WO2010043121A1 - Composés de pyréthroïde et utilisation de ceux-ci - Google Patents

Composés de pyréthroïde et utilisation de ceux-ci Download PDF

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Publication number
WO2010043121A1
WO2010043121A1 PCT/CN2009/070767 CN2009070767W WO2010043121A1 WO 2010043121 A1 WO2010043121 A1 WO 2010043121A1 CN 2009070767 W CN2009070767 W CN 2009070767W WO 2010043121 A1 WO2010043121 A1 WO 2010043121A1
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Prior art keywords
compound
trifluoro
mosquito
weight
dimethyl
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PCT/CN2009/070767
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English (en)
Chinese (zh)
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WO2010043121A9 (fr
Inventor
戚明珠
贺书泽
姜友法
朱萍
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江苏扬农化工股份有限公司
江苏优士化学有限公司
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Application filed by 江苏扬农化工股份有限公司, 江苏优士化学有限公司 filed Critical 江苏扬农化工股份有限公司
Publication of WO2010043121A1 publication Critical patent/WO2010043121A1/fr
Publication of WO2010043121A9 publication Critical patent/WO2010043121A9/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

  • the present invention relates to pyrethroid compounds, as well as to a process for their preparation and to the use in the field of controlling health pests. Background technique
  • Pyrethroid compounds are widely used for controlling mosquitoes and have high insecticidal activity. Due to its high efficiency, low toxicity, low residue and good environmental compatibility, it has been widely used in the field of health pest control.
  • mosquitoes and flies have some resistance to some traditional pyrethroid products (such as methrin) (Gao Xiwu et al., Chinese Journal of Vector Biology and Control, 2004, 15 (2), 105)
  • methrin traditional pyrethroid products
  • the amount of pyrethroids added to mosquito-repellent incense or aerosol products has been greatly increased. This not only increases production costs, but also increases the environmental burden.
  • the invention forms a series of novel fluorine-containing pyrethroid compounds by structural modification of the traditional pyrethroid acid and the alcohol moiety.
  • the preliminary pharmacodynamic tests of these compounds showed good insecticidal activity, fast knockdown and high lethality.
  • the pyrethroid of the invention has high vapor pressure and can be stably and volatilized at normal temperature, and can be processed into traditional insecticidal products such as insecticidal incense, electric mosquito coils, electric liquid mosquito coils, and the like, and can also be mixed into materials such as polyresin. It is a new generation of products such as mosquito repellent pendants and fan-type mosquito coils that are more convenient to use at room temperature. Summary of the invention
  • the object of the present invention is to provide a novel pyrethroid compound and its use in the control of sanitary pests such as mosquitoes, flies and German cockroaches.
  • the object of the present invention is achieved by the following technical solutions:
  • R 2 is methoxymethyl (-CH 2 0CH 3 ) or H atom
  • R 2 is When Rl is methoxy methyl
  • R2 is -CF 3 when the compound (1) 2, 3, 5, 6-tetrafluoro-4-methoxy-2-methylbenzyl, 2-dimethyl-3 -(3,3,3-trifluoro-propenyl)cyclopropanecarboxylate
  • R1 is a methoxymethyl group and R2 is -C00CH(CF 3 ) 2 , it is a compound (2) 2, 3, 5, 6-tetrafluoro-4-methoxymethylbenzyl-2, 2-di Methyl-3-(2,2,2-trifluoro-1-trifluoromethylethoxycarbonyl)vinylcyclopropanecarboxylate
  • R1 is H and R2 is -CF 3 , it is compound (3) 2, 3, 5, 6-tetrafluorobenzyl-2, 2-dimethyl-3-(3,3, 3-trifluoro-propene Cyclopropane carboxylate
  • the compound of the present invention includes a pyrethroid compound given by the formula (A) or a stereochemical isomer thereof, or a mixture of these stereoisomers.
  • the present invention also provides a process for the preparation of a compound satisfying the formula (A), that is, the compound can be produced by the following steps:
  • the cholic acid chloride of the formula (Y) and the tetrafluorobenzyl alcohol of the formula (X) are esterified.
  • the esterification reaction can be carried out in an organic solvent such as toluene, xylene or cyclohexane.
  • organic solvent such as toluene, xylene or cyclohexane.
