NZ613701B2 - Composition comprising a pesticide, a surfactant and an alkoxylate of 2-propylheptylamine - Google Patents

Abstract

Disclosed is a composition comprising a pesticide, a surfactant, and an alkoxylate, wherein the alkoxylate is an amine alkoxylate (A) or a quaternized derivative (AQ) of the amine alkoxylate (A), wherein the variables are as defined in the specification. Disclosed is a process for preparing the composition by bringing into contact the concentrate and a pesticide; or by bringing into contact the pesticide, the surfactant and the alkoxylate; and to the use of the surfactant by addition to a mixture comprising the pesticide and the alkoxylate. Disclosed is a method of controlling phytopathogenic fungi and/or undesired vegetation and/or undesired insect or mite attack and/or for regulating the growth of plants, wherein the composition is allowed to act on the respective pests, their environment or the plants to be protected from the respective pest, on the soil and/or on undesirable plants and/or the crop plants and/or their environment. Furthermore, seed comprising the composition is disclosed. osition by bringing into contact the concentrate and a pesticide; or by bringing into contact the pesticide, the surfactant and the alkoxylate; and to the use of the surfactant by addition to a mixture comprising the pesticide and the alkoxylate. Disclosed is a method of controlling phytopathogenic fungi and/or undesired vegetation and/or undesired insect or mite attack and/or for regulating the growth of plants, wherein the composition is allowed to act on the respective pests, their environment or the plants to be protected from the respective pest, on the soil and/or on undesirable plants and/or the crop plants and/or their environment. Furthermore, seed comprising the composition is disclosed.

Description

Composition comprising a pesticide, a surfactant and an alkoxylate of 2—propylheptyl— amine The present invention relates to a composition sing a ide, a surfactant and an alkoxylate. Moreover, the invention relates to a concentrate comprising the tant and the alkoxylate; and to a process for preparing the composition by bringing into contact the concentrate and a pesticide; or by bringing into contact the pesticide, the surfactant and the alkoxylate; and to a use of the surfactant for adding to a mixture comprising the pesticide and the alkoxylate. The invention furthermore 1O relates to a method of controlling phytopathogenic fungi and/or undesired vegetation and/or undesired insect or mite attack and/or for regulating the growth of plants, wherein the composition is allowed to act on the respective pests, their environment or the plants to be protected from the respective pest, on the soil and/or on undesirable plants and/or the crop plants and/or their environment. Furthermore, the ion relates to seed comprising the composition. The present invention ses combinations of preferred es with other preferred features.

Agrochemical formulations comprising amine lates are generally known: 2O discloses a herbicidal composition comprising a phenoxy—acid herbicide and an alkoxylated alkylamine as adjuvant, it being le for the alkylamine, for example, to be a 2—propylheptylmethylamine which is alkoxylated with 3 to 20 ethylene oxide groups.

US 5,668,085 discloses a herbicidal ition sing an aqueous solution of glyphosate and surfactant. The surfactant may be an alkoxylated alkylamine, the alkyl group sing 8 to 22 carbon atoms. discloses ylheptylamine alkoxylates, their preparation, and emical formulations comprising ide and the 2—propylheptylamine alkoxylates.

US20100317521 and U820110039703 disclose a formulation comprising glyphosate and, by way of surfactant, an alkoxylate of a branched alkyl amine.

Alkoxylated alkylamines, in particular commercially ble ethoxylated tallow fatty amines (POEA), have important toxic properties (such as irritation of the skin and the eyes) and ecotoxic properties (such as high ecotoxicity to aquatic organisms such as algae and daphnias). Thus, for example, POEA (CAS No. 61791—26—2), which is 40 frequently present in Roundup® herbicides as a wetter, is considered to be relatively toxic to aquatic organisms (Tsui and Chu, Chemosphere 2003, 52, 1189—1197).

It was therefore an object of the present invention to find an adjuvant which is well suited to pesticides, in particular herbicides such as glyphosate while being less toxic ially lower toxicity to aquatic organisms). Furthermore, the adjuvant should make possible a storage-stable ation of the pesticides. Another object was to increase the biological activity of the agrochemical composition. Finally, this nt was to avoid phytotoxic side-effects. The above objects, and any further objects, are to be read disjunctively with the object of at least providing a useful alternative.

The object was solved by a composition comprising a pesticide, a surfactant and an late, wherein the alkoxylate is an amine alkoxylate (A) R1 O R6 N n (A), R7 R2 O R6 or a quaternized derivative (AQ) R1 O R6 +N n A- (AQ) R7 R2 O R6 of the amine alkoxylate (A), where R1, R2, and R5 independently of one r are ethylene, propylene, butylene or a mixture of these, R3 is an H, -OH, -OR4, -[R5-O]p-R6, C1-C6-alkyl or an oxygen anion, R4 is a C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, R6 is an H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, -SO3Ra, -P(O)ORbORc, 2Rd, or -C(O)Re, R7 is a C6-C14-alkyl, Ra and Rd independently of one another are an H, nic or organic cations, Rb and Rc independently of one another are an H, inorganic or organic cations, C1-C6- alkyl, C2-C6-alkenyl or C2-C6-alkynyl, Re is C1-C22-alkyl, C2-C22-alkenyl, C2-C22-alkynyl, C6-C22-aryl or -alkylaryl, n, m and p independently of one another have a value of from 1 to 30, A- is an lturally acceptable anion, or, if R3 is an oxygen anion, A- is absent.

Preferably, the composition according to the invention comprises a pesticide and an alkoxylate, wherein the alkoxylate is an amine late (A).

Preferably, n has a value of from 1 to 20, especially preferably from 1 to 15. Preferably, m has a value of from 1 to 20, especially preferably from 1 to 15. Preferably, p has a value of from 1 to 30, especially preferably from 1 to 20. The values of n, m and o are normally average values as they mostly arise upon the alkoxylation with alkoxides.

Therefore, n, m and o can not only be integers, but also all values n the integers.

PF 71968 W0 2012/116939 3 Preferably, in the case of the amine alkoxylate (A), the total of n and m is 2 to 40 and in its quaternized derivative (AQ) the total of n, m and p is 3 to 80. In the case of the amine alkoxylate (A) the total of n and m is especially preferably 3 to 30, specifically preferably 5 to 18, and specifically 8 to 14.

In a further especially preferred embodiment, the total of n and m is 6 to 9, in particular 6.5 to 8.5 and in particular 6.9 to 7.9. In a further ally preferred embodiment, the total of n and m is 11 to 40, in particular 12 to 30 and in ular 13.5 to 25. In a r especially preferred ment, the sum of n and m is 8 to 13, in particular 9 1O to 11.

In the case of the nized derivative (AQ) of the amine alkoxylate (A), the total of n, m and p is especially preferably 3 to 40 and specifically 5 to 25. In one especially preferred embodiment, the sum of n and m is 8 to 13, in particular 9 to 11.

R1, R2 and R5 are preferably independently of one r ethylene, ethylene and propylene, ethylene and butylene, or ethylene, propylene and butylene. In a further preferred embodiment, R1, R2 and R5 are propylene. In a further preferred embodiment, R1, R2 and R5 are butylene. Especially preferably R1, R2 and R5 independently of one 2O another are ne, or ethylene and propylene. Very especially preferably, R1, R2 and R5 are ethylene.

If R1, R2 or R5 comprise a butylene radical, the latter may be present as a n—butylene, an isobutylene or a 2,3—butylene group, with n—butylene and isobutylene being red and n—butylene being most preferred.

R1, R2 and R5 independently of one another may be a mixture of ethylene, propylene or butylene. In this context, for example one or all radicals R1, R2 and R5 may comprise a mixture of these groups in each alkoxylate chain. Such mixtures can be linked to one 3O another in any desired order, for example ly or ise (such as one block ethylene and one block propylene). Also, it is possible for in each case one or more of the radicals R1, R2, and R5 to form a complete alkoxylate chain composed of different alkylene groups. For e, R1 and R2 may be composed of ethylene and R5 of ene.

R3 is preferably an H, -OH, C1-C4-alkyl or an oxygen anion, it is especially preferably an H, methyl, butyl or an oxygen anion. In a specifically preferred embodiment, R3 is a methyl. In a further specifically red embodiment, R3 is an oxygen anion. In a further specifically preferred embodiment, R3 is an H.

R4 is preferably a C1—Ce—alkyl, in particular a methyl or butyl, especially butyl.

PF 71968 W0 16939 4 2012/053230 R6 is preferably an H or C1—C6—alkyl, more preferably an H or , especially H.

R7 can be a linear or branched, saturated or unsaturated Cs-C14-alkyl l, such as hexyl, heptyl, octyl, nonyl, decyl, l, dodecyl, tridecyl or tetradecyl. R7 is preferably a branched, saturated alkyl radical. R7 is preferably a Cg—C13—alkyl radical. R7 is especially preferably a branched alkyl radical C9H19, a branched 013H27—alkyl radical, 2—propylheptyl or 2—ethylhexyl. In a r especially preferred form, R7 is especially ably a branched alkyl radical C9H19, 2—propylheptyl or 2—ethylhexyl. In particular, R7 is 2—propylheptyl. In one embodiment, R7 is one of the abovementioned radicals, 1O with the exception In a preferred embodiment, R7 is 2—ethylhexyl.

In a further preferred embodiment, R7 is a branched alkyl radical C9H19. Examples are, inter alia, 2—methyl—1—octanol, 2—ethyl—1—heptanol, 2—propyl—1—hexanol, yl—4— ymethyl—heptane, 3—methyl—3—hydroxymethyl—heptane or 2—hydroxymethyl—3— methyl—heptane. Preferably, the branched alkyl radical C9H19 comprises several different, branched alkyl radicals C9H19. The mean degree of branching is in this case 1.01 to 2.5, preferably 1.05 to 1.8, especially preferably 1.1 to 1.5, very especially 2O preferably 1.2 to 1.3. The term “degree of branching” is here defined as known in principle, as the number of methyl groups in one alcohol molecule minus 1. The mean degree of branching is the statistic mean of the degrees of branching of all molecules of a sample. The preparation of these compounds is known, for example from US 600.

