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    • 12. 发明授权
    • Acetylenic secondary alcohols
    • 乙酸仲醇
    • US4263463A
    • 1981-04-21
    • US735733
    • 1976-10-26
    • Shigeyoshi KitamuraNorbushige ItayaYoshitoshi OkunoNobuo OhnoTakashi MatsuoMasachika HiranoToshio MizutaniHisami Takeda
    • Shigeyoshi KitamuraNorbushige ItayaYoshitoshi OkunoNobuo OhnoTakashi MatsuoMasachika HiranoToshio MizutaniHisami Takeda
    • C07C33/048C07D307/28C07D307/45C07D309/06C07D309/22C07D317/54C07D333/16
    • C07D307/42C07C403/12C07D307/28C07D309/06C07D309/22C07D317/54C07D333/16C07C2101/02C07C2101/08C07C2101/16
    • 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.
    • 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。
    • 15. 发明授权
    • Benzyl pyrrolyl methyl carboxylate insecticides and acaricides
    • 苄基吡咯甲酸甲酯杀虫剂和杀螨剂
    • US4336194A
    • 1982-06-22
    • US57282
    • 1979-07-13
    • Tadashi OhsumiNobushige ItayaMasachika Hirano
    • Tadashi OhsumiNobushige ItayaMasachika Hirano
    • A01N43/36A01N53/04C07D207/00C07D207/32C07D207/323C07D207/325C07D207/452
    • C07D207/323C07D207/325
    • Carboxylic acid esters of the formula (I), ##STR1## wherein X is a hydrogen atom, or a C.sub.1 -C.sub.3 alkyl or a C.sub.1 -C.sub.3 alkoxyl group or a halogen atom linked to the meta or para position and R.sub.1 is a group of the formula (II) or (III), ##STR2## wherein R.sub.2 is a hydrogen atom or a methyl group, and when R.sub.2 is a methyl group R.sub.3 is also a methyl group, and when R.sub.2 is a hydrogen atom R.sub.3 is a group of the formula, ##STR3## (wherein R.sub.5 is a halogen atom or a C.sub.1 -C.sub.3 alkyl, vinyl or a C.sub.1 -C.sub.3 alkoxymethyl group, R.sub.6 is a hydrogen or halogen atom or a methyl group, or, taken together, R.sub.5 and R.sub.6 may form a tetramethylene group by connecting together at ends thereof), R.sub.4 is a halogen atom or a C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxyl or 3,4-methylenedioxy group, n is 1 or 2 and Y is a isopropyl or cyclopropyl group. These carboxylic acid esters are produced by reacting the reactive derivatives of a carboxylic acid represented by the formula, ##STR4## wherein R.sub.1 is a group of the formula (II) or (III), ##STR5## wherein R.sub.2, R.sub.3, R.sub.4, n and Y are as defined above, and Z is a halogen atom, with an alcohol of the formula (IV), ##STR6## wherein X is as defined above, in the presence of an acid-binding agent. These carboxylic acid esters are useful as insecticides and acaricides.
    • 式(I)的羧酸酯,其中X为氢原子,或C1-C3烷基或C1-C3烷氧基或与间位或对位连接的卤素原子,R1为 式(II)或(III)的基团,其中R2是氢原子或甲基,当R2是甲基时,R3也是甲基,当R2是氢原子时R3是 式中的一组基团(其中R 5为卤素原子或C 1 -C 3烷基,乙烯基或C 1 -C 3烷氧基甲基,R 6为氢或卤素原子或甲基,或一起为R 5 R 6是卤原子或C 1 -C 3烷基,C 1 -C 3烷氧基或3,4-亚甲二氧基,n是1或2,Y是异丙基或 环丙基。 这些羧酸酯通过使下式表示的羧酸的反应性衍生物,其中R 1是式(II)或(III)的基团,其中R 2,R 3,R 4,n 和Y如上定义,并且Z是卤素原子,与式(IV)的醇,其中X如上定义,在酸结合剂存在下,其中X如上定义。 这些羧酸酯可用作杀虫剂和杀螨剂。
    • 16. 发明授权
    • Insecticidal and acaricidal hydantoin N-methylol esters
    • 杀虫剂和杀螨剂乙内酰脲N-羟甲基酯
    • US4176189A
    • 1979-11-27
    • US909107
    • 1978-05-24
    • Nobushige ItayaMasachika Hirano
    • Nobushige ItayaMasachika Hirano
    • A01N43/50A01N53/00A01N53/04A01N53/10C07D233/72A61K31/415C07D405/12
    • C07D233/72A01N43/50A01N53/00
    • Hydantoin N-methylol esters of the formula, ##STR1## wherein one of X and Y is a carbonyl group and the other is a methylene, ethylidene or propylidene group, R.sub.1 is a lower alkyl, lower alkenyl or lower alkynyl having up to 3 carbon atoms, R.sub.2 is a group represented by the formula, ##STR2## in which R.sub.3 is a hydrogen atom or a methyl group; when R.sub.3 is a hydrogen atom, R.sub.4 is a methoxyiminomethyl or 2,2-disubstituted vinyl group in which the substituents can be selected from the group consisting of methyl, vinyl, fluorine, chlorine and bromine, or both of the substituents may form tetramethylene chain; when R.sub.3 is a methyl group, R.sub.4 is a methyl group; R.sub.5 is a methyl, methoxy, fluorine, chlorine, bromine or 3,4-methylenedioxy group; and n is 1 or 2, a process for producing the same, insecticides and acaricides containing the same as an active ingredient, and novel intermediate compounds.