  • the molar ratio of the chrysanthemic acid chloride to the tetrafluorobenzyl alcohol is 0.8:1 - 1.5: 1, and pyridine is added as an acid binding agent.
  • the invention also provides for the use of said compounds in the protection of sanitary pests such as mosquitoes, flies or German cockroaches.
  • the above application of the compound is carried out by using the compound (A) as a crude drug in various forms of insecticides for use in addition to mosquitoes, flies or German cockroaches.
  • insecticide examples include a disc-type insecticidal incense, an electrothermal mosquito-repellent tablet, an electrothermal liquid mosquito-repellent incense or an insecticidal aerosol.
  • the content of the compound of the present invention is 0. 005-3. 0w/w% o, the compound of the present invention is added to the substrate.
  • the liquid form of the compound of the present invention is formulated as a cream or a solution in which kerosene is used as a solvent.
  • the emulsifiable concentrate may be sprayed onto a substrate (fragrance) to form a disc-type insecticidal scent containing the above-described concentration of the compound of the present invention, followed by drying.
  • the emulsifiable concentrate further contains a surfactant and other auxiliaries;
  • the surfactant include alkyl sulfate, alkyl sulfonate, alkyl aryl sulfonate, polyoxyalkylene alkyl ether, polyoxidation One or a mixture of two or more of an alkylene aryl ether, a polyoxyalkylene styryl phenyl ether, a polyol ether or a sugar alcohol derivative;
  • examples of the other auxiliary agent include a fragrance, a colorant or sterilization One or a mixture of two or more of the agents.
  • the weight ratio of the flammable substance to the binder is from 90:10 to 99. 9 : 9 : 9 : 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9
  • Examples of the flammable substance include a dry powder of a plant selected from the group consisting of wood flour, pyrethrum extract powder, citrus peel powder, palm oil powder, coconut shell powder or walnut shell powder, or carbon powder selected from charcoal powder, activated carbon powder or coal powder, or A mixture thereof;
  • examples of the binder include a polymer selected from the group consisting of tapioca starch, corn starch or wheat starch, casein, methyl cellulose, carboxymethyl cellulose or polyvinyl alcohol, and a mixture thereof.
  • the disc-type insecticidal base material is usually prepared by mixing a combustible substance with a binder, kneading with water, molding and drying.
  • the shape of the disc-type mosquito-repellent substrate is not limited and may be a disk shape or a strip shape.
  • the present invention generally uses a conventional coil-shaped substrate having a diameter of about 12 cm and a thickness of 3-5 mm in a set of two-line fragrance.
  • the discicidal insecticidal viscous obtained above can be used in a conventional manner. Gp, igniting the discicidal insecticidal fragrance of the present invention in or near the pest habitat (e.g., house, office, barn). The burning of the insecticidal incense can volatilize the ester compound of formula (A). When the active ingredient in the air reaches a certain concentration, it stimulates, drives, paralyzes, and attacks the mosquitoes, flies, German cockroaches and other health pests. It can be used to control the health pests such as mosquitoes, flies, and German cockroaches.
  • the content of the compound of the present invention is 0.1 to 20 mg per tablet.
  • the electrothermal mosquito-repellent tablet is prepared by adding and/or coating a solution containing the compound of the present invention on a porous substrate.
  • the solution containing the compound (A) further contains an additive selected from the group consisting of an antioxidant, a fumigant conditioner, a fragrance or a dye.
  • porous substrate of the electrothermal mosquito-repellent sheet examples include pulp, asbestos, synthetic porous resin, porous inorganic powder, glass fiber, sulphur powder or porous ceramic material; the porous substrate is 30-35 mm long and 20-wide 22mm, a sheet of 1. 5-2mm thick.
  • An example of a porous mat used in the present invention is a sheet containing 50% by weight of cotton fibers and 50% by weight of pulp fibers, preferably from the viewpoint of absorbing and retaining insecticidal active components, preferably made of natural fibrous materials. sheet.
  • the electrothermal mosquito-repellent sheet of the present invention When the electrothermal mosquito-repellent sheet of the present invention is used in or near a habitat of a pest (e.g., a house, an office, a barn), a certain temperature is controlled by an electric heating plate, and the drug impregnated in the sheet begins to slowly volatize.
  • a pest e.g., a house, an office, a barn
  • the active ingredient of the space reaches a certain concentration, it can stimulate, drive, paralyze, knock down and kill the mosquitoes, flies, German cockroaches and other health pests, thereby achieving hygiene for mosquitoes, flies, German cockroaches, etc. Control of pests.
