HERBICIDAL MALONAMIDES

Abstract

The present invention relates to malonamide compounds of the formula (I) wherein the variables are as defined in the claims and the description, and to compositions comprising these compounds. The invention also relates to the use of said malonamide compounds or the corresponding compositions for controlling unwanted vegetation. Furthermore, the invention relates to methods for controlling unwanted vegetation wherein said malonamide compounds or the corresponding compositions are applied.

##STR00001##

Claims

1. Compounds of formula (I) ##STR00193## wherein the substituents have the following meanings: R.sup.1 is hydrogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.4)-cycloalkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.2-C.sub.3)-alkenyl, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3)-alkynyl, (C.sub.2-C.sub.3)-haloalkynyl, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-alkoxy, or (C.sub.1-C.sub.3)-haloalkoxy; R.sup.2 is hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, or (C.sub.1-C.sub.3)-haloalkoxy; R.sup.3 is hydrogen, halogen, nitro, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, hydroxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.5)-cycloalkyl, (C.sub.3-C.sub.5)-halocycloalkyl, hydroxy-(C.sub.3-C.sub.5)-cycloalkyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy, (C.sub.1-C.sub.3)-alkoxycarbonyl, (C.sub.2-C.sub.3) alkenyl, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3) alkynyl, (C.sub.2-C.sub.3)-haloalkynyl, (C.sub.1-C.sub.3)-alkylthio, (C.sub.1-C.sub.3)-alkylsulfinyl, or (C.sub.1-C.sub.3)-alkylsulfonyl; R.sup.4 is hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.3-C.sub.4)-halocycloalkyl, (C.sub.1-C.sub.3)-haloalkoxy, (C.sub.2-C.sub.3)-haloalkenyl, or (C.sub.2-C.sub.3)-haloalkynyl; R.sup.5 is hydrogen, halogen, nitro, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, hydroxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.5)-cycloalkyl, (C.sub.3-C.sub.5)-halocycloalkyl, hydroxy-(C.sub.3-C.sub.5)-cycloalkyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy, (C.sub.1-C.sub.3)-alkoxycarbonyl, (C.sub.2-C.sub.3) alkenyl, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3) alkynyl, (C.sub.2-C.sub.3)-haloalkynyl, (C.sub.1-C.sub.3)-alkylthio, (C.sub.1-C.sub.3)-alkylsulfinyl, or (C.sub.1-C.sub.3)-alkylsulfonyl; R.sup.6 is hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, or (C.sub.1-C.sub.3)-haloalkoxy; R.sup.7 and R.sup.8 form, together with the carbon atom to which they are bound, a saturated or partially unsaturated three-, four-, five-, six-, seven- or eight-membered monocyclic or bicyclic carbocyclic ring W, where one carbon ring atom bears p oxo groups, and where the ring is substituted by n radicals R.sup.g; R.sup.9 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.4)-cycloalkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, or (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkoxy; X is a bond (X.sup.0) or a divalent unit selected from the group consisting of (X.sup.1), (X.sup.2), (X.sup.3), (X.sup.4), (X.sup.5), and (X.sup.6): ##STR00194## R.sup.10, R.sup.11, R.sup.12, R.sup.13, R.sup.14 and R.sup.15 are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO.sub.2R.sup.e, CONR.sup.bR.sup.d, R.sup.a, or (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.5)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, where the four last-mentioned aliphatic and cycloaliphatic radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano; or (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-cycloalkoxy, (C.sub.3-C.sub.6)-alkenyloxy or (C.sub.3-C.sub.6)-alkynyloxy, where the aliphatic and cycloaliphatic moieties in the four last-mentioned radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C.sub.1-C.sub.2)-alkoxy; Y is hydrogen, cyano, hydroxyl, Z, or is (C.sub.1-C.sub.12)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.2-C.sub.12)-alkenyl or (C.sub.2-C.sub.12)-alkynyl, where the four last-mentioned aliphatic and cycloaliphatic radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR.sup.d, Z, OZ, NHZ, S(O).sub.nR.sup.a, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, CO.sub.2R.sup.e, CONR.sup.bR.sup.h, COR.sup.b, CONR.sup.eSO.sub.2R.sup.a, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.bCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.bSO.sub.2NR.sup.bR.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.fR.sup.f and C(R.sup.b)NOR.sup.e; Z is a three-, four-, five-, six- or seven-membered saturated, partly unsaturated, fully unsaturated or aromatic ring, except phenyl, which is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and which is substituted by m radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, COR.sup.b, CONR.sup.eSO.sub.2R.sup.a, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.bCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.bSO.sub.2NR.sup.bR.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.fR.sup.f, C(R.sup.b)NOR.sup.e, R.sup.b, R.sup.c, R.sup.e and R.sup.f, and where the sulfur and carbon ring atoms bear n oxo groups; each R.sup.a is independently (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.4)-alkynyl or (C.sub.3-C.sub.6)-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C.sub.1-C.sub.3)-alkoxy; each R.sup.b is independently hydrogen or R.sup.a; each R.sup.c is independently fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O).sub.nR.sup.a or (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-alkenyloxy or (C.sub.3-C.sub.6)-alkynyloxy, where aliphatic moieties in the three last-mentioned radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (C.sub.1-C.sub.2)-alkoxy; each R.sup.d is independently hydrogen or (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.4)-alkenyl, phenyl-(C.sub.1-C.sub.3)-alkyl or (C.sub.2-C.sub.4)-alkynyl, where the five last-mentioned radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, (C.sub.1-C.sub.2)-alkoxy, (C.sub.1-C.sub.3)-alkylsulfinyl, (C.sub.1-C.sub.3)-alkylsulfonyl, (C.sub.1-C.sub.3)-alkylthio, phenylthio, phenylsulfinyl and phenylsulfonyl; each R.sup.e has independently one of the meanings given for R.sup.d; each R.sup.f is independently (C.sub.1-C.sub.3)-alkyl or (C.sub.1-C.sub.3)-alkoxy; each R.sup.g is independently halogen, nitro, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, hydroxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.5)-cycloalkyl, (C.sub.3-C.sub.5)-halocycloalkyl, hydroxy-(C.sub.3-C.sub.5)-cycloalkyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy, (C.sub.1-C.sub.3)-alkoxycarbonyl, (C.sub.2-C.sub.3) alkenyl, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3) alkynyl, (C.sub.2-C.sub.3)-haloalkynyl, (C.sub.1-C.sub.3)-alkylthio, (C.sub.1-C.sub.3)-alkylsulfinyl, (C.sub.1-C.sub.3)-alkylsulfonyl; each