WO2012090515A1 - Arthropod pest control composition and method for controlling arthropod pests - Google Patents

Arthropod pest control composition and method for controlling arthropod pests Download PDF

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Publication number
WO2012090515A1
WO2012090515A1 PCT/JP2011/054205 JP2011054205W WO2012090515A1 WO 2012090515 A1 WO2012090515 A1 WO 2012090515A1 JP 2011054205 W JP2011054205 W JP 2011054205W WO 2012090515 A1 WO2012090515 A1 WO 2012090515A1
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Prior art keywords
group
compound
mesoionic compound
metalaxyl
optionally halogenated
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PCT/JP2011/054205
Other languages
French (fr)
Inventor
Norihisa Sakamoto
Emiko Sakamoto
Atsushi Iwata
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Sumitomo Chemical Company, Limited
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Application filed by Sumitomo Chemical Company, Limited filed Critical Sumitomo Chemical Company, Limited
Priority to CN2011800630994A priority Critical patent/CN103260408A/en
Priority to MX2013006939A priority patent/MX2013006939A/en
Priority to CA2819572A priority patent/CA2819572A1/en
Priority to KR1020137019816A priority patent/KR20140018866A/en
Priority to US13/997,452 priority patent/US20130289051A1/en
Priority to EP11852297.8A priority patent/EP2658378A4/en
Priority to BR112013016362A priority patent/BR112013016362A2/en
Priority to JP2011274036A priority patent/JP2012149038A/en
Priority to ARP110104931A priority patent/AR084591A1/en
Publication of WO2012090515A1 publication Critical patent/WO2012090515A1/en

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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
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • 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
    • A01N37/46—N-acyl derivatives
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to an arthropod pest control composition and a method for controlling arthropod pests .
  • Patent Literature 1 and Non-Patent Literature 1
  • Patent Literature 1 WO 2009/099929
  • Non-Patent Literature 1 The Pesticide Manual-15th edition (published BCPC) ; ISBN 978-1-901396-18-8
  • An object of the present invention is to provide an arthropod pest control composition having an excellent control effect on arthropod pests.
  • the present inventors have intensively studied for providing an arthropod pest control composition having an excellent control effect on arthropod pests, and finally found that a composition comprising a compound represented by formula (I) as described below, and a disinfectant compound selected from Group (A) as described below has an excellent control effect on arthropod pests, thereby attaining the present invention.
  • the present invention provides:
  • An arthropod pest control composition comprising a com ound represented by formula (I) :
  • R 1 represents a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group, an optionally halogenated C2-C4 alkenyl group, an optionally halogenated C2-C4 alkynyl group or an optionally halogenated C1-C4 alkoxy group,
  • n an integer of 0 to 3
  • R 2 represents the following R 2a , R 2b , R : 2c or R'
  • R , R and R each independently represent a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group, an optionally halogenated C2-C4 alkynyl group or an optionally halogenated C1-C4 alkoxy group,
  • R 3d represents a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group or an optionally halogenated C1-C4 alkoxy group,
  • X a , X b , X c and X d each independently represent 0, 1 or
  • Z b and Z c each independently represent 0, S or NR 7 ,
  • R 7 represents a hydrogen atom or an optionally halogenated C1-C4 alkyl group
  • 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
  • Group (A) a group consisting of tebuconazole,
  • difenoconazole triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine, pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate, triflumizole, azaconazole,
  • bitertanol bromuconazole, epoxiconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, myclobutanil , penconazole, propiconazole , simeconazole and triadimefon;
  • composition according to any of the above [1] to [3], wherein the composition further comprises metalaxyl or metalaxyl ;
  • the arthropod pest control composition of the present invention comprises a compound represented by the following formula (I) (hereinafter referred to as "the mesoionic compound” ) :
  • R 1 represents a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group, an optionally halogenated C2-C4 alkenyl group, an optionally halogenated C2-C4 alkynyl group or an optionally halogenated C1-C4 alkoxy group,
  • n an integer of 0 to 3
  • R 2 re resents the following R 2a , R 2b , R 2c or R 2d :
  • R 3a , R 3b and R 3c each independently represent a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group, an optionally halogenated C2-C4 alkynyl group or an optionally halogenated C1-C4 alkoxy group,
  • R 3d represents a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group or an optionally halogenated C1-C4 alkoxy group,
  • X a , X b , X c and X d each independently represent 0, 1 or
  • Z b and Z c each independently represent 0, S or NR 7 , R 7 represents a hydrogen atom or an optionally halogenated C1-C4 alkyl group,
  • 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
  • At least one disinfectant compound selected from Group (A) (hereinafter referred to as "the disinfectant compound”);
  • Group (A) a group consisting of tebuconazole,
  • difenoconazole triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine, pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate, triflumizole, azaconazole,
  • bitertanol bromuconazole, epoxiconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, myclobutanil , penconazole, propiconazole, simeconazole and triadimefon .
  • R 1 , R 2a , R 2b , R 2c , R 2d , R 3a , R 3b , R 3c , R 3d and R 7 in the formula (I) include as follows:
  • halogen represented by R 1 , R 3a , R 3b , R 3c or R 3d include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • Examples of the "optionally halogenated C1-C4 alkyl group" represented by R 1 , R 3a , R 3b , R 3c , R 3d or R 7 include a methyl group, a trifluoromethyl group, a trichloromethyl group, a chloromethyl group, a dichloromethyl group, a fluoromethyl group, a difluoromethyl group, an ethyl group, a pentafluoroethyl group, a 2 , 2 , 2-trifluoroethyl group, a 2 , 2 , 2-trichloroethyl group, a propyl group, a 1-methylethyl group, a 1-trifluoromethyltetrafluoroethyl group, a butyl group, a 2-methylpropyl group, a l-methylpropyl group and a 1, 1-dimethylethyl .
  • Examples of the "optionally halogenated C2-C4 alkenyl group" represented by R 1 include a 2-propenyl group, a 3- chloro-2-propenyl group, a 2-chloro-2-propenyl group, a 3 , 3-dichloro-2-propenyl group, a 2-butenyl group, a 3- butenyl group and a 2-methyl-2-propenyl group.
  • Examples of the "optionally halogenated C1-C4 alkynyl group" represented by R 1 , R 3a , R 3b or R 3c include a 2- propynyl group, a 3-chloro-2-propynyl group, a 3-bromo-2- propynyl group, a 2-butynyl group and a 3-butynyl group.
  • Examples of the "optionally halogenated C1-C4 alkoxy group" represented by R 1 , R 3a , R 3b , R 3c or R 3d include a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2, 2, 2-trifluoroethoxy group, a propoxy group, a 1- methylethoxy group, a butoxy group, a 2-methylpropoxy group, a 1-methylpropoxy group and a 1 , 1-dimethylethoxy group.
  • R 2a examples include a 6-fluoro-3-pyridyl group, a 6-chloro-3-pyridyl group, a 6-bromo-3-pyridyl group, a 6- methyl-3-pyridyl group, a 6-cyano-3-pyridyl group, a 3- pyridyl group, a 2-pyridyl group, and a 5 , 6-dichloro-3- pyridyl group.
  • R 2b examples include a 2-fluoro-5-thiazolyl group, a 2-chloro-5-thiazolyl group, a 2-bromo-5-thiazolyl group, a 2-methyl-5-thiazolyl group, a 5-thiazolyl group, a 2- fluoro-5-oxazolyl group, a 2-chloro-5-oxazolyl group, a 5- oxazolyl group, a 2-chloro-l-methyl-5-imidazolyl group and a 2-fluoro-l-methyl-5-imidazolyl group.
  • R c examples include a l-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 1 , R 2 , R 5 , R 6 and n are as defined above.
  • R 1 , R 2 and n are as defined above.
  • R 1 , R 2 and n are as defined above.
  • mesoionic compound examples include as follows:
  • R 1 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, a trifluoromethyl group or a trifluoromethoxy group
  • R 1 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, a trifluoromethyl group or a
  • n 0 or 1
  • R 1 represents a fluorine atom, a trifluoromethyl group or a trifluoromethoxy group
  • R 2 represents a 2-chloro-5-thiazolyl group or a 6-chloro-3- pyridyl group
  • mesoionic compound examples include those represented by formula (I-a):
  • n, R 1 and R 2 represents any combination as shown in Tables 1 and 2.
  • n, R 1 and R 2 represents any combination as shown in Table 3.
  • the mesoionic compound to be used in the present invention includes the forms represented by formula (I) and its ionized forms represented by the formula different from formula (I), and can be used in any of the above forms alone or in a combination of two or more thereof.
  • the mesoionic compound can be prepared, for example, by a process described in WO 2009/099929.
  • azaconazole, bitertanol, bromuconazole, epoxiconazole, fenbuconazole , flusilazole, flutriafol, hexaconazole , imibenconazole, myclobutanil , penconazole, propiconazole, simeconazole, triadimefon, metalaxyl and metalaxyl M to be used in the present invention are known as described, for example, at pages 1072, 354, 1182, 629, 1147, 543, 928, 965, 384, 384, 287, 1096, 663, 1177, 1255, 465, 1250, 854, 868, 1171, 52, 116, 134, 429, 468, 554, 560, 611, 643, 801, 869, 952, 1033, 1145, 737 and 739 of "The Pesticide Manual-15th edition (published BCPC) ; ISBN 978-1-901396-18-8".
  • the disinfectant compounds to be used in the present invention i.e., tebuconazole, difenoconazole,
  • triticonazole imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine,
  • bromuconazole bromuconazole, epoxiconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, myclobutanil, penconazole, propiconazole, simeconazole and triadimefon, are also known as demethylation inhibitors (DMI agents).
  • DMI agents demethylation inhibitors
  • Such disinfectant compound is preferably tebuconazole, difenoconazole , triticonazole , imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole , diniconazole, diniconazole M, cyproconazole, tetraconazole or ipconazole, more preferably tebuconazole, difenoconazole, triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, or ipconazole .
  • the weight ratio of the disinfectant compound to the mesoionic compound is not particularly limited, but is generally 0.001 to 100,000 parts by weight, preferably 0.01 to 10,000 parts by weight of the
  • the arthropod pest control composition of the present invention may further contain, in addition to the mesoionic compound and the disinfectant compound, other agricultural active compounds.
  • other agricultural active compounds include metalaxyl and metalaxyl M, preferably metalaxyl M.
  • the arthropod pest control composition of the present invention may be prepared by simply mixing the mesoionic compound with the disinfectant compound, but generally by mixing the mesoionic compound, the disinfectant compound and an inert carrier, and if necessary, a surfactant and/or other formulation additives, and then formulating the mixture into a dosage form such as an oil solution, an emulsifiable concentrate, a suspension concentrate, a wettable powder, a water dispersible granule, a dust, or a granule.
  • a dosage form such as an oil solution, an emulsifiable concentrate, a suspension concentrate, a wettable powder, a water dispersible granule, a dust, or a granule.