  • the singularity of the compound of the present invention is 0. 1 -0. 5% by weight of the antioxidant, 0.1 to 1% by weight of the perfume, formulated to contain 0. 1 to 2% by weight of a solution of the compound of the present invention;
  • the aliphatic hydrocarbon is preferably an aliphatic hydrocarbon of a C 14 component.
  • the electrothermal liquid mosquito liquid can bring the mosquito liquid from the bottom of the mandrel to the upper part of the new plate through the capillary action of the mandrel. Under the electric heating of the ring heater, the effective component of the space can reach a certain concentration, and then the mosquito can be
  • the health pests such as flies and German cockroaches are stimulated, driven, paralyzed, knocked down and lethal, so as to control the health pests such as mosquitoes, flies and German cockroaches.
  • the insecticidal aerosol is a composition in which a compound of the present invention, kerosene, and optionally a synergist, a fragrance, a bactericide are mixed at room temperature or under heating, and is added to a tank equipped with a valve. And the content of the compound of the present invention in the final composition is 0.001 -0. 5w / w% ; the propellant accounts for 20-60 of the total weight of the composition, and is obtained by adding a propellant to the can. %; preferably liquefied petroleum gas, propane, dimethyl ether or compressed air, further preferably propane.
  • the control valve When the insecticidal aerosol of the present invention is used in the habitat of the pest, the control valve is opened, and a high-speed air flow is generated under the pressure of the propellant, and the liquid medicine containing the active ingredient in the tank is dispersed and atomized and the propellant is vaporized.
  • the tiny liquid bead containing effective insecticidal ingredients is suspended in the air, and is in contact with sanitary insects such as mosquitoes, flies, and German cockroaches to achieve rapid killing of pests.
  • a fan-type mosquito coil was prepared in accordance with the method described in Japanese Patent No. 2004222725A. ⁇ 1 ⁇
  • a certain amount of the compound of the present invention is dissolved in acetone, and then optionally added 0.1 - 2% by weight of the antioxidant, 0.1 - 1% by weight of the fragrance.
  • the foamed fiber granules having an average outer diameter of about 6 mm were sufficiently impregnated with the acetone solution to obtain a foamed fiber granule containing the compound (A) 0.11 to 0.5%.
  • a certain amount of the drug-containing foamed fiber granules is placed in a pan of a fan-type mosquito coil, and when the power is turned on, the compound (A) is slowly volatilized by the fan to blow out the air and accumulates in the space. After reaching a certain concentration, it can stimulate, drive, paralyze, knock down and kill the mosquitoes, flies, German cockroaches and other health pests, thus achieving control of mosquitoes, flies, German cockroaches and other health pests.
  • the present invention proposes the application of the compound of the present invention in killing mosquitoes, flies, German cockroaches and the like, and proposes a specific application mode.
  • the compound of the invention and various insecticides prepared by using the same as the original drug have significant control effects on housefly, Culex pipiens pallens, German cockroach and the like.
  • the efficacy test with the existing sanitary insecticide showed that the compound (1) was 1.5 times more potent than the tetrafluthrin, and the 1R-trans isomer corresponding to the compound (1).
  • Compound (5) is more effective and more than twice as high as tetrafluthrin.
  • the 1R-cis isomer compound (6) corresponding to the compound (1) is also slightly more effective than the compound (1).
  • Examples 1-6 the disc-type insecticidal incense of Reference Example 1 was carried out according to GB13917. 4-92 for the determination of anti-mosquito efficacy, the test insect was Culex pipiens pallens, and the female mosquitoes were not sucked for 2-3 days after emergence; The specific process is to take 20 test mosquitoes with a mosquito suction tube, put them into a closed drum test device, take a section of the tested mosquito coils, put them on the incense rack, ignite the timing, remove the mosquito coils after lmin, record the hits every once in a while. After the test, the number of test mosquitoes was transferred to a clean insect cage after 20 min, and the number of dead mosquitoes was checked after 24 hours.
  • a porous mat (cotton fiber: 35 mm long, 22 mm wide, and 2 thick) was impregnated with a formulation containing 1 mg of compound (1), 15 mg of BHT (2,6-di-tert-butyl-4-methylphenol) and 0.5 mg of dye. 50% by weight, pulp fiber: 50% by weight), placed at room temperature for 3 days to prepare an electric mosquito-repellent sheet.
