JP5360349B2 - Stabilized aqueous suspension pesticide composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an aqueous suspended agrochemical composition in which the decomposition of its agrochemical active ingredient is suppressed. <P>SOLUTION: The aqueous suspended agrochemical composition comprises a specific agrochemical active ingredient and an alkyl polyglycoside. A method for suppressing the decomposition of the above active ingredient in the above composition, characterized by using a combination of the specific agrochemical active ingredient and the alkyl polyglycoside is also provided. The above active ingredient is preferably pyrazosulfuron-ethyl, halosulfuron-methyl or azimsulfuron. <P>COPYRIGHT: (C)2009,JPO&amp;INPIT

Description

  The present invention relates to an aqueous suspension pesticide composition in which degradation of an agrochemical active ingredient is suppressed and a method for inhibiting degradation of the agrochemical active ingredient.

Agrochemical active ingredients selected from the compounds represented by the following formula (1) and their salts are known to exhibit extremely high herbicidal activity, but tend to be relatively easily hydrolyzed in water. In the suspended pesticide composition, the pesticidal active ingredient is significantly degraded during storage. Therefore, a method for suppressing the decomposition of the pesticidal active ingredient is desired. Up to now, as a method for suppressing the decomposition of a sulfonylurea compound which is one of the pesticidal active ingredients, a method of adding a water-soluble carboxylate or inorganic acid salt (Patent Document 1) or an aqueous suspension pesticide composition A method of making the pH of an object 6 or less (Patent Document 2) is known.
JP 59-205305 A Japanese Patent Laid-Open No. 05-105606

  The subject of this invention is providing the aqueous | water-based suspended agricultural chemical composition in which decomposition | disassembly of the agricultural chemical active ingredient chosen from the compound represented by Formula (1) and those salts is suppressed.

  As a result of intensive studies, the present inventors have used alkyl polyglycosides as surfactants in aqueous suspension pesticide compositions of agrochemical active ingredients selected from the compounds represented by formula (1) and their salts. Thus, it was found that the decomposition of the pesticidal active ingredient can be remarkably suppressed.

  That is, the present invention provides an aqueous suspension agricultural chemical composition (hereinafter referred to as the present invention composition) described in [1] to [10] and a method for inhibiting decomposition of an agricultural chemical active ingredient described in [11] below (hereinafter referred to as “the present invention composition”). , Referred to as the method of the present invention).

  [1] Formula (1):

[Where,
G represents G1, G2, G3, G4, G5, G6, G7, G8, G9, G10 or CH ₃ (CH ₃ SO ₂ ) N;
L represents L1 or L2,
X and Y each independently represent a hydrogen atom, a halogen atom, a _C1-3 alkyl group or a _C1-3 alkoxy group.
Z represents CH or a nitrogen atom
L1 represents SO ₂ NH (C = O) N (R ¹ ), CH ₂ SO ₂ NH (C = O) N (R ¹ ) or NHSO ₂ NH (C = O) N (R ¹ )
L2 represents an oxygen atom, a sulfur atom, CH ₂ , CH (OH) or C═O,
R ¹ represents a hydrogen atom or a C _1-3 alkyl group,
G1, G2, G3, G4, G5, G6, G7, G8, G9 and G10 are

Represents
R ² represents a C _1-3 alkyl group, a C _1-3 alkoxy C _1-3 alkyl group, a phenyl group optionally substituted by A, or a pyridyl group optionally substituted by A;
A represents one or more substituents selected from a halogen atom, a _C1-3 alkyl group, a _C1-3 alkoxy group and a _C1-3 haloalkyl group;
R ³ is a hydrogen atom, a halogen atom, a C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _1-6 haloalkyl group, a C _2-6 haloalkenyl group, a C _2-6 halo. alkynyl group, C _{1 to 6} haloalkoxy group, C _{1 to 3} alkoxy C _{1 to 6} alkyl groups, C _{1 to 3} haloalkoxy C _{1 to 3} alkyl ^{_{groups, NO 2, CO 2 R 8}} , COR 9, CON (R _{^{10) 2, CONHR 10, NHCOR}} 9, SO 2 R 11, SO 2 N (R 10) 2, SO 2 NH (R 10), NHSO 2 (R 11), CH (CHFCH 3) (OCOCH 2 OCH 3) Represents a 2-methyl-2H-tetrazol-5-yl group or Q;
Q is

Represents
R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, a halogen atom, a C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _1-6 haloalkyl group, C _2-6 haloalkenyl group, C _2-6 haloalkynyl group, C _1-3 alkoxy C _1-3 alkyl group, NHCOR ⁹ , CH ₂ NHSO ₂ R ¹¹ , C (R ¹² ) = NOR ¹³ or 4,6 Represents -dimethoxypyrimidin-2-yl group
When R ³ and R ⁴ are adjacent to each other, R ³ and R ⁴ may form a 5- or 6-membered ring with the carbon atoms to which they are bonded, and include an oxygen atom or a carbonyl group in the formed ring. Well,
R ⁸ is a hydrogen atom, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _3-6 cycloalkyl group, 3-oxetanyl group, 2-oxetanyl Group, or N = C (Ph) ₂
R ⁹ represents a hydrogen atom, a C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _1-6 haloalkyl group or a C _3-6 cycloalkyl group,
R ¹⁰ represents a C _1-6 alkyl group,
R ¹¹ represents a C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group or a C _1-6 haloalkyl group,
R ¹² represents a hydrogen atom or a C _1-6 alkyl group,
R ¹³ represents a C _1-6 alkyl group,
Represents
R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ each independently represent a hydrogen atom or a C _1-6 alkyl group. An aqueous suspension pesticide composition comprising one or more pesticidal active ingredients selected from the compounds represented by the formula (I) and salts thereof and an alkylpolyglycoside.