  • arthropod pest control composition may be used directly, or after the addition of other inert ingredients, as an arthropod pest control agent.
  • the total amount of the mesoionic compound and the disinfectant compound in the arthropod pest control is the total amount of the mesoionic compound and the disinfectant compound in the arthropod pest control
  • composition of the present invention is generally 0.1 to 99% by weight, preferably 0.2 to 90% by weight, more preferably 1 to 80% by weight.
  • Examples of the solid carrier used for formulation of the arthropod pest control composition include fine powders or granules of minerals (e.g., kaolin clay, attapulgite clay, bentonite, montmorillonite, acidic white clay, pyrophylite, talc, diatomaceous earth, and calicite) , natural organic substances (e.g., corncob flour, and walnut shell flour), synthetic organic substances (e.g., urea), salts (e.g., calcium carbonate, and ammonium sulfate), and synthetic inorganic substances (e.g., synthetic hydrated silicon oxide) .
  • minerals e.g., kaolin clay, attapulgite clay, bentonite, montmorillonite, acidic white clay, pyrophylite, talc, diatomaceous earth, and calicite
  • natural organic substances e.g., corncob flour, and walnut shell flour
  • synthetic organic substances e.g., urea
  • salts
  • liquid carrier examples include aromatic hydrocarbons (e.g., xylene, alkylbenzene, and methyl naphthalene), alcohols (e.g., 2-propanol, ethylene glycol, propylene glycol, and ethylene glycol monoethyl ether) , ketones (e.g., acetone, cyclohexanone, and isophorone) , vegetable oils (e.g., soybean oil, and cotton oil), petroleum-based aliphatic hydrocarbons, esters,
  • aromatic hydrocarbons e.g., xylene, alkylbenzene, and methyl naphthalene
  • alcohols e.g., 2-propanol, ethylene glycol, propylene glycol, and ethylene glycol monoethyl ether
  • ketones e.g., acetone, cyclohexanone, and isophorone
  • vegetable oils e.g., soybean oil, and cotton oil
  • surfactant examples include anionic
  • surfactants e.g., alkyl sulfate ester salts, alkylaryl sulfonates, dialkyl sulfosuccinates , polyoxyethyle
  • alkylaryl ether phosphate ester salts ligninsulfonates , and naphthalene sulfonate formaldehyde polycondensates
  • nonionic surfactants e.g., polyoxyethylene alkylaryl ethers, polyoxyethylene alkylpolyoxypropylene block copolymers, and sorbitan fatty acid esters
  • cationic surfactants e.g., alkyl trimethyl ammonium salts.
  • formulation additives examples include water- soluble polymers (e.g., polyvinyl alcohol, and polyvinyl pyrrolidone) , polysaccharides [e.g., gum arabic, alginic acid and a salt thereof, CMC (carboxymethyl cellulose) , and xanthane gum], inorganic substances (e.g., aluminum magnesium silicate, and alumina-sol) , preservatives, colorants, and stabilizers [e.g. PAP (isopropyl acid phosphate), and BHT] .
  • water- soluble polymers e.g., polyvinyl alcohol, and polyvinyl pyrrolidone
  • polysaccharides e.g., gum arabic, alginic acid and a salt thereof, CMC (carboxymethyl cellulose) , and xanthane gum
  • inorganic substances e.g., aluminum magnesium silicate, and alumina-sol
  • the arthropod pest control composition of the present invention can be used for protecting plants from damage due to eating or sucking by arthropod pests.
  • Delphacidae such as Laodelphax striatellus
  • Aonidiella aurantii Comstockaspis perniciosa, Unaspis citri, Ceroplastes rubens, Icerya purchasi, Planococcus kraunhiae, Pseudococcus longispinis, and Pseudaulacaspis pentagona; Tingidae; Cimicoidea such as Cimex lectularius; Psyllidae such as Cacopsylla pyricola; etc.
  • Pyralidae such as Chilo suppressalis, Tryporyza incertulas, Cnaphalocrocis medinalis, Notarcha derogata , Plodia interpunctella , Ostrinia furnacalis, Hellula undalis, and Pediasia teterrellus; Noctuidae such as Spodoptera litura, Spodoptera exigua, Pseudaletia separata, Sesamia inferens, Mamestra brassicae, Agrotis ipsilon, Plusia nigrisigna, Trichoplusia ni, Thoricoplusia spp., Heliothis spp., and Helicoverpa spp.; Pieridae such as Pieris rapae; Tortricidae such as Adoxophyes spp., Grapholita molesta, Leguminivora glycinivorella , Matsumuraeses azukivora
  • Adoxophyes orana fasciata Adoxophyes honmai., Homona magnanima , Archips fuscocupreanus, and Cydia pomonella;
  • Gracillariidae such as Caloptilia theivora
  • Carposinidae such as Carposina niponensis
  • Lyonetiidae such as Lyonetia spp.
  • Lymantriidae such as Lymantria spp.
  • Euproctis spp. Yponomeutidae such as Plutella xylostella
  • Gelechiidae such as
  • Arctiidae such as Hyphantria cunea
  • Tineidae such as Tinea translucens, and Tineola bisselliella
  • Tuta absoluta etc.
  • Thysanoptera
  • Thripidae such as Frankliniella occidentalis, Thrips peri, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Frankliniella fusca, Stenchaetothrips biformis, Haplothrips aculeatus; etc.
  • Agromyzidae such as Hylemya antiqua, Hylemya platura,
  • Gryllotalpa africana Oxya yezoensis, Oxya japonica; etc .
  • the arthropod pest control composition of the present invention may be used for controlling plant diseases, for example, diseases caused by Rhizoctonia spp. or Fusarium spp. in corn, rice, soybean, cotton, rapeseed, or wheat.
  • the arthropod pest control composition of the present invention can be used in agricultural lands such as fields, paddy fields, dry fields, lawns, and orchards or.
  • composition of the present invention can be also used for controlling pests in agricultural lands, etc. in which
  • plants are grown.
  • control composition of the present invention can be applied include as described below:
  • Crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugar cane, tobacco, etc.;
  • Vegetables Solanaceae vegetables (eggplant, tomato, green pepper, hot pepper, potato, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Cruciferae vegetables (Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, cauliflower, rape, etc.), Compositae vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceae vegetables (Welsh onion, onion, garlic, asparagus, etc.), Umbelliferae vegetables (carrot, parsley, celery, parsnip, etc. ) , Chenopodiaceae vegetables (spinach, Swiss chard, etc.), Labiatae vegetables (Japanese basil, mint, basil, etc.), strawberry, sweat potato, yam, aroid, etc . ;
  • Fruit trees pomaceous fruits (apple, common pear, Japanese pear, Chinese quince, quince, etc.), stone fleshy fruits (peach, plum, nectarine, Japanese plum, cherry, apricot, prune, etc.), citrus plants (Satsuma mandarin, orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazel nut, almond, pistachio, cashew nut, macadamia nut, etc.), berry fruits (blueberry, cranberry, blackberry, raspberry, etc.), grape, persimmon, olive, loquat, banana, coffee, date, coconut, oil palm, etc.;
  • Trees other than fruit trees tea, mulberry,
  • flowering trees (azalea, camellia, hydrangea, sasanqua, Japanese star anise, cherry, tulip tree, crape myrtle, orange osmanthus, etc.), street trees (ash tree, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree, oak, poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanese arborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce, yew, spruce, elm, horse chestnut, etc. ) , coral tree, podocarpus, cedar, Japanese cypress, croton, Euonymus japonicus, Photinia glabra, etc.;
  • flowers (rose, carnation, chrysanthemum, prairie gentian, gypsophila, gerbera, marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, convallaria, lavender, stock, ornamental cabbage, primula, poinsettia, gladiolus, cattleya, daisy, cymbidium, begonia, etc.), bio-fuel plants (Jatropha, safflower, camelina, switchgrass, Miscanthus, reed canary grass, giant reed, kenaf, cassava, willow, etc.),
  • corn, rice, soybean, cotton, rapeseed, wheat, etc. are suitable for the present
  • plants as used herein may be those having resistance, which is imparted by a genetic engineering technique or a cross-breeding method.
  • the arthropod pest control composition of the present invention can be applied to plants or area in which plants are grown for controlling arthropod pests therein.
  • the plants as used herein include the stems and leaves of plants, the flowers of plants, the fruits of plants, the seeds of plants, and the bulbs of plants.
  • the bulbs as used herein include scaly bulbs, corms, root stalks, tubers, tuberous roots, and rhizophores.
  • the method for controlling arthropod pests of the present invention comprises applying an effective amount of the arthropod pest control composition of the present invention to plants or area in which plants are grown.
  • the inventive method also includes embodiments in which the mesoionic compound and the disinfectant compound are applied separately or sequentially.
  • the "effective amount of the arthropod pest control composition” as used herein means the total amount of the mesoionic compound and the disinfectant compound, which is capable of exerting the controlling effect on an arthropod pest .
  • Examples of application methods include application to the stems and leaves of plants such as foliage
  • foliage application in the present inevtnion examples include application to the surface of cultivated plants such as ground application by using manual sprayers, power sprayers, boom sprayers or Pancle sprayers, or aerial application or spraying by using radio control helicopters, etc .
  • spray coating treatment on the surface of seeds or bulbs dressing treatment on the seeds or bulbs of plants.
  • immersion treatment film coating treatment and pellet coating treatment.
  • Specific examples of the application to area in which plants are grown such as soil application and submerged application in the present inevtnion include planting hole treatment, plant foot treatment, planting furrow treatment, planting row treatment, broadcast treatment, side row treatment, seedling box treatment, seedbed treatment, mixing with culture soil, mixing with seedbed soil, mixing with a paste fertilizer, water surface treatment, etc.
  • the application amount varies depending on the kinds of plants to be protected, the species or population size of arthropod pests to be controlled, the form of a formulation, the timing of application, weather conditions, etc., but is generally within a range from 0.05 to 10,000 g, preferably from 0.5 to 1,000 g per 1,000 m 2 of an area where plants are grown, in terms of the total amount of the mesoionic compound and the disinfectant compound.
  • the application amount varies depending on the kinds of plants to be protected, the species or population size of
  • arthropod pests to be controlled the form of a formulation, the timing of application, weather conditions, etc., but is generally within a range from 0.001 to 100 g, preferably from 0.05 to 50 g per 1 kg of the seeds, in terms of the total amount of the mesoionic compound and the disinfectant compound .
  • the arthropod pest control composition of the present invention is in the form of an emulsifiable concentrate, a wettable powder or a suspension concentrate are generally applied after dilution with water.
  • the total concentration of the mesoionic compound and the disinfectant compound is generally 0.00001 to 10% by weight, preferably 0.0001 to 5% by weight.
  • the arthropod pest control composition of the present invention in the form of a dust or a granule is generally applied as it is without dilution .
