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WO2008013249A1 - Pesticide emulsifiable concentrate - Google Patents

Pesticide emulsifiable concentrate Download PDF

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Publication number
WO2008013249A1
WO2008013249A1 PCT/JP2007/064725 JP2007064725W WO2008013249A1 WO 2008013249 A1 WO2008013249 A1 WO 2008013249A1 JP 2007064725 W JP2007064725 W JP 2007064725W WO 2008013249 A1 WO2008013249 A1 WO 2008013249A1
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Prior art keywords
weight
parts
emulsifiable concentrate
organic solvent
present
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PCT/JP2007/064725
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French (fr)
Inventor
Yumiko Kozuki
Kazuyuki Yanagisawa
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles

Definitions

  • the present invention relates to a pesticide emulsifiable concentrate which contains
  • 2- [ (2-fluoro-5-trifluoromethyl) phenylthio] -2- [3- (2-methoxyp henyl) -2-thiazolydinyliden] acetonitrile (hereafter referred to as the present acetonitrile compound) is an active ingredient of an agricultural or horticultural fungicide in US 6,710,062 Bl.
  • a pesticide emulsifiable concentrate containing the present acetonitrile compound as a pesticidal active ingredient is described in US 6,710,062 Bl.
  • the object of the present invention is to provide a pesticide emulsifiable concentrate containing the present acetonitrile compound as a pesticidal active ingredient, which is excellent in storage stability and is also excellent in emulsion stability when diluted with water.
  • a pesticide emulsifiable concentrate which contains the present acetonitrile compound, a hydrophobic organic solvent containing diethyl oxalate, a hydrophilic organic solvent and a surfactant, wherein the weight ratio of diethyl oxalate to the hydrophilic organic solvent falls within a range from 3:7 to 9:1, is less likely to be separated into two layers when it absorbs moisture and is also excellent in emulsion stability when diluted with water, and thus the present invention has been made.
  • a pesticide emulsifiable concentrate comprising 2- [ (2-fluoro-5-trifluoromethyl)phenylthio]-2-[3- (2-methoxyp henyl) -2-thiazolydinyliden] acetonitrile, a hydrophobic organic solvent containing diethyl oxalate, a hydrophilic organic solvent and a surfactant, wherein the weight ratio of diethyl oxalate to the hydrophilic organic solvent is in a range from 3:7 to 9:1.
  • hydrophilic organic solvent is at least one kind of an organic solvent selected from the group consisting of N, N-dimethyl acetamide, N,N-dimethyl propionamide, N,N-dimethyl formamide, N-methyl pyrrolidone,
  • N-ethyl pyrrolidone 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide.
  • the present acetonitrile compound contained in the pesticide emulsifiable concentrate of the present invention is a compound represented by the following formula (1) :
  • the present acetonitrile compound can be produced by a method described in US 6,710,062 Bl.
  • the amount of the present acetonitrile compound contained in the pesticide emulsifiable concentrate of the present invention is generally in a range from 1 to 10% by weight based on the total amount of the pesticide emulsifiable concentrate of the present invention.
  • the hydrophobic organic solvent containing diethyl oxalate (hereafter referredto as the present hydrophobic organic solvent) inthepesticide emulsifiable concentrate ofthepresent inventionmeans a hydrophobic organic solvent containing diethyl oxalate in an amount of 35 to 100% by weight . That is, the present hydrophobic organic solvent may be diethyl oxalate itself, or a mixture of diethyl oxalate and one or more other hydrophobic organic solvents other than diethyl oxalate, and also the content of diethyl oxalate is 35% by weight or more based on the total amount of the present hydrophobic organic solvent.
  • the content of diethyl oxalate of the present hydrophobic organic solvent is from 40 to 100% by weight .
  • the amount of the present hydrophobic organic solvent is generally in a range from 10 to 80% by weight, and preferably from 20 to 80% by weight, based on the total amount of the pesticide emulsifiable concentrate of the present invention.
  • the amount of diethyl oxalate is generally in a range from 5 to 80% by weight, preferably from 10 to 80% by weight, and more preferably from 20 to 80% by weight, based on the total amount of the pesticide emulsifiable concentrate of the present invention.
  • the weight ratio of diethyl oxalate to the hydrophilic organic solvent contained in the pesticide emulsifiable concentrate of the present invention is in a range from 3:7 to 9:1, and preferably from 4:6 to 8:2.
  • the present hydrophobic organic solvent can contain other hydrophobic organic solvents other than diethyl oxalate (hereafter referred to as the other hydrophobic organic solvent) .
  • Examples of another hydrophobic organic solvent includes aromatic hydrocarbons such as alkylbenzene (for example, xylene, tetramethylbenzene and the like) , alkylnaphthalene (for example, methylnaphthalene) , diphenylethane, dixylylethane, phenylxylylethane and the like; fatty acid monoesters such as methyl laurate, isopropyl myristate, isopropyl palmitate, methyl caprate, methyl oleate, isobutyl oleate, butyl propionate, isoamyl propionate, ethyl butyrate, butyl butyrate, isoamyl butyrate, isoamyl valerate, amyl lactate, methyl linoleate, methyl linolenate, palm fatty acidmethyl and the like; aliphatic hydrocarbons such as cyclohexane.
  • Preferable examples of another hydrophobic organic solvent includes aromatic hydrocarbons .
  • Commercially available products such as Hisol SAS-296 (commercial name of Nippon Oil Corp., a mixture of 1-phenyl-l-xylylethane and 1-phenyl-l-ethylphenylethane) , Cactus Solvent HP-MN (commercial name of Japan EnergyCorporation, containing 80% of methylnaphthalene) , Cactus Solvent HP-DMN (commercial name of Japan Energy Corporation, containing 80% of dimethylnaphthalene) , Cactus Solvent P-100 (commercial name of Japan Energy Corporation, alkylbenzene having 9 to 10 carbon atoms) , Cactus Solvent P-150 (commercial name of Japan Energy Corporation, alkylbenzene) , Cactus Solvent P-180 (commercial name of Japan Energy Corporation, a mixture of methylnaphthalene and dimethylnaphthalene) , Cactus Solvent P-200 (commercial name of
  • the emulsifiable concentrate of the present invention contains the other hydrophobic organic solvents in a range from 0 to 35% by weight in total based on the total amount of the pesticide emulsifiable concentrate of the present invention.
  • the pesticide emulsifiable concentrate of the present invention contains a hydrophilic organic solvent.
  • the hydrophilic organic solvent in the present invention include aliphatic acid amides such as N, N-dimethylacetamide, N,N-dimethyl propionamide and N,N-dimethylformamide; N-alkyl pyrrolidone such as N-methyl pyrrolidone and N-ethyl pyrrolidone; 1, 3-dimethyl-2-imidazolidinone; dimethyl sulfoxide; andmixture thereof, among whichN-methyl pyrrolidone and/or 1, 3-dimethyl-2-imidazolidinone are preferable.
  • the hydrophilic organic solvent is contained in the pesticide emulsifiable concentrate of the present invention in an amount required to dissolve the present acetonitrile compound contained (for example, the weight ratio of the present acetonitrile compound to the hydrophilic organic solvent is in a range from 1:1 to 1:20) , and is generally in a range from 10 to 55% by weight, preferably from 10 to 45% by weight, and more preferably from 15 to 45% by weight based on the total amount of the pesticide emulsifiable concentrate of the present invention.
  • the surfactant contained in the pesticide emulsifiable concentrate of the present invention is preferably a combination of an anionic surfactant and a nonionic surfactant.
  • anionic surfactant examples include alkyl aryl sulfonic acid salt such as dodecyl benzene sulfonic acid salt and the like, polyoxyethylene (poly) arylaryl ether sulfates such as polyoxyethylene distyryl phenyl ether sulfate and the like, polyoxyethylene (poly) arylaryl ether phosphate such as polyoxyethylene tristyryl phenyl ether phosphate and the like, polyoxyethylene alkylaryl phosphate ester, and polyoxyethylene alkyl phosphate ester.
  • alkyl aryl sulfonic acid salt such as alkyl benzene sulfonic acid salt, especially dodecyl benzene sulfonic acid salt such as sodium salt and calcium salt is used.
  • sodium salt, calcium salt and ammonium salt are exemplified as sulfonic acid salt, sulfate salt or phosphate salt .
  • surfactant such as Rhodacal 70, Rhodacal70/B, Rhodacal ⁇ O/BE (each produced by Rhodia), Witconate P-1220EH (produced by Akzo Nobel) and NANSA EVM62/H (produced by Huntsman) can be used as dodecyl benzene sulfonic acid salt.
  • Commercially available surfactant such as Soprophor DSS/11 (produced by Rhodia) can be used as polyoxyethylene distyryl phenyl ether sulfate.
  • Commercially available surfactant such as Soprophor FLK (produced by Rhodia) can be used as polyoxyethylene tristiryl phenyl ether phosphoric acid.
  • Rhodafac PS/17 can be used as polyoxyethylenealkylaryl phosphate ester.
  • Commercially available surfactant such as Rhodafac MB can be used as polyoxyethylenealkyl phosphate ester.
  • nonionic surfactant examples include sorbitan fatty acid ester such as sorbitanmono laurate, sorbitan mono palmitate, sorbitan mono stearate and sorbitan mono oleate; polyoxyethylene-polyoxypropylene block polymer; fatty acid ester of polyoxyethylene-polyoxypropylene block polymer; polyoxyethylene-polyoxypropylene alkyl ether; polyoxyethylene-polyoxypropylene polyaryl ether such as polyoxyethylene-polyoxypropylene tristyryl phenyl ether, polyoxyethylene-polyoxypropylene distyryl phenyl ether and the like; polyoxyethylene-polyoxypropylene alkyl aryl ether; polyoxyethylene alkyl aryl ether; polyoxyethylene polyaryl ether such as polyoxyethylene tristyryl phenyl ether, polyoxyethylene distyryl phenyl ether and the like; polyoxyethylene vegetable oil such as polyoxyethylene cast
  • Preferable examples are the nonionic surfactant which has polyalkylene oxide structure in the molecule such as polyoxyethylene-polyoxypropylene block polymer, polyoxyethylene-polyoxypropylene tristyryl phenyl ether, polyoxyethylene tristyryl phenyl ether, polyoxyethylene castor oil, polyoxyethylene hardened castor oil, polyoxyethylene alkyl aryl ether, polyoxyethylene tristyryl phenyl phosphate diester and polyoxyethylene-polyoxypropylene tristyryl phenyl phosphate diester.