  [2] An aqueous suspended pesticidal composition comprising one or more pesticidal active ingredients selected from the compounds according to [1] above, wherein L is L1, and salts thereof, and an alkylpolyglycoside.

  [3] An aqueous suspended pesticidal composition comprising one or more pesticidal active ingredients selected from the compounds according to the above [1] and salts thereof, wherein L is L2, and an alkylpolyglycoside.

  [4] An aqueous suspended pesticidal composition comprising one or more pesticidal active ingredients selected from the compounds according to [1] above, wherein L is L1, and G is G1, and salts thereof, and an alkylpolyglycoside.

  [5] An aqueous solution containing one or more pesticidal active ingredients selected from the compounds according to the above [1], wherein L is L1, and G is G4, G5, G7, G8 or G9 and an alkyl polyglycoside Suspended agricultural chemical composition.

[6] One or more pesticidal active ingredients selected from the compounds according to [1] above, wherein L is L1, G is G1, and R ³ is CO ₂ R ⁸ and salts thereof, and an alkylpolyglycoside An aqueous suspension pesticide composition.

[7] An aqueous suspension comprising one or more pesticidal active ingredients selected from the compounds according to [1] above, wherein L is L1, G is G1, and R ³ is Q, and salts thereof, and an alkylpolyglycoside. Turbid pesticide composition.

  [8] The aqueous suspended pesticidal composition according to the above [4], wherein the pesticidal active ingredient is pyrazosulfuron ethyl, halosulfuron methyl or azimusulfuron.

  [9] The aqueous suspended agricultural chemical composition according to any one of the above [1] to [8], wherein the pH is less than 6.

  [10] The aqueous suspended agricultural chemical composition according to any one of [1] to [9], further comprising a salt.

  [11] An aqueous suspension pesticide composition characterized by using one or more pesticidal active ingredients selected from the compounds represented by formula (1) and salts thereof described in [1] above and an alkylpolyglycoside in combination. Method for inhibiting decomposition of active ingredient of agricultural chemical contained in food.

  The composition of the present invention is excellent in storage stability in an aqueous suspension composition of an agrochemical active ingredient selected from the compound represented by the formula (1) and salts thereof.

  Specific examples of the pesticidal active ingredient selected from the compound represented by the formula (1) of the present invention and salts thereof include azimsulfuron, amidosulfuron, and iodosulfuron-methyl. ), Imazosulfuron, ethametsulfuron-methyl, ethoxysulfuron, oxasulfuron, orthosulfamuron, chlorimuron-ethyl, chlor Sulfuron (chlorsulfuron), cyclosulfamuron (cyclosulfamuron), cinosulfuron (sulfosulfuron), sulfometuron-methyl (sulfometuron-methyl), thifensulfuron-methyl (thifensulfuron-methyl), triasulfuron (triasulfuron) ), Tritosulfuron (tritosu) lfuron), triflusulfuron-methyl, trifloxysulfuron, tribenuron-methyl, nicosulfuron, halosulfuron-methyl, pyrazosulfuron -Ethyl (pyrazosulfuron-ethyl), foramsulfron (flamsulfron), flazasulfuron (primisulfuron-methyl), flucetosulfuron (flucetosulfuron), flupirsulfuron-methyl (flupyrsulfuron), pros Lusulfuron (prosulfuron), bensulfuron-methyl, mesosulfuron-methyl, metsulfuron-methyl, rimsulfuron, 2-chloro-N- (4,6- Dimethoxypyrimidin-2-ylcarbamoyl) -7-propylimidazo [1,2-b] pyrida Gin-3-sulfonamide, 3-chloro-N- (4,6-dimethoxypyrimidin-2-ylcarbamoyl) -1-methyl-4- (5-methyl-5,6-dihydro-1,4,2- Dioxazin-3-yl) -1H-pyrazole-5-sulfonamide, 3-chloro-N- (4,6-dimethoxypyrimidin-2-ylcarbamoyl) -1-methyl-4- (6-methyl-5,6 -Dihydro-1,4,2-dioxazin-3-yl) -1H-pyrazol-5-sulfonamide, 3-chloro-4- (5,6-dihydro-1,4,2-dioxazin-3-yl) -N- (4,6-dimethoxypyrimidin-2-ylcarbamoyl) -1-methyl-1H-pyrazol-5-sulfonamide, N- (4,6-dimethoxypyrimidin-2-ylcarbamoyl) -1-methyl- 4- (5-Methyl-5,6-dihydro-1,4,2-dioxazin-3-yl) -1H-pyrazol-5-sulfonamide, N- (4,6-dimethoxypyrimidin-2-ylcarbamoyl) -1-methyl-4- (6-methyl-5,6-dihydro-1,4,2-dioxazin-3-yl) -1H-pyrazole-5-sulfur 4-amide, 4- (5,6-dihydro-1,4,2-dioxazin-3-yl) -N- (4,6-dimethoxypyrimidin-2-ylcarbamoyl) -1-methyl-1H-pyrazole-5- Sulfonamide, N- (4,6-dimethoxypyrimidin-2-ylcarbamoyl) -1,3-dimethyl-4- (5-methyl-5,6-dihydro-1,4,2-dioxazin-3-yl) -1H-pyrazol-5-sulfonamide, 4- (5,6-dihydro-1,4,2-dioxazin-3-yl) -N- (4,6-dimethoxypyrimidin-2-ylcarbamoyl) -1, 3-dimethyl-1H-pyrazole-5-sulfonamide, bispyribac, pyrithiobac, pyriftalid, pyribenzoxim, pyrimisulfan, pyriminobac-methyl, monosulfuron (Monosulfuron) and monosulfuron-methyl.

