Classifications

• • 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
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
  • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01C—PLANTING; SOWING; FERTILISING
  • A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
  • A01C1/02—Germinating apparatus; Determining germination capacity of seeds or the like
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
  • A01G7/00—Botany in general
  • A01G7/06—Treatment of growing trees or plants, e.g. for preventing decay of wood, for tingeing flowers or wood, for prolonging the life of plants
• • 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
  • A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
• • 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
  • A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • 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

Definitions

• the present invention relates to a pest control composition and a pest control method.
• Non-Patent Document 1 discloses many compounds as active ingredients of pest control compositions.
• An object of the present invention is to provide a pest control composition having an excellent control effect against pests.
• Triflumezopyrim 2,4-dioxo-1- (5-pyrimidinylmethyl) ) -3- [3- (trifluoromethyl) phenyl] -2H-pyrido [1,2-a] pyrimidinium inner salt
• the present invention is as follows. Item 1.
• Item 1. Formula (1): [Where: A 1 represents —NR 7 —, an oxygen atom or a sulfur atom, A 2 represents ⁇ N—, ⁇ N ( ⁇ O) — or ⁇ CR 8 —, and Q represents ⁇ N— or ⁇ N ( ⁇ O).
• R 1 represents a C1-C6 alkyl group optionally having one or more atoms or groups selected from Group X, and R 2 , R 3 and R 4 are the same or different, A C1-C6 alkyl group optionally having one or more atoms or groups selected from the group: —OR 10 , —S (O) m R 10 , —S (O) 2 NR 10 R 11 , —NR 10 R 11 , —NR 10 CO 2 R 11 , —NR 10 C (O) R 11 , —CO 2 R 10 , —C (O) R 10 , —C (O) NR 10 R 11 , —SF 5 , cyano Group, nitro group, halogen atom or hydrogen atom, R 5 and R 6 are the same or different and selected from group X A C1-C6 alkyl group optionally having one or more atoms or groups, —OR 10 , —S (O) m R 10 , —S (O) 2
• Group X C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 cycloalkyl optionally having one or more halogen atoms or one or more C1-C3 alkyl groups A group consisting of a group, a cyano group, a hydroxy group and a halogen atom.
• Group W C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 cycloalkyl group optionally having one or more halogen atoms, hydroxy group, halogen atom and cyano group
• Item 2 Pest control composition containing triflumezopyrine
• a 1 is —NMe—, an oxygen atom or a sulfur atom
• a 2 is ⁇ N—, ⁇ N ( ⁇ O) — or ⁇ CH—
• R 1 has one or more halogen atoms.
• a C1-C6 alkyl group, R 2 and R 4 are hydrogen atoms
• R 3 is a C1-C3 alkyl group optionally having one or more halogen atoms or a hydrogen atom
• R 5 Is a C1-C3 alkyl group optionally having one or more halogen atoms, —OR 10 , or —S (O) m R 10
• R 6 is —NR 10 R 11 or a hydrogen atom, Item 2.
• Item 3. Item 3. The pest control composition according to Item 1 or 2, wherein A 1 is -NMe-.
• Item 3. The pest control composition according to Item 1 or 2, wherein A 1 is an oxygen atom.
• Item 5. A compound represented by the formula (1) and a 2,4-dioxo-1- (5-pyrimidinylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H-pyrido [1,2-a] pyrimidinium molecule Item 5.
• Item 6. A compound represented by the formula (1) and a 2,4-dioxo-1- (5-pyrimidinylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H-pyrido [1,2-a] pyrimidinium molecule
• a pest control method comprising a step of applying an effective amount of the pest control composition according to any one of Items 1 to 6 to a pest or a habitat of the pest.
• Item 8. Item 7.
• a method for controlling pests comprising a step of applying an effective amount of the pest control composition according to any one of Items 1 to 6 to a plant, plant seeds, bulbs, or soil in which plants are grown.
• Item 7. A plant seed or bulb to which an effective amount of the pesticidal composition according to any one of Items 1 to 6 is attached.
• pests can be controlled.
• the pest control composition of the present invention contains a compound represented by the above formula (1) (hereinafter sometimes referred to as the present compound) and triflumezopyrim.
