(19) &  

(11) EP 2 433 987 A1

(12) EUROPEAN PATENT APPLICATION published in accordance with Art. 153(4) EPC

(43) Date of publication: (51) Int Cl.: 28.03.2012 Bulletin 2012/13 C08L 71/02 (2006.01) A01N 25/04 (2006.01) B27K 3/50 (2006.01) C08K 5/10 (2006.01) (2006.01) (21) Application number: 10777519.9 C08K 5/42

(22) Date of filing: 10.05.2010 (86) International application number: PCT/JP2010/003169

(87) International publication number: WO 2010/134279 (25.11.2010 Gazette 2010/47)

(84) Designated Contracting States: (72) Inventors: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB • ARAI, Shigebumi GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO Odawara-shi PL PT RO SE SI SK SM TR Kanagawa 250-0280 (JP) Designated Extension States: • KUBOTA, Tetsuo BA ME RS Odawara-shi Kanagawa 250-0280 (JP) (30) Priority: 20.05.2009 JP 2009121611 (74) Representative: Wibbelmann, Jobst (71) Applicant: Nippon Soda Co., Ltd. Wuesthoff & Wuesthoff Tokyo 100-8165 (JP) Patent- und Rechtsanwälte Schweigerstrasse 2 81541 München (DE)

(54) COMPOSITION FOR PREPARING EMULSION OR MICROEMULSION FORMULATIONS

(57) Provided is a composition for preparing emul- alkylene aralkenyl phenyl ether, a component (B): a poly- sion or microemulsion formulations that demonstrates fa- oxyalkylene sorbitan alkylate, a component (C): a dialkyl- vorable dilution properties without being affected by the sulfosuccinate, and a component (D): an ester ether- solubilities of constituent components. The composition based solvent. An emulsion or microemulsion formula- for preparing emulsion or microemulsion formulations tion containing the composition is also provided. contains a component (A): a polyoxyalkylene allyl phenyl ether, polyoxyalkylene aralkyl phenyl ether or polyoxy- EP 2 433 987 A1

Printed by Jouve, 75001 PARIS (FR) 1 EP 2 433 987 A1 2

Description a phenolic OH group, formaldehyde and an NH functional group; f2) a carbonate, sulfate and phosphate of an al- TECHNICAL FIELD kaline metal or alkaline earth metal; f3) a polymer con- taining repeating succinyl units; f4) a non- ionically or ion- [0001] The present invention relates to a composition 5 ically modified compound selected from the group con- for preparing emulsion or microemulsion formulations. sistingof alkoxylate, alkylolamide, ester, amine oxide and More particularly, the present invention relates to a com- alkylpolyglycoside; f5) a reaction product of an alkylene position for preparing emulsion or microemulsion formu- oxide and sorbitan ester, an oxyalkylated acetylenediol lations that demonstrate favorable diluting properties and acetylene glycol, and an oxyalkylated phenol; f6) ion- without being affected by the solubilities of constituent 10 ically or non-ionically modified polymeric surfactants se- components. lected from the group consisting of homo- and copoly- The present application claims priority on the basis of mers, grafts and graft copolymers, and random and linear Japanese Patent Application No. 2009-121611 filed in block copolymers; f7) anionic surfactants such as ether Japan on May 20, 2009, the contents of which are incor- sulfates, ether carboxylates and phosphate esters; f8) porated herein by reference. 15 anionic surfactants such as sulfosuccinate esters, alkyl- benzene sulfonates and salts of polyacrylic acid, poly- BACKGROUND ART ethylene sulfonic acid, polystyrene sulfonic acid, polymethacrylic acid or polyphosphoric acid; and f9) [0002] Known examples of the types of the forms of lignin-based compounds, and particularly lignosul- agricultural chemicals include: milky white formulations 20 fonates. in the form of concentrated oil-in-water emulsions ob- [0007] Patent Document 5 discloses a microemulsion- tained by emulsifying and dispersing a water-insoluble formable concentrate of a hydrophobic agricultural agricultural chemical active ingredient in water in the form chemical containing: (a) at least one type of hydrophobic of fine particles by adding an emulsifier (emulsion formu- agricultural chemical, (b) a concentrate of a first solvent lations (emulsion, oil in water: EW or concentrated emul- 25 selected from alkyl alkanoates, a polyvalent alcohol, a sion: CE)); and thermodynamically stable and transpar- polyvalent alcohol concentration product and a mixture ent formulations obtained by mixing mutually incompat- thereof, and (c) at least one type of surfactant. Examples ible water and oil in the manner of ordinary emulsions, of the surfactant include cationic surfactants such as but consisting of dispersed particles that are much small- polyalkoxylated aliphatic amines, nonionic surfactants er (mean particle diameter: 0.1 Pm or less) than the par- 30 such as polyalkylene oxide alkyl ethers, and anionic sur- ticles of ordinary emulsions (microemulsion formulations factants such as alkylbenzene sulfonates. (microemulsion: ME)). [0008] However, the emulsion or microemulsion for- [0003] More specifically, Patent Document 1 discloses mulations described in these documents may require a a wood preservative having as an active ingredient there- large amount of surfactant or emulsifier corresponding of an anionic surfactant containing a sulfonate or lauryl- 35 to the solubility of the active ingredient. In such cases, a sulfate ester. A preservative containing a sulfosuccinate large amount of foam may form during preparation of the ester is described as a comparative example of a formu- formulation and may be difficult to remove from the for- lation in Patent Document 1. mulation container. In the case of diluting the formula- [0004] Patent Document 2 discloses a wood preserv- tions, the stability of the emulsion or microemulsion may ative, ant repellent and anti-mold agent containing as an 40 decrease. In addition, the use of a large amount of sur- active ingredient thereof a polyoxyalkylene alkyl ether factant for the purpose of enhancing solubility results in obtained by adding at least one type of compound se- increased costs. lected from the group consisting of ethylene oxide, pro- pylene oxide and butylene oxide to an alkyl alcohol. A [Prior Art Document] preservative containing a sorbitan fatty acid ester- based 45 surfactant and a preservative containing polyoxyethyl- [Patent Documents] ene styrenated phenyl ether are described as compara- tive examples of formulations in Patent Document 2. [0009] [0005] Patent Document 3 describes a microemulsion preparation containing: a) one or more agricultural chem- 50 [Patent Document 1] Japanese Patent Application ical active ingredients; b) one or more non-alcoholic or- No. 2007-15959 ganic solvents; c) one or more anionic surfactants; and [Patent Document 2] Japanese Patent Application d) one or more nonionic surfactants. No. 2006-199687 [0006] Patent Document 4 discloses an emulsion con- [Patent Document 3] Japanese Patent Application taining a surfactant. Examples of preferable surfactants 55 Laid-Open Publication (Translation of PCT Applica- include: f1) alkoxylation product obtained by ethylene ox- tion) No. 2006-509807 ide alkoxylation or propylene oxide alkoxylation of a con- [Patent Document 4] Japanese Patent Application densation product of an aromatic compound containing Laid-Open Publication No. 2002-194205

