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    • 3. 发明授权
    • Sulfonylureas
    • SULFONYLUREAS
    • US5209771A
    • 1993-05-11
    • US823515
    • 1992-01-21
    • Willy Meyer
    • Willy Meyer
    • A01N43/66A01N47/36A01N47/46A01P13/00C07C275/28C07C335/42C07D20060101C07D239/42C07D249/14C07D251/12C07D305/08C07D331/04C07D405/12C07D409/12C07D521/00
    • C07D521/00A01N47/36C07D305/08C07D331/04
    • 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.
    • 式I的N-苯基磺酰基N'-三嗪基脲和硫脲其中X是氧,硫,SO或SO 2; W是氧或硫; R1是氢或甲基; R2是氢,氟,氯,溴,碘,(X)nR3,NO2,NR4R5,-C3OND CR6, n是数字0或1; R3是被1-4个卤素原子取代的C1-C4烷基或C1-C4烷基,C1-C3烷氧基或C1-C3烷硫基; 或被1-4个卤素原子取代的C 2 -C 4烯基或C 2 -C 4烯基; R4是氢,CH3O,CH3CH2O或C1-C3烷基; R5是氢或C1-C3烷基; R6是氢,甲基或乙基; R7是氢或甲基; Z是氮; R8是C1-C4烷基,C1-C4烷氧基,C1-C4卤代烷氧基,C1-C4卤代烷基,C1-C4卤代烷硫基,C1-C4烷硫基,卤素,C2-C5烷氧基烷基,C2-C5烷氧基烷氧基,氨基,C1-C3烷基氨基或二(C1-C3烷基)氨基和 R9是C1-C4烷基,C1-C4烷氧基,C1-C4卤代烷氧基,C1-C4卤代烷硫基,C1-C4烷硫基,C2-C5烷氧基烷基,C2-C5烷氧基烷氧基,C2-C5烷硫基烷基或环丙基,这些化合物与胺,碱金属或碱土 金属碱基或季铵碱基具有良好的芽前和芽后选择性除草和生长调节性质。
    • 4. 发明授权
    • Process for the preparation of 2-(2-halogenoethylthio)-phenylsulfonamides
    • 制备2-(2-甲基乙酰氧基)苯基磺酰胺的方法
    • US5166430A
    • 1992-11-24
    • US585743
    • 1990-09-20
    • Henry SzczepanskiWilly MeyerFranz Weibel
    • Henry SzczepanskiWilly MeyerFranz Weibel
    • B01J23/40B01J23/755C07B61/00C07C319/14C07C319/18C07C323/67C07D521/00
    • C07D521/00C07C323/67
    • 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.
    • 其中Z 1和Z 2彼此独立地为氢,氟或氯的式I(I)的2-(2-卤代乙硫基) - 苯基磺酰胺是通过以下方法制备的,其中:a)将2-卤代苯基磺酰胺 其中X是氟,氯或溴的式II(II)在碱的存在下与式III的硫醇R-SH(III)一起转化,其中R是C 1 -C 6烷基 或被苯基取代的C1-C6烷基取代成2-亚磺酰基苯基磺酰胺,b)将该化合物氧化得到2-亚磺酰基苯基磺酰胺,c)将所得的2-亚磺酰基苯基磺酰胺在酸存在下转化成式 (VI)d)将式VI的二硫化物还原成2-巯基苯基磺酰胺,e)然后通过式X(R1)3N(X)的三烷基胺将该化合物转化为其中R1 是C 1 -C 4烷基,进入2-巯基苯基磺酰胺三烷基胺盐,f)然后使该化合物反应 其中Y为氯或溴,Z 1和Z 2彼此独立地为氢,氟或氯,式IXY-CH2CFZ1Z2(IX)的卤代氟代乙烷。
    • 6. 发明授权
    • Phenylsulfonylureas
    • 苯磺酰脲
    • US4857100A
    • 1989-08-15
    • US194651
    • 1988-05-16
    • Willy Meyer
    • Willy Meyer
    • C07D239/42A01N47/36C07D239/47C07D239/48C07D239/52C07D251/16C07D251/46C07D521/00
    • C07D521/00A01N47/36
    • 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.
