WO1999059993A1 - Compose heterocyclique - Google Patents
Compose heterocyclique Download PDFInfo
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- WO1999059993A1 WO1999059993A1 PCT/JP1999/002515 JP9902515W WO9959993A1 WO 1999059993 A1 WO1999059993 A1 WO 1999059993A1 JP 9902515 W JP9902515 W JP 9902515W WO 9959993 A1 WO9959993 A1 WO 9959993A1
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 5
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 6
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- IIYVNMXPYWIJBL-UHFFFAOYSA-N 4-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=NC=C1 IIYVNMXPYWIJBL-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 55
- 239000004480 active ingredient Substances 0.000 abstract description 7
- QQZFLABCZMQVJP-UHFFFAOYSA-N 5-[4-(trifluoromethyl)pyridin-3-yl]-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=CC=NC=C1C1=NC=NO1 QQZFLABCZMQVJP-UHFFFAOYSA-N 0.000 abstract 1
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000365769 Thrips flavus Species 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 description 1
- 235000019399 azodicarbonamide Nutrition 0.000 description 1
- 229940092782 bentonite Drugs 0.000 description 1
- VJRITMATACIYAF-UHFFFAOYSA-N benzenesulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CC=C1 VJRITMATACIYAF-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 239000001390 capsicum minimum Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 229910001567 cementite Inorganic materials 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229940061632 dehydroacetic acid Drugs 0.000 description 1
- 235000019258 dehydroacetic acid Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- RGUOJYYIMVSCNC-UHFFFAOYSA-N n,n-dimethylformamide;2-methylpropanoic acid Chemical compound CN(C)C=O.CC(C)C(O)=O RGUOJYYIMVSCNC-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000024241 parasitism Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/82—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 five-membered rings with three ring hetero atoms
Definitions
- the present invention relates to a heterocyclic compound, a pesticide (Pesticide) containing the heterocyclic compound as an active ingredient, and a pest controlling method using the heterocyclic compound.
- Pesticide pesticide
- the compound of the present invention has the formula (II)
- the ring closure reaction is usually performed in a solvent, the reaction temperature is usually from 40 to 200 ° C, and the reaction time is usually from 1 to 30 hours.
- the solvent examples include protic polar solvents such as methanol, ethanol, and acetic acid, nitriles such as acetonitrile, aprotic polar solvents such as dioxane, and a mixed solvent thereof.
- the compound of the present invention represented by the formula (I) can be obtained by performing ordinary post-treatment operations such as neutralization, extraction with an organic solvent, and concentration.
- the compound can be further purified by recrystallization, column chromatography or the like, if necessary.
- the compound represented by the formula ( ⁇ ) has the formula ( ⁇ )
- the reaction is usually carried out in a solvent, and the reaction temperature is usually in the range of 120 to 30 ° C.
- the reaction time usually ranges from 0.2 to 5 hours.
- the solvent examples include protic polar solvents such as methanol, ethanol, acetic acid, and water; ethers such as tetrahydrofuran and dioxane; halogenated hydrocarbons such as methylene chloride and chloroform; nitriles such as acetonitrile; A mixed solvent is mentioned.
- protic polar solvents such as methanol, ethanol, acetic acid, and water
- ethers such as tetrahydrofuran and dioxane
- halogenated hydrocarbons such as methylene chloride and chloroform
- nitriles such as acetonitrile
- a mixed solvent is mentioned.
- the amount of the reagent used in the reaction is such that 1 mol of the compound represented by the formula ( ⁇ ) is 1 to 3 mol of the hydroxylamine or its hydrochloride.
- a base in an approximately equimolar amount to the hydrochloride.
- bases include, for example, tertiary amines such as trimethylamine, triethylamine and pyridine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium methoxide And alkali metal alkoxides such as sodium ethoxide.
- the compound represented by the formula (II) can be obtained by performing ordinary post-treatment operations such as neutralization, extraction with an organic solvent, and concentration.
- the compound can be further purified, if necessary, by recrystallization, column chromatography or the like.