  • polyoxyethylene-polyoxypropylene block polymer polyoxyethylene-polyoxypropylene tristyryl phenyl ether, polyoxyethylene tristyryl phenyl ether, polyoxyethylene castor oil, polyoxyethylene hardened castor oil, polyoxyethylene alkyl aryl ether, polyoxyethylene tristyryl phenyl phosphate diester and polyoxyethylene-polyoxyprop
  • More preferable examples include polyoxyethylene-polyoxypropylene block , polymer, polyoxyethylene-polyoxypropylene tristyryl phenyl ether, polyoxypropylene tristyryl phenyl ether, and polyoxyethylene caster oil .
  • surfactant such as Alkamuls S20 (sorbitan mono laurate, HLB 8.6, produced by Rhodia Nicca) , Alkamuls S80 (sorbitan mono oleate, HLB 4.3, produced by Rhodia Nicca) , Glycomul S (sorbitan mono stearate, HLB 5, produced by Lonza Japan) , Glycomul TS (sorbitan tri stearate, HLB 2, produced by Lonza Japan), NIKKOL SL-IO (sorbitan mono laurate, HLB 8.6, produced by Nikko Chemicals), NIKKOL SP-IOV (sorbitan mono palmitate, HLB 6.7, produced by Nikko Chemicals), NIKKOL SS-IOV (sorbitan mono stearate, HLB 4.7, produced by Nikko Chemicals), NIKKOL SS-30V (sorbitan tri stearate, HLB 2.1, produced by Nikko Chemicals), NIKKOL SI-IORV (sorbitan mono is
  • Teric PE 64 produced by Huntsman
  • Teric PE 64 Commercially available surfactant such as Teric PE 64 (produced by Huntsman) can be used as polyoxyethylene-polyoxypropylene block polymer.
  • surfactant such as Antarox BO/327 , 340 Antarox BO series (each produced by Rhodia) can be used as polyoxyethylene-polyoxypropylene alkyl ether.
  • Commercially available surfactant such as Solpol T26 (produced by Toho Chemical Industry) can be used as polyoxyethylene alkyl aryl ether.
  • surfactant such as Soprophor 796/P(HLB 13.7, produced by Rhodia) can be used as polyoxyethylene-polyoxypropylene tristyryl phenyl ether.
  • surfactant such as Soprophor BSU (HLB 12.6, . produced by Rhodia) can be used as polyoxyethylene tristyryl phenyl ether.
  • surfactant such as Alkamuls OR40, Alkamuls BR (each produced by Rhodia) can be used as polyoxyethylene castor oil.
  • surfactant such as HCO-20 (produced by Nikko Chemicals) can be used as polyoxyethylene hardened castor oil.
  • surfactant such as CR series such as Antarox CR/255, CR/405 and the like (each produced by Rhodia) can be used as polyoxyethylene-polyoxypropylene castor oil.
  • Commercially available surfactant such as Newcol 150 (produced by Nippon Nyukazai) can be used as polyoxyethylene fatty acid ester.
  • surfactant such as Newcol 1100, Newcol 1105 (each produced by Nippon Nyukazai) can be used as polyoxyethylene alkyl aryl ester.
  • surfactant such as PIONIN D-900 series (produced by TAKEMOTO Oil &Fat) can be used as fatty acid ester of glycerin.
  • the amount of a surfactant contained in the pesticide emulsifiable concentrate of the present invention is generally in a range from 4 to 25% by weight, and preferably from 5 to 20% by weight, based on the total amount of the pesticide emulsifiable concentrate of the present invention.
  • the surfactant is a combination of an anionic surfactant and a nonionic surfactant
  • the weight ratio of the anionic surfactant and the nonionic surfactant is generally in a range from 1:0.1 to 1:10, and preferably from 1:0.4 to 1:2.5.
  • anionic surfactants and/or nonionic surfactants can be used in combination.
  • the pesticide emulsifiable concentrate of the present invention may contain adjuvants for formulation, such as antioxidants, colorants, perfumes, potency enhancers and safeners .
  • antioxidant examples include 3-/2-t-butyl-4-hydroxyanisol andbutylatedhydroxytoluene
  • examples of the colorant examples include Rhodamine B, Yellow No. 4, Blue No. 1 and Red No. 2.
  • the amount of the adjuvants for formulation contained in the emulsifiable concentrate of the present invention is generally in a range from 0 to 5% by weight in total based on the total amount of the pesticide emulsifiable concentrate of the present invention.
  • a pesticide emulsifiable concentrate which comprises 1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight of the present hydrophobic organic solvent;
  • a pesticide emulsifiable concentrate which comprises 1 to 10 parts by weight of the present acetonitrile compound; 20 to 80 parts by weight of the present hydrophobic organic solvent;
  • a pesticide emulsifiable concentrate which comprises
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which essentially consists of: 1 to 10 parts by weight of the present acetonitrile compound;
  • a pesticide emulsifiable concentrate which essentially consists of: 3 to 7 parts by weight of the present acetonitrile compound;
  • a pesticide emulsifiable concentrate which comprises 1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight of the present hydrophobic organic solvent;
  • a pesticide emulsifiable concentrate which comprises
  • a pesticide emulsifiable concentrate which comprises
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which essentially consists of: 1 to 10 parts by weight of the present acetonitrile compound;
  • a pesticide emulsifiable concentrate which essentially consists of: 3 to 7 parts by weight of the present acetonitrile compound;
  • a pesticide emulsifiable concentrate which comprises 1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight of diethyl oxalate;
  • a pesticide emulsifiable concentrate which comprises 3 to 7 parts by weight of the present acetonitrile compound; 20 to 75 parts by weight of diethyl oxalate; 15 to 40 parts by weight of a hydrophilic organic solvent; and
  • a pesticide emulsifiable concentrate which essentially consists of: 1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight of diethyl oxalate; 10 to 55 parts by weight of a hydrophilic organic solvent; and
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which comprises
  • a pesticide emulsifiable concentrate which comprises
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which comprises
  • a hydrophilic organic solvent selected from the group consisting of N-methyl pyrrolidone and 1, 3-dimethyl-2-imidazolidinone;
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which comprises
  • aromatic hydrocarbon 0 to 20 parts by weight of aromatic hydrocarbon; 15 to 40 parts by weight of a hydrophilic organic solvent selected from the group consisting of N-methyl pyrrolidone and
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which comprises 1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight of diethyl oxalate; 10 to 55 parts by weight of 1, 3-dimethyl-2-imidazolidinone;
  • a pesticide emulsifiable concentrate which comprises
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which comprises 1 to 10 parts by weight of the present acetonitrile compound; 20 to 80 parts by weight of diethyl oxalate; 10 to 45 parts by weight of 1, 3-dimethyl-2-imidazolidinone;
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which comprises 1 to 10 parts by weight of the present acetonitrile compound; 5 to 80 parts by weight of diethyl oxalate;
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which comprises
  • a pesticide emulsifiable concentrate which essentially consists of: 3 to 7 parts by weight of the present acetonitrile compound; 20 to 80 parts by weight of diethyl oxalate; 0 to 35 parts by weight of aromatic hydrocarbon; 10 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and 5 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to 1, 3-dimethyl-2-imidazolidinone is from 4:6 to 8:2.
  • a pesticide emulsifiable concentrate which comprises 1 to 10 parts by weight of the present acetonitrile compound
  • a pesticide emulsifiable concentrate which comprises
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which essentially consists of: 3 to 7 parts by weight of the present acetonitrile compound;
  • a pesticide emulsifiable concentrate which comprises 1 to 10 parts by weight of the present acetonitrile compound
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which comprises
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which comprises 1 to 10 parts by weight of the present acetonitrile compound
  • a pesticide emulsifiable concentrate which comprises
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which comprises
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which comprises
  • aromatic hydrocarbon 10 to 55 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and 4 to 25 parts by weight of a surfactant.
  • a pesticide emulsifiable concentrate which essentially consists of:
  • a pesticide emulsifiable concentrate which comprises 3 to 7 parts by weight of the present acetonitrile compound; 20 to 80 parts by weight of diethyl oxalate; 0 to 35 parts by weight of aromatic hydrocarbon; 10 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and
  • a pesticide emulsifiable concentrate which essentially consists of:
  • the pesticide emulsifiable concentrate of the present invention can be prepared, for example, by adding the present acetonitrile compound to a mixture of the present hydrophobic organic solvent and a hydrophilic organic solvent under optionally heating condition (80 0 C or lower), and adding a surfactant (and adjuvants for formulation, if necessary) , followed by uniformly stirring and optionally filtering.
  • the pesticide emulsifiable concentrate of the present invention is filled in a vessel such as a bottle made of polyethylene or polyethylene terephthalate, .or a metal can. Since the pesticide emulsifiable concentrate of the present invention is not separated into two layers even when it absorbs a small amount of moisture during storage, a uniform pesticide emulsifiable concentrate can be taken out of a vessel when used.
  • the pesticide emulsifiable concentrate of the present invention is generally diluted with water, and used by spraying the aqueous dilute solution over crops .
  • an aqueous dilute solution which is obtained by dilution of the pesticide emulsifiable concentrate of the present invention with water, is prepared by diluting the pesticide emulsifiable concentrate of the present invention with water generally from 10 to 10, 000 times so as for the concentration of the present acetonitrile compound to be approximately fromO .1 to 1, 000 ppm, andpreferably approximately from 1 to 500 ppm.
