WO2013191114A1 - 有害節足動物防除組成物及び有害節足動物の防除方法 - Google Patents
有害節足動物防除組成物及び有害節足動物の防除方法 Download PDFInfo
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- WO2013191114A1 WO2013191114A1 PCT/JP2013/066530 JP2013066530W WO2013191114A1 WO 2013191114 A1 WO2013191114 A1 WO 2013191114A1 JP 2013066530 W JP2013066530 W JP 2013066530W WO 2013191114 A1 WO2013191114 A1 WO 2013191114A1
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- 0 C*(*)Cc(cc1)ccc1C(C(N(C=C*1)C1=[N+]1C*)=O)=C1[O-] Chemical compound C*(*)Cc(cc1)ccc1C(C(N(C=C*1)C1=[N+]1C*)=O)=C1[O-] 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—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
- A01N43/80—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 1,2
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/10—Insect repellent
Definitions
- the present invention relates to a harmful arthropod control composition and a method for controlling harmful arthropods.
- Patent Document 1 Patent Document 1
- Patent Document 2 Patent Document 2
- Non-Patent Document 1 compounds are known as active ingredients of harmful arthropod control compositions.
- An object of the present invention is to provide a harmful arthropod control composition having an excellent control effect on harmful arthropods.
- the present inventor has shown a compound represented by the following formula (I) and a formula (II) below. It has been found that a composition containing a compound and one or more compounds selected from the following group (A) has an excellent controlling effect on harmful arthropods. That is, the present invention is as follows [1] to [9].
- R 2 is any group represented by the following formulas (R 2a ), (R 2b ), (R 2c ), (R 2d ) and (R 2e ). ⁇ Where, R 3a , R 3b and R 3c are the same or different and are each a C1-C4 alkyl group optionally having one or more halogen atoms, and a C2-C4 alkynyl optionally having one or more halogen atoms.
- R 3d is a C1-C4 alkyl group that may have one or more halogen atoms, a C1-C4 alkoxy group that may have one or more halogen atoms, a cyano group, a nitro group, or a halogen atom.
- X a , X b , X c and X d are the same or different and represent 0, 1 or 2;
- Z b and Z c are the same or different and each represents an oxygen atom, a sulfur atom or a group represented by the formula NR 7 ;
- R 7 represents a C1-C4 alkyl group which may have one or more halogen atoms or a hydrogen atom.
- R 3a , R 3b , R 3c, and R 3d that is, when X a , X b , X c, and X d are 2), each R 3a , R 3b , R 3c And R 3d may be the same or different.
- R 5 represents a hydrogen atom or a fluorine atom
- R 6 represents a hydrogen atom, a fluorine atom, a difluoromethyl group or a trifluoromethyl group.
- n 2 or 3
- a plurality of R 1 may be different from each other.
- a compound of formula (II) [Wherein, A 1 represents a methyl group, and A 2 represents a chlorine atom or a cyano group.
- a composition for controlling harmful arthropods comprising a compound represented by formula (A) and one or more compounds selected from the group (A);
- R 2 is any group represented by the following formulas (R 2a ), (R 2b ), (R 2c ) and (R 2d ) [Where: R 3a , R 3b and R 3c are the same or different and are each a C1-C4 alkyl group optionally having one or more halogen atoms, and a C2-C4 alkynyl optionally having one or more halogen atoms.
- R 3d is a C1-C4 alkyl group that may have one or more halogen atoms, a C1-C4 alkoxy group that may have one or more halogen atoms, a cyano group, a nitro group, or a halogen atom.
- X a , X b , X c and X d are the same or different and represent 0, 1 or 2;
- Z b and Z c are the same or different and each represents an oxygen atom, a sulfur atom or a group represented by the formula NR 7 ;
- R 7 represents a C1-C4 alkyl group which may have one or more halogen atoms or a hydrogen atom.
- R 3a , R 3b , R 3c, and R 3d that is, when X a , X b , X c, and X d are 2), each R 3a , R 3b , R 3c And R 3d may be the same or different.
- a method for controlling harmful arthropods comprising a step of applying an effective amount of the composition for controlling harmful arthropods according to any one of [1] to [4] to a plant or a plant cultivation site.
- [6] The method for controlling harmful arthropods according to [5], wherein the step of applying to a plant or a plant cultivation site is a step of applying to rice or a rice cultivation site.
- harmful arthropods can be controlled.
- the harmful arthropod control composition of the present invention comprises a compound represented by the above formula (I) (hereinafter sometimes referred to as the present mesoionic compound) and a compound represented by the above formula (II) (hereinafter referred to as the present anthranil).
- An amide compound) and one or more compounds selected from the group (A) hereinafter may be referred to as the present compound A).
- each of the substituents represented by R 1 , R 2a , R 2b , R 2c , R 2d , R 2e , R 3a , R 3b , R 3c , R 3d and R 7 is as follows: Things.
- the C1-C4 alkyl group means a linear or branched alkyl group having 1 to 4 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, and a 1-methyl group. Examples include an ethyl group, a butyl group, a 1-methylpropyl group, a 2-methylpropyl group, and a 1,1-dimethylethyl group.
- a C2-C4 alkenyl group is a linear or branched chain composed of 2 to 4 carbon atoms and has one or more double bonds in the molecule.
- Means a hydrogen group for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 2-methyl-2-propenyl group Is mentioned.
- the C2-C4 alkynyl group is an unsaturated hydrocarbon having a linear or branched chain composed of 2 to 4 carbon atoms and having one or more triple bonds in the molecule.
- Means a group, and examples thereof include an ethynyl group, a 2-propynyl group, a 2-butynyl group, and a 3-butynyl group.
- the C1-C4 alkoxy group means a group represented by a linear or branched alkyl-O— having 1 to 4 carbon atoms, such as a methoxy group, an ethoxy group, Examples include propoxy group, 1-methylethoxy group, butoxy group, 1-methylpropoxy group, 2-methylpropoxy group and 1,1-dimethylethoxy group.
- halogen atoms means that when two or more halogen atoms are present, the halogen atoms may be the same or different from each other. Also good.
- one or more means one or more and the maximum number of atoms or groups to which atoms or groups can be bonded, unless otherwise specified.
- Examples of the halogen atom represented by R 1 , R 3a , R 3b , R 3c and R 3d include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
- Examples of the C1-C4 alkyl group optionally having one or more halogen atoms represented by R 1 , R 3a , R 3b , R 3c , R 3d and R 7 include a methyl group and trifluoromethyl.
- Examples of the C2-C4 alkenyl group represented by R 1 which may have one or more halogen atoms include a 2-propenyl group, a 3-chloro-2-propenyl group, and 2-chloro-2-propenyl. Groups, 3,3-dichloro-2-propenyl group, 2-butenyl group, 3-butenyl group and 2-methyl-2-propenyl group.
- Examples of the C2-C4 alkynyl group represented by R 1 , R 3a , R 3b and R 3c which may have one or more halogen atoms include a 2-propynyl group and 3-chloro-2-propynyl. Group, 3-bromo-2-propynyl group, 2-butynyl group and 3-butynyl group.
- Examples of the C1-C4 alkoxy group optionally having one or more halogen atoms represented by R 1 , R 3a , R 3b , R 3c and R 3d include a methoxy group, a trifluoromethoxy group, and ethoxy Group, 2,2,2-trifluoroethoxy group, propoxy group, 1-methylethoxy group, butoxy group, 2-methylpropoxy group, 1-methylpropoxy group and 1,1-dimethylethoxy group.