- the compound can be produced by reacting a compound represented by the following formula:
- the reaction is usually carried out without a solvent or in a solvent, the reaction temperature is usually from 10 to 180 ° C, and the reaction time is usually from 1 to 30 hours.
- the solvent examples include ethers such as getyl ether, tetrahydrofuran, and dioxane; halogenated hydrocarbons such as methylene chloride and chloroform; aromatic hydrocarbons such as benzene and toluene; nitriles such as acetonitrile; And the like.
- ethers such as getyl ether, tetrahydrofuran, and dioxane
- halogenated hydrocarbons such as methylene chloride and chloroform
- aromatic hydrocarbons such as benzene and toluene
- nitriles such as acetonitrile
- the ratio of the reagents used in the reaction is such that the compound represented by the formula (V) is 1 to 3 mol per 1 mol of the compound represented by the formula (IV).
- the compound represented by the formula (III) can be obtained by performing ordinary post-treatment operations such as concentration.
- the compound can be further purified, if necessary, by recrystallization, column chromatography or the like.
- the compound represented by the formula (IV) is obtained by producing trifluoroacetoacetate from monoethyl malonate and trifluoroacetyl chloride (Org. Synth., 61, 5-8 (1982)). Then, it can be produced from the trifluoroacetoacetate ester and ⁇ -cyanoacetamide in four steps (J. Org. Chem., 25, 560-564 (1968) or J. Medicinal Chem., 10). , 149-154 (1967)).
- Examples of the pests to which the compound of the present invention can exhibit a controlling effect include the following harmful arthropods.
- Hemiptera Insects such as Brown-footed Deer (Laodelphax stnatellus), Brown-tailed Deer (Nilaparvata lugens), Singing Ground Beetle (Sogatella furcife), etc .; Aphis gossypii), aphids such as peach aphids, Myzus persicae, stink bugs, on-spot whitefly (T ialeurodes vaporariorum), evening whiteflies Bemisia tabaci), silver leaf whiteflies Bemisia argentifolli, whiteflies and others Gunbugs, lice, etc.
- Insects such as Brown-footed Deer (Laodelphax stnatellus), Brown-tailed Deer (Nilaparvata lugens), Singing Ground Beetle (Sogatella furcife), etc .
- Aphis gossypii) aphids
- Coleoptera pests Corn-related worms such as Western corn relay worms (Diabrotica virgifera virgifera) and Southern corn worms, Diabrotica undecimpunctata howardi, AnomaJa cuprea, and Anomala rufocuprea (Sitophilus zeamais), Rice Lentil Lssorhoptrus oryzophilus, Anole Fanolef (Hypera pastica), Azosomushi (Callosobruch uys Kunststoffensis), etc.
- Western corn relay worms Diabrotica virgifera virgifera
- Southern corn worms Diabrotica undecimpunctata howardi, AnomaJa cuprea, and Anomala rufocuprea (Sitophilus zeamais), Rice Lentil Lssorhoptrus oryzophilus, Anole Fanolef (Hypera pastica), Azosomushi (Callosobruch uys Kunststoffen
- Thistle pests Thrips palmiflora TTuips palmi), Negisama Thdps tabaci), H. thrips ⁇ ⁇ hawaiiensis, etc .;
- Hymenoptera pests scabies such as scabies, sparrows, stag bees, and the beetle Athe ia japonicd
- Orthopterous pests keratoids, bats, etc.
- Pteratophyte pests Wild flea Pulex irritans, etc.
- Termite pests Sphagnum termites Reticulitennes speratus), termites Coptotermes formosanus) Temple
- the compound of the present invention is also effective against the above harmful insects which are resistant to commercially available insecticides such as organophosphorus agents, carbamate agents and pyrethroid agents.
- insecticides such as organophosphorus agents, carbamate agents and pyrethroid agents.
- the compound of the present invention may be used as it is without adding any other components.
- compositions usually contain the compound of the present invention as an active ingredient in an amount of 0.01 to 95% by weight.