• the notation of a Ca—Cb alkyl group in the present specification represents a linear or branched hydrocarbon group having a carbon number of a to b
• the notation of the Ca—Cb haloalkyl group represents a linear or branched hydrocarbon group having a carbon number of a to b in which one or more hydrogen atoms bonded to a carbon atom are substituted with a halogen atom, At this time, when having two or more halogen atoms, those halogen atoms may be the same or different from each other
• the notation of the Ca—Cb alkoxy group represents a linear or branched alkyl-O— group having a carbon number of a to b
• the notation of Ca—Cb cycloalkyl group represents a cyclic saturated hydrocarbon group having a to b carbon atoms.
• the expression “which may have one or more atoms or groups selected from group X” means that when it has two or more atoms or groups selected from group X, those The atoms or groups selected from group X may be the same as or different from each other.
• the expression “which may have one or more atoms or groups selected from group W” has two or more atoms or groups selected from group W. The atoms or groups selected from group W may be the same as or different from each other.
• the expression “may have one or more halogen atoms” means that when two or more halogen atoms are present, the halogen atoms may be the same as or different from each other. May be.
• halogen atom means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
• C1-C6 alkyl group optionally having one or more atoms or groups selected from group X refers to a hydrogen atom bonded to a carbon atom depending on an atom or group selected from group X.
• An optionally substituted linear or branched saturated hydrocarbon group having 1 to 6 carbon atoms, and having two or more atoms or groups selected from group X The atoms or groups selected from the group X may be the same as or different from each other.
• C1-C6 alkyl group optionally having one or more atoms or groups selected from group X include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec- Butyl, tert-butyl, pentyl, neopentyl, hexyl, methoxymethyl, ethoxymethyl, propyloxymethyl, isopropyloxymethyl, butyloxymethyl, sec-butyloxymethyl, tert- Butyloxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-propyloxyethyl group, 2-isopropyloxyethyl group, 2-butyloxyethyl group, 2-sec-butyloxyethyl group, 2-tert -Butyloxyethyl group, trifluoromethyl group, trichloromethyl group, 2-fluoro
• C1-C6 alkyl group optionally having one or more halogen atoms means that a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom and the number of carbon atoms is 1 to Represents a straight-chain or branched-chain hydrocarbon group consisting of six, and in this case, when having two or more halogen atoms, these halogen atoms may be the same or different from each other Good.
• C1-C6 alkyl group optionally having one or more halogen atoms examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.
• examples of the “C1-C6 alkyl group optionally having one or more atoms or groups selected from group W” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group.
• examples of the “C1-C6 alkoxy group optionally having one or more halogen atoms” include methoxy group, trifluoromethoxy group, ethoxy group, 2,2,2-trifluoroethoxy group, propyl group Examples thereof include an oxy group, isopropyloxy group, butyloxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group, pentyloxy group and hexyloxy group.
• examples of the “C3-C6 cycloalkyl group optionally having one or more halogen atoms” include a cyclopropyl group, a 2,2-difluorocyclopropyl group, a 2,2-dichlorocyclopropyl group, Examples include 2,2-dibromocyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group.
• examples of the “C3-C6 cycloalkyl group optionally having one or more halogen atoms or one or more C1-C3 alkyl groups” include a cyclopropyl group, a 1-methylcyclopropyl group, 2 -Methylcyclopropyl group, 1-fluorocyclopropyl group, 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group It is done.
• C1-C3 haloalkyl group refers to a linear or branched chain having 1 to 3 carbon atoms in which one or more hydrogen atoms bonded to carbon atoms are substituted with halogen atoms. Represents a hydrocarbon group, and when it has two or more halogen atoms, these halogen atoms may be the same as or different from each other.
• C1-C3 haloalkyl group examples include a fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, and trichloromethyl.
• examples of the “C1-C3 alkyl group” include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
• examples of the “C1-C3 perfluoroalkyl group” include a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a heptafluoroisopropyl group.
• Examples of the present compound include compounds represented by the formula (1) shown in the following [Table 1] to [Table 20].
• the present compound 70 The present compound 400 The present compound 401
• Me represents a methyl group
• Et represents an ethyl group
• Pr represents a propyl group
• Bu represents a butyl group
• tBu represents a tertiary butyl group
• iPr represents an isopropyl group
• CycPr represents a cyclopropyl group
• CycBu represents a cyclobutyl group.
• Production Example 1 (2) A mixture of 710 mg of compound (1-1) and 12 mL of DMF was cooled to ⁇ 60 ° C., and 10 g of trifluoroiodomethane was added. To this mixture, 1.2 mL of tetrakis (dimethylamino) ethylene was added dropwise at ⁇ 40 ° C. The temperature was raised to ⁇ 10 ° C., and the mixture was stirred at ⁇ 10 ° C. for 5 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure.