  • Water used for the preparation may generally be either soft water or hard water, and an adjuvant such as a spreader can be added thereto if necessary.
  • the pesticide emulsifiable concentrate of the present invention has good emulsion stability when it is diluted with water.
  • the application amount of the aqueous dilute solution, which is obtained by dilution of the pesticide emulsifiable concentrate of the present invention, is generally from 0.1 to 10,000 g, preferably from 1 to 250 g, per hectare as an amount of the present acetonitrile compound.
  • the present acetonitrile compound (2.0 g in terms of pure component), calcium dodecylbenzene sulfonate (Rhodacal 70, manufactured by RHODIA; 4.00 g) , polyoxyethylene polyoxypropylene tristyrylphenyl ether (Soprophor 796/P, manufactured by RHODIA; 3.00 g) and 1, 3-dimethyl-2-imidazolidinone (45.0Og) were weighed in a 100 ml volumetric flask at 20 0 C, and diethyl oxalate (an amount equivalent to 53 g) was added thereto to make 100 ml in total. The mixture was stirred until the solution became uniform under heating to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 1 of the present invention) .
  • Preparation Example 2 Preparation Example 2
  • the present acetonitrile compound (2.0 g in terms of pure component) , calcium dodecylbenzene sulfonate (Rhodacal 70, manufactured by RHODIA; 5.60 g) , polyoxyethylene polyoxypropylene tristyrylphenyl ether (Soprophor 796/P, manufactured by RHODIA; 1.4 g) and 1, 3-dimethyl-2-imidazolidinone (45.00 g) were weighed in a 100 ml volumetric flask at 2O 0 C, and diethyl oxalate (an amount equivalent to 53 g) was added thereto to make 100 ml in total. The mixture was stirred until the solution became uniform under heating to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 2 of the present invention) .
  • a pesticide emulsifiable concentrate of the present invention hereafter referred to as the emulsif
  • the present acetonitrile compound ( 5.0 g in terms of pure component) , calcium dodecylbenzene sulfonate (NANSA EVM 62/H, manufactured by HUNTSMAN; 5.60 g) , polyoxyethylene polyoxypropylene block polymer (TOXIMUL 8320, manufactured by STEPAN; 6.4O g), 1, 3-dimethyl-2-imidazolidinone (30.0O g) and aromatic 'hydrocarbon (mainly CIl to C14 alkylnaphthalene, Solvesso 200 ND, manufactured by EXXON MOBIL CHEMICAL COMPANY; 10.00 g) were weighed in a 100 ml volumetric flask at 20 0 C, and diethyl oxalate (an amount equivalent to 51 g) was added thereto to make 100 ml in total. The mixture was stirred until the solution became uniform under heating to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred
  • the present acetonitrile compound (5.0 g in terms of pure component) , calcium dodecylbenzene sulfonate (NANSA EVM 62/H, manufactured by HUNTSMAN; 5.80 g) , polyoxyethylene polyoxypropylene block polymer (TOXIMUL 8320, manufactured by STEPAN; 6.20 g) , 1, 3-dimethyl-2-imidazolidinone (30.00 g) and aromatic hydrocarbon (mainly ClI to C14 alkylnaphthalene, Solvesso 200 ND, manufactured by EXXON MOBIL CHEMICAL COMPANY; 15.00 g) were weighed in a 100 ml volumetric flask at 20 0 C, and diethyl oxalate (an amount equivalent to 45 g) was added thereto to make 100 ml in total. The mixture was stirred until the solution became uniform under heating to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the e
  • the present acetonitrile compound (10.00 g in terms of pure component) was added to a mixture of diethyl oxalate (45 g) and N-methyl pyrrolidone (35 g) and dissolved therein at 20 0 C. Then Solpol 3005X (manufactured by TOHO KAGAKU; 10 g) was added thereto and stirred to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 5 of the present invention) .
  • the present acetonitrile compound (5.0 g in terms of pure component) , calcium dodecylbenzene sulfonate (NANSA EVM 62/H, manufactured by HUNTSMAN; 10.0 g) , polyoxyethylene alkyl ether
  • a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 6 of the present invention) .
  • the present acetonitrile compound (3.0 g in terms of pure component) , calcium dodecylbenzene sulfonate (NANSA EVM 62/H, manufactured by HUNTSMAN; 5.0 g) , sorbitan fatty acid ester
  • emulsifiable concentrate 7 of the present invention 1, 3-dimethyl-2-imidazolidinone (15.00 g) and xylene (15.00 g) were weighed in a 100 ml volumetric flask at 20 0 C, and diethyl oxalate (an amount equivalent to 62 g) was added thereto to make 100 ml in total. The mixture was stirred until the solution became uniform under heating to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 7 of the present invention) .
  • the present acetonitrile compound (5.0 g in terms of pure component) , calcium dodecylbenzene sulfonate (NANSA EVM 62/H, manufactured by HUNTSMAN; 5.00 g) , polyoxyethylene polyoxypropylene block polymer (TOXIMUL 8320, manufactured by STEPAN; 7.00 g) , 1, 3-dimethyl-2-imidazolidinone (30.00 g) and aromatic hydrocarbon (mainly CIl to C14 alkylnaphthalene, Solvesso 200 ND, manufactured by EXXON MOBIL CHEMICAL COMPANY; 30.00 g) were weighed in a 100 ml volumetric flask at 20 0 C, and diethyl oxalate (an amount equivalent to 28 g) was added thereto to make 100 ml in total. The mixture was stirred until the solution became uniform under heating to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the
  • the present acetonitrile compound (5.0 g in terms of pure component) , calcium dodecylbenzene sulfonate (NANSA EVM 62/H, manufactured by HUNTSMAN; 7.00 g) , polyoxyethylene castor oil
  • a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 9 of the present invention) .
  • the present acetonitrile compound (10.00 g in terms of pure component) was added to a mixture of aromatic hydrocarbon (mainly ClO to ClI alkylbenzene, Solvesso 150, manufactured by
  • Test Example 1 10 g of a pesticide emulsifiable concentrate and 1 g of pure water were placed in a 20 ml ampoule tube (manufactured by MARUEMU, screw tube No. 5) and intensively stirred. After stirring, the tube was allowed to stand for one hour, and visual observation of the mixture was conducted to confirm the presence or absence of separation in the liquid phase. The results are shown in Table 1.
  • the pesticide emulsifiable concentrate of the present invention has good storage stability so as not to separate into two layers even when it absorbs a small amount of moisture, and is also excellent in emulsion stability when diluted with water .

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A pesticide emulsifiable concentrate containing 2-[(2-fluoro-5-trifluoromethyl)phenylthio]-2-[3-(2-methoxyphenyl)-2-thiazolydinyliden]acetonitrile, a hydrophobic organic solvent containing diethyl oxalate, a hydrophilic organic solvent and a surfactant, wherein the weight ratio of diethyl oxalate to the hydrophilic organic solvent is in a range from 3:7 to 9:1 has an excellent in storage stability and has also an excellent in emulsion stability when diluted with water.

Description

DESCRIPTION
PESTICIDE EMULSIFIABLE CONCENTRATE
TECHNICAL FIELD
The present invention relates to a pesticide emulsifiable concentrate which contains
2- [ (2-fluoro-5-trifluoromethyl) phenylthio] -2- [3- (2-methoxyp henyl) -2-thiazolydinyliden] acetonitrile as apesticidal active ingredient.
BACKGROUND ART
It is known that
2- [ (2-fluoro-5-trifluoromethyl) phenylthio] -2- [3- (2-methoxyp henyl) -2-thiazolydinyliden] acetonitrile (hereafter referred to as the present acetonitrile compound) is an active ingredient of an agricultural or horticultural fungicide in US 6,710,062 Bl. Also, a pesticide emulsifiable concentrate containing the present acetonitrile compound as a pesticidal active ingredient is described in US 6,710,062 Bl.
DISCLOSURE OF THE INVENTION
However, the pesticide • emulsifiable concentrate containing the present acetonitrile compound as a pesticidal active ingredient described inUS6,710,062Blislikelytoabsorb water during preparation and/or storage and is inferior in storage stability of a formulation, namely, the pesticide emulsifiable concentrate is separated into two layers when it absorbs water. The object of the present invention is to provide a pesticide emulsifiable concentrate containing the present acetonitrile compound as a pesticidal active ingredient, which is excellent in storage stability and is also excellent in emulsion stability when diluted with water.
The present inventors have intensively studied so as to achieve the above object and found that a pesticide emulsifiable concentrate, which contains the present acetonitrile compound, a hydrophobic organic solvent containing diethyl oxalate, a hydrophilic organic solvent and a surfactant, wherein the weight ratio of diethyl oxalate to the hydrophilic organic solvent falls within a range from 3:7 to 9:1, is less likely to be separated into two layers when it absorbs moisture and is also excellent in emulsion stability when diluted with water, and thus the present invention has been made.
That is, the present invention is as follows. [1] A pesticide emulsifiable concentrate comprising 2- [ (2-fluoro-5-trifluoromethyl)phenylthio]-2-[3- (2-methoxyp henyl) -2-thiazolydinyliden] acetonitrile, a hydrophobic organic solvent containing diethyl oxalate, a hydrophilic organic solvent and a surfactant, wherein the weight ratio of diethyl oxalate to the hydrophilic organic solvent is in a range from 3:7 to 9:1.
[2] The pesticide emulsifiable concentrate according to [1] , wherein the weight ratio of diethyl oxalate to the hydrophilic organic solvent is in a range from 4:6 to 8:2. [3] The pesticide emulsifiable concentrate according to [1] or [2] , wherein other hydrophobic organic solvents other than diethyl oxalate are aromatic hydrocarbons.
[4] The pesticide emulsifiable concentrate according to any one of [1] to [3] , wherein the hydrophilic organic solvent is at least one kind of an organic solvent selected from the group consisting of N, N-dimethyl acetamide, N,N-dimethyl propionamide, N,N-dimethyl formamide, N-methyl pyrrolidone,
N-ethyl pyrrolidone, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide.