- R 2a examples include 6-fluoro-3-pyridyl group, 6-chloro-3-pyridyl group, 6-bromo-3-pyridyl group, 6-methyl-3-pyridyl group, and 6-cyano-3-pyridyl group.
- R 2b examples include 2-fluoro-5-thiazolyl group, 2-chloro-5-thiazolyl group, 2-bromo-5-thiazolyl group, 2-methyl-5-thiazolyl group, 5-thiazolyl group, 2- Examples include fluoro-5-oxazolyl group, 2-chloro-5-oxazolyl group, 5-oxazolyl group, 2-chloro-1-methyl-5-imidazolyl group and 2-fluoro-1-methyl-5-imidazolyl group.
- R 2c examples include a 1-methyl-4-pyrazolyl group and a 3-methyl-5-isoxazolyl group.
- R 2d examples include a tetrahydrofuran-2-yl group and a tetrahydrofuran-3-yl group.
- R 2e examples include a 5-pyrimidinyl group.
- n 2 is the same as or different from each other, and is a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, a trifluoromethyl group or a trifluoromethoxy group, and R A compound in which 2 is a 2-chloro-5-thiazolyl group, a 6-chloro-3-pyridyl group or a 5-pyrimidinyl group, and Q is CH ⁇ CH or a sulfur atom;
- n is 1, R 1 is a fluorine atom, chlorine atom, bromine atom, methyl group, methoxy group, trifluoromethyl group or trifluoromethoxy group, and R 2 is 2-chloro-5.
- n 2
- R 1 is the same as or different from each other, and is a fluorine atom, a trifluoromethyl group or a trifluoromethoxy group
- R 2 is a 2-chloro-5-thiazolyl group
- 6 A compound which is a chloro-3-pyridyl group or a 5-pyrimidinyl group and Q is CH ⁇ CH or a sulfur atom
- n 1, R 1 is a fluorine atom, a trifluoromethyl group or a trifluoromethoxy group
- R 2 is a 2-chloro-5-thiazolyl group or a 6-chloro-3-pyridyl group.
- n 2 is the same as or different from each other, and is a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, a trifluoromethyl group or a trifluoromethoxy group, and R A compound in which 2 is a 2-chloro-5-thiazolyl group or a 6-chloro-3-pyridyl group and Q is CH ⁇ CH or a sulfur atom;
- n is 1, R 1 is a fluorine atom, chlorine atom, bromine atom, methyl group, methoxy group, trifluoromethyl group or trifluoromethoxy group, and R 2 is 2-chloro-5.
- a compound which is a thiazolyl group or a 6-chloro-3-pyridyl group and Q is CH ⁇ CH or a sulfur atom;
- n 2
- R 1 is the same as or different from each other, and is a fluorine atom, a trifluoromethyl group or a trifluoromethoxy group
- R 2 is a 2-chloro-5-thiazolyl group or 6
- a compound which is a chloro-3-pyridyl group and Q is CH ⁇ CH or a sulfur atom
- n is 1, R 1 is a fluorine atom, a trifluoromethyl group or a trifluoromethoxy group, and R 2 is a 2-chloro-5-thiazolyl group or a 6-chloro-3-pyridyl group.
- n 2, R 1 is the same as or different from each other, and is a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, a trifluoromethyl group or a trifluoromethoxy group, and R A compound wherein 2 is a 2-chloro-5-thiazolyl group, a 6-chloro-3-pyridyl group
- n 2
- R 1 is the same as or different from each other, and is a fluorine atom, a trifluoromethyl group or a trifluoromethoxy group
- R 2 is a 2-chloro-5-thiazolyl group
- 6 A compound which is a chloro-3-pyridyl group or a 5-pyrimidinyl group and Q is CH ⁇ CH
- n is 1, R 1 is a fluorine atom, a trifluoromethyl group or a trifluoromethoxy group, and R 2 is a 2-chloro-5-thiazolyl group or a 6-chloro-3-pyridyl group.
- n 1, R 1 is a fluorine atom or a trifluoromethyl group, R 2 is a 2-chloro-5-thiazolyl group or a 5-pyrimidinyl group, and Q is CH ⁇ CH.
- R 1 is the same as or different from each other, and is a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, a trifluoromethyl group or a trifluoromethoxy group, and R A compound wherein 2 is a 5-pyrimidinyl group and Q is CH ⁇ CH;
- n is 1, R 1 is a fluorine atom, chlorine atom, bromine atom, methyl group, methoxy group, trifluoromethyl group or trifluoromethoxy group, and R 2 is a 5-pyrimidinyl group.
- a compound wherein Q is CH ⁇ CH;
- n 2
- R 1 is the same as or different from each other, is a fluorine atom, a trifluoromethyl group or a trifluoromethoxy group, R 2 is a 5-pyrimidinyl group, and Q is CH
- a compound wherein n 1, R 1 is a fluorine atom, a trifluoromethyl group or a trifluoromethoxy group, R 2 is a 5-pyrimidinyl group, and Q is CH ⁇ CH;
- n is 1, and R 1 is a C1-C4 alkyl group which may have one or more halogen atoms, and C1-C4 which may have one or more halogen atoms.
- R 2 is a pyridyl group having one halogen atom, a thiazolyl group having one halogen atom, or a pyrimidyl group, and Q is CH ⁇ CH or a sulfur atom.
- the present mesoionic compound also includes ionization embodiments represented by other structural formulas, and any of these embodiments is present alone or in admixture of two or more.
- the present mesoionic compounds include these.
- the present mesoionic compound can be produced by the methods described in International Publication No. 2009/099929 and International Publication No. 2012/092115.
- anthranilamide compound (1) a compound in which A 1 is a methyl group and A 2 is a chlorine atom in the formula (II) (hereinafter referred to as the present anthranilamide compound (1)) is, for example, “The Pesticide Manual. -15th edition (published by BCPC); ISBN 978-1-901396-18-8 ”, page 175, and the compound can be obtained from a commercially available formulation or obtained by a known method.
- a compound in which A 1 is a methyl group and A 2 is a cyano group in the formula (II) (hereinafter referred to as the present anthranilamide compound (2)) is, for example, “The Pesticide Manual. -15th edition (BCPC); ISBN 978-1-901396-18-8 ”, page 251, and the compound can be produced by the method described in International Publication No. 2004/067528.
- probenazole, thiazinyl, tricyclazole, oryastrobine and pyroxylone used in the present invention are all known compounds, such as “The Pesticide Manual-15th edition (published by BCPC); ISBN 978-1-901396-18-8”. 927, 1134, 1163, 840 and 999. These compounds can be obtained from commercially available preparations or produced by known methods. Isotianil used in the present invention is a known compound and can be produced, for example, by the method described in International Publication No. 99/024413.
- the content ratio of the mesoionic compound and the anthranilamide compound used in the present invention is not particularly limited, but the weight ratio of the mesoionic compound to the anthranilamide compound is Usually, it is 50: 1 to 1:50, preferably 10: 1 to 1:10, more preferably 5: 1 to 1: 5, and particularly preferably 4: 1 to 1: 1.5.
- the content ratio of the present mesoionic compound and the present compound A used in the present invention in the harmful arthropod control composition of the present invention is not particularly limited, but the weight ratio of the present mesoionic compound to the present compound A is usually 10. : 1 to 1: 100, preferably 10: 1 to 1:50, more preferably 5: 1 to 1:50, and particularly preferably 1.5: 1 to 1:48.