In a further preferred embodiment, R7 is a branched alkyl radical C13H27. An example is an isotridecyl radical.

In an especially preferred embodiment, R7 is 2—propylheptyl. In this case, the late corresponds to the amine alkoxylate (A1) A/QVN/I/R—O%n—R (A1) \[\R2 /\/:j\/+'l‘/[/R—O—]n—RR3 1 6 A' (A01)- \I\RZ 0{FR6 PF 71968 W0 2012/116939 5 Ra and Rd are independently of one another H, or inorganic or organic cations, which may be singly or ly positively charged. Examples of inorganic cations are cations of ammonium, Na+, K+, Mg2+, Ca2+, or Zn2+. Examples of organic cations are methyl— ammonium, dimethylammonium, trimethylammonium, tetramethylammonium, (2-hydroxyethyl)ammonium, bis(2—hydroxyethyl)ammonium, -hydroxyethyl)— ammonium, tetra(2—hydroxyethyl)ammonium. Preferably, Ra and Rd independently of one r are H or inorganic cations. If an inorganic or organic cation is present, then the associated anionic group would be formed by the corresponding functional group (e.g., -SOs', -P(O)O-O-, or -CH2002‘) on R6.

Rb and Rc are preferably, independently of one another, H, inorganic or organic cations.

Suitable inorganic or organic cations are those specified under Ra.

In another embodiment, in the quaternary derivative (AQ), the radicals Ra, Rb, Rc and Rd independently of one another may be organic cations, with the cationic group being the quaternary nitrogen cation of A0 itself. It would also be possible, therefore, for A0 to form a rion, with the anionic group being formed by the corresponding functional group (e.g., -SOg', —P(O)O-O-, or —CH2002‘) on R6 in AQ, and the cationic group by the quaternary nitrogen of A0. In this zwitterionic form of AQ, the presence of 2O an agriculturally acceptable anion A- is optional.

Re is preferably C1—C12—alkyl, C6—C12—aryl, or Cy—C12—alkylaryl, more ably C1—Ce— alkyl.

A- is an agriculturally acceptable anion, as they are generally known to the skilled worker. Preferably, A- is a halide (such as chloride or bromide), phosphate, sulfate or an anionic ide. Especially preferably, A- is an anionic ide, such as a glyphosate anion or glufosinate anion. If R3 is an oxygen anion, an amine oxide is present. In this case, a further anion such as A- is absent.

In a preferred ment R1 and R2 independently of one another are ethylene, ethylene and propylene, ethylene and butylene, or ethylene, propylene and butylene, and the total of n and m is 2 to 60, ably 2 to 40, especially preferably 3 to 30 and in particular 5 to 25. In a very particularly preferred embodiment, R1 and R2 are ethylene, ethylene and propylene, ne and butylene, or ethylene, propylene and butylene and the total of n and m is 5 to 18, more particularly 8 to 12, and ally 9 to 11.

In a further red embodiment, R1 and R2 ndently of one another are both ethylene and propylene, and the total of n and m is 2 to 60, preferably 3 to 30, 40 especially preferably 5 to 20 and in particular 8 to 14. ably the alkoxylate comprises 1.5 to 8 mol (preferably 2 to 6 mol) of propylene oxide and 5 to 20 mol rably 7 to 13 mol) of ethylene oxide.

PF 71968 W0 2012/116939 6 In a particularly preferred embodiment R1 and R2 are ethylene, and the total of n and m is 2 to 60, ably 2 to 40, especially preferably 3 to 30, specifically preferably 5 to 18 and in particular 8 to 14.

The nds (A) and (AQ) may be present as es of stereoisomers or as isolated stereoisomers. Tautomers and betaines are likewise encompassed by the structures (A) and (AQ).

In most cases, the composition according to the invention comprises from 0.1 to 90% by weight of the alkoxylate, preferably from 1 to 50% by weight and in particular from 3 to 30% by weight.

The term pesticide refers to at least one active substance selected from the group of the fungicides, insecticides, nematicides, herbicides, safeners, molluscicides, rodenticides and/or growth regulators. Preferred pesticides are fungicides, insecticides, ides and growth regulators. Especially preferred pesticides are herbicides and growth regulators. Mixtures of pesticides from two or more of the abovementioned classes may also be used. The skilled worker is familiar with such pesticides, which can be found, for example, in Pesticide Manual, 15th Ed. , The British Crop Protection Council, London. The pesticides may also comprise salts, esters, l isomers or tautomers. Suitable pesticides are s A) to M) are fungicides): A) Respiration inhibitors — complex-lll—inhibitors at the Qo—site (for example strobilurins): azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fenaminstrobin, fenoxystrobin/flufenoxystrobin, fluoxastrobin, kresoxim—methyl, nostrobin, orysastrobin, picoxystrobin, ostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, methyl 2—[2—(2,5—dimethylphenyloxymethyl)phenyl]— 3—methoxyacrylate, 2—(2—(3—(2,6—dichlorophenyl)—1—methylallylideneamino— oxymethyl)phenyl)—2—methoxyimino—N—methylacetamide, pyribencarb, pyricarb/chlorodincarb, famoxadon, fenamidon; - Complex—lll—inhibitors of the Qi—site: cyazofamid, amisulbrom; - Complex-ll-inhibitors (for example carboxamides): benodanil, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, ne, tecloftalam, thifluzamide, N-(4'-trif|uoromethylthiobiphenyl—2—yl)—3—difluoromethyl—1—methy|—1 H— pyrazole—4—carboxamide and N—(2—(1,3,3—trimethylbutyl)phenyl)—1,3—dimethyl—5— fluoro—1H—pyrazole—4—carboxamide; 4O — other respiration inhibitors (for example complex I, uncouplers): diflumetorim; nitrophenyl derivatives: binapacryl, dinobuton, dinocap, nam; ferimzone; organometal compounds: fentin salts such as fentin acetate, fentin chloride or PF 71968 WO 16939 7 fentine hydroxide; ametoctradin; and silthiofam; B) Sterol thesis inhibitors (SBI fungicides) Cl4—Demethylase inhibitors (DMI ides): triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole—M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, afol, hexaconazole, imibenconazole, ipconazole, azole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole; imidazoles: imazalil, pefurazoate, prochloraz, mizole; pyrimidines, pyridines and piperazines: fenarimol, Nuarimol, pyrifenox, triforine; delta14—reductase inhibitors: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine; 3—ketoreductase inhibitors: fenhexamid; C) Nucleic acid synthesis inhibitors phenylamides or acylamino acid fungicides: benalaxyl, benalaxyl—m, kiralaxyl, metalaxyl, metalaxyl—m (mefenoxam), ofurace, oxadixyl; : zole, octhilinone, oxolinic acid, mate; D) cell division and cytoskeleton inhibitiors 2O tubulin inhibitors such as benzimidazoles, thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate—methyl; triazolopyrimidines: 5—chloro— 7—(4—methylpiperidin—1—y|)—6—(2,4,6—trifluorophenyl)—[1,2,4]triazolo[1,5—a]pyrimidine; further cell division inhibitors: fencarb, ethaboxam, pencycuron, olid, zoxamid, metrafenon, pyriofenon; E) Amino acid synthesis and protein synthesis inhibitors methionine synthesis inhibitors (anilinopyrimidine): inil, mepanipyrim, pyrimethanil; n synthesis inhibitors: blasticidin—S, kasugamycin, kasugamycin hloride hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxin, validamycin A; F) Signal transduction tors MAP/histidine kinase inhibitors: fluoroimide, iprodione, procymidone, vinclozolin, fenpiclonil, fludioxonil; G—protein inhibitors: quinoxyfen; G) Lipid and membrane synthesis inhibitors Phospholipid biosynthesis inhibitors: edifenphos, iprobenfos, pyrazophos, isoprothiolane; Lipid peroxidation: dicloran, quintozene, tecnazene, tolclofos—methyl, yl, chloroneb, etridiazole; Phospholipid biosynthesis and cell wall attachment: dimethomorph, flumorph, 40 mandipropamid, pyrimorph, benthiavalicarb, iprovalicarb, valifenalate and 4—fluorophenyl N—(1—(1—(4—cyanophenyl)ethanesulfonyl)but—2—yl)carbamate; nds which affect cell membrane permeability and fatty acids: propamocarb, PF 71968 WO 16939 8 propamocarbhydrochloride H) “Multi—Site” inhibitors inorganic active substances: Bordeaux e, copper acetate, copper ide, copper oxychloride, basic copper sulfate, sulfur; Thio— and dithiocarbamates: ferbam, mancozeb, maneb, metam, metiram, propineb, thiram, zineb, ziram; organochlorine compounds (for example phthalimides, sulfamides, chloronitriles): anilazine, chlorothalonil, captafol, , , dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pentachlorophenol and its salts, phthalid, tolylfluanid, N—(4—chloro—2-nitrophenyl)—N—ethyl—4—methylbenzenesulfonamide; ines and others: guanidine, dodine, dodine free base, guazatin, guazatin acetate, iminoctadin, iminoctadin triacetate, iminoctadin tris(albesilate), dithianon; I) Cell wall biosynthesis inhibitors glucan synthesis inhibitors: mycin, polyoxin B; melanin synthesis inhibitors: pyroquilon, tricyclazole, carpropamid, omet, nil; J) Resistence inductors acibenzolar—S—methyl, probenazol, isotianil, tiadinil, prohexadione—calcium; phosphonates: fosetyl, fosetyl—aluminum, phosphorous acid and its salts; 2O K) Unknown mode of action bronopol, ethionate, cyflufenamid, cymoxanil, dazomet, debacarb, diclo— mezin, oquat, difenzoquat—methyl e, diphenylamine, fenpyrazamine, flumetover, flusulfamid, flutianil, methasulfocarb, nitrapyrin, nitrothal—isopropyl, oxine—copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2—butoxy—6—iodo— 3—propylchromene—4—one, lopropylmethoxyimino—(6—difluoromethoxy—2,3— difluorophenyl)methyl)—2—phenylacetamide, N'—(4—(4—chloro—3—trifluoromethyl— phenoxy)—2,5—dimethylphenyl)—N—ethyl—N—methylformamidine, N'—(4—(4—fluoro—3— trifluoromethylphenoxy)—2,5—dimethylphenyl)—N—ethyl—N—methylformamidine, N'—(2—methyl—5—trifluoromethyl—4—(3—trimethylsilanylpropoxy)phenyl)—N—ethyl—N— methylformamidine, N'—(5—difluoromethyl—2—methyl—4—(3—trimethylsilanyl— propoxy)phenyl)—N—ethyl—N—methylformamidine, N—methyl—(1 ,2,3,4—tetrahydronaphthalen—1—yl)—2—{1—[2—(5-methyl—3— trifluoromethylpyrazol—1—yl)acetyl]piperidin—4—yl}thiazolecarboxylate, N—methyl—(R)— 1 ,2,3,4-tetrahydronaphthaleny| 2—{1-[2—(5—methyltrifluoromethylpyrazoI yl)acetyl]piperidiny|}thiazoIecarboxylate, 1-[4-[4-[5-(2,6—difluorophenyl)—4,5-dihydroisoxazo |y|]thiazo|yl]—1—piperidinyl][5-methy|(trif|uoromethy|)-1 H-pyr— azol—1—yl]ethanone, 6—tert—butyl—8—fluoro—2,3—dimethquuinolin—4—yl methoxyacetate, N—methyl—2—{1—[(5—methyl—3—trifluoromethyl—1 H—pyrazol—1—y|)acetyl]piperidin—4—yl}-N— [(1 R)—1 ,2,3,4—tetrahydronaphthalen—1—yl]—4—thiazolecarboxamide, 3—[5—(4— 40 methylphenyl)-2,3—dimethylisoxazolidin—3—yl]—pyridine, 3—[5—(4—chlorophenyl)-2,3— dimethylisoxazolidin—3—yl]—pyridine (pyrisoxazol), N—(6—methoxypyridin—3—yl) cyclopropanecarboxamide, 5—chloro—1—(4,6—dimethoxypyrimidin—2—yl)—2—methyl—1 H— PF 71968 W0 2012/116939 9 benzoimidazole, 2—(4—chIorophenyl)—N—[4—(3,4—dimethoxyphenyl)isoxazoI—5—yl]—2— prop—2—ynyloxyacetamide; L) Biological fungicides, plant strengthening agents - Ampe/omyces a/is (for example the product AQ 10® from lntrachem Bio GmbH & Co. KG, Germany), Aspergi/lus flavus (for example the product AFLAGUARD® from Syngenta, Switzerland), Aureobasidium pullu/ans (for example the product BOTECTOR® from bio—ferm GmbH, Germany), Bacillus pumilus (for example strain NRRL No. B-30087 in SONATA® and ® Plus from AgraQuest Inc., USA), us subti/is (for example strain NRRL-No. B-21661 in RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuest Inc., USA), Bacillus subti/is var. iquefaciens F2824 (for example the product TAEGRO® from Novozyme Biologicals, Inc., USA), Candida o/eophi/a l—82 (for example the product ASPIRE® from Ecogen Inc., USA), a saitoana (for example the products BIOCURE® (in admixture with lysozym) and BIOCOAT® from Micro Flo Company, USA (BASF SE) and Arysta), chitosan (for example ARMOUR—ZEN from en Ltd., New Zealand), C/onostachys rosea f. /ata, also known as G/ioc/adium catenulatum (for example J1446: PRESTOP® from Verdera, Finland), Coniothyrium minitans (for example the product CONTANS® from ta, Germany), Cryphonectria parasitica (for example the product Endothia parasitica from CNICM, France), Cryptococcus a/bidus (for example the product YIELD PLUS® from Anchor Bio—Technologies, South Africa), Fusarium oxysporum (for example the products ® from S.l.A.P.A., Italy, and EAN® from Natural Plant Protection, France), Metschnikowia fructico/a (for example the product SH EMER® from Agrogreen, ), Microdochium dimerum (for example the product T® from ine, France), Phlebiopsis gigantea (for example the product ROTSOP® from Verdera, Finland), Pseudozyma osa (for example the product SPORODEX® from Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 (for example the product POLYVERSUM® from o SSRO, Biopreparaty, Czech ic), Reynoutria sach/inensis (for example the product REGALIA® from e Biolnnovations, USA), Ta/aromyces flavus V117b (for example the product PROTUS® from Prophyta, Germany), Trichoderma l/um SKT-1 (for example the product ECO—HOPE® from Kumiai Chemical ry Co., Ltd., Japan), T. atroviride L052 (for example the product SENTINEL® from Agrimm Technologies Ltd, New Zealand), T. harzianum T—22 (for example the product PLANTSHIELD® from BioWorks Inc., USA), T. harzianum TH 35 (for example the product ROOT PRO® from Mycontrol Ltd., Israel), T. num T-39 (for example the products TRICHODEX® and TRICHODERMA 2000® from Mycontrol Ltd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride (for example the product TRICHOPEL from Agrimm Technologies Ltd, New Zealand), T. harzianum ICCO‘IZ and T. viride ICCO8O (for example the product REMEDIER® WP from lsagro Ricerca, 40 Italy), T. polysporum and T. harzianum (for example the product BINAB® from BINAB Bio— lnnovation AB, Sweden), T. stromaticum (for example the product TRICOVAB® from C.E.P.L.A.C., Brazil), T. virens GL—21 (for example the product SOILGARD® from PF 71968 Certis LLC, USA), T. viride (for example the products TRIECO® from Ecosense Labs.