2 3 EP 2 433 987 A1 4

[Patent Document 5] Japanese Patent Application (5) The composition for preparing emulsion or mi- Laid-Open Publication No. 2008-308508 croemulsion formulations described in (4) above, wherein the total amount of component (A), compo- SUMMARY OF THE INVENTION nent (B) and component (C) is 20% by weight to 50% 5 by weight, the total amount of component (D) and PROBLEMS TO BE SOLVED BY THE INVENTION component (E) is 50% by weight to 80% by weight, and the amount of component (E) is 10% by weight [0010] With the foregoing in view, an object of the to 40% by weight based on a value of 100% by weight present invention is to provide a composition for prepar- for the total amount of component (A), component ing emulsion or microemulsion formulations having favo- 10 (B), component (C), component (D) and component rable diluting properties without being affected by the sol- (E). ubilities of constituent components. (6) The composition for preparing emulsion or mi- croemulsion formulations described in any one of (1) MEANS FOR SOLVING THE PROBLEMS to (5) above, further including a component (F): an 15 agricultural chemical active ingredient. [0011] In order to solve the aforementioned problems, (7) The composition for preparing emulsion or mi- the inventors of the present invention found that a favo- croemulsion formulations described in (6) above, in- rable emulsion or microemulsion formulation demon- cluding 1 to 43 parts by weight of the component (F) strating little foaming can be prepared by mixing an an- based on 100 parts by weight of the total amount of ionic surfactant with a certain type of combination of no- 20 component (A), component (B), component (C), nionic surfactants and further combining with a specific component (D) and component (E). polar solvent therewith. The present invention was com- (8) An emulsion or microemulsion formulation, in- pleted by conducting further studies on the basis of this cluding: the composition for preparing emulsion or finding. microemulsion formulations described in any one of [0012] Namely, the present invention includes the as- 25 (1) to (7) above. pects described below. (9) An emulsion or microemulsion formulation ob- tained by diluting with water the composition for pre- (1) A composition for preparing emulsion or microe- paring emulsion or microemulsion formulations de- mulsion formulations, including: scribed in any one of (1) to (7) above. 30 (10) The emulsion or microemulsion formulation de- component (A): a polyoxyalkylene allyl phenyl scribed in (8) or (9) above, which is used to preserve ether, polyoxyalkylene aralkyl phenyl ether or wood. polyoxyalkylene aralkenyl phenyl ether; component (B): a polyoxyalkylene sorbitan EFFECTS OF THE INVENTION alkylate; 35 component (C): a dialkylsulfosuccinate; and [0013] The composition for preparing emulsion or mi- component (D): an ester ether-based solvent. croemulsion formulations according to the present inven- tion is able to provide an emulsion or microemulsion for- (2) The composition for preparing emulsion or mi- mulation that demonstrates favorable diluting properties croemulsion formulations described in (1) above, 40 without being affected by the solubilities of constituent wherein the ratio of the total amount of component components. The composition for preparing emulsion or (A) and component (B) to the amount of component microemulsion formulations according to the present in- (C) is within the range of 1:2 to 1:7, and the ratio of vention permits easy handling during preparation as a the amount of component (A) to the amount of com- result of demonstrating little foaming. Moreover, the com- ponent (B) is within the range of 2:1 to 1:2. 45 position for preparing emulsion or microemulsion formu- (3) The composition for preparing emulsion or mi- lations according to the present invention enables an croemulsion formulations described in (1) or (2) emulsion or microemulsion to be stably maintained even above, wherein the total amount of component (A), if diluted with water. component (B) and component (C) is 20% by weight to 50% by weight, and the amount of component (D) 50 DESCRIPTION OF THE EMBODIMENTS is 50% by weight to 80% by weight based on a value of 100% by weight for the total amount of component [0014] The following provides a detailed explanation (A), component (B), component (C) and component of the present invention. (D). (4) The composition for preparing emulsion or mi- 55 1) Composition for Preparing Emulsion or Microemulsion croemulsion formulations described in (1) or (2) Formulations above, further including a component (E): a polar solvent other than the ester ether-based solvent. [0015] The composition for preparing emulsion or mi-

