WO2021169699A1 - Utilisation d'un composé hétérocyclique à pont d'oxygène à huit chaînons utilisé en tant que synergiste insecticide présentant une sélectivité vis-à-vis de l'abeille - Google Patents

Utilisation d'un composé hétérocyclique à pont d'oxygène à huit chaînons utilisé en tant que synergiste insecticide présentant une sélectivité vis-à-vis de l'abeille Download PDF

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WO2021169699A1
WO2021169699A1 PCT/CN2021/073608 CN2021073608W WO2021169699A1 WO 2021169699 A1 WO2021169699 A1 WO 2021169699A1 CN 2021073608 W CN2021073608 W CN 2021073608W WO 2021169699 A1 WO2021169699 A1 WO 2021169699A1
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alkyl
group
substituted
halogen
alkoxy
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Chinese (zh)
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李忠
徐晓勇
张晓�
王轶平
刘泽文
邵旭升
须志平
程家高
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华东理工大学
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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D498/18—Bridged systems

Definitions

  • the invention relates to the field of pesticides. Specifically, the present invention relates to a new use of an eight-membered oxygen-bridged heterocyclic compound containing a benzene ring structure that is selective for honeybees as a synergist of neonicotinoid insecticides and other insecticides.
  • Insecticide synergist refers to a class of chemicals that have little or no insecticidal activity against insects, but when added to a certain insecticide, it can greatly improve the insecticidal efficacy of the insecticide.
  • the U.S. Army began to use sesame oil as a synergist to make a concentrated preparation containing 5% to 20% of sesamin, which was compounded into aerosols or propellants of pyrethrin insecticides, which contained The sesamin can increase the effect of pyrethrins and increase the fly-killing activity of natural pyrethrins.
  • Synergists mainly improve the insecticidal effect of insecticides by changing the physical properties of the insecticide, changing the ability of the insecticide to penetrate the epidermis, and inhibiting the activity of insect metabolism and detoxification enzymes.
  • the purpose of the present invention is to provide a new use of an eight-membered oxygen-bridged heterocyclic compound containing a benzene ring that is selective to honeybees as an insecticide synergist, which is compounded with a neonicotinoid insecticide, While it can significantly increase its insecticidal effect, it also shows selectivity to bees (does not increase the toxicity of insecticides to bees).
  • the eight-membered oxygen-bridged heterocyclic compounds containing benzene ring also show excellent synergistic effects on pesticides such as chlorpyrifos, pymetrozine, chlorantraniliprole and abamectin.
  • the first aspect of the present invention provides the use of the compound represented by formula (I), or its optical isomer, cis-trans isomer, or agrochemically acceptable salt thereof, as a selective insecticide for honeybees Synergist,
  • Y is nitro, cyano, trifluoromethyl, trifluoroacetyl, -COOC 1-6 alkyl or trifluoromethanesulfonyl;
  • R 6 and R 7 are each independently H, C 1-6 alkyl, allyl, benzyl, C 1-4 alkoxy-C 1-4 alkyl, C 1-4 alkoxy-carbonyl, Phenoxycarbonyl, C 2-6 alkynyl-carbonyl, C 2-3 alkenyl-carbonyl, C 3-6 cycloalkyl-carbonyl, benzoyl or one or more selected from halogen atoms, C 1-4 Alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, C 1-4 alkyl-carbonyl substituent substituted with benzoyl, furan carbonyl, N, N dimethyl carbonyl, or R 6 And R 7 together form -CH 2 -CH 2 -or -CH 2 -CH 2 -CH 2 -;
  • R 1 , R 2 , R 3 , R 4 and R 5 are each independently H, halogen, hydroxyl, cyano, nitro, C 1-6 alkyl, C 1-8 alkoxy, halogenated C 1- 6 alkyl, halogenated C 1-6 alkoxy, -NR a R b , -OR c , allyl, benzyl, -COOC 1-4 alkyl, -COC 1-4 alkyl, C 1- 4 Alkyl-sulfonate group, or substituted or unsubstituted phenyl, said substitution refers to being substituted by one or more substituents selected from the group consisting of halogen, C 1-4 alkyl, C 1 -4 haloalkyl or C 1-4 chloroalkoxy;
  • R a and R b are each independently H, C 1-6 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted 5-8 membered heteroaryl, and the substitution refers to being selected from the following group Is substituted by one or more substituents: halogen, C 1-6 alkyl;
  • R c is a phenyl group, a 5-8 membered heteroaryl group, a C 3-6 cycloalkyl group, a 5-8 membered heterocycloalkyl group, and the above groups are optionally substituted by a group selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 haloalkyl.
