KR101707262B1 - Stabilized aqueous suspended agricultural chemical composition - Google Patents

Abstract

The present invention relates to a process for the preparation of (a) an aqueous suspension tablet containing 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate as an active ingredient and (b) anionic surfactant or nonionic surfactant A composition for pesticides is provided. The composition for aqueous suspending pesticides is capable of inhibiting the hydrolysis of 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate, realizing redispersibility, Do.

Description

[0001] The present invention relates to a stabilized aqueous suspension agricultural chemical composition,

The present invention relates to an aqueous suspension-type pesticidal composition comprising 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate as an active ingredient.

Until now, emulsions and wettable powders have been known as agents for water dilution. However, large amounts of organic solvents are used in emulsions. Most of them are dangerous substances, and when used together, there is concern about odor and scattering of organic solvent. In addition, the wettable powders may be exposed to the user by the dusts when preparing the chemical liquid. For this reason, aqueous suspension formulations are required.

Preparations containing 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate (hereinafter sometimes referred to as "Compound A") useful as an agricultural chemical disinfectant include A disinfectant for water (rice straw) cultivated in a rice paddy field described in Patent Document 1 (Japanese Patent Application Laid-Open No. 2001-92231) and WO 2004/039156 (Patent Document 2), and a stabilizer prepared in Japanese Patent Laid-Open Publication No. 2009-155234 A solid preparation described in Patent Document 3) is known. However, the stabilized aqueous suspension tablet of Compound A is not specifically known until now.

Compound A has the same structure as Compound 2 described in Patent Document 2 and 4-acetoxy-6-tert-butyl-2,3-dimethyl-8-fluoroquinoline described in Patent Document 3.

Compound A was hydrolyzed with time in contact with water, so there was a problem in developing an aqueous suspension tablet formulation. In addition, there is a problem that the aqueous tabletting agent of the present invention does not maintain the suspension state by preservation and sinks, resulting in caking (caking). Therefore, it is required to prescribe a formulation of Compound A which solves this problem, is redispersible, and has excellent storage stability.

In order to improve the stabilization of the active ingredient in an aqueous suspension tablet formulation, the following documents are disclosed by the prior art. Regarding the blending of the pesticidal component and the surfactant, it is disclosed in Japanese Patent Application Laid-Open No. 2009-29773 (Patent Document 4) and Japanese Patent Laid-Open No. 2002-363005 (Patent Document 5). However, the pesticide ingredients described in Patent Documents 4 and 5 are compounds different from the compound A in structural and physical properties. Furthermore, Patent Documents 4 and 5 do not disclose whether or not any kind of surfactant can be combined with the pesticide ingredient when the pesticide ingredient is different from those described in Patent Documents 4 and 5.

Patent Document 1: WO 01/92231 Patent Document 2: WO 2004/039156 Patent Document 3: JP-A-2009-155234 Patent Document 4: Japanese Patent Laid-Open No. 2009-29773 Patent Document 5: Japanese Patent Laid-Open No. 2002-363005

The present inventors have now found that (a) an aqueous solution containing 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate as an active ingredient and (b) anionic surfactant or nonionic surfactant It has been found that the present composition for tabletop pesticides suppresses the hydrolysis of 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate to realize re-dispersibility and also has excellent storage stability. The present invention is based on the results of these studies.

Accordingly, an object of the present invention is to provide a water-soluble suspending pesticide which is capable of inhibiting the hydrolysis of 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl- And to provide a composition for use in the present invention.

According to an aspect of the present invention, there is provided a method of preparing a composition comprising (a) 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate as an active ingredient and (b) an anionic surfactant or non- There is provided an aqueous suspension composition for agricultural chemicals containing an active agent.

According to another aspect of the present invention, there is provided a process for producing a polyoxyethylene alkyl ether of (a) 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl- A polyoxyalkylene aryl phenyl ether-based anionic surfactant, or a nonionic surfactant.

According to another aspect of the present invention, there is provided a process for producing a polyoxyethylene alkyl ether of (a) 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl- A polyoxyalkylene aryl phenyl ether-based anionic surfactant or a nonionic surfactant and (c) tricalcium phosphate.

According to another aspect of the present invention, there is provided a process for preparing a polyoxyethylene alkyl ether of (a) 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl- A polyoxyalkylene aryl phenyl ether anionic surfactant or a nonionic surfactant and (c) tricalcium phosphate and having a pH of 5.5 to 9.0.