  The content of the pesticidal active ingredient selected from the compounds represented by the formula (1) of the present invention and salts thereof is usually 0.001 to 50 parts by weight, more preferably 0, per 100 parts by weight of the composition of the present invention. 0.001 to 10 parts by weight, more preferably 0.001 to 5 parts by weight, and still more preferably 0.001 to 3 parts by weight.

  The pesticidal active ingredient of the present invention is further added to one or more known pesticides such as herbicides, insecticides, acaricides, nematicides, antiviral agents, plant growth regulators, fungicides, synergists, An attractant and repellent can also be used in combination, and in this case, a more excellent effect may be exhibited. Specific examples of known agrochemicals are as follows, but are not limited to these.

  Herbicides: esprocarb, benthiocarb, molinate, dimepiperate, pyributicarb, mefenacet, butachlor, pretilachlor, tenylchlor, thenylchlor bromobutide, etobenzanid, dymron, cumyluron, bentazone, bentazone salt, 2,4-D, 2,4-D salt, 2,4-D ester, MCP, MCP salt, MCP ester, MCPB, MCPB salt, MCPB ester, phenothiol (MCPA-thioethyl), clomeprop, naproanilide, oxadiazon, pyrazolate, pyrazoxifene en), benzofenap, oxadiargyl, dimethametryn, simethrin, piperophos, anilofos, butamifos, bensulide, dithiopyr, dithiopyr CNP, chloromethoxynil, cyhalofop butyl, bifenox, caffenstrole, pentoxazone, indanofan, oxaziclomefone, fentrazamide, butenachlor , ACN, benzobicyclon, benfuresate, cymmethylin, simazine, diclolobenil, diuron, chloro IPC ( chlorpropham, atrazine, alachlor, isouron, chlorphtalim, cylanazin, trifluralin, butamifos, propyzamide, promethrin, pen Pendimethalin, metolachlor, metribuzin, linuron, lenacil, propanil, MCPA, ioxynil octanoate, ashram, kizarohop ethyl ( quizalofop-ethyl, propaquizafop, quizalofop-tefuryl, sethoxydim, fenoxaprop-ethyl, phenmedipham, fluazihop butyl ( fluazifop-butyl), Bentazone, SAP (bensulide), TCTP (chlorthal-dimethyl, tetorachlorothiophene), amiprophosmethyl, amethrin, isoxaben, orthobencarb (orbencarb), tefuryltrione , Karbutilate, dithiopyr, siduron, thiazafluron, napropamide, prodiamine, pyraclonil, besefine, methyl dymron, 2 , 4-PA, MCPPA, imazaquin, imazapyr, tetrapropion (flupropanate), tebuthiuron, bromacil, hexazinone, glyphosate-ammonium, glyphosate-toy Glyphosate-iso-propylammonium, glyphosate-trimesium, glyphosate-sodium, glyphosate-potassium, bialaphos, glufosinate-ammonium ), MCC, mesotrione, penoxsulam, aminopyralid, bencarbazone, pinoxaden, propoxycarbazone sodium salt (propoxycarbazone-sodium), pyrasulfotole, pyroxasulfone (Pyroxasulfone), pyroxsulam, tembotrione, thiencarbazone-methyl, topramezon.

  Fungicide: acibenzolar, ampropyfos, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl, Benzamacril, binapacryl, biphenyl, bitertanol, bethoxazine, bordeaux mixture, blasticidin-S, bromoconazole, buprimate (Bupirimate), buthiobate, calcium polysulfide, captafol, captan, copper oxychloride, carpropamid, carbendazim, calb Xin (carboxin), chinomethionat, clobenthiazone, chlorfenazol, chloroneb, chlorothalonil, clothalinil, cufraneb, simoxanil, cymoxanil Proconazole, cyprodinil, cyprofuram, debacarb, dichlorophen, dichlorobutrazol, diclhlofluanid, diclomedine, diclomedine, dicloran Diethofencarb, dicrocymet, difenoconazole, diflumetorim, dimethirimol, dimethomorph, diniconazole ( diniconazole), dinicoazole-M (diniconazole-M), dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazolonone ), Edifenphos, epoxiconazole, etaconazole, etirimol, etridiazole, famoxadone, fenarimol, febuconazole, fenam (fenam) , Fenpiclonil, fenpropidin, fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxo Fludioxonil, fluoroimide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminum ( fosetyl-aluminium, fuberidazole, fluralaxyl, fenamidone, fenhexamid, guazatine, hexachlorobenzene, hexaconazole, hymexazol, Imazalil, imibenconazole, iminoctadine, ipconazole, iprobenfos, iprodione, isoprothiolane, Iprovalicarb, kasugamycin, kresoxim-methyl, mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metalaxyl Metconazole, metiram, metinominostrobin, microbutanil, nabam, nickel bis (dimethyldithiocarbamate), nitrothal-isopropyl , Nuarimol, octhilinone, offurace, oxadixyl, oxycarboxin, oxpoconazole fumarate, pefurzoate, pen Penconazole, penencycuron, phthalide, piperalin, polyoxins, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propamocarb hydrochloride, propicocarb hydrochloride Propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quinoxyfen, quintozene, sulfur, spiroxamine ), Tebuconazole, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram ), Tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, triridemorph, triflumizole, triflumizole Triforine, triticonazole, validamycin, vinclozolin, zineb, ziram, oxine-copper.