  • R 1 , R 2 , R 3 , R 4 and R 5 are not hydrogen at the same time.
  • R 1 , R 2 , R 4 and R 5 are each independently H, halogen, cyano, hydroxyl, C 1-4 alkyl, C 1-4 alkoxy, halogenated C 1 -4 alkyl, halogenated C 1-4 alkoxy, -NR a R b , -OR c , allyl, benzyl, -COOC 1-4 alkyl, -COC 1-4 alkyl, C 1 -4 Alkyl-sulfonate group, or substituted or unsubstituted phenyl, said substitution refers to being substituted by one or more substituents selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 haloalkyl or C 1-4 chloroalkoxy.
  • R 1 , R 2 , R 4 and R 5 are each independently selected from: H, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, Tert-butyl, methoxy, cyano, nitro, trifluoromethyl
  • R 3 is H, halogen, hydroxy, C 1-4 alkyl, C 1-4 alkoxy, halogenated C 1-4 alkyl, halogenated C 1-4 alkoxy, -NR a R b , -OR c , allyl, benzyl, -COOC 1-4 alkyl, -COC 1-4 alkyl, C 1-4 alkyl-sulfonate group, or substituted or unsubstituted Phenyl, said substitution means being substituted by one or more substituents selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 haloalkyl or C 1-4 chloroalkoxy ;
  • R a and R b are each independently H, C 1-4 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted 5-6 membered heteroaryl, and the substitution refers to being selected from the following group Is substituted by one or more substituents: halogen, C 1-4 alkyl;
  • R c is a phenyl group, a 5-6 membered heteroaryl group, a C 3-6 cycloalkyl group, a 5-6 membered heterocycloalkyl group, and the above group is optionally substituted with a group selected from the group consisting of halogen.
  • the heteroaryl group is selected from: pyridine, pyrrole, thiazole, furan, and thiophene.
  • R 3 is H, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, C 1-4 alkoxy Group, nitro group, trifluoromethyl group, hydroxyl group, -NR a R b , -OR c , phenyl group, C 1-4 alkyl substituted phenyl group; the definitions of Ra , R b , and R c are as described above .
  • R 6 and R 7 are each independently a C 1-4 alkyl group. In another preferred embodiment, R 6 is ethyl and R 7 is methyl. In another preferred example, R 6 and R 7 together form -CH 2 -CH 2 -or -CH 2 -CH 2 -CH 2 -.
  • Y is nitro, cyano, or -COOC 1-4 alkyl.
  • Y is nitro.
  • the compound is any compound in Table 1.
  • the insecticide is a neonicotinoid insecticide, an organophosphorus insecticide, a carbamate insecticide, a rinidin receptor inhibitor, a biological insecticide or a pyridine.
  • the insecticide is selected from the group consisting of imidacloprid, acetamiprid, thiacloprid, clothianidin, nitenpyram, chlorothiarid, thiamethoxam, dinotefuran, epoxy Tetrapyridine, piperidine, chlorpyrifos, aphicarb, chlorantraniliprole, abamectin, pymetrozine.
  • insects are aphids, armyworms or Tetranychus cinnabarinus.
  • insect is alfalfa aphid, armyworm or Tetranychus cinnabarinus
  • the effective concentration of the compound represented by formula (I) is 0.01-100 mg/L.
  • the effective concentration of the compound represented by formula (I) is 0.01-50 mg/L, preferably 0.01-10 mg/L, more preferably 0.1-4 mg/L.
  • the second aspect of the present invention provides an agricultural composition, comprising an active ingredient (a): a compound represented by formula (I), or its optical isomer, cis-trans isomer, or agrochemically acceptable And active ingredient (b): insecticide; and the weight ratio of active ingredient (a) and active ingredient (b) is 1:100-100:1.
  • the agricultural compositions are solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active ingredients, microcapsules, coatings, Formulations used with combustion devices, ULV cold mist (Cold mist) or warm mist (Warm mist) formulations.
  • the agricultural composition is used to kill or prevent agricultural pests, sanitary pests and pests endangering animal health.