3 5 EP 2 433 987 A1 6 croemulsion formulations according to the present inven- ponent (A) may be used alone, or two or more types may tion contains a component (A), a component (B), a com- be used in combination. ponent (C) and a component (D), and as necessary, a component (E) and/or a component (F). [Component B] 5 [Component (A)] [0019] The component (B) used in the composition for preparing emulsion or microemulsion formulations ac- [0016] The component (A) used in the composition for cording to the present invention is a polyoxyalkylene preparing emulsion or microemulsion formulations ac- sorbitan alkylate. cording to the present invention is a polyoxyalkylene allyl 10 Specific examples of polyoxyalkylene sorbitan alkylates phenyl ether, polyoxyalkylene aralkyl phenyl ether or include polyoxyethylene sorbitan oleate, polyoxyethyl- polyoxyalkylene aralkenyl phenyl ether. ene sorbitan stearate, polyoxyethylene sorbitan palmi- Polyoxyalkylene allyl phenyl ethers are obtained by link- tate and polyoxyethylene-polyoxypropylene sorbitan di- ing a polyoxyalkylene group and an allyl phenyl group laurate. Among these, polyoxyethylene sorbitan mo- with an etherbond. Polyoxyalkylene aralkyl phenyl ethers 15 nooleate is preferable. are obtained by linking a polyoxyalkylene group and an aralkyl phenyl group with an ether bond. Polyoxyalkylene [Component C] aralkenyl phenyl ethers are obtained by linking a poly- oxyalkylene group and an aralkenyl phenyl group with [0020] The component (C) used in the composition for an ether bond. 20 preparing emulsion or microemulsion formulations ac- [0017] Examples of the polyoxyalkylene group include cording to the present invention is a dialkyl sulfosucci- a polyoxyethylene group, a polyoxypropylene group, a nate. polyoxybutylene group and a polyoxyethylene-polyoxy- Examples of the dialkyl sulfosuccinate include dibutyl sul- propylene group. The degree of polymerization of the fosuccinate, dioctyl sulfosuccinate and dilauryl sulfosuc- polyoxyalkylene group is normally 2 to 50, preferably 5 25 cinate. Examples of metals used to form a salt include: to 30 and more preferably 10 to 25. alkaline metals such as sodium, potassium or lithiuml; The allyl phenyl group is obtained by substituting at least and alkaline earth metals such as beryllium, magnesium one allyl group in a phenyl group, the aralkyl phenyl group or calcium. is obtained by substituting at least one aralkyl group in a Among these dialkyl sulfosuccinates, magnesium dioctyl phenyl group, and the aralkenyl phenyl group is obtained 30 sulfosuccinate is preferable. by substituting at least one aralkenyl group in a phenyl [0021] Although there are no particular limitations on group. Specific examples of the allyl phenyl group, the the mixing ratio of the components (A) to (C), the ratio of aralkyl phenyl group and the aralkenyl phenyl group in- the total amount of component (A) and component (B) clude a monoallyl phenyl group, a diallyl phenyl group, a to the amount of component (C) is preferably 1:2 to 7:1 triallyl phenyl group, a monobenzyl phenyl group, 35 a and more preferably2:1 to 4:1, and the ratio ofthe amount dibenzyl phenyl group, a tribenzyl phenyl group, a mon- of component (A) to the amount of component (B) is pref- ostyryl phenyl group, a distyryl phenyl group and a tris- erably 2:1 to 1:2 and more preferably 3:2 to 2:3. tyryl phenyl group. A substituent such as an alkyl group may be present in an aromatic ring in the aralkyl group (Component D) or aralkenyl group. In addition, examples of the aromatic 40 ring in the aralkyl group or aralkenyl group include a ben- [0022] The component (D) used in the composition for zene ring and naphthalene ring. preparing emulsion or microemulsion formulations ac- [0018] Specific examples of component (A) include: cording to the present invention is an ester ether-based polyoxyethylene monoallyl phenyl ether, polyoxyethyl- solvent. ene diallyl phenyl ether, polyoxyethylene triallyl phenyl 45 Specific examples of the ester ether-based solvent in- ether, polyoxypropylene monoallyl phenyl ether, polyox- clude methoxybutyl acetate, methyl cellosolve acetate, yethylene-polyoxypropylene triallyl phenyl ether; polyox- ethyl cellosolve acetate, butyl cellosolve acetate, methyl yethylene monobenzyl phenyl ether, polyoxyethylene carbitol acetate, ethyl carbitol acetate, butyl carbitol ac- dibenzyl phenyl ether, polyoxyethylene tribenzyl phenyl etate and 3-methoxy-3-methyl-1-butyl acetate. Among ether, polyoxypropylene tribenzyl phenyl ether, polyox- 50 these, 3-methoxy-3-methyl-1-butyl acetate is preferable. yethylene-polyoxypropylene tribenzyl phenyl ether; poly- [0023] Although there are no particular limitations on oxyethylene monostyryl phenyl ether, polyoxyethylene the respective amounts of component (A), component distyryl phenyl ether, polyoxyethylene tristyryl phenyl (B), component (C) and component (D) in the composi- ether, polyoxypropylene tristyryl phenyl ether and poly- tion for preparing emulsion or microemulsion formula- oxyethylene-polyoxypropylene tristyryl phenyl ether.55 tions, the total amount of component (A), component (B) Among these, polyoxyethylene monoallyl phenyl ether, and component (C) is preferably 20% by weight to 50% polyoxyethylene diallyl phenylether and polyoxyethylene by weight and more preferably 25% by weight to 40% by triallyl phenyl ether are preferable. One type of the com- weight, and the amount of component (D) is preferably

