preferably in the presence of an acidic catalyst. hydrocarbons such as n-hexane, toluene and xylene and also halogenated hydrocarbons, for example chlorobenzene and dichloromethane. hydrochloric acid and sulfuric acid, sulfonic acids such as methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid, or acidic alkali metal sulfates such as sodium hydrogen sulfate and potassium hydrogen sulfate. VIII or IX which is as complete as possible, a one- to two-fold molar amount of VI is required. preferably from 60.degree. to 150.degree. C. superatmospheric pressure. Expediently, however, it is carried out under atmospheric pressure or under the autogenous pressure of the reaction mixture. ##STR12## This method can only be used if R.sup.6 is a substituent inert to the olefination. If, on the other hand, R.sup.6 contains, for example, a carbonyl which can also be olefinated, this must be converted into a protective group, for example into an acetal, thioacetal or ketal, before the olefination reaction. as are customarily used for the Wittig or Wittig-Horner reaction known per se, or, for example, the Tebbe-Grubbs reagent (complex of titanocene tetrachloride and trimethylaluminum), the Nozaki-Lombardo reagent (obtainable by addition of titanium tetrachloride to a suspension of zinc dust and a geminal dibromide in tetrahydrofuran at about -40.degree. C., and also other transition metal carbene complexes, for example X or XI (cf. also R. C. Larock, Comprehensive Organic Transformations, p.180 et seq.): ##STR13## The reaction conditions for these processes can be taken, for example, from the following publications: Chemistry), Vol. E1, G. Thieme Verlag, Stuttgart 1982, p. 710 et seq.; references cited above, for example: chemistry)Teubner 1988, p. 253 et seq. and the references in each case cited therein.

Depending on the particular substituents, it may be expedient first to convert one of the two carbonyl groups of the 3,4,5,6-tetrahydrophthalimide III into a thiocarbonyl group and then to react this with a suitable olefination reagent without isolation from the reaction mixture.

Suitable olefination reagents for this purpose are in particular dimethyl bromomalonate or diethyl bromomalonate, and a suitable sulfurizing reagent is P.sub.4 S.sub.10 or 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-dithione (Lawesson's reagent).

The reaction is carried out in a manner known per se {cf., for example, J. S. Petersen et al., J. Am. Chem. Soc. (1984) 106, 4539 and S. C. Carey et al., Tetrahedron Lett. (1985) 26 5887}.

The 3,4,5,6-tetrahydrophthalimides III are known or obtainable by methods known per se (cf., for example, DE-A 36 03 789, DE-A 36 07 300, DE-A 37 41 273, EP-A 177 032, EP-A 188 259, EP-A 207 894, EP-A 218 972, EP-A 263 299, EP-A 271 170, EP-A 275 131, EP-A 290 863, EP-A 296 416, EP-A 300 307, EP-A 300 387, EP-A 300 398, JA 60/152 465, JA 60/246 367, JA 59/155 358, JA 61/027 962, JA 62/114 961, JA 61/165 383, JA 63/267 779, JA 63/275 580, JA 61/174 970, JA 01/034 982, JA 01/047 784 and JA 01/066 182).

In general, they can be prepared by condensation of a compound VI with tetrahydrophthalic anhydrides XIII: ##STR14##

For the condensation, inert organic solvents such as lower alkanoic acids, for example acetic acid, propionic acid and isobutyric acid, and also the esters of these acids, such as ethyl acetate, higher-boiling hydrocarbons such as toluene and xylene and/or dimethylformamide are used as solvents.

The reaction is normally carried out at from 0.degree. C. to the boiling point of the respective reaction mixture, preferably from 25.degree. to 140.degree. C. When using an aprotic solvent, it is recommended to remove the water continuously.

It may additionally be advantageous to carry out the condensation in the presence of an organic protic acid such as p-toluenesulfonic acid or benzenesulfonic acid.

Normally, the condensation is carried out at atmospheric pressure.

The compounds VI are also known or can be prepared by methods known per se, for example by reduction of the corresponding nitroaromatic.

Suitable reductants are, for example platinum on active carbon or suitable catalyst, expediently a commercially available noble metal catalyst (cf., for example, T. Neilson et al., J. Chem. Soc. (1962), 371 and references cited therein).

Reduction and condensation can be carried out without isolation of VI.

The compounds VII, VIII, IX and V are also known or can be prepared by known methods {cf., for example, R. Scheffold and D. Dabs, Helv. Chim. Acta (1967) 50, 798, EP-A 420 810, EP-A 305 333 and DE-A 3 920 271 and the references cited in each case}.

As a rule, the substituted isoindolones I can be prepared by one of the abovementioned synthesis processes. For economical or process engineering reasons, however, it may be more expedient to prepare some compounds I from similarly substituted isoindolones I which differ, however, in particular in the meanings of the radicals R.sup.1, R.sup.2 and/or R.sup.6, in a manner known per se, for example by ester hydrolysis, esterification, amidation, acetalisation, acetal hydrolysis, condensation reaction, Wittig reaction, Peterson olefination, etherification, alkylation, oxidation or reduction.

The substituted isoindolones can be obtained in the processes described above as isomer mixtures. Especially when R.sup.1 and R.sup.2 do not have the same meaning, E/Z isomer mixtures are obtained.