(India) Pvt. Ltd., India and BIO—CURE® F from T. Stanes & Co. Ltd., India), T. viride TV1 (for example the product T. viride TV1 from Agribiotec srl, Italy), U/ocladium nsii HRU3 (for example the product BOTRY—ZEN® from Botry—Zen Ltd, New M) growth regulators abscisic acid, amidochlor, ancymidole, 6—benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilid, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, cet, forchlorfenuron, gibberellic acid, inabenfid, indoleacetic acid, maleic hydrazide, mefluidid, mepiquat (mepiquat chloride), metconazole, naphthaleneacetic acid, N—6—benzyladenine, paclobutrazole, prohexadione (prohexadione—calcium), prohydrojasmone, thidiazuron, nthenol, tributylphosphorotrithioate, 2,3,5—triiodo— benzoic acid, trinexapac—ethyl and uniconazole; N) herbicides — acetamide: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, amid, naproanilid, amid, pretilachlor, propachlor, thenylchlor; — amino acid analogs: bilanafos, sate, glufosinate, sulfosate; 2O — aryloxyphenoxypropionates: clodinafop, cyhalofop—butyl, fenoxaprop, fluazifop, haloxyfop, fop, propaquizafop, quizalofop, quizalofop—P—tefuryl; — bipyridyls: diquat, paraquat; — carbamates and thiocarbamates: asulam, butylate, carbetamide, desmedipham, dimepiperat, eptam (EPTC), esprocarb, molinate, arb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate; — exanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim; — dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, mine, ralin; — diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oyfluon‘en; - hydroxybenzonitriles: bromoxynil, dichlobenil, ioxynil; - imidazolinones: imazamethabenz, ox, imazapic, imazapyr, imazaquin, imazethapyr; - phenoxyacetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA—thioethyl, MCPB, mecoprop; — pyrazines: chloridazon, flufenpyr—ethyl, fluthiacet, norflurazon, te; — pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, nafen, thiazopyr; 40 — sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron—ethyl, chlorsulfuron, lfuron, cyclosulfamuron, ethoxysulfuron, ulfuron, o— sulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, PF 71968 W0 2012/116939 11 mesosulfuron, metsulfuron—methyl, nicosulfuron, oxasulfuron, primisulfuron, pro— sulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, tria— sulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1—((2—chloro—6—propyl— imidazo[1 ,2—b]pyridazin—3—yl)sulfonyl)—3—(4,6—dimethoxypyrimidin—2—yl)urea; triazines: ametryne, atrazine, cyanazine, ametryne, ethiozine, hexazinone, metamitron, uzine, prometryne, simazine, terbuthylazine, terbutryne, triaziflam; ureas: chlortoluron, daimuron, diuron, fluometuron, isoproturon, linuron, methabenz— thiazuron, tebuthiuron; other acetolactate se inhibitors: bispyribac-sodium, cloransulam-methyl, 1O diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, orthosulfamuron, penoxsulam, propoxycarbazone, pyribambenz—propyl, pyribenzoxim, pyriftalide, pyriminobac—methyl, pyrimisulfan, pyrithiobac, pyroxasulfon, pyroxsulam; others: amicarbazone, riazole, anilofos, beflubutamid, benazolin, bencarbazone, benfluresate, benzofenap, bentazone, benzobicyclon, il, bromobutide, butafenacil, butamifos, cafenstrole, carfentrazone, cinidon—ethlyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfamid, dicamba, difenzoquat, diflufenzopyr, Drechs/era monoceras, al, ethofumesate, etobenzanid, fentrazamide, flumiclorac—pentyl, flumioxazin, flupoxam, chloridon, mon, indanofan, isoxaben, isoxaflutol, lenacil, propanil, propyzamide, quinclorac, 2O quinmerac, ione, methylarsenic acid, naptalam, oxadiargyl, oxadiazone, oxaziclomefon, azone, pinoxaden, pyraclonil, pyraflufen—ethyl, pyrasulfotol, pyrazoxyfen, pyrazolynate, quinoclamin, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, rione, thiencarbazone, topramezone, 4—hydroxy—3—[2—(2— methoxyethoxymethy|)—6—trifl uoromethylpyridin—3—carbonyl]bicyc|o[3.2.1]oct—3—en—2— one, ethyl (3—[2—chIoro—4—fluoro—5—(3—methyl—2,6—dioxo—4—trifluoromethyl—3,6—dihydro—2H— pyrimidin—1—yl)phenoxy]pyridin—2—yloxy)acetate, methyl 6—amino—5—chloro—2—cyclo— propylpyrimidine—4—carboxylate, ro—3—(2—cyclopropyl—6—methylphenoxy)— pyridazin—4—ol, 4—amino—3—chloro—6—(4—chlorophenyl)—5—fluoropyridin—2—carb0xylic acid, methyl 4—amino—3—chloro—6—(4—chloro—2—fluoro—3—methoxyphenyl)pyridin—2—carboxylate and methyl 4—amino—3—chloro—6—(4—chloro—3—dimethylamino—2—fluorophenyl)pyridin—2— carboxylate; O) insecticides organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoat, disulfoton, ethion, fenitrothion, fenthion, isoxathion, ion, methamidophos, methidathion, methyl—parathion, mevinphos, monocrotophos, eton—methyl, paraoxon, parathion, phenthoate, one, phosmet, phosphamidon, phorate, phoxim, pirimiphos—methyl, profenofos, ofos, sulprophos, tetrachlorvinphos, 40 terbufos, phos, trichlorfon; PF 71968 — carbamates: alanycarb, aldicarb, carb, benfuracarb, carbaryl, carbofuran, carbosulfan, carb, furathiocarb, methiocarb, methomyl, , pirimicarb, propoxur, thiodicarb, triazamate; — pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha—cypermethrin, beta—cypermethrin, zeta—cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, Iambda—cyhalo— thrin, permethrin, prallethrin, pyrethrin | and II, resmethrin, silafluofen, tau— fluvalinate, tefluthrin, ethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin, - insect growth inhibitors: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, enzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazin; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, rene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramate; — ne receptor ts/antagonists: clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1—(2—ch|orothiazo|—5—y|methy|)— 2—nitrimino—3,5—dimethyI—[1,3,5]triazinane; — GABA antagonists: endosulfan, ethiprole, fipronil, prole, pyrafluprole, pyriprole, 2O N—5—amino—1—(2,6—dichloro—4—methylphenyI)—4—sulfinamoyI—1 H—pyrazole—B—thiocarbox— amide; — macrocyclic es: abamectin, emamectin, milbemectin, lepimectin, spinosad, spinetoram; — mitochondrial electron transport chain inhibitor (METI) | acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim; — METI II and Ill substances: acequinocyl, fluacyprim, hydramethylnone; — decouplers:chlorfenapyr; — inhibitors of oxidative phosphorylation: cyhexatin, diafenthiuron, fenbutatin oxide, propargite; — insect ecdysis inhibitors: cryomazin; - ‘mixed function oxidase’ inhibitors: piperonyl butoxide; - sodium channel blockers: indoxacarb, metaflumizon; - others: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozin, sulfur, thiocyclam, flubendiamid, chlorantraniliprole, cyazypyr (HGW86); cyenopyrafen, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, fluron and pyrifluquinazone. es of safeners are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, late, orazole, rim, ole, fluxofenim, 40 furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, hloroacetyI)—1—oxa—4—azaspiro[4.5]decane (CAS 07—3) and 2,2,5—trimethyl— 3—(dichloroacetyI)—1,3—oxazolidine (CAS 52836—31—4).