- the harmful arthropod control composition of the present invention can contain other agrochemical active ingredients together with the mesoionic compound, the anthranilamide compound and the compound A.
- Such other agrochemical active ingredients include, for example, furametopil.
- Furametopil is described, for example, on page 580 of “The Pesticide Manual-15th edition (BCPC); ISBN 978-1-901396-18-8” and is obtained from a commercially available compound or manufactured by a known method. Is obtained.
- the harmful arthropod control composition of the present invention contains furametopil, the content ratio is not particularly limited, but the weight ratio of the mesoionic compound to furametopil is usually 10: 1 to 1:50, preferably 10: 1 to 1:20.
- the harmful arthropod control composition of the present invention may be a mixture of the mesoionic compound, the anthranilamide compound and the compound A, but usually the mesoionic compound, the anthranilamide compound and the present compound A Mix with an inert carrier and add surfactants and other formulation adjuvants as necessary to prepare oils, emulsions, flowables, wettable powders, granulated wettable powders, powders, granules, etc. Is used.
- the above-mentioned formulated harmful arthropod control composition can be used as a harmful arthropod control agent as it is or by adding other inactive components (water, sand, vegetable oil, etc.).
- the total amount of the mesoionic compound, the anthranilamide compound and the compound A in the harmful arthropod control composition of the present invention is usually 0.01 to 100% by weight, preferably 0.1 to 90% by weight, more preferably. Is 0.5 to 70% by weight.
- Examples of the inert carrier used for formulation include a solid carrier and a liquid carrier.
- the solid carrier include minerals such as kaolin clay, attapulgite clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, natural organic substances such as corn cob powder and walnut shell powder, urea
- Examples include synthetic organic materials such as calcium carbonate, ammonium sulfate, and the like, fine powders or granular materials made of synthetic inorganic materials such as synthetic silicon hydroxide, and liquid carriers include aromatic carbonization such as xylene, alkylbenzene, and methylnaphthalene.
- Alcohols such as 2-propanol, ethylene glycol, propylene glycol and ethylene glycol monoethyl ether, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, petroleum aliphatic hydrocarbons and esters kind Sulfoxide, acetonitrile, and water.
- surfactants include anionic interfaces such as alkyl sulfate esters, alkylaryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate esters, lignin sulfonates, naphthalene sulfonate formaldehyde polycondensates, and the like.
- Nonionic surfactants such as activators and polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters, and cationic surfactants such as alkyltrimethylammonium salts.
- adjuvants for preparation examples include water-soluble polymers such as polyvinyl alcohol and polyvinylpyrrolidone, gum arabic, alginic acid and salts thereof, polysaccharides such as CMC (carboxymethylcellulose) and xanthan gum, inorganic substances such as aluminum magnesium silicate and alumina sol. , Stabilizers such as preservatives, colorants and PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol).
- water-soluble polymers such as polyvinyl alcohol and polyvinylpyrrolidone, gum arabic, alginic acid and salts thereof, polysaccharides such as CMC (carboxymethylcellulose) and xanthan gum, inorganic substances such as aluminum magnesium silicate and alumina sol.
- Stabilizers such as preservatives, colorants and PAP (isopropyl acid phosphate), BHT (2,6-di-tert-buty
- the harmful arthropod control composition of the present invention can be used to protect plants from injuries such as feeding and sucking by harmful arthropods.
- Examples of the harmful arthropods having the control effect of the harmful arthropod control composition of the present invention include the following.
- Hemiptera small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), planthopper such Sejirounka (Sogatella furcifera), green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), Inazuma leafhopper (Recilia dorsalis), Chanomidorihime Leafhoppers such as leafhopper (Empoasca onukii), cotton aphid (Aphis gossypi), peach aphid (Myzus persicae), radish aphid (Brevicorine brassicae), snowy spruce (Aphasianis spruce) la), tulip beetle aphids (Macrosiphum euporbiae), potato beetle aphids (Aulacorthum solai), wheat beetle aphi
- Lepidoptera rice stem borer (Chilo suppressalis), Sankameiga (Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarchaderogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Shibatsutoga Japanese medusa such as (Pediasia teterrulus), Spodoptera litura, Spodoptera exigua, Pseudoteria septata, Seiyoi ferens), mushroom brassicae, agrotis ipsilon, tamanagiwawa (plusia nigrisigna), cervus genus, trichoplusia ni White butterflies, genus Adoxofies, papaver moth (Graphophrita molesta), leguminivola glycinivolorella,
- Diptera onion maggot (Hylemya antiqua), seedcorn maggot (Hylemya platura), rice leafminer (Agromyza oryzae), rice Hime leafminer (Hydrellia griseola), Inekimoguribae (Chlorops oryzae), leafminer such as beans leafminer (Liriomyza trifolii), melon fly (Dacus cucurbitae), Ceratotis capitata and the like; Coleoptera: beetle, Epilachna vigintioctopunctata (Epilachna vigintioctopunctata), cucurbit leaf beetle (Aulacophora femoralis), Kisujinomihamushi (Phyllotreta striolata), Inedorooimushi (Oulema oryzae), rice weevil (Echinocnemus squameus), rice water weevil (L
- planthoppers include planthoppers, leafhoppers, aphids, stink bugs, rice weevil, rice beetles, moths, and moths.
- planthoppers are particularly preferable, and examples of planthoppers include brown planthopper (Nilaparvata lugens), white-spotted planthopper (Sogataella furcifera), and brown planthopper (Laodedelfax striatellus).
- the harmful arthropod control composition of the present invention can also control plant diseases such as rice blast (Magnaporthe grisea).
- the harmful arthropod control composition of the present invention is applied to cultivated lands such as fields, paddy fields, dry fields, lawns, orchards, or non-cultivated lands. Moreover, the harmful arthropod control composition of the present invention can control harmful arthropods in the cultivated land in the cultivated land or the like where the “plant” or the like is cultivated.
- plants for which the harmful arthropod control composition of the present invention can be used include the following.
- Agricultural crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
- Vegetables Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, rape, etc.), asteraceae vegetables (burdock, shungiku, artichoke, lettuce, etc.), liliaceae vegetables (eg, leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery, American Bow Fu etc.), Rubiaceae vegetables (spinach, chard, etc.), Lamiaceae vegetables (shiso, mint
- Fruit trees berries (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (satsuma mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.
- Trees other than fruit trees tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, snapdragon, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, black beetle, Japanese amberjack, eel, pine, pine, spruce, yew, elm, redwood, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi.
- corn, wheat, rice and the like can be mentioned as preferable examples. Of these, rice is particularly preferable.
- the above “plant” may be a plant imparted with herbicide resistance, pest resistance or environmental stress resistance by genetic recombination techniques or breeding methods by crossing.
- the “plant” is rice, the rice variety is not particularly limited.
- the harmful arthropod control composition of the present invention can control harmful arthropods by being applied to plants or plant cultivation areas.
- plants include plant foliage, plant flowers, plant nuts, plant seeds, and the like.
- the method for controlling harmful arthropods of the present invention is carried out by applying the composition for controlling harmful arthropods of the present invention. Specifically, it is applied to the foliage of plants such as foliage spraying, plant seeds. Application to the cultivation area of plants such as treatment to soil, soil treatment, water surface application and the like.
- foliage spraying examples include, for example, ground spraying using a manpower sprayer, power sprayer, boom sprayer or cruckle sprayer, aerial control performed using air control or an unmanned helicopter The method of applying to the surface of the plant currently grown by spraying etc. is mentioned.
