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    • 1. 发明授权
    • Process for producing sulfonylureas
    • 制备磺酰脲类的方法
    • US4518776A
    • 1985-05-21
    • US511830
    • 1983-07-08
    • Willy MeyerWerner ForyWerner Topfl
    • Willy MeyerWerner ForyWerner Topfl
    • C07D251/16A01N47/36C07C67/00C07C301/00C07C303/36C07C311/53C07C325/00C07C333/12C07D239/42C07D239/47C07D333/38C07D521/00C07D251/46C07D239/69C07D251/18C07D401/12
    • C07D521/00C07D333/38
    • 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 is also described novel sulfonylcarbamates of the above formula as intermediates.
    • 描述了一种制备式IMA的磺酰脲的方法,其中G是未取代或取代的呋喃基,噻吩基,吡咯基,吡啶基或苯基,X是烷基,卤代烷基,烷氧基,烷硫基,卤素,卤代烷氧基,烷基氨基或二烷基氨基, Y是烷基,烷氧基或卤代烷氧基,Z是氮原子或甲炔基-CH =。 该新方法包括使式G-SO 2 -NH 2的磺酰胺在碱的存在下与式Cl-CO-QT的氯甲酸酯或式G-SO 2 Cl的磺酰氯反应, 碱的存在与式H2N-CO-QT的氨基甲酸酯反应; 并且通过与下式的磺酰脲反应将式G-SO 2 -NH-CO-Q-T的所形成的氨基甲酸酯转化为式(I)所示的磺酰脲。 还描述了上述式的新型磺酰基氨基甲酸酯作为中间体。
    • 2. 发明授权
    • O-substituted-phenylsulfonamides
    • O-取代苯基磺酰胺
    • US4739068A
    • 1988-04-19
    • US887762
    • 1986-07-21
    • Karl GassWerner ForyWilly MeyerWerner Topfl
    • Karl GassWerner ForyWilly MeyerWerner Topfl
    • C07D251/16A01N47/36C07D211/22C07D213/30C07D213/64C07D213/643C07D239/42C07D251/46C07D251/52C07D301/14C07D303/22C07D307/12C07D309/06C07D317/22C07D333/16C07D401/12C07D405/12C07D409/12C07D521/00C07D213/63C07D319/06
    • C07D213/30C07D213/643C07D301/14C07D303/22C07D307/12C07D309/06C07D317/22C07D333/16C07D521/00
    • N-Phenylsulfonyl-N'-pyrimidinylureas and --N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence.In the formulaR.sub.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl,R.sub.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms,R.sub.3 is halogen, hydrogen, --NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms,R.sub.4 is hydrogen or methyl,R.sub.5 is hydrogen, C.sub.1 -C.sub.2 alkyl or methoxy,A is C.sub.1 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkenylene, each unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl,m is 0 or 1,E is nitrogen or the methine group,X is oxygen, sulfur, --SO-- or --SO.sub.2 --, andQ is hydroxyl, cyano or radicals selected from the group consisting of 5- or 6-membered heterocyclic rings and fused homologues, amines, acetals, esters, ketones, phenyls, sulfonic acid and carboxylic acids, which radicals may be further substituted and have functional structures.