  • the term "part(s)” means part(s) by weight unless otherwise specified, and "the mesoionic compound No. X" (e.g., “the mesoionic compound No. 4") refers to “compound No. X” (e.g., “compound No. 4") in Tables 1 to 3.
  • alkylether sulfate are mixed with water to a total amount of 100 parts, and then the mixture is finely-ground by a wet grinding method to obtain a suspension concentrate.
  • Group (A) a group consisting of tebuconazole,
  • difenoconazole triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine, pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate, triflumizole , azaconazole,
  • bitertanol bromuconazole, epoxiconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, myclobutanil , penconazole, propiconazole, simeconazole and triadimefon .
  • Formulation Example 17 The procedure as described in Formulation Example 16 is repeated, except that the mesoionic compound No. 5 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
  • M 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and the rest parts of synthetic hydrated silicon oxide are well mixed while grinding to obtain 100 parts of a wettable powder.
  • the seedlings of rice ⁇ Oryza sativa; cultivar: Hoshinoyume) at the 1.5 leaf stage were immersed in each test solution. After that, the rice seedlings were air- died and put in plastic test tubes (diameter: 15 mm;
  • Insect death rate (%) ⁇ (Number of tested insects - number of surviving insects ) /Number of tested insects ⁇ x 100
  • each test solution was added thereto at the rate of 1 ml per 100 seeds. Then, each cup was shaken by hand to apply the test solution to the seeds (dressing treatment) . On the same day, 10 treated seeds from each cup were planted in a 160-ml plastic cup
  • Nilaparvata lugens were released onto the germinated rice in each cup, and the cup was placed in a room at 25°C and 55% relative humidity.
  • Insect death rate (%) ⁇ (Number of tested insects - number of surviving insects ) /Number of tested insects ⁇ x 100
  • the term "mg ai/seed” means milligram compound per one seed applied in the test.
  • Test Example 3 Each 10 mg of the mesoionic compound No. 1 and tebuconazole was dissolved in 0.2 ml of a 5% (weight/volume) solution of SORGEN TW-20 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in acetone (manufactured by Wako Pure Chemical Industries, Ltd.) and then diluted with water to given concentrations.
  • SORGEN TW-20 manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.
  • acetone manufactured by Wako Pure Chemical Industries, Ltd.
  • Each of the water dilutions of the mesoionic compound No. 1 was mixed with the water dilution of tebuconazole to prepare a test solution.
  • each test solution was added thereto at the rate of 1 ml per 100 seeds. Then, each cup was shaken by hand to apply the test solution to the seeds (dressing treatment) . On the same day, 10 treated seeds from each cup were planted in a 160-ml plastic cup
  • Insect death rate (%) ⁇ (Number of tested insects - number of surviving insects) /Number of tested insects ⁇ x 100
  • the term "mg ai/seed” means milligram compound per one seed applied in the test.
  • soybean seed is spray-coated in a 15 ml
  • each test solution (5 ⁇ ) containing 2 mg of the mesoionic compound Nos. 1, 4, 5, 42 or 44, and 0.2 mg of prothioconazole, diniconazole, diniconazole M, cyproconazole or tetraconazole, and then the treated seed is planted in a 1/10, 000a Wagner pot filled with soil and grown in a greenhouse for 12 days. About 20 insects of Aulacorthum solani are released into each pot. This . is called a treated-section .
  • Aulacorthum solani is counted in the treated-section and the untreated-section, and a controlling value is
  • An insect death rate is calculated according to the following equation.
  • Controlling value (I) ⁇ 1 - (Cb x Tai)/(Cai x Tb) ⁇ x 100 wherein,
  • Cb the number of insects in an untreated section before treatment
  • Tb the number of insects in a treated-section before treatment

Abstract

Disclosed is an arthropod pest control composition having an excellent controlling effect on arthropod pests, which comprises a compound represented by formula (I) wherein each symbol is as defined in the description; and at least one disinfectant compound selected from Group (A); Group (A): a group consisting of tebuconazole, difenoconazole, triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine, pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate, triflumizole, azaconazole, bitertanol, bromuconazole, epoxiconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, myclobutanil, penconazole, propiconazole, simeconazole and triadimefon.

Description

DESCRIPTION
ARTHROPOD PEST CONTROL COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
Technical Field
[0001]
The present application was filed claiming the
priority of the Japanese Patent Application No. 2010-289611, the entire contents of which are herein incorporated by the reference .
The present invention relates to an arthropod pest control composition and a method for controlling arthropod pests .
Background Art
[0002]
Heretofore, various compounds are known as active ingredients in arthropod pest control compositions (see, for example, Patent Literature 1 and Non-Patent Literature 1) -
Citation List
Patent Literature
[0003]
Patent Literature 1: WO 2009/099929
Non-Patent Literature
[0004]
Non-Patent Literature 1: The Pesticide Manual-15th edition (published BCPC) ; ISBN 978-1-901396-18-8
Summary of Invention
Technical Problem
[0005]
An object of the present invention is to provide an arthropod pest control composition having an excellent control effect on arthropod pests.
Solution to Problem
[0006]
The present inventors have intensively studied for providing an arthropod pest control composition having an excellent control effect on arthropod pests, and finally found that a composition comprising a compound represented by formula (I) as described below, and a disinfectant compound selected from Group (A) as described below has an excellent control effect on arthropod pests, thereby attaining the present invention.
The present invention provides:
[1] An arthropod pest control composition comprising a com ound represented by formula (I) :
Figure imgf000003_0001
wherein,
Q represents CR5=CR6, S, 0 or NCH3,
R1 represents a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group, an optionally halogenated C2-C4 alkenyl group, an optionally halogenated C2-C4 alkynyl group or an optionally halogenated C1-C4 alkoxy group,
n represents an integer of 0 to 3,
2 represents the following R2a, R2b, R: 2c or R'
Figure imgf000003_0002
wherein, R , R and R each independently represent a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group, an optionally halogenated C2-C4 alkynyl group or an optionally halogenated C1-C4 alkoxy group,
R3d represents a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group or an optionally halogenated C1-C4 alkoxy group,
Xa, Xb, Xc and Xd each independently represent 0, 1 or
2,
Zb and Zc each independently represent 0, S or NR7,
R7 represents a hydrogen atom or an optionally halogenated C1-C4 alkyl group,
wherein,
when Xa represents 2, then two R3a's may be the same or different,
when Xb represents 2, then two R3b|s may be the same or different,
when Xc represents 2, then two R3c's may be the same or different, and
when Xd represents 2, then two R3d's may be the same or different,
R5 represents a hydrogen atom or a fluorine atom, and R6 represents a hydrogen atom, a fluorine atom, a difluoromethyl group or a trifluoromethyl group,
wherein,
when n represents 2 or 3, then plural R1 ' s may be the same or different; and
at least one disinfectant compound selected from Group (A) ; Group (A) : a group consisting of tebuconazole,
difenoconazole, triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine, pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate, triflumizole, azaconazole,
bitertanol, bromuconazole, epoxiconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, myclobutanil , penconazole, propiconazole , simeconazole and triadimefon;
[2] The arthropod pest control composition according to the above [1], wherein the weight ratio of the compound represented by formula (I) to the disinfectant compound is 10,000:1 to 0.01:1;
[3] The arthropod pest control composition according to the above [1] or [2], wherein the disinfectant compound is tebuconazole, difenoconazole, triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazole M, cyproconazole, tetraconazole or ipconazole;
[4] The arthropod pest control composition according to any of the above [1] to [3], wherein the composition further comprises metalaxyl or metalaxyl ;
[5] The arthropod pest control composition according to the above [4], wherein the weight ratio of the compound represented by formula (I) to metalaxyl or metalaxyl M is 10,000:1 to 0.01:1;
[6] A method for controlling arthropod pests, which
comprises applying an effective amount of the arthropod pest control composition according to any of the above [1] to [5] to plants or area in which plants are grown;
[7] The method for controlling arthropod pests according to the above [6], wherein the plants or area in which plants are grown is the seeds of plants.
Effects of Invention
[0007]
According to the present invention, it is possible to control arthropod pests.
[0008]
The arthropod pest control composition of the present invention comprises a compound represented by the following formula (I) (hereinafter referred to as "the mesoionic compound" ) :
Figure imgf000006_0001
wherein,
Q represents CR5=CR6, S, 0 or NCH3,
R1 represents a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group, an optionally halogenated C2-C4 alkenyl group, an optionally halogenated C2-C4 alkynyl group or an optionally halogenated C1-C4 alkoxy group,
n represents an integer of 0 to 3,
R2 re resents the following R2a, R2b, R2c or R2d:
Figure imgf000006_0002
wherein,
R3a, R3b and R3c each independently represent a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group, an optionally halogenated C2-C4 alkynyl group or an optionally halogenated C1-C4 alkoxy group,
R3d represents a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group or an optionally halogenated C1-C4 alkoxy group,
Xa, Xb, Xc and Xd each independently represent 0, 1 or
2,
Zb and Zc each independently represent 0, S or NR7, R7 represents a hydrogen atom or an optionally halogenated C1-C4 alkyl group,
wherein,
when Xa represents 2, then two R3a's may be the same or different, when Xb represents 2, then two R3b's may be the same or different,
when Xc represents 2, then two R3c ' s may be the same or different, and
when Xd represents 2, then two R3d's may be the same or different,
R5 represents a hydrogen atom or a fluorine atom, and R6 represents a hydrogen atom, a fluorine atom, a difluoromethyl group or a trifluoromethyl group,
wherein,
when n represents 2 or 3, then plural R11 s may be the same or different; and
at least one disinfectant compound selected from Group (A) (hereinafter referred to as "the disinfectant compound"); Group (A) : a group consisting of tebuconazole,
difenoconazole, triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine, pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate, triflumizole, azaconazole,
bitertanol, bromuconazole, epoxiconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, myclobutanil , penconazole, propiconazole, simeconazole and triadimefon .
[0009]
Examples of R1, R2a, R2b, R2c, R2d, R3a, R3b, R3c, R3d and R7 in the formula (I) include as follows:
[0010]
Examples of the "halogen" represented by R1, R3a, R3b, R3c or R3d include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
[0011]
Examples of the "optionally halogenated C1-C4 alkyl group" represented by R1, R3a, R3b, R3c, R3d or R7 include a methyl group, a trifluoromethyl group, a trichloromethyl group, a chloromethyl group, a dichloromethyl group, a fluoromethyl group, a difluoromethyl group, an ethyl group, a pentafluoroethyl group, a 2 , 2 , 2-trifluoroethyl group, a 2 , 2 , 2-trichloroethyl group, a propyl group, a 1-methylethyl group, a 1-trifluoromethyltetrafluoroethyl group, a butyl group, a 2-methylpropyl group, a l-methylpropyl group and a 1, 1-dimethylethyl .
[0012]
Examples of the "optionally halogenated C2-C4 alkenyl group" represented by R1 include a 2-propenyl group, a 3- chloro-2-propenyl group, a 2-chloro-2-propenyl group, a 3 , 3-dichloro-2-propenyl group, a 2-butenyl group, a 3- butenyl group and a 2-methyl-2-propenyl group.
