• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    1345629 Thiophosphoric acid esters BAYER AG 23 Dec 1971 [26 Dec 1970] 59937/71 Heading C2P The invention comprises thiolophosphoric acid esters of the general formula wherein R<SP>1</SP> is methyl or ethyl, R<SP>2</SP> is -propyl, X is halogen, C 1 -C 4 alkyl, NO 2 , CN, phenyl, C 1 -C 4 alkyl mercapto, C 1 -C 4 alkylsulphinyl, C 1 -C 4 alkoxy, C 2 -C 5 alkoxycarbonyl or C 2 -C 5 alkylcarbonyl and m is 1, 2 or 3, X being the same or different when m is 2 or 3, provided that when m is 1, X may not be phenyl or alkoxy and when m is 2 or 3 either at least one X is C 1 -C 4 alkyl, NO 2 , CN, C 1 -C 4 alkylmercapto, C 1 -C 4 alkylsulphinyl, C 2 -C 5 alkoxycarbonyl or C 2 -C 5 alkyl carbonyl or each X is halogen. They may be obtained (a) by reacting a diester halide (R<SP>1</SP>O)(R<SP>2</SP>S)P(O)Hal with a phenol (if desired in the presence of an acid binding agent) or salt thereof of the formula where M<SP>1</SP> is H or a metal or ammonium, (b) by reacting a compound with an oxidizing agent, e.g. H 2 O 2 , this method being applicable when at least one X in the product is S(O)R<SP>3</SP>, wherein R<SP>3</SP> is C 1 -C 4 alkyl, or (c) by reacting a salt in which M<SP>2</SP> is a metal or ammonium with a haidle: R<SP>2</SP>Hal. The products have pesticidal properties and may be used as active ingredients in conventional pesticidal formulations. The compound (C 2 H 5 O)(n-C 3 H 7 S)P(O)Cl is obtained by reacting (nC 3 H 7 S)P(O)Cl 2 with ethanol in the presence of benzene and triethylamine. The potassium salt of O-ethyl-O-4-methylthiophenyl thiophosphoric acid is obtained by reacting the corresponding thionophosphoryl chloride with KOH in the presence of water and dioxan. The potassium salt of O-ethyl- 0(2,4 - dichlorophenyl) thiophosphate is obtained in a similar manner from the appropriate thiophosphoryl chloride.
    公开号:SU710500A3
    申请号:SU711728082
    申请日:1971-12-22
    公开日:1980-01-15
    发明作者:Кишино Шигео；Кудаматсу Акио；Шиокава Козо
    申请人:Фарбенфабрикен Байер Аг (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to means of combating agricultural pests, namely, an insecticoacaricidal agent based on O-fsgp-sh-3-n-propyl-0-alkyl esters of thiophosphoric acid. Known is 0-ethyl-5-n-propyl-O- (2, 4,6-trichloxyphenyl) phosphorothiolate (1a) with insecticide properties Ij. Also known are O-ethyl-5-n-propyl-O-chlorfepyl-phosphorothiolate (|) and 0-ethyl-5- and propyl-O-methylphenyl phosphorothiolate (III), which are the active principle of the insecticide 2. However, the known compounds have insufficient activity. The purpose of the invention is to find a new insecticoacaricidal agent with enhanced insecticidal activity. This goal is achieved by using an agent containing a compound of the formula T H- (ijH7 $ where R is methyl, ethyl, X is chlorine, methyl; n 0,1,2 Y methoxy, methylsulfinyl, methylthio, methoxycarbonyl, egylthio, ethoxycarbonyl) as an active substance. , propoxy, cyano, nitro, phenyl, and if Y denotes nitrs, then p-1, in the amount of 3-1,000 g / 10 ap, as well as additives selected from group group. C, carrier, diluent, sm / lg, dispersant. OopiVb uses conventional means; solutions, emulsions, suspensions, powders, pastes and granules. They are prepared by conventional methods, common with Preparation of pesticide formulations. Compounds of formula I are prepared by conventional methods, for example, by reacting a compound of the formula CO (n-SzI 5) P (o) Z, where Z is halogen, with an appropriately substituted phenol or alkali metal phenol, or by reacting the corresponding 0 -RO (substituted phenyl) -thiophosphoric acid or its metal or ammonium salt with a halide propyl. The following compounds of formula 1 are prepared as shown in Table 1. Compounds of the formula are used for comparison. 