According to another aspect of the present invention, there is provided a method for producing a non-ionic surfactant, comprising: (a) mixing 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl- And (d) a compound having sterilization, insecticidal or herbicidal action in addition to the active agent as an active ingredient.

According to the present invention, there is provided an aqueous suspension composition for agricultural pesticides which is inhibited from hydrolysis of 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate and is redispersible and excellent in storage stability .

The content of the compound A in the composition of the present invention is not particularly limited, but is preferably a content of 1 to 50 parts by weight based on 100 parts by weight of the composition.

As the anionic surfactant and nonionic surfactant used in the aqueous suspension pesticidal composition of the present invention, anionic surfactants and nonionic surfactants conventionally used in aqueous suspension pesticide compositions may be used.

The anionic surfactant used in the aqueous suspension pesticide composition of the present invention is not particularly limited as far as the effect of the present invention is exerted. Examples of the anionic surfactant include ligninsulfonate, sodium naphthalenesulfonate formalin condensate, alkylnaphthalenesulfonic acid sodium formalin A condensate, at least one polyoxyethylene aryl phenyl ether sulfate selected from polyoxyethylene styryl phenyl ether sulfate and polyoxyethylene tristyryl phenyl ether sulfate, polyoxyalkylene aryl phenyl ether sulfate, polyoxyethylene styryl phenyl ether At least one polyoxyethylene aryl phenyl ether phosphate, polyoxyalkylene aryl phenyl ether phosphate or alkyl maleic acid copolymer selected from phosphate and polyoxyethylene tristyryl phenyl ether phosphate, and the like.

The nonionic surfactant used in the aqueous suspension pesticide composition of the present invention is not particularly limited as long as it exerts the effects of the present invention. For example, polyoxyalkylene aryl phenyl ether, polyethylene alkyl ether, polyoxyalkylene alkyl Ether or PO / EO block polymer.

The anionic surfactant and nonionic surfactant used in the aqueous suspension pesticide composition of the present invention are not particularly limited as long as the effect of the present invention is exerted, but preferred are polyoxyethylene arylphenyl ether-based or polyoxyalkylene aryl Phenyl ether surfactants, more preferably at least one polyoxyethylene aryl phenyl ether sulfate selected from polyoxyethylene styryl phenyl ether sulfate and polyoxyethylene tristyryl phenyl ether sulfate, polyoxyalkylene aryl phenyl ether Sulfates and polyoxyalkylene aryl phenyl ethers. More preferred are polyoxyethylene styrylphenyl ether sulfate or polyoxyalkylene arylphenyl ether sulfate, and more preferred are ammonium polyoxyethylene styrylphenyl ether sulfate and polyoxyalkylene arylphenyl ether sulfate.

The blending amount of the anionic surfactant or nonionic surfactant of the composition of the present invention is not particularly limited as long as the effect of the present invention is exhibited, but it is preferably 0.05 to 25 parts by weight based on 100 parts by weight of the composition.

When the composition of the present invention contains tricalcium phosphate, the compounding amount thereof is preferably 0.01 to 10 parts by weight based on 100 parts by weight of the composition, though it varies depending on the type of the surfactant to be used.

The composition of the present invention may contain auxiliaries for pesticides acceptable for pesticides, if necessary. Examples of the adjuvant for the formulation in this case include various auxiliaries described in, for example, "Pesticide Preparation Guide" (published by the Japanese Institute of Plant Protection, 1997). For the details, wetting agents include dioctylsulfo succinate, alkyl sulfate, POE alkyl ether, POE aryl ether, acetylenediol, PO / EO block polymer and the like. Examples of the thickening agent include organic thickening agents such as xanthan gum, polyvinyl pyrrolidone, polyvinyl alcohol, polyethylene glycol, methyl cellulose and alginic acid, and inorganic thickening agents such as bentonite. Examples of the cryoprotectant include polar solvents such as propylene glycol, ethylene glycol and glycerin. Examples of antifoaming agents include silicone emulsions, silicone oils, acetylenic diols, and PO / EO block polymers. Phosphates such as pH adjusters. In addition, fungicides and the like can be mentioned.

The pH value of the composition of the present invention is not particularly limited as long as the effect of the present invention is exerted, but the pH value is preferably 5.5 to 9.0, and more preferably 6.0 to 8.5. When the pH value of the composition of the present invention is in the above range, the hydrolysis of 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate can be further suppressed, A composition for a pesticide of the present invention can be provided.