[5] The pesticide emulsifiable concentrate according to any one of [1] to [4], wherein the surfactant is an anionic surfactant and a nonionic surfactant, and the weight ratio of the anionic surfactant to the nonionic surfactant is from 1:0.1 to 1:10.
[6] The pesticide emulsifiable concentrate according to any one of [1] to [5], which essentially consists of: 1 to 10 parts by weight of 2- [ (2-fluoro-5-trifluoromethyl) phenylthio] -2- [3- (2-methoxyp henyl) -2-thiazolydinyliden] acetonitrile;
10 to 80 parts by weight of a hydrophobic organic solvent containing diethyl oxalate;
10 to 55 parts by weight of a hydrophilic organic solvent; 4 to 25 parts by weight of a surfactant; and 0 to 5 parts by weight of adjuvants for formulation.
[7] The pesticide emulsifiable concentrate according to any one of [1] to [5], which essentially consists of: 3 to 7 parts by weight of 2- [ (2-fluoro-5-trifluoromethyl) phenylthio] -2- [3- (2-methoxyp henyl) -2-thiazolydinyliden] acetonitrile;
20 to 80 parts by weight of a hydrophobic organic solvent containing diethyl oxalate;
15 to 45 parts by weight of a hydrophilic organic solvent; 5 to 20 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation.
[8] The pesticide emulsifiable concentrate according to any one of [1] to [5], which essentially consists of:
1 to 10 parts by weight of 2- [ (2-fluoro-5-trifluoromethyl) phenylthio] -2- [3- (2-methoxyp henyl) -2-thiazolydinyliden] acetonitrile;
5 to 80 parts by weight of diethyl oxalate;
0 to 35 parts by weight of other hydrophobic organic solvents other than diethyl oxalate; 10 to 55 parts by weight of a hydrophilic organic solvent;
4 to 25 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation.
[9] The pesticide emulsifiable concentrate according to any one of [1] to [5] , which essentially consists of: 1 to 10 parts by weight of
2- [ (2-fluoro-5-trifluoromethyl) phenylthio] -2- [3- (2-methoxyp henyl) -2-thiazolydinyliden] acetonitrile;
20 to 80 parts by weight of diethyl oxalate;
0 to 35 parts by weight of other hydrophobic organic solvents other than diethyl oxalate;
10 to 55 parts by weight of a hydrophilic organic solvent;
4 to 25 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation.
[10] An aqueous dilute solution prepared by diluting the pesticide emulsifiable concentrate according to any one of [1] to [9] with water by 10 to 10,000 times.
The present acetonitrile compound contained in the pesticide emulsifiable concentrate of the present invention is a compound represented by the following formula (1) :
Figure imgf000006_0001
The present acetonitrile compound can be produced by a method described in US 6,710,062 Bl.
The amount of the present acetonitrile compound contained in the pesticide emulsifiable concentrate of the present invention is generally in a range from 1 to 10% by weight based on the total amount of the pesticide emulsifiable concentrate of the present invention.
The hydrophobic organic solvent containing diethyl oxalate (hereafter referredto as the present hydrophobic organic solvent) inthepesticide emulsifiable concentrate ofthepresent inventionmeans a hydrophobic organic solvent containing diethyl oxalate in an amount of 35 to 100% by weight . That is, the present hydrophobic organic solvent may be diethyl oxalate itself, or a mixture of diethyl oxalate and one or more other hydrophobic organic solvents other than diethyl oxalate, and also the content of diethyl oxalate is 35% by weight or more based on the total amount of the present hydrophobic organic solvent.
It is preferable that the content of diethyl oxalate of the present hydrophobic organic solvent is from 40 to 100% by weight .
In the present invention, commercially available diethyl oxalate can be used.
The amount of the present hydrophobic organic solvent is generally in a range from 10 to 80% by weight, and preferably from 20 to 80% by weight, based on the total amount of the pesticide emulsifiable concentrate of the present invention. The amount of diethyl oxalate is generally in a range from 5 to 80% by weight, preferably from 10 to 80% by weight, and more preferably from 20 to 80% by weight, based on the total amount of the pesticide emulsifiable concentrate of the present invention. The weight ratio of diethyl oxalate to the hydrophilic organic solvent contained in the pesticide emulsifiable concentrate of the present invention is in a range from 3:7 to 9:1, and preferably from 4:6 to 8:2.
In the present invention, the present hydrophobic organic solvent can contain other hydrophobic organic solvents other than diethyl oxalate (hereafter referred to as the other hydrophobic organic solvent) .
Examples of another hydrophobic organic solvent includes aromatic hydrocarbons such as alkylbenzene (for example, xylene, tetramethylbenzene and the like) , alkylnaphthalene (for example, methylnaphthalene) , diphenylethane, dixylylethane, phenylxylylethane and the like; fatty acid monoesters such as methyl laurate, isopropyl myristate, isopropyl palmitate, methyl caprate, methyl oleate, isobutyl oleate, butyl propionate, isoamyl propionate, ethyl butyrate, butyl butyrate, isoamyl butyrate, isoamyl valerate, amyl lactate, methyl linoleate, methyl linolenate, palm fatty acidmethyl and the like; aliphatic hydrocarbons such as cyclohexane. Preferable examples of another hydrophobic organic solvent includes aromatic hydrocarbons . Commercially available products such as Hisol SAS-296 (commercial name of Nippon Oil Corp., a mixture of 1-phenyl-l-xylylethane and 1-phenyl-l-ethylphenylethane) , Cactus Solvent HP-MN (commercial name of Japan EnergyCorporation, containing 80% of methylnaphthalene) , Cactus Solvent HP-DMN (commercial name of Japan Energy Corporation, containing 80% of dimethylnaphthalene) , Cactus Solvent P-100 (commercial name of Japan Energy Corporation, alkylbenzene having 9 to 10 carbon atoms) , Cactus Solvent P-150 (commercial name of Japan Energy Corporation, alkylbenzene) , Cactus Solvent P-180 (commercial name of Japan Energy Corporation, a mixture of methylnaphthalene and dimethylnaphthalene) , Cactus Solvent P-200 (commercial name of Japan Energy Corporation, a mixture of methylnaphthalene and dimethylnaphthalene) , Cactus Solvent P-220 (commercial name of Japan Energy Corporation, a mixture of methylnaphthalene and dimethylnaphthalene) , Cactus Solvent PAD-I (commercial name of Japan Energy Corporation, dimethylmonoisopropylnaphthalene) , Solvesso 100 (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly C9 to ClO dialkyl and trialkyl benzene) , Solvesso 150 (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly ClO to CIl alkylbenzene) , Solvesso 150ND (commercial name of ExxonMobil Chemical Company, aromatic hydrocarbon, mainly ClO to CIl alkylbenzene) , Solvesso 200 (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly ClO to C14 alkylnaphthalene) , ULTRA LOW NAPHTHALENEAROMATIC 150 (commercial name of ExxonMobil Chemical Company, aromatic hydrocarbon, mainly ClO to CIl alkylbenzene) , ULTRA LOW NAPHTHALENE AROMATIC 200 (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly CIl to C14 alkylnaphthalene) , Solvesso 200 ND (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly CIl to C14 alkylnaphthalene) , Suwasol 100 (commercial name of Maruzen Petrochemical Company, toluene) and Suwasol 200 (commercial name of Maruzen Petrochemical Company, xylene) can be used as the aromatic hydrocarbons.
The emulsifiable concentrate of the present invention contains the other hydrophobic organic solvents in a range from 0 to 35% by weight in total based on the total amount of the pesticide emulsifiable concentrate of the present invention.
The pesticide emulsifiable concentrate of the present invention contains a hydrophilic organic solvent. Examples of the hydrophilic organic solvent in the present invention include aliphatic acid amides such as N, N-dimethylacetamide, N,N-dimethyl propionamide and N,N-dimethylformamide; N-alkyl pyrrolidone such as N-methyl pyrrolidone and N-ethyl pyrrolidone; 1, 3-dimethyl-2-imidazolidinone; dimethyl sulfoxide; andmixture thereof, among whichN-methyl pyrrolidone and/or 1, 3-dimethyl-2-imidazolidinone are preferable. The hydrophilic organic solvent is contained in the pesticide emulsifiable concentrate of the present invention in an amount required to dissolve the present acetonitrile compound contained (for example, the weight ratio of the present acetonitrile compound to the hydrophilic organic solvent is in a range from 1:1 to 1:20) , and is generally in a range from 10 to 55% by weight, preferably from 10 to 45% by weight, and more preferably from 15 to 45% by weight based on the total amount of the pesticide emulsifiable concentrate of the present invention.
The surfactant contained in the pesticide emulsifiable concentrate of the present invention is preferably a combination of an anionic surfactant and a nonionic surfactant.
Examples of anionic surfactant include alkyl aryl sulfonic acid salt such as dodecyl benzene sulfonic acid salt and the like, polyoxyethylene (poly) arylaryl ether sulfates such as polyoxyethylene distyryl phenyl ether sulfate and the like, polyoxyethylene (poly) arylaryl ether phosphate such as polyoxyethylene tristyryl phenyl ether phosphate and the like, polyoxyethylene alkylaryl phosphate ester, and polyoxyethylene alkyl phosphate ester. Preferably alkyl aryl sulfonic acid salt such as alkyl benzene sulfonic acid salt, especially dodecyl benzene sulfonic acid salt such as sodium salt and calcium salt is used.
Generally, sodium salt, calcium salt and ammonium salt are exemplified as sulfonic acid salt, sulfate salt or phosphate salt .