[0013]
Examples of the "optionally halogenated C1-C4 alkynyl group" represented by R1, R3a, R3b or R3c include a 2- propynyl group, a 3-chloro-2-propynyl group, a 3-bromo-2- propynyl group, a 2-butynyl group and a 3-butynyl group.
[0014]
Examples of the "optionally halogenated C1-C4 alkoxy group" represented by R1, R3a, R3b, R3c or R3d include a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2, 2, 2-trifluoroethoxy group, a propoxy group, a 1- methylethoxy group, a butoxy group, a 2-methylpropoxy group, a 1-methylpropoxy group and a 1 , 1-dimethylethoxy group.
[0015]
Examples of R2a include a 6-fluoro-3-pyridyl group, a 6-chloro-3-pyridyl group, a 6-bromo-3-pyridyl group, a 6- methyl-3-pyridyl group, a 6-cyano-3-pyridyl group, a 3- pyridyl group, a 2-pyridyl group, and a 5 , 6-dichloro-3- pyridyl group.
Examples of R2b include a 2-fluoro-5-thiazolyl group, a 2-chloro-5-thiazolyl group, a 2-bromo-5-thiazolyl group, a 2-methyl-5-thiazolyl group, a 5-thiazolyl group, a 2- fluoro-5-oxazolyl group, a 2-chloro-5-oxazolyl group, a 5- oxazolyl group, a 2-chloro-l-methyl-5-imidazolyl group and a 2-fluoro-l-methyl-5-imidazolyl group. Examples of R c include a l-methyl-4-pyrazolyl group and a 3-methyl-5-isoxazolyl group.
Examples of R2d include a tetrahydrofuran-2-yl group and a tetrahydrofuran-3-yl group.
[0016]
The compound represented by formula (I) wherein Q represents CR5=CR6 is represented by the following formula II-a) :
Figure imgf000009_0001
wherein R1, R2, R5, R6 and n are as defined above.
[0017]
The compound represented by formula (I) wherein Q represents S is represented by the following formula (II b) :
Figure imgf000009_0002
wherein R1, R2 and n are as defined above.
[0018]
The compound represented by formula (I) wherein Q represents 0 is represented by the following formula (II
( II-c )
Figure imgf000009_0003
wherein R1, R2 and n are as defined above.
[0019]
The compound represented by formula (I) wherein Q represents NCH3 is represented by the following formula (II-d) :
Figure imgf000010_0001
wherein R1, R2 and n are as defined above.
[0020]
Examples of the mesoionic compound include as follows:
those represented by formula (I) wherein n represents 0 or 1, when n represents 0, R2 represents a 2-chloro-5- thiazolyl group, a l-methyl-4-pyrazolyl group, a 6-chloro- 3-pyridyl group or a tetrahydrofuran-3-yl group, and Q is CH=CH or S, and when n represents 1, R1 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, a trifluoromethyl group or a trifluoromethoxy group, and R2 represents a 2-chloro-5- thiazolyl group, a 6-chloro-3-pyridyl group, a l-methyl-4- pyrazolyl group or a tetrahydrofuran-3-yl group, and Q is CH=CH or S;
those represented by formula (I) wherein n represents 0 or 1, and when n represents 1, then R1 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, a trifluoromethyl group or a
trifluoromethoxy group, and R2 represents a 2-chloro-5- thiazolyl group, a 6-chloro-3-pyridyl group, a l-methyl-4- pyrazolyl group or a tetrahydrofuran-3-yl group, and Q is CH=CH or S;
those represented by formula (I) wherein n represents 0 or 1, when n represents 0, R2 represents a 2-chloro-5- thiazolyl group, and Q represents CH=CH, and when n represents 1, R1 represents a fluorine atom, a
trifluoromethyl group or a trifluoromethoxy group, and R2 represents a 2-chloro-5-thiazolyl group or a 6-chloro-3- pyridyl group, and Q represents CH=CH;
those represented by formula (I) wherein n represents 0 or 1, and when n represents 1, R1 represents a fluorine atom, a trifluoromethyl group or a trifluoromethoxy group, and R2 represents a 2-chloro-5-thiazolyl group or a 6-chloro-3- pyridyl group, and Q represents CH=CH.
[0021]
Specific examples of the mesoionic compound include those represented by formula (I-a):
Figure imgf000011_0001
wherein a combination of n, R1 and R2 represents any combination as shown in Tables 1 and 2.
[0022]
Table 1
Compound n R1 R2
No.
1 0 - - 2-chloro-5-thiazolyl
2 .0 - - 1-methyl-4 -pyrazolyl
3 0 - - tetrahydrofuran-3-yl
4 1 2-F - 2-chloro-5-thiazolyl
5 1 2-F - 6-chloro-3-pyridyl
6 1 2-F - 1-methyl-4-pyrazolyl
7 1 2-OCF3 - 2-chloro-5-thiazolyl
8 1 2-OC F3 - 6-chloro-3-pyridyl
9 1 3-Br - 6-chloro-3-pyridyl
10 1 3-Br - 2-chloro-5-thiazolyl
11 1 3-CF3 - 2-chloro-5-thiazolyl
12 1 3-CF3 - 6-chloro-3-pyridyl
13 1 3-F -■ 6-chloro-3-pyridyl
14 1 3-F - 2-chloro-5-thiazolyl
15 1 3-OC F3 - 2-chloro-5-thiazolyl
16 1 3-OCF3 - 6-chloro-3-pyridyl
17 1 3-OCF3 - 1-methyl-4-pyrazolyl
18 1 4-CF3 - 6-chloro-3-pyridyl
19 1 4-CF3 - 2-chloro-5-thiazolyl
20 1 4-F - 2-chloro-5-thiazolyl
[0023]
Table 2
Figure imgf000013_0001
In Tables 1 and 2, the "3-" as shown in the substituents "3-OCF3", "3-Br", etc. of R1 means that such substituent is present as R1 at the 3-position of the benzene ring in the above formula (I-a).
[0024]
Compounds represented by formula (I-b) :
Figure imgf000014_0001
wherein a combination of n, R1 and R2 represents any combination as shown in Table 3.
[0025]
Table 3
Figure imgf000014_0002
In Table 3, the "3-" as shown in the substituents "3- OCF3", "3-F", etc. of R1 means that such substituent is present as R1 at the 3-position of the benzene ring in the above formula (I-b).
[0026]
The mesoionic compound to be used in the present invention includes the forms represented by formula (I) and its ionized forms represented by the formula different from formula (I), and can be used in any of the above forms alone or in a combination of two or more thereof.
[0027]
The mesoionic compound can be prepared, for example, by a process described in WO 2009/099929.
[0028]
Tebuconazole, difenoconazole, triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine, pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate, triflumizole,
azaconazole, bitertanol, bromuconazole, epoxiconazole, fenbuconazole , flusilazole, flutriafol, hexaconazole , imibenconazole, myclobutanil , penconazole, propiconazole, simeconazole, triadimefon, metalaxyl and metalaxyl M to be used in the present invention are known as described, for example, at pages 1072, 354, 1182, 629, 1147, 543, 928, 965, 384, 384, 287, 1096, 663, 1177, 1255, 465, 1250, 854, 868, 1171, 52, 116, 134, 429, 468, 554, 560, 611, 643, 801, 869, 952, 1033, 1145, 737 and 739 of "The Pesticide Manual-15th edition (published BCPC) ; ISBN 978-1-901396-18-8". These compounds are commercially available, or can be produced by known methods .
[0029]
The disinfectant compounds to be used in the present invention, i.e., tebuconazole, difenoconazole,
triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine,
pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate, triflumizole, azaconazole, bitertanol,
bromuconazole, epoxiconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, myclobutanil, penconazole, propiconazole, simeconazole and triadimefon, are also known as demethylation inhibitors (DMI agents).
Such disinfectant compound is preferably tebuconazole, difenoconazole , triticonazole , imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole , diniconazole, diniconazole M, cyproconazole, tetraconazole or ipconazole, more preferably tebuconazole, difenoconazole, triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, or ipconazole .
[0030]
In the arthropod pest control composition of the present invention, the weight ratio of the disinfectant compound to the mesoionic compound is not particularly limited, but is generally 0.001 to 100,000 parts by weight, preferably 0.01 to 10,000 parts by weight of the
disinfectant compound, relative to 100 parts by weight of the mesoionic compound, i.e., [the compound represented by formula ( I )]: (disinfectant compound) = 10, 000:1 to 0.01:1, more preferably [the compound represented by formula
(I) ]: (disinfectant compound) = 1,000:1 to 0.1:1.
[0031]
The arthropod pest control composition of the present invention may further contain, in addition to the mesoionic compound and the disinfectant compound, other agricultural active compounds. Examples of other agricultural active compounds include metalaxyl and metalaxyl M, preferably metalaxyl M.
[0032]
When the arthropod pest control composition of the present invention further contains metalaxyl or metalaxyl M in addition to the mesoionic compound and the disinfectant compound, the weight ratio of metalaxyl or metalaxyl M to the mesoionic compound is not particularly limited, but is generally 0.001 to 100,000 parts by weight, preferably 0.01 to 10,000 parts by weight of metalaxyl or metalaxyl M, relative to 100 parts by weight of the mesoionic compound i.e., [the compound represented by formula ( I )]: (metalaxyl or metalaxyl M) = 10,000:1 to 0.01:1, more preferably [the compound represented by formula ( I )]: (metalaxyl or metalaxyl M) = 1,000:1 to 0.1:1..
[0033] .
The arthropod pest control composition of the present invention may be prepared by simply mixing the mesoionic compound with the disinfectant compound, but generally by mixing the mesoionic compound, the disinfectant compound and an inert carrier, and if necessary, a surfactant and/or other formulation additives, and then formulating the mixture into a dosage form such as an oil solution, an emulsifiable concentrate, a suspension concentrate, a wettable powder, a water dispersible granule, a dust, or a granule.
Thus formulated arthropod pest control composition may be used directly, or after the addition of other inert ingredients, as an arthropod pest control agent.
The total amount of the mesoionic compound and the disinfectant compound in the arthropod pest control
composition of the present invention is generally 0.1 to 99% by weight, preferably 0.2 to 90% by weight, more preferably 1 to 80% by weight.
[0034]
Examples of the solid carrier used for formulation of the arthropod pest control composition include fine powders or granules of minerals (e.g., kaolin clay, attapulgite clay, bentonite, montmorillonite, acidic white clay, pyrophylite, talc, diatomaceous earth, and calicite) , natural organic substances (e.g., corncob flour, and walnut shell flour), synthetic organic substances (e.g., urea), salts (e.g., calcium carbonate, and ammonium sulfate), and synthetic inorganic substances (e.g., synthetic hydrated silicon oxide) .