- Examples of the treatment for plant seeds in the present invention include immersion treatment, spraying treatment, smearing treatment, film coating treatment, and pellet coating treatment.
- Examples of the application to the plant cultivation area such as soil treatment and water surface application in the present invention include, for example, planting hole treatment, plant source treatment, grooving treatment, rowing treatment, full surface treatment, side row treatment, nursery box treatment, nursery bed Treatment, soil mixing, floor soil mixing, paste fertilizer mixing, water surface treatment and flooding spraying.
- the present invention is preferably applied to seedling box processing.
- the pest control composition of the present invention is applied to a place where rice is raised.
- the place where rice seedlings are grown is a place where rice seedlings are cultivated during the period from seeding of rice to before transplanting.
- Examples of the place where rice is nurtured include soil such as paddy soil, field soil, and mountain soil, artificial soil, or artificially molded medium.
- the rice is transplanted to a place where rice is cultivated.
- places where rice is cultivated include flooded soil such as paddy fields and dry rice fields.
- the application amount is the type of plant, the type and degree of occurrence of harmful arthropods to be controlled, formulation form, application
- the total amount of the present mesoionic compound, the present anthranilamido compound and the present compound A is usually 0.05 to 1000000 g per 1000 m 2 where the plant is cultivated, preferably 0.5. ⁇ 200000g.
- the application amount depends on the type and occurrence of harmful arthropods to be controlled, formulation form, weather conditions, etc.
- the total amount of the mesoionic compound, the anthranilamide compound, and the compound A is usually 0.05 to 1000 g, preferably 0.5 to 200 g, per 1 m 2 of the place where rice is nurtured.
- the application amount is 1 box of a seedling box as a total amount of the mesoionic compound, the anthranilamide compound and the compound A (approximately It is usually 0.1 to 35 g, preferably 0.2 to 20 g per 60 cm (vertical length of about 30 cm).
- the amount of harmful arthropod composition used is the type of plant, the type and occurrence of harmful arthropods to be controlled, the formulation form,
- the total amount of the mesoionic compound, the anthranilamide compound, and the compound A is usually 0.001 to 100 g, preferably 0.05 to 50 g, per 1 kg of seeds.
- the harmful arthropod composition of the present invention is in the form of emulsion, wettable powder, flowable, etc., it is usually applied by diluting with water and spraying.
- the total concentration of the mesoionic compound, the anthranilamide compound and the compound A is usually 0.00001 to 10% by weight, preferably 0.0001 to 5% by weight.
- Powders, granules, etc. are usually applied as they are without dilution.
- the harmful arthropod composition of the present invention When the harmful arthropod composition of the present invention is applied to rice or a rice cultivation site, it can be applied, for example, before sowing, during sowing, after sowing, before transplanting, at the time of transplanting, or after transplanting.
- the period of application may vary depending on the growth state of rice, the occurrence of pests and pests, weather conditions, etc., but it can usually be mentioned from 30 days before sowing to 20 days after transplanting, based on the day of sowing or transplanting rice.
- it is from seeding to transplantation, and more preferably from 3 days before transplantation.
- Formulation Example 1 1 part of the present mesoionic compound (Compound Nos. 1 to 71), 0.75 part of the anthranilamide compound (1), 2 parts of isotianil, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and kaolin 100 parts of the mixture of the remaining clay is pulverized and mixed well, water is added and kneaded well, and then granulated and dried to obtain granules.
- Formulation Examples 2-8 instead of 2 parts of isotianil, the same operation as in Formulation Example 1 is carried out except that each compound and the amount used in [Table 5] are applied, and each granule is obtained.
- Formulation Example 9 1 part of the present mesoionic compound (Compound Nos. 1 to 71), 0.75 part of the anthranilamide compound (2), 2 parts of isotianil, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and kaolin 100 parts of the mixture of the remaining clay is pulverized and mixed well, water is added and kneaded well, and then granulated and dried to obtain granules.
- Formulation Example 17 4 parts of the present mesoionic compound (Compound Nos. 1 to 71), 0.75 part of the anthranilamide compound (1), 2 parts of isothianyl, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and kaolin 100 parts of the mixture of the remaining clay is pulverized and mixed well, water is added and kneaded well, and then granulated and dried to obtain granules.
- Formulation Examples 18-24 The granules are obtained in the same manner as in Formulation Example 17, except that each compound and the amount used are listed in [Table 7] instead of 2 parts of isothianyl.
- Formulation Example 25 4 parts of the present mesoionic compound (Compound Nos. 1 to 71), 0.75 part of the anthranilamide compound (2), 2 parts of isotianil, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and kaolin 100 parts of the mixture of the remaining clay is pulverized and mixed well, water is added and kneaded well, and then granulated and dried to obtain granules.
- Formulation Examples 26-32 The granules are obtained in the same manner as in Formulation Example 25 except that each compound and the amount used are listed in [Table 8] instead of 2 parts of isotianil.
- Formulation Example 33 10 parts of the present mesoionic compound (Compound Nos. 1 to 71), 1 part of the anthranilamide compound (1) and 2 parts of isothianyl, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, and 20 parts of synthetic silicon hydroxide fine powder In addition, the remaining diatomaceous earth is mixed and stirred well to obtain 100 parts of wettable powder.
- Formulation Examples 34 to 39 It replaces with 2 parts of isotianil, and except having applied with each compound and usage-amount of the [Table 9] description, operation similar to the formulation example 33 is performed, and 100 parts of each wettable powder is obtained.
- Formulation Example 40 10 parts of the present mesoionic compound (Compound Nos. 1 to 71), 1 part of the anthranilamide compound (2) and 2 parts of isothianyl, 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide-containing fine powder and Add the remaining diatomaceous earth and mix well to obtain 100 parts wettable powder.
- Formulation Examples 41-46 It replaces with 2 parts of isotianil, and except having applied with each compound and usage-amount of the [Table 10] description, operation similar to the formulation example 40 is performed, and 100 parts of wettable powders are obtained.
- Formulation Example 47 5 parts of this mesoionic compound (Compound Nos. 1 to 71), 3 parts of this anthranilamide compound (1), 2 parts of isothianyl, 30 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt and the remainder of water were mixed. A flowable agent is obtained by pulverizing 100 parts of the mixture by a wet pulverization method.
- Formulation Example 54 5 parts of this mesoionic compound (Compound Nos. 1 to 71), 3 parts of this anthranilamide compound (2), 2 parts of isothianyl, 30 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt and the remainder of water were mixed.
- a flowable agent is obtained by pulverizing 100 parts of the mixture by a wet pulverization method.
- Test example 1 The mesoionic compound (Compound No. 4), the mesoionic compound (Compound No. 44), the anthranilamide compound (1), the anthranilamide compound (2), isothianyl, probenazole, thiazinyl, tricyclazole, orisatrobin and pyroxylone A fixed amount, Solgen TW-20 (Daiichi Kogyo Seiyaku Co., Ltd.) was dissolved in 0.3 ml of acetone (Wako Pure Chemical Industries) containing 5% (w / v), and then diluted with water to a predetermined concentration. The mesoionic compound (compound No. 4) or the mesoionic compound (compound No.
- test drug solution was prepared by mixing with a water-diluted solution of thiazinyl, tricyclazole, orysastrobin or pyroxylone.