- solid carrier used in such formulation examples include clays (such as clay ore clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fubasami clay, acid clay), talc, ceramics, and other inorganic minerals (cericite). , Quartz, sulphate, activated carbon, calcium carbonate, hydrated silica, etc.) and fine powders or granules such as chemical fertilizers (ammonium sulphate, phosphorous ammonium, ammonium nitrate, urea, salt acetic acid, etc.).
- clays such as clay ore clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fubasami clay, acid clay), talc, ceramics, and other inorganic minerals (cericite).
- fine powders or granules such as chemical fertilizers (ammonium sulphate, phosphorous ammonium, ammonium n
- water For example, water, alcohols (methanol, ethanol, etc.), ketones (aceton, methyl ethyl ketone, etc.), hydrocarbons (benzene, toluene, xylene, ethylbenzene, methyl naphthylene, hexane, cyclohexane, kerosene, Light oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonit , Ethers (diisopropyl ether, dioxane, etc.), acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (E.g., dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethyl sulfoxide, vegetable oils such as soybean oil, cottonseed oil and the like.
- hydrocarbons
- gaseous carrier that is, the propellant, such as freon gas, butane gas, LPG (liquefied petroleum gas) ), Dimethyl ether, carbon dioxide and the like.
- the propellant such as freon gas, butane gas, LPG (liquefied petroleum gas)
- Dimethyl ether carbon dioxide and the like.
- surfactants include, for example, alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylenates, polyethylene glycol ethers, polyhydric alcohols Esters, sugar alcohol derivatives and the like.
- adjuvants for preparations such as fixatives and dispersants
- adjuvants for preparations include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, saccharides, synthetic water-soluble polymers ( Polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.).
- stabilizers include PAP (isopropyl acid phosphate) and BHT (2,6-di-tert-butyl-4-methylphenol).
- BHA a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol
- vegetable oils mineral oils, surfactants, fatty acids or esters thereof, and the like.
- self-combustion type smoke agents include nitrates, nitrites, guanidine salts, potassium chlorate, nitrocellulose, ethylcellulose, wood flour, etc., heating agents, alkali metal salts, alkaline earth metal salts, heavy chromium Thermal decomposition stimulants such as acid salts and chromates, oxygen supply agents such as nitric acid lime, flame retardants such as melamine and wheat starch, fillers such as diatomaceous earth, binders such as synthetic paste, etc.
- Examples of base materials for chemical reaction type smokers include exothermic agents such as sulfides, polysulfides, hydrosulfides, hydrated salts and calcium oxide of alkali metals, catalysts such as carbonaceous materials, iron carbide, and activated clay. Agents, azodicarbonamide, benzenesulfonylhydrazide, dinitrosopentamethylenetetramine, organic foaming materials such as polystyrene and polyurethane, and fillers such as natural fiber fragments and synthetic fiber fragments.
- bait baits include bait ingredients such as cereal flour, vegetable oil, sugar, and crystalline cellulose; antioxidants such as dibutylhydroxytoluene and nordihydroguairetic acid; preservatives such as dehydroacetic acid; and capsicum powder.
- bait ingredients such as cereal flour, vegetable oil, sugar, and crystalline cellulose
- antioxidants such as dibutylhydroxytoluene and nordihydroguairetic acid
- preservatives such as dehydroacetic acid
- capsicum powder examples include food inhibitors, cheese flavors, evening onion flavors, and attractants such as peanut oil.
- Formulations of flowables generally contain 1 to 75% of the compound of the present invention in 0.5 to 15% dispersant, 0.1 to 10% suspending aid.
- Agents eg, compounds that impart protective colloid thixotropy
- appropriate adjuvants eg, antifoaming agents, antioxidants, stabilizers, spreading agents, penetration aids
- Frozen Microbial dispersion in water containing an inhibitor, a fungicide, a fungicide, etc. instead of water, an oil in which the compound hardly dissolves can be used as a suspension in oil.
- the protective colloid for example, gelatin, casein, gums, cellulose ether, polyvinyl alcohol and the like are used.
