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    Novel cyclopropanecarboxylates
    1.
    发明授权
    Novel cyclopropanecarboxylates 失效
    新型环丙烷羧酸酯

    公开(公告)号：US4003945A

    公开(公告)日：1977-01-18

    申请号：US461029

    申请日：1974-04-15

    申请人： Shigeyoshi Kitamura ,  Nobushige Itaya ,  Yoshitoshi Okuno ,  Nobuo Ohno ,  Takashi Matsuo ,  Masachika Hirano ,  Toshio Mizutani ,  Hisami Takeda

    发明人： Shigeyoshi Kitamura ,  Nobushige Itaya ,  Yoshitoshi Okuno ,  Nobuo Ohno ,  Takashi Matsuo ,  Masachika Hirano ,  Toshio Mizutani ,  Hisami Takeda

    IPC分类号： C07C69/743 ,  A01N53/10 ,  C07C69/74 ,  C07D307/28 ,  C07D307/45 ,  C07D309/06 ,  C07D309/22 ,  C07D317/54 ,  C07D333/16

    CPC分类号： C07D307/42 ,  C07C403/12 ,  C07D307/28 ,  C07D309/06 ,  C07D309/22 ,  C07D317/54 ,  C07D333/16 ,  C07C2101/02 ,  C07C2101/08 ,  C07C2101/14 ,  C07C2101/16 ,  Y10S514/937 ,  Y10S514/952 ,  Y10S514/953 ,  Y10S514/957

    摘要： Novel alkynylcyclopropanecarboxylic acid esters represented by the formula, ##STR1## wherein R.sub.1 represents hydrogen, halogen, lower alkyl having up to 5 carbon atoms, lower alkenyl having up to 5 carbon atoms, lower alkynyl having up to 5 carbon atoms, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl, aryl, aryl C.sub.1 -C.sub.4 alkyl, furyl, substituted furyl, thienyl, substituted thienyl, furfuryl, substituted furfuryl, thenyl, substituted thenyl, cyclo C.sub.3 -C.sub.6 alkyl, substituted cyclo C.sub.3 -C.sub.6 alkyl, cyclo C.sub.3 -C.sub.6 alkenyl or substituted cyclo C.sub.3 -C.sub.6 alkenyl; R.sub.2 and R.sub.3 individually represent hydrogen, halogen, lower alkyl having up to 5 carbon atoms, lower alkenyl having up to 5 carbon atoms, lower alkynyl having up to 5 carbon atoms, aryl, aryl C.sub.1 -C.sub.4 alkyl or may form a carbon-carbon bond; or R.sub.1 and R.sub.3 are bonded to each other at the ends to form a polymethylene chain containing or not containing an oxygen or a sulfur atom, or R.sub.1 and R.sub.2 are bonded to each other at the ends to form a polymethylene chain containing or not containing an oxygen or a sulfur atom; R.sub.4 represents hydrogen or methyl; R.sub.5 represents hydrogen, methyl, vinyl, 1-propenyl, 2-methyl-1-propenyl, 2-methoxymethyl-1-propenyl, 2-methoxycarbonyl-1-propenyl, 2,2-dichlorovinyl or cyclopentyl-idenemethyl when R.sub.4 is hydrogen, and R.sub.5 represents methyl when R.sub.4 is methyl; and R.sub.6 and R.sub.7 represent hydrogen or methyl. These novel esters are produced by reacting an alcohol or its halide or arylsulfonate of the formula, ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.6 are defined above, and A is hydroxy, halogen or arylsulfoxy, with a cyclopropane-carboxylic acid of the formula, ##STR3## wherein R.sub.4, R.sub.5 and R.sub.7 are as defined above, or its reactive derivative. These esters are useful as an insecticide harmless to mammals.

    摘要翻译： 由式表示的新型炔基环丙烷羧酸酯，其中R 1表示氢，卤素，具有至多5个碳原子的低级烷基，具有至多5个碳原子的低级链烯基，低至5个碳原子的低级炔基，C1-C4烷氧基 C 1 -C 4烷基，C 1 -C 4烷硫基C 1 -C 4烷基，芳基，芳基C 1 -C 4烷基，呋喃基，取代的呋喃基，噻吩基，取代的噻吩基，糠基，取代的糠基，噻吩基，取代的芳基，环C 3 -C 6烷基，取代的环 C 3 -C 6烷基，环C 3 -C 6烯基或取代的环C 3 -C 6烯基; R 2和R 3各自表示氢，卤素，具有至多5个碳原子的低级烷基，具有至多5个碳原子的低级链烯基，具有至多5个碳原子的低级炔基，芳基，芳基C 1 -C 4烷基或可形成碳 - 碳 键; 或者R 1和R 3在末端彼此键合以形成含有或不含有氧原子或硫原子的多亚甲基链，或者R 1和R 2在末端彼此结合形成含有或不含有 氧或硫原子; R4代表氢或甲基; 当R4为氢时，R5代表氢，甲基，乙烯基，1-丙烯基，2-甲基-1-丙烯基，2-甲氧基甲基-1-丙烯基，2-甲氧基羰基-1-丙烯基，2,2-二氯乙烯基或环戊基 - 当R 4为甲基时，R 5表示甲基; 并且R 6和R 7表示氢或甲基。 这些新型酯通过使下式的醇或其卤化物或芳基磺酸盐与其中R1，R2，R3和R6定义如上，A是羟基，卤素或芳基磺酰基的醇或其卤化物或芳基磺酸酯与 式，其中R 4，R 5和R 7如上所定义，或其反应性衍生物。 这些酯可用作对哺乳动物无害的杀虫剂。