Examples of the liquid carrier include aromatic hydrocarbons (e.g., xylene, alkylbenzene, and methyl naphthalene), alcohols (e.g., 2-propanol, ethylene glycol, propylene glycol, and ethylene glycol monoethyl ether) , ketones (e.g., acetone, cyclohexanone, and isophorone) , vegetable oils (e.g., soybean oil, and cotton oil), petroleum-based aliphatic hydrocarbons, esters,
dimethylsulfoxide , acetonitrile, and water.
Examples of the surfactant include anionic
surfactants (e.g., alkyl sulfate ester salts, alkylaryl sulfonates, dialkyl sulfosuccinates , polyoxyethyle
alkylaryl ether phosphate ester salts, ligninsulfonates , and naphthalene sulfonate formaldehyde polycondensates ) , nonionic surfactants (e.g., polyoxyethylene alkylaryl ethers, polyoxyethylene alkylpolyoxypropylene block copolymers, and sorbitan fatty acid esters), and cationic surfactants (e.g., alkyl trimethyl ammonium salts).
Examples of the formulation additives include water- soluble polymers (e.g., polyvinyl alcohol, and polyvinyl pyrrolidone) , polysaccharides [e.g., gum arabic, alginic acid and a salt thereof, CMC (carboxymethyl cellulose) , and xanthane gum], inorganic substances (e.g., aluminum magnesium silicate, and alumina-sol) , preservatives, colorants, and stabilizers [e.g. PAP (isopropyl acid phosphate), and BHT] .
[0035]
The arthropod pest control composition of the present invention can be used for protecting plants from damage due to eating or sucking by arthropod pests.
[0036]
Examples of arthropod pests on which the arthropod pest control composition of the present invention has controlling effect include as described below:
[0037]
Hemiptera:
Delphacidae such as Laodelphax striatellus,
Nilaparvata lugens, Sogatella furcifera; Deltocephalidae such as Nephotettix cincticeps, Nephotettix virescens, Recilia dorsalis, Empoasca onukii; Aphididae such as Aphis gossypii , Myzus persicae, Brevicoryne brassicae, Aphis spiraecola , Macrosiphum euphorbiae, Aulacorthum solani, Rhopalosiphum padi, Toxoptera citricidus, Hyalopterus pruni, Eriosoma lanigerum; Pentatomidae such as Nezara antennata , Trigonotylus caelestialium, Graphosoma rubrolineatum,
Eysarcoris lewisi, Riptortus clavetus, Leptocorisa
chinensis, Eysarcoris parvus, Halyomorpha mista, Nezara viridula , and Lygus lineolaris; Aleyrodidae such as
Trialeurodes vaporariorum, Bemisia tabaci, Dialeurodes citri, and Aleurocanthus spiniferus; Coccoidea such as
Aonidiella aurantii, Comstockaspis perniciosa, Unaspis citri, Ceroplastes rubens, Icerya purchasi, Planococcus kraunhiae, Pseudococcus longispinis, and Pseudaulacaspis pentagona; Tingidae; Cimicoidea such as Cimex lectularius; Psyllidae such as Cacopsylla pyricola; etc.
Lepidoptera :
Pyralidae such as Chilo suppressalis, Tryporyza incertulas, Cnaphalocrocis medinalis, Notarcha derogata , Plodia interpunctella , Ostrinia furnacalis, Hellula undalis, and Pediasia teterrellus; Noctuidae such as Spodoptera litura, Spodoptera exigua, Pseudaletia separata, Sesamia inferens, Mamestra brassicae, Agrotis ipsilon, Plusia nigrisigna, Trichoplusia ni, Thoricoplusia spp., Heliothis spp., and Helicoverpa spp.; Pieridae such as Pieris rapae; Tortricidae such as Adoxophyes spp., Grapholita molesta, Leguminivora glycinivorella , Matsumuraeses azukivora,
Adoxophyes orana fasciata, Adoxophyes honmai., Homona magnanima , Archips fuscocupreanus, and Cydia pomonella;
Gracillariidae such as Caloptilia theivora , and
Phyllonorycter ringoneella; Carposinidae such as Carposina niponensis; Lyonetiidae such as Lyonetia spp.; Lymantriidae such as Lymantria spp., and Euproctis spp.; Yponomeutidae such as Plutella xylostella ; Gelechiidae such as
Pectinophora gossypiella, and Phthorimaea operculella;
Arctiidae such as Hyphantria cunea; Tineidae such as Tinea translucens, and Tineola bisselliella; Tuta absoluta; etc.
Thysanoptera :
Thripidae such as Frankliniella occidentalis, Thrips parmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Frankliniella fusca, Stenchaetothrips biformis, Haplothrips aculeatus; etc.
Diptera :
Agromyzidae such as Hylemya antiqua, Hylemya platura,
Agromyza oryzae, Hydrellia griseola , Chlorops oryzae, andLiriomyza trifolii; Dacus cucurbitae, Ceratitis
capita ta ; etc.
Coleoptera :
Epilachna vigintioctopunctata , Aulacophora femoralis,
Phyllotreta striolata , Oulema oryzae, Echinocnemus squameus, Lissorhoptrus oryzophilus, Anthonomus grandis,
Callosobruchus chinensis, Sphenophorus venatus, Popillia japonica, Anomala cuprea, Diabrotica spp., Leptinotarsa decemlineata , Agriotes spp., Lasioderma serricorne; etc.
Orthoptera :
Gryllotalpa africana, Oxya yezoensis, Oxya japonica; etc .
[0038]
Among the above arthropod pests, Delphacidae,
Deltocephalidae, Aphididae, etc. are suitable for the present invention.
[0039]
The arthropod pest control composition of the present invention may be used for controlling plant diseases, for example, diseases caused by Rhizoctonia spp. or Fusarium spp. in corn, rice, soybean, cotton, rapeseed, or wheat.
[0040]
The arthropod pest control composition of the present invention can be used in agricultural lands such as fields, paddy fields, dry fields, lawns, and orchards or.
nonagricultural lands. The arthropod pest control
composition of the present invention can be also used for controlling pests in agricultural lands, etc. in which
"plants", etc. are grown.
[0041] Examples of plants to which the arthropod pest
control composition of the present invention can be applied include as described below:
[0042]
Crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugar cane, tobacco, etc.;
Vegetables: Solanaceae vegetables (eggplant, tomato, green pepper, hot pepper, potato, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Cruciferae vegetables (Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, cauliflower, rape, etc.), Compositae vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceae vegetables (Welsh onion, onion, garlic, asparagus, etc.), Umbelliferae vegetables (carrot, parsley, celery, parsnip, etc. ) , Chenopodiaceae vegetables (spinach, Swiss chard, etc.), Labiatae vegetables (Japanese basil, mint, basil, etc.), strawberry, sweat potato, yam, aroid, etc . ;
Fruit trees: pomaceous fruits (apple, common pear, Japanese pear, Chinese quince, quince, etc.), stone fleshy fruits (peach, plum, nectarine, Japanese plum, cherry, apricot, prune, etc.), citrus plants (Satsuma mandarin, orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazel nut, almond, pistachio, cashew nut, macadamia nut, etc.), berry fruits (blueberry, cranberry, blackberry, raspberry, etc.), grape, persimmon, olive, loquat, banana, coffee, date, coconut, oil palm, etc.;
Trees other than fruit trees: tea, mulberry,
flowering trees (azalea, camellia, hydrangea, sasanqua, Japanese star anise, cherry, tulip tree, crape myrtle, orange osmanthus, etc.), street trees (ash tree, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree, oak, poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanese arborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce, yew, spruce, elm, horse chestnut, etc. ) , coral tree, podocarpus, cedar, Japanese cypress, croton, Euonymus japonicus, Photinia glabra, etc.;
lawns: Zoysia ( zoysiagrass , Zoysia matrella, etc.), Bermuda grasses {Cynodon dactylon, etc.), bent grasses (Agrostis alba, creeping bent grass, hiland bent, etc.), blueglasses (meadow grass, bird grass, etc.), fescue (tall fescue, chewings fescue, creeping red fescue, etc.), ryegrasses (darnel, rye grass, etc.), orchard grass, timothy grass, etc.;
Others: flowers (rose, carnation, chrysanthemum, prairie gentian, gypsophila, gerbera, marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, convallaria, lavender, stock, ornamental cabbage, primula, poinsettia, gladiolus, cattleya, daisy, cymbidium, begonia, etc.), bio-fuel plants (Jatropha, safflower, camelina, switchgrass, Miscanthus, reed canary grass, giant reed, kenaf, cassava, willow, etc.),
ornamental plants, etc.
[0043]
Among the above plants, corn, rice, soybean, cotton, rapeseed, wheat, etc. are suitable for the present
invention .
[0044]
The "plants" as used herein may be those having resistance, which is imparted by a genetic engineering technique or a cross-breeding method.
[0045]
The arthropod pest control composition of the present invention can be applied to plants or area in which plants are grown for controlling arthropod pests therein. The plants as used herein include the stems and leaves of plants, the flowers of plants, the fruits of plants, the seeds of plants, and the bulbs of plants. The bulbs as used herein include scaly bulbs, corms, root stalks, tubers, tuberous roots, and rhizophores. [0046]
The method for controlling arthropod pests of the present invention comprises applying an effective amount of the arthropod pest control composition of the present invention to plants or area in which plants are grown.
The inventive method also includes embodiments in which the mesoionic compound and the disinfectant compound are applied separately or sequentially.
The "effective amount of the arthropod pest control composition" as used herein means the total amount of the mesoionic compound and the disinfectant compound, which is capable of exerting the controlling effect on an arthropod pest .
Examples of application methods include application to the stems and leaves of plants such as foliage
application; application to the seeds of plants; and application to area in which plants are grown such as soil application and submerged application.
[0047]
Specific examples of the application to the stems and leaves of plants such as foliage application in the present inevtnion include application to the surface of cultivated plants such as ground application by using manual sprayers, power sprayers, boom sprayers or Pancle sprayers, or aerial application or spraying by using radio control helicopters, etc .
[0048]
Specific examples of the application to the seeds of plants in the present inevtnion include the application of the arthropod pest control composition of the present invention to the seeds or bulbs of plants, more
specifically, for example, spray coating treatment on the surface of seeds or bulbs, dressing treatment on the seeds or bulbs of plants., immersion treatment, film coating treatment and pellet coating treatment.
[0049] Specific examples of the application to area in which plants are grown such as soil application and submerged application in the present inevtnion include planting hole treatment, plant foot treatment, planting furrow treatment, planting row treatment, broadcast treatment, side row treatment, seedling box treatment, seedbed treatment, mixing with culture soil, mixing with seedbed soil, mixing with a paste fertilizer, water surface treatment, etc.
[0050]
When the arthropod pest control composition of the present invention is applied to plants or area in which plants are grown, the application amount varies depending on the kinds of plants to be protected, the species or population size of arthropod pests to be controlled, the form of a formulation, the timing of application, weather conditions, etc., but is generally within a range from 0.05 to 10,000 g, preferably from 0.5 to 1,000 g per 1,000 m2 of an area where plants are grown, in terms of the total amount of the mesoionic compound and the disinfectant compound.