• Production Example 4 1.47 g of m-chloroperbenzoic acid (purity 65% or more) was added to a mixture of this compound 441 (1.06 g) and 30 ml of chloroform under ice cooling, and the mixture was stirred at room temperature for 6 hours. A 10% aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
• the obtained residue was subjected to silica gel column chromatography, and 0.87 g of 2- (3-ethylsulfonylpyridin-2-yl) -5- (trifluoromethylsulfanyl) benzoxazole (hereinafter referred to as the present compound 443) and 0.17 g of 2- (3-ethylsulfonylpyridin-2-yl) -5- (trifluoromethylsulfinyl) benzoxazole (hereinafter referred to as the present compound 444) was obtained.
• Triflumezopyrine used in the present invention is a mesoionic inner salt and is represented by six structural formulas as shown in the following formula (2A). Triflumezopyrine can be produced by a method described in International Publication No. 2012/092115. In this document, 2-hydroxy-4-oxo-1- (5-pyrimidinylmethyl) -3- [ It is described as 3- (trifluoromethyl) phenyl] -4H-pyrido [1,2-a] pyrimidinium inner salt.
• composition of the present invention examples include the following.
• a 1 is —NMe—, an oxygen atom or a sulfur atom
• a 2 is ⁇ N—, ⁇ N ( ⁇ O) — or ⁇ CH—
• R 1 is one or more halogen atoms
• R 2 and R 4 are hydrogen atoms
• R 3 is a C1-C3 alkyl group optionally having one or more halogen atoms or hydrogen
• R 5 is a C1-C3 alkyl group optionally having one or more halogen atoms, —OR 10 , or —S (O) m R 10
• R 6 is —NR 10 R 11
• a pest control composition comprising a compound which is a hydrogen atom and R 10 and R 11 are each independently a C1-C3 alkyl group optionally having one or more halogen atoms, and triflumezopyrine object.
• a 1 is —NMe— or an oxygen atom
• a 2 is ⁇ N—, ⁇ N ( ⁇ O) — or ⁇ CH—
• R 1 represents one or more halogen atoms.
• An optionally substituted C1-C6 alkyl group, R 2 and R 4 are hydrogen atoms
• R 3 is an optionally substituted C1-C3 alkyl group or hydrogen atom.
• R 5 is a C1-C3 alkyl group optionally having one or more halogen atoms, —OR 10 , or —S (O) m R 10
• R 6 is —NR 10 R 11 or hydrogen.
• a pest control composition comprising a compound which is an atom and each of R 10 and R 11 is independently a C1-C3 alkyl group optionally having one or more halogen atoms, and triflumezopyrine.
• a 1 is —NMe— or an oxygen atom
• a 2 is ⁇ N—, ⁇ N ( ⁇ O) — or ⁇ CH—
• R 1 is a C1-C6 alkyl group.
• R 2 , R 4 and R 6 are hydrogen atoms
• R 3 is a C1-C3 alkyl group optionally having one or more halogen atoms or a hydrogen atom
• R 5 is one or more halogen atoms.
• a C1-C3 alkyl group which may have an atom, —OR 10 , or —S (O) m R 10 , wherein R 10 may have one or more halogen atoms
• a pest control composition comprising a compound as a group and triflumezopyrine.
• a 1 is —NMe—
• a 2 is ⁇ N—, or ⁇ N ( ⁇ O) —
• R 1 is a C1-C6 alkyl group
• R 2 , R 4 and R 6 is a hydrogen atom
• R 3 is a C1-C3 alkyl group which may have one or more halogen atoms or a hydrogen atom
• R 5 may have one or more halogen atoms.
• a compound having a good C1-C3 alkyl group or —S (O) m R 10 wherein R 10 is a C1-C3 alkyl group optionally having one or more halogen atoms, and triflumezopyrine
• a 1 is an oxygen atom
• a 2 is ⁇ N—, ⁇ N ( ⁇ O) — or ⁇ CH—
• R 1 is a C1-C6 alkyl group
• R 2 , R 4 and R 6 are hydrogen atoms
• R 3 is a C1-C3 alkyl group which may have one or more halogen atoms or a hydrogen atom
• R 5 has one or more halogen atoms.
• a 1 is an oxygen atom
• a 2 is ⁇ N—, or ⁇ N ( ⁇ O) —
• R 1 may have one or more halogen atoms.