The isomers obtained, however, can be separated into the pure isomers, if desired using the methods customary for this purpose, for example by crystallization, chromatography (LC, HPLC, etc), if appropriate on an optically active absorbate (for this compare Example 4, compound Ic.13; separation method=LC).

Mixtures of optically active isomers I which contain one isomer in an excess can also be prepared, for example, using optically active starting materials.

Both the substituted isoindolones I and the hydroxyisoindolones II are suitable both as isomer mixtures and in the form of the pure isomers as herbicides and as defoliants/desiccants.

2-[4-Chloro-4-(2-chloro-2-ethoxycarbonylethenyl)phenyl]-3-hydroxy-3-methyl- 2,3,4,5,6,7-hexahydroisoindol-1-one (Compound IIa. 13)

1.21 g of magnesium turnings were reacted with 4.4 ml of methyl iodide in 30 ml of diethyl ether. A solution of 7.8 g of N-[4-chloro-3-(2-chloro-2-ethoxycarbonylethenyl)phenyl]-3,4,5,6-tetrahydro phthalimide in 130 ml of diethyl ether was added dropwise at 10.degree. C. to the solution of methylmagnesium iodide obtained. The reaction mixture was then stirred for a further 1 hour at boiling point, after which it was poured into 300 ml of saturated ammonium chloride solution. The organic phase was then separated off and concentrated.

The crude product was employed in the following step without further purification.

2-[4-Chloro-3-(2-chloro-2-ethoxycarbonylethenyl)phenyl]-3-methylidene-4,5,6 ,7-tetrahydro-2H-isoindon-1-one (Compound Ia. 13)

A solution of the 2-[4-chloro-3-(2-chloro-2-ethoxycarbonylethenyl)phenyl]-3-hydroxy-3-methyl -2,3,4,5,6,7-hexahydroisoindon-1-one obtained as described in Example 1 was treated with 0.1 g of p-toluenesulfonic acid in 150 ml of toluene. The mixture was heated to boiling point for two hours, then cooled and concentrated under reduced pressure.

The crude product was purified by means of chromatography on silica gel (using dichloromethane as the eluent) and purified by subsequent stirring with petroleum ether. Yield: 4.5 g; m.p. 85.degree.-86.degree. C.

2-[4-Chloro-4-(2-chloro-2-ethoxycarbonylethenyl)phenyl]-3-ethyl-3-hydroxy-2 ,3,4,5,6,7-hexahydroisoindol-1-one (Compound IIc.13)

1.21 g of magnesium turnings were reacted with 5.74 ml of ethyl iodide in 30 ml of diethyl ether. The solution of ethylmagnesium iodide obtained was added dropwise at 10.degree. C. to a solution of 7.8 g of N-[4-chloro-3-(2-chloro-2-ethoxycarbonylethenyl)phenyl]-3,4,5,6-tetrahydro phthalimide in 130 ml of diethyl ether. After heating to reflux temperature for 1.5 hours, the reaction mixture was added to 300 ml of saturated aqueous ammonium chloride solution. The organic phase was then separated off, dried over sodium sulfate and concentrated under reduced pressure.

One half of the crude product obtained was further reacted as described in Example 4; the other half was purified by chromatography on silica gel (eluent: 1, dichloromethane; 2, dichloromethane/ethyl acetate 4:1), 1.2 g of the product being obtained; m.p.: 64.degree.-67.degree. C.

2-[4-Chloro-3-(2-chloro-2-ethoxycarbonylethenyl)phenyl]-3-ethylidene-4,5,6, 7-tetrahydro-2H-isoindol-1-one (Compound Ic. 13)

A solution of the 2-[4-chloro-4-(2-chloro-2-ethoxycarbonylethenyl)phenyl]-3-ethyl-3-hydroxy- 2,3,4,5,6,7-hexahydroisoindol-1-one (Compound IIc.13; unpurified) obtained as described in Example 3 was treated with 0.1 g of p-toluenesulfonic acid in 150 ml of toluene. After heating to reflux temperature for 2 hours, the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel (eluent: 1, toluene; 2, dichloromethane).

Yield: 1.1 g of 2-[4-chloro-3-(2-chloro-2-ethoxycarbonylethenyl)phenyl]-3Z*)-ethylidene-4, 5,6,7-tetrahydro-2H-isoindol-1-one and 0.9 g of 2-[4-Chloro-3-(2-chloro-2-ethoxycarbonylethenyl)phenyl]-3E*)-ethylidene-4, 5,6,7-tetrahydro-2H-isoindol-1-one

2-[4-Chloro-3-(4-methyl-1,3-dithiolan-2-yl)phenyl]-3-(ethoxycarbonylethylid ene)-4,5,6,7-tetrahydro-2H-isoindol -1-one

1.75 g of (ethoxycarbonylmethylene)triphenylphosphorane were added to a solution of 1.90 g of 2-[4-chloro-3-(4-methyl-1,3-dithiolan-2-yl)phenyl]-4,5,6,7-tetrahydro-2H-i soindol-1,3-dione in 50 ml of toluene. The solution obtained was then refluxed for 5 hours, after which a further 5.25 g of (ethoxycarbonylmethylene)triphenylphosphorane were added in two portions. The reaction mixture was refluxed for a total of 6 hours and then cooled to about 25.degree. C. After separating off solid components and solvent, the residue was treated with diisopropyl ether. The substance crystallizing from diisopropyl ether was separated off and the filtrate was chromatographed on silica gel (eluent: CH.sub.2 Cl.sub.2). Yield : 0.7 g of the title compound as an 85:15 E/Z isomer mixture.

