摘要:
There is described a process for producing sulfonylureas of the formula ##STR1## wherein G is an unsubstituted or substituted furanyl, thienyl, pyrrolyl, pyridinyl or phenyl radical,X is alkyl, haloalkyl, alkoxy, alkylthio, halogen, haloalkoxy, alkylamino or dialkylamino,Y is alkyl, alkoxy or haloalkoxy,Z is a nitrogen atom or the methyne group --CH.dbd..This novel process comprises reacting a sulfonamide of the formulaG--SO.sub.2 --NH.sub.2,in the presence of a base, with a chloroformic acid ester of the formulaCl--CO--Q--T,or a sulfonyl chloride of the formulaG--SO.sub.2 Cl,in the presence of a base, with a urethane of the formulaH.sub.2 N--CO--Q--T;and converting the formed carbamate of the formulaG--SO.sub.2 --NH--CO--Q--Tby reaction with an amine of the formula ##STR2## into the sulfonylurea of the above formula. There are also described novel sulfonylcarbamates of the above formula as intermediates.
摘要:
N-Phenylsulfonyl-N'-pyrimidinyl- and -triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, with alkali or alkaline-earth metal bases or with quaternary ammonium bases, have good pre- and post-emergence selective, herbicidal and growth-regulating properties.The symbols in this formula are as follows:A is a C.sub.3 -C.sub.6 -alkynyl group,E is the methine group or nitrogen,X is oxygen, sulfur or a sulfinyl or sulfonyl bridge,Z is oxygen or sulfur,m is the number one or two,R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.5 -alkyl or C.sub.2 -C.sub.5 -alkenyl or a group --Y--R.sub.5,R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.5 -alkyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.1 -C.sub.4 -haloalkyl, or a group --Y--R.sub.5, --COOR.sub.6, --NO.sub.2 or --CO--NR.sub.7 --R.sub.8,R.sub.3 and R.sub.4 independently of one another are each hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, halogen or alkoxyalkyl having at most 4 carbon atoms,R.sub.5 and R.sub.6 are each C.sub.1 -C.sub.5 -alkyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.2 -C.sub.6 -alkynyl,R.sub.7 and R.sub.8 independently of one another are each hydrogen, C.sub.1 -C.sub.5 -alkyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.2 -C.sub.6 -alkynyl, andY is oxygen, sulfur or a sulfinyl or sulfonyl bridge.
摘要:
N-Phenylsulfonyl-N'-triazinylureas of the general formula ##STR1## and the salts thereof with amines, alkali metal or alkaline earth metal bases or with quaternary ammonium bases, have good pre- and postemergence selective herbicidal and growth regulating properties. In the above formulaA is a C.sub.1 -C.sub.6 alkyl radical which is substituted by C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl,X is oxygen, sulfur, a sulfinyl or sulfonyl bridge,Z is oxygen or sulfur,m is 1 or 2,R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.1 -C.sub.4 haloalkyl, or a radical --Y--R.sub.5, --COOR.sub.6, --NO.sub.2 or --CO--NR.sub.7 --R.sub.8,R.sub.3 and R.sub.4, each independently of the other, are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, halogen or alkoxyalkyl or at most 4 carbon atoms,R.sub.5 and R.sub.6, each independently of the other, are C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or C.sub.2 -C.sub.6 alkynyl,R.sub.7 and R.sub.8, each independently of the other, are hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or C.sub.2 -C.sub.6 alkynyl, andY is oxygen, sulfur, a sulfinyl or sulfonyl bridge.
摘要:
N-Phenylsulfonyl N'-triazinylureas and -thioureas of formula I ##STR1## in which X is oxygen, sulfur, SO or SO.sub.2 ; W is oxygen or sulfur; R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen, fluorine, chlorine, bromine, iodine, (X).sub.n R.sub.3, NO.sub.2, NR.sub.4 R.sub.5, --C.tbd.CR.sub.6, ##STR2## or cyano; n is the number 0 or 1; R.sub.3 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl which is substituted by 1-4 halogen atoms, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio; or C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkenyl which is substituted by 1-4 halogen atoms; R.sub.4 is hydrogen, CH.sub.3 O, CH.sub.3 CH.sub.2 O or C.sub.1 -C.sub.3 alkyl; R.sub.5 is hydrogen or C.sub.1 -C.sub.3 alkyl; R.sub.6 is hydrogen, methyl or ethyl; R.sub.7 is hydrogen or methyl; Z is ##STR3## E is nitrogen; R.sub.8 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino and R.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, C.sub.2 -C.sub.5 alkylthioalkyl or cyclopropyl, and the salts of these compounds with amines, alkali metal or alkaline earth metal bases or quaternary ammonium bases have good pre- and postemergence selective herbicidal and growth-regulating properties.
摘要:
A 2-(2-halogenoethylthio)-phenylsulfonamide of the formula I ##STR1## in which Z.sub.1 and Z.sub.2 independently of one another are hydrogen, fluorine or chlorine, is prepared by a process wherein:a) a 2-halogenophenylsulfonamide of the formula II ##STR2## in which X is fluorine, chlorine or bromine, is converted, in the presence of a base, together with a mercaptan of the formula IIIR-SH (III) in which R is C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkyl substituted by phenyl, into a 2-sulfenylphenylsulfonamide,b) this compound is oxidized to give the 2-sulfinylphenylsulfonamide,c) the resulting 2-sulfinylphenylsulfonamide is converted, in the presence of an acid, into the disulfide of the formula VI ##STR3## d) the disulfide of the formula VI is reduced to the 2-mercaptophenylsulfonamide,e) this compound is then converted, by means of a trialkylamine of the formula X(R.sub.1).sub.3 N (X) in which R.sub.1 is C.sub.1 -C.sub.4 alkyl, into the 2-mercaptophenylsulfonamide trialkylamine salt, andf) this compound is then reacted with a halogenofluoroethane of the formula IXY-CH.sub.2 CFZ.sub.1 Z.sub.2 (IX) in which Y is chlorine or bromine and Z.sub.1 and Z.sub.2 independently of one another are hydrogen, fluorine or chlorine.