The composition of the present invention can be prepared by various methods. A preferred production method is as follows. Compound A, a surfactant, a wetting agent, a cryoprotectant, a defoaming agent, and water are mixed with a stirrer to form a slurry state. This slurry is pulverized in a wet pulverizer to a predetermined particle size to obtain a pulverization slurry. A thickener, a fungicide, a pH adjuster and tricalcium phosphate are added to the pulverized slurry and stirred until uniform.

The composition of the present invention may contain, in addition to Compound A, at least one compound having a sterilizing, insecticidal or herbicidal action as an active ingredient, if necessary. The amount (effective amount) of the compound having a sterilizing, insecticidal or herbicidal action other than the compound A and the compound A is not particularly limited as long as it exerts the effect of the present invention. For example, 60 parts by weight, preferably 5 to 50 parts by weight.

The compounding ratio of the compound A with the compound having a sterilizing, insecticidal or herbicidal action is not particularly limited as long as the effect of the present invention is exerted. For example, it is in the range of 2:50 to 50: 2, preferably 1:10 to 10: 1.

Examples of the compound having sterilization, insecticidal or herbicidal action include, but are not limited to, the following.

Compounds having a bactericidal action include azoxystrobin, kresoxym-methyl, trifloxystrobin, orysastrobin, picoxystrobin, fluoxastrobin, fuoxastrobin, metominostrobin, mepanipyrim, pyrimethanil, cyprodinil, triadimefon, bitertanol, triflumizole (including but not limited to fuoxastrobin, metominostrobin, mepanipyrim, pyrimethanil, cyprodinil, triflumizole, propiconazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, prochloraz, shimeconazole, and the like. but are not limited to, for example, simeconazole, quinomethionate, maneb, zineb, mancozeb, polycarbamate, propineb, diethofencarb, Chlorothalonil, benomyl, Such as thiophanate-methyl, carbendazole, metalaxyl, oxadixyl, hydroxyisoxazole, fosetyl-aluminum, tocophor-methyl but are not limited to, tolclofos-methyl, captan, folpet, procymidone, iprodione, thifluzamide, furametpyr, flutolanil ), Mepronil, boscalid, penthiopyrad, fluopyram, fenpropimorph, dimethomorph, fludioxonil, fludioxonil, ), Enpiclonil, fthalide, probenazole, acibenzolar-S-methyl, tiadinil, isotianil, , Carpropamid, diclocymet, fenoxanil, tricyclazole, pyroquilon, and fimilone (f erynzone, fluazinam, cymoxanil, triforine, pyrifenox, fenarimol, fenpropidin, pencycuron siasopa, Cyazofamid, cyflufenamid, proquinazid, quinoxyfen, famoxadone, fenamidone, iprovalicarb, bennitrofen, But are not limited to, benthiavalicarb-isopropyl, fluopicolide, pyribencarb, streptomycin, kasugamycin or validamycin, and the like. .

