Abstract:
There is disclosed a multi-step process for the preparation of benzenesulfonamides of general formula ##STR1## wherein R is 3,3-difluorobutyl or 3,3-difluorobuten-1-yl. The benzenesulfonamides obtainable by the process of the invention are intermediates for the synthesis of herbicidally active sulfonyl ureas.
Abstract:
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.
Abstract:
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.
Abstract:
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.
Abstract:
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.
Abstract:
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.
Abstract:
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.
Abstract:
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.
Abstract:
N-Phenylsulfonyl-N'-pyrimidinylureas 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 formulaQ is fluorine, fluoromethyl, chloromethyl, trichloromethyl, 1,2-dichloroethyl, 1,2-dibromoethyl, 1,2-dichloropropyl, 1,2-dibromopropyl, 1,2-dibromoisobutyl, 1,2-dichloro-1-methyl-ethyl or 1,2-dibromo-1-methyl-ethyl,X is oxygen, sulfur, a sulfinyl or sulfonyl bridge,Z is oxygen or sulfur,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 of 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.
Abstract:
N-Phenylsulfonyl-N'-pyrimidinylureas of the general formula I ##STR1## and the salts of these compounds with amines, alkali metal bases or alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and growth regulating properties when applied pre- and postemergence.The symbols in formula I have the following meanings:R.sub.1 is hydrogen, halogen, nitro, cyano, or an alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylcarbonyl, alkylcarbamoyl or alkoxycarbonyl group, each unsubstituted or substituted by halogen or alkoxy,R.sub.2 is hydrogen, halogen, alkyl, or an alkyl, alkoxy or alkylthio group, each unsubstituted or substituted by halogen or alkoxy,R.sub.3 is alkyl, haloalkyl, alkoxy or haloalkoxy,R.sub.4 is hydrogen, halogen, R.sub.3, alkylamino or dialkylamino,R.sub.5 is hydrogen, alkyl or alkoxy, andX is an alkenylamino, cycloalkylamino or cycloalkenylamino group which may be further substituted, or is a carbamoylamido or sulfonylamino group as defined in the description, or is a 5- or 6-membered saturated heterocyclic ring system which is bonded through the nitrogen atom and which may contain a further oxygen, sulfur or nitrogen atom in the ring and must contain at least one oxo group.