WO2011069456A1 - 双联和氧桥杂环新烟碱化合物及其制备方法 - Google Patents

双联和氧桥杂环新烟碱化合物及其制备方法 Download PDF

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Publication number
WO2011069456A1
WO2011069456A1 PCT/CN2010/079591 CN2010079591W WO2011069456A1 WO 2011069456 A1 WO2011069456 A1 WO 2011069456A1 CN 2010079591 W CN2010079591 W CN 2010079591W WO 2011069456 A1 WO2011069456 A1 WO 2011069456A1
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compound
group
formula
carbonyl
hours
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PCT/CN2010/079591
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English (en)
French (fr)
Chinese (zh)
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钱旭红
李忠
邵旭升
徐晓勇
须志平
宋恭华
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华东理工大学
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Priority to JP2012542350A priority Critical patent/JP5600750B2/ja
Application filed by 华东理工大学 filed Critical 华东理工大学
Priority to AU2010330474A priority patent/AU2010330474B2/en
Priority to KR1020127017848A priority patent/KR101504575B1/ko
Priority to EP10835491.1A priority patent/EP2511279B1/en
Priority to CA2783504A priority patent/CA2783504C/en
Priority to UAA201208318A priority patent/UA106256C2/ru
Priority to MX2012006663A priority patent/MX2012006663A/es
Priority to BR112012013846A priority patent/BR112012013846A2/pt
Priority to US13/514,460 priority patent/US8809319B2/en
Priority to RU2012127868/04A priority patent/RU2531920C2/ru
Publication of WO2011069456A1 publication Critical patent/WO2011069456A1/zh
Priority to IL220237A priority patent/IL220237A/en
Priority to ZA2012/05074A priority patent/ZA201205074B/en

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    • 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
    • C07D498/02—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 two hetero rings
    • C07D498/08—Bridged systems
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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