R.sup.h is independently hydrogen or (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.2)-alkoxy, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, or (C.sub.2-C.sub.4)-alkynyl each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (C.sub.1-C.sub.2)-alkoxy; each m is independently 0, 1, 2, 3, 4 or 5; each n is independently 0, 1 or 2; each p is independently 0 or 1; each r is independently 1, 2, 3, 4, 5, 6 or 7; including their agriculturally acceptable salts, stereoisomers and tautomers; except for following compounds: glycine, N-[[1-[[(4-fluorophenyl)amino]carbonyl]cyclopropyl]carbonyl]-; L-alanine, N-[[1-[[(4-fluorophenyl)amino]carbonyl]cyclopropyl]carbonyl]-; D-alanine, N-[[1-[[(4-fluorophenyl)amino]carbonyl]cyclopropyl]carbonyl]; D-leucine, N-[[1-[[(4-fluorophenyl)amino]carbonyl]cyclopropyl]carbonyl]-; ethyl 4-[[1-(phenylcarbamoyl)cyclopropanecarbonyl]amino]piperidine-1-carboxylate; butanoic acid, 4-[[[1-[[4-fluorophenyl)amino)carbonyl]cyclopropyl]carbonyl]methylamino]-; -alanine, N-[[1-[[(4-fluorophenyl)amino]carbonyl]cyclopropyl]carbonyl]-N-methyl-; heptanoic acid, 7-[[[1-[[(4-fluorophenyl)amino]carbonyl]cyclopropyl]carbonyl]amino]-; cyclohexanecarboxylic acid, 4-[[[1-[[(4-fluorophenyl)amino]carbonyl]cyclopropyl]carbonyl]amino]; N-(1,1-dioxothiolan-3-yl)-N-phenylcyclopropane-1,1-dicarboxamide; N-phenyl-N-quinolin-8-ylcyclopropane-1,1-dicarboxamide; N-(5-methyl-1,2-oxazol-3-yl)-N-phenylcyclopropane-1,1-dicarboxamide; N1-(4-fluorophenyl)-N1-methylcyclopropane-1,1-dicarboxamide; N1-cyclopropyl-N[4(4-ethoxyphenyl)methyl]-N1-methylcyclopropane-1,1-dicarboxamide; N1-methyl-N1-[3-(trifluoromethyl)phenyl]cyclopropane-1,1-dicarboxamide; N-tert-butyl-N-phenylcyclopropane-1,1-dicarboxamide; N-(3-methylbutyl)-N-phenylcyclopropane-1,1-dicarboxamide; N-pentyl-N-phenylcyclopropane-1,1-dicarboxamide; N-phenyl-N-prop-2-enylcyclopropane-1,1-dicarboxamide; N-(2-methylpropyl)-N-phenylcyclopropane-1,1-dicarboxamide; N-butyl-N-phenylcyclopropane-1,1-dicarboxamide; N-(2-methylpropyl)-N-phenylcyclopropane-1,1-dicarboxamide; N-butan-2-yl-N-phenylcyclopropane-1,1-dicarboxamide; N-phenyl-N-propylcyclopropane-1,1-dicarboxamide; N-phenyl-N-propan-2-ylcyclopropane-1,1-dicarboxamide; N-cycloheptyl-N-phenylcyclopropane-1,1-dicarboxamide; N-cyclopentyl-N-phenylcyclopropane-1,1-dicarboxamide; N-cyclohexyl-N-phenylcyclopropane-1,1-dicarboxamide; N-cyclopropyl-N-phenylcyclopropane-1,1-dicarboxamide; 1,1-cyclopropanedicarboxamide,N-phenyl-N-[(tetrahydro-2-furanyl)methyl]; ethyl 4-[[1-(phenylcarbamoyl)cyclopropanecarbonyl)amino) piperidine-1-carboxylate; ethyl 4-[[1-(3-methylphenylcarbamoyl)cyclopropanecarbonyl)amino)piperidine-1-carboxylate; ethyl 4-[[1-(4-ethylphenylcarbamoyl)cyclopropanecarbonyl)amino)piperidine-1-carboxylate; ethyl 4-[[1-(3,5-dimethylphenylcarbamoyl)cyclopropanecarbonyl)amino) piperidine-1-carboxylate; methyl 2-[[1-[(2,6-difluorophenyl)carbamoyl]cyclopropanecarbonyl]amino]-5-isopropyl-thiazole-4-carboxylate; benzoic acid, 4-[[[1-[(methylamino)carbonyl]cyclobutyl]carbonyl]amino]-.

