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TMNT 'US 2009010507381 cu») United States 2 Patent Application Publication co) Pub. No.: US 2009/0105073 Al Taranta et al. (43) Pub. Date Apr. 23, 2009 oy FORMULATIONS G0) Foreign Application Priority Data (75) Inventors: Claude Taranta, Stutensee (DE); Mar.24,2006 (EP) 061116729 Arnold Kraushaar, Speyer (DE) Matthias Bratz, Maxdoc! (DE) ication Classification St) Inch Comespondence Address ¢ BRINKS, HOFER, GILSON & LIONE ALN 25/700 2006.01) P.O. BOX 1340. AMIN 47284 (2006.01), MORRISVILLE, NC 27560 (US) arr 7700 (2006.01) (3) Assignee: BASF SE, Ludwigshafen (DE) oe ee ee (21) Appl. No. 1293.83 ABSTRACT (22) PCT Fited rpc The pent ion ete fo nonaquns ychemil (86) PCT Ne. PCTEP2007/052651 (@) a least one pesticide () at least one organic solvent; and $371 (o\l), (¢) mixture comprising a non-ionic distyeylpienol alkoxy’ (2),(4) Date: Sep. 22, 2008, Tate and a ionic distyrylphenol alkoxylate US 2009/0105073 AI AGROCHEMICAL FORMULATIONS, 10001} ‘The preset invention relates t non-aqueous agro- ‘chemical formulations comprising 0002] (a) at least one pesticide; [0003] (b) atleast one organi solvent and 10004) _(c) a surfactant comprising a mixture comprising 2 ‘non-ionic distyeyiphenol alkoxylate and a ionic dlistyryphenol alkoxylate. 10005] It fuer relates to a method for preparation of & Tiguid noa-agucous agrochemical formulation comprising ‘contacting atleast one pesticide, a organic solvent and an, ‘emulsifier comprising a mixture of distyrylphenol alkoxylate and sulfated distyrylphenol alkoxylate, 10006] Moreover it relates to a use of an emulsifier com- Prising « mixture comprising noa-ionic distyrylphenol alkoxylate and inte distyrypheno! alkoxylate) for edue- tion of eye toxicity in agrochemical formulations comprising atleast one organic solvent and b) for enhancement of efi ‘ieney of pesticides in agrochemical formulation comprising at least one organic solvent 10007} Another aspect ofthe invention covers a method of ‘combating harmfol insects and/or phytopathogenic fungi and a method of controlling undesired vegetation, 10008] This invention also relates to seeds tested with said {oration 10009] Combinations of prefered embodiments with other preferred embodiments are within the scope ofthe present invention, [0010] U.S. Pat, No, 5,082,591 discloses non-ionic poly- alkoxylated poly(I-phenylethyl)phenols for use as surface sctive agents [W011] "EP 0055401 discloses inseetcide compositions Sontag no-one pals poly(-phes ety phenols [0012] WO 9601087 (also published as DE 69515663) discloses emulsifiable concentrates comprising a pesticide, an ester a solvent, a dodecyl henzosulfontate and a non-ionic surfactant, [0013] EP 0391171 discloses the synthesis and use of slstyyl phenyl-tris-glykol ether as crystallisation inhibitor in ‘an aqueous fingicidal spray. 10014) "US. Pat, No. 2,993,830 discloses non-ionic poly- alkoxylate poly(1-phenylethyjphenols in mixture with sul qonated phenylalkyethers, The later compounds have a sul- onic aid geoup bound fo the aromatic ing and contain no polyalkoxy groups. [0015] W02001/20986 discloses polystyryphenol ethoxy Tate phosphate in mixture with alkoxylatedlignosulfonate salts. la an embodiment further co-surfactaats may be present, for example tistyrylphenol ethoxylate, One example discloses a mixture of tistyryipheno] ethoxylate phosphate with alkoxylated Fgnosulfonate salt and tristyry1 phenol cethoxslte [0016] WO 20061030006 discloses aqueous microemol- sions comprising polyarylpheno] polyalkoxyether sulfates or phosphates. As optional emulsifiers ethoxylated castor oils ‘re meationed, [0017] WO 2001/70024 discloses processes for proparing ‘aqueous formlatons of hydraphobe pesticides. In example Ta mixture of an ethoxylated disiyrylphenol andl an ethoxy te distyryphenol sulfate are mixed with aromatic solvent ‘and water to prepare an emulsion. A general auidelineis give hydrophobic pesticide and one or more emulsifiers. [0018] One of the tasks the formulation chemist i faced ‘With the development of formulations, which improve the efficiency of pesticides within these formulations. [0019] Furthermore, ia formulation development, the use ‘of onzanie solvents often plays a role, sine some pesticide formulations may require the use of organic solvents to enablethe processing of pesticides. A problem encountered in the development of such liguid non agucous agrochenieal formulation is that the orgie solvents used in sai forma- lation often exhibit significant imitation vo eye and are there- fore classified ss eye iitant. This may lead to registration problems. [0020] ‘The object of the present invention is therefore t0 provide # non-agueous formulation that [0021] shows improved efficiency ofthe pesticide used [0022] _) shows reduction of eye ietation andlor [0023] ©) shows chemical and physical stability [0024] A further object of the invention is to provide @ ‘non-aqueous formulation that shows above mentioned char acteristics for mixtures of at least wo pesticides, whereinone pesticide has significantly beter solubility in waterthanone