In the following tables 17 and 18, particularly preferred substituted isoindolones I are shown which were prepared or can be prepared in the same manner: ______________________________________ ##STR15## No.  R.sup.4 R.sup.6              M.p. [.degree.C.] ______________________________________ Ia.01 H       CHCHCN Ia.02 F       CHCHCN Ia.03 H       CHC(CH.sub.3)CN Ia.04 F       CHC(CH.sub.3)CN Ia.05 H       CHCHCOOCH.sub.3 Ia.06 F       CHCHCOOCH.sub.3 Ia.07 H       CHCHCOOC.sub.2 H.sub.5 oil Ia.08 F       CHCHCOOC.sub.2 H.sub.5 Ia.09 H       CHC(CN)COOCH.sub.3 Ia.10 F       CHC(CN)COOCH.sub.3 Ia.11 H       CHC(Cl)COOCH.sub.3 Ia.12 F       CHC(Cl)COOCH.sub.3 Ia.13 H       CHC(Cl)COOC.sub.2 H.sub.5 85-86 Ia.14 F       CHC(Cl)COOC.sub.2 H.sub.5 Ia.15 H       CHC(Br)COOCH.sub.3   76-78 Ia.16 F       CHC(Br)COOCH.sub.3 Ia.17 H       CHC(Br)COOC.sub.2 H.sub.5 Ia.18 F       CHC(Br)COOC.sub.2 H.sub.5 Ia.19 H       CH.sub.2 CN Ia.20 F       CH.sub.2 CN Ia.21 H       CH.sub.2 CH.sub.2 COOCH.sub.3 Ia.22 F       CH.sub.2 CH.sub.2 COOCH.sub.3 Ia.23 H       CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5 Ia.24 F       CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5 Ia.25 H       CH.sub.2 CH(CN)COOCH.sub.3 Ia.26 F       CH.sub.2 CH(CN)COOCH.sub.3 Ia.27 H       CH.sub.2 CH(Cl)COOCH.sub.3 Ia.28 F       CH.sub.2 CH(Cl)COOCH.sub.3 Ia.29 H       CH.sub.2 C(Cl)COOC.sub.2 H.sub.5 Ia.30 F       CH.sub.2 C(Cl)COOC.sub.2 H.sub.5 Ia.31 H       CH.sub.2 C(Br)COOCH.sub.3 Ia.32 F       CH.sub.2 C(Br)COOCH.sub.3 Ia.33 H       CH.sub.2 C(Br)COOC.sub.2 H.sub.5 Ia.34 F       CH.sub.2 C(Br)COOC.sub.2 H.sub.5 Ia.35 H       1,3-dioxolan-2-yl Ia.36 F       1,3-dioxolan-2-yl Ia.37 H       1,3-dioxan-2-yl      103-105 Ia.38 F       1,3-dioxan-2-yl Ia.39 H       1,3-dithiolan-2-yl Ia.40 F       1,3-dithiolan-2-yl Ia.41 H       1,3-dithian-2-yl Ia.42 F       1,3-dithian-2-yl Ia.43 H       4-CH.sub.3 -1,3-dithiolan-2-yl 110-112 Ia.44 F       4-CH.sub.3 -1,3-dithiolan-2-yl Ia.45 H       CH(OCH.sub.3).sub.2 Ia.46 F       CH(OCH.sub.3).sub.2 Ia.47 H       CH(OC.sub.2 H.sub.5).sub.2 Ia.48 F       CH(OC.sub.2 H.sub.5).sub.2 Ia.49 H       CHNOCH.sub.2 COOCH.sub.3 Ia.50 F       CHNOCH.sub.2 COOCH.sub.3 Ia.51 H       CHNOH Ia.52 F       CHNOH Ia.53 H       CHNOCH(CH.sub.3)COOCH.sub.3 Ia.54 F       CHNOCH(CH.sub.3)COOCH.sub.3 Ia.55 H       CHNOCH(CH.sub.3)COOC.sub.2 H.sub.5 Ia.56 F       CHNOCH(CH.sub.3)COOC.sub.2 H.sub.5 ______________________________________ ______________________________________ ##STR16## M.p. No.  R.sup.4 (R.sup.5 R.sup.6)        [.degree.C.] ______________________________________ Ib.01 H      OCH.sub.2 CON(CH.sub.3) Ib.02 H ##STR17## Ib.03 H ##STR18## Ib.04 H      OCH(CH.sub.3)N(CH.sub.3) Ib.05 H ##STR19## Ib.06 H      SCH.sub.2 CON(CH.sub.3) Ib.07 F      SCH.sub.2 CON(CH.sub.3) Ib.08 H ##STR20## Ib.09 F ##STR21## Ib.10 H ##STR22## Ib.11 F ##STR23## Ib.12 H ##STR24## Ib.13 F ##STR25## Ib.14 H ##STR26## Ib.15 F ##STR27## Ib.16 H ##STR28## Ib.17 F ##STR29## Ib.18 H ##STR30## Ib.19 F ##STR31## ______________________________________