4 7 EP 2 433 987 A1 8

50% by weight to 80% by weight and more preferably [Component (F)] 60% by weight to 75% by weight, based on a value of 100% by weight for the total amount of component (A), [0029] An agricultural chemical active ingredient may component (B), component (C) and component (D). be used without any particular limitations provided that 5 it is a compound used for the purpose of controlling pests. [Component E] The agricultural chemical active ingredient used is not limited by whether it is a liquid or solid, whether it is an [0024] The component (E) used as necessary in the organic compound or inorganic compound, or whether it composition for preparing emulsion or microemulsion for- is a single compound or mixture. Examples of the agri- mulations according to the present invention is a polar 10 cultural chemical active ingredient include germicides, solvent other than the ester ether-based solvent. pest control agents (such as insecticides, miticides, The component (E) is preferable in the case of using an nematicides and soil pesticides), herbicides, , agricultural chemical active ingredient (component (F)) anti-mold and anti-alga agents, plant growth regulators having low solubility with respect to the component (D). and rodent poisons. [0025] Examples of the polar solvent of the component 15 [0030] Examples of germicides include: benzimida- (E) include ketones, lactones, N- methyl-2-pyrrolidone, n- zole-based germicides such as benomyl, carbendazim, amyl acetate, propylene glycol monomethyl ether, pro- fuberidazole, thiabendazole or thiophanate methyl; di- pylene carbonate, butyl lactate ester, ethyl lactate ester, carboxyimide-based germicides such as chlozolinate, isobornyl acetate, tetrahydrofurfuryl alcohol, 3- methoxy- iprodione, procymidone or vinclozolin; DMI germicides 3-methyl-1-butanol, sulfolane and D- limonene. One type 20 such as imzalil, oxpoconazole, pefurazoate, prochloraz, of polar solvent may be used alone, or two or more types triflumizole, triforine, pyrifenox, fenarimol, nuarimol, aza- may be used in combination. conazole, bitertanol, bromconazole, cyproconazole, [0026] Among the polar solvents of the component (E), difenoconazole, diniconazole, epoxyconazole, fenbuco- ketones and lactones are preferable, and lactones are nazole, fluquinconazole, flusilazole, flutriafol, hexacona- particularly preferable, since they allow the obtaining of 25 zole, imibenconazole, ipuconazole, metconazole, my- a composition having further improved dispersibility. clobutanil, penconazole, propiconazole, prothiocona- Examples of ketones include acetone, methyl ethyl ke- zole, simeconazole, tebuconazole, tetraconazole, tri- tone, diethyl ketone, methyl isobutyl ketone, methyl-n- adimefon, triadimenol, triticonazole, etaconazole, furco- amyl ketone (2-heptanone), mesityl oxide, cyclopen- nazole-cis, ipconazole or imibenconazole; phenylamide- tanone and cyclohexanone. Examples of lactones in- 30 based germicides such as benalaxyl, furalaxyl, metal- clude γ-butyrolactone and δ-lactone. Among these, δ-lac- axyl, metalaxyl-M, oxadixyl or ofurace, amine-based ger- tone is preferable. micides such as aldimorph, dodemorph, fenpropimorph, [0027] Although there are no particular limitations on tridemorph, fenpropidine, piperalin or spiroxamine; phos- the amount of component (E) in the case of using com- phorothiolate-based germicides such as EDDP, iproben- ponent (E) in the composition for preparing emulsion or 35 fos or pyrazophos; dithiolane-based germicides such as microemulsion formulations, the total amount of compo- isoprothiolane; carboxamide-based germicides such as nent (A), component (B) and component (C) is preferably benodanil, boscalid, carboxin, fenfuran, flutolanil, 20% by weight to 50% by weight and more preferably furametpyr, mepronil, oxycarboxin, penthiopyrad or thif- 25% by weight to 40% by weight, the total amount of luzamide; hydroxy(2-amino)pyrimidines such as bupiri- component (D) and component (E) is preferably 50% by 40 mate, dimethirimol or ethirimol; AP germicides (ani- weight to 80% by weight and more preferably 60% by linopyrimidines) such as cyprodinil, mepanipyrim or py- weight to 75% by weight, and the amount of component rimethanil; N-phenylcarbamates such as diethofencarb; (E) is preferably 10% by weight to 40% by weight and and, QoI germicides (Qoinhibitors) such as azoxystrobin, more preferably 15% by weight to 30% by weight, based picoxystrobin, pyraclostrobin, kresoxim-methyl, trfloxys- on a value of 100% by weight for the total amount of45 trobin, dimoxystrobin, metominostrobin, orysastrobin, fa- component (A), component (B), component (C), compo- moxadone, fluoxastrobin, fenamidone or metominofen; nent (D) and component (E). [0031] PP germicides (phenylpyrroles) such as fenpi- [0028] In addition, the composition for preparing emul- conil or fludioxonil; quinoline-based germicides such as sion or microemulsion formulations according to the quinoxyfen; AH germicides (aromatic hydrocarbons) present invention may also contain an auxiliary compo- 50 such as biphenyl, chloroneb, dichloran, quintozene, tec- nent such as an ultraviolet absorber, an antioxidant, a nazene or tolclofos-methyl; MRI-R germicides such as preservative, an efficacy enhancer, a colorant or a fra- fthalide, pyroquilon or tricyclazole; MBI-D germicides grance within a range that does not impair the effects of such as carpropamid, diclocymet or fenoxanil; SBI the present invention. Inaddition, the composition for pre- agents such as fenhexamid, pyributicarb or ; paring emulsion or microemulsion formulations accord- 55 phenylureas such as pencycuron; Qil germicides (Qi in- ing to the present invention may also contain an agricul- hibitors) such as cyazofamid; benzamides such as zox- tural chemical active ingredient (component (F)). amide; enopyranurones such as blasticidin or mildiomy- cin; hexopyranosyls such as kasugamycin; glucopyran-

