WO2002057262A2 - Amines bicycliques utilisees comme insecticides - Google Patents

Amines bicycliques utilisees comme insecticides Download PDF

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Publication number
WO2002057262A2
WO2002057262A2 PCT/GB2002/000152 GB0200152W WO02057262A2 WO 2002057262 A2 WO2002057262 A2 WO 2002057262A2 GB 0200152 W GB0200152 W GB 0200152W WO 02057262 A2 WO02057262 A2 WO 02057262A2
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WO
WIPO (PCT)
Prior art keywords
optionally substituted
alkyl
compound
formula
substituted
Prior art date
Application number
PCT/GB2002/000152
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English (en)
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WO2002057262A3 (fr
Inventor
Roger Salmon
Original Assignee
Syngenta Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GB0101228A external-priority patent/GB0101228D0/en
Priority claimed from GB0117035A external-priority patent/GB0117035D0/en
Application filed by Syngenta Limited filed Critical Syngenta Limited
Priority to AU2002219383A priority Critical patent/AU2002219383A1/en
Publication of WO2002057262A2 publication Critical patent/WO2002057262A2/fr
Publication of WO2002057262A3 publication Critical patent/WO2002057262A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals

Definitions

  • WO96/37494 there are disclosed various insecticidal compounds based upon bicyclic amines. The applicants have found a small group of compounds which have a particular substitution pattern and which are particularly active as insecticides.
  • aryl and aromatic ring system refer to ring systems which may be mono-, bi- or tricyclic. Examples of such rings include phenyl, naphthalenyl, anthracenyl or phenanthrenyl, preferably phenyl.
  • heteroaryl refers to an aromatic ring system containing at least one heteroatom and consisting either of a single ring or of two or more fused rings. Preferably, single rings will contain up to three and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulphur.
  • halogen includes fluorine, chlorine, bromine and iodine.
  • Haloalkyl groups are alkyl groups which are substituted with one or more of the same or different halogen atoms and are, for example, CF 3 , CF C1, CH CF 3 , CH CH 2 CF 3 , CH 2 (CF 2 ) 2 CH 3 , CH 2 CHF 2 or CH 2 CF 2 CF 2 CF 3 .
  • Suitable acid addition salts include those with an inorganic acid such as hydrochloric, hydrobromic, sulfuric, nitric and phosphoric acids, or an organic carboxyhc acid such as oxalic, tartaric, lactic, butyric, toluic, hexanoic and phthalic acids, or sulphonic acids such as methane, benzene and toluene sulphonic acids.
  • an inorganic acid such as hydrochloric, hydrobromic, sulfuric, nitric and phosphoric acids
  • an organic carboxyhc acid such as oxalic, tartaric, lactic, butyric, toluic, hexanoic and phthalic acids
  • sulphonic acids such as methane, benzene and toluene sulphonic acids.
  • I and X is a leaving group with copper(l) cyanide in a suitable solvent.
  • the leaving group may for example be halogen such as chloro, bromo or iodo, or methanesulfonyloxy, or para- toluenesulfonyloxy.
  • Suitable solvents include N-methyl pyrrolidin-2-one or N,N- dimethylacetamide.
  • the reaction is suitably performed at a temperature of 100- 200°C.
  • X is chlorine, the addition of copper (1) iodide to the reaction gives improved conversions and rates of reaction.
  • Soluble powders may be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulphate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).
  • water-soluble inorganic salts such as sodium bicarbonate, sodium carbonate or magnesium sulphate
  • water-soluble organic solids such as a polysaccharide
  • WP Wettable powders
  • WG Water dispersible granules
  • Granules may be formed either by granulating a mixture of a compound of formula (I) and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing a compound of formula (I) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of formula (I) (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulphates or phosphates) and drying if necessary.
  • a hard core material such as sands, silicates, mineral carbonates, sulphates or phosphates
  • DC Dispersible Concentrates
  • a compound of formula (I) may be prepared by dissolving a compound of formula (I) in water or an organic solvent, such as a ketone, alcohol or glycol ether.
  • organic solvent such as a ketone, alcohol or glycol ether.
  • surface active agent for example to improve water dilution or prevent crystallisation in a spray tank.
  • Emulsifiable concentrates or oil-in-water emulsions (EW) may be prepared by dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents).
  • Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLNESSO 150 and SOLNESSO 200; SOLNESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), ⁇ -alkylpyrrolidones (such as ⁇ -methylpyrrolidone or ⁇ -octylpyrrolidone), dimethyl amides of fatty acids (such as Cs- o fatty acid dimethylamide) and chlorinated hydrocarbons.
  • aromatic hydrocarbons such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLNESSO 150 and SOLNESSO 200; SOLNESSO is a Registered Trade Mark
  • ketones such as
  • An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment.
  • Preparation of an EW involves obtaining a compound of formula (I) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifiying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion.
  • Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.
  • Microemulsions may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation.
  • a compound of formula (I) is present initially in either the water or the solvent/SFA blend.
  • Suitable solvents for use in MEs include those hereinbefore described for use in in ECs or in EWs.
  • An ME may be either an oil-in-water or a water-in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation.
  • An ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion.
  • SC Suspension concentrates
  • SCs may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula (I).
  • SCs may be prepared by ball or bead milling the solid compound of formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound.
  • One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle.
  • a compound of formula (I) may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.
  • Aerosol formulations comprise a compound of formula (I) and a suitable propellant (for example n-butane).
  • a compound of formula (I) may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non-pressurised, hand-actuated spray pumps.
  • a compound of formula (I) may be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound.