    Novel cyclopropanecarboxylates
    2.
    发明授权
    Novel cyclopropanecarboxylates 失效

    公开(公告)号：US4118505A

    公开(公告)日：1978-10-03

    申请号：US636981

    申请日：1975-12-02

    申请人： Shigeyoshi Kitamura ,  Nobushige Itaya ,  Yoshitoshi Okuno ,  Nobuo Ohno ,  Takashi Matsuo ,  Masachika Hirano ,  Toshio Mizutani ,  Hisami Takeda

    发明人： Shigeyoshi Kitamura ,  Nobushige Itaya ,  Yoshitoshi Okuno ,  Nobuo Ohno ,  Takashi Matsuo ,  Masachika Hirano ,  Toshio Mizutani ,  Hisami Takeda

    IPC分类号： C07D307/28 ,  C07D307/45 ,  C07D309/06 ,  C07D317/54 ,  C07D333/16 ,  C07C69/74 ,  A01N9/24

    CPC分类号： C07D307/42 ,  C07D307/28 ,  C07D309/06 ,  C07D317/54 ,  C07D333/16

    摘要： Novel alkynyl esters of cyclopropanecarboxylic acid represented by the formula, ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl having 1-4 carbon atoms, lower alkenyl having 2-4 carbon atoms, lower alkynyl having 2-4 carbon atoms, C.sub.1 -C.sub.2 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.2 alkylthio-C.sub.1 -C.sub.4 alkyl, furyl, thienyl, furfuryl, thenyl, cyclo-C.sub.3 -C.sub.6 alkyl, oxygen atom-containing cyclo-C.sub.3 -C.sub.6 alkyl, cyclo-C.sub.5 -C.sub.6 alkenyl, oxygen atom-containing cyclo-C.sub.4 -C.sub.6 alkenyl, halo-C.sub.2 -C.sub.4 alkenyl, phenyloxymethyl, phenylthiomethyl, cyclo-C.sub.5 -C.sub.6 alkenylmethyl, oxygen atom-containing cyclo-C.sub.4 -C.sub.6 alkenylmethyl, cyclo-C.sub.5 -C.sub.6 alkylmethyl, oxygen atom-containing cyclo-C.sub.4 -C.sub.6 alkylmethyl or ##STR2## IN WHICH X is halogen, nitro, cyano, methylenedioxy, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkoxy, dimethylamino, m is 0, 1, 2 or 3, n is 0, 1, 2 or 3 and each X may be different when n is 2 or 3; R.sub.2 and R.sub.3 individually represent hydrogen, halogen (except R.sub.2), phenyl, benzyl, lower alkyl having 1 - 3 carbon atoms, lower alkenyl having 2 - 3 carbon atoms, lower alkynyl having 2 - 3 carbon atoms or may form a carbon-carbon bond or are bonded to each other at the ends to form C.sub.3 -C.sub.4 polymethylene chain, or R.sub.1 and R.sub.2 are bonded to each other at the ends to form C.sub.5 polymethylene chain; R.sub.4 represents hydrogen or methyl; R.sub.5 represents hydrogen, methyl, vinyl, 1-propenyl, 2-methyl-1-propenyl, 2-methoxy-methyl-1-propenyl, 2-methoxycarbonyl-1-propenyl, 1,3-butadienyl, 2-methyl-1,3-butadienyl, 2,2-dichlorovinyl or cyclopentylidenemethyl when R.sub.4 is hydrogen, and R.sub.5 represents methyl when R.sub.4 is methyl; and R.sub.6 and R.sub.7 represent hydrogen or methyl. These novel esters are produced by reacting an alcohol or its halide or arylsulfonate of the formula, ##STR3## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.6 are as defined above, and A is hydroxy, halogen or arylsulfoxy, with a cyclopropanecarboxylic acid of the formula, ##STR4## wherein R.sub.4, R.sub.5 and R.sub.7 are as defined above, or its reactive derivative. These esters are useful as an insecticide harmless to mammals.