    • 乙酰头孢菌素N-羟甲基酯,其中X和Y中的一个是羰基,另一个是亚甲基,亚乙基或亚丙基,R 1是具有至多3个碳的低级烷基,低级链烯基或低级炔基 原子,R 2是由下式表示的基团,其中R 3是氢原子或甲基; 当R3为氢原子时,R4为甲氧基亚氨基甲基或2,2-二取代的乙烯基,其中取代基可以选自甲基,乙烯基,氟,氯和溴,或两者均可形成四亚甲基链 ; 当R 3为甲基时,R 4为甲基; R5是甲基,甲氧基,氟,氯,溴或3,4-亚甲二氧基; n为1或2,其制造方法为含有与活性成分相同的杀虫剂和杀螨剂,以及新型中间体化合物。
    • 17. 发明授权
    • Benzyl pyrrolyl methyl carboxylate insecticides and acaricides
    • 苄基吡咯甲酸甲酯杀虫剂和杀螨剂
    • US4212879A
    • 1980-07-15
    • US948049
    • 1978-10-03
    • Tadashi OhsumiNobushige ItayaMasachika Hirano
    • Tadashi OhsumiNobushige ItayaMasachika Hirano
    • A01N43/36A01N53/04C07D207/00C07D207/32C07D207/323C07D207/325C07D207/452A01N9/22
    • C07D207/323C07D207/325
    • Carboxylic acid esters of the formula (I), ##STR1## wherein X is a hydrogen atom, or a C.sub.1 -C.sub.3 alkyl or a C.sub.1 -C.sub.3 alkoxyl group or a halogen atom linked to the meta or para position and R.sub.1 is a group of the formula (II) or (III), ##STR2## wherein R.sub.2 is a hydrogen atom or a methyl group, and when R.sub.2 is a methyl group R.sub.3 is also a methyl group, and when R.sub.2 is a hydrogen atom R.sub.3 is a group of the formula, ##STR3## (wherein R.sub.5 is a halogen atom or a C.sub.1 -C.sub.3 alkyl, vinyl or a C.sub.1 -C.sub.3 alkoxymethyl group, R.sub.6 is a hydrogen or halogen atom or a methyl group, or, taken together, R.sub.5 and R.sub.6 may form a tetramethylene group by connecting together at ends thereof), R.sub.4 is a halogen atom or a C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxyl or 3,4-methylenedioxy group, n is 1 or 2 and Y is a isopropyl or cyclopropyl group. These carboxylic acid esters are useful as insecticides and acaricides.
    • 式(I)的羧酸酯,其中X为氢原子,或C1-C3烷基或C1-C3烷氧基或与间位或对位连接的卤素原子,R1为 式(II)或(III)的基团,其中R 2是氢原子或甲基,当R 2是甲基时,R 3也是甲基, 当R 2是氢原子时,R 3是下式的基团,其中R 5是卤原子或C 1 -C 3烷基,乙烯基或C 1 -C 3烷氧基甲基,R 6是氢或卤原子或 或者一起,R 5和R 6可以通过在其末端连接而形成四亚甲基),R 4是卤原子或C 1 -C 3烷基,C 1 -C 3烷氧基或3,4-亚甲二氧基,n是 1或2,Y是异丙基或环丙基。 这些羧酸酯可用作杀虫剂和杀螨剂。
    • 20. 发明授权
    • Amide phosphorothiolate derivatives and their use as pesticides
    • 酰胺二硫代磷酸衍生物及其作为农药的用途
    • US4394379A
    • 1983-07-19
    • US113133
    • 1980-01-17
    • Osamu KirinoMasachika HiranoHisami TakedaToshiro Kato
    • Osamu KirinoMasachika HiranoHisami TakedaToshiro Kato
    • A01N57/14A01N57/30C07F9/165C07F9/24C07F9/40
    • C07F9/1651A01N57/14A01N57/30C07F9/2408
    • Amide phosphorothiolate derivatives of the formula, ##STR1## wherein X is an oxygen or sulfur atom, Y is an oxygen or sulfur atom or imino group, R.sub.1 and R.sub.2, which may be the same or different, are each a C.sub.1 -C.sub.3 alkyl group, R.sub.3 is a C.sub.1 -C.sub.4 alkyl group, R.sub.4 is a hydrogen atom or methyl group, R.sub.5 is a C.sub.1 -C.sub.3 alkyl, methoxy or ethoxy group, Z is a hydrogen atom, a methyl group or chlorine atom and n is 1 or 2, a process for producing said derivatives characterized by reacting the salt of thiophosphoric ester represented by the formula, ##STR2## wherein X, Y, R.sub.1 and R.sub.2 are as defined above and M is a sodium or potassium atom or ammonium group, with a haloacetamide derivative of the formula, ##STR3## wherein R.sub.3, R.sub.4, R.sub.5, Z and n are as defined above and W is a halogen atom, and a combined insecticide, acaricide, nematocide and/or fungicide containing said derivatives as an active ingredient.
    • 下式的酰亚胺硫代衍生物,其中X是氧或硫原子,Y是氧或硫原子或亚氨基,可以相同或不同的R 1和R 2各自为C 1 -C 3烷基 R3为C1-C4烷基,R4为氢原子或甲基,R5为C1-C3烷基,甲氧基或乙氧基,Z为氢原子,甲基或氯原子,n为1或2 制备所述衍生物的方法,其特征在于使由下式表示的硫代磷酸酯的盐,其中X,Y,R 1和R 2如上所定义,M是钠或钾原子或铵基,与卤代乙酰胺 衍生物,其中R3,R4,R5,Z和n如上所定义,W是卤素原子,以及含有所述衍生物作为活性成分的杀虫剂,杀螨剂,杀线虫剂和/或杀真菌剂的组合物。