5 9 EP 2 433 987 A1 10 osyls such as streptomycin or validamycin; cyanoace- dimefluthrin, acrinathrin, cycloprothrin, halfenprox or toamides such as cymoxanil; carbamates such as flucythrinate; chitin synthesis inhibitors such as chlo- propamocarb, prothiocarb or polycarbamate; uncoupling rfluazuron, diflubenzuron, flucycloxuron, flufenoxu- agents such as binapacryl, dinocap, ferimzone or fluazi- ron, hexaflumuron, lufenuron, novaluron, tefluben- nam; organic tin compounds such as triphenyltin acetate, 5 zuron, triflumuron, bistrifluron, noviflumuron -bupro- triphenyltin chloride or triphenyltin hydroxide; phosphate fezin, diofenolan, hexythiazox, etoxazole or clofen- esters such as phosphonic acid, tolclofos-methyl or fo- tazine, ecdysone antagonists such as halofenozide, setyl; phthalamides such as tecloftalam; benzotriazines methoxyfenozide, tebufenozide, chromafenozide or such as triazoxide; benzene sulfonamides such as flu- azadirachtin; juvenile hormone-like substances sulfamide; pyridazinones such as diclomezine; CAA ger- 10 such as pyriproxyfen, methoprene or fenoxycarb; li- micides (carbonic acid amides) such as dimethomorph, pid biosynthesis inhibitors such as spirodiclofen, flumorph, benthiavalicarb, iprovalicarb or mandipropa- spiromesifen or spirotetramat; mide; tetracyclines such as oxytetracycline; thiocar- nicotine receptor agonist/antagonist compounds bamates such as methasulfocarb; and, other compounds such as acetamiprid, clothianidine, dinotefuran, im- such as etridiazole, polyoxins, oxolinic acid, hydroxyisox- 15 idacloprid, nitenpyram, thiacloprid or thiamethoxam; , octinoline, silthiofam, diflumetorim, acibenzolar- s- GABA antagonists such as acetoprole, endosulfan, methyl, probenazole, tiadinil, ethaboxam, cyflufenamid, ethiprole, fipronil, vaniliprole, pyrafluprole or pyrip- proquinazid, metrafenone, fluopicolide, cupric hydrox- role; macrocyclic lactone insecticides such as ide, organic copper, sulfur, ferbam, manzeb, maneb, me- abamectin, emamectin, milbemectin, lepimectin, tiram, propineb, thiuram, zineb, ziram, captan, captafol, 20 spinosad or ivermectin; METI I compounds such as folpet, chlorothalonil, dichlofluanid, tolylfluanid, dodine, fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad or guazatine, iminoctadine acetate, iminoctadine dodecyl- flufenerin; METI II and III compounds such as ace- benzene sulfonate, anilazine, dithianon, chloropicrin, da- quinocyl, fluacyprim or hydramethylnon; uncoupling zomet, metam sodium salt, chinomethionat, cyprofuram, agent compounds such as chlorfenapyr; oxidative silthiofam or fluoroimide. 25 phosphorylationinhibitor compounds such as cyhex- [0032] Examples of insecticides, miticides, nemati- atin, diafenthiuron, fenbutatin oxide or propargite; cides or soil pesticides, namely pest control agents, in- molting disruption compounds; mixed function oxi- clude: dase inhibitor compounds such as piperonyl butox- ide; sodium channel blocker compounds such as in- organic (thio)phosphates such as acephate, azam- 30 doxacarb or metaflumizone; microbial pesticides ethiphos, azinphos-methyl, chlorpyriphos, chlorpyri- such as BT agents, insect pathogen viral agents, in- phos-methyl, chlorfenvinphos, diazinon, dichlorvos, sect pathogen fungal agents or nematode pathogen dicrotophos, dimethoate, disulfoton, ethion, EPN, fungal agents; and other compounds such as ben- fenamiphos, fenitrothion, fenthion, isoxathion, clothiaz, bifenazate, cartap, flonicamid, pyridalyl, malathion, methamidophos, methidathion, methyl 35 pymetrozine, sulfur, thiocyclam, flubendiamide, cy- parathion, mevinphos, monocrotophos, oxydeme- enopyrafen, flupyrazofos, cyflumetofen, amid- ton-methyl, paraoxon, parathion, phenthoate, pho- oflumet, bensultap, dicofol, tetradifon, fenpyroxi- salone, phosmet, phosphamidon, phorate, phoxim, mate, amitraz, chlordimeform, triazamate, pymetro- pirimiphos-methyl,profenofos, prothiofos,sulprofos, zine, pyrimidifen, 1,3- dichloropropene, clofentezine, tetrachlorvinphos, terbufos, triazophos, trichlorfon, 40 fluacrypyrim, rotenone, DCIP, phenisobromolate, fosthiazate, phosphocarb, cadusafos, disulfoton, benzomate, methaldehyde, chlorantraniliprole spin- demeton-s-methyl, BRP, CYAP, ethoprophos, etoram or pyrifluquinazon. quinalphos, dimethylvinphos, vamidothion or pyra- clofos; carbamate-based agents such as alanycarb, [0033] Examples of herbicides include 2,4-PA, ACN, aldicarb, bendiocarb, benfuracarb, carbaryl, carbo- 45 CNP, DAP, DBN, DCBN, DCMU, DCPA, DPA, DSMA, furan, carbosulfan, fenoxycarb, fenothiocarb, methi- IPC, MBPMC, MCC, MCP, MCPB, MCPP, MDBA, PAC, ocarb, methomyl, oxamyl, pirimicarb, propoxur, thi- SAP, TCA, TCTP, ioxynil, asulam, atrazine, amiprofos- odicarb, triazamate, ethiofencarb, fenobucarb, MI- methyl, ametryn, alachlor, alloxydim, isouron, isoxaben, PC, MPMC, MTMC, pyridafenthion, furathiocarb or imazapyr, imazosulfuron, esprocarb, ethidimuron, oxa- XMC; 50 diazon, orthobencarb, karbutilate, quizalofop- ethyl, quin- pyrethroids such as allethrin, bifenthrin, cyfluthrin, clorac, glyphosate, chlormethoxynil, clomeprop, chlo- cyhalothrin, cyphenothrin, cypermethrin, alphacy- rophthalim, cyanazine, dithiopyr, siduron, cinosulfuron, permethrin, betacypermethrin, zetacypermethrin, diphenamid, simazine, dimethametryn, simetryn, dime- deltamethrin, esfenvalerate, etofenprox, fen- piperate, terbacil, dymron, thiazafluron, thifensulfuron- propathrin, fenvalerate, imiprothrin, lambdacyha- 55 methyl, tetrapion, thenylchlor, tebuthiuron, triclopyr, trif- lothrin, permethrin, prallethrin, pyrethrin I and II, res- luralin, naproanilide, napropamide, bialaphos, picloram, methrin, silafluofen, tau-fluvalinate, tefluthrin, te- bifenox, piperophos, Pyrazoxyfen, pyrazosulfuron- ethyl, tramethrin, tralomethrin, transfluthrin, profluthrin, pyrazolate, pyributicarb, phenoxaprop-ethyl, phenothiol,