• a C6 alkyl group, R 2 , R 3 , R 4 and R 6 are hydrogen atoms
• R 5 may be a C1-C3 alkyl group optionally having one or more halogen atoms, or —S (O )
• a pest control composition comprising m R 10 and a compound in which R 10 is a C1-C3 alkyl group optionally having one or more halogen atoms, and triflumezopyrine.
• a 1 is an oxygen atom
• a 2 is ⁇ N—
• R 1 is a C1-C6 alkyl group
• R 2 , R 3 , R 4 and R 6 are hydrogen atoms.
• R 5 is a C1-C3 alkyl group which may have one or more halogen atoms, or —S (O) m R 10
• R 10 may have one or more halogen atoms.
• a pest control composition comprising a compound having a good C1-C3 alkyl group and triflumezopyrine.
• a 1 is an oxygen atom
• a 2 is ⁇ CH—
• R 1 is a C1-C6 alkyl group optionally having one or more halogen atoms
• R 2 , R 3 , R 4 and R 6 are a hydrogen atom
• R 5 is a C1-C3 alkyl group optionally having one or more halogen atoms, or —S (O) m R 10
• R 10 A pest control composition comprising a compound wherein C1 is a C1-C3 alkyl group optionally having one or more halogen atoms and trifluoromesopyrine.
• a 1 is an oxygen atom
• a 2 is ⁇ CH—
• R 1 is a C1-C6 alkyl group
• R 2 , R 3 , R 4 and R 6 are hydrogen atoms.
• R 5 is a C1-C3 alkyl group which may have one or more halogen atoms, or —S (O) m R 10
• R 10 may have one or more halogen atoms.
• a pest control composition comprising a compound having a good C1-C3 alkyl group and triflumezopyrine.
• R 1 may have one or more atoms or groups selected from group Y (group Y: may have one or more halogen atoms).
• group Y may have one or more halogen atoms).
• R 2 and R 4 are hydrogen atoms
• R 3 is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR 10 ) 3 , a halogen atom or a hydrogen atom
• R 5 may have one or more halogen atoms, a C1-C3 alkyl group, —OR 10 , —S (O) m R 10 , —CO 2 R 10 , —SF 5 or a halogen atom
• R 6 is —OR 10 , —NR 10 R 11 , —CO 2 R 10 , —C (O) NR 10 R 11 , —
• R 1 is a C1-C3 alkyl group which may have one or more halogen atoms
• R 2 and R 4 are hydrogen atoms
• R 3 is one or more halogen atoms.
• a C1-C3 alkyl group optionally having —, —C (OR 10 ) 3 , a halogen atom or a hydrogen atom
• R 5 being a C1-C3 alkyl group optionally having one or more halogen atoms
• R 6 is a cyano group, —NR 10 R 11 , a halogen atom or a hydrogen atom
• R 7 has one or more halogen atoms.
• R 8 is —S (O) m R 10 , a cyano group, a halogen atom or a hydrogen atom, and R 10 and R 11 are independently one or more halogen atoms.
• C1-C3 al optionally having an atom A compound which is a group, pesticidal composition containing the tri full meso pilin.
• R 1 is an ethyl group
• R 2 and R 4 are hydrogen atoms
• R 3 may be a C1-C3 alkyl group optionally having one or more halogen atoms, —C ( OR 10 ) 3 , a halogen atom or a hydrogen atom
• R 5 is a C1-C3 haloalkyl group, —OR 20 , —S (O) m R 20 or a halogen atom (R 20 represents a C1-C3 haloalkyl group)
• R 6 is a cyano group
• —NR 10 R 11 Are a halogen atom or a hydrogen atom
• R 7 is a C1-C6 alkyl group optionally having one or more halogen atoms
• R 8 is —S (O) m R 10 , a cyano group, a halogen atom Or a pest control composition comprising a compound which is a hydrogen atom
• a pest control composition comprising a compound of the formula (1) wherein A 1 is —NR 7 — and triflumezopyrine.
• a pest control composition comprising a compound wherein A 1 is an oxygen atom in formula (1) and triflumezopyrine.
• a 1 is —NR 7 —
• R 1 is a C1-C3 alkyl group
• R 2 and R 4 are hydrogen atoms
• R 3 has one or more halogen atoms.