    • 这些化合物与胺,碱金属或碱土金属碱或季铵碱的盐具有良好的芽前和芽后,选择性除草和生长调节性质。 在该式中,R 1和R 2彼此独立地是氢或C 1 -C 2烷基,R 3是氢,卤素,硝基,C 1 -C 4烷基,C 1 -C 4卤代烷基,C 1 -C 4烷氧基,C 1 -C 4卤代烷氧基,C 1 -C 4烷氧基羰基,C 1 C 1-4烷硫基,C 1 -C 4烷基亚磺酰基,C 1 -C 4烷基磺酰基或C 2 -C 5烷氧基烷氧基或-SO 2 NR 4 R 5,R 4是氢,C 1 -C 2烷氧基或C 1 -C 4烷基,R 5是氢,甲基或乙基,R 6和R 7各自是氢,甲基或乙基,W 是氧,硫,亚磺酰基和磺酰基桥A是选自取代基E1,E2,X1,X2,X3,X4,X5的基团,其选自 + TR X6,X7,X8,Y1,Y2,Y3,Y4,Y61,Y8,Y81,Z3和Z5是常规的有机基团。
    • 7. 发明授权
    • N-phenylsulfonyl-N'-pyrimidinyl-ureas
    • N-苯基磺酰基-N'-嘧啶基 - 脲
    • US4759793A
    • 1988-07-26
    • US30529
    • 1987-03-27
    • Willy MeyerKonrad Oertle
    • Willy MeyerKonrad Oertle
    • C07D249/16A01N43/70A01N47/36C07C20060101C07C67/00C07C301/00C07C309/86C07C311/15C07C311/16C07C311/17C07C311/29C07C311/39C07C311/53C07C311/65C07C325/00C07C331/16C07C331/32C07D239/42C07D239/46C07D239/47C07D239/48C07D239/52C07D239/56C07D239/69C07D251/16C07D251/18C07D251/22C07D251/46C07D251/52C07D521/00A01N43/54
    • C07C309/86A01N47/36C07C311/65C07D521/00
    • 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.
    • 式I的N-苯基磺酰基-N'-嘧啶基 - 和 - 三嗪基脲其中A是3,3,3-三氟丙基或3,3-二氟丁基,R 1是氢,卤素,硝基,氰基,C 1 C 1-4烷基,C 1 -C 4 - 卤代烷基,C 1 -C 4 - 烷氧基,C 1 -C 4 - 烷硫基,C 1 -C 4 - 烷基亚磺酰基,C 1 -C 4烷基磺酰基,-CO-R 6,-NR 7 R 8,-CO-NR 9 R 10或-SO 2 -NR 11 R 12,R 2是氢,卤素,C 1 -C 4 - 烷基,C 1 -C 4 - 烷氧基,C 1 -C 4 - 烷硫基,C 1 -C 4烷基亚磺酰基或C 1 -C 4烷基磺酰基,R 3和R 4彼此独立地各自为氢, 卤素,C 1 -C 4烷基,C 1 -C 4卤代烷基,C 2 -C 4卤代烷氧基,C 1 -C 4烷硫基,C 1 -C 4卤代烷硫基,C 2 -C 4烷氧基烷基,C 1 -C 4烷氧基或-NR 12 R 13, ,C 1 -C 4烷基或C 1 -C 4 - 烷氧基,R 6是C 1 -C 4 - 烷氧基,C 1 -C 4卤代烷氧基,C 1 -C 4 - 烷硫基,C 2 -C 6 - 烷氧基烷氧基,氢,C 1 -C 4烷基或C 1 -C 4 卤代烷基,R 7,R 8,R 9,R 10,R 11,R 12和R 13各自独立地为氢或C 1 -C 4烷基,E为氮或次甲基桥,Z为氧或硫; 以及这些化合物的盐。
    • 8. 发明授权
    • Phenylsulfonylureas
    • 苯磺酰脲
    • US4759792A
    • 1988-07-26
    • US53915
    • 1987-05-26
    • Willy Meyer
    • Willy Meyer
    • C07D239/42A01N47/36C07D239/47C07D239/48C07D239/52C07D251/16C07D251/46C07D521/00A01N43/54C07D239/69
    • C07D521/00A01N47/36
    • 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.