Of the other pesticides present in the mixtire, such as, fo «example, a mixture of alphareypermetin and acetamiprid [0028] "The object was solved by liguid non-aqueous for- ‘ulations comprising 10026) (a)at east one pesticide; [0027] (atleast one onzanie solvent and (0028) (©) a surfactant comprising mixture comprising @ non-ionic distyryiphenol alkoxylate anda ionic distyeyiphenol alkoxylate [0029] _‘Theterm* surfactant deseribes.a compound, which can have the properties of emulsifying, dispersing or weting agent or awvant 10030] In a preferred embodiment, the non-ionie éstyryiphenol alkoxylate are those of formu f Ys poten wherein a is 2, and ‘mis Lo 40, more preferably $ to 25, and most preferably 13 w16, AO is FO, PO ora mixture of FO and PO moieties, preferably EO, [0031] Te terns “FO” and “PO” as used herein have the Tollowing meaning: “EO” is —CH,—CH,—O— and “PO” is —CH(CH,)— CHO The term *A0™ means “alkoxylate” and is PO or a mixture of EO and PO moiety, preferably HO, Included herein ae statistical as well as alternating and block sequences of BO and PO, 0032] More preferred non-ionic distyryiphenol alkoxy Jates are those of formula Ia US 2009/0105073 AI os OS wherein (is 1 to 40, preferably $ 1925, more preferably 10t020, most preferably 131016, 10033] "Ina prefered embodiment, the oni dstyrylphenal alkoxylates are these of formula It wherein nis 2, and tis 110-40, more preferably Sto 28, and most preferably 13 16, AO is EO, PO ora mixtureof EO and PO moieties, preferably FO; and Ris SO,H, H,PO,, SO,X or HPO,Y 10034] "Therespectvefreeacidformean bealso neutralized ‘witha base, e,analkali metallhydroxide (eg. NaOH, KOH) ‘or ammonia or an amine (eg. of form II wherein R’, R? and R? are independently from each other hydrogen, meth, ethyl or propyl preferably R', R® and R™ ate ethy), in aqueous solution resulting in R—SO,X or HPO.Y (wherein X and represent independently from each ‘other NH," (NHR'R'R?)" with R', RE and R° as defined above, Nav or K 0035} Ris especially preferred SO.NH, 10036] _ More prefered ionic distyryphenol alkoxylates are those of formula Ha a Apr. 23, 2009 pis | 1040, proferably $1025, more preferably 100 20, most preferably 1310 16; and Rs SO,H, HPO, SO,X or HPOY. Te respective five acid form ca be also neutralized with 3 base, eg. an alkali metall hydroxide (eg. NaOH, KOH) or ammonia or an amine (eof forma IL wherein R', R? and R are independently from each other hydrogen, methyl ethyl or propyl, preferably R', R? and R™ fare ethyl), in aqueous soliton resulting in R=SO,X or HPO,Y (Wherein X andY represent independently from each other NEL, (NHR'RER?)* with R', RY and RY as defined above, Na of K"), [0037] Ris especially prefered SO,NH, [038] ‘Tae preparaton of compounds of formula land lais known in thear (soe eg. U'S. Pa. No. 5,082,591). Prepar- tion of compounds of formula I ean be performed easily by methods known by the skilled artisan, eg: phosphatation (e.& ‘with?,O. jorsulfatation g, wih Z,NSO,H) of eompounds of femula I or Ia 0039} Compounds of formula T andor IL ate also for jnstance available in commercial products, for example Soprophor® DSS 15 (Rhos; ammonium sal of ethoxylated polvarylphenol sulfate, CASNo, 59891-11-1 (corresponds to Poiyfoxg-12-ethanediyl), alpha.-sulfo-omega-{bisI-phe- nylethy?)phenoxy]-, ammonium sal), with a specific gravity of L15 gL) of Agrlani® AEC 145 (nonionic polyaryl cethoxylate with 100% ative content, AKZO Nobel} [0040] According to this invention compound e) isa mix- ture comprising a non-ionie distyrylpaenol alkoxylate and a jonic distyryiphenol alkoxylate, The ratio of ion distyeyplienol alkoxylate to nonionic distyryiphenolalkoxy- Jate can vary in broad ranges, preferably inranges from 90/10 {0 2080 by weight. [0041] Suck compounds €) are for instance commercially available, In general such commercial produets comprise ‘non-ionic and ionic distyrylpheoolalkoxylates, wherein the ‘non-ionie distyrylphenol alkoxylate canbe found in a range from 10 to 50 wi % based on the total produc. [0042] ‘The organic solvent (b) sa polar oF non-polar sol- vent or a mixture of @ polar and a non-polar solvent, oe @ rixture of polar solvents, preferably a polar solvent oF @ mixture of polar solvents [0043] Examples of non-polar solvents are C8 to C1 aro~ ‘matic pelroleum derivatives (aromatic hydrocarbons) with a solubility in water at room temperature of <0.1% (wh) anda Gtillaion range from 130° C. to 300° C. (commercially vailable from FxonMobil or BP under the following brand ames: SolvessoR 100, Solvesso® 150, Solvessor® 200, Solvesso 150ND, Solvesso-® 20ND, Aromatic 150, Aro- ‘matic B 200, Hydrosol® A200, Hydrol A230/270,Caro- ‘max 20, Caromax® 28, Aromat® K 150, Aromat K 200, Shellso1® A 150, Shellsol® A 100, Fiat FAS-TX 150, Fin® AS-IX 200), vegetable ois such s coco oil palm kero} palm ol, soya oil, rapeseed ol, corm oil and the methyl oF thy esters of theaore-mentioned ils, hytracarbons sich as ‘aromatic depleted, linear parafinc,isoparaffinic eyelopa affinic having a lah point between 40° C. and 250" Cand a

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