AU2011201960A1 - Emulsifiable concentrate - Google Patents

Emulsifiable concentrate Download PDF

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AU2011201960A1
AU2011201960A1 AU2011201960A AU2011201960A AU2011201960A1 AU 2011201960 A1 AU2011201960 A1 AU 2011201960A1 AU 2011201960 A AU2011201960 A AU 2011201960A AU 2011201960 A AU2011201960 A AU 2011201960A AU 2011201960 A1 AU2011201960 A1 AU 2011201960A1
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weight
emulsifiable concentrate
octanoate
aromatic hydrocarbon
surfactant
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AU2011201960A
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AU2011201960B2 (en
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Yumiko Kozuki
Naoki Tsuda
Kazuyuki Yanagisawa
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Priority claimed from JP2005275323A external-priority patent/JP2006306830A/en
Priority claimed from JP2005281349A external-priority patent/JP2007091619A/en
Priority claimed from JP2005286832A external-priority patent/JP2007091691A/en
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to AU2011201960A priority Critical patent/AU2011201960B2/en
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents

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

Description

S&F Ref: 753620D2 AUSTRALIA PATENTS ACT 1990 COMPLETE SPECIFICATION FOR A STANDARD PATENT Name and Address Sumitomo Chemical Company, Limited, of 27-1, of Applicant: Shinkawa 2-chome, Chuo-ku, Tokyo, 104-8260, Japan Actual Inventor(s): Kazuyuki Yanagisawa Naoki Tsuda Yumiko Kozuki Address for Service: Spruson & Ferguson St Martins Tower Level 35 31 Market Street Sydney NSW 2000 (CCN 3710000177) Invention Title: Emulsifiable concentrate The following statement is a full description of this invention, including the best method of performing it known to me/us: 5845c(3971531_1) 1 EMULSIFIABLE CONCENTRATE FIELD OF THE INVENTION The present invention relates to a pesticidal emulsifiable 5 concentrate which contains 2',4'-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide as a herbicidal active ingredient. BACKGROUND ART 10 It is known that 2',4'-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide shown by the below formula is an active ingredient of herbicide in USP-4618366.
CF
3 N H F N F 15 DISCLOSURE OF THE INVENTION The present invention provides an emulsifiable concentrate containing 2', 4' -difluoro-2- (a,a,a-trifluoro-m-tolyloxy)nicotinanilide 20 as a herbicidal active ingredient which has an excellent stability of the emulsion even after diluted with water. According to the present invention, an emulsifiable concentrate containing 2',4'-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide, 25 the compound shown by the formula (1): 2 S A OR2 0 0 wherein, in the formula, R1 and R2 represent alkyl groups, A represents a single bond or an alkylene group, and the sum of the number of carbon atoms which consist of the groups of R', 5 R2 and A is 2 to 8; and a surf actant has an excellent stability of the emulsion even after diluted with water. Namely, the present invention is as follows: 10 [1] An emulsifiable concentrate, which is characterized by comprising 2',4' -difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide; the compound shown by the below formula (1): Ri O A ( ,R 2 (1) o 0 15 wherein, in the formula, R' and R 2 represent alkyl groups, A represents a single bond or an alkylene group, and the sum of the number of carbon atoms which consist of the groups of R',
R
2 and A is 2 to 8; and a surfactant. 20 [2] An emulsifiable concentrate, which is characterized by comprising 0.5 to 5 % by weight of 2', 4 -difluoro-2- (a,a,a-trifluoro-m-tolyloxy)nicotinanilide; 5 to 80 % by weight of the compound shown by the below formula 25 (1): 3 A 0 0 0 wherein, in the formula, R1 and R 2 represent alkyl groups, A represents a single bond or an alkylene group, and the sum of the number of carbon atoms which consist of the groups of R', 5 R2 and A is 2 to 8; and 4 to 20 % by weight of a surfactant. [3] The emulsifiable concentrate according to [1] or [2], wherein the compound shown by the formula (1) is diethyl oxalate. 10 [4] The emulsifiable concentrate according to any one of [1] to [3], wherein the ratio of the compound shown by the formula (1) is 5 to 80 by weight for one weight of 2' ,4'-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide. [5] The emulsifiable concentrate according to any one 15 of [1] to [41, wherein the emulsifiable concentrate comprises an aromatic hydrocarbon. [6] The emulsifiable concentrate according to any one of [1] to [41, wherein the emulsifiable concentrate comprises 1 to 40 % by weight of an aromatic hydrocarbon. 20 [7] The emulsifiable concentrate according to any one of [1] to [6], wherein the emulsifiable concentrate comprises 1,3-dimethyl-2-imidazolidinone. [8] The emulsifiable concentrate according to any one of [1] to [61, wherein the emulsifiable concentrate comprises 25 5 to 60 by weight of 1,3-dimethyl-2-imidazolidinone. [9] The emulsifiable concentrate according to any one of [1] to [8], wherein the surfactant is an anionic surfactant 4 and a nonionic surfactant; and the ratio by weight of the anionic surfactant and the nonionic surfactant is 1:0.1 to 1:10. [10] The emulsifiable concentrate according to [9], wherein the anionic surfactant is an alkylbenzenesulfonic acid 5 salt. [11] The emulsifiable concentrate according to [91 or [10 ], wherein the nonionic surfactant is the nonionic surf actant which has polyalkylene oxide structure in the molecule. [12] The emulsifiable concentrate according to [11], 10 wherein the nonionic surfactant which has polyalkylene oxide structure in the molecule is the surfactant selected from the group consisting of polyoxyethylene-polyoxypropylene tristyryl phenyl ether, polyoxyethylene tristyryl phenyl ether and polyoxyethylene castor oil. 15 [13] The emulsifiable concentrate according to [9] or [10], wherein the nonionic surfactant is a sorbitan fatty acid ester. [141 The emulsifiable concentrate according to [1], wherein the emulsifiable concentrate comprises 20 4-cyano-2,6-dibromophenyl octanoate and 4-cyano-2,6-diiodophenyl octanoate. [15] The emulsifiable concentrate according to [2], wherein the emulsifiable concentrate comprises 1 to 30 % by weight of 4-cyano-2,6-dibromophenyl octanoate and 1 to 30 % by weight 25 of 4-cyano-2,6-diiodophenyl octanoate. [16] The emulsifiable concentrate according to [14] or [15], wherein the ratio of the compound shown by the formula (1) is 5 to 80 by weight for the weight of 2 ,4' -difluoro-2-(a,aa-trifluoro-m-tolyloxy)nicotinanilide.
5 [17] The emulsifiable concentrate according to any one of [14] to [16], wherein the surfactant is an anionic surfactant and a nonionic surfactant; and the ratio by weight of the anionic surfactant and the nonionic surfactant is 1:0.1 to 1:10. 5 [181. The emulsifiable concentrate according to any one of [111 to [14], wherein the compound shown by the formula (1) is diethyl oxalate. [19] The emulsifiable concentrate according to any one of [14] to [18], wherein the emulsifiable concentrate comprises 10 an aromatic hydrocarbon. [20] The emulsifiable concentrate, which is characterized by comprising 2',4'-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide; 1,3-dimethyl-2-imidazolidinone; 15 an aromatic hydrocarbon; and a surfactant. [21] The emulsifiable concentrate, which is characterized by comprising 1 to 5 % by weight of 20 2',4'-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide; 5 to 60 % by weight of 1,3-dimethyl-2-imidazolidinone; 10 to 50 % by weight of an aromatic hydrocarbon; and 4 to 20 % by weight of a surfactant. [22] The emulsifiable concentrate, which is 25 characterized by comprising 2',4'-difluoro-2-(a,ala-trifluoro-m-tolyloxy)nicoti-nanilide; a sorbitan fatty acid ester; an anionic surfactant; and an aromatic hydrocarbon.
6 [231 The emulsifiable concentrate, which is characterized by comprising 0.5 to 5 % by weight of 2' ,4' -difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotianilide; 5 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an anionic surfactant; and 10 to 90 % by weight of an aromatic hydrocarbon. [24] An aqueous composition which is obtainable by diluting the emulsifiable concentrate according to any one of 10 [1] to (23] with water. The emulsifiable concentrate of the present invention contains 2' , 4' -difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide 15 as a herbicidal active ingredient. The common name of 2', 4' -difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilde is diflufenican(referred as diflufenican, hereinafter). The emulsifiable concentrate of the present invention may 20 further contain another herbicidal active compound such as 4-cyano-2,6-dibromophenyl octanoate and 4-cyano-2,6-diiodophenyl octanoate. 4-cyano-2,6-dibromophenyl octanoate is the compound named bromoxynil octanoate as common name(referred as 25 bromoxynil=octanoate, hereinafter). 4-cyano-2,6-diiodophenyl octanoate is the compound named ioxynil octanoate as common name(referred as ioxynil=octanoate, hereinafter). Diflufenican is the compound disclosed in "The Pesticide 7 Manual" (by British Crop Protection Council, Thirteenth Edition) as reference number 251. It is a solid compound and its melting point is about 159 to 161 0 C. It can be produced by the method disclosed inUSP-4618366. Bromoxynil=octanoateis the compound 5 disclosed in " The Pesticide Manual" (mentioned above) as reference number 95. It is a solid compound and its melting point is about 45 to 46 0 C. It can be produced by the method disclosed in USP-3397054. Ioxynil=octanoate is the compound disclosed in "The Pesticide Manual" (mentioned above) as reference number 467. .0 It is a solid compound and its melting point is about 56 to 57 0 C. It can be produced by the method disclosed in USP-3397054. In the emulsifiable concentrate of the present invention, the amount of diflufenican is usually 0.5 to 5 % by weight, L5 preferably 1 to 5 % by weight, more preferably 1 to 4 % by weight and far more preferably 1.5 to 4 % by weight based on the total weight of the emulsifiable concentrate of the present invention. In case of the emulsifiable concentrate of the present invention contains bromoxynil=octanoate and/or 20 ioxynil=octanoate, the amount of bromoxynil=octanoate Ls usually ito 30 %byweight, preferably 6 to 20 %byweight andmore preferably 8 to 18 % by weight; and the amount of ioxynil=octanoate is usually 1 to 30 % byweight, pref erably 4 to 12 % byweight andmore preferably 4 to 10 % by weight based on the total weight of the emulsifiable 25 concentrate of the present invention. In this case, the total weight of diflufenican, bromoxynil=octanoate and ioxynil=octanoate is usually 1 to 60 % by weight, preferably 3 to 40 % by weight based on the total weight of the emulsifiable concentrate of the present invention.