Commercially available surfactant such as Rhodacal 70, Rhodacal70/B, RhodacalβO/BE (each produced by Rhodia), Witconate P-1220EH (produced by Akzo Nobel) and NANSA EVM62/H (produced by Huntsman) can be used as dodecyl benzene sulfonic acid salt. Commercially available surfactant such as Soprophor DSS/11 (produced by Rhodia) can be used as polyoxyethylene distyryl phenyl ether sulfate. Commercially available surfactant such as Soprophor FLK (produced by Rhodia) can be used as polyoxyethylene tristiryl phenyl ether phosphoric acid. Commercially available surfactant such as Rhodafac PS/17 (produced by Rhodia) can be used as polyoxyethylenealkylaryl phosphate ester. Commercially available surfactant such as Rhodafac MB (produced by Rhodia) can be used as polyoxyethylenealkyl phosphate ester.
Examples of nonionic surfactant include sorbitan fatty acid ester such as sorbitanmono laurate, sorbitan mono palmitate, sorbitan mono stearate and sorbitan mono oleate; polyoxyethylene-polyoxypropylene block polymer; fatty acid ester of polyoxyethylene-polyoxypropylene block polymer; polyoxyethylene-polyoxypropylene alkyl ether; polyoxyethylene-polyoxypropylene polyaryl ether such as polyoxyethylene-polyoxypropylene tristyryl phenyl ether, polyoxyethylene-polyoxypropylene distyryl phenyl ether and the like; polyoxyethylene-polyoxypropylene alkyl aryl ether; polyoxyethylene alkyl aryl ether; polyoxyethylene polyaryl ether such as polyoxyethylene tristyryl phenyl ether, polyoxyethylene distyryl phenyl ether and the like; polyoxyethylene vegetable oil such as polyoxyethylene castor oil and the like; polyoxyethylene hardened vegetable oil such as polyoxyethylene hardened castor oil and the like; polyoxyethylene-polyoxypropylene vegetable oil such as polyoxyethylene-polyoxypropylene castor oil and the like; polyoxyethylene fatty acid esters; polyoxyethylene alkyl ether; polyoxyethylene tristyryl phenyl phosphate diester; polyoxyethylene-polyoxypropylene tristyryl phenyl phosphate diester; fatty acid alcohol polyglycol ether; and fatty acid ester of glycerin.
Preferable examples are the nonionic surfactant which has polyalkylene oxide structure in the molecule such as polyoxyethylene-polyoxypropylene block polymer, polyoxyethylene-polyoxypropylene tristyryl phenyl ether, polyoxyethylene tristyryl phenyl ether, polyoxyethylene castor oil, polyoxyethylene hardened castor oil, polyoxyethylene alkyl aryl ether, polyoxyethylene tristyryl phenyl phosphate diester and polyoxyethylene-polyoxypropylene tristyryl phenyl phosphate diester.
More preferable examples include polyoxyethylene-polyoxypropylene block , polymer, polyoxyethylene-polyoxypropylene tristyryl phenyl ether, polyoxypropylene tristyryl phenyl ether, and polyoxyethylene caster oil .
Commercially available surfactant such as Alkamuls S20 (sorbitan mono laurate, HLB 8.6, produced by Rhodia Nicca) , Alkamuls S80 (sorbitan mono oleate, HLB 4.3, produced by Rhodia Nicca) , Glycomul S (sorbitan mono stearate, HLB 5, produced by Lonza Japan) , Glycomul TS (sorbitan tri stearate, HLB 2, produced by Lonza Japan), NIKKOL SL-IO (sorbitan mono laurate, HLB 8.6, produced by Nikko Chemicals), NIKKOL SP-IOV (sorbitan mono palmitate, HLB 6.7, produced by Nikko Chemicals), NIKKOL SS-IOV (sorbitan mono stearate, HLB 4.7, produced by Nikko Chemicals), NIKKOL SS-30V (sorbitan tri stearate, HLB 2.1, produced by Nikko Chemicals), NIKKOL SI-IORV (sorbitan mono isostearate, HLB 5.0, produced by Nikko Chemicals), NIKKOL S0-15R (sorbitan sesquioleate and HLB 4.5, produced by Nikko Chemicals) can be used as sorbitan fatty acid ester.
Commercially available surfactant such as Teric PE 64 (produced by Huntsman) can be used as polyoxyethylene-polyoxypropylene block polymer.
Commercially available surfactant such as Antarox BO/327 , 340 Antarox BO series (each produced by Rhodia) can be used as polyoxyethylene-polyoxypropylene alkyl ether. ■ Commercially available surfactant such as Solpol T26 (produced by Toho Chemical Industry) can be used as polyoxyethylene alkyl aryl ether.
Commercially available surfactant such as Soprophor 796/P(HLB 13.7, produced by Rhodia) can be used as polyoxyethylene-polyoxypropylene tristyryl phenyl ether.
Commercially available surfactant such as Soprophor BSU (HLB 12.6,. produced by Rhodia) can be used as polyoxyethylene tristyryl phenyl ether. Commercially available surfactant such as Alkamuls OR40, Alkamuls BR (each produced by Rhodia) can be used as polyoxyethylene castor oil.
Commercially available surfactant such as HCO-20 (produced by Nikko Chemicals) can be used as polyoxyethylene hardened castor oil.
Commercially available surfactant such as CR series such as Antarox CR/255, CR/405 and the like (each produced by Rhodia) can be used as polyoxyethylene-polyoxypropylene castor oil. Commercially available surfactant such as Newcol 150 (produced by Nippon Nyukazai) can be used as polyoxyethylene fatty acid ester.
Commercially available surfactant such as Newcol 1100, Newcol 1105 (each produced by Nippon Nyukazai) can be used as polyoxyethylene alkyl aryl ester. Commercially available surfactant such as PIONIN D-900 series (produced by TAKEMOTO Oil &Fat) can be used as fatty acid ester of glycerin.
The amount of a surfactant contained in the pesticide emulsifiable concentrate of the present invention is generally in a range from 4 to 25% by weight, and preferably from 5 to 20% by weight, based on the total amount of the pesticide emulsifiable concentrate of the present invention. When the surfactant is a combination of an anionic surfactant and a nonionic surfactant, the weight ratio of the anionic surfactant and the nonionic surfactant is generally in a range from 1:0.1 to 1:10, and preferably from 1:0.4 to 1:2.5.
Also, in the present invention, two or more kinds of anionic surfactants and/or nonionic surfactants can be used in combination.
The pesticide emulsifiable concentrate of the present invention may contain adjuvants for formulation, such as antioxidants, colorants, perfumes, potency enhancers and safeners .
Examples of the antioxidant include 3-/2-t-butyl-4-hydroxyanisol andbutylatedhydroxytoluene, and examples of the colorant include Rhodamine B, Yellow No. 4, Blue No. 1 and Red No. 2.
The amount of the adjuvants for formulation contained in the emulsifiable concentrate of the present invention is generally in a range from 0 to 5% by weight in total based on the total amount of the pesticide emulsifiable concentrate of the present invention.
Aspects of the pesticide emulsifiable concentrate of the present invention are as follows.
A pesticide emulsifiable concentrate, which comprises 1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight of the present hydrophobic organic solvent;
10 to 55 parts by weight of a hydrophilic organic solvent; 4 to 25 parts by weight of a surfactant; and 0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, which comprises 1 to 10 parts by weight of the present acetonitrile compound; 20 to 80 parts by weight of the present hydrophobic organic solvent;
15 to 45 parts by weight of a hydrophilic organic solvent; 5 to 20 parts by weight of a surfactant; and 0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, 'which comprises
3 to 7 parts by weight of the present acetonitrile compound; 20 to 75 parts by weight of the present hydrophobic organic solvent;
15 to 40 parts by weight of a hydrophilic organic solvent;
5 to 20 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 4:6 to 9:1.
A pesticide emulsifiable concentrate, which essentially consists of:
1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight of the present hydrophobic organic solvent;
10 to 55 parts by weight of a hydrophilic organic solvent;
4 to 25 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 4:6 to 8:2.
A pesticide emulsifiable concentrate, which essentially consists of: 1 to 10 parts by weight of the present acetonitrile compound;
20 to 80 parts by weight of the present hydrophobic organic solvent;
15 to 45 parts by weight of a hydrophilic organic solvent;
5 to 20 parts by weight of a surfactant; and 0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 4:6 to 8:2.
A pesticide emulsifiable concentrate, which essentially consists of: 3 to 7 parts by weight of the present acetonitrile compound;
20 to 75 parts by weight of the present hydrophobic organic solvent;
15 to 40 parts by weight of a hydrophilic organic solvent;
5 to 20 parts by weight of a surfactant; and 0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 4:6 to 8:2.
A pesticide emulsifiable concentrate, which comprises 1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight of the present hydrophobic organic solvent;
10 to 55 parts by weight of a hydrophilic organic solvent; and 4 to 25 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, which comprises
1 to 10 parts by weight of the present acetonitrile compound; 20 to 80 parts by weight of the present hydrophobic organic solvent;
15 to 45 parts by weight of a hydrophilic organic solvent; and
5 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, which comprises
3 to 7 parts by weight of the present acetonitrile compound;
20 to 75 parts by weight of the present hydrophobic organic solvent; 15 to 40 parts by weight of a hydrophilic organic solvent; and
5 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 4:6 to 9:1.
A pesticide emulsifiable concentrate, which essentially consists of:
1 to 10 parts by weight of the present acetonitrile compound;
10 to 80 parts by weight of the present hydrophobic organic solvent;
10 to 55 parts by weight of a hydrophilic organic solvent; and 4 to 25 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 4:6 to 8:2.
A pesticide emulsifiable concentrate, which essentially consists of: 1 to 10 parts by weight of the present acetonitrile compound;
20 to 80 parts by weight of the present hydrophobic organic solvent;
15 to 45 parts by weight of a hydrophilic organic solvent; and 5 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 4:6 to 8:2.
A pesticide emulsifiable concentrate, which essentially consists of: 3 to 7 parts by weight of the present acetonitrile compound;
20 to 75 parts by weight of the present hydrophobic organic solvent;
15 to 40 parts by weight of a hydrophilic organic solvent; and
5 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 4 : 6 to 8:2.
