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    • 1. 发明授权
    • Thioureas
    • US4971994A
    • 1990-11-20
    • US336398
    • 1989-04-11
    • Jozef DrabekManfred BogerJosef Ehrenfreund
    • Jozef DrabekManfred BogerJosef Ehrenfreund
    • A01N47/34C07C335/26C07C335/28C07C335/32
    • C07C335/32A01N47/34C07C335/26C07C335/28
    • Novel N-phenyl-N-carbonylthioureas of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.10 alkyl, phenyl-C.sub.1 -C.sub.7 alkyl; C.sub.1 -C.sub.10 alkyl or phenyl-C.sub.1 -C.sub.7 alkyl each of which is monohalogenated or polyhalogenated or interrupted once or more than once by oxygen and/or sulfur; C.sub.3 -C.sub.8 cycloalkyl; C hd 3-C.sub.8 cycloalkyl which is monosubstituted or polysubstituted by halogen or C.sub.1 -C.sub.5 alkyl; or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl,R.sub.2 is C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, phenyl, phenyl-C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.8 cycloalkyl; C.sub.1 14 C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl or phenyl-C.sub.1 -C.sub.7 alkyl each of which is monohalogenated or polyhalogenated or interrupted once or more than once by oxygen and/or sulfur; C.sub.3 -C.sub.8 cycloalkyl; phenyl or C.sub.3 -C.sub.8 cycloalkyl each of which is monosubstituted or polysubstituted by halogen or C.sub.1 -C.sub.5 alkyl; or is a radical --OR.sub.9 ;R.sub.3 is C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy, C.sub.3 -C.sub.7 cycloalkyl or C.sub.5 -C.sub.6 cycloalkenyl;R.sub.4 is C.sub.1 -C.sub.7 cycloalkyl or C.sub.5 -C.sub.6 -cycloalkenyl;R.sub.5 is hydrogen or R.sub.6 (Y).sub.n ;R.sub.6 is C.sub.1 -C.sub.10 alkyl, phenyl, naphthyl, indanyl, tetrahydronaphthyl; or phenyl, naphthyl, indanyl or tetrahydronaphthyl each of which is monosubstituted or polysubstituted by ahlogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.4 haloalkoxy;R.sub.9 is C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, phenyl, phenyl-C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.8 cycloalkyl; C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, phenyl-C.sub.1 -C.sub.7 alkyl each of which is monohalogenated or polyhalogenated or interrupted once or more than once by oxygen and/or sulfur; or phenyl or C.sub.3 -C.sub.8 cycloalkyl each of which is monosubstituted or polysubstituted by halogen or C.sub.1 -C.sub.5 alkyl;Y is O, S, SO, SO.sub.2, NH, N(CHO), N(CH.sub.3) or C(R.sub.7)R.sub.8, where R.sub.7 and R.sub.8 each are hydrogen or C.sub.1 -C.sub.4 alkyl; andn is 0 or 1with the proviso that R.sub.2 can stand for the radical --OR.sub.9 only when R.sub.5 is other than hydrogen and C.sub.1 -C.sub.10 alkoxy; processes and salts of corresponding isothioureas as intermediates for their preparation, their use in the control of pests, and also pesticides containing at least one compound of the formula I or an active intermediate are disclosed. The preferred field of application is the control of pests on animals and plants.