  • Capsule suspensions may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerisation stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of formula (I) and, optionally, a carrier or diluent therefor.
  • the polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure.
  • the compositions may provide for controlled release of the compound of formula (I) and they may be used for seed treatment.
  • a compound of formula (I) may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.
  • a composition may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of formula (I)).
  • additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of formula (I)).
  • a compound of formula (I) may also be formulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a fiowable concentrate (FS), a solution (LS) or a capsule suspension (CS).
  • DS powder for dry seed treatment
  • SS water soluble powder
  • WS water dispersible powder for slurry treatment
  • CS capsule suspension
  • the preparations of DS, SS, WS, FS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above.
  • Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier).
  • Wetting agents, dispersing agents and emulsifying agents may be surface SFAs of the cationic, anionic, amphoteric or non-ionic type.
  • Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts.
  • Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), salts of sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate, calcium dodecylbenzenesulphonate, butylnaphthalene sulphonate and mixtures of sodium di-i-ropropyl- and tri-isopropyl-naphthalene sulphonates), ether sulphates, alcohol ether sulphates (for example sodium laureth-3-sulphate), ether carboxylates (for example sodium laureth-3- carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid
  • Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.
  • Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.
  • Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrohdone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).
  • hydrophilic colloids such as polysaccharides, polyvinylpyrrohdone or sodium carboxymethylcellulose
  • swelling clays such as bentonite or attapulgite
  • a compound of formula (I) may be applied by any of the known means of applying pesticidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapour or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water-soluble bag) in soil or an aqueous environment.
  • a locus of the pests such as a habitat of the pests, or a growing plant liable to infestation by the pests
  • a compound of formula (I) may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.
  • compositions for use as aqueous preparations are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to water before use.
  • These concentrates which may include DCs, SCs, ECs, EWs, MEs SGs, SPs, WPs, WGs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment.
  • Such aqueous preparations may contain varying amounts of a compound of formula (I) (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.
  • a compound of formula (I) may be used in mixtures with fertilisers (for example nitrogen-, potassium- or phosphorus-containing fertilisers).
  • Suitable formulation types include granules of fertihser.
  • the mixtures suitably contain up to 25% by weight of the compound of formula (I).
  • the invention therefore also provides a fertiliser composition comprising a fertiliser and a compound of formula (I).
  • the compound of formula (I) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide such as azoxystrobin, synergist, herbicide or plant growth regulator where appropriate.
  • An additional active ingredient may: provide a composition having a broader spectrum of activity or increased persistence at a locus; synergise the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of formula (I); or help to overcome or prevent the development of resistance to individual components.
  • the particular additional active ingredient will depend upon the intended utility of the composition.
  • Suitable pesticides include the following: a) Pyrethroids, such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, s-bioallethrin, fenfluthrin, prallethrin or 5-benzyl-3-furylmethyl-(E)-(lR,3S)-2,2-dimethyl- 3-(2-oxothiolan-3-yhdenemethyl)cyclopropane carboxylate; b) Organophosphates, such as, profenofos, sulprofos, acephat
  • pesticides having particular targets may be employed in the composition, if appropriate for the intended utility of the composition.
  • selective insecticides for particular crops for example stemborer specific insecticides (such as cartap) or hopper specific insecticides (such as buprofezin) for use in rice may be employed.
  • insecticides or acaricides specific for particular insect species/stages may also be included in the compositions (for example acaricidal ovo-larvicides, such as clofentezine, flubenzimine, hexythiazox or tetradifon; acaricidal motilicides, such as dicofol or propargite; acaricides, such as bromopropylate or chlorobenzilate; or growth regulators, such as hydramethylnon, cyromazine, methoprene, chlorfluazuron or diflubenzuron).
  • acaricidal ovo-larvicides such as clofentezine, flubenzimine, hexythiazox or tetradifon
  • acaricidal motilicides such as dicofol or propargite
  • acaricides such as bromopropylate or chlorobenzilate
  • growth regulators such
  • synergists for use in the compositions include piperonyl butoxide, sesamex, safroxan and dodecyl imidazole.
  • Suitable herbicides and plant-growth regulators for inclusion in the compositions will depend upon the intended target and the effect required.
  • An example of a rice selective herbicide which may be included is propanil.
  • An example of a plant growth regulator for use in cotton is PIXTM.
  • Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type.
  • other formulation types may be prepared.
  • one active ingredient is a water insoluble solid and the other, a water insoluble liquid
  • the resultant composition is a suspoemulsion (SE) formulation.
  • SE suspoemulsion
  • EXAMPLE 5 This Example illustrates the preparation of compound 5 of Table I: endo-3-cvano-exo-3-(5- cyanopyrid-3-yl)-8-formyl-8-azabicyclo[3.2.1joctane.
  • EXAMPLE 7 This Example illustrates the preparation of compound 8 of Table I: 8-(but-2-ynyl)-endo-3- cyano-exo-3-(5-cyanopyrid-3-yl)- 8-azabicyclo[3.2. ljoctane.
  • exo-3-(5-bromopyrid-3-yl)-endo-3-cyano-8-(N,N- dimethylacetamido)-8-azabicyclo[3.2.1joctane was reacted with copper (1) cyanide to give endo-3-cyano-exo-3-(5-cyanopyrid-3-yl)-8-(N,N-dimethylacetamido -8- azabicyclo[3.2.1joctane as colourless sohd.