[0051]
When the arthropod pest control composition of the present invention is applied to the seeds of plants, the application amount varies depending on the kinds of plants to be protected, the species or population size of
arthropod pests to be controlled, the form of a formulation, the timing of application, weather conditions, etc., but is generally within a range from 0.001 to 100 g, preferably from 0.05 to 50 g per 1 kg of the seeds, in terms of the total amount of the mesoionic compound and the disinfectant compound .
[0052]
The arthropod pest control composition of the present invention is in the form of an emulsifiable concentrate, a wettable powder or a suspension concentrate are generally applied after dilution with water. In this case, the total concentration of the mesoionic compound and the disinfectant compound is generally 0.00001 to 10% by weight, preferably 0.0001 to 5% by weight. The arthropod pest control composition of the present invention in the form of a dust or a granule is generally applied as it is without dilution .
Examples
[0053]
Hereinafter, the present invention will be described in more detail with reference to Formulation Examples and Test Examples, but not limited thereto. In the Examples, the term "part(s)" means part(s) by weight unless otherwise specified, and "the mesoionic compound No. X" (e.g., "the mesoionic compound No. 4") refers to "compound No. X" (e.g., "compound No. 4") in Tables 1 to 3.
[0054]
Formulation Examples will be shown below.
[0055]
Formulation Example 1
Twenty parts of the mesoionic compound No. 4, 1 part of a disinfectant compound selected from Group (A) as described below and 35 parts of a mixture (weight ratio 1:1) of white carbon and ammonium polyoxyethylene
alkylether sulfate are mixed with water to a total amount of 100 parts, and then the mixture is finely-ground by a wet grinding method to obtain a suspension concentrate.
Group (A) : a group consisting of tebuconazole,
difenoconazole, triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazole M, cyproconazole, tetraconazole, ipconazole, triforine, pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate, triflumizole , azaconazole,
bitertanol, bromuconazole, epoxiconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, myclobutanil , penconazole, propiconazole, simeconazole and triadimefon .
[0056]
Formulation Example 2
The procedure as described in Formulation Example 1 is repeated, except that the mesoionic compound No. 5 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0057]
Formulation Example 3
The procedure as described in Formulation Example 1 is repeated, except that the mesoionic compound No. 42 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0058]
Formulation Example 4
The procedure as described in Formulation Example 1 is repeated, except that the mesoionic compound No. 44 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0059]
Formulation Example 5
The procedure as described in Formulation Example 1 is repeated, except that the mesoionic compound No. 1 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0060]
Formulation Example 6
Twenty parts of the mesoionic compound No. 4, 1 part of a disinfectant compound selected from Group (A) as described in Formulation Example 1, 1 part of metalaxyl, and 35 parts of a mixture (weight ratio 1:1) of white carbon and ammonium polyoxyethylene alkylether sulfate are mixed with water to a total amount of 100 parts, and then the mixture is finely-ground by a wet grinding method to obtain a suspension concentrate.
[0061] Formulation Example 7
The procedure as described in Formulation Example 6 is repeated, except that the mesoionic compound No. 5 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0062]
Formulation Example 8
The procedure as described in Formulation Example 6 is repeated, except that the mesoionic compound No. 42 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0063]
Formulation Example 9
The procedure as described in Formulation Example 6 is repeated, except that the mesoionic compound No. 44 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0064]
Formulation Example 10
The procedure as described in Formulation Example 6 is repeated, except that the mesoionic compound No. 1 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0065]
Formulation Example 11
Twenty parts of the mesoionic compound No. 4, 1 part of a disinfectant compound selected from Group (A) as described in Formulation Example 1, 0.5 parts of metalaxyl M, and 35 parts of a mixture (weight ratio 1:1) of white carbon and ammonium polyoxyethylene alkylether sulfate are mixed with water to a total amount of 100 parts, and then the mixture is finely-ground by a wet grinding method to obtain a suspension concentrate.
[0066]
Formulation Example 12
The procedure as described in Formulation Example 11 is repeated, except that the mesoionic compound No. 5 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0067]
Formulation Example 13
The procedure as described in Formulation Example 11 is repeated, except that the mesoionic compound No. 42 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0068]
Formulation Example 14
The procedure as described in Formulation Example 11 is repeated, except that the mesoionic compound No. 44 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0069]
Formulation Example 15
The procedure as described in Formulation Example 11 is repeated, except that the mesoionic compound No. 1 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0070]
Formulation Example 16
Ten parts of the mesoionic compound No. 4, 1 part of a disinfectant compound selected from Group (A) as
described in Formulation Example 1, 1.5 parts of sorbitan trioleate, and 28 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed, and then the mixture is finely-ground by a wet grinding method. To this mixture, an aqueous solution containing 0.05 parts of xanthane gum and 0.1 parts of magnesium aluminium silicate is added to a total amount of 90 parts, and then 10 parts of propylene glycol is added thereto. The resultant mixture is stirred to obtain a suspension concentrate.
[0071]
Formulation Example 17 The procedure as described in Formulation Example 16 is repeated, except that the mesoionic compound No. 5 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0072]
Formulation Example 18
The procedure as described in Formulation Example 16 is repeated, except that the mesoionic compound No. 42 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0073]
Formulation Example 19
The procedure as described in Formulation Example 16 is repeated, except that the mesoionic compound No. 44 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0074]
Formulation Example 20
The procedure as described in Formulation Example 16 is repeated, except that the mesoionic compound No. 1 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0075]
Formulation Example 21
Ten parts of the mesoionic compound No. 4, 1 part of a disinfectant compound selected from Group (A) as
described in Formulation Example 1, 1 part of metalaxyl, 1.5 parts of sorbitan trioleate, and 28 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed, and then the mixture is finely-ground by a wet grinding method. To this mixture, an aqueous solution containing 0.05 parts of xanthane gum and 0.1 parts of magnesium aluminium silicate is added to a total amount of 90 parts, and then 10 parts of propylene glycol is added thereto. The resultant mixture is stirred to obtain a suspension concentrate. [0076]
Formulation Example 22
The procedure as described in Formulation Example 21 is repeated, except that the mesoionic compound No. 5 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0077]
Formulation Example 23
The procedure as described in Formulation Example 21 is repeated, except that the mesoionic compound No. 42 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0078]
Formulation Example 24
The procedure as described in Formulation Example 21 is repeated, except that the mesoionic compound No. 44 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0079]
Formulation Example 25
The procedure as described in Formulation Example 21 is repeated, except that the mesoionic compound No. 1 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0080]
Formulation Example 26
Ten parts of the mesoionic compound No. 4, 1 part of a disinfectant compound selected from Group (A) as
described in Formulation Example 1, 0.5 parts of metalaxyl M, 1.5 parts of sorbitan trioleate, and 28 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed, and then the mixture is finely-ground by a wet grinding method. To this mixture, an aqueous solution containing 0.05 parts of xanthane gum and 0.1 parts of magnesium aluminium silicate is added to a total amount of 90 parts, and then 10 parts of propylene glycol is added thereto. The resultant mixture is stirred to obtain a suspension concentrate.
[0081]
Formulation Example 27
The procedure as described in Formulation Example 26 is repeated, except that the mesoionic compound No. 5 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0082]
Formulation Example 28
The procedure as described in Formulation Example 26 is repeated, except that the mesoionic compound No. 42 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0083]
Formulation Example 29
The procedure as described in Formulation Example 26 is repeated, except that the mesoionic compound No. 44 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0084]
Formulation Example 30
The procedure as described in Formulation Example 26 is repeated, except that the mesoionic compound No. 1 is employed instead of the mesoionic compound No. 4, to obtain a suspension concentrate.
[0085]
Formulation Example 31
Forty parts of the mesoionic compound No. 4, 1 part of a disinfectant compound selected from Group (A) as described in Formulation Example 1, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and the rest parts of synthetic hydrated silicon oxide are well mixed while grinding to obtain 100 parts of a wettable powder.
[0086] Formulation Example 32
The procedure as described in Formulation Example 31 is repeated, except that the mesoionic compound No. 5 is employed instead of the mesoionic compound No. 4, to obtain a wettable powder.
[0087]
Formulation Example 33
The procedure as described in Formulation Example 31 is repeated, except that the mesoionic compound No. 42 is employed instead of the mesoionic compound No. 4, to obtain a wettable powder.
[0088]
Formulation Example 34
The procedure as described in Formulation Example 31 is repeated, except that the mesoionic compound No. 44 is employed instead of the mesoionic compound No. 4, to obtain a wettable powder.
[0089]
Formulation Example 35
The procedure as described in Formulation Example 31 is repeated, except that the mesoionic compound No. 1 is employed instead of the mesoionic compound No. 4, to obtain a wettable powder.
[0090]
Formulation Example 36
Forty parts of the mesoionic compound No. 4, 1 part of a disinfectant compound selected from Group (A) as described in Formulation Example 1, 1 part of metalaxyl, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and the rest parts of synthetic hydrated silicon oxide are well mixed while grinding to obtain 100 parts of a wettable powder.
[0091]
Formulation Example 37
The procedure as described in Formulation Example 36 is repeated, except that the mesoionic compound No. 5 is employed instead of the mesoionic compound No. 4, to obtain a wettable powder.
[0092]
Formulation Example 38
The procedure as described in Formulation Example 36 is repeated, except that the mesoionic compound No. 42 is employed instead of the. mesoionic compound No. 4, to obtain a wettable powder.
[0093]
Formulation Example 39
The procedure as described in Formulation Example 36 is repeated, except that the mesoionic compound No. 44 is employed instead of the mesoionic compound No. 4, to obtain a wettable powder.
[0094]
Formulation Example 40
The procedure as described in Formulation Example 36 is repeated, except that the mesoionic compound No. 1 is employed instead of the mesoionic compound No. 4, to obtain a wettable powder.
[0095]
Formulation Example 41
Forty parts of the mesoionic compound No. 4, 1 part of a disinfectant compound selected from Group (A) as described in Formulation Example 1, 0.5 parts of metalaxyl
M, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and the rest parts of synthetic hydrated silicon oxide are well mixed while grinding to obtain 100 parts of a wettable powder.
[0096]
Formulation Example 42
The procedure as described in Formulation Example 41 is repeated, except that the mesoionic compound No . 5 is employed instead of the mesoionic compound No. 4, to obtain a wettable powder.
[0097] Formulation Example 43
The procedure as described in Formulation Example 41 is repeated, except that the mesoionic compound No. 42 is employed instead of the mesoionic compound No. 4, to obtain a wettable powder.
[00.98]
Formulation Example 44
The procedure as described in Formulation Example 41 is repeated, except that the mesoionic compound No. 44 is employed instead of the mesoionic compound No. 4, to obtain a wettable powder.