  Bactericides: streptomycin, oxyterracycline, oxolinic acid.

  Nematicides: aldoxycarb, fosthiazate, fosthietan, oxamyl, fenamiphos.

  Acaricides: cyenopyrafen, acrylonitrile compounds such as cyfulmetofen, spiromesifen, spirodiclofen, pyridaben, amitraz, bromopropylate, Chinomethionat, chlorobezilate, clofentezine, cyhexatine, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide oxide, fenpropathrin, fenproximate, halfenprox, hexythiazox, milbemectin, propargite ( propargite), pyrimidifen, tebufenpyrad.

  Insecticides: abamectin, acephate, acetamipirid, azinphos-methyl, bendiocarb, benfuracarb, bensultap, bifenthrin, prof ), Butocarboxim, carbaryl, carbfuran, carbofuran, carbosulfan, cartap, chlorfenapyr, chlorpyrifos, chlorfenvinphos, chlor Flufluron (chlorfluazuron), clothianidin (clothianidin), chromafenozide (chromafenozide), chlorpyrifos-methyl (chlorpyrifos-methyl), cyfluthrin (cyfluthrin), beta-cyfluthrin (beta-cyfluthrin) Methperin (cypermethrin), cyromazine, cyhalothrin, lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diacloden, diflubenzuron ), Dimethylvinphos, diofenolan, disulfoton, dimethoate, EPN, esfenvalerate, ethiofencarb, ethiprole, etofenprox, Etrimfos, fenitrothion, fenobucarb, phenoxy curve, fenpropathrin, fenvalerate, fiproni (Fipronil), flucythrinate, flufenoxuron, flufenprox, tau-fluvalinate, fonophos, formetanate, formothion ), Furathiocarb, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathione isoxathion, lufenuron, malathion, metaldehyde, metamidophos, methidathion, methacrifos, metalcarb, methomyl yl), metoprene, methoxychlor, methoxyfenozide, monocrotophos, muscalure, nitenpyram, omethoate, oxydemeton-methyl, oxdemeton-methyl (Oxamyl), parathion, parathion-methyl, permethrin, phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidone ( phosphamidon, pirimicarb, pirimiphos-methyl, profenofos, pymetrozine, pyraclofos, pyriproxyfen, rotenone, sulprofo (Sulprofos), silafluofen, spinosad, sulfotep, sulfotep, tebfenozide, teflubenzuron, teflubenzuron, tebuthorin, terbufos, tetrachlorovinphos (tetrachlorvinphos) ), Thiamethoxam, thiofanox, thiometon, tolfenpyrad, tralomethrin, trichlorfon, triazuron, triflumuron, bamidion, etc. can give.

  These pesticidal active ingredients can be used alone or in admixture of two or more, and the ratio in the case of mixing can be freely selected. Although the total content of the pesticidal active ingredient in the composition of the present invention can be appropriately selected, a range of 0.001 to 50 parts by weight is preferable with respect to 100 parts by weight of the composition of the present invention.

The alkylpolyglycoside used in the present invention has the formula (2):
R ²⁰ O (R ²¹ O) _b (G11) _a (2)
[Where,
R ²⁰ represents a C _6-30 alkyl group, a C _6-30 alkenyl group, a C _6-30 alkynyl group or a C _6-30 alkylphenyl group,
R ²¹ represents a C _2-4 alkylene chain,
G11 represents 5 monosaccharide residues or 6 monosaccharide residues,
b represents a number from 0 to 12,
a represents a numerical value of 1 to 10. ] Is represented.