A pesticide emulsifiable concentrate, which comprises 1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight of diethyl oxalate;
10 to 55 parts by weight of a hydrophilic organic solvent; and
4 to 25 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 3:7 to 9:1. A pesticide emulsifiable concentrate, which comprises 3 to 7 parts by weight of the present acetonitrile compound; 20 to 75 parts by weight of diethyl oxalate; 15 to 40 parts by weight of a hydrophilic organic solvent; and
5 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, which essentially consists of: 1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight of diethyl oxalate; 10 to 55 parts by weight of a hydrophilic organic solvent; and
4 to 25 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 4 : 6 to 8:2.
A pesticide emulsifiable concentrate, which essentially consists of:
3 to 7 parts by weight of the present acetonitrile compound;
20 to 75 parts by weight of diethyl oxalate; 15 to 40 parts by weight of a hydrophilic organic solvent; and
5 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 4:6 to 8:2.
A pesticide emulsifiable concentrate, which comprises
1 to 10 parts by weight of the present acetonitrile compound;
5 to 80 parts by weight of diethyl oxalate;
0 to 35 parts by weight of other hydrophobic organic solvents;
10 to 55 parts by weight of a hydrophilic organic solvent; and 4 to 25 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, which comprises
3 to 7 parts by weight of the present acetonitrile compound; 20 to 80 parts by weight of diethyl oxalate;
0 to 35 parts by weight of other hydrophobic organic solvents; 15 to 40 parts by weight of a hydrophilic organic solvent; and 5 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, which essentially consists of:
1 to 10 parts by weight of the present acetonitrile compound; 5 to 80 parts by weight of diethyl oxalate;
0 to 35 parts by weight of other hydrophobic organic solvents; 10 to 55 parts by weight of a hydrophilic organic solvent; and
4 to 25 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 4 : 6 to 8:2.
A pesticide emulsifiable concentrate, which essentially consists of:
3 to 7 parts by weight of the present acetonitrile compound;
20 to 80 parts by weight of diethyl oxalate; 0 to 35 parts by weight of other hydrophobic organic solvents;
15 to 40 parts by weight of a hydrophilic organic solvent; and
5 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 4:6 to 8:2.
A pesticide emulsifiable concentrate, which comprises
1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight of diethyl oxalate;
10 to 55 parts by weight of a hydrophilic organic solvent selected from the group consisting of N-methyl pyrrolidone and 1, 3-dimethyl-2-imidazolidinone; and
4 to 25 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 4:6 to .9:1.
A pesticide emulsifiable concentrate, which essentially consists of:
1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight of diethyl oxalate; 10 to 55 parts by weight of a hydrophilic organic solvent selected from the group consisting of N-methyl pyrrolidone and 1, 3-dimethyl-2-imidazolidinone; and
4 to 25 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, which comprises
3 to 7 parts by weight of the present acetonitrile compound;
20 to 75 parts by weight of diethyl oxalate;
0 to 20 parts by weight of aromatic hydrocarbon; 15 to 40 parts by weight of a hydrophilic organic solvent selected from the group consisting of N-methyl pyrrolidone and
1, 3-dimethyl-2-imidazolidinone; and
5 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, which essentially consists of:
3 to 7 parts by weight of the present acetonitrile compound; 20 to 75 parts by weight of diethyl oxalate; 0 to 20 parts by weight of aromatic hydrocarbon; 15 to 40 parts by weight of a hydrophilic organic solvent selected from the group consisting of N-methyl pyrrolidone and 1, 3-dimethyl-2-imidazolidinone; and 5 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to a hydrophilic organic solvent is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, which comprises 1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight of diethyl oxalate; 10 to 55 parts by weight of 1, 3-dimethyl-2-imidazolidinone;
4 to 25 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to
1, 3-dimethyl-2-imidazolidinone is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, which comprises
3 to 7 parts by weight of the present acetonitrile compound;
20 to 75 parts by weight of diethyl oxalate; 15 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone;
5 to 20 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to 1, 3-dimethyl~2-imidazolidinone is from 4:6 to 9:1. A pesticide emulsifiable concentrate, which essentially consists of:
1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight ,of diethyl oxalate;
10 to 55 parts by weight of 1, 3-dimethyl-2-imidazolidinone; 4 to 25 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to 1, 3-dimethyl-2-imidazolidinone is from 4:6 to 8:2. A pesticide emulsifiable concentrate, which essentially consists of:
3 to 7 parts by weight of the present acetonitrile compound; 20 to 75 parts by weight of diethyl oxalate; 15 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone; 5 to 20 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to 1, 3-dimethyl-2-imidazolidinone is from 4:6 to 8:2.
A pesticide emulsifiable concentrate, which comprises 1 to 10 parts by weight of the present acetonitrile compound; 20 to 80 parts by weight of diethyl oxalate; 10 to 45 parts by weight of 1, 3-dimethyl-2-imidazolidinone;
5 to 20 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to
1, 3-dimethyl-2-imidazolidinone is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, which essentially consists of:
1 to 10 parts by weight of the present acetonitrile compound; 20 to 80 parts by weight of diethyl oxalate;
10 to 45 parts by weight of 1, 3-dimethyl-2-imidazolidinone; 5 to 20 parts by weight of a surfactant; and 0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to 1, 3-dimethyl-2-imidazolidinone is from 4:6 to 8:2.
A pesticide emulsifiable concentrate, which comprises 1 to 10 parts by weight of the present acetonitrile compound; 5 to 80 parts by weight of diethyl oxalate;
0 to 35 parts by weight of aromatic hydrocarbon;
10 to 55 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and
4 to 25 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to 1, 3-dimethyl-2-imidazolidinone is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, which essentially consists of:
1 to 10 parts by weight of the present acetonitrile compound;
5 to 80 parts by weight of diethyl oxalate; 0 to 35 parts by weight of aromatic hydrocarbon;
10 to 55 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and
4 to 25 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to 1, 3-dimethyl-2-imidazolidinone is from
4:6 to 8:2. A pesticide emulsifiable concentrate, which comprises
3 to 7 parts by weight of the present acetonitrile compound;
20 to 80 parts by weight of diethyl oxalate;
0 to 35 parts by weight of aromatic hydrocarbon;
10 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and 5 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to 1, 3~dimethyl-2-imidazolidinone is from
3:7 to 9:1.
A pesticide emulsifiable concentrate, which essentially consists of: 3 to 7 parts by weight of the present acetonitrile compound; 20 to 80 parts by weight of diethyl oxalate; 0 to 35 parts by weight of aromatic hydrocarbon; 10 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and 5 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to 1, 3-dimethyl-2-imidazolidinone is from 4:6 to 8:2.
A pesticide emulsifiable concentrate, which comprises 1 to 10 parts by weight of the present acetonitrile compound;
40 to 65 parts by weight of the present hydrophobic organic solvent;
25 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone;
10 to 20 parts by weight of a surfactant; and 0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to
1, 3-dimethyl-2-imidazolidinone is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, which comprises
3 to 7 parts by weight of the present acetonitrile compound; 40 to 65 parts by weight of the present hydrophobic organic solvent;
25 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone;
10 to 20 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to
1, 3-dimethyl-2-imidazolidinone is from 4:6 to 9:1.
A pesticide emulsifiable concentrate, which essentially consists of:
1 to 10 parts by weight of the present acetonitrile compound; 40 to 65 parts by weight of the present hydrophobic organic solvent;
25 to 40 parts by weight of 1, 3-dimethyl-2~imidazolidinone;
10 to 20 parts by weight of a surfactant; and 0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to
1, 3-dimethyl-2-imidazolidinone is from 4:6 to' 8:2.
A pesticide emulsifiable concentrate, which essentially consists of: 3 to 7 parts by weight of the present acetonitrile compound;
40 to 65 parts by weight of the present hydrophobic organic solvent;
25 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone;
10 to 20 parts by weight of a surfactant; and 0 to 5 parts by weight of adjuvants for formulation, wherein the weight ratio of diethyl oxalate to
1, 3-dimethyl-2-imidazolidinone is from 4:6 to 8:2.
A pesticide emulsifiable concentrate, which comprises 1 to 10 parts by weight of the present acetonitrile compound;
20 to 30 parts by weight of diethyl oxalate;
20 to 35 parts by weight of aromatic hydrocarbon;
25 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and
10 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to 1, 3-dimethyl-2-imidazolidinone is from 3:7 to 9:1.
A pesticide emulsifiable concentrate, which essentially consists of:
1 to 10 parts by weight of the present acetonitrile compound; 20 to 30 parts by weight of diethyl oxalate;
20 to 35 parts by weight of aromatic hydrocarbon;
25 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and
10 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to 1, 3-dimethyl-2-imidazolidinone is from 4:6 to 8:2.
A pesticide emulsifiable concentrate, which comprises
3 to 7 parts by weight of the present acetonitrile compound;
20 to 30 parts by weight of diethyl oxalate; 20 to 35 parts by weight of aromatic hydrocarbon;
25 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and
10 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to 1, 3-dimethyl-2-imidazolidinone is from 3:7 to 9:1. A pesticide emulsifiable concentrate, which essentially consists of:
3 to 7 parts by weight of the present acetonitrile compound; 20 to 30 parts by weight of diethyl oxalate;
20 to 35 parts by weight of aromatic hydrocarbon; 10 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and
10 to 20 parts by weight of a surfactant, wherein the weight ratio of diethyl oxalate to 1, 3-dimethyl-2-imidazolidinone is from 4:6 to 8:2.
A pesticide emulsifiable concentrate, which comprises 1 to 10 parts by weight of the present acetonitrile compound;
10 to 80 parts by weight of diethyl oxalate;
10 to 55 parts by weight of 1, 3-dimethyl-2-imidazolidinone;
4 to 25 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation. A pesticide emulsifiable concentrate, which comprises
3 to 7 parts by weight of the present acetonitrile compound; 20 to 75 parts by weight of diethyl oxalate;
15 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone; 5 to 20 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation.