    • 具有通式“IMAGE”的N-苯基磺酰基-N'-嘧啶基脲和-N'-三嗪基脲和这些化合物与胺,碱金属碱和碱土金属碱或季铵碱的盐具有良好的选择性除草和植物 应用芽前和芽后的生长调节性质。 式中R 1为氢,卤素,硝基,C 1 -C 4卤代烷基,C 1 -C 4烷基,C 1 -C 4烷氧基,C 2 -C 5烯基或C 1 -C 4烷氧基羰基,R 2为C 1 -C 3烷基或C 1 -C 3烷氧基,各自未被取代或被1至3个卤素 原子,R 3是卤素,氢,-NR 4 R 5,未被取代或被1至3个卤素原子或C 1 -C 4烷氧基取代的C 1 -C 3烷基,或是未被取代或被甲氧基,乙氧基或1至3个卤素原子取代的C 1 -C 3烷氧基, R4是氢或甲基,R5是氢,C1-C2烷基或甲氧基,A是C1-C4亚烷基或C2-C4亚烯基,各自是未取代的或被C1-C4烷基取代,m是0或1,E是氮或次甲基, X是氧,硫,-SO-或-SO 2 - ,Q是羟基,氰基或选自5-或6-元杂环和稠合同系物,胺,缩醛,酯,酮,苯基, 磺酸和羧酸,该基团可进一步被取代并具有官能结构。
    • 3. 发明授权
    • N-phenylsulfonyl-N'-pyrimidinylureas
    • N-苯基磺酰基-N'-嘧啶基脲
    • US4726836A
    • 1988-02-23
    • US887759
    • 1986-07-21
    • Karl GassWerner ForyWilly MeyerWerner Topfl
    • Karl GassWerner ForyWilly MeyerWerner Topfl
    • C07D251/16A01N47/36C07D211/22C07D213/30C07D213/64C07D213/643C07D239/42C07D251/46C07D251/52C07D301/14C07D303/22C07D307/12C07D309/06C07D317/22C07D333/16C07D401/12C07D405/12C07D409/12C07D521/00A01N43/54C07D239/69
    • C07D213/30C07D213/643C07D301/14C07D303/22C07D307/12C07D309/06C07D317/22C07D333/16C07D521/00
    • N-Phenylsulfonyl-N'-pyrimidinylureas and -N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence.In the formulaR.sub.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl,R.sub.2 is C.sub.1 -C.sub.2 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms,R.sub.3 is halogen, hydrogen, --NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms,R.sub.4 is hydrogen or methyl,R.sub.5 is hydrogen, C.sub.1 -C.sub.2 alkyl or methoxy,A is C.sub.1 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkenylene, each unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl,m is 0 or 1,E is nitrogen or the methine group,X is oxygen, sulfur, --SO-- or --SO.sub.2 --, andQ is hydroxyl, cyano or radicals selected from the group consisting of 5- or 6-membered heterocyclic rings and fused homologues, amines, acetals, esters, ketones, phenyls, sulfonic acid and carboxylic acids, which radicals may be further substituted and have functional structures.
    • 具有通式“IMAGE”的N-苯基磺酰基-N'-嘧啶基脲和-N'-三嗪基脲和这些化合物与胺,碱金属碱和碱土金属碱或季铵碱的盐具有良好的选择性除草和植物 应用芽前和芽后的生长调节性质。 式中R 1为氢,卤素,硝基,C 1 -C 4卤代烷基,C 1 -C 4烷基,C 1 -C 4烷氧基,C 2 -C 5链烯基或C 1 -C 4烷氧基羰基,R 2为C 1 -C 2烷基或C 1 -C 3烷氧基,各自未被取代或被1至3个卤素 原子,R 3是卤素,氢,-NR 4 R 5,未被取代或被1至3个卤素原子或C 1 -C 4烷氧基取代的C 1 -C 3烷基,或是未被取代或被甲氧基,乙氧基或1至3个卤素原子取代的C 1 -C 3烷氧基, R4是氢或甲基,R5是氢,C1-C2烷基或甲氧基,A是C1-C4亚烷基或C2-C4亚烯基,各自未被取代或被C1-C4烷基取代,m是0或1,E是氮或次甲基,X 是氧,硫,-SO-或-SO 2 - ,Q是羟基,氰基或选自5-或6-元杂环和稠合同系物,胺,缩醛,酯,酮,苯基,磺酸的基团 酸和羧酸,该基团可以进一步被取代并具有官能结构。
    • 6. 发明授权
    • N-phenylsulfonyl-N'-pyrimidinyl- and -N'-triazinylureas
    • N-苯基磺酰基-N'-嘧啶基和-N'-三嗪基脲
    • US4835311A
    • 1989-05-30
    • US141820
    • 1988-01-11
    • Karl GassWerner ForyWilly MeyerWerner Topfl
    • Karl GassWerner ForyWilly MeyerWerner Topfl
    • C07D251/16A01N47/36C07D211/22C07D213/30C07D213/64C07D213/643C07D239/42C07D251/46C07D251/52C07D301/14C07D303/22C07D307/12C07D309/06C07D317/22C07D333/16C07D401/12C07D405/12C07D409/12C07D521/00
    • C07D213/30C07D213/643C07D301/14C07D303/22C07D307/12C07D309/06C07D317/22C07D333/16C07D521/00
    • N-Phenylsulfonyl-N'-pyrimidinylureas and -N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence.In the formulaR.sub.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl,R.sub.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms,R.sub.3 is halogen, hydrogen, --NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms of C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms,R.sub.4 is hydrogen or methyl,R.sub.5 is hydrogen, C.sub.1 -C.sub.2 alkyl or methoxy,A is C.sub.1 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkenylene, each unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl,m is 0 or 1,E is nitrogen or the methine group,X is oxygen, sulfur, --SO-- or --SO.sub.2 --, andQ is hydroxyl, cyano or radicals selected from the group consisting of 5- or 6-membered heterocyclic rings and fused homologues, amines, acetals, esters, ketones, phenyls, sulfonic acid and carboxylic acids, which radicals may be further substituted and have functional structures.