2. The compounds as claimed in claim 1, wherein Z is a three-, four-, five-, six- or seven-membered saturated, partly unsaturated or fully unsaturated non-aromatic ring which is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and which is substituted by m radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, COR.sup.b, CONR.sup.eSO.sub.2R.sup.a, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.bCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.bSO.sub.2NR.sup.bR.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.fR.sup.f and C(R.sup.b)NOR.sup.e, R.sup.b, R.sup.c, R.sup.e and R.sup.f, and where the sulfur and carbon ring atoms bear n oxo groups.

3. The compounds as claimed in claim 1 or 2, wherein the substituents have the following meaning: R.sup.1 is hydrogen; R.sup.9 is hydrogen.

4. The compounds as claimed in any one of claims 1 to 3, wherein the substituents have the following meaning: R.sup.2 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl; R.sup.6 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl; where preferably R.sup.2 is hydrogen and R.sup.6 is hydrogen.

5. The compounds as claimed in any one of claims 1 to 4, wherein the substituents have the following meaning: R.sup.3 is hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; R.sup.5 is hydrogen, halogen, hydroxyl, cyano, or (C.sub.1-C.sub.3)-alkyl; where preferably R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; R.sup.5 is hydrogen or halogen.

6. The compounds as claimed in any one of claims 1 to 5, wherein the substituents have the following meaning: R.sup.4 is hydrogen or halogen; preferably hydrogen.

7. The compounds as claimed in any one of claims 1 to 6, wherein the substituents have the following meaning: R.sup.7 and R.sup.8 form, together with the carbon atom to which they are bound, a saturated or partially unsaturated three-, four- or five-membered monocyclic carbocyclic ring W.

8. The compounds as claimed in any one of claims 1 to 7, wherein the substituents have the following meaning: X is a bond or a group (X.sup.1), where R.sup.10 and R.sup.11 are each independently hydrogen or methyl.

9. The compounds as claimed in any one of claims 1 to 8, wherein the substituents have the following meaning: X is a bond; and Y is (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.2-C.sub.8)-alkenyl or (C.sub.2-C.sub.8)-alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR.sup.d, Z, OZ, NHZ, S(O).sub.nR.sup.a, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, CO.sub.2R.sup.e, CONR.sup.bR.sup.h, COR.sup.b, CONR.sup.eSO.sub.2R.sup.a, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.bCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e NR.sup.bSO.sub.2NR.sup.bR.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.fR.sup.f and C(R.sup.b)NOR.sup.e; where Y is preferably (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.2-C.sub.8)-alkenyl or (C.sub.2-C.sub.8)-alkynyl, each substituted by one or two radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h and CONR.sup.eSO.sub.2R.sup.a, and m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR.sup.d, Z, OZ and NHZ.

10. The compounds as claimed in claim 9, where Y is (C.sub.1-C.sub.6)-alkyl substituted by a radical CO.sub.2R.sup.e; where R.sup.e is hydrogen or preferably (C.sub.1-C.sub.4)-alkyl.

11. The compounds as claimed in any one of claims 1 to 8, wherein the substituents have the following meaning: X is a bond or a group (X.sup.1), where R.sup.10 and R.sup.11 are each independently hydrogen or methyl; Y is Z; and Z is a three-, four-, five-, six- or seven-membered saturated or partly unsaturated ring which is formed from r carbon atoms and n oxygen atoms, each substituted by m radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eSO.sub.2R.sup.a, R.sup.b, R.sup.c, R.sup.e and R.sup.f; where Z is preferably a three-, four-, five-, six- or seven-membered saturated or partly unsaturated ring which is formed from 2, 3, 4, 5, 6 or 7 carbon atoms and 0, 1 or 2 oxygen atoms, each substituted by one or two radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h and CONR.sup.eSO.sub.2R.sup.a and 0 or 1 radicals selected from the group consisting of R.sup.b, R.sup.c, R.sup.e and R.sup.f.

12. The compounds as claimed in claim 11, where X is a bond or a group CH.sub.2; and Z is a three-, four-, five-, six- or seven-membered saturated or partly unsaturated carbocyclic ring which is substituted by a radical CO.sub.2R.sup.e; where R.sup.e is preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; where in particular X is a bond and Z is a five-membered partly unsaturated carbocyclic ring which is substituted by a radical CO.sub.2R.sup.e; where R.sup.e is hydrogen or preferably (C.sub.1-C.sub.4)-alkyl.