A pesticide emulsifiable concentrate, which essentially consists of:
1 to 10 parts by weight of the present acetonitrile compound; 10 to 80 parts by weight of diethyl oxalate;
10 to 55 parts by weight of 1, 3-dimethyl-2-imidazolidinone;
4 to 25 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation.
A pesticide emulsifiable concentrate, which essentially consists of:
3 to 7 parts by weight of the present acetonitrile compound;
20 to 75 parts by weight of diethyl oxalate;
15 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone;
5 to 20 parts by weight of a surfactant; and 0 to 5 parts by weight of adjuvants for formulation.
A pesticide emulsifiable concentrate, which comprises
1 to 10 parts by weight of the present acetonitrile compound; 20 to 80 parts by weight of diethyl oxalate;
10 to 45 parts by weight of 1, 3-dimethyl-2-imidazolidinone; 5 to 20 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation.
A pesticide emulsifiable concentrate, which essentially consists of:
1 to 10 parts by weight of the present acetonitrile compound; 20 to 80 parts by weight of diethyl oxalate;
10 to.45 parts by weight of 1, 3-dimethyl-2-imidazolidinone;
5 to 20 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation.
A pesticide emulsifiable concentrate, which comprises
1 to 10 parts by weight of the present acetonitrile compound; 5 to 80 parts by weight of diethyl oxalate;
0 to 35 parts by weight of aromatic hydrocarbon; 10 to 55 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and 4 to 25 parts by weight of a surfactant.
A pesticide emulsifiable concentrate, which essentially consists of:
1 to 10 parts by weight of the present acetonitrile compound; 5 to 80 parts by weight of diethyl oxalate;
0 to 35 parts by weight of aromatic hydrocarbon;
10 to 55 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and
4 to 25 parts by weight of a surfactant.
A pesticide emulsifiable concentrate, which comprises 3 to 7 parts by weight of the present acetonitrile compound; 20 to 80 parts by weight of diethyl oxalate; 0 to 35 parts by weight of aromatic hydrocarbon; 10 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and
5 to 20 parts by weight of a surfactant. A pesticide emulsifiable concentrate, which essentially consists of:
3 to 7 parts by weight of the present acetonitrile compound; 20 to 80 parts by weight of diethyl oxalate; 0 to 35 parts by weight of aromatic hydrocarbon; 10 to 40 parts by weight of 1, 3-dimethyl-2-imidazolidinone; and 5 to 20 parts by weight of a surfactant.
The pesticide emulsifiable concentrate of the present invention can be prepared, for example, by adding the present acetonitrile compound to a mixture of the present hydrophobic organic solvent and a hydrophilic organic solvent under optionally heating condition (800C or lower), and adding a surfactant (and adjuvants for formulation, if necessary) , followed by uniformly stirring and optionally filtering.
After preparation, the pesticide emulsifiable concentrate of the present invention is filled in a vessel such as a bottle made of polyethylene or polyethylene terephthalate, .or a metal can. Since the pesticide emulsifiable concentrate of the present invention is not separated into two layers even when it absorbs a small amount of moisture during storage, a uniform pesticide emulsifiable concentrate can be taken out of a vessel when used.
The pesticide emulsifiable concentrate of the present invention is generally diluted with water, and used by spraying the aqueous dilute solution over crops . In that case, an aqueous dilute solution, which is obtained by dilution of the pesticide emulsifiable concentrate of the present invention with water, is prepared by diluting the pesticide emulsifiable concentrate of the present invention with water generally from 10 to 10, 000 times so as for the concentration of the present acetonitrile compound to be approximately fromO .1 to 1, 000 ppm, andpreferably approximately from 1 to 500 ppm. Water used for the preparation may generally be either soft water or hard water, and an adjuvant such as a spreader can be added thereto if necessary. The pesticide emulsifiable concentrate of the present invention has good emulsion stability when it is diluted with water. The application amount of the aqueous dilute solution, which is obtained by dilution of the pesticide emulsifiable concentrate of the present invention, is generally from 0.1 to 10,000 g, preferably from 1 to 250 g, per hectare as an amount of the present acetonitrile compound.
EXAMPLES
The present invention will now be described in more detail by way of Preparation Examples and Test Examples , but the present invention is not limited to these Examples. Preparation Example 1
The present acetonitrile compound (2.0 g in terms of pure component), calcium dodecylbenzene sulfonate (Rhodacal 70, manufactured by RHODIA; 4.00 g) , polyoxyethylene polyoxypropylene tristyrylphenyl ether (Soprophor 796/P, manufactured by RHODIA; 3.00 g) and 1, 3-dimethyl-2-imidazolidinone (45.0Og) were weighed in a 100 ml volumetric flask at 200C, and diethyl oxalate (an amount equivalent to 53 g) was added thereto to make 100 ml in total. The mixture was stirred until the solution became uniform under heating to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 1 of the present invention) . Preparation Example 2
The present acetonitrile compound (2.0 g in terms of pure component) , calcium dodecylbenzene sulfonate (Rhodacal 70, manufactured by RHODIA; 5.60 g) , polyoxyethylene polyoxypropylene tristyrylphenyl ether (Soprophor 796/P, manufactured by RHODIA; 1.4 g) and 1, 3-dimethyl-2-imidazolidinone (45.00 g) were weighed in a 100 ml volumetric flask at 2O0C, and diethyl oxalate (an amount equivalent to 53 g) was added thereto to make 100 ml in total. The mixture was stirred until the solution became uniform under heating to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 2 of the present invention) .
Preparation Example 3
The present acetonitrile compound ( 5.0 g in terms of pure component) , calcium dodecylbenzene sulfonate (NANSA EVM 62/H, manufactured by HUNTSMAN; 5.60 g) , polyoxyethylene polyoxypropylene block polymer (TOXIMUL 8320, manufactured by STEPAN; 6.4O g), 1, 3-dimethyl-2-imidazolidinone (30.0O g) and aromatic 'hydrocarbon (mainly CIl to C14 alkylnaphthalene, Solvesso 200 ND, manufactured by EXXON MOBIL CHEMICAL COMPANY; 10.00 g) were weighed in a 100 ml volumetric flask at 200C, and diethyl oxalate (an amount equivalent to 51 g) was added thereto to make 100 ml in total. The mixture was stirred until the solution became uniform under heating to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 3 of the present invention) . Preparation Example 4
The present acetonitrile compound (5.0 g in terms of pure component) , calcium dodecylbenzene sulfonate (NANSA EVM 62/H, manufactured by HUNTSMAN; 5.80 g) , polyoxyethylene polyoxypropylene block polymer (TOXIMUL 8320, manufactured by STEPAN; 6.20 g) , 1, 3-dimethyl-2-imidazolidinone (30.00 g) and aromatic hydrocarbon (mainly ClI to C14 alkylnaphthalene, Solvesso 200 ND, manufactured by EXXON MOBIL CHEMICAL COMPANY; 15.00 g) were weighed in a 100 ml volumetric flask at 200C, and diethyl oxalate (an amount equivalent to 45 g) was added thereto to make 100 ml in total. The mixture was stirred until the solution became uniform under heating to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 4 of the present invention) .
Preparation Example 5
The present acetonitrile compound (10.00 g in terms of pure component) was added to a mixture of diethyl oxalate (45 g) and N-methyl pyrrolidone (35 g) and dissolved therein at 200C. Then Solpol 3005X (manufactured by TOHO KAGAKU; 10 g) was added thereto and stirred to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 5 of the present invention) .
Preparation Example 6
The present acetonitrile compound (5.0 g in terms of pure component) , calcium dodecylbenzene sulfonate (NANSA EVM 62/H, manufactured by HUNTSMAN; 10.0 g) , polyoxyethylene alkyl ether
(MAKON DA-6, manufactured by STEPAN; 10.0 g) ,
1, 3-dimethyl-2-imidazolidinone (30.00 g) and aromatic hydrocarbon (mainly ClO to CIl alkylnaphthalene, Solvesso 150, manufactured by EXXON MOBIL CHEMICAL COMPANY; 20.00 g) were weighed in a 100 ml volumetric flask at 200C, and diethyl oxalate
(an amount equivalent to 30 g) was added thereto to make 100 ml in total. The mixture was stirred until the solution became uniform under heating to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 6 of the present invention) .
Preparation Example 7
The present acetonitrile compound (3.0 g in terms of pure component) , calcium dodecylbenzene sulfonate (NANSA EVM 62/H, manufactured by HUNTSMAN; 5.0 g) , sorbitan fatty acid ester
(ALKAMULS T/85-V, manufactured by RHODIA; 5.00 g) ,
1, 3-dimethyl-2-imidazolidinone (15.00 g) and xylene (15.00 g) were weighed in a 100 ml volumetric flask at 200C, and diethyl oxalate (an amount equivalent to 62 g) was added thereto to make 100 ml in total. The mixture was stirred until the solution became uniform under heating to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 7 of the present invention) .
Preparation Example 8
The present acetonitrile compound (5.0 g in terms of pure component) , calcium dodecylbenzene sulfonate (NANSA EVM 62/H, manufactured by HUNTSMAN; 5.00 g) , polyoxyethylene polyoxypropylene block polymer (TOXIMUL 8320, manufactured by STEPAN; 7.00 g) , 1, 3-dimethyl-2-imidazolidinone (30.00 g) and aromatic hydrocarbon (mainly CIl to C14 alkylnaphthalene, Solvesso 200 ND, manufactured by EXXON MOBIL CHEMICAL COMPANY; 30.00 g) were weighed in a 100 ml volumetric flask at 200C, and diethyl oxalate (an amount equivalent to 28 g) was added thereto to make 100 ml in total. The mixture was stirred until the solution became uniform under heating to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 8 of the present invention) .