8 The emulsifiable concentrate of the present invention contains the compound shown by the formula (1) as a solvent. The compound shown by the formula (1) can solve diflufenican. 5 Furthermore, the compound shown by the formula (1)(referred as the present solvent, hereinafter) is miscible with an organic solvent which is usually used for pesticidal formulation. In the formula (1), A represents a single bond or an alkylene group, and examples of alkylene group include methylene group, 10 ethylene group, propylene group and trimethylene group. In the formula (1), each of R' and R 2 independently represents alkyl group, and examples of alkyl group include methyl group, ethyl group, isopropyl group, butyl group. The sum of the number of carbon atoms which consist of the group of R1, R2 and A in the 15 formula (1) is 2 to 8, preferably 2 to 5. Examples of the present solvent include diethyl oxalate, dipropyloxalate, dimethylmalonate, dipropylmalonate, dimethyl succinate, diethyl succinate. The present solvent can be used for the emulsifiable concentrate of the present invention by 20 itself or mixture of above mentioned compound. For the emulsifiable concentrate of the present invention, diethyl oxalate is preferably used. The amount of the present solvent to be used for the emulsifiable concentrate of the present invention is usually 5 25 to80 %byweight, preferably20 to80%byweight andmore preferably 20 to 70 % by weight based on the total weight of the emulsifiable concentrate of the present invention. And the amount of the present solvent to be used for the emulsifiable concentrate of the present invention) is usually 5 to 80 by weight, preferably 9 8 to 80 by weight and more preferably 8 to 30 by weight based on the weight of diflufenican. The emulsifiable concentrate of the present invention may 5 contain another organic solvent. Examples of another organic solvent includes aromatic hydrocarbons such as alkylbenzene(for example, xylene, tetramethylbenzene and the like) , alkylnaphthalene( for example, methylnaphthalene), diphenylethane, dixylylethane, 10 phenylxylylethane and the like; fatty acid monoesters such as methyl laurate, isopropyl myristate, isopropyl palmital:e, methyl caprate, methyl oleate, isobutyl oleate, butyl propionate, isoamyl propionate, ethyl butyrate, butyl butyrate, isoamyl butyrate, isoamyl valerate, amyl lactate, methyl linoleate, 15 methyl linolenate, palm fatty acid methyl and the like; aliphatic hydrocarbons such as cyclohexane; N,N-dimethyl acetamide; N-methyl-2-pyrrolidone and 1,3-dimethyl-2-imidazolidinone. Commercially available products such as Hisol. SAS-296 (commercial name of Nippon Oil Corp., a mixture of 20 1-phenyl-1-xylylethane and 1-phenyl-1-ethylphenylet.hane), Cactus Solvent HP-MN (commercial name of Nikko Petrochemical Company, containing 80% of methylnaphthalene), Cactus Solvent HP-DMN (commercial name of Nikko Petrochemical Company, containing 80% of dimethylnaphthalene), Cactus Solvent P-100 25 (commercial name of Nikko Petrochemical Company, alkylbenzene having 9 to 10 carbon atoms), Cactus Solvent P-150 (commercial name of Nikko Petrochemical Company, alkylbenzene), Cactus Solvent P-180 (commercial name of Nikko Petrochemical Company, a mixture of methylnaphthalene and dimethylnaphthalene) , Cactus 10 Solvent P-200 (commercial name of Nikko Petrochemical Company, a mixture of methylnaphthalene and dimethylnaphthalene) , Cactus Solvent P-220 (commercial name of Nikko Petrochemical Company, a mixture of methylnaphthalene and dimethylnaphthalene), Cactus 5 Solvent PAD-1 (commercial name of Nikko Petrochemical Company, dimethylmonoisopropylnaphthalene), Solvesso 100 (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly C9 to C10 dialkyl and trialkyl benzene) , Solvesso 150 (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly 10 C10 to Cl alkylbenzene), Solvesso 150 ND (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly C10 to Cll alkylbenzene) , Solvesso 200 (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly C10 to C14 alkylnaphthalene), ULTRA LOW NAPHTHALENE AROMATIC 150 15 (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly C10 to C11 alkylbenzene), ULTRA LOW NAPHTHALENE AROMATIC 200 (commercial name of Exxon Mobil Chemical Company, aromatic hydrocarbon, mainly Cl to C14 alkylnaphthalene) , Solvesso 200 ND (commercial name of Exxon Mobil 20 Chemical Company, aromatic hydrocarbon, mainly C11 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. 25 In the emulsifiable concentrate of the present invention, it is preferable that an aromatic hydrocarbon and/or N-methyl-2-pyrrolidone and/or 1,3-dimethyl-2-imidaz.olidinone are contained.
11 In case of the emulsifiable concentrate of the: present invention includes an aromatic hydrocarbon, the amount of the aromatic hydrocarbon is usually 1 to 40 % by weight based on the total weight of the emulsifiable concentrate of the present 5 invention. In case of the emulsifiable concentrate of the present invention includes N-methyl-2-pyrrolidone, the amount of N-methyl-2-pyrrolidone is usually 3 to 30 % by weight based on the total weight of the emulsifiable concentrate of the present 10 invention. In case of the emulsifiable concentrate of the present invention includes 1,3-dimethyl-2-imidazolidinone, the amount of 1, 3-dimethyl-2-imidazolidinone is usually 5 to 80 % by weight, preferably 5 to 60 % by weight, more preferably 5 to 50 % by weight, 15 far more preferably 10 to 50 % by weight based on the total weight of the emulsifiable concentrate of the present invention. The emulsifiable concentrate of the present invention contains a surfactant. The surfactant used for the emulsifiable 20 concentrate of the present invention is preferably a mixture 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, 25 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, polyoxyethylenealkylaryl phosphate ester, and 12 polyoxyethylenealkyl 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. 5 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, Rhodacal60/BE(each produced by Rhodia Nicca), 10 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 Nicca) can be used as polyoxyethylene distyryl phenyl ether sulfate. Commercially 15 available surfactant such as Soprophor FLK(produced by Rhodia Nicca) can be used as polyoxyethylene tristiryl phenyl ether phosphoric acid. Commercially available surfactant such as Rhodafac PS/17(produced by Rhodia Nicca) can be used as polyoxyethylenealkylaryl phosphate ester. Commercially 20 available surfactant such as RhodafacMB(producedbyRhodiaNicca) can be used as polyoxyethylenealkyl phosphate ester. Examples of nonionic surfactant include polyoxyethylene-polyoxypropylene block polymer; fatty acid ester of polyoxyethylene-polyoxypropylerLe block 25 polymer; polyoxyethylene-polyoxypropylene alkyl ether; polyoxyethylene-polyoxypropylene polyaryl ether such as polyoxyethylene-polyoxypropylene tristyryl phenyl ether, polyoxyethylene-polyoxypropylene distyryl phenyl ether and the 13 like; polyoxyethylene-polyoxypropylene alkyl aryl ether; polyoxyethylene alkyl aryl ether; polyoxyethylene polyaryl ether such as polyoxyethylene tristyryl 5 phenyl ether, polyoxyethylen 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; 10 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: 15 polyoxyethylene-polyoxypropylene tristyryl phenyl phosphate diester; polyalkyleneoxide block copolymer; butyl polyalkyleneoxide block copolymer; fatty acid alcohol polyglycol ether; 20 fatty acid ester of glycerin; and sorbitan fatty acid ester. Preferable examples of the nonionic surfactants to be used for the emulsifiable concentrate of the present invention are the nonionic surfactant which has polyalkylene oxide structure 25 in the molecule and sorbitan fatty acid ester. Examples of the nonionic surf actant which has polyalkylene oxide structure in the molecule are as polyoxyethylene-polyoxypropylene tristyryl phenyl ether, polyoxyethylene tristyryl phenyl ether, 14 polyoxyethylene castor oil, polyoxyethylene hardened castor oil, polyoxyethylene alkyl aryl ether, polyoxyethylene tristyryl phenyl phosphate diester or 5 polyoxyethylene-polyoxypropylene tristyryl phenyl phosphate diester. In the nonionic surfactant which has polyalkylene oxide structure in the molecule, especially polyoxyethylene-polyoxypropylene tristyryl phenyl ether, 10 polyoxypropylene tristyryl phenyl ether, polyalkyleneoxide block copolymer, butyl polyalkyleneoxide block copolymer or polyoxyethylene castor oil is pref erably used for the emulsifiable concentrate of the present invention. The HLB value of the nonionic surfactant which has 15 polyalkylene oxide in the molecule is usually 10 to 17, preferably 10 to 14, more preferably 11 to 12. Commercially available surfactant such as Teric PE 64(produced by Huntsman) can be used as polyoxyethylene-polyoxypropylene block polymer. Commercially 20 available surfactant such as Antarox BO/327, 340 Antarox BO series(each produced by Rhodia Nicca) can be used as polyoxyethylene-polyoxypropylene alkyl ether. Commercially available surf actant such as Solpol T26 (produced by Toho Chemical Industry) can be used as polyoxyethylene alkyl aryl ether. 25 Commercially available surfactant such as Soprophor 796/P(HLB 13.7, produced by Rhodia Nicca) can be used as polyoxyethylene-polyoxypropylene tristyryl phenyl ether. Commercially available surf actant such as Soprophor BSU ( HLB 12. 6, produced by Rhodia Nicca) can be used as polyoxyethylene tristyryl 15 phenyl ether. Commercially available surfactant such as Alkamuls OR40, Alkamuls BR(each produced by Rhodia Nicca) can be used as polyoxyethylene castor oil. Commercially available surfactant such as HCO-20(produced by Nikko Chemicals) can be 5 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 Nicca) cain be used as polyoxyethylene-polyoxypropylene castor oil. Commercially available surfactant such as Newcol 150(produced by Nippon 10 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 15 &Fat) can be used as fatty acid ester of glycerin. Commercially available surfactant such as Toximul 8320(produced by Stepan) can be used as butyl polyalkyleneoxide block copolymer. Commercially available surfactant such as Toximul 8323(produced by Stepan), Step-Flow 26(produced by Stepan) and Ethylan NS 500 20 LQ(produced by Akzo Nobel) can be used as polyalkyleneoxide block copolymer. Sorbitan fatty acid esters are an ester compound which is condensed by sorbitan and fatty acid. Sorbitan is an intramolecular dehydration product of sorbitol. There are 25 several kinds of sorbitan fatty acid ester such as sorbitan mono fatty acid ester, sorbitan tri fatty acid ester and the like depending on the number of condensed fatty acid. There are several kinds of sorbitans such as 1,4-sorbitan, 1,5-sorbitan and the like, depending on the dehydrating position of intramolecular 16 dehydration of sorbitol. As f atty acids condensed with sorbitan, fatty acids which the number of carbon atoms is 10 to 22 are usually used. Concretely, saturated fatty acids such as capric acid, lauric acid, myristic acid, pentadecanoic acid, palmitic acid, 5 stearic acid and the like, and unsaturated fatty acids such as oleic acid, linoleic acid, linolenic acid and the like are exemplified. Sorbitan f atty acid esters concretely include, f or example, sorbitan mono laurate, sorbitan mono palmitate, sortitan mono 10 stearate, sorbitan mono oleate and the like. 