    • 这些化合物与胺,碱金属或碱土金属碱或季铵碱的盐具有良好的芽前和芽后,选择性除草和生长调节性质。 在该式中,R 1和R 2彼此独立地是氢或C 1 -C 2烷基,R 3是氢,卤素,硝基,C 1 -C 4烷基,C 1 -C 4卤代烷基,C 1 -C 4 - 烷氧基,C 1 -C 4卤代烷氧基,C 1 -C 4烷氧基羰基,C 1 -C 4烷硫基 C 1 -C 4烷基亚磺酰基,C 1 -C 4烷基磺酰基或C 2 -C 5烷氧基烷氧基或-SO 2 NR 4 R 5,R 4是氢,C 1 -C 2烷氧基或C 1 -C 4烷基,R 5是氢,甲基或乙基,R 6和R 7各自是氢,甲基或乙基,W是氧 ,硫,亚磺酰基和磺酰基桥A是选自取代基E1,E2,X1,X2,X3,X4,X5,X6,X7,X8, Y1,Y2,Y3,Y4,Y6,Y61,Y8,Y81,Z3和Z5是常规的有机基团。
    • 9. 发明授权
    • N-phenylsulfonyl-N'-pyrimidinylureas
    • N-苯基磺酰基-N'-嘧啶基脲
    • US4681619A
    • 1987-07-21
    • US761941
    • 1985-08-02
    • Willy MeyerWerner Fory
    • Willy MeyerWerner Fory
    • C07D239/42A01N41/06A01N43/66A01N47/36A01P13/00C07C20060101C07C67/00C07C301/00C07C311/00C07C311/29C07C313/00C07C317/14C07C317/18C07C317/22C07C317/44C07C323/12C07C323/67C07D239/46C07D239/47C07D239/52C07D239/56C07D251/14C07D251/16C07D251/22C07D251/42C07D251/44C07D251/46C07D521/00C07D239/69A01N43/54
    • C07D521/00A01N47/36
    • 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.
    • 具有通式“IMAGE”的N-苯基磺酰基-N'-嘧啶基脲及其与胺,碱金属或碱土金属碱或季铵碱的盐具有良好的芽前和芽后选择性除草和生长调节性质。 在上式中,Q是氟,氟甲基,氯甲基,三氯甲基,1,2-二氯乙基,1,2-二溴乙基,1,2-二氯丙基,1,2-二溴丙基,1,2-二溴异丁基, 1-甲基 - 乙基或1,2-二溴-1-甲基 - 乙基,X是氧,硫,亚磺酰基或磺酰基桥,Z是氧或硫,R2是氢,卤素,C1-C5烷基,C2-C5链烯基, C1-C4卤代烷基或自由基-Y-R5,-COOR6,-NO2或-CO-NR7-R8,R3和R4各自独立地为氢,C1-C4烷基,C1-C4烷氧基,C1-C4烷硫基, 最多4个碳原子的C 1 -C 4卤代烷基,卤素或烷氧基烷基,R 5和R 6各自独立地为C 1 -C 5烷基,C 2 -C 5烯基或C 2 -C 6炔基,R 7和R 8各自独立地为氢, C 1 -C 5烷基,C 2 -C 5烯基或C 2 -C 6炔基,Y是氧,硫,亚磺酰基或磺酰基桥。