In addition, the following substituted isoindolones I are particularly preferred: Ia.01 to Ia.56 in that R.sup.1 is in each case methyl; Ia.01 to Ia.56 in that R.sup.1 is in each case ethyl; Ia.01 to Ia.56 in that R.sup.1 is in each case n-propyl; Ia.01 to Ia.56 in that R.sup.1 is in each case n-pentyl; Ia.01 to Ia.56 in that R.sup.1 is in each case phenyl; Ib.01 to Ib.19 in that R.sup.1 is in each case methyl; Ib.01 to Ib.19 in that R.sup.1 is in each case ethyl; Ia.01 to Ia.56 in that R.sup.1 is in each case ethoxycarbonyl.

The following tables 19 and 20 contain hydroxyindolones II of the invention which are particularly preferred: ______________________________________ ##STR32## No.     R.sup.4 R.sup.6           M.p. [.degree.C.] ______________________________________ IIa.01  H       CHCHCN IIa.02  F       CHCHCN IIa.03  H       CHC(CH.sub.3)CN IIa.04  F       CHC(CH.sub.3)CN IIa.05  H       CHCHCOOCH.sub.3 IIa.06  F       CHCHCOOCH.sub.3 IIa.07  H       CHCHCOOC.sub.2 H.sub.5 150-152 IIa.08  F       CHCHCOOC.sub.2 H.sub.5 IIa.09  H       CHC(CN)COOCH.sub.3 IIa.10  F       CHC(CN)COOCH.sub.3 IIa.11  H       CHC(Cl)COOCH.sub.3 IIa.12  F       CHC(Cl)COOCH.sub.3 IIa.13  H       CHC(Cl)COOC.sub.2 H.sub.5 IIa.14  F       CHC(Cl)COOC.sub.2 H.sub.5 IIa.15  H       CHC(Br)COOCH.sub.3 60-70 (dec.) IIa.16  F       CHC(Br)COOCH.sub.3 IIa.17  H       CHC(Br)COOC.sub.2 H.sub.5 IIa.18  F       CHC(Br)COOC.sub.2 H.sub.5 IIa.19  F       CH.sub.2 CN IIa.20  F       CH.sub.2 CN IIa.21  H       CH.sub.2 CH.sub.2 COOCH.sub.3 IIa.22  F       CH.sub.2 CH.sub.2 COOCH.sub.3 IIa.23  H       CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5 IIa.24  F       CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5 IIa.25  H       CH.sub.2 CH(CN)COOCH.sub.3 IIa.26  F       CH.sub.2 CH(CN)COOCH.sub.3 IIa.27  H       CH.sub.2 CH(Cl)COOCH.sub.3 IIa.28  F       CH.sub.2 CH(Cl)COOCH.sub.3 IIa.29  H       CH.sub.2 C(Cl)COOC.sub.2 H.sub.5 IIa.30  F       CH.sub.2 C(Cl)COOC.sub.2 H.sub.5 IIa.31  H       CH.sub.2 C(Br)COOCH.sub.3 IIa.32  F       CH.sub.2 C(Br)COOCH.sub.3 IIa.33  H       CH.sub.2 C(Br)COOC.sub.2 H.sub.5 IIa.34  F       CH.sub.2 C(Br)COOC.sub.2 H.sub.5 IIa.35  H       1,3-dioxolan-2-yl IIa.36  F       1,3-dioxolan-2-yl IIa.37  H       1,3-dioxan-2-yl   163-165 IIa.38  F       1,3-dioxan-2-yl IIa.39  H       1,3-dithiolan-2-yl IIa.40  F       1,3-dithiolan-2-yl IIa.41  H       1,3-dithian-2-yl IIa.42  F       1,3-dithian-2-yl IIa.43  F       4-CH.sub.3 -1,3-dithiolan-2-yl 110-112 IIa.44  H       4-CH.sub.3 -1,3-dithiolan-2-yl ______________________________________ ______________________________________ ##STR33## M.p. No.   R.sup.4 (R.sup.5 R.sup.6)       [.degree.C.] ______________________________________ IIb.01 H      OCH.sub.2 CON(CH.sub.3) IIb.02 F ##STR34## IIb.03 H      OCH(CH.sub.3)N(CH.sub.3) IIb.04 F ##STR35## IIb.05 H      SCH.sub.2 CON(CH.sub.3) IIb.06 F      SCH.sub.2 CON(CH.sub.3) IIb.07 H ##STR36## IIb.08 F ##STR37## IIb.09 H ##STR38## IIb.10 F ##STR39## IIb.11 H ##STR40## IIb.12 F ##STR41## IIb.13 H ##STR42## IIb.14 F ##STR43## IIb.15 H ##STR44## IIb.16 F ##STR45## IIb.17 H ##STR46## IIb.18 F ##STR47## ______________________________________

In addition, the following hydroxyisoindolones II are particularly preferred: IIa.44 in that R.sup.1 is methyl; IIa.44 in that R.sup.1 is ethyl; IIa.44 in that R.sup.1 is n-propyl; IIa.44 in that R.sup.1 is n-pentyl; IIa.44 in that R.sup.1 is phenyl; IIb.18 in that R.sup.1 is methyl; IIb.18 in that R.sup.1 is ethyl.