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 15 Lonza Japan), Glycomul TS(sorbitan tri stearate, HLB 2, produced by Lonza Japan), NIKKOL SL-10(sorbitan mono laurate, HLB 8.6, produced by Nikko Chemicals), NIKKOL SP-10V(sorbitan mono palmitate, HLB 6.7, produced by Nikko Chemicals), NIKKOL SS-1OV(sorbitan mono stearate, HLB 4.7, produced by Nikko 20 Chemicals), NIKKOL SS-30V(sorbitan tri stearate, HLB 2.1, produced by Nikko Chemicals), NIKKOL SI-10RV(sorbitan mono isostearate, HLB 5.0, produced by Nikko Chemicals), NIKKOL SO-15R(sorbitan sesquioleate and HLB 4.5, produced by Nikko Chemicals) can be used for the emulsifiable concentrate of the 25 present invention. In case of the emulsifiable concentrate of the present invention includes sorbitan fatty acid ester, the amount of the sorbitan fatty acid ester is usually 0.5 to 10 % by weight, preferably 1 to 8 % by weight based on the total of the emulsifiable 17 concentrate of the present invention. And in this case, the amount of the sorbitan fatty acid ester is preferably 0.2 to 2.5 times by weight based on the weight of diflufenican. In the view point of stability while keeping in low temperature, it is preferable 5 that the emulsifiable concentrate of the present invention includes sorbitan fatty acid ester as a nonionic surfactant. The stability while keeping in low temperature means having a character of producing little oil like separation or solid while keeping in law temperature such as below 5 *C. 10 The nonionic surfactant used for the emulsifiable concentrate of the present invention may be consisted of one kind of nonionic surfactant or may be consisted of at least two kinds of nonionic surf actants. In case of the nonionic surf actant used for the emulsifiable concentrate of the present invention is 15 consisted of at least two kinds of nonionic surfactants, the combination of the nonionic surfactants includes, for example, the combination of the nonionic surf actant which has polyalkylene oxide structure in the molecule and sorbitan fatty acid ester, more concretely the combination of polyoxyethylene tristyryl 20 phenyl ether and sorbitan fatty acid ester. In the emulsifiable concentrate of the present invention, the amount of surfactant is usually 4 to 20 % by weight, preferably 4 to 15 % by weight based on the total weight of the emulsifiable concentrate of the present invention. In case of the surfactant 25 used for the emulsifiable concentrate of the presel: invention is a mixture of an anionic surf actant and a nonionic surfactant, the weight ratio of the anionic surfactant and the nonionic surfactant is usually 1:0.1 to 1:10, preferably 1:0.4 to 1:2.5.
18 The emulsifiable concentrate of the present invention may further include an additive. Examples of the additive include antioxidant such as 3-/2-t-butyl-4-hydroxyanisole, butyl hydroxy toluene and the 5 like; coloring agent and the like. The mode of the emulsifiable concentrate of the present invention includes as following: An emulsifiable concentrate, which comprises 10 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of the compound shown by the formula (1). 15 An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15 % byweight of a nonionic surf actant which has polyalkylene 20 oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of the compound shown by the formula (1). 25 An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N-methyl-2-pyrrolidone; 19 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate. An emulsifiable concentrate, which comprises 5 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5tol5%byweightof anonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 10 3 to 30 % by weight of N-methyl-2-pyrrolidone; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate. An emulsifiable concentrate, which comprises 15 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N,N-dimethylacetamide; 5 to 20 % by weight of an aromatic hydrocarbon; and. 20 5 to 70 % by weight of diethyl oxalate. An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 25 0.5 to 15 %byweightofanonionicsurfactantwhichhaspolyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N,N-dimethylacetamide; 5 to 20 % by weight of an aromatic hydrocarbon; and 20 5 to 70 % by weight of diethyl oxalate. An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 5 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate. 10 An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0 .5to15 %byweightofanonionicsurfactantwhichhaspolyalkylene 15 oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinofne; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate. 20 An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 25 3 to 30 % by weight of N-methyl-2-pyrrolidone; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 : 0.2 to 1 : 1.5; and 21 and the ratio by weight of N-methyl-2-pyrrolidone and diethyl oxalate is 1 : 0.1 to 1 : 1. An emulsifiable concentrate, which comprises 5 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N,N-dimethylacetamide; 5 to 20 % by weight of an aromatic hydrocarbon; and 10 5 to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 : 0.2 to 1 : 1.5; and and the ratio by weight of N,N-dimethylacetamide and diethyl oxalate is 1 : 0.1 to 1 : 1. 15 An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5tol5%byweightofanonionicsurfactantwhichhaspolyalkylene 20 oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N,N-dimethylacetamide; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate; and 25 the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 : 0.2 to 1 : 1.5; and and the ratio by weight of N,N-dimethylacetamide and diethyl oxalate is 1 : 0.1 to 1 : 1.
22 An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 5 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinoe; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 : 0.2 to 1 : 1.5; and 10 and the ratio by weight of 1,3-dimethyl-2-imidazolidinone and sum of an aromatic hydrocarbon and diethyl oxalate is 1 : 0.1 to 1 : 1. An emulsifiable concentrate, which comprises 15 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5tol5%byweightof a nonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 20 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 : 0.2 to 1 : 1.5; and 25 and the ratio by weight of the 1,3-dimethyl-2-imidazolidinone and sum of an aromatic hydrocarbon and diethyl oxalate is 1 0.1 to 1 : 1. An emulsifiable concentrate, which comprises 23 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 5 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of the compound shown by the formula (1). An emulsifiable concentrate, which comprises 10 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15%byweight of anonionic surf actant which has polyalkylene 15 oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of the compound shown by the formula (1). 20 An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 25 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N-methyl-2-pyrrolidone; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate.
24 An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 5 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 15 % byweight of a nonionic surf actant whichhas polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N-methyl-2-pyrrolidone; 10 5 to 20 % by weight of an aromatic hydrocarbon; and. 5 to 70 % by weight of diethyl oxalate. An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 15 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N,N-dimethylacetamide; 20 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate. An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 25 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5to15%byweightof anonionic surfactantwhichhas pcolyalkylene oxide structure in the molecule; 25 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N,N-dimethylacetamide; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate. 5 An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 10 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate. 15 An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 20 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 tol 5%byweight ofanonionicsurfactantwhichhaspolyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; 25 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate. An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 26 I to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 5 3 to 30 % by weight of N-methyl-2-pyrrolidone; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 : 0.2 to 1 : 1.5; and 10 and the ratio by weight of N-methyl-2-pyrrolidone and diethyl oxalate is 1 : 0.1 to 1 : 1. An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 15 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of N,N-dimethylacetamide; 20 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 : 0.2 to 1 : 1.5; and and the ratio by weight of N,N-dimethylacetamide and diethyl 25 oxalate is 1 : 0.1 to 1 : 1. An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 27 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinonle; 5 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 : 0.2 to 1 : 1.5; and and the ratio by weight of 1,3-dimethyl-2-imidazolidinone and 10 sum of an aromatic hydrocarbon and diethyl oxalate is 1 : 0.1 to 1 : 1. An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 15 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; and 10 to 90 % by weight of diethyl oxalate. An emulsifiable concentrate, which comprises 20 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5tol5%byweightof a nonionic surfactant whichhas poLyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; and 25 10 to 90 % by weight of diethyl oxalate. An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 28 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinonle; and 10 to 90 % by weight of diethyl oxalate. 5 An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0. 5 to 15 % byweight of a nonionic surfactant whichhas polyalkylene oxide structure in the molecule; 10 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinoCne; and 10 to 90 % by weight of diethyl oxalate. An emulsifiable concentrate, which comprises 15 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; 5 to 20 % by weight of an aromatic hydrocarbon; and 20 5 to 70 % by weight of diethyl oxalate. An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 25 0.5 to 15 %byweightofanonionicsurfactantwhichhaspolyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazoldin.one; 5 to 20 % by weight of an aromatic hydrocarbon; ard 29 5 to 70 % by weight of diethyl oxalate. An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 5 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; and 10 to 90 % by weight of diethyl oxalate and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 : 0.2 to 1 : 1.5. 10 An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0. 5 to 15 % byweight of a nonionic surfactant which has polyalkylene 15 oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; and 10 to 90 % by weight of diethyl oxalate and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 : 0.2 to 1 : 1.5. 20 An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 25 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; and 10 to 90 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 : 0.2 to 1 : 1.5.