  • the third aspect of the present invention provides the agricultural composition of the second aspect or the use of the above-mentioned benzene ring-containing eight-membered oxygen bridged heterocyclic compound for killing or preventing agricultural pests, sanitary pests and pests endangering animal health.
  • Insect agent composition provided.
  • the pests are Hemiptera insects, Blattella insects, Orthoptera insects or Diptera insects.
  • the Hemiptera insects include: brown planthopper, Laodelphax striatellus, White-backed planthopper, Bemisia tabaci, cotton aphid, green peach aphid, leafhopper.
  • the Blattaria include: American cockroach and German cockroach.
  • the Orthopteran insects include Oriental Migratory Locust and Desert Migratory Locust.
  • the Thysanoptera insects include: thrips.
  • the Diptera insects include: housefly, Aedes aegypti, species fly, Culex mosquito, and Anopheles sinensis.
  • the effective concentration of the compound is 0.01-100 mg/L. In another preferred example, the effective concentration of the compound is 0.01-50 mg/L, preferably 0.01-10 mg/L, more preferably 0.1-4 mg/L.
  • the present invention provides an insecticidal and/or insect control method, the method comprising the steps of: applying the above agricultural composition of the present invention to the plant body, the surrounding soil or Environment.
  • the weight ratio of the active ingredient (a) to the active ingredient (b) is 1:100-100:1; preferably, it is 1:50-10:1; More preferably, it is 1:10 to 4:1.
  • the effective concentration of the active ingredient (a) is 0.01-100 mg/L.
  • the effective concentration of the active ingredient (a) is 0.01-50 mg/L, preferably 0.01-10 mg/L, more preferably 0.1-4 mg/L.
  • FIG 1 shows the toxic effects of IPPA08 and compound 4 on imidacloprid.
  • the inventors of the present invention modified the structure of the compound IPPA08, which was found to be synergistic to pesticides, and replaced the pyridine ring with a benzene ring to synthesize a new type of benzene-containing ring.
  • Insecticide synergistic effect test showed that the compound provided by the present invention has significant insecticide synergistic effect and is selective to bees. While improving the activity of the insecticide, it does not increase the insecticide itself to bees. toxicity.
  • the preparation method is simple, and it is expected to be developed into a new type insecticide synergist with high efficiency and selectivity to bees.
  • the bee selectivity in the present invention means that the compound with the synergistic effect of the insecticide in the present invention improves the activity of the insecticide without increasing the toxicity of the insecticide itself to the honeybee.
  • the synergistic effect of the compound provided by the present invention on the insecticide is selective between the target pest and the non-target organism bee.
  • the active ingredient of the present invention can be prepared into a pesticide composition by a conventional method.
  • active ingredient of the present invention includes the active ingredient (a): the compound represented by formula (I), or its optical isomer, cis-trans isomer, or agrochemically acceptable salt thereof, and active Component (b): insecticide (including any commercially available insecticide).
  • active ingredient (a) itself has little or no insecticidal activity at a low concentration (10mg/L), but it has a significant synergistic effect on the active ingredient (b), which can significantly improve the killing of the active ingredient (b). Insect activity.
  • the weight ratio of the active ingredient (a) to the active ingredient (b) is 1:100-100:1; preferably, it is 1:50-10:1; more preferably, It is 1:10 to 4:1.
  • agrochemically acceptable salt means that the anion of the salt is known and acceptable when it forms a pharmaceutically acceptable salt of an insecticide.
  • the salt is preferably water-soluble.
  • Suitable acid addition salts formed by the compound of formula (I) include salts formed with inorganic acids, such as hydrochloride, phosphate, sulfate, nitrate; and include salts formed with organic acids, such as acetate, Benzoate.
  • the active substance of the present invention can be used to control and eliminate a wide range of agricultural and forestry plant pests, stored grain pests, pests endangering animal health, public health pests, and the like.
  • insecticide is a general term for substances that have the effect of controlling all the above-mentioned pests.