Physical data of compounds I and II are evident from the following Table 21: ______________________________________ Compound M.p. or spectroscopic data No.     (IR [cm.sup.-1 ]; .sup.1 H-NMR [ppm]) ______________________________________ Ia.07   Oil, IR: .nu. = 1712, 1636, 1474, 1420, 1379, 1367, 1314, 1265, 1180, 1042 Ic.13   E-isomer; oil; NMR (CDCl.sub.3, 250 MHz): .delta. = 1.39 (t, 3H); 1.66-1.89 (m, 4H); 1.98 (d, 3H); 2.33-2.47 (m, 2H); 2.65-2.78 (m, 2H); 4.37 (q); 5.36 (q); 7.16-7.83 (m, 3H); 8.15 (s, 1H); Z-isomer; oil; NMR (CDCl.sub.3, 250 MHz): .delta. = 1.39 (t, 3H); 1.41 (d, 3H); 1.68-1.85 (m, 4H); 2.28-2.45 (m, 4H); 4.37 (q, 3H); 5.25 (q, 3H); 7.12-7.88 (m, 3H); 8.14 (s, 1H) Ic.43   oil, IR: .nu. = 2931, 1697, 1659, 1471, 1413, 1390, 1371, 1122, 1067, 1039 Id.43   oil, IR: .nu. = 2962, 2931, 2869, 1698, 1471, 1412, 1387, 1158, 1118, 1039 If.43   oil, IR: .nu. = 2952, 2927, 2856, 1699, 1470, 1435, 1413, 1387, 1123, 1041 Ik.43   oil; NMR (CDCL.sub.3 : .delta. = 1.24 (t, 3H); 1.49 (2d, 3H); 1.77 (bs, 4H); 2.33-2.50 (2H); 2.75-2.84 (2H); 2.96-3.10 (mk, 1H); 3.23-3.45 (mk, 1H); 3.88-4.03 (mk, 1H); 4.93 (q, 2H); 5.44 (2s, 1H); 6.03 (s, 1H); 7.01-7.10, 7.42-7.48, 7.72-7.84 (3H) IIc.13  64 to 67.degree. C. IIc.43  151 to 153.degree. C. IId.43  147 to 148.degree. C. IIf.43  oil, IR: .nu. = 3350, 2928, 2857, 1679, 1472, 1422, 1397, 1372, 1071, 1052 ______________________________________

The substituted isoindolones I and hydroxyisoindolones II are useful, both as isomer mixtures and in the form of the pure isomers, as herbicides, in particular for controlling dicotyledon weeds. In particular at low application rates, they are tolerable and thus selective in cultures such as wheat, rice, corn, soya and cotton.

The substituted isoindolones I and hydroxyisoindolones II are additionally useful as desiccants and defoliants, in particular for defoliating cotton, and as defoliants for drying the above-ground parts of plants in cultivated plants, for example potato, sunflower, soya bean and rape. Completely mechanised harvesting of these important cultivated plants is thus made possible.

Of economical interest is additionally the facilitation of harvesting, which is made possible by the temporally concentrated dropping of the fruit or reduction in its power of adhesion to the tree in the case of citrus fruits, olives or other varieties and types of pomiferous, drupaceous and indehiscent fruit trees. Additionally, the compounds lead to a uniform ripening-off of the harvested fruit.

The same mechanism, ie. the promotion of the formation of separating tissue between the fruit or leaf and stem part of the plant is also essential for a readily controllable defoliation of useful plants such as, in particular, cotton. Additionally, the shortening of the time interval in which the individual cotton plants become ripe leads to an increased fiber quality after harvesting.

The compounds I and II or the herbicides or desiccants/defoliants containing them can be used, for example, in the form of directly sprayable solutions, powders, suspensions, including high-percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents or granules by spraying, atomizing, dusting, scattering or pouring. The application forms depend on the intended use; in each case, if possible, they should ensure the finest dispersion of the active compounds.

The compounds I and II are generally suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions. Suitable inert additives are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, and also coal-tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, chlorobenzene, isophorone or strongly polar solvents, such as N,N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone or water.

Aqueous application forms can be prepared from emulsion concentrates, dispersions, pastes, wettable powders or water-dispersible granules by the addition of water. For the preparation of emulsions, pastes or oil dispersions, the substrates can be homogenized in water as such or in an oil or solvent by means of wetting agents, tackifiers, dispersants or emulsifiers. However, concentrates consisting of active substance, wetting agent, tackifer, dispersant or emulsifier and possibly solvent or oil which are suitable for dilution with water can also be prepared.

Suitable surface-active substances are the alkali metal, alkaline earth metal or ammonium salts of aromatic sulfonic acids, for example lignin-, phenol-, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and also salts of sulfated hexa-, hepta- and octadecanols, as well as of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenol or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol ester, lignin-sulfite waste liquors or methyl cellulose.