• R 5 is a C1-C3 haloalkyl group
• R 6 is a cyano group, —NR 10 R 11 , a halogen atom or a hydrogen atom
• R 7 is a C1-C6 alkyl group optionally having one or more halogen atoms
• R 8 is -S (O) m R 10 , a cyano group, a halogen atom or a hydrogen atom
• R 10 and R 11 are each independently a C1-C3 alkyl
• a 1 is an oxygen atom
• R 1 is an ethyl group
• R 2 , R 4 and R 6 are hydrogen atoms
• R 3 has one or more halogen atoms.
• R 5 is a C1-C3 haloalkyl group, —OR 20 , —S (O) m R 20 or a halogen atom.
• R 8 is —S (O) m R 10 , a cyano group, a halogen atom or a hydrogen atom
• R 10 is a C1-C3 alkyl group optionally having one or more halogen atoms
• R 20 A pest control composition comprising a compound wherein is a C1-C3 haloalkyl group and triflumezopyrine.
• a 1 is an oxygen atom
• R 1 is an ethyl group
• R 2 , R 4, and R 6 are hydrogen atoms
• R 3 is a halogen atom or a hydrogen atom
• R 5 is A compound having a C1-C3 perfluoroalkyl group, —OR 30 or —S (O) m R 30
• R 30 is a C1-C3 perfluoroalkyl group
• R 8 is a halogen atom or a hydrogen atom
• the composition of the present invention may be a mixture of the present compound and triflumezopyrine, but usually, the present compound, triflumezopyrine and an inert carrier are mixed, and if necessary, a surfactant or other Addition of adjuvants for preparations and preparations formulated into oils, emulsions, flowables, wettable powders, granular wettable powders, powders, granules and the like are used.
• the formulated pest control composition can be used as it is or with other inactive ingredients added.
• the total amount of the present compound and triflumezopyrine in the composition of the present invention is usually in the range of 0.1% to 100% by weight, preferably 0.2 to 90% by weight, more preferably 1 to 80% by weight.
• Examples of the inert carrier used for formulation include a solid carrier and a liquid carrier.
• examples of such solid carriers include clays (kaolin clay, diatomite, bentonite, fusami clay, acid clay), synthetic hydrous silicon oxide, talc, ceramic, and other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, Hydrated silica, etc.), fine powders and granules of chemical fertilizers (ammonium sulfate, phosphorous, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate, etc.) Resin, nylon resin such as nylon-6, nylon-11, nylon-66, polyamide resin, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymer).
• liquid carriers examples include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic carbonization, and the like.
• alcohols methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.
• ketones acetone, methyl ethyl ketone, cyclohexanone, etc.
• aromatic carbonization and the like.
• Hydrogen toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.
• aliphatic hydrocarbons hexane, cyclohexane, kerosene, light oil, etc.
• esters ethyl acetate, butyl acetate, isopropyl myristate
• Ethyl oleate diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.
• nitriles acetonitrile, Butyronitrile, etc.
• ethers diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl
• Acid amides N, N-dimethylformamide, N, N-dimethylacetamide, etc.
• halogenated hydrocarbons diichloromethane, trichloroethane, carbon tetrachloride, etc.
• sulfoxides dimethylsulfoxide, etc.
• propylene carbonate and vegetable oil Soybean oil, cottonseed oil, etc.
• surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyethylene glycol fatty acid ester, and the like, and alkyl sulfonates, alkyl benzene sulfonates, alkyl sulfates, and the like.
• nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyethylene glycol fatty acid ester, and the like
• alkyl sulfonates alkyl benzene sulfonates, alkyl sulfates, and the like.
• An ionic surfactant is mentioned.
• formulation adjuvants include sticking agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), bentonite, synthetic water-soluble Polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4 -Methoxyphenol and 3-tert-butyl-4-methoxyphenol).
• sticking agents such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), bentonite, synthetic water-soluble Polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-
• the pest control method of the present invention is carried out by applying an effective amount of the composition of the present invention to pests or pest habitats (plants, soil, etc.).
• the pest control method of the present invention is usually used in the form of a pest control agent in which the composition of the present invention is formulated.
• the application method of the composition of the present invention includes, for example, application to plant stems and leaves, flower vases, seedlings or ears (plants), soil before planting or after planting (cultivate plants) Application to soil), seed disinfection, seed soaking, application to plant seeds such as seed coats or bulbs such as seed pods.
• this compound and triflumezopyrine may be applied separately, and seeds or bulbs to which either this compound or triflumezopyrine is attached are applied to plants, plant seeds, bulbs or soil where plants are grown. The remaining one may be applied before and after.