13. The compounds as claimed in any one of claims 1 to 12, wherein the substituents have the following meaning: R.sup.1 is hydrogen; R.sup.2 is hydrogen; R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; R.sup.4 is hydrogen; R.sup.5 is hydrogen or halogen; R.sup.6 is hydrogen; R.sup.7 and R.sup.8 form, together with the carbon atom to which they are bound, a saturated or partially unsaturated three-, four- or five-membered monocyclic carbocyclic ring W; R.sup.9 is hydrogen; X is a bond or a group (X.sup.1), where R.sup.10 and R.sup.11 are each independently hydrogen or methyl; Y is Z, or (C.sub.1-C.sub.8)-alkyl substituted by a radical CO.sub.2R.sup.e; Z is a three-, four-, five-, six- or seven-membered saturated or partly unsaturated carbocyclic ring which is substituted by a radical CO.sub.2R.sup.e; and R.sup.e is hydrogen or (C.sub.1-C.sub.8)-alkyl; where preferably R.sup.1 is hydrogen; R.sup.2 is hydrogen; R.sup.3 is halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; specifically halogen; R.sup.4 is hydrogen; R.sup.5 is hydrogen or halogen; R.sup.6 is hydrogen; R.sup.7 and R.sup.8 form, together with the carbon atom to which they are bound, a saturated or partially unsaturated three-, four- or five-membered monocyclic carbocyclic ring W; R.sup.9 is hydrogen; X is a bond; Y is Z, or C(R.sup.101)(R.sup.111)C.sub.1-C.sub.4-alkyl substituted by a radical CO.sub.2R.sup.e; Z is a five-membered saturated or partly unsaturated carbocyclic ring which is substituted by a radical CO.sub.2R.sup.e; R.sup.e is hydrogen or (C.sub.1-C.sub.8)-alkyl; and one of R.sup.101 and R.sup.111 is hydrogen and the other is hydrogen or methyl.

14. A composition comprising at least one compound as claimed in any one of claims 1 to 13, and at least one auxiliary, which is customary for formulating crop protection compounds.

15. The composition as claimed in claim 14, comprising a further herbicide.

16. The use of a compound as claimed in any one of claims 1 to 13, or a composition as claimed in claim 14 or 15 for controlling unwanted vegetation.

17. A method for controlling unwanted vegetation which comprises allowing a herbicidally effective amount of at least one compound as claimed in any one of claims 1 to 13, or a composition as claimed in claim 14 or 15 to act on plants, their seed and/or their habitat.

Description

EXAMPLES

A Chemistry Examples

[0851] Chemical bonds, drawn as bars in chemical formulae, indicate the relative stereochemistry on the ring system.

Example 1: Synthesis of methyl (1S,4R)-4-{1-[(3,5-difluorophenyl)carbamoyl]cyclopropaneamido}cyclopent-2-ene-1-carboxylate (Cpd I.2)

[0852] ##STR00133##

[0853] To a solution of 1-[[(3,5-difluorophenyl)amino]carbonyl]cyclopropanecarboxylic acid (1) (18 mg, 0.075 mmol) (CAS: 1270737-04-6) in dimethylformamide (DMF) methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride (2, CAS [180196-56-9]) (15 mg, 0.082 mmol) was added. To the resulting solution was added HATU (2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, CAS [148893-10-1]), (31 mg, 0.082 mmol) and then diisopropylethylamine (38 L, 0.22 mmol). The resulting reaction mixture was stirred at room temperature overnight. To the reaction mixture water and sodium bicarbonate solution were added. The reaction mixture was extracted with ethyl acetate, washed with water, dried (sodium sulfate) and the solvent was evaporated under reduced pressure. The crude product was purified by prep-HPLC (acetonitrile/water) yielding compound I.2 (20 mg, 73%).

[0854] .sup.1H NMR (400 MHz, chloroform-d) 11.67 (s, 1H), 7.23-7.14 (m, 2H), 6.57-6.44 (m, 2H), 5.98-5.90 (m, 2H), 5.07-4.96 (m, 1H), 3.73 (s, 3H), 3.53 (dd, J=8.3, 2.2 Hz, 1H), 2.34 (dt, J=14.1, 8.1 Hz, 1H), 1.88 (d, J=14.2 Hz, 1H), 1.80-1.73 (m, 2H), 1.42-1.34 (m, 1H), 1.35-1.27 (m, 1H).

[0855] High Performance Liquid Chromatography: HPLC-column Kinetex XB C18 1.7 (502.1 mm); eluent: acetonitrile/water+0.1% trifluoroacetic acid (gradient from 5:95 to 100:0 in 1.5 min at 60 C., flow gradient from 0.8 to 1.0 ml/min in 1.5 min).