- the compound imparting thixotropy include bentonite, aluminum magnesium silicate, xanthan gum, polyacrylic acid and the like.
- the preparation thus obtained is used as it is or diluted with water or the like.
- the compound of the present invention or a preparation thereof may be used in combination with other insecticides, nematicides, acaricides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil improvers, animal feeds, etc. It can also be used in combination with or without mixing.
- the application rate is usually in the range of 100 to 100 g, preferably 100 to 100 g per hectare. Range.
- the application concentration is usually 10 to 100 ppm, and granules, powders, etc. are applied as they are.
- these formulations may be sprayed on foliage of plants such as crops to be protected from pests. By treating these preparations with soil, pests living in the soil can be controlled, and pests in the foliage of plants such as crops can be controlled at the same time.
- emulsions, wettable powders, flowables, etc. are usually diluted with water to 0.01 to 100 ppm and applied. Aerosols, smokers, ULVs, poison baits, etc. should be applied as they are.
- Dioxane was distilled off under reduced pressure, 10 ml of water was added to the residue, and then potassium carbonate powder was added under cooling with an ice-water bath to adjust the pH to pH8 to pH7. This was extracted twice with ethyl acetate, and the organic layer was washed with 10% saline and dried over magnesium sulfate. After magnesium sulfate is filtered off, the solvent is distilled off under reduced pressure. After that, 0.357 g (yield: 80.2%) of N 2 -hydroxy-1-N 1- (4-trifluoromethylviridine-13-force ruponyl) formamidine was obtained.
- N 2 -Hydroxy-1-N 1- (4-trifluoromethylviridine-13-carbonyl) formamidine was suspended in 15 ml of dioxane at room temperature, and 15 ml of acetic acid was added dropwise. This mixed solution was heated and stirred at 100 ° C. for about 4 hours. Dioxane was distilled off under reduced pressure, 50 ml of water was added to the residue, and then carbonated lithium powder was added under ice-water bath cooling to adjust the solution to pH 7-8.
- 1 part of the compound of the present invention is dissolved in an appropriate amount of acetone, and 5 parts of synthetic hydrous silicon oxide fine powder, 0.3 part of PAP and 93.7 parts of clay are added thereto, followed by stirring and mixing with a juice mixer. Then, the acetone is removed by evaporation to obtain 1% powder.
- 10 parts of the compound of the present invention is added to 40 parts of an aqueous solution containing 6 parts of polyvinyl alcohol, and dispersed by stirring with a mixer. To this was added 40 parts of an aqueous solution containing 0.5 part of xanthangum and 0.1 part of aluminum magnesium silicate, and 10 parts of propylene glycol was added, followed by gentle stirring and mixing. Get a% flowable.
- 0.1 part of the compound of the present invention is dissolved in 5 parts of xylene and 5 parts of trichloride and mixed with 89.9 parts of deodorized kerosene to obtain a 0.1% oil solution.
- a valve part attach a valve part, and 40 parts of propellant (liquefied petroleum gas) under pressure to obtain aqueous aerosol
- Test example 1 Insecticidal test against aphid (Foliage spray test)
- the emulsion of the test compound obtained according to Formulation Example 1 was diluted with water so that the active ingredient concentration became 500 ppm.
- the first true leaf of a cucumber planted in a polyethylene cup with the first true leaf unfolded was inoculated with 20 Aphid aphids.
- the diluent was applied at a rate of 20 ml / cup to the cucumber planted with the aphid parasitism.
- the compound of the present invention exhibited a control value of 90% or more.
- Test Example 2 Insecticidal test against aphid
- the emulsion of the test compound obtained according to Formulation Example 1 was diluted with water so that the active ingredient concentration became 500 ppm.
- the diluted solution was irrigated at a rate of 5 ml / l pot to a root of a lily plant planted in a polyethylene cup.
- Five days after drug treatment, 20 aphids were released on the true leaves, and 7 days after release, the control value was determined by the same formula as used in Test Example 1.
- the compound of the present invention exhibited a control value of 90% or more.