PF 71968 W0 2012/116939 13 Preferred pesticides comprise at least one pesticide with at least one H-acidic group (such as carboxylic acid group, phosphonic acid group, phosphinic acid group) or the anionic salts f (e.g., mono, di or tri salts). These anionic salts of the pesticides with an H—acidic group are also suitable as c pesticides in group A‘. Preferred pesticides with an H—acidic group are ides with an H-acidic group. Examples of herbicides with an H—acidic group are amino acid s (such as glyphosate or glufosinate) or olinones (such as imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr).

Particularly preferred pesticides with an H—acidic group are glyphosate and glufosinate.

In another preferred embodiment, pesticides with an H—acidic group are imidazolinones.

Especially preferably, the pesticide comprises a pesticide with an H—acidic group and one further ide. In another embodiment the pesticide comprises mixtures of at least two pesticides with an H—acidic group, and optionally further pesticides (such as at least one fungicide, herbicide, insecticide, and/or safener, with fungicides and/or herbicides being preferred).

In a further red embodiment, the pesticide comprises glyphosate (for example as the free acid, sodium salt, sesquisodium salt, potassium salt, dipotassium salt, ammonium salt, diammonium salt, dimethylammonium salt, trimesium salt or isopropyl— amine sale) or glufosinate (for example as the ammonium salt). With particular preference the pesticide comprises sate (for example as the potassium salt, ammonium salt or pylamine salt). With particular preference the pesticide ses glyphosate or glufosinate, and additionally a further herbicide. In another preferred embodiment the pesticide ses sate or glufosinate, and additionally a further pesticide (such as at least one fungicide, ide, insecticide and/or safener, with fungicides and/or herbicides being preferred).

Specifically preferably, the pesticide comprises glyphosate and at least one further herbicide selected from the following list: acetochlor,acif|uorofen, aclonifen, acrolein, alachlor, ametryn, amidosulfuron, le, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazon, benzofenap, bialaphos, bifenox, il, bromobutide, bromofenoxim, bromoxynil, butachlor, butamifos, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone—ethyl, chlomethoxyfen, chloroamben, chlorobromuron, chloroidazon, imuron—ethyl, nitrofen, 40 chloroacetic acid, toluron, chloropropham, chlorosulfuron, thal—dimethyl, chlorothiamid, cinmethylin, cinosulfuron, clethodim, clodinafop—propargyl, clomazone, clomeprop, clopyralid, cloransulam—methyl, cyanazine, cycloate, cyclosulfamuron, PF 71968 W0 2012/116939 14 cycloxydim, cyhalofop—butyl, 2,4—D,2,4—DB, daimuron, dalapon, ipham, desmetryn, dicamba, dichlobenil, dichloroprop, diclofop—methyl, difenzoquat, diflufenican, ron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dinitramine, dinoterb, diphenamid, diquat, dithiopyr, diuron, endothall, EPTC, esprocarb, ethalfluralin, ethametsulfuron—methyl, mesate, ethoxysulfuron, zanid, fenac, fenoxaprop, fenoxaprop—ethyl, fenuron, flamprop, flamprop—methyl, flazasulfuron, fluazifop—butyl, fluchloralin, flumetsulam, flumiclorac, flumiclorac—pentyl, flumioxazin, fluometuron, fluorochloridone, glycofen, fluoroglycofen-ethyl, flupoxam, flupropanate, flurenol, fluridone, fluroxypyr-t- methylheptyl, flurtamone, fluthiacet—methyl, fomesafen, fosamine, glufosinate, halosulfuron, haloxyfop-methyl, hexazinone, imazameth, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, ulfuron, indanofan, ioxynil, isoproturon, isouron, isoxaben, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPB, op, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, arsonic acid, methyldymron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, te, monolinuron, naproanilide, napropamide, naptalam, neburon, nicosulfuron, nonanoic acid, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxyfluorfen, paraquat, pebulate, pendimethalin, pentanochlor, azone, dipham, picloram, piperophos, 2O pretilachlor, primisulfuron, prodiamine, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen—ethyl, pyrazolynate, pyrazosulfuron—ethyl, pyrazoxyfen, pyributicarb, pyridate, pyriminobac—methyl, quinclorac, rac, quizalofop—ethyl, rimsulfuron, sethoxydim, siduron, ne, simetryn, sulcotrione, sulfamic acid, sulfentrazone, sulfometuron, sulfosulfuron, TCA, tebutam, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thifensulfuron, thiobencarb, bazil, tralkoxydim, triallate, triasulfuron, tribenuron, 2,3,6- orobenzoic acid, triclopyr, trietazine, trifluralin, triflusulfuron, vernolate.