- the test chemical solution (0.6 ml) was applied to the root soil of 1 seedling of rice (Oryza sativa, cultivar: Hoshino Yume) in the 2.5 leaf stage planted in a paper pot. The rice was allowed to stand for 2 hours, then transplanted to flooded soil in a 1 / 10000a Wagner pot and placed in a greenhouse (23 ° C.).
- Test example 2 The mesoionic compound (Compound No. 61), the anthranilamide compound (1), the anthranilamide compound (2), isothianyl, probenazole, thiazinyl, tricyclazole, orissastrobin and pyroxylone in a predetermined amount, respectively, Sorgen TW-20 (Daiichi Kogyo) After being dissolved in 0.3 ml of acetone (manufactured by Wako Pure Chemical Industries) containing 5% (w / v), it was diluted with water to a predetermined concentration. Water dilution of this mesoionic compound (Compound No.
- corrected death rate (%) ⁇ (treatment area death rate ⁇ untreatment area death rate) / (100 ⁇ no treatment area death rate) ⁇ ⁇ 100
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Abstract
Description
すなわち、本発明とは以下の[1]~[9]の通りである。
[1] 式(I)
[式中、
Qは、式CR5=CR6で示される基、硫黄原子、酸素原子又は式NCH3で示される基を表し、
R1は、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC2−C4アルケニル基、1個以上のハロゲン原子を有していてもよいC2−C4アルキニル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、シアノ基、ニトロ基又はハロゲン原子を表し、
nは、0~3のいずれかの整数を表し、
R2は、以下の式(R2a)、(R2b)、(R2c)、(R2d)及び(R2e)で示される何れかの基
{式中、
R3a、R3b及びR3cは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC2−C4アルキニル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、シアノ基、ニトロ基又はハロゲン原子を表し、
R3dは、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、シアノ基、ニトロ基又はハロゲン原子を表し、
Xa、Xb、Xc及びXdは同一又は相異なり、0、1又は2を表し、
Zb及びZcは同一又は相異なり、酸素原子、硫黄原子又は式NR7で示される基を表し、
R7は1個以上のハロゲン原子を有していてもよいC1−C4アルキル基又は水素原子を表す。
なお、R3a、R3b、R3c及びR3dがそれぞれ2個ある場合(すなわち、Xa、Xb、Xc及びXdが2である場合)、それぞれのR3a、R3b、R3c及びR3dは同一又は相異なっていてもよい。}を表し、
R5は、水素原子又はフッ素原子を表し、
R6は、水素原子、フッ素原子、ジフルオロメチル基又はトリフルオロメチル基を表す。
なお、nが2又は3である場合、複数のR1は互いに相異なっていてもよい。]で示される化合物と、式(II)
[式中、A1はメチル基を表し、A2は塩素原子又シアノ基を表す。]で示される化合物と、群(A)より選ばれる1種以上の化合物とを含有する有害節足動物防除組成物;
群(A):イソチアニル、プロベナゾール、チアジニル、トリシクラゾール、オリサストロビン及びピロキロンからなる群。
[2] 前記式(I)で示される化合物が、当該式(I)において、
R2が、以下の式(R2a)、(R2b)、(R2c)及び(R2d)で示される何れかの基
[式中、
R3a、R3b及びR3cは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC2−C4アルキニル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、シアノ基、ニトロ基又はハロゲン原子を表し、
R3dは、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、シアノ基、ニトロ基又はハロゲン原子を表し、
Xa、Xb、Xc及びXdは同一又は相異なり、0、1又は2を表し、
Zb及びZcは同一又は相異なり、酸素原子、硫黄原子又は式NR7で示される基を表し、
R7は1個以上のハロゲン原子を有していてもよいC1−C4アルキル基又は水素原子を表す。
なお、R3a、R3b、R3c及びR3dがそれぞれ2個ある場合(すなわち、Xa、Xb、Xc及びXdが2である場合)、それぞれのR3a、R3b、R3c及びR3dは同一又は相異なっていてもよい。]である化合物である[1]に記載の有害節足動物防除組成物。
[3] 式(I)で示される化合物と、式(II)で示される化合物との重量比が、50:1~1:50である[1]又は[2]に記載の有害節足動物防除組成物。
[4] 式(I)で示される化合物と、群(A)より選ばれる1種以上の化合物との重量比が、10:1~1:100である[1]~[3]のいずれかに記載の有害節足動物防除組成物。
[5] [1]~[4]のいずれかに記載の有害節足動物防除組成物の有効量を、植物又は植物の栽培地に施用する工程を含む有害節足動物の防除方法。
[6] 植物又は植物の栽培地に施用する工程が、イネ又はイネの栽培地に施用する工程である[5]に記載の有害節足動物の防除方法。
[7] 有害節足動物が、ウンカ類である[5]又は[6]に記載の有害節足動物の防除方法。
[8] ウンカ類が、トビイロウンカ、セジロウンカ又はヒメトビウンカである[7]に記載の有害節足動物の防除方法。
[9] 有害節足動物防除組成物の有効量を、移植3日前~移植時に施用する[5]~[8]のいずれかに記載の有害節足動物の防除方法。
R2bとしては、例えば、2−フルオロ−5−チアゾリル基、2−クロロ−5−チアゾリル基、2−ブロモ−5−チアゾリル基、2−メチル−5−チアゾリル基、5−チアゾリル基、2−フルオロ−5−オキサゾリル基、2−クロロ−5−オキサゾリル基、5−オキサゾリル基、2−クロロ−1−メチル−5−イミダゾリル基及び2−フルオロ−1−メチル−5−イミダゾリル基が挙げられる。
R2cとしては、例えば、1−メチル−4−ピラゾリル基及び3−メチル−5−イソキサゾリル基が挙げられる。
R2dとしては、例えば、テトラヒドロフラン−2−イル基及びテトラヒドロフラン−3−イル基が挙げられる。
R2eとしては、例えば、5−ピリミジニル基が挙げられる。
式(I)において、nが2であり、R1が互いに同一又は互いに相異なり、フッ素原子、塩素原子、臭素原子、メチル基、メトキシ基、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基、6−クロロ−3−ピリジル基又は5−ピリミジニル基であり、QがCH=CH又は硫黄原子である化合物;
式(I)において、nが1であり、R1がフッ素原子、塩素原子、臭素原子、メチル基、メトキシ基、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基、6−クロロ−3−ピリジル基又は5−ピリミジニル基であり、QがCH=CH又は硫黄原子である化合物;
式(I)において、nが2であり、R1が互いに同一又は互いに相異なり、フッ素原子、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基、6−クロロ−3−ピリジル基又は5−ピリミジニル基であり、QがCH=CH又は硫黄原子である化合物;