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

Granules, e.g. coated, impregnated and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths such as silica gel, silicic acids, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and plant products, such as cereal flour, tree bark, wood and nutshell meal, cellulose powder or other solid carriers.

The formulations in general contain from 0.01 to 95% by weight, preferably from 0.5 to 90% by weight, of active compound. The active compounds are in this case employed in a purity of 90%-100%, preferably 95%-100% (by NMR spectrum).

Examples of such preparations are:

I. a mixture of 20 parts by weight of compound No. Ia.07, 80 parts by weight of xylene, 10 parts by weight of the addition products of 8-10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 5 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil. By fine dispersion of the mixture in 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.02% by weight of the active compound; mixture of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of caster oil. The mixture of this dispersion with 100,000 parts by weight of water contains 0.02% by weight of the active compound; of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210.degree.-280.degree. C. and 10 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil. The mixture of this dispersion with 100,000 parts by weight of water contains 0.02 % by weight of the active compound; No. IIc.13, 3 parts by weight of the sodium salt of diisobutylnaphthalene-.alpha.-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel. By fine dispersion of the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active compound; parts by weight of finely divided kaolin. This dust contains 3% by weight of active compound; 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.

The application of the herbicides or of the active compounds can be carried out pre-emergence or post-emergence. If the active compounds are less tolerable to certain crop plants, application techniques can be used in which the herbicides are sprayed with the aid of spraying equipment such that the leaves of the sensitive crop plants are not affected if possible, while the active compounds reach the leaves of undesired plants growing underneath or the uncovered soil surface (post-directed, lay-by).

The application rates of active compound are, depending on the control target, time of year, target plants and stage of growth, from 0.001 to 3.0, preferably from 0.01 to 1 kg/ha of active substance (a.s.).

In view of the versatility of the application methods, the compounds I and II or compositions containing them can additionally be employed in a further number of crop plants for the elimination of undesired plants. The following crops, for example, are suitable: Botanical Name      Common Name ______________________________________ Allium cepa         onions Ananas comosus      pineapples Arachis hypogaea    peanuts (groundnuts) Asparagus officinalis asparagus Beta vulgaris spp. altissima sugar beets Beta vulgaris spp. rapa fodder beets Brassica napus var. napus rapeseed Brassica napus var. napobrassica swedes Brassica rapa var. silvestris turnips Camellia sinensis   tea plants Carthamus tinctorius safflower Carya illinoinensis pecan trees Citrus limon        lemons Citrus senensis     orange trees Coffea arabica (Coffea coffee canephora, Coffea liberica) Cucumis sativus     cucumbers Cynodon dactylon    Bermuda grass Daucus carota       carrots Elaeis guineensis   oil palms Fragaria vesca      strawberries Glycine max         soybeans Gossypium hirsutum (Gossypium cotton arboreum, Gossypium herbaceum, Gossypium vitifolium) Helianthus annuus   sunflowers Hevea brasiliensis  rubber plants Hordeum vulgare     barley Humulus lupulus     hops Ipomoea batatas     sweet potatoes Juglans regia       walnut trees Lens culinaris      lentils Linum usitatissimum flax Lycopersicon lycopersicum tomatoes Malus spp.          apple trees Manihot esculenta   cassava Medicago sativa     alfalfa (lucerne) Musa spp.           banana plants Nicotiana tabacum (N. rustica) tobacco Olea europaea       olive trees Oryza sativa        rice Phaseolus lunatus   Lima beans Phaseolus vulgaris  snap beans, green beans, dry beans Picea abies         Norway spruce Pinus spp.          pine trees Pisum staivum       English peas Prunus avium        cherry trees Prunus persica      peach trees Pyrus communis      pear trees Ribes sylvestre     redcurrants Ricinus communis    castor-oil plants Saccharum officinarum sugar cane Secale cereale      rye Solanum tuberosum   Irish potatoes Sorghum bicolor (S. vulgare) sorghum Theobroma cacao     cacao plants Trifolium pratense  red clover Triticum aestivum   wheat Triticum durum      durum wheat Vicia faba          tick beans Vitis vinifera      grapes Zea mays            Indian corn, sweet corn, maize ______________________________________

To widen the spectrum of action and to obtain synergistic effects, the compounds I and II can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together. For example, suitable mixture components are diazines, 4H- 3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiocarbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane- 1,3-dione derivatives which in the 2 position carry e.g. a carboxyl or carbimino group, quinoline- carboxylic acid derivatives, imidazolinones, sulfonamides, sulfonylureas, aryloxy- and hetaryloxyphenoxypropionic acids and their salts, esters and amides and others.

Additionally, it may be useful to apply the compounds I and II on their own or together in combination with other herbicides, also additionally mixed with other crop protection compositions, for example with compositions for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions which are used for rectifying nutritional and trace element deficiencies. However, non-phytotoxic oils and oil concentrates can also be added.

(herbicidal activity)

The herbicidal action of the substituted isoindolones I and hydroxyisoindolones II could be shown by greenhouse tests:

The cultivation containers used were plastic flowerpots containing loamy sand with about 3.0% by weight of humus as substrate. The seeds of the test plants were sown separately according to variety.