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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)
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Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU37306/99A AU3730699A (en) | 1998-05-18 | 1999-05-13 | Heterocyclic compound |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP13547498 | 1998-05-18 | ||
JP10/135474 | 1998-05-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999059993A1 true WO1999059993A1 (fr) | 1999-11-25 |
Family
ID=15152569
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1999/002515 WO1999059993A1 (fr) | 1998-05-18 | 1999-05-13 | Compose heterocyclique |
Country Status (2)
Country | Link |
---|---|
AU (1) | AU3730699A (fr) |
WO (1) | WO1999059993A1 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000035285A1 (fr) * | 1998-12-17 | 2000-06-22 | Aventis Cropscience Gmbh | 4-haloalkyl-3-heterocyclylpyridines et 4-haloalkyl-5-heterocyclylpyrimidines et leur utilisation comme repulsifs |
WO2001014373A1 (fr) * | 1999-08-20 | 2001-03-01 | Syngenta Participations Ag | Derives de trifluoromethylpyri(mi)dine |
WO2002048111A3 (fr) * | 2000-12-13 | 2003-03-27 | Bayer Cropscience Gmbh | Procede de fabrication de 4-haloalkyl-nicotine-nitriles |
US8017632B2 (en) | 2004-07-20 | 2011-09-13 | Bayer Cropscience Ag | Selective insecticides based on haloalkylnicotinic acid derivatives, anthranilic acid diamides, or phthalic acid diamides and safeners |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998057969A1 (fr) * | 1997-06-16 | 1998-12-23 | Hoechst Schering Agrevo Gmbh | 4-haloalkyl-3- heterocyclylpyridines et 4-haloalkyl -5-heterocyclylpyrimidines, leurs procedes de preparation, produits les contenant et leur utilisation comme pesticides |
-
1999
- 1999-05-13 WO PCT/JP1999/002515 patent/WO1999059993A1/fr active Application Filing
- 1999-05-13 AU AU37306/99A patent/AU3730699A/en not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998057969A1 (fr) * | 1997-06-16 | 1998-12-23 | Hoechst Schering Agrevo Gmbh | 4-haloalkyl-3- heterocyclylpyridines et 4-haloalkyl -5-heterocyclylpyrimidines, leurs procedes de preparation, produits les contenant et leur utilisation comme pesticides |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000035285A1 (fr) * | 1998-12-17 | 2000-06-22 | Aventis Cropscience Gmbh | 4-haloalkyl-3-heterocyclylpyridines et 4-haloalkyl-5-heterocyclylpyrimidines et leur utilisation comme repulsifs |
WO2001014373A1 (fr) * | 1999-08-20 | 2001-03-01 | Syngenta Participations Ag | Derives de trifluoromethylpyri(mi)dine |
WO2002048111A3 (fr) * | 2000-12-13 | 2003-03-27 | Bayer Cropscience Gmbh | Procede de fabrication de 4-haloalkyl-nicotine-nitriles |
US6864385B2 (en) | 2000-12-13 | 2005-03-08 | Aventis Cropscience Gmbh | Process for the preparation of 4-haloalkylnicotinonitriles |
KR100845376B1 (ko) * | 2000-12-13 | 2008-07-09 | 바이엘 크롭사이언스 게엠베하 | 4-할로알킬 니코틴 니트릴의 제조 방법 |
US8017632B2 (en) | 2004-07-20 | 2011-09-13 | Bayer Cropscience Ag | Selective insecticides based on haloalkylnicotinic acid derivatives, anthranilic acid diamides, or phthalic acid diamides and safeners |
US8685985B2 (en) | 2004-07-20 | 2014-04-01 | Bayer Cropscience Ag | Selective insecticides based on anthranilic acid diamides and safeners |
US8841328B2 (en) | 2004-07-20 | 2014-09-23 | Bayer Cropscience Ag | Selective insecticides based on anthranilic acid diamides and safeners |
Also Published As
Publication number | Publication date |
---|---|
AU3730699A (en) | 1999-12-06 |
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