Compounds having an insecticidal action include compounds such as acephate, dichlorvos, EPN, fenitothion, fenamifos, prothiofos, profenofos, Such as pyraclofos, chlorpyrifos-methyl, chlorfenvinphos, demeton, ethion, malathion, coumaphos, But are not limited to, isoxathion, fenthion, diazinon, thiodicarb, aldicarb, oxamyl propoxur, carbaryl, A fenobucarb, an ethiofencarb, a fenothiocarb, a pirimicarb, a carbofuran, a carbosulfan, a furathiocarb, a high quinacarb, but are not limited to, hyquincarb, alanycarb, methomyl, benfuracarb, cartap, thioc such as cyclodextrins, cyclodextrins, cyclodextrins, cyclodextrins, cyclodextrins, cyclodextrins, cyclodextrins, cyclodextrins, cyclodextrins, cyclodextrins, cyclodextrins, cyclodextrins, cyclodextrins, cyclodextrins, cyclodextrins, The compounds of the present invention may be used in combination with other drugs such as dimefluthrin, empenthrin, fenfluthrin, fenpropathrin, imiprothrin, metofluthrin, permethrin, But are not limited to, phenothrin, resmethrin, tefluthrin, tetramethrin, tralomethrin, transfluthrin, cypermethrin, deltamethrin, , Cyhalothrin, fenvalerate, fluvalinate, ethofenprox, flufenprox, halfenprox, silafluofen, and the like. , Cyromazine, diflubenzuron, teflubenzur (teflubenzuron) on, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, penfluron, triflumuron (see, for example, such as triflumuron, chlorfluazuron, diafenthiuron, methoprene, fenoxycarb, pyriproxyfen, halofenozide, tebufenozide, but are not limited to, tebufenozide, methoxyfenozide, chromafenozide, dicyclanil, buprofezin, hexythiazox, amitraz, The compounds of the present invention may be used in combination with chlordimeform, pyridaben, fenpyroxymate, flufenerim, pyrimidifen, tebufenpyrad, tolfenpyrad, Fluocrypyrim, acequinocyl, cyflumetofen, flu (< RTI ID = 0.0 > But are not limited to, flubendiamide, ethiprole, fipronil, ethoxazole, imidacloprid, nitenpyram, c1othianidin, acetamiprid, dinotefuran, thiacloprid, thiamethoxam, pymetrozine, bifenazate, spirodiclofen, spiromethophen, such as spiromesifen, flonicamid, chlorfenapyr, pyriproxyfene, indoxacarb, pyridalyl, spinosad, avermectin, But are not limited to, milbemycin, azadirachtin, nicotine, rotenone, BT, insect pathogenic virus, emamectin benzoate, spinetoram, Pyrazluquinazon, chlorantraniliprol (chlorantraniliprol) e), cyenopyrafen, spirotetramat, lepimectin, metaflumizone, pyrafluprole, pyriprole, dimplein dime fluthrin, fenazaflor, hydramethylnon, or triazamate.

As herbicidal compounds there may be mentioned mefenacet, daimuron, pentazone, prometryn, bensulfuron-methyl, pyrazosulfuron-ethyl, -ethyl, imazosulfuron, cyhalofop-butyl, oxaziclomefone, fentrazaide, clomeprop, anilofos, Benzoficyclon, cafenstrole, pentoxazone, indanofan, DCMU, linuron, or trifluralin, and the like can be mentioned.

According to a preferred feature of the present invention, there is provided a method for preparing a composition comprising (a) 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate as an active ingredient and (b) an anionic surfactant or a nonionic surfactant , And a compound having a sterilizing, insecticidal or herbicidal action.

According to another preferred characteristic of the present invention, in said combination, (a) 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate as an active ingredient and (b) anionic surfactant or An aqueous suspension pesticide composition containing a nonionic surfactant is provided as a first composition, and a compound having a sterilizing, insecticidal or herbicidal action provides a second composition containing it as an active ingredient. In this case, the second composition may be any formulation in combination with an appropriate carrier or adjuvant. The combination may be provided in the form of a pharmaceutical kit or the like.

According to another feature of the present invention, there is provided a method for preparing a composition comprising (a) 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate as an active ingredient and (b) an anionic surfactant or a nonionic surfactant (Preferably simultaneously) to an area to be treated with a compound having an antimicrobial, insecticidal or herbicidal action, both simultaneously and separately.

According to another aspect of the present invention, there is provided a method for protecting a useful plant from a pest, comprising the steps of: (a) mixing 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl- ) An aqueous suspending pesticide component containing an anionic surfactant or a nonionic surfactant and a method comprising a simultaneous or separate (preferably simultaneous) application of a compound having a sterilizing, insecticidal or herbicidal action to the area to be treated .

The simultaneous application in this process is carried out on an aqueous suspension tablet containing (a) 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate and (b) anionic surfactants or nonionic surfactants Pesticidal ingredients and compounds having a sterilizing, insecticidal or herbicidal action prior to application to the area to be treated and applying the mixture to the area to be treated. On the other hand, the application individually is carried out by using (a) 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate as an active ingredient and (b) anionic surfactant or nonionic surfactant (A) an effective amount of 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4 -Acetate and (b) an aqueous suspending pesticide component containing an anionic surfactant or a non-ionic surfactant is applied prior to the application of a compound having a sterilizing, insecticidal or herbicidal action, and (a) 6-tert -Butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate and (b) an aqueous suspending pesticide component containing an anionic surfactant or a nonionic surfactant, Applied after the application of Wu says.