[0099]
Formulation Example 45
The procedure as described in Formulation Example 41 is repeated, except that the mesoionic compound No. 1 is employed instead of the mesoionic compound No. 4, to obtain a wettable powder.
[0100]
The effects of the present invention will be
demonstrated below with reference to Test Examples.
[0101]
Test Example 1
Each 10 mg of the mesoionic compounds Nos. 4, 5, 42 and 44, tebuconazole, difenoconazole, triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz and ipconazole was dissolved in 0.2 ml of a 5% (weight/volume ) solution of SORGEN TW-20 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in acetone (manufactured by Wako Pure Chemical Industries, Ltd.) and then diluted with water to given concentrations.
Each of the water dilutions of the mesoionic
compounds Nos. 4, 5, 42 and 44 was mixed with the water dilution of tebuconazole, difenoconazole, triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz or ipconazole to prepare a test solution.
The seedlings of rice {Oryza sativa; cultivar: Hoshinoyume) at the 1.5 leaf stage were immersed in each test solution. After that, the rice seedlings were air- died and put in plastic test tubes (diameter: 15 mm;
height: 100 mm) containing 1 ml of water. Then, 10 third- instar nymphs of Nilaparvata lugens were put in each test tube. The test tubes were placed in a room (25°C, humidity 55%). This is called a treated-section .
In the same manner as in the treated-section, the seedings of rice without any treatment with the test solutions were planted and grown, and then the insects were released. This is called an untreated-section.
Five (5) days after putting them, the tested nymphs were observed for life or death. From the observation results, an insect death rate was calculated by the following Equation 1) and a corrected insect death rate was calculated by the following Equation 2) . For each
treatment there were 2 replicates. The average values are shown in Tables 4 to 8.
[0102]
Equation 1); Insect death rate (%) = { (Number of tested insects - number of surviving insects ) /Number of tested insects} x 100
[0103]
Equation 2); Corrected insect death rate (%) = {(Insect death rate in treated section - Insect death rate in untreated section) /( 100 - Insect death rate in untreated section) } x 100
[0104]
Table 4
Tested compounds Application Corrected concentration insect death
[ppm] rate [%]
Mesoionic compound
+ + 100
Tebuconazole 0.1
Mesoionic compound No. 4 10
+ + 100
Tebuconazole 10
Mesoionic compound No. 4
+ + 100
Difenoconazole 0.1
Mesoionic compound No. 4 10
+ + 100
Difenoconazole 10
Mesoionic compound No. 4
+ + 100
Triticonazole
Mesoionic compound No. 4
+ + 100
Imazalil
Mesoionic compound No. 4
+ + 100
Triadimenol
Mesoionic compound No. 4
+ + 100
Fluquinconazole [0105]
Table 5
Tested compounds Application Corrected concentration insect death
[ppm] rate [%]
Mesoionic compound No. 4 10
+ + 100
Prochloraz 1
Mesoionic compound No. 4
+ + 100
Ipconazole
Mesoionic compound No. 5
+ + 100
Tebuconazole 0.1
Mesoionic compound 10
+ + 100
Tebuconazole 10
Mesoionic compound No. 5
+ + 100
Difenoconazole 0.1
Mesoionic compound No. 5 10
+ + 100
Difenoconazole 10
Mesoionic compound No. 5
+ + 100
Triticonazole
Mesoionic compound No. 5
+ + 100
Imazalil [0106]
Table 6
Tested compounds Application Corrected concentration insect death
[ppm] rate [%]
Mesoionic compound No. 5 10
+ + 100
Triadimenol
Mesoionic compound No. 5
+ + 100
Fluquinconazole
Mesoionic compound
+ + 100
Prochloraz
Mesoionic compound No. 5
+ + 100
Ipconazole
Mesoionic compound No. 42
+ + 100
Tebuconazole 0.1
Mesoionic compound No. 42 10
+ + 100
Tebuconazole 10
Mesoionic compound No.
+ + 100
Difenoconazole 0.1
Mesoionic compound No. 42 10
+ + 100
Difenoconazole 10 [0107]
Table 7
Tested compounds Application Corrected concentration insect death
[ppm] rate [%]
Mesoionic compound No.
+ + 100
Triticonazole
Mesoionic compound
+ + 100
Imazalil
Mesoionic compound No. 42
+ + 100
Triadimenol
Mesoionic compound No. 42
+ + 100
Fluquinconazole
Mesoionic compound
+ + 100
Prochloraz
Mesoionic compound 10
+ + 100
Ipconazole 1
Mesoionic compound No. 44
+ + 100
Tebuconazole 0.1
Mesoionic compound No. 10
+ + 100
Tebuconazole 10 [0108]
Table 8
Tested compounds Application Corrected concentration insect death
[ppm] rate [%]
Mesoionic compound No.
+ + 100
Difenoconazole 0.1
Mesoionic compound No. 10
+ + 100
Difenoconazole 10
Mesoionic compound No. 44
+ 100
Triticonazole
Mesoionic compound
+ + 100
Imazalil
Mesoionic compound No. 44
+ + 100
Triadimenol
Mesoionic compound No. 44
+ + 100
Fluquinconazole
Mesoionic compound No. 44
+ + 100
Prochloraz
Mesoionic compound No. 44
+ + 100
Ipconazole
[0109]
Test Example 2
Each 10 mg of the mesoionic compounds Nos. 4, and 44, tebuconazole, difenoconazole, triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, ipconazole and metalaxyl M was dissolved in 0.2 ml of a 5% (weight/volume) solution of SORGEN TW-20 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in acetone (manufactured by Wako Pure Chemical Industries, Ltd.) and then diluted with water to given concentrations.
Each of the water dilutions of the mesoionic
compounds Nos. 4, 5, 42 and 44 was mixed with the water dilution of tebuconazole, difenoconazole, triticonazole, imazalil, triadimenol, fluquinconazole , prochloraz or ipconazole, and the water dilution of metalaxyl M to prepare a test solution.
The seeds of rice ( Oryza sativa; cultivar:
Hoshinoyume) were treated with each test solution and then planted in plastic cups filled with soil. After 9 days from each treatment, the rice seeds were germinated and 10 third-instar nymphs of Nilaparvata lugens were released onto the rice seedlings. This is called a treated-section .
Specifically, the above treatment was performed as follows: The seeds of rice (Oryza sativa; cultivar:
Hoshinoyume) were put in 160-ml plastic cups' (diameter: 50 mm, height: 80 mm) and each test solution was added thereto at the rate of 1 ml per 100 seeds. Then, each cup was shaken by hand to apply the test solution to the seeds (dressing treatment) . On the same day, 10 treated seeds from each cup were planted in a 160-ml plastic cup
(diameter: 50 mm, height: 80 mm) with a lid, filled with a soil, and germinated with occasional sprinkling of water in a climate chamber at 30 °C and 65% relative humidity. After 9 days from each treatment, 10 third-instar nymphs of
Nilaparvata lugens were released onto the germinated rice in each cup, and the cup was placed in a room at 25°C and 55% relative humidity.
In the same manner as in the treated-section, the seeds of rice without any treatment with the test solutions were planted and grown, and then the insects were released. This is called an untreated-section. Six (6) days after releasing them, the tested nymphs were observed for life or death. From the observation results, an insect death rate was calculated by the following Equation 3) and a corrected insect death rate was calculated by the following Equation 4). For each
treatment there were 2 replicates. The average values are shown in Tables 9 to 16.
[0110]
Equation 3); Insect death rate (%) = {(Number of tested insects - number of surviving insects ) /Number of tested insects} x 100
[0111]
Equation 4); Corrected insect death rate (%) = {(Insect death rate in treated section - Insect death rate in untreated section) /( 100 - Insect death rate in untreated section) } x 100
[0112]
Table 9
Tested compounds Application Corrected amount insect death
[mg ai/seed] rate [%]
Mesoionic compound No. 4 0.05
+ + 100
Tebuconazole 0.0005
+ +
Metalaxyl M 0.0005
Mesoionic compound No. 4 0.05
+ + 100
Tebuconazole 0.05
Metalaxyl M 0.05
Mesoionic compound No. 4 0.05
+ + 100
Difenoconazole 0.0005
+ +
Metalaxyl M 0.0005
Mesoionic compound No. 4 0.05
+ + 100
Difenoconazole 0.05
+ +
Metalaxyl M 0.05
Mesoionic compound No. 4 0.05
+ + 100
Triticonazole 0.005
+ +
Metalaxyl M 0.005 [0113]
Table 10
Tested compounds Application Corrected amount insect death
[mg ai/seed] rate [%]
Mesoionic compound No. 4 0.05
+ + 100
Imazalil 0.005
+ +
Metalaxyl M 0.005
Mesoionic compound No. 4 0.05
+ + 100
Triadimenol 0.005
+ +
Metalaxyl M 0.005
Mesoionic compound No. 4 0.05
+ + 100
Fluquinconazole 0.005
Metalaxyl M 0.005
Mesoionic compound No. 4 0.05
+ + 100
Prochloraz 0.005
+ +
Metalaxyl M 0.005
Mesoionic compound No. 4 0.05
+ + 100
Ipconazole 0.005
+ +
Metalaxyl M 0.005 [0114]
Table 11
Tested compounds Application Corrected amount insect death
[mg ai/seed] rate [%]
Mesoionic compound No. 5 0.05
+ + 100
Tebuconazole 0.0005
+ +
Metalaxyl M 0.0005
Mesoionic compound No. 5 0.05
+ + 100
Tebuconazole 0.05
+ +
Metalaxyl M 0.05
Mesoionic compound No. 5 0.05
+ + 100
Difenoconazole 0.0005
+ +
Metalaxyl M 0.0005
Mesoionic compound No. 5 0.05
+ + 100
Difenoconazole 0.05
+ +
Metalaxyl M 0.05
Mesoionic compound No. 5 0.05
+ + 100
Triticonazole 0.005
+ +
Metalaxyl M 0.005 [0115]
Table 12
Tested compounds Application Corrected amount insect death
[mg ai/seed] rate [%]
Mesoionic compound No. 5 0.05
+ + 100
Imazalil 0.005
+ +
Metalaxyl M 0.005
Mesoionic compound No. 5 0.05
+ + 100
Triadimenol 0.005
+ +
Metalaxyl M 0.005
Mesoionic compound No. 5 0.05
+ + 100
Fluquinconazole 0.005
+ +
Metalaxyl M 0.005
Mesoionic compound No. 5 0.05
+ + 100
Prochloraz 0.005
+ +
Metalaxyl M 0.005
Mesoionic compound No. 5 0.05
+ + 100
Ipconazole 0.005
+ +
Metalaxyl M 0.005 [0116]
Table 13
Tested compounds Application Corrected amount insect death
[mg ai/seed] rate [%]
Mesoionic compound No. 42 0.05
+ + 100
Tebuconazole 0.0005
+ +
Metalaxyl M 0.0005
Mesoionic compound No. 42 0.05
+ + 100
Tebuconazole 0.05
+ +
Metalaxyl M 0.05
Mesoionic compound No. 42 0.05
+ + 100
Difenoconazole 0.0005
+ +
Metalaxyl M 0.0005
Mesoionic compound No. 42 0.05
+ + 100
Difenoconazole 0.05
+ +
Metalaxyl M 0.05
Mesoionic compound No. 42 0.05
+ + 100
Triticonazole 0.005
+ +
Metalaxyl M 0.005 [0117]
Table 14
Tested compounds Application Corrected amount insect death
[mg ai/seed] rate [%]
Mesoionic compound No. 42 0.05
+ + 100
Imazalil 0.005
+ +
Metalaxyl L 0.005
Mesoionic compound No. 42 0.05
+ + 100
Triadimenol 0.005
+ +
Metalaxyl M 0.005
Mesoionic compound No. 42 0.05
+ + 100
Fluquinconazole 0.005
+ +
Metalaxyl M 0.005
Mesoionic compound No. 42 0.05
+ + 100
Prochloraz 0.005
+ +
Metalaxyl M 0.005
Mesoionic compound No. 42 0.05
+ + 100
Ipconazole 0.005
+ +
Metalaxyl M 0.005 [0118]
Table 15
Tested compounds Application Corrected amount insect death
[mg ai/seed] rate [%]
Mesoionic compound No. 44 0.05
+ + 100
Tebuconazole 0.0005
+ +
Metalaxyl M 0.0005
Mesoionic compound No. 44 0.05
+ + 100
Tebuconazole 0.05
+ +
Metalaxyl M 0.05
Mesoionic compound No. 44 0.05
+ + 100
Difenoconazole 0.0005
+ +
Metalaxyl M 0.0005
Mesoionic compound No. 44 0.05
+ + 100
Difenoconazole 0.05
+ +
Metalaxyl M 0.05
Mesoionic compound No. 44 0.05
+ + 100
Triticonazole 0.005
+ +
Metalaxyl M 0.005 [0119]
Table 16
Tested compounds Application Corrected amount insect death
[mg ai/seed] rate [%]
Mesoionic compound No. 44 0.05
+ + 100
Imazalil 0.005
+ +
Metalaxyl M 0.005
Mesoionic compound No. 44 0.05
+ + 100
Triadimenol 0.005
+ +
Metalaxyl M 0.005
Mesoionic compound No. 44 0.05
+ + 100
Fluquinconazole 0.005
+ +
Metalaxyl M 0.005
Mesoionic compound No. 44 0.05
+ + 100
Prochloraz 0.005
+ +
Metalaxyl M 0.005
Mesoionic compound No. 44 0.05
+ + 100
Ipconazole 0.005
+ +
Metalaxyl M 0.005
In Tables 9 to 16, the term "mg ai/seed" means milligram compound per one seed applied in the test.