1a, p and 1h. Example 1. Experience with the larvae of the tobacco shovel or cotton brim Prodenia litura. Solvent: 3 parts by weight of dimethylAormamide, emulsifier: 0.1 weight.h, simple alkyl aryl polyglycol ether 1 weight, h. the active substance is mixed with the specified amount of solvent and emulsifier. The resulting Jft emulsifiable concentrate is diluted with water to the desired concentration. The experiment is carried out as follows. The leaves of the sweet potato are placed in the preparation of the active substance after drying are put into a Petri dish 9 cm in diameter. Then § a cup I place 10 larvae of tobacco scoops. The cup is placed in a room with a constant temperature of 28 ° C. At the end of the day, count the number of frost-separated us ohms and determine the degree of slaughter. The results are summarized in table 2. - Example 2. Experience with Tetranichus telarius. The experiment is carried out as follows: A legume plant in the developmental stage of two leaves is bent into a pot 6 cm in diameter and infested with 50-100 adults and nymphs of a spider mite. Two days after infection, 40 ml of the active ingredient preparation, prepared as in Example 1, are sprayed onto the pot. The pot was kept in the greenhouse for 10 days, and then the results of the fight against the clamp bar were determined. The results of the experiment are summarized in table 3. At that, indicator 3 means that there are no live imagos and nymphs, a 2-less than 5% of live adults and nymphs, an indicator of 1-6 up to 50% of live adults and nymphs, and an indicator of more than 51% of live adults and nymphs. Thus, the compounds proposed have a high insecticoacaricidal activity. Table 1
    133-136 / 0.1 153-158 / 0.2
    145-149 / 0.15 166-169 / 0.15
    155-157 / 0,1
    164-167 / 0.1 166-170 / 0.2 158-160 / 0.1
    154-159 / 0,2
    1,5705 1,5515
    145-152 / 0.05
    148-153 / 0.1 1.5485 1.5496
    134-136 / 0.1 1.5277 1.5099 1.5362 1.593 143-147 / 0.15 1.5290 160-162 / 0.25 1.5152 153-156 / 0.25 1.5193 156 -159 / 0,2 1,5137 1,5365 1,5388 1,5733 1,56I 1,5609
    Continuation of table 1
    The results of the experiment with the larvae1.and Prodenia litura with different concentrations of the active substance.
    Table 2 The results of the experiment with the larvae of Tetranidhus telarius at different concentrations of the active substance
    Continue with table 2
    Table 3
    eleven
    effective 1000 ppm I 300 ppm {i о о ppm otherTBo, W
    14
    3 3 3
    15
    sixteen
    17
    7
    18
    3
    nineteen
    .3 3 3 3
    20
    21
    22
    23
    J
    24
    3
    25
    3
    26
    3
    27
    3
    28
    3
    29
    3
    thirty
    3
    31
    3
    32
    3
    33
    3
    34
    3
    35
    3
    36
    3
    37
    3
    38
    3
    39
    3
    40
    3 3
    41
    42 I
    3 3 3 3
    i
    sh
    7105ftO12
    Continued that “5l.
    Indicator
     3
    3 2 3 3 2 3 3 3 3
    3 3 3 3 3 3 3 3 3 3 3
     2 3 2
    3 3
    i
    2 2 3 2 3 3 3
    3
    3
    3
    3
    3
    3
    3
    one
    3
    3 2 2
    3
    3
    3
    3 2
    3
    3 3
    2 1
    3 1 1 about
    2 O O
    权利要求:
    Claims (2)
    [1]
    About 13 Claims of invention Insecto-acaricidal agent containing as active substance O-phenyl-5-and-propyl-O-alkylbenzoyl cells of thiophosphoric acid and additive, in order to enhance insecticoacaricidal activity it contains y-to-propyl-O-alkyl esters of thiophosphoric acid compound of formula 1 M-CjH, where R is methyl, ethyl; X is chlorine, methyl; 0,1,2; n Y. -, CH-SO, CHgS,, CyHgS, C HjOCO, CH, 0, CN, NOgf. phenyl, and if y-NO, then in the amount of 3-1000 g / 10 are. Sources of information taken into account during the examination 1. USSR patent 562201, cl. C 07 F 9/165, 05/17/68.
    [2]