In the case of pre-emergence treatment, the active compounds suspended or emulsified in water were applied directly after sowing by means of finely dividing nozzles. The containers were lightly watered in order to promote germination and growth and then covered with transparent plastic caps until the plants had taken root. This covering caused uniform germination of the test plants inasmuch as this was not affected by the active compounds.

For the purpose of post-emergence treatment, the test plants were grown, depending on form of growth, up to a height of growth of from 3 to 15 cm and only then treated with the active compounds suspended or emulsified in water. The test plants were either sown and grown in the test containers in which they were treated, or they were grown separately as seed plants and transplanted into the test containers a few days before the treatment with the active compound preparations.

The application rate for post-emergence treatment was 0.5 kg/ha a.s.

The plants were kept according to variety at temperatures of from 10.degree. to 25.degree. C. or from 20.degree. to 35.degree. C. The test period ranged from 2 to 4 weeks. During this time, the plants were cared for and their reaction to the individual treatments was assessed.

Assessment was carried out on a scale from 0 to 100. In this, 100 means no emergence of the plants or complete destruction at least of the above-ground parts and 0 means no damage or a normal course of growth.

The plants used in the greenhouse tests consisted of the following varieties: Latin Name        English name ______________________________________ Abutilon theophrasti velvet leaf Amaranthus retroflexus redroot pigweed Galium aparine    catchweed bedstraw Chenopodium album lambsquarters (goosefoot) Ipomoea subspecies morning-glory Solanum nigrum    black nightshade ______________________________________

The result showed that undesired weeds can be very well controlled using the compounds Nos. Ia.13, Ia.43 and Ic.13 (E- and Z- isomer with respect to R.sup.1).

## Claims

1. A substituted isoindolone of the formula I ##STR48## where the variables have the following meanings: R.sup.1 and R.sup.2 are -C.sub.6 -alkynyl, tri-(C.sub.1 -C.sub.6 -alkyl)silyl-C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, cyano, C.sub.1 -C.sub.6 -cyanoalkyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, formyl, C.sub.1 -C.sub.6 -alkylcarbonyl, phenylcarbonyl where the phenyl ring may be unsubstituted or may be substituted by one to three radicals selected from the group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, halogen, cyano, nitro and trifluoromethyl, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl and C.sub.1 -C.sub.6 -haloalkyl, unsubstituted or may be substituted by one to three radicals selected from the group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, halogen, cyano, nitro and trifluoromethyl, bonded, form a three- to eight-membered saturated or unsaturated non-aromatic carbo- or heterocycle which ring may contain one to three N atoms and an additional oxygen or sulfur atom and also one or two carbonyl groups as ring members, which ring may be substituted by one to three identical or different C.sub.1 -C.sub.6 -alkyl groups; completely unsaturated and may optionally contain one to four heteroatoms selected from the group consisting of one to four nitrogen atoms, one or two oxygen atoms and one or two sulfur atoms, where the heterocycle may optionally be substituted by one of the following substituents on each substitutable atom: C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkoxycarbonyl, or --C(R.sup.10).dbd.S, --C(R.sup.10).dbd.N--R.sup.11, --C(X.sup.1 R.sup.14)(X.sup.2 R.sup.15)R.sup.10, --P(R.sup.12)(R.sup.13).dbd.O, where -C.sub.4 -alkynylene chain which may in each case be unsubstituted or may optionally be substituted by one or two radicals selected from the group consisting of halogen, cyano, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxycarbonyl and C.sub.1 -C.sub.6 -alkylcarbonyl; -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.8 -cycloalkyl -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.2 -C.sub.6 -haloalkyl, radicals selected from the group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -alkoxycarbonyl, -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkoximino-C.sub.1 -C.sub.6 -alkyl; radicals selected from the group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -alkoxycarbonyl; are hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl or phenyl which may be unsubstituted or may be substituted by one to three radicals selected from the group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.8 -alkoxycarbonyl, or where saturated or partially or completely unsaturated 4- to 7-membered ring which may additionally contain one or two further heteroatoms as ring members, selected from the group consisting of nitrogen, oxygen and sulfur; -alkoxy)-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkylthio-C.sub.1 --C.sub.6 -alkyl; -alkynyl, -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.6 -haloalkyl, to three radicals selected from the group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -alkoxycarbonyl, -C.sub.7 -cycloalkoxy, C.sub.5 -C.sub.7 -cycloalkenyloxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.3 -C.sub.6 -haloalkenyloxy, C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.6 -alkoxy, -alkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkoxy, hydroxy-C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylamino-C.sub.1 -C.sub.6 -alkoxy, di-(C.sub.1 -C.sub.6 -alkyl)-amino-C.sub.1 -C.sub.6 -alkoxy, phenyl-C.sub.3 -C.sub.6 -alkynyloxy, where in each case one or two methylene groups of the alkoxy, alkenyloxy and alkynyloxy chains may be replaced by oxygen, sulfur and/or a C.sub.1 -C.sub.6 -alkylamino chain, and where the phenyl ring may be unsubstituted or may optionally be substituted by one to three substituents selected from the group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -alkoxycarbonyl, optionally be substituted by one to three radicals selected from the group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -alkoxy-carbonyl; X.sup.1 and X.sup.2 are oxygen or sulfur; -alkynyl or C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl or which may be unsaturated and which, optionally, may contain a carbonyl group as a chain member, substituted by one to three radicals selected from the group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, halogen, cyano, nitro, amino, C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy, carboxyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyloxy-C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkynyloxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -hydroxyalkyl and C.sub.1 -C.sub.6 -cyanoalkyl; five-membered carbon chain which, optionally, may contain one or two oxygen, sulfur or nitrogen atoms and/or a carbonyl group as a chain member, and where the chain may be unsubstituted or may optionally be substituted by one or two radicals selected from the group consisting of cyano, nitro, amino, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -cyanoalkyl, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl,phenyl-C.sub.1 -C.sub.6 -alkyl and 3- to 8-membered heterocyclyl-C.sub.1 -C.sub.6 -alkyl, where the heterocycle may in turn be saturated or partially or completely unsaturated and may optionally contain one to four heteroatoms selected from the group consisting of one to four nitrogen atoms, one or two oxygen atoms and one or two sulfur atoms; hydrogen and R.sup.5 and R.sup.6 together form a substituted chain --CH.dbd.CH--NH-- and excluding those compounds of formula I in which R.sup.1 and R.sup.2 are hydrogen and R.sup.4 is fluorine and R.sup.5 and R.sup.6 together are a substituted chain --O--CH.sub.2 --CO--NH--, and the agriculturally utilizable salts of the compounds of formula I.