式(I)において、nが1であり、R1がフッ素原子、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基、6−クロロ−3−ピリジル基又は5−ピリミジニル基であり、QがCH=CH又は硫黄原子である化合物;
式(I)において、nが2であり、R1が互いに同一又は互いに相異なり、フッ素原子、塩素原子、臭素原子、メチル基、メトキシ基、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基又は6−クロロ−3−ピリジル基であり、QがCH=CH又は硫黄原子である化合物;
式(I)において、nが1であり、R1がフッ素原子、塩素原子、臭素原子、メチル基、メトキシ基、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基又は6−クロロ−3−ピリジル基であり、QがCH=CH又は硫黄原子である化合物;
式(I)において、nが2であり、R1が互いに同一又は互いに相異なり、フッ素原子、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基又は6−クロロ−3−ピリジル基であり、QがCH=CH又は硫黄原子である化合物;
式(I)において、nが1であり、R1がフッ素原子、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基又は6−クロロ−3−ピリジル基であり、QがCH=CH又は硫黄原子である化合物;
式(I)において、nが1であり、R1がフッ素原子又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基又は6−クロロ−3−ピリジル基であり、QがCH=CH又は硫黄原子である化合物;
式(I)において、nが1であり、R1がフッ素原子であり、R2が2−クロロ−5−チアゾリル基であり、QがCH=CHである化合物;
式(I)において、nが2であり、R1が互いに同一又は互いに相異なり、フッ素原子、塩素原子、臭素原子、メチル基、メトキシ基、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基、6−クロロ−3−ピリジル基又は5−ピリミジニル基であり、QがCH=CHである化合物;
式(I)において、nが1であり、R1がフッ素原子、塩素原子、臭素原子、メチル基、メトキシ基、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基、6−クロロ−3−ピリジル基又は5−ピリミジニル基であり、QがCH=CHである化合物;
式(I)において、nが2であり、R1が互いに同一又は互いに相異なり、フッ素原子、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基、6−クロロ−3−ピリジル基又は5−ピリミジニル基であり、QがCH=CHである化合物;
式(I)において、nが1であり、R1がフッ素原子、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が2−クロロ−5−チアゾリル基、6−クロロ−3−ピリジル基又は5−ピリミジニル基であり、QがCH=CHである化合物;
式(I)において、nが1であり、R1がフッ素原子又はトリフルオロメチル基であり、R2が2−クロロ−5−チアゾリル基又は5−ピリミジニル基であり、QがCH=CHである化合物;
式(I)において、nが2であり、R1が互いに同一又は互いに相異なり、フッ素原子、塩素原子、臭素原子、メチル基、メトキシ基、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が5−ピリミジニル基であり、QがCH=CHである化合物;
式(I)において、nが1であり、R1がフッ素原子、塩素原子、臭素原子、メチル基、メトキシ基、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が5−ピリミジニル基であり、QがCH=CHである化合物;
式(I)において、nが2であり、R1が互いに同一又は互いに相異なり、フッ素原子、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が5−ピリミジニル基であり、QがCH=CHである化合物;
式(I)において、nが1であり、R1がフッ素原子、トリフルオロメチル基又はトリフルオロメトキシ基であり、R2が5−ピリミジニル基であり、QがCH=CHである化合物;
式(I)において、nが1であり、R1がトリフルオロメチル基であり、R2が5−ピリミジニル基であり、QがCH=CHである化合物;
式(I)において、nが1であり、R1が1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、又はハロゲン原子であり、R2が1個のハロゲン原子を有したピリジル基、1個のハロゲン原子を有したチアゾリル基、又はピリミジル基であり、QがCH=CH、又は硫黄原子である化合物;
本アントラニルアミド化合物のうち、式(II)において、A1がメチル基であり、A2がシアノ基である化合物(以下、本アントラニルアミド化合物(2)と記す。)は、例えば「The Pesticide Manual−15th edition(BCPC刊);ISBN 978−1−901396−18−8」の251ページに記載されており、該化合物は国際公開第2004/067528号に記載された方法で製造することができる。
本発明に用いられるイソチアニルは公知の化合物であり、例えば国際公開第99/024413号に記載された方法で製造することができる。
本発明の有害節足動物防除組成物における、本発明に用いられる本メソイオン化合物と本化合物Aとの含有割合は、特に限定されないが、本メソイオン化合物と本化合物Aとの重量比が、通常10:1~1:100であり、好ましくは10:1~1:50、より好ましくは5:1~1:50、特に好ましくは1.5:1~1:48である。
また、前記の製剤化された有害節足動物防除組成物は、そのまま又はその他の不活性成分(水、砂、植物油等)を添加して有害節足動物防除剤として使用することができる。
本発明の有害節足動物防除組成物における、本メソイオン化合物、本アントラニルアミド化合物及び本化合物Aの合計量は、通常0.01~100重量%、好ましくは0.1~90重量%、さらに好ましくは0.5~70重量%である。
界面活性剤としては、例えばアルキル硫酸エステル塩、アルキルアリールスルホン酸塩、ジアルキルスルホコハク酸塩、ポリオキシエチレンアルキルアリールエーテルリン酸エステル塩、リグニンスルホン酸塩、ナフタレンスルホネートホルムアルデヒド重縮合物等の陰イオン界面活性剤及びポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンアルキルポリオキシプロピレンブロックコポリマー、ソルビタン脂肪酸エステル等の非イオン界面活性剤、及びアルキルトリメチルアンモニウム塩等の陽イオン界面活性剤が挙げられる。
その他の製剤用補助剤としては、例えばポリビニルアルコール、ポリビニルピロリドン等の水溶性高分子、アラビアガム、アルギン酸及びその塩、CMC(カルボキシメチルセルロース)、ザンサンガム等の多糖類、アルミニウムマグネシウムシリケート、アルミナゾル等の無機物、防腐剤、着色剤及びPAP(酸性リン酸イソプロピル)、BHT(2,6−ジ−tert−ブチル−4−メチルフェノール)等の安定化剤が挙げられる。