In a further, specifically preferred embodiment, the pesticide comprises imazamox and at least one further herbicide selected from among the following classes hi) to b15): b1) lipid biosynthesis inhibitors: chloroazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop—p, fenthiaprop, fluazifop, fluazifop-P, fop, haloxyfop—P, yrifop, metamifop, propaquizafop, quizalofop, quizalofop-P, trifop, alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, xydim, butylae, cycloate, diallate, dimepiperate, EPTC, esprocarb, ethiolate, isopolinate, methiobencarb, molinate, arb, pebulate, prosulfocarb, sulfallate, thiobencarb, tiocarbazil, triallate, vernolate, benfuresate, ethofumesate, bensulide and den; b2) ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron, chloroimuron, 40 chlorosulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethoxysulfuron, flazasulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, furon, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, PF 71968 W0 2012/116939 15 pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, imazamethabenz, imazapic, yr, imazaquin, imazethapyr, cloransulam, diclosulam, ulam, flumetsulam, metosulam, penoxsulam, bispyribac, pyriminobac, propoxycarbazone, flucarbazone, nzoxim, pyriftalid, pyrithiobac, flucetosulfuron, orthosulfamuron, pyrimisulfan; b3) ynthesis inhibitors: atraton, atrazine, ametryne, aziprotryne, cyanazine, cyanatryn, chloroazine, cyprazine, desmetryne, dimethametryne, dipropetryn, eglinazine, ipazine, mesoprazine, methometon, rotryne, procyazine, anzine, prometon, prometryne, propazine, sebuthylazne, secbumeton, simazine, n, yne, terbumeton, terbuthylazine, terbutryne, trietazine, ametridione, amibuzin, hexazinone, isomethiozin, tron, metribuzin, bromacil, isocil, lenacil, terbacil, brompyrazon, chloridazon, dimidazon, desmedipham, phenisopham, phenmedipham, phenmedipham—ethyl, benzthiazuron, buthiuron, ethidimuron, n, methabenzthiazuron, monisouron, tebuthiuron, thiazafluron, anisuron, buturon, romuron, chloreturon, chlorotoluron, chloroxuron, difenoxuron, dimefuron, diuron, fenuron, fluometuron, fluothiuron, isoproturon, linuron, methiuron, metobenzuron, metobromuron, metoxuron, monolinuron, monuron, neburon, parafluron, phenobenzuron, siduron, tetrafluron, thidiazuron, cyperquat, diethamquat, difenzoquat, diquat, morfamquat, at, onil, bromoxynil, chloroxynil, iodobonil, ioxynil, 2O amicarbazone, bromofenoxim, flumezin, methazole, bentazone, propanil, pentanochlor, pyridate and pyridafol; b4) protoporphyringogen—IX oxidase inhibitors: acifluorofen, bifenox, thoxyfen, chloronitrofen, ethoxyfen, fluorodifen, fluoroglycofen, nitrofen, fomesafen, furyloxyfen, halosafen, lactofen, nitrofen, nitrofluorfen, oxyfluon‘en, fluazolate, pyraflufen, cinidon—ethyl, flumiclorac, flumioxazin, flumipropyn, fluthiacet, zimin, zon, oxadiargyl, azafenidin, carfentrazone, sulfentrazone, pentoxazone, benzfendizone, butafenacil, pyraclonil, azol, pyr, flupropacil, nipyraclofen, etnipromid, saflufenacil and bencarbazone; b5) bleacher herbicides: metfluazon, norflurazon, flufenican, diflufenican, picolinafen, beflubutamid, fluridone, flurochloridone, flurtamone, mesotrione, sulcotrione, isoxachlortole, isoxaflutole, benzofenap, pyrazolynate, pyrazoxyfen, benzobicyclon, le, clomazone, aclonifen, 4-(3-trifluoromethyl—phenoxy)—2—(4—trifluoromethylphenyl)pyrimidine, disclosed in EP 723960, topramezone, 4—hydroxy—3—{[2—methyl—6—(trifluoromethyl)-3— pyridinyl]carbony|}bicyc|o[3.2.1]oct—3—en—2—one, disclosed in WO 00/15615, 4—hydroxy— 3-{[2-(2—methoxyethoxy)methyl(trifluoromethyl)—3-pyridinyl]carbonyl}bicyclo[3.2.1]oct— 3-en-2—one, disclosed in W0 01 /94339, 4-hydroxy[4-(methylsulfonyl)—2— nitrobenzoyl]bicyclo[3.2.1]—oct—3-en—2—one, disclosed in EP 338992, 2—[2-chloro (methylsulfonyl)—3—[(2,2,2—trifluoroethoxy)methyl]—3—hyd roxy—3—cyclohexen—1 —one (disclosed in DE 19846792) and pyrasulfotole; b6) EPSP synthase inhibitors: glyphosate; b7) glutamine se inhibitors: glufosinate and bilanaphos; b8) DHP 40 synthase inhibitors: asulam; b9) mitosis inhibitors: ralin, butralin, dinitramine, ethalfluralin, fluchloralin, palin, methalpropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin, trifluralin, amiprofos—methyl, butamifos, dithiopyr, thiazopyr, PF 71968 propyzamide, tebutam, chlorthal, carbetamide, chlorbufam, chlorpropham and m; b10) VLCFA tors: acetochlor, alachlor, butachlor, chlor, delachlor, diethatyl, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, S—metolachlor, pretilachlor, hlor, propisochlor, prynachlor, terbuchlor, thenylchlor, xylachlor, allidochlor, CDEA, epronaz, diphenamid, napropamide, nilide, pethoxamid, flufenacet, mefenacet, fentrazamide, anilofos, piperophos, cafenstrole, indanofan and tridiphane; b11) cellulose biosynthesis inhibitors: dichlobenil, hiamid, isoxaben and flupoxam; b12) decoupler herbicides: dinofenate, dinoprop, dinosam, dinoseb, rb, DNOC, etinofen and medinoterb; b13) auxin herbicides: rop, 2,4-D, 2,4,5-T, MCPA, MCPA thioethyl, dichlorprop, dichlorprop—P, mecoprop, mecoprop—P, , MCPB, chloramben, dicamba, 2,3,6— TBA, tricamba, quinclorac, quinmerac, clopyralid, fluroxypyr, picloram, triclopyr, benazolin and aminopyralid; b14) auxin transport inhibitors: naptalam, enzopyr; b15) benzoylprop, flamprop, flamprop—M, bromobutide, chlorflurenol, cinmethylin, methyldymron, etobenzanid, fosamine, metam, pyributicarb, oxaziclomefone, dazomet, triaziflam, methyl bromide.

Suitable surfactants are, in particular anionic, cationic, nonionic and eric surfactants, block polymers and polyelectrolytes. Preferred surfactants are anionic 2O surfactants and nonionic surfactants. In an especially preferred embodiment, surfactants are anionic surfactants. In a further especially, surfactants are nonionic surfactants.

Suitable c surfactants are surfactants comprising an anionic group such as sulfonates, sulfates, phosphates or carboxylates. The anionic surfactants can be employed in the form of alkali metal, alkaline—earth metal or ammonium salts, or else in the form of the free acid. Preferred anionic surfactants are sulfonates and phosphates.

In one embodiment, phosphonates are especially preferred. In a further embodiment, phosphates are especially preferred.

Examples of sulfonates are rylsulfonates, diphenylsulfonates, alpha— olefinsulfonates, Iigninosulfonates, sulfonates of fatty acids and of oils, ates of lated alkylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, uccinates or sulfosuccinamates. Preferred sulfonates are alkylarylsulfonates, especially preferred is 03alkylbenzenesulfonate. Such alkylarylsulfonates can be prepared by sulfonating alkylbenzene with sulfur de. Alkylarylsulfonates are commercially available as C10.13—alkylbenzenesulfonate, the free acid, or 010—13-alkyl— benzenesulfonate, alkanolamine salt. The alkylarylsulfonates are preferably present in 40 the form of the free acid or as an alkanolamine salt (for example triethanolamine). es of sulfates are sulfates of fats and oils, of ethoxylated alkylphenols, of PF 71968 W0 2012/116939 17 06-32—alcohols, of ethoxylated alcohols, or of fatty acid esters. Preferred sulfates are sulfates of 012-22—alcohols and of ethoxylated Cealcohols.

Examples of phosphates are phosphate esters. Preferred phosphates are phosphate esters of alkoxylates, such as ate esters of alkanol alkoxylates. Preferred phosphates are phosphate esters of C6.22—alkanol alkoxylates (in particular 08-14—alkanol alkoxylates). The alkoxylate units is usually composed of ethylene oxide and/or propylene oxide. In most cases, it has a mean number of alkoxide units in the range of from 6 to 30, ably from 12 to 18. The phosphates are preferably in the form of the free acid or as alkanolamine salt (for example anolamine). The phosphate esters can be present as phosphate monoesters or phosphate rs or as a mixture of these.

Examples of carboxylates are alkyl carboxylates and carboxylated alcohol ethoxylates or alkylphenol ethoxylates. Preferred carboxylates are alkyl carboxylates, such as those having 8—32 carbon atoms,, in particular 10 to 22 carbon atoms. es are fatty acids, which may also be present in industrial mixtures of chain lengths of, for example, from 10 to 22 carbon atoms. 2O Suitable nonionic surfactants are lates, N—alkylated fatty acid , amine oxides, esters or sugar—based surfactants. Preferred nonionic surfactants are lates and sugar—based surfactants. In one ment, alkoxylates are especially preferred. In a further embodiment, sugar—based surfactants are especially red.

Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated.

Ethylene oxide and/or propylene oxide may be used for the alkoxylation, preferably ne oxide. Preferred alkoxylates are alkanol alkoxylates, preferably linear and branched, saturated or unsaturated C4.2z—alkanol alkoxylates, the alkoxylate being composed of ethylene oxide and/or propylene oxide. The l alkoxylate typically comprises a mean number of alkoxide units in the range of from 2 to 50, preferably from 2.2 to 20, especially ably from 2.8 to 12 and in particular from 2.8 to 8.

Alkanol alkoxylates are commercially available from BASF SE as Emulan® types, Plurafac® types or ol® types.

Examples of N-alkylated fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.

Examples of esters are fatty acid esters, glycerol esters or monoglycerides.

Examples of sugar-based surfactants are sorbitans, ethoxylated ans, sucrose esters and glucose esters or alkyl polyglucosides. Preferred sugar—based surfactants PF 71968 are Gem—alkyl polyglucosides, for example with a DP. (degree of polymerization) of from 1.2 to 1.9.

Suitable cationic surfactants are nary surfactants, for example quaternary ammonium nds with one or two hobic groups, or salts of long—chain primary amines.

Suitable amphoteric surfactants are alkylbetains and imidazolines. 1O Suitable block polymers are block polymers of the A—B or the A—B-A type, it being possible for the blocks A and B to be polyethylene oxide, polypropylene oxide or polybutylene oxide. Preferred examples are A—B block polymers composed of polyethylene oxide and polypropylene oxide, or polyethylene oxide and polybutylene oxide; and A—B—A block polymers ed of polyethylene oxide and polypropylene oxide, or polyethylene oxide and polybutylene oxide (in particular polyethylene oxide/polypropylene oxide/polyethylene oxide). Others which are furthermore also suitable are block polymers of the A—B—C type comprising polyethylene oxide, polypropylene oxide and polybutylene oxide. 2O Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali metal salts of polyacrylic acid. es of polybases are polyvinylamines or polyethyleneamines.

Especially preferred is at least one tant selected among sulfonates, phosphates, alkoxylates and sugar—based surfactants (e.g. in itions comprising an alkoxylate, wherein R7 is a ed alkyl radical C9H19, 2—propylheptyl or 2— ethylhexyl). Very especially preferred is at least one surfactant selected among alkylarylsulfonates, phosphate ester of alkoxylates, alkanol alkoxylates and alkyl ucosides (e.g. in compositions comprising an alkoxylate, wherein R7 is a branched alkyl l C9H19, 2—propylheptyl or 2—ethylhexyl).