• foliage As application to the foliage, flower vase, seedling or ear (plant) of the plant, specifically, application methods applied to the surface of the plant such as foliage spray, trunk spray, etc., and before flowering, during flowering, Examples include a method of spraying the entire vase or the whole plant at the flowering time including after flowering, and a method of spraying the head or the whole plant at the heading time for cereals.
• the application method to the soil before planting or after planting is, for example, the composition of the present invention in the rhizosphere of a crop to be protected from damage such as feeding by pests. It is a method for directly controlling pests by applying a product, or a method for controlling pests that feed plants by osmotically transferring the composition of the present invention from the root or the like into the plant body.
• planting treatment planting hole spraying, planting hole treatment soil mixing
• plant source processing stock source spraying, strain source soil mixing, strain source irrigation, late seedling stage plant source processing
• planting groove processing planting groove processing
• cropping treatment growing sprinkling, cropping soil blending, growing season cropping spraying
• sowing cropping treatment sowing cropping spraying, sowing cropping soil blending
• Whole surface treatment overall soil spraying, whole surface soil mixing
• side strip treatment water surface treatment (water surface application, water surface application after flooding), other soil spraying treatment (growth season foliar leaf surface spraying, under the crown or around the trunk
• irrigation treatments irrigation, seedling irrigation, chemical solution injection treatment, local irrigation, chemical drip irrigation, chemical ligation
• Nursery box processing noursery box spraying, seedling box irrigation, seedling box
• the plant seed means the seed of the plant in a state before being sown in the soil or the culture medium
• the bulb is a bulb, a bulb of the plant in a state before being planted in the soil or the culture medium. It means tubers, rhizomes, stem fragments, seed pods and tuberous roots.
• the method of applying the composition of the present invention to plant seeds or bulbs is, for example, a method of controlling pests by directly applying to plant seeds or bulbs of crops to be protected from damage such as feeding by pests; A method for controlling pests that feed on seeds or the like by applying the composition of the present invention in the vicinity of seeds or bulbs; or by osmotically transferring the composition of the present invention from plant seeds or bulbs into the plant body
• the application amount can vary widely depending on the application time, application location, application method, etc., but in general, the present compound and triflumezopyrine
• the total amount of is usually 1 to 10,000 g per 10,000 m 2 .
• the composition of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc.
• the present compound and triflumezopyrine are usually adjusted so that the total concentration thereof is 0.01 to 10,000 ppm. It is diluted with water and applied, and granules, powders and the like are usually applied as they are.
• composition of the present invention when it is applied to rice, it may be used in a seedling box treatment.
• the time for treating the seedling box of the composition of the present invention may be from the time of sowing rice to the time of transplanting.
• the composition of the present invention may be used in direct seeding or transplantation cultivation of rice.
• the composition of the present invention when used for direct sowing cultivation rice, it may be applied before direct sowing, after direct sowing, before direct sowing or after direct sowing, and from before sowing to 21 days after sowing. Also good.
• the composition of the present invention when the composition of the present invention is used for transplanted rice, it may be rice after transplanting, and the time of application may be from before transplanting to 21 days after transplanting.
• the pests for which the composition of the present invention is effective include harmful arthropods such as harmful insects and harmful ticks, and specific examples of such pests include the following.
• Hemiptera small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), planthoppers such as Sejirounka (Sogatella furcifera), green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), tea Roh green leafhopper (Empoasca onukii) such as Leafhoppers, cotton aphids (Aphis gossypii), peach aphids (Myzus persicae), radish aphids (Brevicorine brassicae), aphid spiraecola, tulip beetle aphids Macrosiphum euphorbiae, potato beetle aphids (Aulacorthum solani), wheat beetle aphids (Rhopalosiphum aphids), citrus aphid
• Lepidoptera rice stem borer (Chilo suppressalis), Sankameiga (Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Japanese medusa such as Shibata toga (Pediasia teterrellus), Spodoptera litura, Spodoptera exigua, Ayuyotoga (Pseudaletia sepata), Atoga assicae), Agrotis ipsilon, Tamanaginawaba (Plusia nigrisigna), Trichopulsia, Heliotis, Helicoberpa, etc.
• Atsukiyamamushiga (Matsumuraeses azukivivora), Apple wolfberry (Adoxophyes orana fascita), Chanokokumonmonami (Adoxophyces honmai), Chamonamaki (Homomonakimaki) Upperus, Cyperpomonella, and other species, Caloptilia theivoria, Phyllonarycter lingoneis, etc.