30 An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0 .5 to 15% byweight of a nonionic surf actant which has polyalkylene 5 oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinonle; and 10 to 90 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid 10 ester is 1 : 0.2 to 1 : 1.5. An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 15 0.5 to 10 % by weight of an.alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid 20 ester is 1 :0. 2 to 1 : 1. 5, and the ratio by weight of diflufenican and the sorbitan fatty acid ester is 1 : 0.2 to 1 : 1.5. An emulsifiable concentrate, which comprises 0.5 to 5 % by weight of diflufenican; 25 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0. 5 to 15 % byweight of anonionic surfactantwhichhas polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 3 to 30 % by weight of 1,3-dimethyl-2-imidazolidinone; 31 5 to 20 % by weight of an aromatic hydrocarbon; and 5 to 70 % by weight of diethyl oxalate; and the ratio by weight of diflufenican and the sorbitan fatty acid esteris 1: 0.2 to 1: 1.5, and the ratio by weight ofdiflufenican 5 and the sorbitan fatty acid ester is 1 : 0.2 to 1 : 1.5. An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 10 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of an anionic surfactant; 0.5 to 10 % by weight of a nonionic surfactant; 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrrolidone; 15 5 to 80 % by weight of 1,3-dimethyl-2-imidazolidinone; and 5 to 80 % by weight of the compound shown by the formula (1). An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; 20 15 to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 1 to 5 % by weight of a nonionic surfactant; 1 to 10 % by weight of an aromatic hydrocarbon; 25 2 to 8 % by weight of N-methyl-2-pyrrolidone; 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and 50 to 80 % by weight of the compound shown by the formula (1). An emulsifiable concentrate essentially consisting of 32 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octaloate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of an anionic surfactant; 5 0.5 to 10 % by weight of a nonionic surfactant; 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrrolidone; 5 to 80 % by weight of 1,3-dimethyl-2-imidazolidinone; and 5 to 80 % by weight of the compound shown by the formula (1). 10 An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 15 to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 15 1 to 5 % by weight of an anionic surfactant; 1 to 5 % by weight of a nonionic surfactant; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and 20 50 to 80 % by weight of the compound shown by the formula (1). An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 15 to 20 % by weight of bromoxynil=octanoate; 25 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 1 to 5 % by weight of a nonionic surfactant; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; 33 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidinofne; and rest of the compound shown by the formula (1). An emulsifiable concentrate comprising 5 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 0.5to10%byweightofanonionicsurfactantwhichhaspolyalkylene 10 oxide structure in the molecule; 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrrolidone; 5 to 80 % by weight of 1,3-dimethyl-2-imidazolidinone; and 5 to 80 % by weight of the compound shown by the formula (1) . 15 An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; 15 to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 20 1 to 5 % by weight of an alkylbenzenesulfonic acid salt; 1 to 5 % by weight of a nonionic surfactant which has polyalkylene oxide structure in the molecule; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; 25 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and 50 to 80 % by weight of the compound shown by the formula (1). An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 34 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of an alkylbenzenesulfonic acid salt; 0.5to10%byweightof anonionic surf actant which has polyalkylene 5 oxide structure in the molecule; 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrrolidone; 5 to 80 % by weight of 1,3-dimethyl-2-imidazolidinone; and 5 to 80 % by weight of the compound shown by the formula (1). 10 An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 15 to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 15 1 to 5 % by weight of an alkylbenzenesulfonic acid salt; 1 to 5 % by weight of a nonionic surf actant which has polyalkylene oxide structure in the molecule; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; 20 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and 50 to 80 % by weight of the compound shown by the formula (1). An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 25 15 to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an alkylbenzenesulfonic acid salt; 1 to 5 % by weight of a nonionic surfactant which has polyalkylene oxide structure in the molecule; 35 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and rest of the compound shown by the formula (1). 5 An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 10 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyalkyleneoxide block copolymer; 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrrolidone; 5 to 80 % by weight of 1,3-dimethyl-2-imidazolidinone; and 15 5 to 80 % by weight of diethyl oxalate. An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; 15 to 20 % by weight of bromoxynil=octanoate; 20 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 1 to 5 % by weight of polyalkyleneoxide block copolymer; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; 25 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and 50 to 80 % by weight of diethyl oxalate. An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 36 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyalkyleneoxide block copolymer; 5 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrrolidone; 5 to 80 % by weight of 1,3-dimethyl-2-imidazolidinonle; and 5 to 80 % by weight of diethyl oxalate. 10 An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 15 to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 15 1 to 5 % by weight of polyalkyleneoxide block copolymer; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidin.one; and 50 to 80 % by weight of diethyl oxalate. 20 An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 15 to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 25 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 1 to 5 % by weight of polyalkyleneoxide block copolymer; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and 37 rest of diethyl oxalate. An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 5 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of butylpolyalkyleneoxide block copolymer; 1 to 40 % by weight of an aromatic hydrocarbon; 10 3 to 30 % by weight of N-methyl-2-pyrrolidone; 5 to 80 % by weight of 1,3-dimethyl-2-imidazolidinonle; and 5 to 80 % by weight of diethyl oxalate. An emulsifiable concentrate comprising 15 2 to 5 % by weight of diflufenican; 15 to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 1 to 5 % by weight of butylpolyalkyleneoxide block copolymer; 20 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and 50 to 80 % by weight of diethyl oxalate. 25 An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 38 0.5 to 10 % by weight of butylpolyalkyleneoxide block copolymer; 1 to 40 % by weight of an aromatic hydrocarbon; 3 to 30 % by weight of N-methyl-2-pyrrolidone; 5 to 80 % by weight of 1,3-dimethyl-2-imidazolidinonle; and 5 5 to 80 % by weight of diethyl oxalate. An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 15 to 20 % by weight of bromoxynil=octanoate; 10 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 1 to 5 % by weight of butylpolyalkyleneoxide block copolymer; 1 to 10 % by weight of an aromatic hydrocarbon; 2 to 8 % by weight of N-methyl-2-pyrrolidone; 15 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidinlone; and 50 to 80 % by weight of diethyl oxalate. An emulsifiable concentrate essentially consisting of 3 to 5 % by weight of diflufenican; 20 15 to 20 % by weight of bromoxynil=octanoate; 12 to 18 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 1 to 5 % by weight of butylpolyalkyleneoxide block copolymer; 1 to 10 % by weight of an aromatic hydrocarbon; 25 2 to 8 % by weight of N-methyl-2-pyrrolidone; 10 to 20 % by weight of 1,3-dimethyl-2-imidazolidinone; and rest of diethyl oxalate. An emulsifiable concentrate comprising 39 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of an anionic surfactant; 5 0.5to10%byweightofanonionicsurfactantwhichhaspolyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 1 to 40 % by weight of an aromatic hydrocarbon; and 5 to 80 % by weight of the compound shown by the formula (1). 10 An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 15 1 to 5 % by weight of an anionic surfactant; 3 to 8 % by weight of a nonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 10 % by weight of an aromatic hydrocarbon; and 20 50 to 80 % by weight of the compound shown by the formula (1). An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 25 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of an anionic surfactant; 0.5to10%byweightof anonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 40 1 to 40 % by weight of an aromatic hydrocarbon; and 5 to 80 % by weight of the compound shown by the formula (1). An emulsifiable concentrate essentially consisting of 5 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 3 to 8 % by weight of a nonionic surf actant which has polyalkylene 10 oxide structure in the molecule; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 10 % by weight of an aromatic hydrocarbon; and 50 to 80 % by weight of the compound shown by the formula (1). 15 An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 20 3 to 8 % by weight of a nonionic surfactant which has polyalkylene oxide structure in the molecule; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 10 % by weight of an aromatic hydrocarbon; and rest of the compound shown by the formula (1). 25 An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 41 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 1 to 40 % by weight of an aromatic hydrocarbon; and 5 5 to 80 % by weight of the compound shown by the formula (1). An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; 10 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfcnate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 10 % by weight of an aromatic hydrocarbon; and 15 50 to 80 % by weight of the compound shown by the formula (1). An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 20 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by'weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 1 to 40 % by weight of an aromatic hydrocarbon; and 25 5 to 80 % by weight of the compound shown by the formula (1). An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; 42 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 5 1 to 10 % by weight of an aromatic hydrocarbon; and 50 to 80 % by weight of the compound shown by the formula (1). An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 10 10 to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 15 1 to 10 % by weight of an aromatic hydrocarbon; and rest of the compound shown by the formula (1). An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 20 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 10 % by weight of sorbitan mono laurate; 25 1 to 40 % by weight of an aromatic hydrocarbon; and 5 to 80 % by weight of diethyl oxalate. An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; 43 10 to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 5 0.5 to 3 % by weight of sorbitan mono laurate; 1 to 10 % by weight of an aromatic hydrocarbon; and 50 to 80 % by weight of diethyl oxalate. An emulsifiable concentrate essentially consisting of 10 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyoxypropylene tristyryl phenyl ether; 15 0.5 to 10 % by weight of sorbitan mono laurate; 1 to 40 % by weight of an aromatic hydrocarbon; and 5 to 80 % by weight of diethyl oxalate. An emulsifiable concentrate essentially consisting of 20 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 25 0.5 to 3 % by weight of sorbitan mono laurate; 1 to 10 % by weight of an aromatic hydrocarbon; and 50 to 80 % by weight of diethyl oxalate. An emulsifiable concentrate essentially consisting of 44 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 5 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of sorbitan mono laurate; 1 to 10 % by weight of an aromatic hydrocarbon; and rest of diethyl oxalate. 10 An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of an anionic surfactant; 15 0.5 to 10 %byweightofanonionicsurfactantwhichhaspolyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 1 to 40 % by weight of an aromatic hydrocarbon; 5 to 80 % by weight of 1,3-dimethyl-2-imidazoridione; and 20 5 to 80 % by weight of the compound shown by the formula (1). An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; 25 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 3 to 8 % by weight of a nonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 45 1 to 15 % by weight of an aromatic hydrocarbon; 10 to 50 % by weight of 1,3-dimethyl-2-imidazoridione; and 10 to 50 % by weight of the compound shown by the formula (1). 5 An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of an anionic surfactant; 10 0.5to10%byweightof anonionic surfactantwhichhas polyalkylene oxide structure in the molecule; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 1 to 40 % by weight of an aromatic hydrocarbon; 5 to 80 % by weight of 1,3-dimethyl-2-imidazoridione; and 15 5 to 80 % by weight of the compound shown by the formula (1). An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; 20 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 3 to 8 % by weight of a nonionic surf actant which has polyalkylene oxide structure in the molecule; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 25 1 to 15 % by weight of an aromatic hydrocarbon; 10 to 50 % by weight of 1,3-dimethyl-2-imidazoridione; and 10 to 50 % by weight of the compound shown by the formula (1). An emulsifiable concentrate essentially consisting of 46 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of an anionic surfactant; 5 3 to 8 % by weight of a nonionic surfactant which has polyalkylene oxide structure in the molecule; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 15 % by weight of an aromatic hydrocarbon; 10 to 50 % by weight of 1,3-dimethyl-2-imidazoridione; and 10 rest of the compound shown by the formula (1). An emulsifiable concentrate comprising 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 15 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 1 to 40 % by weight of an aromatic hydrocarbon; 20 5 to 80 % by weight of 1,3-dimethyl-2-imidazoridione; and 5 to 80 % by weight of the compound shown by the formula (1). An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; 25 10 to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 47 1 to 15 % by weight of an aromatic hydrocarbon; 10 to 50 % by weight of 1,3-dimethyl-2-imidazoridione; and 10 to 50 % by weight of the compound shown by the formula (1). 5 An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 10 0. 5 to 10 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 1 to 40 % by weight of an aromatic hydrocarbon; 5 to 80 % by weight of -1,3-dimethyl-2-imidazoridiote; and 5 to 80 % by weight of the compound shown by the formula (1). 15 An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 20 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 1 to 15 % by weight of an aromatic hydrocarbon; 10 to 50 % by weight of 1,3-dimethyl-2-imidazoridifone; and 25 10 to 50 % by weight of the compound shown by the formula (1). An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; 48 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of a sorbitan fatty acid ester; 5 1 to 15 % by weight of an aromatic hydrocarbon; 10 to 50 % by weight of 1,3-dimethyl-2-imidazoridione; and rest of the compound shown by the formula (1) An emulsifiable concentrate comprising 10 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyoxypropylene tristyryl phenyl ether; 15 0.5 to 10 % by weight of sorbitan mono laurate; 1 to 40 % by weight of an aromatic hydrocarbon; 5 to 80 % by weight of 1,3-dimethyl-2-imidazoridione; and 5 to 80 % by weight of diethyl oxalate. 20 An emulsifiable concentrate comprising 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 25 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 3 % by weight of sorbitan mono laurate; 1 to 15 % by weight of an aromatic hydrocarbon; 10 to 50 % by weight of 1,3-dimethyl-2-imidazoridione; and 10 to 50 % by weight of diethyl oxalate.