  • pests include, but are not limited to: Coleopteran insects, such as Sitophilus zeamais, Tribolium castaneum, Potato ladybug (Henosepilachna vigintioctomaculata), Henosepilachna sparsa, thin breasted Agriotes fuscicollis, red-footed green beetle (Anomala cupripes), four-striped beetle (Popillia quadriguttata), potato leaf beetle (Monolepta hieroglyphica), pine beetle (Monochamus alternatus), rice root weevil (Emechinocnemus) Leaf beetle (Basiprionota bisignata), Anoplophora chinensis, Apripona germari, Scolytus schevy, or Agriotes fuscicollis; Lepidopteran insects, such as gypsy E (Lymantria dispar), Sky screen caterpillar (Malacosoma
  • the compound of the present invention is particularly effective for piercing, sucking, filing, or chewing mouthparts pests such as aphids, leafhoppers, planthoppers, whiteflies, armyworms and other agricultural and forestry pests.
  • the active ingredients of the present invention can be made into conventional preparations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules; aerosols, natural and synthetic materials impregnated with active substances, in Microcapsules in polymers, coating compounds for seeds, and preparations used with combustion devices, such as smoking cartridges, smoking pots and smoking trays, as well as ULV cold mist (Cold mist) and heat Warm mist formulations.
  • the active compound is mixed with an extender, which is a liquid or liquefied gas or solid diluent or carrier, and optionally surfactants, emulsifiers and/or Dispersant and/or foam former.
  • an extender which is a liquid or liquefied gas or solid diluent or carrier
  • surfactants emulsifiers and/or Dispersant and/or foam former.
  • organic solvents can also be used as additives.
  • a liquid solvent When a liquid solvent is used as a diluent or carrier, it is basically suitable, such as: aromatic hydrocarbons, such as xylene, toluene or alkyl naphthalene; chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride Or dichloromethane; aliphatic hydrocarbons, such as cyclohexane or paraffin, such as mineral oil fractions; alcohols, such as ethanol or ethylene glycol and their ethers and lipids; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl Base ketone or cyclohexanone; or uncommon polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatic hydrocarbons such as xylene, toluene or alkyl naphthalene
  • chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlor
  • the diluent or carrier of liquefied gas refers to a liquid that will become a gas at normal temperature and pressure, such as aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • the solid carrier can be ground natural minerals, such as kaolin, clay, talc, quartz, activated clay, montmorillonite, or diatomaceous earth, and ground synthetic minerals, such as highly dispersed silicic acid, alumina and silicate. .
  • the solid carrier for the particles is crushed and classified natural zircon, such as calcite, marble, pumice, sepiolite and dolomite, as well as particles synthesized from inorganic and organic coarse powder, and organic materials such as sawdust, coconut shell, Corn cobs and tobacco stalks, etc.
  • Nonionic and anionic emulsifiers can be used as emulsifiers and/or foam formers.
  • polyoxyethylene-fatty acid esters polyoxyethylene-fatty alcohol ethers, such as alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and white Protein hydrolysate.
  • Dispersants include, for example, lignin sulfite waste liquor and methyl cellulose.
  • Binders such as carboxymethyl cellulose and natural and synthetic polymers in the form of powders, granules or emulsions such as gum arabic, polyvinyl alcohol and polyvinyl acetate can be used in the formulation.
  • Colorants such as inorganic dyes such as iron oxide, diamond oxide and Prussian blue; organic dyes such as organic dyes such as azo dyes or metal phthalocyanine dyes; and trace nutrients such as iron, manganese, boron, and copper , Cobalt, aluminum and zinc salts.
  • the present invention provides a new use of a compound with a structure represented by formula (I) (see patent CN200810207355.2 for the preparation method) as a bee selective insecticide synergist.
  • the compound can greatly enhance the efficacy of existing insecticides (especially neonicotinoid insecticides) and has good selectivity for bees, reduces the amount of insecticides used, and reduces a variety of agricultural pests .
  • the cost of prevention and control of sanitary pests plays an important role in the prevention and control of pest resistance.
  • Example 13 N,N-dimethyl-4-((10-nitro-2,3,6,7,8,9-hexahydro-5,9-epoxyimidazo[1,2-a ] Azacyclooctanimine-1(5H)-yl)methyl)aniline
  • Example 24 4-Methyl-N-(4-((10-nitro-2,3,6,7,8,9-hexahydro-5,9-epoxyimidazo[1,2-a ]Azacyclooctene-1(5H)-yl)methyl)phenyl)aniline
  • Example 39 Test of the synergistic activity of the compound of the present invention
  • the bioassay method of alfalfa aphid is the dipping method.