  • Application Example 8
  • a porous mat (cotton fiber: 35 mm long, 22 mm wide, and 2 thick) was impregnated with a formulation containing 1 mg of compound (5), 15 mg of BHT (2,6-di-tert-butyl-4-methylphenol) and 0.5 mg of dye. 50% by weight, pulp fiber: 50% by weight), placed at room temperature for 3 days to prepare an electric mosquito-repellent sheet.
  • BHT 2,6-di-tert-butyl-4-methylphenol
  • a porous pad (cotton length 35 mm, width 22 mm, thickness 2) was impregnated with a formulation containing 1 mg of tetrafluthrin, 15 mg of BHT (2,6-di-tert-butyl-4-methylphenol) and 0.5 mg of dye. Fiber: 50% by weight, pulp fiber: 50% by weight), placed at room temperature for 3 days to prepare an electric mosquito-repellent sheet.
  • Application Example 9
  • An insecticidal preparation was prepared by mixing together 0.3 parts by weight of the compound (1) and 59.7 parts by weight of kerosene under heating. The obtained preparation was placed in an aerosol can, a valve was placed on the can, and 40.0 parts by weight of propane was injected through the valve under pressure to obtain an insecticidal aerosol containing the compound (1). ) 0. 3 w/w %.
  • the application examples 7 and 8 of the present invention and the reference example 2 were tested for the efficacy of mosquitoes according to GB13917. 5-92, and a closed drum device was used.
  • the specific process is as follows.
  • the electrothermal mosquito-repellent tablets were preheated for 1 h, 2 h, 4 h, 6 h, 8 h, and 20 female Culex pipiens pallens were sucked with a mosquito tube, placed in a closed drum test device, accurately smoked for 1 min, while recording, after smoking, Turn off the power, remove the electric mosquito-repellent device, and record the number of test mosquitoes knocked down at regular intervals.
  • Table 2 Table 2 Comparison of the effects of the electric mosquito-repellent tablets prepared with the compound of the present invention and the tetramethoprim electric mosquito-repellent tablets
  • the application example 9 of the present invention was compared and tested according to GB 13917. 6-92, and a closed drum device was used.
  • the specific process is as follows: The electrothermal liquid mosquito coil sample was energized for 2h, 36h, 84h, 168h, 336h, and 20 female Culex pipiens pallens were sucked by the mosquito suction tube, and placed in a closed drum test device to accurately kill lmin, and at the same time, After the smoke, the power is turned off, and the electric liquid mosquito-repellent incense device is removed, and the number of test mosquitoes knocked down is recorded at regular intervals.
  • Table 3 Table 3 Statistics on the insecticidal effects of liquid mosquitoes prepared by the compounds of the present invention The results show that: the electrothermal liquid mosquito coil prepared by the compound (1) of the invention has good control effect on mosquitoes.
  • the efficacy test of mosquitoes, flies, and German cockroaches was carried out in accordance with GB13917. 2-92, and a closed drum device was used.
  • the specific process is as follows: Put the test insects into the tank, and after the test insects resume normal activities, quantitatively spray the lg medicament from the insecticidal aerosol tank of the present invention, and after lmin, the baffle is taken out to make the test insects and the medicament contact, immediately Timing, and start recording, record the number of tested down the pests at regular intervals. After 20 minutes, transfer all the test insects to the clean insect cage. After 24 hours, check the number of dead insects. Among them, the German cockroach tested the mortality rate of 72h.
  • the application example 1 1 of the present invention is compared with GB13917. 6-92 for the comparison of the efficacy of the invention, and a closed drum device is used.
  • the specific process is as follows: The fan-type mosquito coil is energized for 2h, 36h, 84h, 168h, 336h, and 20 female Culex pipiens pallens are sucked by the mosquito tube, put into the closed drum test device, accurately smoked lmin, and at the same time, smoked After that, the power is turned off, and the electric liquid mosquito repellent device is removed, and the number of test mosquitoes knocked down is recorded at regular intervals.