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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)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne un composé de formule (I). A représente CH2-CH2- ou CH=CH-; R représente hydrogène, CHO, COOC1-C10 alkyle, C2-C10 alkyle éventuellement substitué, méthyle substitué, C1-C10 alcoxy éventuellement substitué, C2-C10 alcényloxy éventuellement substitué, aryle éventuellement substitué, hétéroaryle éventuellement substitué, C2-C10 alcényle éventuellement substitué, C3-C10 alkynyle éventuellement substitué ou C3-C7 cycloalkyle éventuellement substitué; ainsi que des sels d'addition d'acide, des sels d'ammonium quaternaire et des N-oxydes qui en découlent. Les composés sont utiles comme insecticides.
PCT/GB2002/000152 2001-01-17 2002-01-15 Amines bicycliques utilisees comme insecticides WO2002057262A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002219383A AU2002219383A1 (en) 2001-01-17 2002-01-15 Bicyclic amines as insecticides

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB0101228A GB0101228D0 (en) 2001-01-17 2001-01-17 Chemical compounds
GB0101228.5 2001-01-17
GB0117035A GB0117035D0 (en) 2001-07-12 2001-07-12 Chemical compounds
GB0117035.6 2001-07-12

Publications (2)

Publication Number Publication Date
WO2002057262A2 true WO2002057262A2 (fr) 2002-07-25
WO2002057262A3 WO2002057262A3 (fr) 2007-10-25

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2002/000152 WO2002057262A2 (fr) 2001-01-17 2002-01-15 Amines bicycliques utilisees comme insecticides