摘要:
N-phenylsulfonyl-N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal or alkaline-earth metal bases or with quaternary ammonium bases have good selective, pre- and post-emergence, herbicidal and growth-regulating properties.The symbols in this formula have the following meanings:A is a C.sub.3 -C.sub.6 -alkynyl group,X is oxygen, sulfur, or a sulfinyl or sulfonyl bridge,Z is oxygen or sulfur,m is the number one or two,R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.5 -alkyl, C.sub.2 -C.sub.5 -alkenyl, or a --Y--R.sub.6 group,R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.5 -alkyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.1 -C.sub.4 -haloalkyl, or a group --Y--R.sub.6, --COOR.sub.7, --NO.sub.2 or --CO--NR.sub.8 --R.sub.9,R.sub.3 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, halogen or alkoxyalkyl having at most 4 carbon atoms,R.sub.4 is hydrogen, methyl or ethyl,R.sub.5 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.3 -alkoxy, methoxymethyl, cyanomethyl or cyanoethyl,R.sub.6 and R.sub.7 are each C.sub.1 -C.sub.5 -alkyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.2 -C.sub.6 -alkynyl,R.sub.8 and R.sub.9 independently of one another are each hydrogen, C.sub.1 -C.sub.5 -alkyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.2 -C.sub.6 -alkynyl, andY is oxygen, sulfur, or a sulfinyl or sulfonyl bridge.
摘要:
Compounds of formula I ##STR1## in which R is H, or an aliphatic or aromatic radical, R.sup.1 is alkyl, R.sup.2 is alkyl, alkoxy, aryl, aryloxy, aralkyl, alkaryl, aralkyloxy, alkaryloxy, alkaralkyl or alkaralkyloxy, and one of R.sup.1 and R.sup.2 is H and the other has the meaning given above. These compounds are intermediates for the preparation of herbicidal sulfonylureas.
摘要:
R.sup.1 and R.sup.2, independently of each other, are hydrogen or C.sub.1 -C.sub.2 alkyl,R.sup.3 is hydrogen, halogen, nitro, 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 haloalkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl or C.sub.2 -C.sub.5 alkoxyalkoxy or --SO.sub.2 NR.sup.4 R.sup.5,R.sup.4 is hydrogen, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.4 alkyl,R.sup.5 is hydrogen, methyl or ethyl,R.sup.6 and R.sup.7 are each hydrogen, methyl or ethyl,W is oxygen, sulfur, a sulfinyl and sulfonyl bridgeA is a radical selected from ##STR2## in which the substituents E.sup.1, E.sup.2, X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8, Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4, Y.sup.61, Y.sup.8, Y.sup.81, Z.sup.3 and Z.sup.5 are customary organic radicals.
摘要:
N-Phenylsulfonyl-N'-pyrimidinyl- and -triazinylureas of the formula I ##STR1## wherein A is 3,3,3-trifluoropropyl or 3,3-difluorobutyl,R.sup.1 is hydrogen, halogen, nitro, cyano, 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, C.sub.1 -C.sub.4 -alkylsulfinyl, C.sub.1 -C.sub.4 -alkylsulfonyl, --CO-R.sup.6, --NR.sup.7 R.sup.8, --CO--NR.sup.9 R.sup.10 or --SO.sub.2 --NR.sup.11 R.sup.12,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 -alkylthio, C.sub.1 -C.sub.4 -alkylsulfinyl or C.sub.1 -C.sub.4 -alkylsulfonyl,R.sup.3 and R.sup.4 independently of one another are each hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.2 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.2 -C.sub.4 -alkoxyalkyl, C.sub.1 -C.sub.4 -alkoxy or --NR.sup.12 R.sup.13,R.sup.5 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,R.sup.6 is C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.2 -C.sub.6 -alkoxyalkoxy, hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl,R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12 and R.sup.13 independently of one another are each hydrogen or C.sub.1 -C.sub.4 -alkyl,E is nitrogen or the methine bridge, andZ is oxygen or sulfur;and also the salts of these compounds.
摘要:
R.sup.1 and R.sup.2, independently of each other, are hydrogen or C.sub.1 -C.sub.2 alkyl,R.sup.3 is hydrogen, halogen, nitro, 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 haloalkoxy, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl or C.sub.2 -C.sub.5 alkoxyalkoxy or --SO.sub.2 NR.sup.4 R.sup.5,R.sup.4 is hydrogen, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.4 alkyl,R.sup.5 is hydrogen, methyl or ethyl,R.sup.6 and R.sup.7 are each hydrogen, methyl or ethyl,W is oxygen, sulfur, a sulfinyl and sulfonyl bridgeA is a radical selected from ##STR2## in which the substituents E.sup.1, E.sup.2, X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8, Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4, Y.sup.6, Y.sup.61, Y.sup.8, Y.sup.81, Z.sup.3 and Z.sup.5 are customary organic radicals.