Preferred alkyl polyglycosides are:
An alkylpolyglycoside in which G11 is a glucose residue and b is 0 in formula (2);
An alkylpolyglycoside in which R ²⁰ is a C _6-30 alkyl group or a C _6-30 alkenyl group in formula (2);
In the formula (2), R ²⁰ is an alkyl group having a chain length of C ₆ , C ₈ , C ₁₀ , C ₁₂ , C ₁₄ , C ₁₆ or C ₁₈ , or C ₆ , C ₈ , C ₁₀ , C ₁₂ , Alkyl polyglycosides that are alkenyl groups having a chain length of C ₁₄ , C ₁₆ or C ₁₈ , and alkyl polyglycosides consisting of mixtures thereof,
In formula (2), an alkylpolyglycoside in which (G11) _a is an average of 1 to 10 sugar residues bonded to each other by _a glycosidic bond,
In the formula (2), (G11) _a may be composed of sugar residues of different types of reducing sugars, the alkyl polyglycoside whose sugar residue is glucose or maltose, and in the formula (2): A representing the number of sugar residues is a statistical average based on typical distributions, particularly suitable include an average of 1 to 5 sugar molecules per alkyl group, more preferably 1 to 5 In particular, the average degree of polymerization of the glycoside residues of at least one alkyl polyglycoside is from about 1 to about 1.8, and of these surfactants, more preferably C _6-14 Examples include alkyl polyglycosides having an alkyl group with a chain length.
The content of the alkylpolyglycoside in the composition of the present invention can be appropriately selected, and is usually 0.1 to 20 parts by weight, more preferably 0.1 to 10 parts by weight, more preferably 100 parts by weight of the composition of the present invention. Preferably it is 0.1-5 weight part.
In the composition of the present invention, a surfactant other than the alkylpolyglycoside can be added as necessary. Examples of these surfactants include the following (A), (B), (C), (D) and (E).

(A) Nonionic surfactant:
(A-1) Polyethylene glycol type surfactant: For example, polyoxyethylene alkyl (C _8-18 ) ether, ethylene oxide adduct of alkyl naphthol, polyoxyethylene (mono or di) alkyl (C _8-12 ) phenyl Ether, formalin condensate of polyoxyethylene (mono or di) alkyl ( _C8-12 ) phenyl ether, polyoxyethylene (mono, di or tri) phenyl phenyl ether, polyoxyethylene (mono, di or tri) benzyl phenyl Ether, polyoxypropylene (mono, di or tri) benzyl phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxypropylene (mono, di or tri) styryl phenyl ether, polyoxyethylene (Mono-, di- or tri-) styryl phenyl ether polymer, alkyl (C _{8 to 18)} polyoxyethylene polyoxypropylene block polymer ethers, alkyl (C _{8 to 12)} polyoxyethylene polyoxypropylene block polymer ether, polyoxy Ethylene bisphenyl ether, polyoxyethylene resin acid ester, polyoxyethylene fatty acid (C _8-18 ) monoester, polyoxyethylene fatty acid (C _8-18 ) diester, polyoxyethylene sorbitan fatty acid (C _8-18 ) ester, glycerol fatty acid ester ethylene oxide adduct, castor oil ethylene oxide adduct, hydrogenated castor oil ethylene oxide adduct, alkyl (C _{8 to 18)} amine ethylene oxide adduct and lipid Acid _{(C 8 to 18)} amide ethylene oxide adducts.

(A-2) Polyhydric alcohol type surfactant: For example, glycerol fatty acid ester, polyglycerin fatty acid ester, pentaerythritol fatty acid ester, sorbitol fatty acid (C _8-18 ) ester, sorbitan fatty acid (C _8-18 ) ester, Examples thereof include sugar fatty acid esters, polyhydric alcohol alkyl ethers, and fatty acid alkanolamides.

  (A-3) Acetylene-based surfactant: Examples thereof include acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene oxide adduct of acetylene alcohol, and the like.

(B) Anionic surfactant:
(B-1) Carboxylic acid type surfactant: For example, polyacrylic acid, polymethacrylic acid, polymaleic acid, polymaleic anhydride, maleic acid or maleic anhydride and olefin (for example, isobutylene and diisobutylene) Polymer, Copolymer of acrylic acid and itaconic acid, Copolymer of methacrylic acid and itaconic acid, Copolymer of maleic acid or maleic anhydride and styrene, Copolymer of acrylic acid and methacrylic acid, Acrylic acid Copolymer of acrylic acid and methyl ester of acrylic acid, copolymer of acrylic acid and vinyl acetate, copolymer of acrylic acid and maleic acid or maleic anhydride, N-methyl-fatty acid ( _C8-18 ) sarcosinate, resin _Examples thereof include carboxylic acids such as acids and fatty acids (C _8-18 ), and salts of these carboxylic acids.

(B-2) sulfate surfactants: for example, alkyl _{(C 8 to 18)} sulfates, polyoxyethylene alkyl _{(C 8 to 18)} ether sulfuric acid ester, polyoxyethylene (mono or di) alkyl _{(C 8 -12} ) phenyl ether sulfate, polyoxyethylene (mono or di) alkyl ( _C8-12 ) phenyl ether polymer sulfate, polyoxyethylene (mono, di or tri) phenyl phenyl ether sulfate, polyoxyethylene (Mono, di or tri) benzyl phenyl ether sulfate, polyoxyethylene (mono, di or tri) styryl phenyl ether sulfate, polyoxyethylene (mono, di or tri) styryl phenyl ether polymer sulfate, polyoxyethylene Down sulfate ester polyoxypropylene block polymers, sulfated oils, fatty acid ester sulfuric, sulfate ester such as sulfated fatty acid and sulfated olefin, and salts of these sulfuric esters.