Country Status (2)

Country Link
AU (1) AU2002219383A1 (fr)
WO (1) WO2002057262A2 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2378181A (en) * 2001-07-12 2003-02-05 Syngenta Ltd Insecticidal bicyclic amines
CN103570729A (zh) * 2012-07-26 2014-02-12 华东理工大学 环烯酮构建的二环新烟碱化合物及其制备方法和应用
WO2014154487A1 (fr) * 2013-03-28 2014-10-02 Syngenta Participations Ag Procédés de lutte contre des organismes nuisibles résistant aux néonicotinoïdes
WO2014154486A1 (fr) * 2013-03-28 2014-10-02 Syngenta Participations Ag Procédés de lutte contre des organismes nuisibles résistant aux néonicotinoïdes
WO2014154488A1 (fr) * 2013-03-28 2014-10-02 Syngenta Participations Ag Procédés de lutte contre des organismes nuisibles résistant aux néonicotinoïdes
WO2015032617A1 (fr) * 2013-09-06 2015-03-12 Syngenta Participations Ag Composés insecticides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998025924A1 (fr) * 1996-11-26 1998-06-18 Zeneca Limited Derives de 8-azabicyclo[3.2.1.]octane-, 8-azabicyclo[3.2.1]oct-6-ene-, 9-azabicyclo[3.3.1]nonane-, 9-aza-3-oxabicyclo[3.3.1]nonane- et 9-aza-3-thiabicyclo[3.3.1]nonane, leur preparation et leur utilisation comme insecticides
WO1999026478A1 (fr) * 1997-11-21 1999-06-03 Zeneca Limited Amines bicycliques et leur utilisation comme insecticides
US5922732A (en) * 1995-05-24 1999-07-13 Zeneca Limited Bicyclic amines

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5922732A (en) * 1995-05-24 1999-07-13 Zeneca Limited Bicyclic amines
WO1998025924A1 (fr) * 1996-11-26 1998-06-18 Zeneca Limited Derives de 8-azabicyclo[3.2.1.]octane-, 8-azabicyclo[3.2.1]oct-6-ene-, 9-azabicyclo[3.3.1]nonane-, 9-aza-3-oxabicyclo[3.3.1]nonane- et 9-aza-3-thiabicyclo[3.3.1]nonane, leur preparation et leur utilisation comme insecticides
WO1999026478A1 (fr) * 1997-11-21 1999-06-03 Zeneca Limited Amines bicycliques et leur utilisation comme insecticides

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2378181A (en) * 2001-07-12 2003-02-05 Syngenta Ltd Insecticidal bicyclic amines
CN103570729A (zh) * 2012-07-26 2014-02-12 华东理工大学 环烯酮构建的二环新烟碱化合物及其制备方法和应用
WO2014154487A1 (fr) * 2013-03-28 2014-10-02 Syngenta Participations Ag Procédés de lutte contre des organismes nuisibles résistant aux néonicotinoïdes
WO2014154486A1 (fr) * 2013-03-28 2014-10-02 Syngenta Participations Ag Procédés de lutte contre des organismes nuisibles résistant aux néonicotinoïdes
WO2014154488A1 (fr) * 2013-03-28 2014-10-02 Syngenta Participations Ag Procédés de lutte contre des organismes nuisibles résistant aux néonicotinoïdes
CN105072910A (zh) * 2013-03-28 2015-11-18 先正达参股股份有限公司 控制新烟碱抗性有害生物的方法
CN105072911A (zh) * 2013-03-28 2015-11-18 先正达参股股份有限公司 控制新烟碱抗性有害生物的方法
CN105120667A (zh) * 2013-03-28 2015-12-02 先正达参股股份有限公司 控制新烟碱抗性有害生物的方法
US20160046620A1 (en) * 2013-03-28 2016-02-18 Syngenta Limited Methods of controlling neonicotinoid resistant pests
WO2015032617A1 (fr) * 2013-09-06 2015-03-12 Syngenta Participations Ag Composés insecticides

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AU2002219383A8 (en) 2008-01-03
AU2002219383A1 (en) 2002-07-30
WO2002057262A3 (fr) 2007-10-25

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