  • Double and oxygen bridge heterocyclic neonicotinoid compound and preparation method thereof Double and oxygen bridge heterocyclic neonicotinoid compound and preparation method thereof
  • the invention relates to a novel neonicotinoid insecticide, a preparation method and application thereof.
  • the present invention relates to a bi- and oxygen-bridged heterocyclic neonicotinoid compound constructed from an imidacloprid nitromethylene analog and a dialdehyde, and a process for the preparation thereof.
  • the neonicotinoid insecticide represented by imidacloprid has high insecticidal activity, wide insecticidal spectrum, low toxicity to mammals and aquatic animals, good systemic property and appropriate field stability and environmental friendliness. An important hot spot for the creation of new pesticides. Later, a series of nicotinic insecticides such as thiacloprid, clothianidin, thiamethoxam, acetamiprid, nitenpyram, and dinotefuran have been developed (see European patents 247477, 296453, 685477, 235725, 235725, 3 15826, 192060, 244777, 0386565, 580553, and 1031566, Japanese Patent Nos. 62292965, 8259568, 8291171, and 7242633).
  • the present invention provides a new and more effective insecticide, solves the problem of resistance of neonicotinoid insecticides, expands the insecticidal spectrum, and solves the problems in the prior art.
  • Another object of the invention is to provide protection for growing and harvested crops from insect attack and infestation.
  • the invention provides an oxygen bridged heterocyclic neonicotinoid compound selected from the group consisting of a compound having the structure of formula (A) or (; B), or an optical isomer or agrochemically acceptable compound of said compound Accepted salt -
  • an oxygen bridged heterocyclic neonicotinoid compound selected from the group consisting of a compound having the structure of formula (A) or (; B), or an optical isomer or agrochemically acceptable compound of said compound Accepted salt -
  • A oxygen bridged heterocyclic neonicotinoid compound
  • B an optical isomer or agrochemically acceptable compound of said compound Accepted salt -
  • ⁇ is a five- or six-membered heterocyclic group containing nitrogen, oxygen and/or sulfur, a halogenated five- or six-membered heterocyclic group containing nitrogen, oxygen and/or sulfur, or a substituted or unsubstituted phenyl group, Wherein the substituent is one or more selected from the group consisting of halogen, CM halogenated fluorenyl or chloroalkoxy;
  • R 3 are each independently H, d- 6 alkyl with, allyl, benzyl, d- 4 -d- 4 alkoxyalkyl group, alkoxy embankment - carbonyl, phenoxycarbonyl, C 2 - 6 alkynyl yl - carbonyl group, C 2 - 3 alkenyl - carbonyl group, C 3 - 6 cycloalkyl - carbonyl, benzoyl, or substituted with one or more substituents selected from a halogen atom, 4 alkyl, halo alkyl with D- 4, a benzoyl group substituted with a d- 4 methoxy group and a CM fluorenyl-carbonyl substituent, a furanylcarbonyl group or an N,N-dimethylcarbonyl group, or R 3 and a combination of -CH 2 -CH 2 -, -CH 2 -CH 2 -CH 2 - or -CH 2 -
  • R is a substituent on a hetero atom selected from H, d- 6 alkyl, allyl, benzyl, phenyl, d- 4 methoxy-d- 4 alkyl, d- 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 ⁇ halogenated fluorenyl a benzoyl group substituted with a d- 8 saturated or unsaturated fluorenyl group or a substituent of a decyloxy group and a fluorenyl-carbonyl group, a furanylcarbonyl group or a hydrazine, a fluorenyl-dimethylcarbonyl group;
  • Y is nitro, cyano, trifluoromethyl, trifluoroacetyl or trifluoromethanesulfonyl.
  • the oxygen bridge heterocyclic neonicotinoid compound is selected from the group consisting of
  • oxygen bridge heterocyclic neonicotinoid compound is selected from the group consisting of
  • the oxygen bridge heterocyclic neonicotinoid compound is an antagonist of an insect nicotinic acetylcholine receptor.
  • the oxygen bridged heterocyclic neonicotinoid compounds (la) and (lb) are 2 to 30 times more active against imidacloprid resistant brown planthopper and whitefly.
  • the present invention provides an agricultural composition comprising -
  • the invention relates to the use of the agricultural composition for killing or preventing agricultural pests, Pests and pests that are harmful to animal health; or insecticide compositions used to kill or prevent agricultural pests, sanitary pests, and animal health hazards.
  • the invention provides a pesticidal and/or pest control method comprising applying the above agricultural composition to a plant body that is or may be subject to pests, soil surrounding it, or the environment.
  • the present invention relates to the use of the above compounds, their optical isomers or agrochemically acceptable salts, or a combination thereof, in the preparation of a pesticide composition.
  • the present invention provides a process for the preparation of the above compound, its optical isomer or agrochemically acceptable salt, the method comprising the steps of:
  • the compound of formula (a) is reacted with a compound of formula (a) or (c) in the presence of a catalytic acid at room temperature to produce a compound of formula (A) (B),
  • R 3 , R 5 , R 6 , R 7 , R 8 , R 9 and Y are as defined above.
  • the method comprises the steps of: - in acetonitrile, in the presence of a catalytic amount of an acid, at room temperature, at a temperature of from 2 to 24 hours to obtain a compound of formula (la):
  • the inventors of the present invention have studied the imidacloprid nitromethylene structure of the existing imidacloprid nitromethylene-based neonicotinoid insecticide through the dialdehyde and the imidacloprid nitromethylene compound through long-term and in-depth research.
  • a novel neonicotinoid compound was synthesized, which showed a marked increase in insecticidal activity and an expanded insecticidal spectrum.
  • the inventors have completed the present invention.
  • mercapto refers to a straight or branched alkyl group having from 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl. , tert-butyl, or the like.
  • d- 4 methoxy refers to a straight or branched alkoxy group having from 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutylene.
  • halogen means fluoro, chloro, bromo, or iodo.
  • halogenated refers to a group substituted with one or more of the above halogen atoms, which may be the same or different, such as a trifluoromethyl group, a pentafluoroethyl group, or the like.
  • five- or six-membered heterocyclic group refers to a five- or six-membered ring containing one or more heteroatoms selected from nitrogen, oxygen or sulfur, such as pyridyl, thiazolyl, pyrimidinyl, tetrahydrofuranyl, or Azolyl and the like.
  • the compounds of the invention can be synthesized by the reaction steps described above.
  • the compound of formula (Id) (ld)
  • the synthesis of the compound of formula (2a) is as follows:
  • the compounds of formula (2a)-(2e) can be prepared by the following reaction:
  • active substance of the invention or “active compound of the invention” means a compound of the invention, an optical isomer or a pesticidally acceptable salt thereof, which has significantly enhanced insecticidal activity, and an expanded insecticidal activity. Spectrum.
  • a pesticidally acceptable salt means that the anion of the salt is known and acceptable in forming the pharmaceutically acceptable salt of the pesticide.
  • the salt is preferably water soluble.
  • Suitable acid addition salts formed from the compounds of the formulae (A) and (B) include salts formed with inorganic acids, such as hydrochlorides, phosphates, sulfates, nitrates; and salts formed from organic acids, such as Acetate, benzoate.
  • the active material of the present invention can be used for controlling and eliminating a wide range of agricultural and forestry plant pests, storing cereal pests, public health pests, and pests that are harmful to animal health.
  • insecticide is a general term for substances having the action of controlling all the pests mentioned above. Examples of pests include, but are not limited to, Coleoptera: Sitophilus zeamais, ⁇ (2 0 //iTM castaneum), potato ticket melon
  • Pests that are harmful to animal health include BoopMus micmphis, long-horned blood clams
  • Hyalomama anatolicum cowhide! fe ⁇ ( Hypo derma spp. ), Fasciola hepatica, Moniezia blanchard, Oster nematode (Ostertagia spp.), Trypanosoma enansi, Babesia bigemina, etc.
  • the compound of the invention has special effects especially for sucking and sucking mouthparts pests, such as aphids, leafhoppers, planthoppers, thrips, whiteflies and the like.
  • Insecticide composition containing the active substance of the present invention is aphids, leafhoppers, planthoppers, thrips, whiteflies and the like.
  • the active substance of the present invention can be prepared into a pesticide composition in a conventional manner.
  • These active compounds can be formulated into conventional preparations such as solutions, emulsions, suspensions, powders, foams, pastes, granules; aerosols, natural and synthetic materials impregnated with active substances, Microcapsules in polymers, coatings for seeds, and preparations for use with combustion devices, such as smoking cartridges, smoked cans and smokers, as well as ULV cold mist and hot fog ( Warm mist) formulation.