(B-3) Sulfonic acid type surfactant: For example, paraffin ( _C8-22 ) sulfonic acid, alkyl ( _C8-12 ) benzenesulfonic acid, alkyl ( _C8-12 ) benzenesulfonic acid formalin condensate, Formalin condensate of cresol sulfonic acid, α-olefin (C _8-16 ) sulfonic acid, dialkyl (C _8-12 ) sulfosuccinic acid, polyoxyethylene (mono or di) alkyl (C _8-12 ) phenyl ether sulfonic acid, Polyoxyethylene alkyl (C _8-18 ) ether sulfosuccinic acid half ester, naphthalene sulfonic acid, (mono or di) alkyl (C _1-6 ) naphthalene sulfonic acid, formalin condensate of naphthalene sulfonic acid, (mono or di) alkyl _{(C 1 to 6)} formalin condensates of naphthalenesulfonic acid, Formalin condensate of Reosoto oil sulfonic acid, alkyl (C _{8 to 12)} ether disulfonic acid, Igepon T (trade name), polystyrene sulfonic acid and styrene sulfonic acid and methacrylic acid copolymer of acrylic acid, and their sulfone Examples include acid salts.

(B-4) Phosphate ester type surfactants: For example, alkyl (C _8-12 ) phosphate ester, polyoxyethylene alkyl (C _8-18 ) ether phosphate ester, polyoxyethylene (mono or di) alkyl (C _{8 -12} ) phenyl ether phosphate ester, polyoxyethylene (mono, di or tri) alkyl ( _C8-12 ) phenyl ether polymer phosphate ester, polyoxyethylene (mono, di or tri) phenyl phenyl ether phosphate ester, poly Oxyethylene (mono, di or tri) benzyl phenyl ether phosphate ester, polyoxyethylene (mono, di or tri) styryl phenyl ether phosphate ester, polyoxyethylene (mono, di or tri) styryl phenyl ether polymer phosphate ester, Polyoxye Examples thereof include phosphate esters of a tylene polyoxypropylene block polymer, phosphate esters such as phosphatidylcholine, phosphatidylethanolimine and condensed phosphoric acid (for example, tripolyphosphoric acid), and salts of these phosphate esters.

  Examples of the salt in the above (B-1) to (B-4) include alkali metals (lithium, sodium, potassium, etc.), alkaline earth metals (calcium, magnesium, etc.), ammonium and various amines (for example, alkylamine, cyclohexane). Alkylamine and alkanolamine).

(C) Cationic surfactant:
Examples thereof include alkylamines, alkyl quaternary ammonium salts, alkylamine ethylene oxide adducts, and alkyl quaternary ammonium salt ethylene oxide adducts.

(D) Amphoteric surfactant:
Examples thereof include betaine type surfactants and amino acid type surfactants.

(E) Other surfactants:
For example, silicone surfactants and fluorine surfactants can be used.

  Surfactants other than these alkylpolyglycosides can be used alone or in admixture of two or more, and the ratio in the case of mixing can also be freely selected. Although content of this surfactant in this invention composition can be selected suitably, the range of 0.1-20 weight part is preferable with respect to 100 weight part of this invention composition.

  Various adjuvants can be further contained in the composition of the present invention. Examples of auxiliary agents that can be used include thickeners, organic solvents, antifreezing agents, antifoaming agents, antibacterial and antifungal agents, coloring agents, and the like.

  The thickening agent is not particularly limited, and organic, inorganic natural products, synthetic products and semi-synthetic products can be used. For example, heteropolysaccharides such as xanthan gum (xanthan gum), welan gum and rhamzan gum, polyvinyl alcohol, polyvinyl Water-soluble polymer compounds such as pyrrolidone, polyacrylic acid, sodium polyacrylate and polyacrylamide, cellulose derivatives such as methylcellulose, carboxymethylcellulose, carboxyethylcellulose, hydroxyethylcellulose and hydroxypropylcellulose, montmorillonite, saponite, hectorite, bentonite and laponite And smectite clay minerals such as synthetic smectites. These thickeners may be used alone or in combination of two or more, and the ratio in the case of mixing can be freely selected. These thickeners may be added as they are, or those previously dispersed in water may be added. Moreover, content in this invention composition can also be selected freely.

Examples of the organic solvent include alcohols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol and isopropanol, ethers such as butyl cellosolve, ketones such as cyclohexanone, esters such as γ-butyrolactone, N-methylpyrrolidone and N - acid amides such as octyl pyrrolidone, polar solvent, xylene, alkyl (C ₉ or C _10, etc.) benzene, phenylxylylethane and alkyl (C ₁ or C _3, etc.) aromatic hydrocarbons such as naphthalene and the like, Machine oil, aliphatic hydrocarbons such as normal paraffin, isoparaffin and naphthene, mixtures of aromatic and aliphatic hydrocarbons such as kerosene, soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil and castor oil Fats and oils, etc. Polar solvent, and the like.

  As the antifreezing agent, for example, ethylene glycol, diethylene glycol, propylene glycol, glycerin and the like can be used. Preferred are propylene glycol and glycerin. Moreover, content in this invention composition can also be selected freely.

Further, an antifoaming agent such as a silicone emulsion, an antibacterial and antifungal agent, a coloring agent, and the like may be blended.
The production method of the composition of the present invention is not particularly limited, and can be obtained by adding each of the aforementioned components to water and mixing with a stirrer. If necessary, the pesticidal active ingredient, surfactant and other adjuvants may be singly or mixed and finely pulverized by a dry type and wet type pulverizer.