    • 具有通式“IMAGE”的N-苯基磺酰基-N'-嘧啶基脲和-N'-三嗪基脲以及这些化合物与胺,碱金属碱和碱土金属碱或季铵碱的盐具有良好的选择性除草和植物 应用芽前和芽后的生长调节性质。 式中R 1为氢,卤素,硝基,C 1 -C 4卤代烷基,C 1 -C 4烷基,C 1 -C 4烷氧基,C 2 -C 5烯基或C 1 -C 4烷氧基羰基,R 2为C 1 -C 3烷基或C 1 -C 3烷氧基,各自未被取代或被1至3个卤素 原子,R3是卤素,氢,-NR4R5,C1-C3烷基,未取代或被C1-C4烷氧基的1至3个卤素原子取代,或是未被取代或被甲氧基,乙氧基或1至3个卤素原子取代的C1-C3烷氧基, R4是氢或甲基,R5是氢,C1-C2烷基或甲氧基,A是C1-C4亚烷基或C2-C4亚烯基,各自未被取代或被C1-C4烷基取代,m是0或1,E是氮或次甲基,X 是氧,硫,-SO-或-SO 2 - ,Q是羟基,氰基或选自5-或6-元杂环和稠合同系物,胺,缩醛,酯,酮,苯基,磺酸的基团 酸和羧酸,该基团可以进一步被取代并具有官能结构。
    • 7. 发明授权
    • N-phenylsulfonyl-N'-triazinylureas
    • N-苯基磺酰基-N'-三嗪基脲
    • US4648899A
    • 1987-03-10
    • US855060
    • 1986-04-23
    • Karl GassWerner ForyWilly MeyerWerner Topfl
    • Karl GassWerner ForyWilly MeyerWerner Topfl
    • C07D251/16A01N47/36C07D211/22C07D213/30C07D213/64C07D213/643C07D239/42C07D251/46C07D251/52C07D301/14C07D303/22C07D307/12C07D309/06C07D317/22C07D333/16C07D401/12C07D405/12C07D409/12C07D521/00A01N43/70C07D251/42
    • C07D213/30C07D213/643C07D301/14C07D303/22C07D307/12C07D309/06C07D317/22C07D333/16C07D521/00
    • N-Phenylsulfonyl-N'-pyrimidinylureas and -N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence.In the formulaR.sub.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl,R.sub.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms,R.sub.3 is halogen, hydrogen, --NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms,R.sub.4 is hydrogen or methyl,R.sub.5 is hydrogen, C.sub.1 -C.sub.2 alkyl or methoxy,A is C.sub.1 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkenylene, each unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl,m is 0 or 1,E is nitrogen or the methine group,X is oxygen, sulfur, --SO--, or --SO.sub.2 --, andQ is hydroxyl, cyano or radicals selected from the group consisting of 5- or 6-membered heterocyclic rings and fused homologues, amines, acetals, esters, ketones, phenyls, sulfonic acid and carboxylic acids, which radicals may be further substituted and have functional structures.