  • Table 5 The results are shown in Table 5:

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des composés de pyréthroïde représentés par la formule (A), ou les isomères stéréochimiques de ceux-ci, ou un mélange de tels isomères, et un procédé de préparation de ces composés ainsi que l'utilisation de ceux-ci pour lutter contre des insectes nuisibles. Dans la formule (A), R1 représente méthoxyméthyle (-CH2OCH3) ou H; et R2 représente –CF3 ou –COOCH(CF3)2. Il a été démontré que ces composés possèdent un effet amélioré de répulsion et de lutte contre des insectes nuisibles tels que les moustiques, les mouches et la blatte germanique.
PCT/CN2009/070767 2008-10-14 2009-03-13 Composés de pyréthroïde et utilisation de ceux-ci WO2010043121A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN200810167598.8 2008-10-14
CN200810167598A CN100584817C (zh) 2008-10-14 2008-10-14 拟除虫菊酯化合物及应用

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WO2010043121A1 true WO2010043121A1 (fr) 2010-04-22
WO2010043121A9 WO2010043121A9 (fr) 2010-07-01

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CN100584817C (zh) * 2008-10-14 2010-01-27 江苏扬农化工股份有限公司 拟除虫菊酯化合物及应用
CN101367730A (zh) * 2008-10-16 2009-02-18 贵阳柏丝特化工有限公司 一种拟除虫菊酯及合成
SG175295A1 (en) 2009-05-21 2011-11-28 Jiangsu Yangnong Chemical Co Pyrethroid compound, preparation process and use thereof
CN101632377B (zh) * 2009-06-05 2013-01-30 江苏扬农化工股份有限公司 电热灭虫片
CN102835416A (zh) * 2009-06-04 2012-12-26 江苏扬农化工股份有限公司 一种电热灭虫片
CN101632381B (zh) * 2009-06-04 2013-07-03 江苏扬农化工股份有限公司 杀虫气雾剂
CN101665433B (zh) * 2009-06-05 2013-02-13 江苏扬农化工股份有限公司 一种拟除虫菊酯化合物及其制备方法和应用
CN101637180B (zh) * 2009-06-05 2012-11-28 江苏扬农化工股份有限公司 一种杀虫香
CN104082334A (zh) * 2009-06-05 2014-10-08 江苏扬农化工股份有限公司 飞虫驱避贴
CN101637179A (zh) * 2009-06-05 2010-02-03 江苏扬农化工股份有限公司 一种电热杀虫液
CN104126603B (zh) * 2009-06-05 2016-06-15 江苏扬农化工股份有限公司 一种害虫防治驱避剂以及害虫的防除方法
CN101637178B (zh) * 2009-06-05 2013-01-30 江苏扬农化工股份有限公司 杀虫喷雾剂
CN104068042A (zh) * 2009-07-01 2014-10-01 江苏扬农化工股份有限公司 一种蚊虫控制剂及其制备方法和应用
CN104788315B (zh) * 2010-01-21 2018-03-23 江苏扬农化工股份有限公司 可用于杀虫的酯化合物
CN102283239A (zh) * 2010-06-17 2011-12-21 茅燕菊 一种杀虫剂
CN102153474B (zh) * 2011-02-14 2013-11-13 江苏扬农化工股份有限公司 防治动物寄生虫的酯化合物及其制备方法和应用
TWI663151B (zh) * 2016-05-31 2019-06-21 日商大日本除蟲菊股份有限公司 酯化合物及其用途
CN108264468A (zh) * 2016-12-30 2018-07-10 江苏扬农化工股份有限公司 一种具有醚键结构的杀虫化合物
CN107251911A (zh) * 2017-07-27 2017-10-17 浙江泽源植物科技有限公司 一种以小茴香秸秆为主要原料的无烟蚊香的制备方法
CN109907067A (zh) * 2017-12-12 2019-06-21 江苏扬农化工股份有限公司 可用于杀虫的酯化合物
CN109988068A (zh) * 2017-12-29 2019-07-09 江苏扬农化工股份有限公司 一种单一立体构型的拟除虫菊酯化合物

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CN101367722A (zh) * 2008-10-16 2009-02-18 贵阳柏丝特化工有限公司 一种拟除虫菊酯中间体的制备
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CN101381306A (zh) * 2008-10-14 2009-03-11 江苏扬农化工股份有限公司 拟除虫菊酯化合物及应用
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CN101367722A (zh) * 2008-10-16 2009-02-18 贵阳柏丝特化工有限公司 一种拟除虫菊酯中间体的制备

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