• Species of the genus Kutis, Suga such as Plutella xylostella, Cotton worm (Pectinophora) gossypiella potatoes (Phythromea operculella) and other yellow moths, Hyphantoria cunea and other tigers, and iga (Tinea translucens).
• Thrips of the order Thrips thrips (Franklinella occidentalis), Thrips palmi, etc.
• Diptera insect fly (Delia platera), onion fly (Delia antiqua), etc. trifoliii), leafworms such as Chlamatomyia horticola, leafworms such as Chlorops oryzae, fruit fly of Dacus cucurbita
• Coleoptera pests Western Corn Rootworm (Diabrotica virgifera virgifera), corn rootworm such as southern corn rootworm (Diabrotica undecimpunctata howardi), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), chafers such as Japanese beetle (Popillia japonica) , Weevil (Sitophilus zeamais), Rice weevil (Lissohoptrus oryzophilus), Bone weevil (Echinocnemus squameus), Cotton weevil (Anthonomus grandis) nophorus venatus) weevils such as, Chai loco Meno mealworm (Tenebrio molitor), red flour beetle (Tribolium castaneum) Tenebrionidae such as, Inedorooimushi (Oulema oryzae), cucurbit leaf beetle (Aula
• the above-mentioned pests include populations that have acquired resistance to existing agents, and the composition of the present invention is also effective against such resistant populations.
• Agricultural crops corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, oilseed rape, sunflower, sugarcane, tobacco, etc.
• vegetables solanaceous vegetables (eggplants, tomatoes, peppers, peppers, Potato, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, squash, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables (Burdock, shungiku, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), sericaceae vegetables (carrot, parsley, celery, American burdock etc.), red crustacean vegetables (spinach, chard, etc.),
• Trees other than fruit trees Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, Tsuga, rat, pine, Spruce, yew) etc.
• the above-mentioned plant may be a plant bred by hybrid technology.
• a plant bred by hybrid technology is a plant having the characteristics of hybrid stress (generally resulting in increased yield potential, improved resistance to biological and abiotic stress factors, etc.).
• the above-mentioned plant may be a plant imparted with resistance by genetic recombination technology.
• the above-mentioned plants are resistant to HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors, glutamine synthase inhibitors, and herbicides such as bromoxynil and dicamba.
• HPPD inhibitors such as isoxaflutole
• ALS inhibitors such as imazetapyr and thifensulfuron methyl
• EPSP synthase inhibitors such as imazetapyr and thifensulfuron methyl
• EPSP synthase inhibitors such as glutamine synthase inhibitors
• herbicides such as bromoxynil and dicamba.
• plants that have been imparted by classical breeding methods or genetic engineering techniques are also included.
• the above-mentioned plants include plants that can synthesize, for example, selective toxins known in the genus Bacillus using genetic recombination technology.
• the above-mentioned plants are provided with two or more kinds of traits related to herbicide resistance, pest resistance, disease resistance, etc., as described above, using classical breeding techniques or genetic recombination techniques, and the like Alternatively, a line to which two or more kinds of properties possessed by the parent line are given by crossing genetically modified plants having different characteristics is also included. Examples of such plants include Smart stax (registered trademark).
• the content ratio of the present compound and triflumezopyrine is usually 100: 1 to 1: 100, preferably 10: 1 to 1:10, by weight.
• composition of the present invention may further contain one or more compounds selected from the following group (A).
• Examples of such a combination include the following. A combination of “any one of Compounds 1 to 481” with triflumezopyrine and isothianyl; A combination of “any one of the present compounds 1 to 481” with triflumezopyrine and orisatrobin; A combination of “any one of Compounds 1 to 481” with triflumezopyrine and probenazole; A combination of “any one of the present compounds 1 to 481” with triflumezopyrine and tricyclazole; A combination of “any one of the present compounds 1 to 481” with triflumezopyrine and diclosimet; A combination of “any one of the present compounds 1 to 481”, triflumezopyrine and carpropamide; A combination of “any one of the present compounds 1 to 481” with triflumezopyrine and thiazinyl; A combination of “any one of the present compounds 1 to 481” with triflumezopyrine and pyrokilone; A combination of “any one of the
• Formulation Example 1 5 parts of any one of the present compounds 1 to 481, 10 parts of triflumezopyrine, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water are mixed to give a total amount.
• Each of the preparations is obtained by finely pulverizing with 100 parts by a wet pulverization method.