    • 具有通式“IMAGE”的N-苯基磺酰基-N'-嘧啶基脲和-N'-三嗪基脲和这些化合物与胺,碱金属碱和碱土金属碱或季铵碱的盐具有良好的选择性除草和植物 应用芽前和芽后的生长调节性质。 式中R 1为氢,卤素,硝基,C 1 -C 4卤代烷基,C 1 -C 4烷基,C 1 -C 4烷氧基,C 2 -C 5烯基或C 1 -C 4烷氧基羰基,R 2为C 1 -C 3烷基或C 1 -C 3烷氧基,各自未被取代或被1至3个卤素 原子,R 3是卤素,氢,-NR 4 R 5,未被取代或被1至3个卤素原子或C 1 -C 4烷氧基取代的C 1 -C 3烷基,或是未被取代或被甲氧基,乙氧基或1至3个卤素原子取代的C 1 -C 3烷氧基, R4是氢或甲基,R5是氢,C1-C2烷基或甲氧基,A是C1-C4亚烷基或C2-C4亚烯基,各自未被取代或被C1-C4烷基取代,m是0或1,E是氮或次甲基,X 是氧,硫,-SO-或-SO 2 - ,Q是羟基,氰基或选自5-或6-元杂环和稠合同系物,胺,缩醛,酯,酮,苯基, 磺酸和羧酸,该基团可进一步被取代并具有官能结构。
    • 8. 发明授权
    • N-phenylsulfonyl-N'-triazinylureas
    • N-苯基磺酰基-N'-三嗪基脲
    • US4618363A
    • 1986-10-21
    • US458799
    • 1983-01-18
    • Karl GassWerner ForyWilly MeyerWerner Topfl
    • Karl GassWerner ForyWilly MeyerWerner Topfl
    • C07D251/16A01N47/36C07D211/22C07D213/30C07D213/64C07D213/643C07D239/42C07D251/46C07D251/52C07D301/14C07D303/22C07D307/12C07D309/06C07D317/22C07D333/16C07D401/12C07D405/12C07D409/12C07D521/00A01N43/66A01N43/70
    • C07D213/30C07D213/643C07D301/14C07D303/22C07D307/12C07D309/06C07D317/22C07D333/16C07D521/00
    • N-Phenylsulfonyl-N'-pyrimidinylureas and -N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence.In the formulaR.sub.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl,R.sub.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms,R.sub.3 is halogen, hydrogen, --NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms,R.sub.4 is hydrogen or methyl,R.sub.5 is hydrogen, C.sub.1 -C.sub.2 alkyl or methoxy,A is C.sub.1 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkenylene, each unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl,m is 0 or 1,E is nitrogen or the methine group,X is oxygen, sulfur, --SO-- or --SO.sub.2 --, andQ is hydroxyl, cyano or radicals selected from the group consisting of 5- or 6-membered heterocyclic rings and fused homologues, amines, acetals, esters, ketones, phenyls, sulfonic acid and carboxylic acids, which radicals may be further substituted and have functional structures.
    • 具有通式“IMAGE”的N-苯基磺酰基-N'-嘧啶基脲和-N'-三嗪基脲和这些化合物与胺,碱金属碱和碱土金属碱或季铵碱的盐具有良好的选择性除草和植物 应用芽前和芽后的生长调节性质。 式中R 1为氢,卤素,硝基,C 1 -C 4卤代烷基,C 1 -C 4烷基,C 1 -C 4烷氧基,C 2 -C 5烯基或C 1 -C 4烷氧基羰基,R 2为C 1 -C 3烷基或C 1 -C 3烷氧基,各自未被取代或被1至3个卤素 原子,R 3是卤素,氢,-NR 4 R 5,未被取代或被1至3个卤素原子或C 1 -C 4烷氧基取代的C 1 -C 3烷基,或是未被取代或被甲氧基,乙氧基或1至3个卤素原子取代的C 1 -C 3烷氧基, R4是氢或甲基,R5是氢,C1-C2烷基或甲氧基,A是C1-C4亚烷基或C2-C4亚烯基,各自未被取代或被C1-C4烷基取代,m是0或1,E是氮或次甲基,X 是氧,硫,-SO-或-SO 2 - ,Q是羟基,氰基或选自5-或6-元杂环和稠合同系物,胺,缩醛,酯,酮,苯基,磺酸的基团 酸和羧酸,该基团可以进一步被取代并具有官能结构。