49 An emulsifiable concentrate essentially consisting of 0.5 to 5 % by weight of diflufenican; 1 to 30 % by weight of bromoxynil=octanoate; 5 1 to 30 % by weight of ioxynil=octanoate; 0.5 to 10 % by weight of calcium dodecyl benzene sulfonate; 0.5 to 10 % by weight of polyoxypropylene tristyryl phenyl ether; 0.5 to 10 % by weight of sorbitan mono laurate; 1 to 40 % by weight of an aromatic hydrocarbon; 10 5 to 80 % by weight of 1,3-dimethyl-2-imidazoridione; and 5 to 80 % by weight of diethyl oxalate. An emulsifiable concentrate essentially consisting of 2 to 5 % by weight of diflufenican; 15 10 to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl pheryl ether; 0.5 to 3 % by weight of sorbitan mono laurate; 20 1 to 15 % by weight of an aromatic hydrocarbon; 10 to 50 % by weight of 1,3-dimethyl-2-imidazoridione; and 10 to 50 % by weight of diethyl oxalate. An emulsifiable concentrate essentially consisting of 25 2 to 5 % by weight of diflufenican; 10 to 20 % by weight of bromoxynil=octanoate; 5 to 15 % by weight of ioxynil=octanoate; 1 to 5 % by weight of calcium dodecyl benzene sulfonate; 3 to 8 % by weight of polyoxypropylene tristyryl phenyl ether; 50 0.5 to 3 % by weight of sorbitan mono laurate; 1 to 15 % by weight of an aromatic hydrocarbon; 10 to 50 % by weight of 1,3-dimethyl-2-imidazoridionle; and rest of diethyl oxalate. 5 The emulsifiable concentrate of the present invention can be produced by mixing the component of the emulsifiable concentrate of the present invention, then stirring until the mixture becomes uniform. The temperature while stirring is 10 usually in the range between room temperature and 85 *C. The mixing order of the component of the emulsifiable concentrate of the present invention may be properly decided. The emulsifiable concentrate of the present invention is usually applied after diluted with water to a weed or soil surface 15 where weed is predicted to grow. An aqueous composition which is obtained by diluted the emulsifiable concentrate of the present invention with water is a diluted composition of the emulsifiable concentrate of the present invention with water of the amount of usually 10 to 5000 times, preferably 20 to 2500 times based 20 on the amount of the emulsifiable concentrate of the present invention. Generally, the water used to dilution may be soft water or hard water. Auxiliaries such as spreader may be added to the water used to dilution, if necessary. Though the application amount of the aqueous composition 25 which is obtained by diluted the emulsifiable concentrate of the present invention with water may vary depending on the ratio of diflufenican, bromoxynil=octanoate and ioxynil=octanoate; weather conditions; the treatment timing; the treatment place; the kind of a weed which is controlled, it is 51 usually 40 to 2000g, preferably 80 to 1000g per hectare as total weight of diflufenican, bromoxynil=octanoate and ioxynil=octanoate. 5 EXAMPLES Hereinafter, the present invention will be further explained in detail by way of Preparation Examples and Test Examples, but the present invention is not limited to these examples. 10 Preparation Example 1-1 Diflufenican(purity 91 %, 3.6 g as active ingredient), bromoxynil=octanoate (purity 9 5. 4 %, 17. 33 g as active ingredient) and ioxynil=octanoate(purity 96 %, 9.65 g as active ingredient) were added to diethyl oxalate(40.54 g) under heating and were 15 dissolved. Then calcium dodecyl benzene sulfonate (Rhodacal60/BE, surfactant produced by Rhodia Nicca; 3.83 g) and polyoxypropylene castor oil(Alkamuls OR40, surfactant produced by Rhodia Nicca; 3.83 g) were added to it. Furthermore, aromatic hydrocarbon (mainly C10 to C11 alkylbenzene, Solvesso 150 ND, CAS 20 No. 64742-94-5, Exxon Mobil Chemical Company) was added until total amount being 100 ml, and stirred until uniform solution to give the emulsifiable concentrate of the present invention (ref erred as the emulsif iable concentrate of the present invention 1-1, hereinafter). 25 Test Example 1-1 The emulsifiable concentrate of the present invention 1-1 was diluted by CIPAC standard water D (342ppm) for 100 times in a 100 ml - graduated cylinder with stopper. It was left at 30 0 C for 2 hours, andwas observed the stability of the emulsion. Af ter 52 that, the aqueous composition which was obtained by diluted the emulsifiable concentrate of the present invention 1-1 with water kept stable emulsion. Preparation Example 1-2 5 Diflufenican(4.0 g as active ingredient) , calcium dodecyl benzene sulfonate (Rhodacal 70, surfactant produced by Rhodia Nicca; 4.75 g) and polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P, surfactant produced by Rhodia Nicca; 2. 25 g) were measured in a 100 ml graduated flask at 20 * C. 10 Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention (ref erred as the emulsifiable concentrate of the present invention 1-2, hereinafter). Preparation Example 1-3 15 Difluf enican (4. 0 g as active ingredient), calcium dodecyl benzene sulfonate (Rhodacal 70, surfactant produced by Rhodia Nicca; 5.50 g) and polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P, surfactant produced by Rhodia Nicca; 1.50 g) were measured in a 100 ml graduated flask at 20 0 C. 20 Then diethyl oxalate was added until the total amount: being 100 ml. Itwas stirreduntil uniform solution to give the emulsifiable concentrate of the present invention (ref erred as the emulsifiable concentrate of the present invention 1-3 hereinafter). Test Example 1-2 25 Each of the emulsifiable concentrate of the present invention 1 and 2 was diluted by CIPAC standard water D (342ppm) for 100 times in a 100 ml - graduated cylinder with stopper. They were left at 30 * C for 2 hours, and were observed the stability of the emulsion. After that, the aqueous composition which were 53 obtained by diluting the emulsifiable concentrate of the present invention 1-2 and 1-3 with water kept stable emulsion. Preparation Example 1-4 Diflufenican(3.71 g as active ingredient), 5 bromoxynil=octanoate(18.22 g as active ingredient), ioxynil=octanoate(9.63g as active ingredient), calcium dodecyl benzene sulfonate (Rhodacal 70, surfactant produced by Rhodia Nicca; 3.17 g) and polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P, surfactant produced by Rhodia 10 Nicca; 4.52 g) were measured in a 100 ml graduated flask at 20 0 C. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention (ref erred as the emulsifiable concentrate of the present invention 1-4 hereinafter). 15 Preparation Example 1-5 Diflufenican(3.71 g as active ingredient), bromoxynil=octanoate(18.22 g as active ingredient), ioxynil=octanoate(9. 63g as active ingredient), calcium dodecyl benzene sulfonate (Rhodacal 70, surfactant produced by Rhodia 20 Nicca; 3.17 g) and polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P, surfactant produced by Rhodia Nicca; 4.52 g) were measured in a 100 ml graduated flask at 20 0 C. Then diethyl oxalate(40.39 g) and Solvesso 200 ND(mai.nly Cll to C14 alkylnaphthalene, aromatic hydrocarbon, Exxon Mobil Chemical 25 Company; 20.16 g) were added. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention (ref erred as the emulsifiable concentrate of the present invention 1-5 hereinafter). Test Example 1-3 54 Each of the emulsifiable concentrate of the present invention 1-4 and 1-5 was diluted by CIPAC standard water D (342ppm) for 100 times in a 100 ml - graduated cylinder with stopper. They were left at 30 0 C for 2 hours, and were observed the stability 5 of the emulsion. After that, the aqueous composition which were obtained by diluting the emulsifiable concentrate of the present invention 1-4 and 1-5 with water kept stable emulsion. Preparation Example 2-1 10 Diflufenican(purity 93.2 %, 4.0 g as active ingredient) , calcium dodecyl benzene sulfonate (Rhodacal 70, surfactant produced by Rhodia Nicca; 4.00 g), polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P, produced by Rhodia Nicca; 3.00 g) and 15 1,3-dimethyl-2-imidazolidinone(45.00 g) were measured to a 100 ml - graduated flask, and filled to 100 ml with diethyl oxalate. Then it was stirred until uniform solution to give the emulsifiable concentrate of the present invention (ref erred as the emulsif able concentrate of the present invention 2-1, hereinafCer). 20 Preparation Example 2-2 Diflufenican( 4. 0 g as active ingredient) , calcium dodecyl benzene sulfonate (Rhodacal 70, surfactant produced by Rhodia Nicca; 4.75 g), polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P, produced by Rhodia Nicca; 2.25 g) 25 and 1,3-dimethyl-2-imidazolidinone(45.00 g) were measured to a 100 ml - graduated f lask, and f illed to 100 ml with diethyl oxalate. Then it was stirred until unif orm solution to give the emulsif iable concentrate of the present invention (referred as the emulsifiable concentrate of the present invention 2-2, hereinafter).