    • 2. 发明授权
    • Substituted thioureas, isothioureas and carbodiimides
    • 取代硫脲,异硫脲和碳二亚胺
    • US4888348A
    • 1989-12-19
    • US91157
    • 1987-08-28
    • Josef EhrenfreundManfred BogerOdd KristiansenJozef DrabekHaukur Kristinsson
    • Josef EhrenfreundManfred BogerOdd KristiansenJozef DrabekHaukur Kristinsson
    • A01N47/30A01N47/32A01N47/40A01N47/42C07D207/34C07D209/32C07D231/20C07D233/70C07D235/26C07D249/12C07D257/04C07D263/38C07D263/58C07D271/10C07D271/113C07D277/20C07D277/34C07D277/68C07D285/08C07D285/12C07D285/13C07D307/58C07D333/32C07D333/34
    • C07D271/113A01N47/30A01N47/32A01N47/40A01N47/42C07D233/70C07D249/12C07D277/34C07D277/68C07D285/08C07D285/13
    • The invention relates to novel substituted phenylthioureas, phenylisothioureas and phenylcarbodiimides of formula I ##STR1## wherein Z is ##STR2## or --N.dbd.C.dbd.N--; R.sub.1 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.3 alkyl substituted by 1 or 2 C.sub.3 -C.sub.6 cycloalkyl radicals, or is alkoxyalkyl containing a total of 3 to 10 carbon atoms, halogen-substituted C.sub.1 -C.sub.12 alkyl, polycyclic C.sub.7 -C.sub.10 cycloalkyl, or phenyl(C.sub.1 -C.sub.5)alkyl which may be substituted in the phenyl moiety by 1 or 2 identical or different members selected from the group consisting of halogen, methoxy, ethoxy and C.sub.1 -C.sub.5 alkyl,R.sub.2 is hydrogen or C.sub.1 -C.sub.5 alkyl,R.sub.3 is C.sub.1 -C.sub.5 alkyl or C.sub.3 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sub.5 is a 5-membered heterocyclic radical containing 1 to 4 hetero atoms selected from the group consisting of N, O and S, which radical may be substituted at the carbon or nitrogen atoms by 1 to 3 of the substituents R.sub.6, R.sub.7 and R.sub.8, or is a 5-membered heterocyclic radical which may be fused with benzene nuclei and which contains 1 or 2 hetero atoms selected from the group consisting of N, O and S and can be substituted at the carbon or nitrogen atoms by 1 to 3 of the substituents R.sub.6, R.sub.7 and R.sub.8,R.sub.6 and R.sub.7 are each independently of the other hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, halogen-substituted C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy; halogen-substituted C.sub.1 -C.sub.4 alkoxy, phenyl, or C.sub.1 -C.sub.4 alkylthio,R.sub.8 is hydrogen or C.sub.1 -C.sub.4 alkyl, andR.sub.9 is C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.3 -C.sub.4 alkynyl, alkoxyalkyl containing a total of 10 carbon atoms, or alkylthioalkyl containing a total of 10 carbon atomsand to the salts thereof with acids and bases. The invention further relates to the preparation of these compounds and to the use thereof in pest control, and to novel intermediates.