According to another preferred feature of the present invention there is provided a method for protecting a useful plant from pests,

(1) an aqueous suspension tablet pesticide composition comprising (a) 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate and (b) an anionic surfactant or a non- The first composition comprising as an active ingredient

(2) applying a second composition comprising, as an active ingredient, a compound having a sterilizing, insecticidal or herbicidal action, to a region to be treated

In the case of using the composition or combination of the present invention, it is possible to perform operations such as spraying, injection, immersion and the like in an area to be treated with water or the like as needed. This work specifically includes, for example, application to useful plants itself (leaf spreading), application to the cultivation area of useful plants (soil, number of surface areas, seedling box, etc.).

According to another aspect of the present invention there is provided a method of protecting a useful plant from a pest, comprising applying an effective amount of a composition or combination according to the present invention to the area to be treated. The area to be treated herein refers to the area required to be treated using the composition according to the present invention for the protection of useful plants. For example, the useful plant itself, the cultivation area of useful plants (soil, Nursery boxes, etc.). Preferably, the area to be treated is the useful plant itself.

According to another aspect of the present invention there is provided the use of a composition or combination of the present invention for protecting a useful plant from pests.

The amount of the composition or the combination according to the present invention can be appropriately changed depending on the use environment, the growth condition of the plant to be treated, the mixing ratio of the active ingredient, the use time, the method of use, and the kind of disease to be controlled, The effective ingredient amount per 10 ares is 1 to 1,500 g, preferably 10 to 150 g. For example, when the composition or combination according to the present invention is applied to a rice plant, the amount of the composition or combination according to the present invention is 5 to 500 g, preferably 10 to 100 g, per 10 arcs of the ground.

According to a preferred feature of the present invention, there is provided a method for inhibiting the hydrolysis of 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate, a method for improving redispersibility, (B) an anionic surfactant or a nonionic surfactant is added to 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate as an active ingredient. .

According to a further preferred feature of the present invention there is provided a process for inhibiting the hydrolysis of 6-tert-butyl-2,3-dimethyl 8-fluoroquinolyl-4-acetate, a process for improving redispersibility, (B) an anionic surfactant or a nonionic surfactant and a phosphoric acid or a salt thereof. And adding a compound having sterilizing, insecticidal or herbicidal action to tricalcium and / or the active ingredient.

Examples and Comparative Examples will be specifically described below, but the present invention is not limited thereto.

Example

Manufacturing example

Compound A, a surfactant, a cryoprotectant, a defoaming agent, and a part of water were mixed with a stirrer according to the preparation (component and ratio) shown in Tables 1 and 2 below to form a slurry. When the particle size became 2 μm in a wet pulverizer . A thickener, tricalcium phosphate and the remainder of water were added to the pulverized slurry, and the mixture was stirred until it became homogeneous to prepare aqueous suspension pesticidal compositions of Examples 1 to 9 and Comparative Examples 1 to 7.

Example One 2 3 4 5 6 7 8 9 Compound A * 1 20.7 20.7 20.7 20.7 20.7 20.7 20.7 20.7 20.7 Sorpol T-20SPG * 2 5.0 5.0 Newkalgen FS-700SW * 3 5.0 5.0 Newkalgen FS-77PG * 4 5.0 5.0 Newkalgen CP-15-200 * 5 5.0 5.0 SOPROPHOR 4D384 * 6 5.0 Propylene glycol 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 Silicone defoamer 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 1% aqueous solution of xanthan gum 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 Tricalcium phosphate 1.0 1.0 1.0 1.0 1.0 water Balance Balance Balance Balance Balance Balance Balance Balance Balance Initial pH 4.8 6.4 5.2 6.4 5.4 6.6 4.9 6.0 4.7

(The numbers are expressed as weight%, water added to 100%). The initial pH indicates the pH before storage at 50 DEG C in the following examples.

Comparative Example One 2 3 4 5 6 7 Compound A * 1 20.7 20.7 20.7 20.7 20.7 20.7 20.7 SANX P-252 * 7 5.0 5.0 DEMOL EP Powder * 8 5.0 DEMOL N * 9 5.0 5.0 Morwet D-425 * 10 5.0 5.0 TAYCAPOWER BC2070M * 11 1.0 1.0 1.0 1.0 Propylene glycol 5.0 5.0 5.0 5.0 5.0 5.0 5.0 Silicone defoamer 0.5 0.5 0.5 0.5 0.5 0.5 0.5 1% aqueous solution of xanthan gum 10.0 10.0 10.0 10.0 10.0 10.0 10.0 Tricalcium phosphate 1.0 1.0 water Balance Balance Balance Balance Balance Balance Balance Initial pH 5.8 6.0 9.7 6.3 7.5 7.7 6.6

(The numbers are expressed as weight%, water added to 100%). The initial pH indicates the pH before storage at 50 DEG C in the following examples.