55 Preparation Example 2-3 Diflufenican( 4. 0 g as active ingredient) , calcium dodecyl benzene sulfonate (Rhodacal 70, surfactant produced by Rhodia 5 Nicca; 5.50 g), polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P, produced by Rhodia Nicca; 1.50 g) and 1,3-dimethyl-2-imidazolidinone(45.00 g) were measured to a 100 ml - graduated flask, and f illed to 100 ml with diethyl oxalate. Then it was stirred until unif orm solution to give the emulsifiable 10 concentrate of the present invention(referredas the emulsifiable concentrate of the present invention 2-3, hereinafter). Test Example 2-1 Each of the emulsifiable concentrate of the present invention 2-1 to 2-3 was diluted by CIPAC standard water D (342ppm) 15 for 100 times in a 100 ml - graduated cylinder with stopper. It was left at 30 *C for 2 hours, and was observed the stability of the emulsion. After that, the aqueous composition which was obtained by diluting the emulsifiable concentrate of the present invention 2-1 to 2-3 with water kept stable emulsion. 20 Preparation Example 2-4 Diflufenican(4.0 g as active ingredient), bromoxynil=octanoate (purity 94. 8 %, 18. 00 g as active ingredient) , ioxynil=octanoate(purity 96 %, 10.5 g as active ingredient), calcium dodecyl benzene sulfonate (NANSA EVM62/H, surfactant 25 produced by Huntsman; 3.00 g) and polyoxypropylene castor oil(Alkamuls OR40, surfactant produced by Rhodia Nicca; 6.00 g) and 1,3-dimethyl-2-imidazolidinone(45.00 g) were measured to a 100 ml - graduated flask, and filled to 100 ml with aromatic hydrocarbon(include Cl to C14 alkylnaphthalene, Solvesso 200 56 ND, produced by Exxon Mobil Chemical Company). Then it Was stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 2-4, hereinafter). 5 Preparation Example 2-5 Diflufenican(4.0 g as active ingredient), bromoxynil=octanoate(18.00 g as active ingredient), ioxynil=octanoate(10.05 gas active ingredient), calcium dodecyl benzene sulfonate (NANSA EVM62/H, surfactant produced by 10 Huntsman; 4.50 g) and polyoxyethylene tristyryl phenyl ether(Soprophor BSU, produced by Rhodia Nicca; 4.5 g) and 1,3-dimethyl-2-imidazolidinone(45.00 g) were measured to a 100 ml - graduated flask, and filled to 100 ml with aromatic hydrocarbon(include C11 to C14 alkylnaphthalene, Solvesso 200 15 ND, produced by Exxon Mobil Chemical Company). Then itwas stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 2-5, hereinafter). Preparation Example 2-6 20 Diflufenican(4.0 g as active ingredient), bromoxynil=octanoate(18.00 g as active ingredient), ioxynil=octanoate(10. 05 g as active ingredient), calcium dodecyl benzene sulfonate (NANSA EVM62/H, surfactant produced by Huntsman; 4.00 g) and polyoxyethylene tristyryl phenyl 25 ether(Soprophor BSU, produced by Rhodia Nicca; 5.0 g) and 1,3-dimethyl-2-imidazolidinone(45.00 g) were measured to a 100 ml - graduated flask, and filled to 100 ml with aromatic hydrocarbon(include C11 to C14 alkylnaphthalene, SoILvesso 200 ND, produced by Exxon Mobil Chemical Company). Then it was stirred 57 until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 2-6, hereinafter). Test Example 2-2 5 Each of the emulsifiable concentrate of the present invention 2-4 to 2-6 was diluted by CIPACstandard water D (342ppm) for 100 times in a 100 ml - graduated cylinder with stopper. It was left at 30 0 C for 0.5 hours, and was observed the stability of the emulsion. After that, the aqueous composition which was 10 obtained by diluting the emulsifiable concentrate of the present invention 2-4 to 2-6 with water kept stable emulsion. Preparation Example 2-7 Diflufenican(2.0 g as active ingredient) , calcium dodecyl benzene sulfonate (NANSA EVM62/H, surfactant produced by 15 Huntsman; 3.00 g), polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P, produced by Rhodia Nicca; 3.00 g) and 1,3-dimethyl-2-imidazolidinone(10.00 g) are measured to a 100 ml - graduated flask, and fill to 100 ml with aromatic hydrocarbon(include C10 to Cl alkylbenzene, Solvesso 150 ND, 20 produced by Exxon Mobil Chemical Company). Then it is stirred until uniform solution to give the emulsifiable concentrate of the present invention. Preparation Example 2-8 Diflufenican(4.0 g as active ingredient), 25 bromoxynil=octanoate(18.00 g as active ingredient), ioxynil=octanoate( 10. 05 g as active ingredient), calciumdodecyl benzene sulfonate (Rodacal 70, surfactant produced by Rhodia Nicca; 3.00 g) and polyoxyethylene alkyl ether(Tensiof ix 96DB10, produced by Omni Chemical; 6.0 g) and 58 1,3-dimethyl-2-imidazolidinone( 3 0.00 g) are measured to a 100 ml - graduated flask, and fill to 100 ml with aromatic hydrocarbon(include ClI to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company). Then it is stirred 5 until uniform solution to give the emulsifiable concentrate of the present invention. Preparation Example 2-9 Diflufenican(4.0 g as active ingredient), bromoxynil=octanoate(18.00 g as active ingredient), 10 ioxynil=octanoate (10. 05 gas active ingredient), calcium dodecyl benzene sulfonate (NANSA EVM62/H, surfactant produced by Huntsman; 5.00 g), polyoxyethylene tristyryl phenyl ether(Soprophor BSU, produced by Rhodia Nicca; 4.00 g), 1,3-dimethyl-2-imidazolidinone (15.00 g) and aromatic 15 hydrocarbon(include C11 to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 10.00 g) are measured to a 100 ml - graduated flask, and fill to 100 ml with diethyl oxalate. Then it is stirred until uniform solution to give the emulsifiable concentrate of the present invention. 20 Preparation Example 2-10 Diflufenican(4.0 g as active ingredient), bromoxynil=octanoate(1 8 .00 g as active ingredient), ioxynil=octanoate(10.05 gas active ingredient) , calcium dodecyl benzene sulfonate (NANSA EVM62/H, surfactant produced by 25 Huntsman; 5.00 g), polyoxyethylene tristyryl phenyl ether(Soprophor BSU, produced by Rhodia Nicca; 4.00 g), 1,3-dimethyl-2-imidazolidinone (20.00 g) and aromatic hydrocarbon(include C11 to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 10. 0 0 g) are measured 59 to a 100 ml - graduated flask, and fill to 100 ml with diethyl oxalate. Then it is stirred until uniform solution to give the emulsifiable concentrate of the present invention. Preparation Example 2-11 5 Diflufenican(4.0 g as active ingredient), bromoxynil=octanoate(18.00 g as active ingredient), ioxynil=octanoate(10. 05 gas active ingredient), calciumdodecyl benzene sulfonate (NANSA EVM62/H, surfactant produced by Huntsman; 4.50 g), polyoxyethylene-polyoxypropylene tristyryl 10 phenyl ether(Soprophor 796/P, surfactant produced by Rhodia Nicca; 4.50 g) and 1,3-dimethyl-2-imidazolidinone (30.00 g) are measured to a 100 ml - graduated flask, and fill to 100 ml with aromatic hydrocarbon(include C10 to C11 alkylbenzene, Solvesso 150 ND, produced by Exxon Mobil Chemical Company). Then it is 15 stirred until uniform solution to give the emulsifiable concentrate of the present invention. Preparation Example 2-12 Diflufenican(3.72 g as active ingredient), bromoxynil=octanoate(16.74 g as active ingredient), 20 ioxynil=octanoate(9. 35 g as active ingredient), calcium dodecyl benzene sulfonate (NANSA EVM62/H, surfactant produced by Huntsman; 4.50 g), polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P, surfactant produced by Rhodia Nicca; 4.50 g) and 1,3-dimethyl-2-imidazolidinone (20.00 g) are 25 measured to a 100 ml - graduated flask, and fill to 100 ml with aromatic hydrocarbon(include C1O to Cl alkylbenzene, Solvesso 150 ND, produced by Exxon Mobil Chemical Company). Then it is stirred until uniform solution to give the emulsifiable concentrate of the present invention.
60 Preparation Example 2-13 Diflufenican(2.68 g as active ingredient), bromoxynil=octanoate(12.0 6 g as active ingredient), ioxynil=octanoate(6.73 g as active ingredient), calcium dodecyl 5 benzene sulfonate (NANSA EVM62/H, surfactant produced by Huntsman; 4.50 g), polyoxyethylene-polyoxypropylene tristyryl phenyl ether(Soprophor 796/P, surfactant produced by Rhodia Nicca; 4.50 g) and 1,3-dimethyl-2-imidazolidinone (15.00 g) are measured to a 100 ml - graduated flask, and fill to 100 ml with 10 aromatic hydrocarbon(include CIO to C11 alkylbenzene, Solvesso 150 ND, produced by Exxon Mobil Chemical Company). Then it is stirred until uniform solution to give the emulsifiable concentrate of the present invention. 15 Preparation Example 3-1 Diflufenican(purity 93.2 %, 3.72 g as active ingredient), bromoxynil=octanoate(purity9 4 .8%, 16.74 gas active ingredient), ioxynil=octanoate(purity 96 %, 9.35 g as active ingredient), calcium dodecyl benzene sulfonate (3.67 g), polyoxyethylene 20 tristyryl phenyl ether(HLB 12.6; 6.33 g), sorbitan mono laurate(HLB 8.6; 3.00 g), aromatic hydrocarbon(include CI to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil ChemicalCompany; 5.00g) andN-methyl-2-pyrrolidone(5.70g) were measured in a 100 ml graduated flask. Then diethyl oxalate was 25 added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 3-1, hereinafter). Preparation Example 3-2 61 At 20 *C, diflufenican(purity 93.2 %, 3.72 g as active ingredient), bromoxynil=octanoate(purity 94.8 %, 16.74 g as active ingredient), ioxynil=octanoate(purity 96 %, 9.35 g as active ingredient) , calcium dodecyl benzene sulfonate (3. 95 g), 5 polyoxyethylene tristyryl phenyl ether(HLB 12.6; 7.55 g), sorbitan mono laurate(HLB 8.6; 1.50 g), aromatic hydrocarbon(include Cl to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 10.00 g) and 1,3-dimethyl-2-imidazolidinone(15.00 g) were measured in a 100 10 ml graduated flask. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention (referred as the emulsif iable concentrate of the present invention 3-2, hereinafter). 