Patent EA-001144-B1 (EA)
Title: 3-aryluracils and use thereof
Inventor: KLINTZ RALF
IPC: A01N43/84
Filed: 1996-03-01
Abstract: 1. A 3-aryluracil of the general formula I    where the variables have the following meanings:  A is hydrogen, methyl or amino; R<1> is hydrogen or halogen; R<2> is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylthio, C1-C6-alkylsulfenyl or C1-C6-alkylsulfonyl; R<3> is hydrogen, halogen or C1-C6-alkyl; X is oxygen or -N(R<7>)-, R<7> being hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, (C1-C6-alkyl)carbonyl or C1-C6-alkoxy- C1-C6-alkyl; Y<1> and Y<2> independently of one another are oxygen or sulfur; Z is oxygen or -N(R<8>)-;  R<5>, R<6> and R<8> independently of one another are hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl or C1-C6-alkoxy- C1-C6-alkyl; or R<6> and R<8> together are a second chemical bond;  R<4> is hydrogen, C1-C6-alkyl, C3-C8-cycloalkyl, C1-C6-halo-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, (C1-C6-alkyl)-carbonyl, (C3-C6- alkenyl)carbonyl, (C3-C6-alkynyl)carbonyl or C1-C6-alkylsulfonyl, it being possible for each of the last-mentioned 9 radicals to carry, if desired, one to three substituents, in each case selected from the group consisting of  - halogen, nitro, cyano, hydroxyl, C3-C8-cycloalkyl, C1-C6-alkoxy, C3-C8- cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C6-alkoxy- C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfenyl, C1-C6-alkyl-sulfonyl, C1-C6-alkylideneaminooxy,  - the phenyl, phenoxy or phenylsulfonyl group, which can be unsubstituted or can carry one to three radicals, in each case selected from the group consisting of halogen, nitro, cyano, C1-C6-alkyl, C1-C6-alkoxy and C1-C6-haloalkyl,  - a 3- to 7-membered heterocyclyl, heterocyclyloxy, heterocyclylcarbonyl or heterocyclylcarbonyloxy group having one to three hetero atoms as ring members, selected from the group consisting of two oxygen atoms, two sulfur atoms and 3 nitrogen atoms, it being possible for the heterocycle to be saturated, partially or completely unsaturated or aromatic and, if desired, to carry one to three substituents, in each case selected from the group consisting of halogen, nitro, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl and (C1-C6-alkyl)carbonyl,  - a group -CO-R<9>, -O-CO-R<9>, -CO-OR<9>, -O-CO-OR<9>, -CO-SR<9>, -O-CO-SR<9>, -CO-N(R<9>)R<10>, -O-CO-N(R<9>)R<10>, -N(R<9>)R<10> or -C(NR<11>)-OR<12>,  R<9> being hydrogen, C1-C6-alkyl, C3-C8-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy- C1-C6-alkyl, (C1-C6-alkoxy)carbonyl- C1-C6-alkyl, phenyl or phenyl- C1-C6-alkyl, it being possible for the phenyl radicals to be unsubstituted or to carry one to three radicals, in each case selected from the group consisting of halogen, nitro, cyano, C1-C6-alkyl, C1-C6-alkoxy and C1-C6-haloalkyl,  R<10> being hydrogen, hydroxyl, C1-C6-alkyl, C3-C8-cycloalkyl, C1-C6-alkoxy, C3-C6-alkenyloxy or (C1-C6-alkoxy)-carbonyl- C1-C6-alkoxy,  R<11> being C1-C6-alkoxy, C3-C6-alkenyloxy or (C1-C6-alkoxy)-carbonyl- C1-C6-alkoxy and  R<12> being C1-C6-alkyl, C3-C6-alkenyl or (C1-C6-alkoxy)-carbonyl- C1-C6-alkyl and the agriculturally utilizable salts of those compounds I in which A is hydrogen. 2. A 3-aryluracil of the formula I as claimed in claim 1, the variables having the following meanings:  A is amino or methyl; R<1> is hydrogen, fluorine or chlorine; R<2> is halogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkylsulfonyl; R<3> is hydrogen or halogen; X is oxygen or -N(R<7>)-, R<7> being hydrogen or C1-C6-alkyl; Y<1> and Y<2> are oxygen; Z is oxygen or -N(R<8>)-; R<5>, R<6> and R<8> independently of one another are hydrogen or C1-C6-alkyl, or R<6> and R<8> together are a second chemical bond;  R<4> is hydrogen, C1-C6-alkyl, C3-C8-cycloalkyl, C1-C6-halo-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, (C1-C6-alkyl)-carbonyl, (C3-C6-alkenyl)carbonyl, (C3-C6-alkynyl)carbonyl or C1-C6-alkylsulfonyl, it being possible for each of the last-mentioned 9 radicals, if desired, additionally to carry one or two substituents, in each case selected from the group consisting of  - halogen, nitro, cyano, hydroxyl, C3-C8-cycloalkyl, C1-C6-alkoxy, C3-C8-cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C6-alkoxy- C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfenyl, C1-C6-alkylsulfonyl, -alkylideneaminooxy,  - a 3- to 7-membered heterocyclyl, heterocyclyloxy, heterocyclylcarbonyl or heterocyclylcarbonyloxy group having one to three hetero atoms as ring members, selected from the group consisting of two oxygen atoms, two sulfur atoms and 3 nitrogen atoms, it being possible for the heterocycle to be saturated, partially or completely unsaturated or aromatic and, if desired, to carry one to three substituents, in each case selected from the group consisting of halogen, nitro, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl and (C1-C6-alkyl)carbonyl,  - a group -CO-R<9>, -O-CO-R<9>, -CO-OR<9>, -O-CO-OR<9>, -CO-SR<9>, -O-CO-SR<9>, -CO-N(R<9>)R<10>, -O-CO-N(R<9>)R<10>, -N(R<9>)R<10> or -C(NR<11>)-OR<12>, where R<9> being hydrogen, C1-C6-alkyl, C3-C8-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy- C1-C6-alkyl or (C1-C6-alkoxy)carbonyl- C1-C6-alkyl,  R<10> being hydrogen, hydroxyl, C1-C6-alkyl, C3-C8-cycloalkyl or C1-C6-alkoxy,  R<11> being C1-C6-alkoxy or C3-C6-alkenyloxy and  R<12> being (C1-C6-alkoxy)carbonyl- C1-C6-alkyl. 3. A 3-aryluracil of the formula I as claimed in claim 1, X being oxygen. 4. A 3-aryluracil of the formula I as claimed in claim 1, X being -N(R<7>)-. 5. A 3-aryluracil of the formula I as claimed in claim 1, Z being oxygen. 6. A 3-aryluracil of the formula I as claimed in claim 1, Z being -N(R<8>)-. 7. A 3-aryluracil of the formula I as claimed in claim 1, Z being -N(R<8>)- and R<8> together with R<6> being a second chemical bond. 8. A 3-aryluracil of the formula I as claimed in claim 1,Y<1> being oxygen. 9. A 3-aryluracil of the formula I as claimed in claim 1, R<2> being trifluoromethyl, chlorodifluoromethyl or pentafluoroethyl. 10. A herbicidal composition comprising a herbicidally active amount of at least one 3-aryluracil of the formula I or an agriculturally utilizable salt of I, as claimed in claim 1, and at least one inert liquid and/or solid carrier and, if desired, at least one surfactant. 11. A method of controlling undesired vegetation, which comprises allowing a herbicidally active amount of at least one 3-aryl-uracil of the formula I or of an agriculturally utilizable salt of I, as claimed in claim 1, to act on plants, their habitat or on seeds.