[0856] In analogy to the examples described above, the following compounds of formula (I) were prepared, wherein R.sup.1 is hydrogen, and W is formed by R.sup.7 and R.sup.8 together with the carbon atom to which they are bound, starting from commercially available diesters and using commercially available amines:

##STR00134##

TABLE-US-00002 TABLE 2 HPLC/MS = MassChargeRatio HPLC/ Cpd. R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.6 W R.sup.9 N*-X-Y MS I.1 H Cl H Cl H [00135] H [00136] 387.0 I.2 H F H F H [00137] H [00138] 364.8 I.3 H I H H H [00139] H [00140] 454.8 I.4 H I H H H [00141] H [00142] 430.8 I.5 H Cl H H H [00143] H [00144] 339.0 I.6 H CH.sub.3 H F H [00145] H [00146] 360.9 I.7 H Cl H H H [00147] H [00148] 362.9 I.8 H CH.sub.2CH.sub.3 H H H [00149] H [00150] 347.1 I.9 H CH.sub.2CH.sub.3 H H H [00151] H [00152] 333.0 I.10 H CH.sub.2CH.sub.3 H H H [00153] H [00154] 357.0 I.11 H OCF.sub.3 H H H [00155] H [00156] 403.2 I.12 H OCF.sub.3 H H H [00157] H [00158] 389.2 I.13 H OCF.sub.3 H H H [00159] H [00160] 413.2 I.14 H Cl H Cl H [00161] H [00162] 398.7 I.15 H Cl H Cl H [00163] H [00164] 398.7 I.16 H Cl H F H [00165] H [00166] 356.9 I.17 H F H F H [00167] H [00168] 341.1 I.18 H Cl H Cl H [00169] H [00170] 373.1 I.19 H F H H H [00171] H [00172] 323.1 I.20 H F H H H [00173] H [00174] 347.1 I.21 H CH.sub.3 H F H [00175] H [00176] 337.1 I.22 H Cl H Cl H [00177] H [00178] 384.8 I.23 H Cl H Cl H [00179] H [00180] 384.8 I.24 H Cl H Cl H [00181] H [00182] 386.8 I.25 H Cl H Cl H [00183] H [00184] 426.8 I.26 H Cl H Cl H [00185] H [00186] 372.7 I.27 H Cl H Cl H [00187] H [00188] 412.8 I.28 H Cl H Cl H [00189] H [00190] 372.7 I.29 H Cl H Cl H [00191] H [00192] 398.8

B Use Examples

[0857] The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiments:

[0858] The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

[0859] For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the test plants had rooted. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients. For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

[0860] Depending on the species, the test plants were kept at 10-25 C. or 20-35 C., respectively. The test period extended over 2 to 4 weeks. During this time, the test plants were tended, and their response to the individual treatments was evaluated.

[0861] Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the test plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of 65 to 90 and a very good herbicidal activity is given at values of 90 to 100.

[0862] The test plants used in the greenhouse experiments were of the following species:

TABLE-US-00003 Bayer code Scientific name ABUTH Abutilon theophrasti ALOMY Alopercurus myosuroides APESV Apera spica-venti AVEFA Avena fatua ECHCG Echinocloa crus-galli SETVI Setaria viridis

[0863] At an application rate of 0.500 kg/ha, applied by the pre-emergence method: [0864] compound I.1 showed very good herbicidal activity against APESV.

[0865] At an application rate of 0.500 kg/ha, applied by the post-emergence method: [0866] compound I.1 showed good herbicidal activity against ALOMY. [0867] compound I.1 showed good herbicidal activity against AVEFA. [0868] compound I.1 showed good herbicidal activity against SETVI.

[0869] At an application rate of 0.250 kg/ha, applied by the post-emergence method: [0870] compounds I.11, I.13 showed good herbicidal activity against ALOMY. [0871] compounds I.3, I.5, I.6, I.7, I.11, I.13, I.15 showed good herbicidal activity against AVEFA. [0872] compounds I.6, I.7, I.12 showed good herbicidal activity against ECHCG.

[0873] At an application rate of 0.125 kg/ha, applied by the post-emergence method: [0874] compound I.2 showed very good herbicidal activity against AVEFA. [0875] compound I.2 showed very good herbicidal activity against ALOMY. [0876] compound I.2 showed good herbicidal activity against ABUTH.