    • 本发明涉及式I的新的取代的苯基硫脲,苯基异硫脲和苯基碳二亚胺其中Z是或-N = C = N-; R 1是C 1 -C 12烷基,C 3 -C 10烯基,C 3 -C 10炔基,C 3 -C 8环烷基,被1或2个C 3 -C 6环烷基取代的C 1 -C 3烷基,或者是含有总共3至10个碳原子的烷氧基烷基,卤素取代的C 1 -C 12烷基 ,多环C 7 -C 10环烷基或可在苯基部分被1或2个选自卤素,甲氧基,乙氧基和C 1 -C 5烷基的相同或不同的成员取代的苯基(C 1 -C 5)烷基,R 2为氢或 C 1 -C 5烷基,R 3是C 1 -C 5烷基或C 3 -C 6环烷基,R 4是氢或C 1 -C 4烷基,R 5是含有1至4个选自N,O和S的杂原子的5元杂环基, 可以在碳原子或氮原子上被1至3个取代基R6,R7和R8取代,或者是可以与苯核稠合并且含有1或2个选自以下的杂原子的5元杂环基: 的N,O和S,并且可以在碳或氮原子上被1至3个取代 取代基R 6,R 7和R 8,R 6和R 7各自独立地为氢,卤素,C 1 -C 4烷基,卤素取代的C 1 -C 4烷基,C 1 -C 4烷氧基, 卤素取代的C1-C4烷氧基,苯基或C1-C4烷硫基,R8是氢或C1-C4烷基,R9是C1-C5烷基,C2-C5链烯基,C3-C4炔基,含有总共10个碳原子的烷氧基烷基,或含有 总共10个碳原子,并与其与酸和碱的盐反应。 本发明进一步涉及这些化合物的制备及其在病虫害防治中的应用,以及新颖的中间体。
    • 5. 发明授权
    • Phenylthioureas, phenylisothioureas, phenylcarbodiimides, pesticidal
compositions containing them and their use in pest control
    • 苯硫脲,苯基异硫脲,苯基碳二亚胺,含有它们的杀虫组合物及其在病虫害防治中的应用
    • US4952599A
    • 1990-08-28
    • US221849
    • 1988-07-20
    • Josef EhrenfreundManfred BogerJozef Drabek
    • Josef EhrenfreundManfred BogerJozef Drabek
    • A01N47/30A01N47/32A01N47/40A01N47/42C07D249/12C07D257/04C07D263/46C07D263/58C07D271/10C07D277/20C07D277/36C07D277/70C07D277/74C07D285/08C07D285/12C07D285/125
    • C07D263/58A01N47/30A01N47/32A01N47/40A01N47/42C07D249/12C07D277/36C07D277/74C07D285/08C07D285/125
    • Novel substituted phenylthioureas, phenylisothioureas and phenylcarbodiimides of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.10 alkyl, unsubstituted or substituted by one or more halogen atoms and/or C.sub.1 -C.sub.6 alkoxy groups; C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyl which is substituted by one or more halogen atoms and/or C.sub.1 -C.sub.4 alkyl groups; C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl, di(C.sub.3 -C.sub.8)cycloalkyl-C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 phenylalkyl or C.sub.1 -C.sub.4 phenylalkyl which is substituted in the phenyl nucleus by one or more members selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and/or C.sub.1 -C.sub.4 haloalkyl; or is C.sub.5 -C.sub.6 cycloalkenyl,R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkenyl,R.sub.3 is C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen or C.sub.1 -C.sub.3 alkyl,R.sub.5 is a 5-membered heterocycle containing 1 to 4 identical or different hetero atoms selected from the group consisting of N, O and S, or is a heterocycle which is substituted by one or more members selected from the group consisting of 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 and/or phenyl or substituted phenyl, and which contains 1 to 4 identical or diffenent hetero atoms selected from the group consisting of N, O and S,Z is --NH--CS--NH--, --N.dbd.C(SR.sub.6)--NH-- or --N.dbd.C.dbd.N--, andR.sub.6 is C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyland to salts thereof, to the preparation of these compounds and to intermediates for their synthesis. The invention further relates to the use of the novel compounds in pest control and to pesticidal compositions which contain at least one compound of formula I. The preferred utility is the control of pests of animals and plants.