    2. USSR author's certificate 288835, class A 01 N 9/36, 08.18.69 (prototype).
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    同族专利:
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    TR16869A|1973-09-01|
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    HU163215B|1973-07-28|
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    YU211978A|1981-06-30|
    CS166199B2|1976-01-29|
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    US3839511A|1974-10-01|
    ES425898A1|1976-07-01|
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    ZA718610B|1972-09-27|
    DK134069B|1976-09-06|
    FR2126991A1|1972-10-13|
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    PL84208B1|1976-03-31|
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    IT951610B|1973-07-10|
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    AT313636B|1974-02-25|
    IL38438A|1975-05-22|
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    引用文献:
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    US4113864A|1967-05-17|1978-09-12|Sumitomo Chemical Company, Limited|Phosphorothiolate pesticidal composition|
    US4028438A|1967-05-17|1977-06-07|Sumitomo Chemical Company, Limited|Phosphorothiolates|
    BE786528A|1971-07-23|1973-01-22|Ciba Geigy|PROCESS FOR PREPARING NEW THIOPHOSPHATES AND COMPOUNDS OBTAINED|
    US3891728A|1971-09-30|1975-06-24|Ciba Geigy Corp|O-alkyl-S-alkyl-O-substituted phenyl-thiophosphoric acid esters|
    US3911122A|1971-09-30|1975-10-07|Ciba Geigy Corp|Insecticidal and acarididal substituted phenyl thiophosphoric acid esters|
    US4035488A|1971-09-30|1977-07-12|Ciba-Geigy Corporation|Insecticidal and acaricidal substituted phenyl thiophosphoric acid esters|
    US3992533A|1971-10-12|1976-11-16|Ciba-Geigy Corporation|O-ethyl-S-N-propyl-O--thiophosphate|
    BE794503A|1972-01-26|1973-07-25|Ciba Geigy|DOUBLE ARRIAL THIOPHOSPHATES IN PARTICULAR INSECTIC, ACARICIDE AND FUNGICIDE PROPERTIES|
    US3969444A|1972-02-01|1976-07-13|Ciba-Geigy Ag|O,S-dialkyl-O-allylphenyl-thiophosphates and -dithiophosphates|
    US4003964A|1972-02-01|1977-01-18|Ciba-Geigy Ag|Phenylene-bis|
    US3969438A|1972-02-01|1976-07-13|Ciba-Geigy Ag|O,S-dialkyl-O-cyanomethylphenylthio-phosphates and -dithiophosphates|
    US3917752A|1973-03-01|1975-11-04|Ciba Geigy Corp|0-Alkyl-5-alkyl-0-thiolphosphates|
    IL42383D0|1972-06-08|1973-07-30|Ciba Geigy Ag|New thiolphosphoric acid esters,their preparation and use for combatting pests|
    US3943202A|1972-11-03|1976-03-09|Ciba-Geigy Corporation|O-methyl/ethyl-s-propyl/butyl-o-phenyl thiophosphates and dithiophosphates having an ether group or the phenyl ring|
    US3991141A|1972-11-03|1976-11-09|Ciba-Geigy Corporation|O-methyl/ethyl-S-propyl/butyl-O-phenyl thiphosphates and dithiophosphates having a thioether group on the phenyl ring|
    CH573709A5|1972-12-22|1976-03-31|Ciba Geigy Ag|
    US3973014A|1972-12-22|1976-08-03|Ciba-Geigy Corporation|Thiolphosphoric acid ester insecticide|
    US4010227A|1973-04-03|1977-03-01|Ciba-Geigy Corporation|O-alkyl-s-alkyl-o-thiolphosphates|
    US3953546A|1973-07-31|1976-04-27|Sumitomo Chemical Company, Limited|Thiophosphorates|
    US4029774A|1974-06-26|1977-06-14|Rohm And Haas Company|O,S-dialkyl O -phenylthio-phenyl phosphorothiolates/phosphorodithioates and their derivatives and pesticidal use|
    US4008319A|1974-12-12|1977-02-15|Rohm And Haas Company|O,S-dialkyl O-benzoyl-phenyl phosphorothiolates and phosphorodithioates, pesticidal compositions and methods of use|
    US4022890A|1975-07-07|1977-05-10|Rohm And Haas Company|Safened pesticidal compositions|
    US4150124A|1976-02-21|1979-04-17|Celamerck Gmbh & Co. Kg|2,5-Dichloro-4-cyano-phenyl esters of thionophosphoric, thionothiolphosphoric and thionophosphonic acids|
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    DE3039086A1|1980-10-16|1982-05-27|Basf Ag, 6700 Ludwigshafen|2-FLUORPHENYL-THIOPHOSPHORIC ACID ESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR CONTROLLING PESTIES|
    US4322414A|1980-11-28|1982-03-30|Velsicol Chemical Corporation|Indanonyl phosphates as insecticides|
    DE3260986D1|1981-03-18|1984-11-22|Ciba Geigy Ag|Anthelmintics|
    DE3134136A1|1981-08-28|1983-03-17|Basf Ag, 6700 Ludwigshafen|3-FLUORPHENYL-THIOPHOSPHORIC ACID ESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR CONTROLLING Pests|
    US4436736A|1982-03-29|1984-03-13|Union Carbide Corporation|Methods for controlling pests with substituted phenyl thiophosphates and the thiophosphates|
    DE3304203A1|1983-02-08|1984-08-09|Bayer Ag, 5090 Leverkusen|SUBSTITUTED OXIMETHER|
    US4496552A|1983-04-22|1985-01-29|Fmc Corporation|O-Halophenyl O-alkyl S-tert-butyl phosphorothioates as pesticides|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    JP11874070|1970-12-26|
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