• Formulation Example 2 Any one of the present compounds 1 to 481 was mixed with 10 parts of an aqueous solution containing 10 parts of triflumezopyrine, 1.5 parts of sorbitan trioleate, and 2 parts of polyvinyl alcohol, and pulverized by a wet pulverization method. Thereafter, an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto to make a total amount of 90 parts, and further 10 parts of propylene glycol is added and mixed by stirring to obtain each preparation.
• Formulation Example 3 By thoroughly pulverizing and mixing 10 parts of any one of the present compounds 1 to 481, 10 parts of triflumezopyrine, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and the remainder of the synthetic silicon hydroxide, 100 parts of wettable powder are obtained.
• Formulation Example 4 1 part of any one of the present compounds 1-481, 0.5 part of triflumezopyrine, 1 part of synthetic silicon hydrous powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and the remainder of kaolin clay are mixed. . Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated with a granulator, and dried by ventilation to obtain 100 parts of each granule.
• Formulation Example 5 2 parts of any one of the present compounds 1 to 481, 0.75 parts of triflumezopyrine, 2 parts of isotianil, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and the remainder of kaolin clay 100 parts of the mixture is pulverized and mixed well, water is added and kneaded well, and then granulated and dried to obtain 100 parts of granules.
• Formulation Examples 6-15 In Formulation Example 5, in place of 2 parts of isotianil, the same operations as in Formulation Example 5 are carried out except that the respective compounds and amounts used described in [Table A] are used to obtain respective granules.
• each treated seed was smeared on 200 kg of each preparation prepared according to Preparation Example 1 or 2 using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH) on 100 kg of dried sorghum seeds. Get.
• each treated seed can also be obtained by adding 180 grams of oxabetrinyl or 40 grams of floxophenim to 200 ml of each preparation and applying a smear treatment.
• Application example 3 Treated seeds are obtained by applying 50 g of each wettable powder prepared according to Formulation Example 3 to 10 kg of dried corn seeds.
• Application example 5 10 kg of dried soybean seeds were treated with 30 g of each wettable powder prepared according to Formulation Example 3 using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH). Get seeds.
• Each dried seed is treated with a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH) using 50 ml of each formulation prepared according to Formulation Example 1 or 2, and each treated seed is smeared. Get.
• Application example 7 By subjecting 10 kg of dried oilseed rape seeds to 150 kg of each of the preparations prepared according to Preparation Example 1 or 2, using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH) Get seeds.
• a rotary seed treatment machine seed dresser, manufactured by Hans-Ulrich Hege GmbH
• Test example 1 This compound 3, 15, 19, 20, 48, 50, 72, 81, 85, 99, 130, 421, 444, 445, 464, 467, and triflumezopyrine per mg, xylene: dimethylformamide: surfactant
• xylene dimethylformamide: surfactant
• a mixed solvent trade name: Solpol (registered trademark) 3005X, manufactured by Toho Chemical Co., Ltd.
• concentrations described in [Table 21] to [Table 22] Each test chemical solution was prepared by diluting with 0.02% by volume of a spreading agent (trade name: Cindyne (registered trademark), manufactured by Sumitomo Chemical Co., Ltd.).
• Cucumber (Cucumis sativus) cotyledon leaf pieces (1.5 cm in length) are housed in each well of a 24-well microplate (Becton Dickinson), 2 cotton aphids (Aphis gossypii) adults and 8 larvae per well was released and sprayed with 20 ⁇ L of the test drug solution per well. This was designated as a treatment zone.
• medical solution for a test was made into the no-treatment group.
• Control value (%) ⁇ 1 ⁇ (Tai) / (Cai) ⁇ ⁇ 100
• the character in a formula represents the following meaning.
• control value of triflumezopyrine and the present compound alone observed in a test conducted in accordance with the above-described test is 4 (concentration 0.1 ppm), 30 (concentration 1 ppm), and the present compound 15 Is 28 (concentration 1 ppm), the present compound 20 is 12 (concentration 0.01 ppm), the present compound 72 is 32 (concentration 10 ppm), the present compound 444 is 32 (concentration 1 ppm), and the present compound 445 is 30 (concentration 0.1 ppm) This compound 445 was 37 (concentration 1 ppm).
• pests can be controlled.

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• 2015
  • 2015-06-24 CN CN201580036296.5A patent/CN106572657B/zh active Active
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  • 2015-06-24 WO PCT/JP2015/068168 patent/WO2016002595A1/ja active Application Filing
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