  • compositions can be produced by known methods, for example, by mixing the active compound with an extender which is a liquid or liquefied gas or solid diluent or carrier, and optionally a surfactant which is emulsified.
  • an extender which is a liquid or liquefied gas or solid diluent or carrier
  • a surfactant which is emulsified.
  • Agents and/or dispersants and/or foam formers for example, when water is used as an extender, an organic solvent can also be used as an auxiliary.
  • a liquid solvent as a diluent or a carrier, such as: aromatic hydrocarbons such as xylene, toluene or decylnaphthalene; 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 Ketone or cyclohexanone; or less common polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatic hydrocarbons such as xylene, toluene or decylnaphthalene
  • chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride or Dichloromethane
  • the diluent or carrier for the liquefied gas refers to a liquid which will become a gas at normal temperature and normal pressure, such as an aerosol propellant such as a halogenated hydrocarbon, and butyl hydrazine, propylene carbonate, nitrogen gas and carbon dioxide.
  • an aerosol propellant such as a halogenated hydrocarbon, and butyl hydrazine, propylene carbonate, nitrogen gas and carbon dioxide.
  • Solid supports can be used as natural minerals on the ground, such as kaolin, clay, talc, quartz, activated clay, montmorillonite, or diatomaceous earth, and ground synthetic minerals such as highly dispersed silicic acid, alumina and silicates.
  • the solid carrier for the granules is a ground and graded natural stone, such as calcite, marble, pumice, sepiolite and dolomite, as well as inorganic and organic coarse powder synthetic particles, and organic materials such as sawdust, coconut shell, Corn cobs and granules of tobacco stems.
  • Nonionic and anionic emulsified columns can be used as emulsifiers and I or foam formers.
  • emulsifiers and I or foam formers polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, such as alkylaryl polyglycol ethers, mercaptosulfonates, alkyl sulfates, arylsulfonates, and white Protein hydrolysate.
  • Dispersing agents include, for example, lignin sulfite waste liquid and methyl cellulose.
  • Binders such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or emulsions such as gum arabic, polyvinyl alcohol and polyvinyl acetate may be used in the formulation.
  • Colorants such as inorganic dyes such as iron oxide, oxidized diamonds and Prussian blue; organic dyes such as organic dyes such as azo dyes or metal phthalocyanine dyes; and trace nutrients such as iron, lanthanum, boron, copper may be used. , cobalt, aluminum and zinc salts, etc.
  • the active compounds of the present invention may be present in a commercial preparation or in a dosage form prepared from these preparations in combination with other active compounds, including but not limited to: insecticides, baits, bactericides, Acaricides, killing lines, fungicides, growth control agents, etc.
  • Insecticides include, for example, phosphates, carbamates, pyrethroids, chlorinated hydrocarbons, benzoylureas, nematodes, and microbial-derived substances such as avermectin.
  • the active compounds of the invention may also be formulated as a mixture with synergists in their commercial preparations in the dosage forms prepared from these preparations.
  • Synergists are compounds which increase the action of the active compound. Since the active compound itself is active, it is not necessary to add a synergist.
  • These formulations usually contain from 0.001 to 99.99% by weight, preferably from 0.01 to 99.9% by weight, more preferably from 0.05 to 90% by weight, of the active compound of the invention, of the insecticidal composition.
  • the concentration of the active compound in the dosage form prepared from the commercial preparation can be varied within a wide range.
  • the concentration of active compound in the dosage form used may range from 0.000000 l to 100% (g/v), preferably between 0.0001 and 1%.
  • Example 9 10-(4-Chlorobenzyl)-4-nitro-9-oxa-1 1,12-dihydroimidazo[2,3-albicyclo"3,3,11 ⁇ -3- Alkene (compound 2d)
  • a 25% aqueous solution of glutaraldehyde and a catalytic amount of HC1 were placed in a 50 ml round bottom flask. Stir at room temperature and TLC is followed by reaction. After the completion of the reaction, the solvent was removed, and the residue was purified by column chromatography to yield pale yellow powdery product.
  • Example 1 1 Insecticidal activity test of the compound of the present invention
  • Aphids belong to the homopteran pests and have a sucker, which is a common crop pest.
  • the soybean meal craccivora was used as the test object and tested by the dipping method.
  • Test method Accurately weigh each sample, add DMSO 2 mL and 18 mL water, add three drops of emulsifier 2201 into a liquid, blank with DMSO 2 mL and 18 mL water, add three drops of emulsifier 2201. Soak a certain number of insects to be tested with broad bean leaves in the liquid for 3-5 seconds, remove and dry, transfer the test insects and foodstuffs into a clean container, place in a dry thermostat recovery room, and check the test insects after 24 hours. Poisoning deaths. The results are shown in Table 1 below.
  • Rice brown planthopper is a homopteran pest with a sucker and is a common crop pest.
  • the rice brown planthopper (; N//aparvato / wgew was used as the test object, and the microdropping method reported by Nagata was used.
  • Procedure Select un-matted females with feathering for 2-3 days as test subjects, dilute the compounds to a series of concentrations with acetone, and test the insect paralysis with carbon dioxide, using a manual micro-dropper (Burkard Manufacturing Co. Ltd, Rickmansworth , UK) Drop the drug drop (0.08 L) before the test insect On the chest and back. Approximately 30 adults were treated at each concentration and each treatment was repeated 3 times. Take acetone as a control. The treated adults were housed on soilless cultivated rice seedlings in an incubator (20 x 20 x 10 cm) at a temperature of 25 ⁇ 1 V and 16 (L) / 8 (D) hours. The results were checked after 48 hours and LD 5 was calculated using standard probability analysis. value. The results are shown in Table 2 below.
  • the second instar larvae were tested with the larvae of Pseudaktia separate Walker, and the leaf leaching method was used.
  • the armyworm is an important heterophylla lepidopteran pest. It has a wide application range and is suitable for the determination of virulence, contact and residual effects such as stomach poisoning, contact and residual effects, and insect toxicology. For the screening test of new compounds, the test of the armyworm killing activity was carried out according to the method reported in the literature.
  • Operation process of dip-leaf method Accurately weigh each sample, add DMSO (2 mL) and 18 mL of water separately, then add three drops of emulsifier 2201 (provided by Shanghai Pesticide Factory) to prepare liquid medicine, blank DMSO (2 mL) And 28 mL of clear water, add three drops of emulsifier 2201. Tear fresh corn leaves into small pieces, soak them in the liquid for about 5 seconds, take them out and dry them, put them into a 100 mL jar, and put about 20 second-instar larvae, white gauze for the jar. The rubber band was tightened, and the corn immersed in the liquid was continuously fed, and the mortality of the larva was checked after 5 days.
  • the compound (la) was subjected to electrophysiological experiments and isotopic label substitution experiments, and the compound (la) inhibited the agonist reaction; the compound (la) expressed ⁇ ⁇ to the nicotinic acetylcholine receptor and oocyte of the United States.
  • the 1/1 2 receptor has no agonistic effect; the compound (la) inhibits the agonist acetylcholine response, and these experiments indicate that the compound is an antagonist of nicotinic acetylcholine receptors (nAChRs).
  • Example 13 Preparation of a Pesticide Composition Containing a Compound of the Invention
  • the following components were prepared in proportion: 25% by weight of the compound la-le and 2a-2e; 5% polyoxyethylene sorbitol hexaoleate; 70% higher aliphatic hydrocarbon oil.
  • the components were ground together in a sanding mill until the solid particles fell below about 5 microns.
  • the resulting viscous suspension can be used as it is, but it can also be used after emulsification in water.
  • the following components were prepared in proportion: 25% of the compounds la-le and 2a-2e; 3% hydrate attapulgit; 10% calcium lignosulfonate; 0.5% sodium dihydrogen phosphate; 61.5 %water.
  • the components are ground together in a ball mill until the solid particles fall below about 10 microns. This aqueous suspension can be used directly.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Agronomy & Crop Science (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
PCT/CN2010/079591 2009-12-09 2010-12-09 双联和氧桥杂环新烟碱化合物及其制备方法 WO2011069456A1 (zh)