Dry pulverization can be performed with an impact pulverizer, a ball mill, a jet mill or the like. The fine pulverization by wet pulverization can be performed by a wet pulverizer such as an attritor, a sand grinder, a dyno mill, a pearl mill, an apex mill, a visco mill, and an ultra visco mill.
The composition of the present invention preferably has a pH of less than 6 and more preferably a pH of 5 or less in order to further suppress the decomposition of the compound represented by formula (1) and salts thereof. More preferably, the pH is 4 or less.

  The method for controlling the pH of the composition of the present invention is not particularly limited. Examples of the pH control agent include various inorganic acids and organic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, sulfonic acid and carboxylic acid, and salts and esters thereof. The method of adding predetermined amount to a composition is mentioned. Specific examples of the organic acid include acidic phosphate, citric acid, maleic acid, sorbic acid, lactic acid, and tartaric acid. Various buffer solutions such as disodium hydrogen phosphate-citric acid aqueous solution, sodium acetate-hydrochloric acid aqueous solution, formic acid-sodium formate aqueous solution, lactic acid-sodium lactate aqueous solution, tartaric acid-sodium tartrate aqueous solution and sodium citrate-hydrochloric acid aqueous solution are also provided. A pH can be controlled by adding a fixed amount.

  The composition of the present invention may further contain a salt in order to stabilize the suspended state and to suppress further decomposition of the compound represented by the formula (1) and a salt thereof.

  The salt used in the present invention is not particularly limited, and examples thereof include alkali metal salts (such as lithium, sodium and potassium), alkalis of various inorganic acids and organic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, carbonic acid, sulfonic acid and carboxylic acid. Examples include earth metal salts (such as calcium and magnesium), ammonium and various amine salts (such as alkylamine, cycloalkylamine, and alkanolamine). Preferred salts are those of hydrochloric acid, sulfuric acid and phosphoric acid. More preferred salts are alkali metal salts of hydrochloric acid, sulfuric acid and phosphoric acid. The addition amount of the salt is desirably less than the water solubility of the salt, but is usually 0.1 to 30 parts by weight, preferably 1 to 20 parts by weight, more preferably 3 to 100 parts by weight of the composition of the present invention. 20 parts by weight.

  Controlling the pH to less than 6 and adding a salt can each suppress the decomposition of the compound represented by the formula (1) and the salt thereof, but a more preferred embodiment is that the pH is 6 In addition to making it less than, adding the above-mentioned salt.

  The aqueous suspension pesticide composition of the present invention is, for example, a method of spraying directly on a paddy field as a stock solution, diluting about 50 to 5000 times with water, and using a sprayer or the like to harmful plants or the soil where it grows. Harmful plants can be controlled by applying by a method of spraying, or using a helicopter or the like from the air in a raw solution or a method of spraying after diluting 2 to 100 times with water. Examples of harmful plants include, for example, Inobie, Tainubie, Agaricus, Enokorogusa, Akinoenokorogusa, Oshiba, Oats, Oats, Sorghum, Shibamugi, Velvet Millet, Paragrass, Azegaya, Itozega, Suzumenotago, Hamanegusa, Azalea Weeping weeds such as firefly, Weeping weeping weeds such as Cyperus weeds such as firefly, Weeping weeping weeping, Weeping weeds such as Urikawa, Omodaka and Heramoda In addition to weeds, Ichibi, Maruagaagao, Shiroza, American golden-toothed deer, Siberian bluefish, Aobiyu, Aogateto, Ebisugusa, Ai Houzuki, Sanaetade, chickweed, cocklebur, Cardamine flexuosa, henbit, ragweed, cleavers, field bindweed, Datura, Ezo Roh fox thistle, and the like Enokigusa.

  EXAMPLES Next, although an Example is given and this invention is demonstrated further in detail, this invention is not limited to these. In the following, “pH” is a value measured with the composition stock solution, and “Compound 1” is 3-chloro-N- (4,6-dimethoxypyrimidin-2-ylcarbamoyl) -1-methyl-4- (5-methyl-5,6-dihydro-1,4,2-dioxazin-3-yl) -1H-pyrazole-5-sulfonamide. In addition, Compound 1 contains 3-chloro-N- (4,6-dimethoxypyrimidin-2-ylcarbamoyl) -1-methyl-4- (6-methyl-5,6-dihydro-1,4,2 as an impurity. -Dioxazin-3-yl) -1H-pyrazole-5-sulfonamide is contained 1.0%.

Examples 1 to 39
The constituent components shown in Tables 1 to 11 were uniformly mixed and wet pulverized to obtain the aqueous suspended agricultural chemical composition of the present invention. However, in Example 39 shown in Table 11, first, dimetamethrin was dissolved in the vinylizer 20 to prepare a solution, and then this solution and other components were uniformly mixed and wet pulverized to obtain the aqueous suspension of the present invention. A turbid pesticide composition was obtained.

[Comparative Examples 1 to 13]
The constituent components shown in Tables 12 to 15 were uniformly mixed and wet pulverized to obtain an aqueous suspended agricultural chemical composition.