    • 新型取代的苯硫基脲,苯基异硫脲和式I的苯基碳二亚胺其中R 1是未被取代或被一个或多个卤素原子和/或C 1 -C 6烷氧基取代的C 1 -C 10烷基; C 3 -C 6烯基,C 3 -C 8环烷基,被一个或多个卤素原子和/或C 1 -C 4烷基取代的C 3 -C 8环烷基; C 3 -C 8环烷基-C 1 -C 4烷基,二(C 3 -C 8)环烷基-C 1 -C 4烷基; 在苯基核中被一个或多个选自卤素,C 1 -C 4烷基,C 1 -C 4烷氧基和/或C 1 -C 4卤代烷基的成员所取代的C 1 -C 4苯基烷基或C 1 -C 4苯基烷基; 或者是C 5 -C 6环烯基,R 2是氢,C 1 -C 5烷基或C 5 -C 6环烯基,R 3是C 1 -C 5烷基或C 5 -C 6环烷基,R 4是氢或C 1 -C 3烷基,R 5是含有1至4个相同或不同的5元杂环 选自N,O和S的杂原子,或是被一个或多个选自卤素,C 1 -C 4烷基,C 1 -C 4烷氧基,C 1 -C 4卤代烷基,C 1 -C 4卤代烷氧基, C 1 -C 4烷硫基和/或苯基或取代的苯基,并且其含有1至4个选自N,O和S的相同或衍生的杂原子,Z是-NH-CS-NH-,-N = C(SR6 )-NH-或-N = C = N-,R 6为C 1 -C 5烷基,C 2 -C 5烯基,C 3 -C 4炔基,C 1 -C 4烷氧基-C 1 -C 4烷基或C 1 -C 4烷硫基-C 1 -C 4烷基及其盐 这些化合物的制备及其合成中间体。 本发明还涉及新型化合物在害虫防治中的用途以及含有至少一种式I化合物的杀虫组合物。优选的用途是控制动物和植物的害虫。
    • 8. 发明授权
    • Anilinophenylthioureas, compositions containing them, and the use
thereof in pest control
    • 苯胺基苯硫脲,含有它们的组合物及其在害虫防治中的用途
    • US5026730A
    • 1991-06-25
    • US230814
    • 1988-08-11
    • Manfred BogerJozef DrabekJosef Ehrenfreund
    • Manfred BogerJozef DrabekJosef Ehrenfreund
    • A01N47/30A01N47/32A01N47/40A01N47/42C07C67/00C07C241/00C07C267/00C07C325/00C07C335/20C07C335/32C07C335/36
    • A01N47/42A01N47/30A01N47/32A01N47/40C07C335/20C07C335/36C07C2101/08C07C2101/14
    • The invention relates to novel substituted anilinophenylthioureas, anilinophenylisothioureas and anilinophenylcarbodiimides of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.12 alkyl, unsubstituted or substituted by one or more halogen atoms and/or C.sub.1 -C.sub.6 alkoxy groups; C.sub.3 -C.sub.8 cycloalkyl, unsubstituted or substituted by one or more C.sub.1 -C.sub.3 alkyl groups; or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl,R.sub.2 and R.sub.3 are each C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen, methyl or --CHO,R.sub.5 is halogen; C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by one or more halogen atoms; C.sub.1 -C.sub.4 alkoxy, unsubstituted or substituted by one or more halogen atoms; or is a --CH.dbd.CH--.sub.2, --CH.sub.2--3 or --CH.sub.2--4 bridge in 2,3- or 3,4-position,n is 0, 1, 2, 3 or 4,Z is --NH--CS--NH--, --N.dbd.C(SR.sub.6)--NH-- or --N.dbd.C.dbd.N--; andR.sub.6 is C.sub.1 -C.sub.6 alkyl or allyl,to salts thereof with organic or inorganic acids, to the preparation of these compounds and to intermediates for their synthesis. The invention further relates to the use of the novel compound in pest control and to pesticidal compositions which contain at least one compound of formula I as active component. The preferred utility is the control of pests of animals and plants.
    • 本发明涉及式I的新型取代的苯胺基苯硫脲,苯胺基异硫脲和苯胺基碳化二亚胺其中R1是未被取代或被一个或多个卤素原子和/或C 1 -C 6烷氧基取代的C 1 -C 12烷基; 未被取代或被一个或多个C 1 -C 3烷基取代的C 3 -C 8环烷基; 或C 3 -C 8环烷基-C 1 -C 4烷基,R 2和R 3各自为C 1 -C 5烷基或C 5 -C 6环烷基,R 4为氢,甲基或-CHO,R 5为卤素; 未被取代或被一个或多个卤素原子取代的C 1 -C 4烷基; 未被取代或被一个或多个卤素原子取代的C 1 -C 4烷氧基; 或在2,3-或3,4-位是-CH = CH-2,-CH2-3或-CH2-4桥,n为0,1,2,3或4,Z为-NH-CS -NH-,-N = C(SR 6)-NH-或-N = C = N-; 并且R 6是C 1 -C 6烷基或烯丙基,与其与有机或无机酸的盐相关,用于制备这些化合物及其合成中间体。 本发明还涉及新型化合物在害虫防治中的用途以及含有至少一种式I化合物作为活性成分的农药组合物。 优选的效用是控制动物和植物的害虫。