6 11 EP 2 433 987 A1 12 phenmedipham, butachlor, butamifos, flazasulfuron, flu- [0037] Although the composition for preparing emul- azifop, pretilachlor, prodiamine, propyzamide, bromacil, sion or microemulsion formulations according to the prometryn, bromobutide, hexazinone, bethrodine, ben- present invention is normally a composition that does not sulfuron-methyl, benzofenap, bentazone, benthiocarb, contain water, water may be contained as necessary. pendimethalin, fosamine ammonium, methyl daimuron, 5 Although there are no particular limitations on the amount metsulfuron-methyl, metolachlor, metribuzin, mefenac- of water, an amount of water may be contained that di- et, molinate, linuron or lenacil. lutes a composition not containing water by 1.2 to 10 [0034] Examples of antifungal, anti- mold and anti-alga times. agents include tris-nitromethane, chlorobutanol, bronop- [0038] Preparation of the composition for preparing ol, glutaraldehyde, formaldehyde, α-bromocinnam alde- 10 emulsion or microemulsion formulations according to the hyde, 2-n-octyl-4-isothiazolin-3-one, 5-chloro-2-methyl- present invention may be carried out according to a 4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, 1,2- known composition preparation method. For example, benzisothiazolin-3-one (BIT), 2-n-butyl-1,2-benzisothia- the composition may be prepared by mixing prescribed zolin-3-one, allyl isothiocyanate, thiabendazole, methyl amounts of component (A), component (B), component 2-benzimidazolylcarbamate, lauricidin, bioban, triclocar- 15 (C), component (D) and, as necessary, component (E) ban, halocarban, glassySiCAL, benzoic acid, sorbic acid, followed by stirring. At that time, the order in which each caprylic acid, propionic acid, 10-, potas- component is added and mixed is arbitrary. A composi- sium sorbate, potassium benzoate, monomagnesium tion for preparing emulsion or microemulsion formula- phthalate, 8-hydroxyquinoline, TMTD, triclosan, dichlo- tions obtained in such a manner is a composition that helanilide, trifluanid, milt protein, egg white lysozyme, 20 does not contain water, and can be stored, stocked or benthiazole, carbam sodium, triazine, tebuconazole, hi- transported as is. Emulsion or microemulsion formula- nokitiol, tetrachloroisophthalonitrile, 1,2-dibromo-2,4-di- tions can also be obtained by adding a prescribed amount cyanobutane, chlorhexidine gluconate, polyhexamethyl- of water and, as necessary, component (F) to the com- ene biguanide, polyhexamethylene guanide, dantobrom, position for preparing emulsion or microemulsion formu- glydant, sodium pyrithion, zinc pyrithion, thymol, isopro- 25 lations not containing water. pyl methyl phenol, phenylphenol, o- phenol, butylpa- [0039] In addition, preparation of a composition for pre- raben, , methylparaben, propylparaben, paring emulsion or microemulsion formulations contain- meta-cresol, ortho-cresol, para-cresol, sodium ortho- ing water may be carried out by, for example, mixing pre- phenylphenol, chlorophene, parachlorphenol, parachlo- scribed amounts of component (A), component (B), com- romethaxylate, parachlorocresol, fluorofolpet, polyly-30 ponent (C), component (D), water, and as necessary, sine, diiodomethyl para-tolyl sulfone, polyvinylpyrro- component (E) followed by stirring. At that time, the order lidone parachloroisocyanel, benzalkonium chloride, di- in which each component is added and mixed is arbitrary. decyldimethyl ammonium chloride, benzethonium chlo- Although there are no particular limitations on the amount ride, cetyl ammonium bromide, cetrimide, CTAB, cetav- of water, the amount of water may be that, for example, lon, benzalkonium chloride, cetyl pyridinium chloride,35 which dilutes the composition not containing water by 1.2 DCMU, IPBC and TCMSP. to 10 times. The composition containing water can be [0035] Examples of plant growth regulators include ab- stored, stocked or transported as is. Although the com- scisic acid, indole butyric acid, , ethychloz- position containing water may be used as is as an emul- ate, ethephon, cloxyfonac, chlormequat, chlorella ex- sion or microemulsion formulation, a prescribed amount tract, calcium peroxide, cyanamide, dichlorprop, gib-40 of component (F) and, as necessary, additional water berellin, daminozide, decyl alcohol, trinexapac-ethyl, can be added to the composition for preparing emulsion mepiquat-chloride, paclobutrazol, paraffin, wax, pipero- or microemulsion formulations containing water in antic- nyl butoxide, pyraflufen ethyl, flurprimidol, prohydrojas- ipation of high agricultural chemical efficacy. mon, prohexadione-calcium, benzylaminopurine, [0040] Moreover, preparation of a composition for pre- pendimethalin, forchlorfenuron, potassium hydrazide45 paring emulsion or microemulsion formulations contain- maleate, 1-naphthylacetoamide, 4- CPA, MCPB, choline, ing anagricultural chemical active ingredient (component oxyquinoline sulfate, ethychlozate, butralin, 1-methylcy- (F)) may be carried out by, for example, mixing compo- clopropene and aviglycine hydrochloride. nent (A), component (B), component (C), component (D), Examples of rodent poisons include coumarin- based ro- and as necessary, component (E) and/or water followed dent poisons and chlorophacinone. 50 by stirring to obtain a composition, and then adding com- [0036] Although there are no particular limitations on ponent (F) to the composition followed by stirring. In ad- the amount of the agricultural chemical active ingredient dition, this may also be carried out by mixing prescribed (F), the component (F) may be preferably contained at 1 amounts of component (A), component (B), component part by weight to 43 parts by weight and more preferably (C), component (D), component (F), and as necessary, at 3 parts by weight to 25 parts by weight based on 100 55 component (E) and/or water followed by stirring. At that parts by weight of the total amount of component (A), time, the order in which each component is added and component (B), component (C), component (D) and com- mixed is arbitrary. A composition for preparing emulsion ponent (E). or microemulsion formulations that contains an agricul-