15 Preparation Example 3-3 At 20 *C, diflufenican(purity 93.2 %, 2.68 g as active ingredient), bromoxynil=octanoate(purity 94.8 %, 12.06 g as active ingredient), ioxynil=octanoate(purity 96 %, 6.37 g as active ingredient), calcium dodecyl benzene sulfonate (2.70 g), 20 polyoxyethylene tristyryl phenyl ether(HLB 12.6; 6.30 g), sorbitan mono laurate(HLB 8.6; 1.00 g) and aromatic: hydrocarbon(include C11 to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 5.00 g) were measured in a 100 ml graduated flask. Then diethyl oxalate was added until 25 the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention (referred as the emulsifiable concentrate of the present invention 3-3, hereinafter). Test Example 3-1 62 Each of the emulsifiable concentrate of the present invention 3-1 to 3-3 was filled in the bottle. They were kept in refrigerator for 7 days at 0 * C. Then each bottle was taken out from the refrigerator, and kept for about 30 minutes at room 5 temperature. After that, it was observed whether solid substance existed or not in the bottom of the bottle. There were no solid substance in each of them, and each of them was clear and uniform solution. Test Example 3-2 10 Into a 100ml-graduated cylinderwith stopper, 99ml of CIPAC standard water D (342ppm) were charged. The graduated cylinder was put in a thermostat andwas kept at 300 C forawhile. Further, 1 ml each of the emulsifiable concentrate of the present invention 3-1 to 3-3 were added into the graduated cylinder, and the cylinder 15 was turned upside down 10 times at a rate of once per two seconds. Then, it was put in a thermostat again and left at 30 *C for 2 hours. After that, each of the state of the emulsion in the graduated cylinder was observed. Each was provided uniform emulsion state. 20 Preparation Example 3-4 At 20 *C, diflufenican(purity 93.2 %, 2.68 g as active ingredient), bromoxynil=octanoate(purity 94.8 %, 12.06 g as active ingredient), ioxynil=octanoate(purity 96 %, 6.37 g as active ingredient) , calcium dodecyl benzene sulfonate (2. 90 g) , 25 polyoxyethylene tristyryl phenyl ether(HLB 12.6; 12.20 g), sorbitan mono oleate(HLB 4.3; 1.00 g) and aromatic hydrocarbon(include C11 to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 10.0) g) were measured in a 100 ml graduated flask. Then diethyl oxalate was 63 added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 3-4, hereinafter). 5 Preparation Example 3-5 At 20 *C, diflufenican(purity 93.2 %, 2.68 g as active ingredient), bromoxynil=octanoate(purity 94.8 %, 12.06 g as active ingredient), ioxynil=octanoate(purity 96 %, 6.37 g as active ingredient), calcium dodecyl benzene sulfonate (2.90 g), 10 polyoxyethylene tristyryl phenyl ether(HLB 12.6; 12.20 g), sorbitan mono laurate(HLB 8.6; 1.00 g) and aromatic hydrocarbon(include C11 to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 10.00 g) were measured in a 100 ml graduated flask. Then diethyl oxalate was 15 added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 3-5, hereinafter). Test Example 3-3 20 Each of the emulsifiable concentrate of the present invention 3-4 to 3-5 was filled in the bottle. They were kept in refrigerator for 7 days at -5 " C. Then each bottle was taken out from the refrigerator, and kept for about 30 minutes at room temperature. After that, it was observedwhether solid substance 25 existed or not in the bottom of the bottle. There were no solid substance in each of them, and each of them was clear and uniform solution. Preparation Example 3-6 Diflufenican(purity 93.2 %, 3.72 g as active ingredient) , 64 bromoxynil=octanoate (purity 94.8 %, 16.74 g as active ingredient), ioxynil=octanoate(purity 96 %, 9.35 g as active ingredient), calcium dodecyl benzene sulfonate (5.00 g), polyoxyethylene tristyryl phenyl ether (HLB 12.6; 4 .00 g) , sorbitan mono oleate (HLB 5 4.3; 1.00 g), aromatic hydrocarbon(include Cll to Cl4 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 10.00 g) and N-methyl-2-pyrrolidone(5.70 g) are measured in a 100 ml graduated flask. Then diethyl oxalate is added until the total amount being 100 ml. It is stirred until 10 uniform solution to give the emulsifiable concentrate of the present invention. Preparation Example 3-7 Diflufenican(purity 93.2 %, 3. 72 g as active ingredient) , bromoxynil=octanoate (purity 94.8 %, 16.74 g as active ingredient.) , 15 ioxynil=octanoate(purity 96 %, 9.35 g as active ingredient), calcium dodecyl benzene sulfonate (5.00 g), polyoxyethylene tristyryl phenyl ether(HLB 12.6; 4.00 g), sorbitan mono laurate(HLB 8.6; 1.00 g), aromatic hydrocarbon(include Cl to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil 20 Chemical Company; 10.00 g) and N-methyl-2-pyrrolidone(5.70 g) are measured in a 100 ml graduated flask. Then diethyl oxalate is added until the total amount being 100 ml. It is stirred until uniform solution to give the emulsifiable concentrate of the present invention. 25 Preparation Example 3-8 Diflufenican(purity 93.2 %, 3.72 g as active ingredient), bromoxynil=octanoate(purity94.8%, 16.74 gas active ingredient), ioxynil=octanoate(purity 96 %, 9.35 g as active ingredient), calcium dodecyl benzene sulfonate (5.00 g), polyoxyethylene 65 tristyryl phenyl ether(HLB 12.6; 4.00 g), sorbitan mono laurate(HLB 8.6; 1.00 g), aromatic hydrocarbon(include C11 to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 12.00 g) and N,N-dimethylacetamide(5.70 g) are 5 measured in a 100 ml graduated flask. Then diethyl oxalate is added until the total amount being 100 ml. It is stirred until. uniform solution to give the emulsifiable concentrate of the present invention. Preparation Example 3-9 10 Diflufenican(purity 93.2 %, 3.72 g as active ingredient), bromoxynil=octanoate (purity 94 .8%, 16. 74 g as active ingredient) , ioxynil=octanoate(purity 96 %, 9.35 g as active ingredient), calcium dodecyl benzene sulfonate (5.00 g), polyoxyethylene caster oil(HLB13.5; 4.00 g), sorbitanmono laurate(HLB 8.6; 1.00 15 g), aromatic hydrocarbon (include Cl to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 12.00 g) and N-methyl-2-pyrrolidone(5.70 g) are measured in a 100 ml graduated flask. Then diethyl oxalate is added until the total amount being 100 ml. It is stirred until uniform solution to 20 give the emulsifiable concentrate of the present invention. Preparation Example 3-10 Diflufenican(purity 93.2 %, 3.72 g as active ingredient), bromoxynil=octanoate (purity 94 .8 %, 16. 74 gas active ingredient) , ioxynil=octanoate(purity 96 %, 9.35 g as active ingredient), 25 calcium dodecyl benzene sulfonate (5.00 g), sorbitan mono laurate(HLB 8.6; 5.00 g), aromatic hydrocarbon(include Cll to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 12.00 g) and 1,3-dimethyl-2-imidazolidinone(5.7 g) are measured in a 100 ml 66 graduated flask. Then diethyl oxalate is added until the total amount being 100 ml. It is stirred until uniform solution to give the emulsifiable concentrate of the present invention. Preparation Example 3-11 5 Diflufenican(purity 93.2 %, 3.72 gas active ingredient), calcium dodecyl benzene sulfonate (5.00 g), polyoxyethylene tristyryl phenyl ether(HLB 12.6; 4.00 g), sorbitan mono laurate(HLB 8.6; 1.00 g), aromatic hydrocarbon(include Cl to C14 alkylnaphthalene, Solvesso 200 10 ND, produced by Exxon Mobil Chemical Company; 12.00 g) and N-methyl-2-pyrrolidone(5.70 g) are measured in a 100 ml graduated flask. Then diethyl oxalate is added until the total amount being 100 ml. It is stirred until uniform solution to give the emulsifiable concentrate of the present invention. 15 Preparation Example 4-1 Diflufenican(4.00 g as active ingredient), bromoxynil=octanoate(18.00 g as active ingredient), ioxynil=octanoate(10.05 gas active ingredient), calcium dodecyl 20 benzene sulfonate (3.20 g), butylpolyalkyleneoxide block copolymer(Toximul 8320, produced by Stepan; 4.80 g), aromatic hydrocarbon(include C11 to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 5.00 g) 1,3-dimethyl-2-imidazolizinone(15.00 g) and 25 N-methyl-2-pyrrolidone(5.50 g) weremeasured inal00ml graduated flask. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 4-1, 67 hereinafter). Preparation Example 4-2 Diflufenican(4.00 g as active ingredient), bromoxynil=octanoate(1 8 .00 g as active ingredient), 5 ioxynil=octanoate(10.05 gas active ingredient), calcium dodecyl benzene sulfonate (3.20 g), polyalkyleneoxide block copolymer(Toximul 8323, produced by Stepan; 4.80 g), aromatic hydrocarbon(include Cl to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 5.00 g) 10 1,3-dimethyl-2-imidazolizinone(15.00 g) and N-methyl-2-pyrrolidone(5.50g) weremeasuredin a100ml graduated flask. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as 15 the emulsifiable concentrate of the present invention 4-2, hereinafter). Preparation Example 4-3 Diflufenican(4.00 g as active ingredient), bromoxynil=octanoate(18.00 g as active ingredient), 20 ioxynil=octanoate(10.05 gas active ingredient), calcium dodecyl benzene sulfonate (3.20 g), polyalkyleneoxide block copolymer(Step-Flow 26, produced by Stepan; 4.80 g) , aromatic hydrocarbon(include C11 to C14 alkylnaphthalene, Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 5.00 g) 25 1,3-dimethyl-2-imidazolizinone(15.00 g) and N-methyl-2-pyrrolidone(5 .50g) were measured in a 10 0 ml graduated flask. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the emulsifiable concentrate of the present invention(referred as 68 the emulsifiable concentrate of the present invention 4-3, hereinafter). Preparation Example 4-4 Diflufenican(4.00 g as active ingredient), 5 bromoxynil=octanoate(18.00 g as active ingredient), ioxynil=octanoate(10.05 g as active ingredient), calcium dodecyl benzene sulfonate (3.20 g), polyalkyleneoxide block copolymer(Ethylan NS 500 LQ, produced by Akzo Nobel; 4.80 g)., aromatic hydrocarbon(include C11 to C14 alkylnaphthalene, 10 Solvesso 200 ND, produced by Exxon Mobil Chemical Company; 5.00 g) 1,3-dimethyl-2-imidazolizinone(15.00 g) and N-methyl-2-pyrrolidone (5 .50 g) were measured in a 100 ml graduated flask. Then diethyl oxalate was added until the total amount being 100 ml. It was stirred until uniform solution to give the 15 emulsifiable concentrate of the present invention(referred as the emulsifiable concentrate of the present invention 4-4, hereinafter). Test Example 4-1 Into a 10 0ml-graduated cylinder with stopper, 98nlof CIPAC 20 standard water D (342ppm) were charged. The graduated cylinder was put in a thermostat and was kept at 30 * C for awhile. Further, 2 ml each of the emulsifiable concentrate of the present invention 4-1 to 4-4 were added into the graduated cylinder, and the cylinder was turned upside down 10 times at a rate of once per two seconds. 25 Then, it was put in a thermostat again and left at 30 0 C for 2 hours. After that, each of the state of the emulsion in the graduated cylinder was observed. Each was provided uniform emulsion state.