Priority Applications (12)

Application Number Priority Date Filing Date Title
UAA201208318A UA106256C2 (ru) 2009-12-09 2010-12-09 Двухвалентные гетероциклические родственные с никотином соединения, которые имеют кислородный мостик, и способы их приготовления
AU2010330474A AU2010330474B2 (en) 2009-12-09 2010-12-09 Divalent and oxabridged heterocyclic neonicotinoid compounds and preparation methods thereof
KR1020127017848A KR101504575B1 (ko) 2009-12-09 2010-12-09 2가의 산소 브릿지된 헤테로사이클릭 네오니코티노이드 화합물 및 그의 제조방법
EP10835491.1A EP2511279B1 (en) 2009-12-09 2010-12-09 Divalent and oxabridged heterocyclic neonicotinoid compounds and preparation methods thereof
CA2783504A CA2783504C (en) 2009-12-09 2010-12-09 Divalent and oxabridged heterocyclic nicotine related compounds and preparation methods thereof
JP2012542350A JP5600750B2 (ja) 2009-12-09 2010-12-09 エポキシ基含有複素環式ネオニコチノイド化合物及びその製造方法、農業用組成物及びその使用、害虫防除方法
MX2012006663A MX2012006663A (es) 2009-12-09 2010-12-09 Compuestos de neonicotinoides heterociclicos divalentes y compuestos oxa y metodos de preparacion de los mismos.
RU2012127868/04A RU2531920C2 (ru) 2009-12-09 2010-12-09 Двухвалентные и гетероциклические производные никотина с оксо-мостиком и способы их получения
US13/514,460 US8809319B2 (en) 2009-12-09 2010-12-09 Substituted 8-oxa-10,11-dihydroimidazo[2,3-a]bicyclo[3.2.1]oct-3-enes and use thereof as an insecticide
BR112012013846A BR112012013846A2 (pt) 2009-12-09 2010-12-09 composto relacionado á nicotina heterocíclico ligado por ponte de oxigênio ou um isômero óptico ou sal agroquimicamente aceitável do mesmo,composição agroquímica,(*)aplicação da composição agroquímica, método para preparar o composto relacionado á nicotina heterocíclico ligado por ponte de oxigênio ou um isômero óptico ou sal agroquimicamente aceitável do mesmo e método para controlar pragas
IL220237A IL220237A (en) 2009-12-09 2012-06-07 Compounds closest to heterocyclic heterotinous nicotine compounds with oxygen bridges and methods for preparing them
ZA2012/05074A ZA201205074B (en) 2009-12-09 2012-07-06 Divalent and oxabridged heterocyclic neonicotinoid compounds and preparation methods thereof