7 13 EP 2 433 987 A1 14 tural chemical active ingredient (component (F)) ob- solution followed by dissolving by stirring. 20.0 parts by tained in such a manner can be stored, stocked or trans- weight of a 50% aqueous solution of didecyl-dimethyl ported as is. Although the composition containing water ammonium chloride (DDAC) (Sanyo Chemical Indus- can also be used as is as an emulsion or microemulsion tries) and 22.8 parts by weight of ion exchange water formulation containing component (F), it can also be di- 5 were gradually added thereto followed by stirring to ob- luted by further adding water as necessary. tain a composition for preparing a microemulsion formu- lation. EXAMPLES The composition was then diluted 100- fold with water to obtain a microemulsion formulation. [0041] The following provides a more detailed expla- 10 nation of the present invention by indicating examples (Example 3) thereof. However, the present invention is not limited by the examples. [0046] 32.9 parts by weight of 3-methoxy-3-methyl-1- butyl acetate (Solfit AC, Kuraray), 6.0 parts by weight of (Example 1) 15 polyoxyethylene ally phenyl ether (Newkalgen CP- 15-200, Takemoto Oil & Fat), 6.0 parts by weight of poly- [0042] 28.7 parts by weight of 3-methoxy-3-methyl-1- oxyethylene sorbitan monooleate (Newkalgen D-945, butyl acetate (Solfit AC, Kuraray) were placed in a con- Takemoto Oil & Fat), 3.0 parts by weight of sodium dioctyl tainer equipped with a stirrer followed by the addition of sulfosuccinate (Newkalgen EP-4C, Takemoto Oil& Fat) 5.0 parts by weight of polyoxyethylene allyl phenyl ether 20 and 2.1 parts by weight of n-butyl-BIT (Arch Chemicals (Newkalgen CP-15-200, Takemoto Oil & Fat), 5.0 parts Japan) were charged into a container equipped with a by weight of polyoxyethylene sorbitan monooleate stirrer followed by dissolving by stirring. The mixture was (Newkalgen D-945, Takemoto Oil & Fat), and 5. 0 parts suitably heated to promote dissolution. by weight of sodium dioctyl sulfosuccinate (Newkalgen The Newkalgen CP-15-200, Newkalgen D-945 and EP-4C, Takemoto Oil & Fat) and dissolving by stirring. 25 Newkalgen EP-4C were heated prior to use to remove The mixture was suitably heated to promote dissolution. any residual organic solvents and water. The Newkalgen CP-15-200, Newkalgen D-945 and [0047] 50.0 parts by weight ofion exchange water were Newkalgen EP-4C were heated prior to use to remove gradually added thereto followed by stirring to obtain a any residual organic solvents and water. composition for preparing a microemulsion formulation. [0043] 2.1 parts by weight of acetamiprid (Nippon So- 30 The composition was then diluted 100- fold with water to da), 2.1 parts by weight of propiconazole (Janssen Phar- obtain a microemulsion formulation. maceutical) and 2.1 parts by weight of cyproconazole [0048] The compositions for preparing a microemul- (Janssen Pharmaceutical) were added to the resulting sion formulation and the microemulsion formulations ob- solution followed by dissolving by stirring. 50.0 parts by tained in Examples 1 to 3 were allowed to stand at a weight of ion exchange water were gradually added35 temperature range of 0°C to 40°C. The emulsions were thereto followed by stirring to obtain a composition for maintained in a stable state even after the passage of preparing a microemulsion formulation. one week. The composition was then diluted 100- fold with water to obtain a microemulsion formulation. INDUSTRIAL APPLICABILITY 40 (Example 2) [0049] The composition for preparing emulsion or mi- croemulsion formulations according to the present inven- [0044] 30.0 parts by weight of 3-methoxy-3-methyl-1- tion is able to provide emulsion or microemulsion formu- butyl acetate (Solfit AC, Kuraray) and 10.0 parts by lations that demonstrate favorable dilution properties weight of γ-butyrolactone were placed in a container 45 without being affected by the solubilities of constituent equipped with a stirrer followed by the addition of 6.5 components. The composition for preparing emulsion or parts by weight of polyoxyethylene allyl phenyl ether microemulsion formulations according to the present in- (Newkalgen CP-15-200, Takemoto Oil & Fat), 6.5 parts vention facilitates handling during preparation since it by weight of polyoxyethylene sorbitan monooleate demonstrates little foaming. Moreover, the composition (Newkalgen D-945, Takemoto Oil & Fat), and 2.0 parts 50 for preparing emulsion or microemulsion formulations ac- by weight of sodium dioctyl sulfosuccinate (Newkalgen cording to the present invention enables the emulsion or EP-4C, Takemoto Oil & Fat) and dissolving by stirring. microemulsion formulation to be maintained in a stable The mixture was suitably heated to promote dissolution. state even if diluted with water. The Newkalgen CP-15-200, Newkalgen D-945 and Newkalgen EP-4C were heated prior to use to remove 55 any residual organic solvents and water. Claims [0045] 2.1 parts by weight of acetamiprid and 2.1 parts by weight of cyproconazole were added to the resulting 1. A composition for preparing emulsion or microemul-