69 INDUSTRIAL APPLICABILITY The emulsifiable concentrate of the present invention is useful as pesticide formulation because it has an excellent stability of the emulsion even after diluted with water. 5

Claims (28)

1. An emulsifiable concentrate, which is characterized by comprising 5 2' , 4 '-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinaanilide; the compound shown by the below formula (1): R O A10 O R2 (1) 0 0 wherein, in the formula, R1 and R represent alkyl groups, A represents a single bond or an alkylene group, and the sum of 10 the number of carbon atoms which consist of the groups of R 1 , R2 and A is 2 to 8; and a surfactant.
2. An emulsifiable concentrate, which is 15 characterized by comprising 0.5 to 5 % by weight of 2' , 4 '-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide; 5 to 80 % by weight of the compound shown by the below formula (1): R O 1, A 0 R2 (1) 20 0 0 wherein, in the formula, Ri and R 2 represent alkyl groups, A represents a single bond or an alkylene group, and the sum of the number of carbon atoms which consist of the groups of R 1 , R2 and A is 2 to 8; and 25 4 to 20 % by weight of a surfactant. 71
3. The emulsifiable concentrate according to claim 1 or 2, wherein the compound shown by the formula (1) is diethyl oxalate. 5
4. The emulsifiable concentrate according to any one of claims 1 to 3, wherein the ratio of the compound shown by the formula (1) is 5 to 80 by weight for one weight of 2' ,4' -difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide. 10
5. The emulsifiable concentrate according to any one of claims 1 to 4, wherein the emulsifiable concentrate comprises an aromatic hydrocarbon. 15
6. The emulsifiable concentrate according to any one of claims 1 to 4, wherein the emulsifiable concentrate comprises 1 to 40 % by weight of an aromatic hydrocarbon.
7. The emulsifiable concentrate according to any one 20 of claims 1 to 6, wherein the emulsifiable concentrate comprises 1,3-dimethyl-2-imidazolidinone.
8. The emulsifiable concentrate according to any one of claims 1 to 6, wherein the emulsifiable concentrate comprises 25 5 to 60 by weight of 1,3-dimethyl-2-imidazolidinone.
9. The emulsifiable concentrate according to any one of claims 1 to 8, wherein the surfactant is an anionic surfactant and a nonionic surfactant; and the ratio by weight of the anionic 72 surfactant and the nonionic surfactant is 1:0.1 to 1:10.
10. The emulsifiable concentrate according to claim 9, wherein the anionic surf actant is an alkylbenzenesulfonic acid 5 salt.
11. The emulsifiable concentrate according to claim 9 or 10, wherein the nonionic surf actant is the nonionic surfactant which has polyalkylene oxide structure in the molecule. LO
12. The emulsifiable concentrate according to claim 11, wherein the nonionic surf actant which has polyalkylene oxide structure in the molecule is the surfactant selected from the group consisting of polyoxyethylene-polyoxypropylene tristyryl 15 phenyl ether, polyoxyethylene tristyryl phenyl ether and polyoxyethylene castor oil.
13. The emulsifiable concentrate according to claim 9 or 10, wherein the nonionic surfactant is a sorbitan :Eatty acid 20 ester.
14. The emulsifiable concentrate according to claim 1, wherein the emulsifiable concentrate comprises 4-cyano-2,6-dibromophenyl octanoate and 25 4-cyano-2,6-diiodophenyl octanoate.
15. The emulsifiable concentrate according to claim 2, wherein the emulsifiable concentrate comprises 1 to 30 % by weight of 4-cyano-2,6-dibromophenyl octanoate and 1 to 30 % by 73 weight of 4-cyano-2,6-diiodophenyl octanoate.
16. The emulsifiable concentrate according to claims 14 or 15, wherein the ratio of the compound shown by the formula 5 (1) is 5 to 80 by weight for the weight of 2' ,4' -difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide.
17. The emulsifiable concentrate according to any one of claims 14 to 16, wherein the surf actant is an anionic surf actant 10 and a nonionic surfactant; and the ratio by weight of the anionic surfactant and the nonionic surfactant is 1:0.1 to 1:10.
18. The emulsifiable concentrate according to any one of claims 11 to 14, wherein the compound shown by th~e formula 15 (1) is diethyl oxalate.
19. The emulsifiable concentrate according to any one of claims 14 to 18, wherein the emulsifiable concentrate comprises an aromatic hydrocarbon. 20
20. The emulsifiable concentrate, which is characterized by comprising 2' ,4' -difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotnanilide; 1,3-dimethyl-2-imidazolidinone; 25 an aromatic hydrocarbon; and a surfactant.
21. The emulsifiable concentrate, which is characterized by comprising 74 1 to 5 % by weight of 2', 4' -difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide; 5 to 60 % by weight of 1,3-dimethyl-2-imidazolidinone; 10 to 50 % by weight of an aromatic hydrocarbon; and 5 4 to 20 % by weight of a surfactant.
22. The emulsifiable concentrate, which i: characterized by comprising 2' ,4'-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide; 10 a sorbitan fatty acid ester; an anionic surfactant; and an aromatic hydrocarbon.
23. The emulsifiable concentrate, which is 15 characterized by comprising 0.5 to 5 % by weight of 2' ,4'-difluoro-2-(aaa-trifluoro-m-tolyloxy )nicotinanilide; 0.5 to 10 % by weight of a sorbitan fatty acid ester; 0.5 to 10 % by weight of an anionic surfactant; and 20 10 to 90 % by weight of an aromatic hydrocarbon.
24. An aqueous composition which is obtainable by diluting the emulsifiable concentrate according to any one of claims 1 to 23 with water. 25 75
25. An emulsifiable concentrate, substantially as hereinbefore described with reference to any one of the examples.
26. An aqueous composition which is obtainable by diluting the emulsifiable concentrate of claim 25. s
27. An emulsifiable concentrate, according to any one of claims 1 to 23 or 25 when used as a pesticide.
28. An aqueous composition according to claim 24 or 27 when used as a pesticide. Dated 20 April, 2011 Sumitomo Chemical Company, Limited Patent Attorneys for the Applicant/Nominated Person SPRUSON & FERGUSON
AU2011201960A 2005-03-31 2011-04-29 Emulsifiable concentrate Ceased AU2011201960B2 (en)

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Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5066880B2 (en) * 2006-09-27 2012-11-07 住友化学株式会社 Emulsion composition
JP5092428B2 (en) * 2007-01-31 2012-12-05 住友化学株式会社 Pesticide solution containing hydrophobic agrochemical active compound
JP5262131B2 (en) * 2008-01-24 2013-08-14 住友化学株式会社 Emulsion composition
BE1018441A3 (en) * 2009-11-30 2010-11-09 Globachem EMULGABLE CONCENTRATE OF A PESTICIDE.
CN104365603A (en) * 2014-09-25 2015-02-25 南京华洲药业有限公司 Mixed herbicide containing diflufenican and bromoxynil octanoate, and preparation method thereof
US20220304305A1 (en) * 2019-09-11 2022-09-29 Bayer Aktiengesellschaft Highly effective formulations on the basis of 2-[(2,4-dichlorphenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinones and preemergence herbicides

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3397054A (en) 1962-08-30 1968-08-13 Schering Corp Process for controlling plant growth
IL64220A (en) 1980-11-21 1985-06-30 May & Baker Ltd Nicotinamide derivatives,their preparation and their use as herbicides
GR861894B (en) 1985-07-23 1986-11-24 May & Baker Ltd Herbicidal method comprising the use of diflufenican
GB8617740D0 (en) * 1986-07-21 1986-08-28 May & Baker Ltd Compositions of matter
GB8630806D0 (en) 1986-12-23 1987-02-04 May & Baker Ltd Compositions of matter
DE19701123B4 (en) 1996-02-06 2008-12-24 Basf Se Use of a mixture for the production of pesticidal pesticides
DE19633271A1 (en) * 1996-08-19 1998-02-26 Basf Ag Liquid formulation of ethyl (Z) -2-chloro-3- [2-chloro-5- (4,5,6,7-tetrahydro-1,3-dioxoisoindoldion-2-yl) phenyl] acrylate
US5834400A (en) * 1997-04-29 1998-11-10 Isp Investments Inc. Emulsifiable concentrate for a low dosage fluorinated agricultural chemical
US6566308B1 (en) * 1999-01-29 2003-05-20 Basf Aktiengesellschaft Emulsifiable concentrate containing one or more pesticides and adjuvants
GB9912562D0 (en) * 1999-05-28 1999-07-28 Zeneca Ltd Herbicide composition
DE10048797A1 (en) * 2000-10-02 2002-04-18 Bayer Ag Emulsion for protecting timber (e.g. green timber) or timber materials against attack by wood-destroying or wood-discoloring microorganisms contains mixture of tebuconazole and propiconazole and phenol/styrene polyglycol ether derivative
DE10108472A1 (en) 2001-02-22 2002-09-05 Aventis Cropscience Gmbh Agrochemical formulations
RU2197206C1 (en) * 2001-08-15 2003-01-27 Свадовский Александр Игоревич Method for treating the cases of glaucoma
DE10231615A1 (en) * 2002-07-12 2004-02-05 Bayer Cropscience Gmbh Fixed adjuvants
DE10343390A1 (en) * 2003-09-19 2005-04-14 Bayer Cropscience Gmbh Surfactant / solvent mixtures

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GB2425955A (en) 2006-11-15
FR2921231A1 (en) 2009-03-27
GB2425955B (en) 2007-05-16
LU91232B1 (en) 2007-04-02
AU2011201960B2 (en) 2011-12-15
FR2883701B1 (en) 2010-01-08
AU2011201959A1 (en) 2011-05-19
AU2011201959B2 (en) 2011-08-25
DE102006063013B3 (en) 2018-10-18
DE102006013999A1 (en) 2006-10-05
FR2921233B1 (en) 2012-07-06
AU2006200731B2 (en) 2011-05-19
NL1032547A1 (en) 2006-11-13
NL1031386C2 (en) 2006-10-09
GB0606184D0 (en) 2006-05-10
AU2006200731A1 (en) 2006-10-19
FR2921231B1 (en) 2010-10-22
FR2883701A1 (en) 2006-10-06
DE102006013999B4 (en) 2017-03-30
BE1017082A3 (en) 2008-02-05
FR2921233A1 (en) 2009-03-27
NL1032546C2 (en) 2007-05-08
NL1032547C2 (en) 2007-05-08
NL1032546A1 (en) 2006-11-13

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