2. A compound of the formula I as defined in claim 1, wherein -alkenyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkoxy)carbonyl or (C.sub.1 -C.sub.6 -alkyl)carbonyl; --C(R.sup.10).dbd.N--R.sup.11, where -C.sub.4 -alkynylene chain which in each case is unsubstituted or may optionally be substituted by one or two radicals selected from the group consisting of halogen, C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkoxy)carbonyl and (C.sub.1 -C.sub.6 -alkyl)carbonyl; -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy, C.sub.5 -C.sub.7 -cycloalkoxy, C.sub.5 -C.sub.7 -cycloalkenyloxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.3 -C.sub.6 -haloalkenyloxy, C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.6 -alkoxy, (C.sub.1 -C.sub.6 -alkoxy)carbonyl-C.sub.1 -C.sub.6 -alkoxy or --NR.sup.8 R.sup.9.

3. A compound of the formula I as defined in claim 1, wherein -alkenyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl or (C.sub.1 -C.sub.6 -alkyl )carbonyl; --C(R.sup.10).dbd.N--R.sup.11, where optionally be substituted by one or two radicals selected from the group consisting of halogen, C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkoxy)carbonyl and (C.sub.1 -C.sub.6 -alkyl)carbonyl; B is --OR.sup.16 ; and -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy, C.sub.5 -C.sub.7 -cycloalkoxy, C.sub.5 -C.sub.7 -cycloalkenyloxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.3 -C.sub.6 -haloalkenyloxy, C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.6 -alkoxy, (C.sub.1 -C.sub.6 -alkoxy )carbonyl-C.sub.1 -C.sub.6 -alkoxy or --NR.sup.8 R.sup.9.

4. A substituted hydroxyisoindolone of the formula II ##STR49## in which the variables have the meanings given in claim 1, for the compounds of formula I and the agriculturally utilizable salts of the compounds II.

5. A herbicidal composition containing an inert liquid or solid carrier and a herbicidally active amount of at least one substituted isoindolone compound of the formula I as defined in claim 1 or an agriculturally utilizable salt of a compound of formula I.

6. A composition for desiccating and/or defoliating plants, containing, in addition to customary additives, an amount of at least one substituted isoindolone compound of the formula I having desiccant and/or defoliant activity or an agriculturally utilizable salt of a compound of formula I as defined in claim 1.

7. A method for controlling undesired plant growth, which comprises allowing a herbicidally active amount of at least one substituted isoindolone compound of the formula I or an agriculturally utilizable salt of a compound of formula I as defined in claim 1 to act on plants or their environment or on seeds.

8. A method for desiccating and/or defoliating plants, which comprises allowing an effective amount of a composition which has desiccant and/or defoliant activity as defined in claim 6 to act on the plants.

9. A herbicidal composition containing an inert liquid or solid carrier and an amount of at least one hydroxyisoindolone compound of the formula II as defined in claim 4 having herbicidal activity or an agriculturally utilizable salt of a compound of the formula II as defined in claim 4.

10. A composition for desiccating and/or defoliating plants, containing, in addition to customary additives, an amount of at least one hydroxyisoindolone compound of the formula II as defined in claim 4 having desiccant and/or defoliant activity or an agriculturally utilizable salt of a compound of the formula II as defined in claim 4.

11. A method for controlling undesired plant growth, which comprises allowing an amount of at least one hydroxyisoindolone compound of the formula II as defined in claim 4 having herbicidal activity or an agriculturally utilizable salt of a compound of the formula II as defined in claim 4 to act on plants or their environment or on seeds.

12. A method for desiccating and/or defoliating plants, which comprises allowing an effective amount of a composition having desiccant or defoliant activity as defined in claim 10 to act on the plants.