  • the fresh corn leaves were immersed in the solution prepared in (1) above for 3 seconds, and then dried at room temperature for the test insects to eat.
  • Each treatment group used 10 armyworms, and set 3 groups to repeat. After 72 hours, check and calculate the mortality of the test insects.
  • Ingestion method quantitatively take stock solution I, add appropriate amount of Tween and stir evenly, dilute with 33% honey water to dissolve, then transfer to a volumetric flask for constant volume, make up test solution 1, and use 33 for test solution 1 Dilute the test sample into a series of different concentrations with% honey water, take an appropriate amount of the drug solution into a 50mL small beaker, soak the drug solution with 0.3g of absorbent cotton to a saturated state, spread the absorbent cotton impregnated with the drug solution on the test sarong net, and place it upside down with the beaker On the absorbent cotton, the test bees ingest the medicated honey water on the absorbent cotton through the mesh. On the test tube rack covered with black cloth. The content of acetone and Tween 80 in the adjuvant control was the same as that in the highest concentration liquid.
  • test data was processed with statistical software SPSS 12.0, and the median lethal concentration value (acute ingestion toxicity), the median lethal dose value (acute contact toxicity) and 95% confidence limit of the original drug to bees at 24 and 48 hours were calculated.
  • the bioassay results were processed by Polo analysis software, and the virulence regression curve equation, LC 50 , 95% confidence limit and correlation coefficient of the tested drugs were calculated respectively.
  • Relative toxicity [(insecticide + synergist) LD 50 or LC 50 ]/[insecticide LD 50 or LC 50 ]
  • the lethality of alfalfa aphids at a concentration of 1 mg/L of b imidacloprid is 30%.
  • Example 40 Comparison of synergistic activity between the compound of this patent and IPPA08 compound
  • the experimental method is the same as the bioassay method of alfalfa aphid in Example 39.
  • IPPA08 serves as a comparison.
  • Figure 1 shows the toxic effect of IPPA08 and compound 4 on imidacloprid.
  • Table 2 shows the comparison results of the synergistic activity of the compound of the application and the IPPA08 compound.
  • Example 41 Selectivity of compound 4 and IPPA08 to honeybees
  • the experimental method is the same as the bioassay method for honeybees in Example 39.
  • the results are shown in Table 3 and Table 4.
  • the data in Table 3 shows that when compound 4 is used in combination with imidacloprid, the LD 50 value of imidacloprid's contact toxicity and oral toxicity to honeybees does not decrease with the increase of compound 4 dosage.
  • the data in Table 4 show that when the compound IPPA08 is combined with imidacloprid, the LD 50 value of the oral toxicity of imidacloprid to honeybees decreases with the increase of the compound IPPA08 dosage.
  • Table 2 when compound 4 is used in combination with imidacloprid, it shows a significant synergistic effect and has good selectivity for honeybees.
  • Example 42 Synergistic effects of compounds on rynnidine receptor inhibitors, organophosphorus insecticides, carbamate insecticides, bioinsecticides and pymetrozine
  • the experimental method is the same as the bioassay method of armyworm, alfalfa aphid and Tetranychus cinnabarinus in Example 39.
  • the concentration of chlorantraniliprole is 0.1 mg/L, and the lethality to armyworm is 35%.

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  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

L'invention concerne l'utilisation d'un composé hétérocyclique à pont oxygène à huit chaînons utilisé en tant que synergiste insecticide ayant une sélectivité vis-à-vis d'une abeille. La structure du composé hétérocyclique à huit chaînons à pont oxygène est représentée par la formule I. Les définitions des substituants dans la formule sont telles que définies dans la description et les revendications. Le composé hétérocyclique à pont d'oxygène à huit chaînons dans la formule I de la présente invention peut améliorer significativement l'effet insecticide d'un insecticide, présente une sélectivité vis-à-vis des abeilles, et n'augmente pas la toxicité de l'insecticide vis-à-vis des abeilles.
PCT/CN2021/073608 2020-02-24 2021-01-25 Utilisation d'un composé hétérocyclique à pont d'oxygène à huit chaînons utilisé en tant que synergiste insecticide présentant une sélectivité vis-à-vis de l'abeille WO2021169699A1 (fr)

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CN202010112193.5A CN111165505A (zh) 2020-02-24 2020-02-24 八元氧桥杂环化合物作为蜜蜂选择性杀虫剂增效剂的用途

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