鱗翅目害虫:ニカメイガ(Chilo suppressalis)、サンカメイガ(Tryporyza incertulas)、コブノメイガ(Cnaphalocrocis medinalis)、ワタノメイガ(Notarchaderogata)、ノシメマダラメイガ(Plodia interpunctella)、アワノメイガ(Ostrinia furnacalis)、ハイマダラノメイガ(Hellula undalis)、シバツトガ(Pediasia teterrellus)等のメイガ類、ハスモンヨトウ(Spodoptera litura)、シロイチモジヨトウ(Spodoptera exigua)、アワヨトウ(Pseudaletia separata)、イネヨトウ(Sesamia inferens)、ヨトウガ(Mamestra brassicae)、タマナヤガ(Agrotis ipsilon),タマナギンウワバ(Plusia nigrisigna)、イラクサギンウワバ(Trichoplusia ni)、トリコプルシア属、ヘリオティス属、ヘリコベルパ属等のヤガ類、モンシロチョウ(Pieris rapae)等のシロチョウ類、アドキソフィエス属、ナシヒメシンクイ(Grapholita molesta)、マメシンクイガ(Leguminivora glycinivorella),アズキサヤムシガ(Matsumuraeses azukivora)、リンゴコカクモンハマキ(Adoxophyes orana fasciata)、チャノコカクモンハマキ(Adoxophyes honmai.)、チャハマキ(Homona magnanima)、ミダレカクモンハマキ(Archips fuscocupreanus)、コドリンガ(Cydia pomonella)等のハマキガ類、チャノホソガ(Caloptilia theivora)、キンモンホソガ(Phyllonorycter ringoneella)のホソガ類、モモシンクイガ(Carposina niponensis)等のシンクイガ類、リオネティア属等のハモグリガ類、リマントリア属、ユープロクティス属等のドクガ類、コナガ(Plutella xylostella)等のスガ類、ワタアカミムシ(Pectinophora gossypiella)ジャガイモガ(Phthorimaea operculella)等のキバガ類、アメリカシロヒトリ(Hyphantria cunea)等のヒトリガ類等。
双翅目害虫:タマネギバエ(Hylemya antiqua)、タネバエ(Hylemya platura)、イネハモグリバエ(Agromyza oryzae)、イネヒメハモグリバエ(Hydrellia griseola)、イネキモグリバエ(Chlorops oryzae)、マメハモグリバエ(Liriomyza trifolii)等のハモグリバエ類、ウリミバエ(Dacus cucurbitae)、チチュウカイミバエ(Ceratitis capitata)等;
甲虫目害虫:ニジュウヤホシテントウ(Epilachna vigintioctopunctata)、ウリハムシ(Aulacophora femoralis)、キスジノミハムシ(Phyllotreta striolata)、イネドロオイムシ(Oulema oryzae)、イネゾウムシ(Echinocnemus squameus)、イネミズゾウムシ(Lissorhoptrus oryzophilus)、ワタミゾウムシ(Anthonomus grandis)、アズキゾウムシ(Callosobruchus chinensis)、シバオサゾウムシ(Sphenophorus venatus)、マメコガネ(Popillia japonica)、ドウガネブイブイ(Anomala cuprea)、コーンルートワームの仲間(Diabrotica spp.)、コロラドハムシ(Leptinotarsa decemlineata)、コメツキムシの仲間(Agriotes spp.)等。
野菜;ナス科野菜(ナス、トマト、ピーマン、トウガラシ、ジャガイモ等)、ウリ科野菜(キュウリ、カボチャ、ズッキーニ、スイカ、メロン等)、アブラナ科野菜(ダイコン、カブ、セイヨウワサビ、コールラビ、ハクサイ、キャベツ、カラシナ、ブロッコリー、カリフラワー、アブラナ等)、キク科野菜(ゴボウ、シュンギク、アーティチョーク、レタス等)、ユリ科野菜(ネギ、タマネギ、ニンニク、アスパラガス等)、セリ科野菜(ニンジン、パセリ、セロリ、アメリカボウフウ等)、アカザ科野菜(ホウレンソウ、フダンソウ等)、シソ科野菜(シソ、ミント、バジル等)、イチゴ、サツマイモ、ヤマノイモ、サトイモ等。
果樹:仁果類(リンゴ、セイヨウナシ、ニホンナシ、カリン、マルメロ等)、核果類(モモ、スモモ、ネクタリン、ウメ、オウトウ、アンズ、プルーン等)、カンキツ類(ウンシュウミカン、オレンジ、レモン、ライム、グレープフルーツ等)、堅果類(クリ、クルミ、ハシバミ、アーモンド、ピスタチオ、カシューナッツ、マカダミアナッツ等)、液果類(ブルーベリー、クランベリー、ブラックベリー、ラズベリー等)、ブドウ、カキ、オリーブ、ビワ、バナナ、コーヒー、ナツメヤシ、ココヤシ、アブラヤシ等。
果樹以外の樹木:チャ、クワ、花木類(サツキ、ツバキ、アジサイ、サザンカ、シキミ、サクラ、ユリノキ、サルスベリ、キンモクセイ等)、街路樹(トネリコ、カバノキ、ハナミズキ、ユーカリ、イチョウ、ライラック、カエデ、カシ、ポプラ、ハナズオウ、フウ、プラタナス、ケヤキ、クロベ、モミノキ、ツガ、ネズ、マツ、トウヒ、イチイ、ニレ、トチノキ等)、サンゴジュ、イヌマキ、スギ、ヒノキ、クロトン、マサキ、カナメモチ等。
本メソイオン化合物(化合物No.1~71)1部、本アントラニルアミド化合物(1)0.75部、イソチアニル2部、合成含水酸化珪素1部、リグニンスルホン酸カルシウム2部、ベントナイトを30部及びカオリンクレー残部の混合物100部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥することにより粒剤を得る。
イソチアニル2部に代えて、[表5]記載のそれぞれの化合物及び使用量で適用した以外は製剤例1と同様の操作を行い、それぞれの粒剤を得る。
本メソイオン化合物(化合物No.1~71)1部、本アントラニルアミド化合物(2)0.75部、イソチアニル2部、合成含水酸化珪素1部、リグニンスルホン酸カルシウム2部、ベントナイトを30部及びカオリンクレー残部の混合物100部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥することにより粒剤を得る。
イソチアニル2部に代えて、[表6]記載のそれぞれの化合物及び使用量で適用した以外は製剤例9と同様の操作を行い、それぞれの粒剤を得る。
本メソイオン化合物(化合物No.1~71)4部、本アントラニルアミド化合物(1)0.75部、イソチアニル2部、合成含水酸化珪素1部、リグニンスルホン酸カルシウム2部、ベントナイトを30部及びカオリンクレー残部の混合物100部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥することにより粒剤を得る。
イソチアニル2部に代えて、[表7]記載のそれぞれの化合物及び使用量で適用した以外は製剤例17と同様の操作を行い、それぞれの粒剤を得る。
本メソイオン化合物(化合物No.1~71)4部、本アントラニルアミド化合物(2)0.75部、イソチアニル2部、合成含水酸化珪素1部、リグニンスルホン酸カルシウム2部、ベントナイトを30部及びカオリンクレー残部の混合物100部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥することにより粒剤を得る。
イソチアニル2部に代えて、[表8]記載のそれぞれの化合物及び使用量で適用した以外は製剤例25と同様の操作を行い、それぞれの粒剤を得る。
本メソイオン化合物(化合物No.1~71)10部、本アントラニルアミド化合物(1)1部及びイソチアニル2部を、ラウリル硫酸ナトリウム4部、リグニンスルホン酸カルシウム2部、合成含水酸化珪素微粉末20部及び珪藻土残部を混合した中に加え、よく攪拌混合して水和剤100部を得る。
イソチアニル2部に代えて、[表9]記載のそれぞれの化合物及び使用量で適用した以外は製剤例33と同様の操作を行い、それぞれの水和剤100部を得る。
本メソイオン化合物(化合物No.1~71)10部、本アントラニルアミド化合物(2)1及びイソチアニル2部を、ラウリル硫酸ナトリウム4部、リグニンスルホン酸カルシウム2部、合成含水酸化珪素微粉末20部及び珪藻土残部を混合した中に加え、よく攪拌混合して水和剤100部を得る。
イソチアニル2部に代えて、[表10]記載のそれぞれの化合物及び使用量で適用した以外は製剤例40と同様の操作を行い、水和剤100部を得る。
本メソイオン化合物(化合物No.1~71)5部、本アントラニルアミド化合物(1)3部、イソチアニル2部、ポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩50部を含むホワイトカーボン30部及び水残部を混合した混合物100部を湿式粉砕法で微粉砕することにより、フロアブル剤を得る。
イソチアニル2部に代えて、[表11]記載のそれぞれの化合物及び使用量で適用した以外は製剤例47と同様の操作を行い、それぞれのフロアブル剤を得る。
本メソイオン化合物(化合物No.1~71)5部、本アントラニルアミド化合物(2)3部、イソチアニル2部、ポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩50部を含むホワイトカーボン30部及び水残部を混合した混合物100部を湿式粉砕法で微粉砕することにより、フロアブル剤を得る。