* 1: 6-tert-Butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate (purity: 96.83%

* 2: Polyoxyethylene (19) styrylphenyl ether ammonium sulfate ammonium propylene glycol: 20% (Toho Chemical Industry Co., Ltd.)

* 3: Polyoxyalkylene aryl phenyl ether sodium sulfate (Takemoto Oil & Fat Co., Ltd.)

* 4: Polyoxyethylene aryl phenyl ether sulfuric acid ammonium salt Propylene glycol (Takemoto Oil &

* 5: Polyoxyalkylene aryl phenyl ether (Takemoto Oil &

* 6: Polyoxyethylene (16) tristyryl phenyl ether ammonium sulfate (Rhodianica)

* 7: Sodium ligninsulfonate (Nippon Paper Chemicals, Inc.)

* 8: Alkyl maleic acid copolymer (Kao Corporation)

* 9: Condensation product of sodium naphthalenesulfonate formalin (Cao Corporation)

* 10: Alkylnaphthalenesulfonic acid sodium formalin condensate (Lion Muscle Co., Ltd.)

* 11: Calcium dodecylbenzenesulfonate (manufactured by Tai Ka Co., Ltd.)

Test Example

The aqueous suspension pesticidal compositions prepared in Examples 1 to 9 and Comparative Examples 1 to 7 were stored in 50 glass vials. After storage for a predetermined period, the content of Compound A was analyzed to calculate the decomposition rate from the initial content. The storage was started at 50 < 0 > C and the redispersibility after 2 months was evaluated. The test results are shown in Tables 3 and 4. In Table 3 and Table 4, "50 ° C × 1 month" and "50 ° C × 2 months" refer to samples stored at 50 ° C for 1 month and 2 months. When the measurement was not carried out, it was marked with "-".

HPLC  Analysis condition

Column: Inertsil ODS-2 (5, manufactured by GL Science), 4.6 mm in inner diameter 250 mm in length

Mobile phase: acetonitrile / water = 60/40 (V / V%)

Flow rate: 1.0 mL / min

Column temperature: 40 DEG C

Detection wavelength: 254 nm

Redistribution  Measuring conditions

The sample taken out from the thermostat at 50 DEG C was allowed to stand at room temperature and cooled naturally. The sample cooled to room temperature was transferred into the vial once per second. The redispersibility when the vial was conducted within 10 times and uniformly dispersed was evaluated as "○". The redispersibility in the case where the vial was not uniformly dispersed when it was conducted 10 times was evaluated as 'x'. If the measurement is impossible, it is marked with '-'.

Example One 2 3 4 5 6 7 8 9 After one month at 50 ° C
Decomposition rate (%) 0.3 0.0 0.8 0.0 8.4 1.0 4.5 0.7 12.2 50 ℃ × 2 months later
Decomposition rate (%) 4.3 3.0 8.5 0.1 24.1 3.4 17.2 3.3 13.5 50 ℃ × 2 months later
Redistribution ○ ○ ○ ○ ○ ○ ○ ○ ○

Comparative Example One 2 3 4 5 6 7 After one month at 50 ° C
Decomposition rate (%) 10.5 10.8 4.8 96.3 95.2 96.9 46.9 50 ℃ × 2 months later
Decomposition rate (%) - - - - - - - 50 ℃ × 2 months later
Redistribution ×
integrity ×
integrity ×
Cohesion

From the above results, it was proved that the addition of the anionic surfactant or the nonionic surfactant improves the storage stability of the aqueous suspension composition of Compound A, i.e., inhibits the hydrolysis of Compound A and redisperses the composition. In addition, it has been proved that addition of tricalcium phosphate to the composition can further improve storage stability.

Claims (5)

(a) 6-tert-butyl-2,3-dimethyl-8-fluoroquinolyl-4-acetate as an active ingredient, (b) anionic surfactant or nonionic surfactant, wherein the anionic surfactant or non- Wherein the water-insoluble surfactant is a polyoxyalkylene aryl phenyl ether surfactant, and (c) the water-soluble surfactant comprises tricalcium phosphate. delete delete The composition according to claim 1, wherein the composition has a pH of 5.5 to 9.0. 5. The composition according to claim 1 or 4, wherein the composition further comprises (d) a compound having sterilizing, insecticidal or herbicidal action as an active ingredient.