A series of surfactants are advantageously suitable for the ition according to the invention: a) In a preferred embodiment, the surfactant is a C1e-1s-alkanol alkoxylate, where the alkoxylate is composed of ethylene oxide and/or propylene oxide and the alkanol alkoxylate has a mean number of alkoxide units in the range of from 12 to 35, ably from 17 to 26. b) In a further preferred embodiment, the surfactant is a C1o—Guerbet l alkoxylate, where the alkoxylate is composed of ethylene oxide and the alkanol 40 alkoxylate has a mean number of alkoxide units in the range of from 2 to 8, preferably from 2.5 to 6.

PF 71968 c) In a further preferred embodiment, the surfactant is an iso—C13—alkanol alkoxylate, where the alkoxylate is ed of ethylene oxide and the alkanol alkoxylate has a mean number of alkoxide units in the range of from 3 to 10, preferably from 4.5 to d) In a further preferred embodiment, the surfactant is a C4-g-alkanol alkoxylate, where the alkoxylate is ed of ethylene oxide and the alkanol alkoxylate has a mean number of alkoxide units in the range of from 2 to 9, preferably from 3.5 to 7. e) In a preferred embodiment, the tant is a Cg-1o-alkylpolyglucoside with a DP. offrom 1.4 to 1.9, ably from 1.6 to 1.8. 1O f) In a further preferred embodiment, the surfactant is a 08alkylbenzenesulfonate. g) In a further preferred embodiment, the surfactant is a phosphate ester of 08—14—alkanol alkoxylates.

Among the aforementioned series the surfactants b), c), e) and 13 are more advantageously suitable.

In another embodiement, the surfactant is selected from the groups b1) to b5): b1) a nonionic surfactant of the formula R11Xn and polyalkoxylated derivatives f, wherein R11 is selected from aliphatic or aromatic residues having at least eight 2O carbon atoms; X is selected from hydroxy, —Ce—alkyl), —O—(Cg—Ce—alkenyl), amine, amide, or ester; and n is 1, 2, 3, 4, 5 or 6; b2) an anionic surfactant of the formula R11Yn, wherein R11 is selected from aliphatic or aromatic residues having at least eight carbon atoms; Y is selected from carboxylate, sulfonate, sulfate, phosphate, or onate; and n is 1, 2, 3, 4, 5 or 6; b3) a cationic tant; b4) a zwitterionic surfactant; or b5) a polymeric surfactant.

In particular, the surfactant may be selected from b1) nonionic surfactants of the formula R‘1Xn and polyalkoxylated derivatives thereof (as defined below), wherein R11 is selected from aliphatic or aromatic residues having at least eight carbon atoms; X is ed from hydroxy, —O—(C1—Ce—alkyl), —Ce—alkenyl), amine, amide, or ester; and n is 1, 2, 3, 4, 5, or 6. yl for example would be propyl (R11) containing three hydroxy groups (X). In case X is hydroxy, preferably at least one of the hydroxy groups is polyalkoxylated. The surfactant b1 is preferably selected from polyalkoxylated derivatives of the formula R11Xn. Preferred amides are mono— or di—C1—Ca—alkylamides and mono— or di—C1—Cg—acylamides, wherein the alkylamides are particularly preferred. 40 R11 is preferably selected from aliphatic or ic es having at least 10, more preferably at least 12 carbon atoms. The aromatic residues may contain aliphatic and/or aromatic substitutents. In another form, R11 is ed from aliphatic or PF 71968 W0 2012/116939 20 aromatic residues having from 8 to 30, preferably from 10 to 22 and in particular from 12 to 18 carbon atoms. R11 is preferably selected from aliphatic residues having at least 10, more preferably at least 12 carbon atoms. The aliphatic residues may be linear or branched, saturated or rated. Examples for R11 are: 2,4,6— triisopropylphenyl, yrylphenyl, n—octyl, n—decyl, n—undecyl, n-dodecyl, ecyl, n— ecyl, n—hexadecyl, n—octadecyl, 2—ethylhexyl, 1—methylnonyl, 2—propylheptyl, 1— methyldecyl, 1—methylundecyl, isotridecyl, n—tetradecenyl, 1-methylpentadecyl, n— hexadecenyl, n-hexadecadienyl, n-octadecenyl, n-octadecadienyl. 1O The surfactant b1 is preferably ed from nonionic surfactants of polyalkoxylated derivatives of the formula R11Xn, wherein R11 is selected from aliphatic or aromatic residues having at least eight carbon atoms; and X is selected from hydroxy, amine or amide. The koxylated derivatives of the formula R11Xn contain a polyalkoxylate residue, which may contain 5 to 50 (preferably 6 to 25 and in particular 6 to 20) equivalents of a Cz—Ce—alkylenoxide. Typically, R11Xn contains one or two polyalkoxylate residues per each residue X, depending on the free valences of X. In case X is hydroxy, said hydroxy group may contain one polyalkoxylate residue per each y group. In case X is amine, said amine group may contain one or two, preferably two, polyalkoxylate residues per each amine group. Preferably, the alkyleneoxide is 2O selected from ethylene oxide, propylen oxide, neoxide, and mixtures f. In a preferred form, the polyalkoxylated derivatives of the formula R11Xn contain polyethyleneoxide residues, which may contain 6 to 15 lents of an ethyleneoxide. Preferred are poly(Cz—Ce alkoxylate) residues, such as polyethyleneoxide, polypropyleneoxide. The neoxide units may be in random or block sequence (such as EO—PO—EO). The alkyleneoxide units may further substituted with other onal groups, such as alkyl, acyl, or polyethylene glycol groups. The polyalkoxylate residue may be terminated by hydrogen or any organic group, such as C1-C8 alkyl.

In a further embodiment, X may be selected from ethoxylated derivatives of amides, which may contain 1 to 20 lents of ethylene oxide.

In a further embodiment, X may be selected from alkoxylated derivatives of esters, wherein the polyalkoxylate residue contains 1 to 50 (preferably 2 to 25 and in particular 5 to 25) equivalents of an 02alkylenoxide.

Especially red surfactant b1) of the formula R11Xn are — ethoxylated isotridecylalcohols containing 5, 6, 8, 15, or 20 ethylenoxide equivalents, and optionally terminated with a methyl group, 40 — alkoxylated ylheptylalcohols containing 10 ethylenoxide equivalents, and optionally 2 or 5 propylene oxide equivalents, PF 71968 W0 2012/116939 21 2012/053230 — alkoxylated linear, saturated fatty alcohols, such as lated linear, ted 016-13 fatty alcohols containing 2 to 80 ethylenoxide equivalents, - alkoxylated 2—propylheptylamines, e.g. containing 7 to 15 ethylenoxide equivalents, - alkoxylated tallow amine, e.g. containing 10 to 20 ethylenoxide equivalents, - alkoxylated isodecanol, e.g. containing 5 to 15 ethylenoxide equivalents, - alkoxylated C1o—Guerbet alcohols, e.g. containing 5 to 15 ethylenoxide equivalents, - alkoxylated 013/15-oxoalcohols, e.g. containing 5 to 30 ethylenoxide equivalents, 1O — alkoxylated linear, saturated fatty alcohols, which contain at least one ethylenoxide equivalent and at least one 03.5 alkyleneoxide equivalent, — ethoxylated n—dodecanol (8 EO), — ethoxylated fatty acid (saturated or rated) containing 5 to 20 ethylenoxide equivalents, optionally ated by a acyl (e.g. derived from a fatty acid), — ethoxylated fatty acid monoamide ated or unsaturated) containing 5 to 20 ethylenoxide equivalents, — ethoxylated fatty acid diamide (saturated or unsaturated) containing 10 to 40 noxide equivalents, — ethoxylated glycerol containing a total of 10 to 45 ethylenoxide equivalents and 2O up to 15 in each polyethoxylate chain, ally terminated by -8IKYI.

The tant b2) may be selected from b2) anionic surfactants of the formula R11Yn, wherein R11 is selected from aliphatic or aromatic residues having at least eight carbon atoms; Y is selected from carboxylate, sulfonate, sulfate, phosphate, or phosphonate; and Y is 1, 2, 3, 4, 5 or 6. The e R11 is defined as disclosed above for R11Xn.

The anionic surfactant may be present as , alkaline earth, ammonium, or aliphatic amine (e.g. hydroxyethylammonium, trihydroxyethylammonium, tetrahydroxyethylammonium, trihydroxypropylammonium) salts.

Especially preferred surfactant b2) of the formula R11Yn are — aliphatic monocarboxylate, such as fatty acids or sarcosinates, — aliphatic arboxylates, such as malonate or succinate tives, - sulfonamidocarboxylates, - aliphatic or aromatic sulfates, - polyethersulfates, — amidopolyethersulfates, — sulfated carboxylates, carbonic acid glycerides, or carbonic esters, — aliphatic or aromatic sulfonates, — sulfonated carboxylic esters or carboxylic amides, 40 — sulfosuccinic acid esters, PF 71968 W0 2012/116939 22 2012/053230 — polyethersulfonates, — polyether phosphates, such as tristyryl polyetherphosphate or phosphate ester of polyalkoxylated fatty alcohol, — polyether e, such as fatty alcohol polyethersulfate, — polyalkoxylated derivatives of the a R11Xn, wherein the polyalkoxylate residue is terminated by a residue Y.

