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US 4,902,336 AGranted
Herbicidal compositions
AssigneeCiba-Geigy Corporation
InventorWerner Topfl
Life of this patent
Estimating the term…
Abstract
N-Arylsulfonyl-N'-(4-mercaptomethyl-pyrimidinyl-ureas of the formula ##STR1## (symbols in this formula defined herein) and the salts of these compounds with amines, alkali metal bases or alkaline-earth metal bases or with ammonium bases, have good pre- and post-emergence-selective, herbicidal and growth-regulating properties.
Claims20
An N-arylsulfonyl-N'-(4-mercaptomethylpyrimidinyl-urea of the formula I ##STR110## wherein E is --CH.dbd.,
- X is oxygen, sulfur, --NR.sup.3 --, --N.dbd.CR.sup.3 --, --CH.dbd.CH-- or ##STR111## Z is oxygen or sulfur, R.sup.1 is hydrogen, halogen, nitro, ethinyl, --NR.sup.16 R.sup.17, --CR.sup.6 --di-C.sub.1 -C.sub.4 -alkoxy, ##STR112## --CW--R.sup.6, --SO.sub.2 --NR.sup.7 R.sup.8, --CO--R.sup.9, --Y.sub.m --R.sup.10, --SO.sub.2 --R.sup.11 or O--SO.sub.2 R.sup.12, in which m is zero or 1,
- R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl or nitro,
- R.sup.3 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkenyl or C.sub.1 -C.sub.4 -alkoxy,
- R.sup.4 is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.2 -C.sub.4 -alkoxyalkyl, C.sub.2 -C.sub.4 -alkoxyalkoxy, cyclopropyl, --NH.sub.2, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, or a saturated 5- to 7-membered nitrogen heterocycle selected from pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine and hexamethyleneimine,
- R.sup.5 is cyano, --CZ--R.sup.13, ##STR113## or an unsaturated heterocycle selected from imidazole, triazole, pyridine, pyrimidine, thiazole, oxazole, thiadiazole, oxadiazole, pyridazine, thiophene or furan, as well as partially unsaturated derivatives thereof which are unsubstituted or substituted by a radical selected from the group comprising:
- halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -haloalkyl,
- R.sup.6 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.4 -C.sub.7 -cycloalkylalkyl or C.sub.2 -C.sub.4 -alkoxyalkyl,
- R.sup.7 and R.sup.16 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -cyanoalkyl or C.sub.1 -C.sub.4 -alkoxy,
- R.sup.8 and R.sup.17 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkenyl or C.sub.1 -C.sub.4 -alkoxy, or
- R.sup.7 and R.sup.8 as well as R.sup.16 and R.sup.17 independently of one another form, together with the nitrogen atom binding them, a 5- to 7-membered saturated nitrogen heterocycle selected from pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine and hexamethyleneimine,
- R.sup.9 is C.sub.1 -C.sub.4 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkinyloxy, C.sub.2 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.4 -cyanoalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.3 -C.sub.4 -alkenylthio, C.sub.3 -C.sub.4 -alkinylthio, C.sub.5 -C.sub.6 -cycloalkoxy, C.sub.4 -C.sub.7 -cycloalkylalkoxy, --NR.sup.7 R.sup.8 or C.sub.2 -C.sub.6 -alkoxyalkoxy,
- R.sup.10 is C.sub.3 -C.sub.4 -alkinyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl mono- or polysubstituted by halogen, cyano, C.sub.1 -C.sub.4 -alkoxy or --SO.sub.n --C.sub.1 -C.sub.4 -alkyl, or is C.sub.1 -C.sub.4 -alkyl mono- or polysubstituted by halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -haloalkylthio, --SO.sub.n --C.sub.1 -C.sub.4 -alkyl, --T--CX--R.sup.18, ##STR114## --CO--R.sup.6, --CO--R.sup.9 or --SO.sub.2 --NR.sup.7 R.sup.8, in which n is zero, 1 or 2,
- R.sup.11 is C.sub.2 -C.sub.4 -haloalkoxy,
- R.sup.12 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl or --NR.sup.16 R.sup.17,
- R.sup.13 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, phenyl, di-C.sub.1 -C.sub.4 -alkylamino, or a saturated 5- to 7-membered nitrogen heterocycle selected from pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine and hexamethyleneimine,
- R.sup.14 and R.sup.15 independently of one another are C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.3 -C.sub.4 -alkoxyalkoxy, C.sub.3 -C.sub.4 -alkenyloxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.4 -alkylamino or di-C.sub.1 -C.sub.4 -alkylamino,
- R.sup.18 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or --NR.sup.16 R.sup.17,
- T is oxygen or sulfur,
- W is oxygen or .dbd.N--O--R.sup.3, and
- Y is oxygen, sulfur, --SO-- or --SO.sub.2 --;
- or a salt of said compound.
18 more elements
Dependencies are inferred from the claim text.