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CN200910258534.3 2009-12-09
CN200910258534.3A CN102093389B (zh) 2009-12-09 2009-12-09 双联和氧桥杂环新烟碱化合物及其制备方法

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US (1) US8809319B2 (pt)
EP (1) EP2511279B1 (pt)
JP (1) JP5600750B2 (pt)
KR (1) KR101504575B1 (pt)
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CO6561790A2 (es) 2012-11-15
JP2013513553A (ja) 2013-04-22
CA2783504C (en) 2013-07-09
IL220237A (en) 2017-08-31
MX2012006663A (es) 2012-10-15
IL220237A0 (en) 2012-07-31
US8809319B2 (en) 2014-08-19
KR20120094111A (ko) 2012-08-23
EP2511279B1 (en) 2015-11-11
AU2010330474A1 (en) 2012-07-26
CL2012001517A1 (es) 2013-01-11
EP2511279A4 (en) 2013-05-01
EP2511279A1 (en) 2012-10-17
CN102093389A (zh) 2011-06-15
US20120245126A1 (en) 2012-09-27
CA2783504A1 (en) 2011-06-16
CR20120361A (es) 2012-12-18
AU2010330474B2 (en) 2015-01-29
BR112012013846A2 (pt) 2015-09-15
JP5600750B2 (ja) 2014-10-01
RU2531920C2 (ru) 2014-10-27
RU2012127868A (ru) 2014-01-20
UA106256C2 (ru) 2014-08-11
CN102093389B (zh) 2014-11-19

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