イソチアニル2部に代えて、[表12]記載のそれぞれの化合物及び使用量で適用した以外は製剤例54と同様の操作を行い、それぞれのフロアブル剤を得る。
本メソイオン化合物(化合物No.4)、本メソイオン化合物(化合物No.44)、本アントラニルアミド化合物(1)、本アントラニルアミド化合物(2)、イソチアニル、プロベナゾール、チアジニル、トリシクラゾール、オリサストロビン及びピロキロンをそれぞれ所定量、ソルゲンTW−20(第一工業製薬製)を5%(w/v)含むアセトン(和光純薬工業製)0.3mlに溶解させた後、所定濃度になるように水で希釈した。
本メソイオン化合物(化合物No.4)又は本メソイオン化合物(化合物No.44)の水希釈液と、本アントラニルアミド化合物(1)又は本アントラニルアミド化合物(2)の水希釈液と、イソチアニル、プロベナゾール、チアジニル、トリシクラゾール、オリサストロビン又はピロキロンの水希釈液とを混合し、試験用薬液を調製した。
ペーパーポットに植えられた2.5葉期のイネ(Oryza sativa、品種:ほしのゆめ)稚苗1株の株元土壌に前記試験用薬液0.6mlを施用した。このイネを2時間静置した後、1/10000aワグネルポット中の湛水した土壌に移植し、温室(23℃)に置いた。薬液施用1日後、イネの株元をプラスチック製カップで覆い、トビイロウンカの3齢幼虫を10頭ずつ放飼した。これを処理区と呼ぶ。
一方、前記試験用薬液を施用せずに、処理区と同様に、イネを移植し、温室に置いて、幼虫を放飼した。これを無処理区と呼ぶ。
放飼6日後に供試した幼虫の生死を観察した。その観察結果から、式1)によって死虫率、式2)によって補正死虫率を算出した。なお、試験は2反復で行った。その平均値を表13~表17に示す。
式2);補正死虫率(%)={(処理区死虫率−無処理区死虫率)/(100−無処理区死虫率)}×100
本メソイオン化合物(化合物No.61)、本アントラニルアミド化合物(1)、本アントラニルアミド化合物(2)、イソチアニル、プロベナゾール、チアジニル、トリシクラゾール、オリサストロビン及びピロキロンをそれぞれ所定量、ソルゲンTW−20(第一工業製薬製)を5%(w/v)含むアセトン(和光純薬工業製)0.3mlに溶解させた後、所定濃度になるように水で希釈した。
本メソイオン化合物(化合物No.61)の水希釈液と、本アントラニルアミド化合物(1)又は本アントラニルアミド化合物(2)の水希釈液と、イソチアニル、プロベナゾール、チアジニル、トリシクラゾール、オリサストロビン又はピロキロンの水希釈液とを混合し、試験用薬液を調製した。
ペーパーポットに植えられた2.5葉期のイネ(Oryza sativa、品種:ほしのゆめ)稚苗1株の株元土壌に前記試験用薬液0.6mlを施用した。このイネを2時間静置した後、1/10000aワグネルポット中の湛水した土壌に移植し、温室(23℃)に置いた。薬液施用1日後、イネの株元をプラスチック製カップで覆い、トビイロウンカの3齢幼虫を10頭ずつ放飼した。これを処理区と呼ぶ。
一方、前記試験用薬液を施用せずに、処理区と同様に、イネを移植し、温室に置いて、幼虫を放飼した。これを無処理区と呼ぶ。
放飼6日後に供試した幼虫の生死を観察した。その観察結果から、式3)によって死虫率、式4)によって補正死虫率を算出した。なお、試験は2反復で行った。その平均値を表18~表20に示す。
Claims (9)
- 式(I)
[式中、
Qは、式CR5=CR6で示される基、硫黄原子、酸素原子又は式NCH3で示される基を表し、
R1は、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC2−C4アルケニル基、1個以上のハロゲン原子を有していてもよいC2−C4アルキニル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、シアノ基、ニトロ基又はハロゲン原子を表し、
nは、0~3のいずれかの整数を表し、
R2は、以下の式(R2a)、(R2b)、(R2c)、(R2d)及び(R2e)で示される何れかの基
{式中、
R3a、R3b及びR3cは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC2−C4アルキニル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、シアノ基、ニトロ基又はハロゲン原子を表し、
R3dは、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、シアノ基、ニトロ基又はハロゲン原子を表し、
Xa、Xb、Xc、及びXdは同一又は相異なり、0、1又は2を表し、
Zb及びZcは同一又は相異なり、酸素原子、硫黄原子又は式NR7で示される基を表し、
R7は1個以上のハロゲン原子を有していてもよいC1−C4アルキル基又は水素原子を表す。
なお、R3a、R3b、R3c及びR3dがそれぞれ2個ある場合、それぞれのR3a、R3b、R3c及びR3dは同一又は相異なっていてもよい。}を表し、
R5は、水素原子又はフッ素原子を表し、
R6は、水素原子、フッ素原子、ジフルオロメチル基又はトリフルオロメチル基を表す。
なお、nが2又は3である場合、複数のR1は互いに相異なっていてもよい。]で示される化合物と、式(II)
[式中、A1はメチル基を表し、A2は塩素原子又シアノ基を表す。]で示される化合物と、群(A)より選ばれる1種以上の化合物とを含有する有害節足動物防除組成物;
群(A):イソチアニル、プロベナゾール、チアジニル、トリシクラゾール、オリサストロビン及びピロキロンからなる群。 - 前記式(I)で示される化合物が、当該式(I)において、
R2が、以下の式(R2a)、(R2b)、(R2c)及び(R2d)で示される何れかの基
[式中、
R3a、R3b及びR3cは同一又は相異なり、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC2−C4アルキニル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、シアノ基、ニトロ基又はハロゲン原子を表し、
R3dは、1個以上のハロゲン原子を有していてもよいC1−C4アルキル基、1個以上のハロゲン原子を有していてもよいC1−C4アルコキシ基、シアノ基、ニトロ基又はハロゲン原子を表し、
Xa、Xb、Xc及びXdは同一又は相異なり、0、1又は2を表し、
Zb及びZcは同一又は相異なり、酸素原子、硫黄原子又は式NR7で示される基を表し、
R7は1個以上のハロゲン原子を有していてもよいC1−C4アルキル基又は水素原子を表す。
なお、R3a、R3b、R3c及びR3dがそれぞれ2個ある場合、それぞれのR3a、R3b、R3c及びR3dは同一又は相異なっていてもよい。]である化合物である請求項1に記載の有害節足動物防除組成物。 - 式(I)で示される化合物と、式(II)で示される化合物との重量比が、50:1~1:50である請求項1又は2に記載の有害節足動物防除組成物。
- 式(I)で示される化合物と、群(A)より選ばれる1種以上の化合物との重量比が、10:1~1:100である請求項1~3のいずれかに記載の有害節足動物防除組成物。
- 請求項1~4のいずれかに記載の有害節足動物防除組成物の有効量を、植物又は植物の栽培地に施用する工程を含む有害節足動物の防除方法。
- 植物又は植物の栽培地に施用する工程が、イネ又はイネの栽培地に施用する工程である請求項5に記載の有害節足動物の防除方法。
- 有害節足動物が、ウンカ類である請求項5又は6に記載の有害節足動物の防除方法。
- ウンカ類が、トビイロウンカ、セジロウンカ又はヒメトビウンカである請求項7に記載の有害節足動物の防除方法。
- 有害節足動物防除組成物の有効量を、移植3日前~移植時に施用する請求項5~8のいずれかに記載の有害節足動物の防除方法。
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JP6159906B2 (ja) * | 2015-04-21 | 2017-07-05 | 日本化薬株式会社 | メソイオン性化合物 |
JP6928615B2 (ja) * | 2016-12-06 | 2021-09-01 | 日本化薬株式会社 | 3−(ピリジル−2−アミノ)プロピオニトリル及びその類縁体の製造方法 |
CN112851665B (zh) * | 2019-11-28 | 2023-08-08 | 东莞市东阳光农药研发有限公司 | 新型介离子化合物及其在农业中的应用 |
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