[Test example]
The compositions obtained in Examples 1 to 23 and Comparative Examples 1 to 4 were stored in a thermostat at 40 ° C. for 3 months. The compositions obtained in Examples 24 to 38 and Comparative Examples 5 to 13 were stored in a thermostatic chamber at 54 ° C. for 2 weeks. The composition obtained in Example 39 was stored in a thermostatic oven at 40 ° C. for 1 month. The amount of the pesticidal active ingredient in the composition before and after storage was measured by HPLC, and the degradation rate was calculated by the following formula. The results are shown in Tables 1 to 15.

Degradation rate (%) = [(Amount of active ingredient before storage−Amount of agrochemical active ingredient after storage) /
(Agrochemical active ingredient amount before storage)] × 100

  The composition of the present invention can be used for controlling weeds.

Claims (7)

Formula (1):

[Where,
G represents G1,
L represents L1,
X and Y each independently represent a hydrogen atom, a halogen atom, a _C1-3 alkyl group or a _C1-3 alkoxy group.
Z represents CH or a nitrogen atom
L1 represents SO ₂ NH (C = O) N (R ¹ ), CH ₂ SO ₂ NH (C = O) N (R ¹ ) or NHSO ₂ NH (C = O) N (R ¹ )
R ¹ represents a hydrogen atom or a C _1-3 alkyl group,
G1

Represents
R ² represents a C _1-3 alkyl group, a C _1-3 alkoxy C _1-3 alkyl group, a phenyl group optionally substituted by A, or a pyridyl group optionally substituted by A;
A represents one or more substituents selected from a halogen atom, a _C1-3 alkyl group, a _C1-3 alkoxy group and a _C1-3 haloalkyl group;
R ³ is a hydrogen atom, a halogen atom, a C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _1-6 haloalkyl group, a C _2-6 haloalkenyl group, a C _2-6 halo. alkynyl group, C _{1 to 6} haloalkoxy group, C _{1 to 3} alkoxy C _{1 to 6} alkyl groups, C _{1 to 3} haloalkoxy C _{1 to 3} alkyl ^{_{groups, NO 2, CO 2 R 8}} , COR 9, CON (R _{^{10) 2, CONHR 10, NHCOR}} 9, SO 2 R 11, SO 2 N (R 10) 2, SO 2 NH (R 10), NHSO 2 (R 11), CH (CHFCH 3) (OCOCH 2 OCH 3) Represents a 2-methyl-2H-tetrazol-5-yl group or Q;
Q is

Represents
R ⁴ is a hydrogen atom, a halogen atom, a C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _1-6 haloalkyl group, a C _2-6 haloalkenyl group, a C _2-6 halo. Alkynyl group, C _1-3 alkoxy C _1-3 alkyl group, NHCOR ⁹ , CH ₂ NHSO ₂ R ¹¹ , C (R ¹² ) = NOR ¹³ or 4,6-dimethoxypyrimidin-2-yl group
When R ³ and R ⁴ are adjacent to each other, R ³ and R ⁴ may form a 5- or 6-membered ring with the carbon atoms to which they are bonded, and include an oxygen atom or a carbonyl group in the formed ring. Well,
R ⁸ is a hydrogen atom, C _1-6 alkyl group, C _2-6 alkenyl group, C _2-6 alkynyl group, C _1-6 haloalkyl group, C _3-6 cycloalkyl group, 3-oxetanyl group, 2-oxetanyl Group, or N = C (Ph) ₂
R ⁹ represents a hydrogen atom, a C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _1-6 haloalkyl group or a C _3-6 cycloalkyl group,
R ¹⁰ represents a C _1-6 alkyl group,
R ¹¹ represents a C _1-6 alkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group or a C _1-6 haloalkyl group,
R ¹² represents a hydrogen atom or a C _1-6 alkyl group,
R ¹³ represents a C _1-6 alkyl group ,
R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ each independently represent a hydrogen atom or a C _1-6 alkyl group. A compound represented by] and with one or more pesticidal active ingredient selected from the salts thereof, a pesticidal composition containing an alkyl polyglycoside, pH of the aqueous pesticidal composition 5 An aqueous suspension pesticide composition which is: The aqueous suspended agricultural chemical composition comprising at least one agricultural chemical active ingredient selected from the compounds according to claim 1 and salts thereof, wherein R ³ is CO ₂ R ⁸ , and an alkyl polyglycoside. The aqueous suspended pesticidal composition comprising at least one pesticidal active ingredient selected from the compounds according to claim 1, wherein R ³ is Q, and salts thereof, and an alkylpolyglycoside.   The aqueous suspension agricultural chemical composition according to claim 1, wherein the agricultural chemical active ingredient is pyrazosulfuron ethyl, halosulfuron methyl, or azimusulfuron.   The aqueous suspension pesticide composition according to any one of claims 1 to 4, wherein the pH of the aqueous suspension pesticide composition is 4 or less.   The aqueous suspended agricultural chemical composition according to any one of claims 1 to 5, further comprising a salt. In the aqueous suspension agricultural chemical composition, at least one agricultural chemical active ingredient selected from the compound represented by the formula (1) according to claim 1 and salts thereof and an alkylpolyglycoside are used in combination. A method for inhibiting degradation of the pesticidal active ingredient contained in an aqueous suspended pesticidal composition, wherein the pH of the suspended pesticidal composition is 5 or less.