Preparation Example 9
The present acetonitrile compound (5.0 g in terms of pure component) , calcium dodecylbenzene sulfonate (NANSA EVM 62/H, manufactured by HUNTSMAN; 7.00 g) , polyoxyethylene castor oil
(TOXIMUL 8240, manufactured by STEPAN; 8.00 g) ,
1, 3-dimethyl~2-imidazolidinone (30.00 g) and aromatic hydrocarbon (mainly CIl to C14 alkylnaphthalene, Solvesso 200, manufactured by EXXON MOBIL CHEMICAL COMPANY; 30.00 g) were weighed in a 100 ml volumetric flask at 2O0C, and diethyl oxalate
(an amount equivalent to 25 g) was added thereto to make 100 ml in total. The mixture was stirred until the solution became uniform under heating to obtain a pesticide emulsifiable concentrate of the present invention (hereafter referred to as the emulsifiable concentrate 9 of the present invention) .
Comparative Preparation Example 1
The present acetonitrile compound (10.00 g in terms of pure component) was added to a mixture of aromatic hydrocarbon (mainly ClO to ClI alkylbenzene, Solvesso 150, manufactured by
EXXON MOBIL CHEMICAL COMPANY; 45 g) and N-methyl pyrrolidone
(35 g) and dissolved at 200C. Then Solpol 3005X (manufactured by TOHO KAGAKU; 10 g) was added thereto and stirred to obtain a pesticide emulsifiable concentrate (hereafter referred to as the comparative emulsifiable concentrate 1) .
Test Example 1 10 g of a pesticide emulsifiable concentrate and 1 g of pure water were placed in a 20 ml ampoule tube (manufactured by MARUEMU, screw tube No. 5) and intensively stirred. After stirring, the tube was allowed to stand for one hour, and visual observation of the mixture was conducted to confirm the presence or absence of separation in the liquid phase. The results are shown in Table 1.
Table 1
Pesticide Emulsifiable Presence or Absence of Concentrate Separation in Liquid Phase
The Εmulsifiable Concentrate 1 Absent (yellow as a whole) of the Present Invention
The Emulsifiable Concentrate 2 Absent (yellow as a whole) of the Present Invention
The Emulsifiable Concentrate 3 Absent (yellow as a whole) of the Present Invention
The Emulsifiable Concentrate 4 Absent (yellow as a whole) of the Present Invention
The Emulsifiable Concentrate 5 Absent (yellow as a whole) of the Present Invention
The Emulsifiable Concentrate 6 Absent (yellow as a whole', of the Present Invention
The Comparative Emulsifiable Present (1.4 cm high colorless Concentrate 1 layer (upper layer) and 1.1 cm high yellow layer (lower layer) )
Test Example 2
10 g of a pesticide emulsifiable concentrate and 0.5 g of pure water were placed in a 20 ml ampoule tube (manufactured by MARUEMU, screw tube No. 5) and intensively stirred. After stirring, the tube was allowed to stand for one hour, and visual observation of the mixture was conducted to confirm the presence or absence of separation in the liquid phase. The results are shown in Table 2. Table 2
Pesticide Emulsifiable Presence or Absence of Concentrate Separation in Liquid Phase
The Emulsifiable Concentrate 1 Absent (yellow as a whole) of the Present Invention
The Emulsifiable Concentrate 2 Absent (yellow as a whole) of the Present Invention
The Emulsifiable Concentrate 3 Absent (yellow as a whole) of the Present Invention
The Emulsifiable Concentrate 4 Absent (yellow as a whole) of the Present Invention
The Emulsifiable Concentrate 5 Absent (yellow as a whole] of the Present Invention
The Emulsifiable Concentrate 6 Absent (yellow as a whole) of the Present Invention
The Emulsifiable Concentrate 7 Absent (yellow as a whole) of the Present Invention
The Emulsifiable Concentrate 8 Absent (yellow as a whole) of the Present Invention
The Emulsifiable Concentrate 9 Absent (yellow as a whole) of the Present Invention
The Comparative Emulsifiable Present (1.1 cm high colorless Concentrate 1 layer (upper layer) and 1.1 cm high yellow layer (lower layer) )
Next, the pesticide emulsifiable concentrate of the present invention was diluted with water to prepare an aqueous dilute solution, and the emulsion state was observed. Test Example 3
1 ml of each of the emulsifiable concentrates 1 to 9 of the present invention was measured in a 100 ml volumetric cylinder with a stopper, and CIPAC standard water D (342 ppm) was added thereto to make 100 ml in total, and thereby an aqueous dilute solution of thepesticide emulsifiable concentrate of thepresent invention was prepared. All the aqueous dilute solutions of the emulsifiable concentrates 1 to 9 of the present invention showed good emulsion state.
INDUSTRIAL APPLICABILITY
The pesticide emulsifiable concentrate of the present invention has good storage stability so as not to separate into two layers even when it absorbs a small amount of moisture, and is also excellent in emulsion stability when diluted with water .

Claims

1. A pesticide emulsifiable concentrate comprising 2- [ (2-fluoro-5-trifluoromethyl) phenylthio] -2- [3- (2-methoxyp henyl) -2-thiazolydinyliden] acetonitrile, a hydrophobic organic solvent containing diethyl oxalate, a hydrophilic organic solvent and a surfactant, wherein the weight ratio of diethyl oxalate to the hydrophilic organic solvent is in a range from 3:7 to 9:1.
2. The pesticide emulsifiable concentrate according, to claim 1, wherein the weight ratio of diethyl oxalate to the hydrophilic organic solvent is in a range from 4:6 to 8:2.
3. The pesticide emulsifiable concentrate according to claim 1, wherein other hydrophobic organic solvents other than diethyl oxalate are aromatic hydrocarbons .
4. The pesticide emulsifiable concentrate according to claim 1, wherein the hydrophilic organic solvent is at least one kind of an organic solvent selected from the group consisting of N,N-dimethyl acetamide, N,N-dimethyl propionamide, N,N-dimethyl formamide, N-methyl pyrrolidone, N-ethyl pyrrolidone, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide.
5. The pesticide emulsifiable concentrate according to claim 1, wherein the surfactant is an anionic surfactant and a nonionic surfactant, and the weight ratio of the anionic surfactant to the nonionic surfactant is from 1:0.1 to 1:10.
6. The pesticide emulsifiable concentrate according to claim 1, which essentially consists of: 1 to 10 parts by weight of 2- [ (2-fluoro-5-trifluoromethyl) phenylthio] -2- [3- (2-methoxyp henyl) -2-thiazolydinyliden] acetonitrile;
10 to 80 parts by weight of a hydrophobic organic solvent containing diethyl oxalate; 10 to 55 parts by weight of a hydrophilic organic solvent;
4 to 25 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation.
7. The pesticide emulsifiable concentrate according to claim 1, which essentially consists of:
3 to 7 parts by weight of
2- [ (2-fluoro-5-trifluoromethyl) phenylthio] -2- [3- (2-methoxyp henyl) -2-thiazolydinyliden] acetonitrile;
20 to 80 parts by weight of a hydrophobic organic solvent containing diethyl oxalate;
15 to 45 parts by weight of a hydrophilic organic solvent;
5 to 20 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation.
8. The pesticide emulsifiable concentrate according to claim 1, which essentially consists of:
1 to 10 parts by weight of 2- [ (2-fluoro-5-trifluoromethyl) phenylthio] -2- [3- (2-methoxyp henyl) -2-thiazolydinyliden] acetonitrile; 5 to 80 parts by weight of diethyl oxalate;
0 to 35 parts by weight of other hydrophobic organic solvents other than diethyl oxalate;
10 to 55 parts by weight of a hydrophilic organic solvent; 4 to 25 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation.
9. The pesticide emulsifiable concentrate according to claim 1, which essentially consists of: 1 to 10 parts ' by weight of
2- [ (2-fluoro-5-trifluoromethyl) phenylthio] -2- [3- (2-methoxyp henyl) -2-thiazolydinyliden] acetonitrile;
20 to 80 parts by weight of diethyl oxalate;
0 to 35 parts by weight of other hydrophobic organic solvents other than diethyl oxalate;
10 to 55 parts by weight of a hydrophilic organic solvent;
4 to 25 parts by weight of a surfactant; and
0 to 5 parts by weight of adjuvants for formulation.
10. An agueous dilute solution prepared by diluting the pesticide emulsifiable concentrate according to claim 1 with water by 10 to 10,000 times.
PCT/JP2007/064725 2006-07-24 2007-07-20 Pesticide emulsifiable concentrate Ceased WO2008013249A1 (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008047569A3 (en) * 2006-09-27 2009-01-15 Sumitomo Chemical Co Agrochemical composition comprising as solvent a mixture of an aromatic hydrocarbon, diethyloxalate, and 1,3-dimethyl-2-imidazolidinone
WO2013040006A1 (en) 2011-09-12 2013-03-21 Rhodia Operations Agricultural pesticide compositions
CN104955331A (en) * 2013-01-29 2015-09-30 日产化学工业株式会社 Emulsifying pesticide composition having high emulsion stability

Citations (2)

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US6710062B1 (en) * 1999-12-24 2004-03-23 Otsuka Chemical Co., Ltd. Cyanomethylene compounds, process for producing the same, and agricultural or horticultural bactericide
US20040097378A1 (en) * 2001-02-22 2004-05-20 Thomas Maier Agrochemical formulations

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6710062B1 (en) * 1999-12-24 2004-03-23 Otsuka Chemical Co., Ltd. Cyanomethylene compounds, process for producing the same, and agricultural or horticultural bactericide
US20040097378A1 (en) * 2001-02-22 2004-05-20 Thomas Maier Agrochemical formulations

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008047569A3 (en) * 2006-09-27 2009-01-15 Sumitomo Chemical Co Agrochemical composition comprising as solvent a mixture of an aromatic hydrocarbon, diethyloxalate, and 1,3-dimethyl-2-imidazolidinone
WO2013040006A1 (en) 2011-09-12 2013-03-21 Rhodia Operations Agricultural pesticide compositions
EP2755476A4 (en) * 2011-09-12 2014-12-17 Rhodia Operations AGRICULTURAL PESTICIDE COMPOSITIONS
CN104955331A (en) * 2013-01-29 2015-09-30 日产化学工业株式会社 Emulsifying pesticide composition having high emulsion stability

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