    Acetylenic secondary alcohols
    5.
    发明授权
    Acetylenic secondary alcohols 失效
    乙酸仲醇

    公开(公告)号：US4263463A

    公开(公告)日：1981-04-21

    申请号：US735733

    申请日：1976-10-26

    申请人： Shigeyoshi Kitamura ,  Norbushige Itaya ,  Yoshitoshi Okuno ,  Nobuo Ohno ,  Takashi Matsuo ,  Masachika Hirano ,  Toshio Mizutani ,  Hisami Takeda

    发明人： Shigeyoshi Kitamura ,  Norbushige Itaya ,  Yoshitoshi Okuno ,  Nobuo Ohno ,  Takashi Matsuo ,  Masachika Hirano ,  Toshio Mizutani ,  Hisami Takeda

    IPC分类号： C07C33/048 ,  C07D307/28 ,  C07D307/45 ,  C07D309/06 ,  C07D309/22 ,  C07D317/54 ,  C07D333/16

    CPC分类号： C07D307/42 ,  C07C403/12 ,  C07D307/28 ,  C07D309/06 ,  C07D309/22 ,  C07D317/54 ,  C07D333/16 ,  C07C2101/02 ,  C07C2101/08 ,  C07C2101/16

    摘要： Novel alkynylcyclopropanecarboxylic acid esters represented by the formula, ##STR1## wherein R.sub.1 represents hydrogen, halogen, lower alkyl having up to 5 carbon atoms, lower alkenyl having up to 5 carbon atoms, lower alkynyl having up to 5 carbon atoms, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl, aryl, aryl C.sub.1 -C.sub.4 alkyl, furyl, substituted furyl, thienyl, substituted thienyl, furfuryl, substituted furfuryl, thenyl, substituted thenyl, cyclo C.sub.3 -C.sub.6 alkyl, substituted cyclo C.sub.3 -C.sub.6 alkyl, cyclo C.sub.3 -C.sub.6 alkenyl or substituted cyclo C.sub.3 -C.sub.6 alkenyl; R.sub.2 and R.sub.3 individually represent hydrogen, halogen, lower alkyl having up to 5 carbon atoms, lower alkenyl having up to 5 carbon atoms, lower alkynyl having up to 5 carbon atoms, aryl, aryl C.sub.1 -C.sub.4 alkyl or may form a carbon-carbon bond; or R.sub.1 and R.sub.3 are bonded to each other at the ends to form a polymethylene chain containing or not containing an oxygen or a sulfur atom, or R.sub. 1 and R.sub.2 are bonded to each other at the ends to form a polymethylene chain containing or not containing an oxygen or a sulfur atom; R.sub.4 represents hydrogen or methyl; R.sub.5 represents hydrogen, methyl, vinyl, 1-propenyl, 2-methyl-1-propenyl, 2-methoxymethyl-1-propenyl, 2-methoxycarbonyl-1-propenyl, 2,2-dichlorovinyl or cyclopentylidenemethyl when R.sub.4 is hydrogen, and R.sub.5 represents methyl when R.sub.4 is methyl; and R.sub.6 and R.sub.7 represent hydrogen or methyl. These novel esters are produced by reacting an alcohol or its halide or arylsulfonate of the formula, ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.6 are as defined above, and A is hydroxy, halogen or arylsulfoxy, with a cyclopropanecarboxylic acid of the formula, ##STR3## wherein R.sub.4, R.sub.5 and R.sub.7 are as defined above, or its reactive derivative. These esters are useful as an insecticide harmless to mammals.

    摘要翻译： 由式表示的新型炔基环丙烷羧酸酯，其中R 1表示氢，卤素，具有至多5个碳原子的低级烷基，具有至多5个碳原子的低级链烯基，低至5个碳原子的低级炔基，C1-C4烷氧基 C 1 -C 4烷基，C 1 -C 4烷硫基C 1 -C 4烷基，芳基，芳基C 1 -C 4烷基，呋喃基，取代的呋喃基，噻吩基，取代的噻吩基，糠基，取代的糠基，噻吩基，取代的芳基，环C 3 -C 6烷基，取代的环 C 3 -C 6烷基，环C 3 -C 6烯基或取代的环C 3 -C 6烯基; R 2和R 3各自表示氢，卤素，具有至多5个碳原子的低级烷基，具有至多5个碳原子的低级链烯基，具有至多5个碳原子的低级炔基，芳基，芳基C 1 -C 4烷基或可形成碳 - 碳 键; 或者R 1和R 3在末端彼此键合形成含有或不含有氧原子或不含硫原子的多亚甲基链，或者R 1和R 2在末端彼此键合形成含有或不含有 氧或硫原子; R4代表氢或甲基; 当R 4为氢时，R 5表示氢，甲基，乙烯基，1-丙烯基，2-甲基-1-丙烯基，2-甲氧基甲基-1-丙烯基，2-甲氧基羰基-1-丙烯基，2,2-二氯乙烯基或环戊烯基甲基，R5 当R 4为甲基时为甲基; 并且R 6和R 7表示氢或甲基。 这些新型酯通过使下式的醇或其卤化物或芳基磺酸盐与下式的环丙烷羧酸反应来制备：其中R1，R2，R3和R6如上所定义，A是羟基，卤素或芳基磺酰基， ，其中R4，R5和R7如上定义，或其反应性衍生物。 这些酯可用作对哺乳动物无害的杀虫剂。