The surfactant b3) may be selected from b3) cationic surfactants R112", which usually se a lipophilic part, such as R11 as disclosed above; a cationic group Z; n n is 1, 2, 3, 4, 5 or 6. Suitable cationic groups Z are ammonium; mono-, di-, tri-, or tetrasubstituted ammonium, wherein the substituents may be selected from (31-010 alkyl (e.g. methyl, ethyl, propyl, allyl), benzyl, C1—Cg—alkylether or a polyethylene glycol residue; di—C1—C12—alkylsulfonium; or nitrogen containing aromatic groups, such as N— substituted derivatives of pyrrol, pyridin, chinolin or isochinolin, imidazol, oxazol, thiazol. The cationic tant may be present as salt, eg. salt of acetate, formiate, propionate, sulfonate, sulfate, methylsulfate, methylsulfonate, phosphate, or nide (e.g. chloride, bromide or iodide).

Especially preferred surfactant b3) ed from cationic surfactants are salts of 2O — trimethyl—C1—Czo alkylammonium — C1-C20 alkylammonium, — di—C1-Czo alkylammonium, — tri—C1—Czo mmonium, — benzyltri—C1—Czo alkylammonium, — N-substituted pyridinium, — tives of N,N’—C1—C12—dialkylimidazolium, — derivatives of N—C1—C12—oxazolium, — derivatives of N—C1—C12—thiazolium, — Cg—Czo—alkyl—dimethylsulfonium, — 01—020 carboxylic acid esters of 2—hydroxyethyl—trimethylammonnium, — 01—020 ylic acid esters of ethoxylated (1-15 EO) 2—hydroxyethyl— — trimethylammonnium, - tri-C1-Czo alkyl-C1-Czo alkoxylammonium.

The surfactant b4) may be selected from b4) zwitterionic surfactants, which usually comprise a lipophilic part, such as R11 as disclosed above, an anionic group, such as Y as sed above, and a cationic group Z as disclosed above.

Especially preferred surfactant b4) selected from zwitterionic surfactants are 40 — tri—C1—Czo min N—oxide, — betains, such as N,N,N—tri—C1—Czo—alkylglycine, PF 71968 W0 2012/116939 23 — aminocarboxylic acids, — dimethylammonium terminated ethoxylated Ci—Czo—alkylphosphonate, — derivatives of d—sulfated C3—C20—carbonic acid 2—(trimethylammonium) —ethylester, — —C1—C20—alkylammonium)—C2—C20—alkylsulfonic acid, — [(3—Dodecanoylamino—propyl)—dimethyl—ammonium]—acetic acid.

The surfactant b5) may be selected from b5) polymeric surfactants, which y have a molecular weight of at least 2000 g/mol, preferably at least 5000 g/mol. The polymeric tant may be built from monomers, such as derivatives of N-vinyl amines, C2-C4 alkylen oxide, (meth)acry|ates, acrylic acid, N—vinylformamides, N— vinylpyridines, AMPS. The monomers may be in random or block sequence. Suitable block polymers are block polymers of the A—B or A—B—A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A—B—C type comprising l, polyethylene oxide and polypropylene oxide. The block polymers may be terminated by en or C1—C4 alkyl groups.

Most preferred surfactants from the groups b1) to b5) are selected from: polyether phosphates, in particular phosphate ester of polyalkoxylated fatty 2O alcohol; alkoxylated 2—propylheptylamines, particular ethoxylated 2—propylheptylamines containing 7 to 15 ethylenoxide equivalents, alkoxylated tallow amine, in particular ethoxylated tallow amine containing 10 to 20 ethylenoxide equivalents, polyether e, in particular lauryl alcohol polyethersulfate, ethoxylated isotridecylalcohols, in particular those containing at least 5 ethylenoxide equivalents, alkoxylated linear, saturated fatty alcohols, in particular alkoxylated linear, ted C1648 fatty alcohols containing 10 to 80 ethylenoxide equivalents, alkoxylated isodecanols, in particular those containing 4 to 15 noxide equivalents, alkoxylated C1o—Guerbet alcohols, in particular those containing 5 to 15 ethylenoxide equivalents, alkoxylated 013/15-oxoalcohols, in particular those containing 5 to 30 ethylenoxide equivalents, A—B—A type block polymers comprising blocks A of polyethylene oxide and blocks B of polypropylene oxide, which may have a molecular weight of from 800 to 8000 alkoxylated , ted fatty alcohols, which contain at least one ethylenoxide 40 equivalent and at least one C34; alkyleneoxide equivalent.

PF 71968 Specific, non—limiting examples for preferred surfactants from the groups b1) to b5) are the following surfactants: T1 ethoxylated isotridecylalcohol containing 8 ethylenoxide equivalents.

T2 lated tallow amine containing 15 ethylenoxide equivalents.

T3 ethoxylated 2—propylheptylamines containing 10 ethylenoxide equivalents.

T4 phosphate ester of polyalkoxylated fatty alcohol, commercially ble as Klearfac® AA-270 from BASF SE.

T5 alkoxylated linear, saturated 016-15 fatty alcohols containing 2 to 20 ethylenoxide 1O equivalents and 2 to 20 propyleneoxide equivalents.

T6 lauryl alcohol polyethersulfate containing 10 noxide equivalents, sodium salt.

T7 ethoxylated isotridecylalcohol containing 5 ethylenoxide equivalents.

T8 ethoxylated isotridecylalcohol ning 4 ethylenoxide equivalents.

T9 ethoxylated isotridecylalcohol ning 3 ethylenoxide equivalents.

T10 lated pentanol containing 4 noxide equivalents.

T1 1 Polyoxyethylen(20)—sorbitan—monolaurat. 2O The composition may comprise at least one surfactant, for example one, two or three surfactants.

In one embodiment, the composition comprises at least two ent surfactants. ably, the composition comprises one nonionic and one anionic surfactant, two different anionic surfactants, or two different nonionic surfactants.

Suitable examples for two ic surfactants are two alkoxylates, preferably two different alkanol alkoxylates.

Suitable examples of two c surfactants are one sulfonate and one phosphate, preferably one alkylarylsulfonate and one ate ester of alkoxylates, in particular one C8-13—alkylbenzylsulfonate and one phosphate ester of alkanol alkoxylates.

Suitable examples of one nonionic and one anionic surfactant are, in a first embodiment, one alkoxylate and one sulfonate, preferably one alkanol alkoxylate and one alkylarylsulfonate; in a second embodiment one alkylpolyglucoside and one sulfonate, preferably one C5-18—alkylpolyglucoside with a DP. of from 1.2 to 1.9 and one Ca—1a—alkylbenzylsulfonate. 40 The weight ratio of surfactant to alkoxylate is generally in the range of from 1:99 to 70:30, preferably in the range of from 5:95 to 50:50, especially preferably in the range PF 71968 of from 25:75 to 40:60.

In most cases, the composition comprises from 1 to 80% by weight (preferably from 3 to 50, especially preferably from 5 to 30 and in ular from 8 to 20% by weight) of the total of surfactant and alkoxylate.

The compositions according to the invention can furthermore also comprise adjuvants conventionally used for agrochemical formulations, the choice of the adjuvants depending on the specific use form, the type of formulation or the active substance.

Examples of suitable adjuvants are solvents, solid carriers, e-active substances (such as surfactants, lizers, tive colloids, wetters and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, optionally colorants and adhesives (for example for the treatment of seed) or conventional adjuvants for bait formulations (for example tants, feedants, bittering substances).

Suitable solvents are water or organic solvents such as mineral oil ons of medium to high boiling point such as kerosene and diesel oil, rmore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffins, ydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, l, propanol, butanol and cyclohexanol, s, ketones such as cyclohexanone, gamma— butyrolactone, dimethyl fatty acid amides, fatty acids and fatty acid esters, and strongly polar solvents, for e amines such as N—methylpyrrolidone. In principle, it is also possible to use solvent mixtures and es of the abovementioned solvents and water.

Solid carriers are mineral earths such as silicas, silica gels, tes, talc, kaolin, limestone, lime, chalk, bole, loess, clay, te, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and ble products such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders or other solid carriers.

Suitable thickeners are compounds which impart to the formulation a modified flow behavior, i.e. high viscosity at rest and low viscosity in the agitated state. Examples are polysaccharides, proteins (such as casein or gelatins), synthetic polymers, or inorganic layered minerals. Such thickeners are commercially available, for example Xanthan Gum (Kelzan®, CP Kelco, USA), Rhodopol® 23 (Rhodia, France) or Veegum® (R.T.

Vanderbilt, USA) or Attaclay® hard Corp., NJ, USA). The thickener content in the ation depends on the efficacy of the thickener. The skilled worker will choose 40 such a content that the desired viscosity of the formulation is obtained. The content will amount to from 0.01 to 10% by weight in most cases.

PF 71968 W0 2012/116939 26 Bactericides may be added in order to stabilize the composition. Examples of bactericides are those based on diclorophene and benzyl alcohol hemiformal and also isothiazolinone derivatives such as alkylisothiazolinones and benzoisothiazolinones (Acticide® MBS from Thor Chemie). Examples of suitable antifreeze agents are ethylene glycol, ene glycol, urea and glycerol. Examples of antifoams are silicone emulsions (such as, for example, Silikon® SRE, , Germany or Rhodorsi|®, Rhodia, France), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine nds and mixtures of these.

The composition according to the invention can preferably be t in the form of an emical formulation, water—soluble concentrates being preferred. Examples of formulations and their preparation are: i) Water—soluble concentrates (SL, LS): 10 parts by weight of the active substances are dissolved using 90 parts by weight of water or a water—soluble t.