[0120]
Test Example 3 Each 10 mg of the mesoionic compound No. 1 and tebuconazole was dissolved in 0.2 ml of a 5% (weight/volume) solution of SORGEN TW-20 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in acetone (manufactured by Wako Pure Chemical Industries, Ltd.) and then diluted with water to given concentrations.
Each of the water dilutions of the mesoionic compound No. 1 was mixed with the water dilution of tebuconazole to prepare a test solution.
The seeds of rice {Oryza sativa; cultivar:
Hoshinoyume) were treated with each test solution and then planted in plastic cups filled with soil. After 10 days from each treatment, the rice seeds were germinated and 10 third-instar nymphs of Nilaparvata lugens were released onto the rice seedlings. This is called a treated-section .
Specifically, the above treatment was performed as follows: The seeds of rice (Oryza sativa; cultivar:
Hoshinoyume) were put in 160-ml plastic cups (diameter: 50 mm, height: 80 mm) and each test solution was added thereto at the rate of 1 ml per 100 seeds. Then, each cup was shaken by hand to apply the test solution to the seeds (dressing treatment) . On the same day, 10 treated seeds from each cup were planted in a 160-ml plastic cup
(diameter: 50 mm, height: 80 mm) with a lid, filled with a soil, and germinated with occasional sprinkling of water in a climate chamber at 30°C and 65% relative humidity. After 10 days from each treatment, 10 third-instar nymphs of Nilaparvata lugens were released onto the germinated rice in each cup, and the cup was placed in a room at 25 °C and 55% relative humidity.
In the same manner as in the treated-section, the seeds of rice without any treatment with the test solutions were planted and grown, and then the insects were released. This is called an untreated-section.
Six (6) days after releasing them, the tested nymphs were observed for life or death. From the observation results, an insect death rate was calculated by the following Equation 5) and a corrected insect death rate was calculated by the following Equation 6) . For each
treatment there were 2 replicates. The average values are shown in Table 17.
[0121]
Equation 5); Insect death rate (%) = {(Number of tested insects - number of surviving insects) /Number of tested insects} x 100
[0122]
Equation 6); Corrected insect death rate (%) = {(Insect death rate in treated section - Insect death rate in untreated section) /( 100 - Insect death rate in untreated section) } x 100
[0123]
Table 17
Figure imgf000052_0001
In Table 17, the term "mg ai/seed" means milligram compound per one seed applied in the test.
[0124]
Test Example 4
Each 10 mg of the mesoionic compounds Nos. 1, 4, 5, 42 and 44, prothioconazole, diniconazole, diniconazole M, cyproconazole and tetraconazole is dissolved in 0.2 ml of a 5% (weight/volume) solution of SORGEN TW-20 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) in acetone (manufactured by Wako Pure Chemical Industries, Ltd.) and then diluted with water to given concentrations when they are raw materials, or diluted with water to given concentrations when they are preparations.
Each of the water dilutions of the mesoionic
compounds Nos. 1, 4, 5, 42 and 44 is mixed with the water dilution of prothioconazole, diniconazole , diniconazole M, cyproconazole or tetraconazole, and the water dilution of metalaxyl M to prepare a test solution.
One soybean seed is spray-coated in a 15 ml
centrifuge tube with each test solution (5 μΐ) containing 2 mg of the mesoionic compound Nos. 1, 4, 5, 42 or 44, and 0.2 mg of prothioconazole, diniconazole, diniconazole M, cyproconazole or tetraconazole, and then the treated seed is planted in a 1/10, 000a Wagner pot filled with soil and grown in a greenhouse for 12 days. About 20 insects of Aulacorthum solani are released into each pot. This . is called a treated-section .
In the same manner as in the treated-section, one soybean seed without any treatment with the test solutions is planted and grown, and then the insects are released. This is called an untreated-section.
Six (6) days after releasing them, the number of
Aulacorthum solani is counted in the treated-section and the untreated-section, and a controlling value is
determined by the following equation. An insect death rate is calculated according to the following equation.
Controlling value (I) = {1 - (Cb x Tai)/(Cai x Tb) } x 100 wherein,
Cb: the number of insects in an untreated section before treatment
Cai: the number of insects in an untreated section on observation
Tb: the number of insects in a treated-section before treatment
Tai: the number of insects in a treated section on observation As a result, it is found that the controlling effect on arthropod pests obtained in a treated section is better than that obtained in an untreated section.

Claims

1. An arthropod pest control composition comprising a compound represented by formula (I):
Figure imgf000055_0001
wherein,
Q represents CR5=CR6, S, 0 or NCH3,
R1 represents a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group, an optionally halogenated C2-C4 alkenyl group, an optionally halogenated C2-C4 alkynyl group or an optionally halogenated C1-C4 alkoxy group,
n represents an integer of 0 to 3,
R2 re resents the following R2a, R2b, Rc or R2d:
Figure imgf000055_0002
wherein,
R3a, R3b and R3c each independently represent a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group, an optionally halogenated C2-C4 alkynyl group or an optionally halogenated C1-C4 alkoxy group,
R3d represents a halogen atom, cyano, nitro, an optionally halogenated C1-C4 alkyl group or an optionally halogenated C1-C4 alkoxy group,
Xa, Xb, Xc and Xd each independently represent 0, 1 or 2,
Zb and Zc each independently represent 0, S or NR7, R7 represents a hydrogen atom or an optionally halogenated C1-C4 alkyl group,
wherein,
when Xa represents 2, then two R3a's may be the same or different,
when Xb represents 2, then two R3b's may be the same or different,
when Xc represents 2, then two R3c,s may be the same or different, and
when Xd represents 2, then two R3d's may be the same or different,
R5 represents a hydrogen atom or a fluorine atom, and
R6 represents a hydrogen atom, a fluorine atom, a difluoromethyl group or a trifluoromethyl group,
wherein,
when n represents 2 or 3, then plural R11 s may be the same or different; and
at least one disinfectant compound selected from Group (A) ;
Group (A) : a group consisting of tebuconazole,
difenoconazole , triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazole , cyproconazole, tetraconazole, ipconazole, triforine, pyrifenox, fenarimol, nuarimol, oxpoconazole fumarate, pefurazoate, triflumi zole , azaconazole,
bitertanol, bromuconazole, epoxiconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, myclobutanil , penconazole, propiconazole, simeconazole and triadimefon .
2. The arthropod pest control composition according to claim 1, wherein the weight ratio of the compound
represented by formula (I) to the disinfectant compound is 10,000:1 to 0.01:1.
3. The arthropod pest control composition according to claim 1 or 2, wherein the disinfectant compound is
tebuconazole, difenoconazole, triticonazole, imazalil, triadimenol, fluquinconazole, prochloraz, prothioconazole, diniconazole, diniconazole M, cyproconazole , tetraconazole or ipconazole.
4. The arthropod pest control composition according to any of claims 1 to 3, wherein the composition further comprises metalaxyl or metalaxyl M.
5. The arthropod pest control composition according to claim 4, wherein the weight ratio of the compound
represented by formula (I) to metalaxyl or metalaxyl M is 10,000:1 to 0.01:1.
6. A method for controlling arthropod pests, which comprises applying an effective amount of the arthropod pest control composition according to any of claims 1 to 5 to plants or area in which plants are grown.
7. The method for controlling arthropod pests according to claim 6, wherein the plants or area in which plants are grown is the seeds of plants.
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US10759767B2 (en) 2012-12-20 2020-09-01 BASF Agro B.V. Compositions comprising a triazole compound
US10519122B2 (en) 2013-01-09 2019-12-31 BASF Agro B.V. Process for the preparation of substituted oxiranes and triazoles
US10981883B2 (en) 2013-01-09 2021-04-20 BASF Agro B.V. Process for the preparation of substituted oxiranes and triazoles
US10512267B2 (en) 2013-07-08 2019-12-24 BASF Agro, B.V. Compositions comprising a triazole compound and a biopesticide
JP2015031650A (en) * 2013-08-06 2015-02-16 株式会社 資生堂 Mass analytical method, ion generation device, and mass analytical system
EP3269245A1 (en) * 2014-06-25 2018-01-17 Basf Agro B.V. Arnhem (NL) Pesticidal compositions
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