8 15 EP 2 433 987 A1 16

sion formulations, comprising: 8. An emulsion or microemulsion formulation, compris- ing: the composition for preparing emulsion or mi- a component (A): a polyoxyalkylene allyl phenyl croemulsion formulations according to any one of ether, a polyoxyalkylene aralkyl phenyl ether or claims 1 to 7. a polyoxyalkylene aralkenyl phenyl ether, 5 a component (B): a polyoxyalkylene sorbitan 9. An emulsion or microemulsion formulation obtained alkylate, by diluting with water the composition for preparing a component (C): a dialkylsulfosuccinate, and emulsion or microemulsion formulations according a component (D): an ester ether- based solvent. to any one of claims 1 to 7. 10 2. The composition for preparing emulsion or microe- 10. The emulsion or microemulsion formulation accord- mulsion formulations according to claim 1, wherein ing to claim 8 or 9, which is used to preserve wood. a ratio of a total amount of the component (A) and the component (B) to an amount of the component (C) is within a range of 1:2 to 1:7, and 15 a ratio of an amount of the component (A) to an amount of the component (B) is within a range of 2: 1 to 1:2.

3. The composition for preparing emulsion or microe- 20 mulsion formulations according to claim 1 or 2, wherein a total amount of the component (A), the component (B) and the component (C) is 20% by weight to 50% by weight and an amount of the com- ponent (D) is 50% by weight to 80% by weight, based 25 on a value of 100% by weight for a total amount of the component (A), the component (B), the compo- nent (C) and the component (D).

4. The composition for preparing emulsion or microe- 30 mulsion formulations according to claim 1 or 2, fur- ther comprising a component (E) : a polar solvent other than the ester ether-based solvent.

5. The composition for preparing emulsion or microe- 35 mulsion formulations according to claim 4, wherein a total amount of the component (A), the component (B) and the component (C) is 20% by weight to 50% by weight, a total amount of the component (D) and the component (E) is 50% by weight to 80% by40 weight, and an amount of the component (E) is 10% by weight to 40% by weight, based on a value of 100% by weight for a total amount of component (A), component (B), component (C), component (D) and component (E). 45

6. The composition for preparing emulsion or microe- mulsion formulations according to any one of claims 1 to 5, further comprising a component (F): an agri- cultural chemical active ingredient. 50

7. The composition for preparing emulsion or microe- mulsion formulations according to claim 6, compris- ing 1 to 43 parts by weight of the component (F) based on 100 parts by weight of a total amount of 55 component (A), component (B), component (C), component (D) and component (E).

9 EP 2 433 987 A1

10 EP 2 433 987 A1

11 EP 2 433 987 A1

REFERENCES CITED IN THE DESCRIPTION

This list of references cited by the applicant is for the reader’s convenience only. It does not form part of the European patent document. Even though great care has been taken in compiling the references, errors or omissions cannot be excluded and the EPO disclaims all liability in this regard.

Patent documents cited in the description

• JP 2009121611 A [0001] • JP 2006509807 PCT [0009] • JP 2007015959 A [0009] • JP 2002194205 A [0009] • JP 2006199687 A [0009] • JP 2008308508 A [0009]

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