Alternatively, wetters or other nts are added. Upon dilution in water, the active substance dissolves. This gives a ition with an active substance content of 10% by weight. ii) Dispersible concentrates (DC): 20 parts by weight of the active substances are 2O dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Upon dilution in water, a dispersion is obtained. The active substance content amounts to 20% by weight iii) Emulsifiable concentrates (EC): 15 parts by weight of the active nces are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzene— sulfonate and castor oil ethoxylate (in each case 5 parts by weight). Upon dilution in water, an emulsion is obtained. The composition has an active substance content of 15% by weight. iv) Emulsions (EW, EO, ES): 25 parts by weight of the active substances are dissolved in 35 parts by weight of xylene with on of calcium dodecylbenzene— ate and castor oil ethoxylate (in each case 5 parts by weight). Using an emulsifier (for example Ultra—Turrax), this mixture is placed into 30 parts by weight of water and made into a homogeneous emulsion. Upon dilution in water, an emulsion results. The composition has an active substance content of 25% by weight. v) Suspensions (SC, OD, FS): 20 parts by weight of the active nces are comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an organic solvent in a stirred—ball mill to give a finely divided active nce suspension. Upon dilution in water, a stable suspension of the active substance is obtained. The active substance content in the 40 composition amounts to 20% by weight. vi) Water—dispersible and water—soluble granules (WG, SG): 50 parts by weight of the active substances are ground finely with addition of 50 parts by weight of PF 71968 dispersants and wetters and formulated as water—dispersible or water—soluble es by means of technical apparatuses (for example extrusion, spray tower, fluidized bed). Upon dilution in water, a stable dispersion or solution of the active substance is obtained. The composition has an active substance content of 50% by weight. vii) dispersible and soluble powders (WP, SP, 88, WS): 75 parts by weight of the active substances are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants and wetters and also silica gel. Upon dilution in water, a stable dispersion or solution of the active substance is obtained. The 1O active substance content of the composition amounts to 75% by weight. viii) Gels (GP): in a ball mill, 20 parts by weight of the active substances, 10 parts by weight ofdispersant, 1 part by weight of gelling agent and 70 parts by weight of water or an c solvent are ground to give a fine suspension. Upon dilution with water, a stable suspension with an active nce content of 20% by weight is obtained. ix) Dusts (DP, DS): 5 parts by weight of the active substances are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dust with an active substance content of 5% by weight. x) Granules (GR, FG, GG, MG): 0.5 part by weight of the active substances is ground 2O finely and associated with 99.5 parts by weight of carriers. Conventional methods to this end are extrusion, spray—drying or the fluidized bed. This gives granules for direct application with an active nce content of 0.5% by weight. xi) ULV solutions (UL): 10 parts by weight of the active substances are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a composition to be applied directly with an active nce content of 10% by weight.

In l, the compositions comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the pesticides.

The user will generally use the ition according to the invention for use in a premetering device, in a knapsack sprayer, in a spray tank or in a spraying aircraft.

Here, the formulation is brought to the desired use concentration with a liquid, usually water and/or buffer, ally with addition of further auxiliaries, y the ready-to-use spray e (known as a tank mix) is obtained. Usually, 50 to 500 liters of the ready-to-use spray mixture are applied per hectare of utilizable agricultural area, preferably from 100 to 400 liters. In specific segments the amounts may also be above (e.g., fruit growing) or below (e.g., aircraft application) these amounts. In ic cases, such as, for example, aircraft application, it is also possible to use an organic solvent for making up the spray e, instead of water.

PF 71968 W0 2012/116939 28 2012/053230 The active substance concentrations in the ready—to—use preparations may be varied within substantial ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.

The concentration of the total of surfactant and alkoxylate in the ready—to—use preparation is in most cases in the range of from 0.01 to 50 g/I, preferably 0.08 to 10 g/I and in particular 0.5 to 8 g/I.

Oils of various types, wetters, drift reduction agents, stickers, Spreaders, adjuvants, 1O fertilizers, plant-strengthening products, trace ts, herbicides, bactericides, fungicides and/or pesticides may be added to the active substances or to the preparations comprising them, optionally also to the tank mix, immediately prior to use.

These products can be admixed to the compositions according to the ion in the weight ratio 1:100 to 100:1, preferably 1:10 to 10:1. Depending on the nature of the desired effect, the application rates of the active substance when used in plant protection are between 0.001 and 2.0 kg of active substance per ha, preferably between 0.005 and 2 kg per ha, especially preferably between 0.05 and 0.9 kg per ha, in particular between 0.1 and 0.75 kg per ha. 2O The application rate of the total of surfactant and alkoxylate is in most cases in the range of from 10 to 3000 g/ha, preferably from 10 to 1000 g/ha, ally preferably from 80 to 750 g/ha and specifically from 200 to 400 g/ha.

The present invention furthermore s to a concentrate sing the tant and the amine alkoxylate (A) or the quaternized derivative (AQ) of the amine alkoxylate (A). This concentrate is particularly suitable for use as an additive to the tank mix.

Suitable and preferred embodiments of the surfactant, the amine late (A) and the quaternized derivative (AQ) of the amine alkoxylate (A) are as mentioned above. The weight ratio of tant to alkoxylate is usually in the range of from 1:99 to 70:30, preferably in the range of from 5:95 to 50:50, especially preferably in the range of from :75 to 40:60. The concentrate may optionally comprise solvents such as water or organic solvents. The concentrate may optionally comprise adjuvants such as the abovementioned adjuvants.

The present invention furthermore relates to a method for the ation of the composition according to the ion by a) bringing the concentrate according to the invention and a pesticide into contact; b) by bringing the pesticide, the surfactant and the amine alkoxylate (A) or the 40 quaternized derivative (AQ) of the amine late (A) into t.

In a preferred embodiment, the method is a method of preparing a tank mix comprising PF 71968 W0 2012/116939 29 the composition, by bringing the surfactant into contact with a mixture sing the pesticide and the amine alkoxylate. In most cases, the e is an s e (such as a tank mix) which may comprise customary formulation auxiliaries. Here, the surfactant may be added in pure form or else in the form of a dilution in water or organic solvents. Further customary formulation auxiliaries can likewise be added, in addition to the surfactant. Further pesticides may also be added to the tank mix, such as at least one herbicide (for example glyphosate) and/or at least one insecticide and/or one fungicide (for example pyraclostrobin).

The present invention furthermore relates to a use of a surfactant for addition to a mixture (such as a tank mix) comprising the pesticide and the amine alkoxylate. The surfactant is ably added in order to increase the biological activity of the pesticide.

The present invention rmore s to a method of controlling phytopathogenic fungi and/or undesired vegetation and/or undesired insect or mite attack and/or for regulating the growth of plants, wherein the composition according to the invention is allowed to act on the respective pests, their environment or the plants to be protected from the tive pest, on the soil and/or on undesirable plants and/or the crop plants and/or their environment.

Examples of suitable crop plants are cereals, for example wheat, rye, barley, triticale, oats or rice; beet, for example sugar or fodder beet; pome fruit, stone fruit and soft fruit, for example apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, currants or gooseberries; legumes, for example beans, lentils, peas, |ucerne or ns; oil crops, for example oilseed rape, mustard, olives, sunflowers, t, cacao, castor beans, oil palm, peanuts or ns; cucurbits, for example pumpkins/squash, cucumbers or melons; fiber crops, for example cotton, flax, hemp or jute; citrus fruit, for example oranges, lemons, grapefruit or ines; vegetable plants, for example spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, pumpkin/squash or capsicums; plants of the laurel family, for example avocados, cinnamon or camphor; energy crops and industrial feedstock crops, for example maize, soybeans, wheat, d rape, sugar cane or oil palm; maize; tobacco; nuts; coffee; tea; bananas; wine (dessert grapes and grapes for vinification); hops; grass, for e turf; sweetleaf (Stevia rebaudania); rubber plants and forest plants, for example flowers, shrubs, deciduous trees and rous trees, and propagation material, for example seeds, and harvested produce of these plants.

The term crop plants also includes those plants which have been modified by ng, mutagenesis or recombinant methods, including the biotechnological agricultural 40 products which are on the market or in the process of being developed. cally modified plants are plants whose genetic material has been modified in a manner which does not occur under natural conditions by hybridizing, mutations or natural PF 71968 W0 2012/116939 30 recombination (i.e. recombination of the genetic al). Here, one or more genes will, as a rule, be integrated into the genetic material of the plant in order to improve the plant’s properties. Such recombinant modifications also se posttranslational modifications of proteins, oligo— or polypeptides, for example by means of glycosylation or binding polymers such as, for example, prenylated, acetylated or farnesylated residues or PEG residues.

Examples which may be mentioned are plants which, as the result of plant-breeding and recombinant measures, have acquired a tolerance for certain classes of 1O ides, such as yphenylpyruvate enase (H PPD) inhibitors, acetolactate synthase (ALS) inhibitors such as, for example, sulfonylureas (EP—A 257 993, US 5,013,659) or imidazolinones (for example US 6,222,100, WO 01/82685, WO 00/26390, WO 18, WO 26, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073), enolpyruvylshikimate 3—phosphate synthase (EPSPS) inhibitors such as, for example, sate (see, for example, WO 92/00377), glutamine synthetase (GS) inhibitors such as, for example, glufosinate (see, for example, EP—A 242 236, EP—A 242 246) or oxynil herbicides (see, for example, US 5,559,024). For example, breeding and nesis have given rise to Clearfield® oilseed rape (BASF SE, Germany), which 2O features tolerance for imidazolinones, for example imazamox. With the aid of recombinant methods, crop plants such as soybeans, , maize, beet and oilseed rape have been generated which are resistant to glyphosate or glufosinate, and these are available by the brand names RoundupReady® (glyphosate—resistant, Monsanto, U.S.A.) and Liberty Link® (glufosinate—resistant, Bayer ience, Germany).

Also comprised are plants which, with the aid of recombinant measures, produce one or more toxins, for example those from the bacterial strain Bacillus. Toxins which are produced by such genetically modified plants comprise, for e, insecticidal proteins of Bacillus spp., in particular from B. thuringiensis, such as the endotoxins , Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry38b1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetable insecticidal proteins (VIPs), for example VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins from nematode—colonizing bacteria, for example Photorhabdus spp. or Xenorhabdus spp.; toxins from animal organisms, for e wasp, spider or scorpion toxins; fungal , for example from Streptomycetes; plant lectins, for example from pea or barley; agglutinins; proteinase inhibitors, for e trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome—inactivating proteins (RlPs), for example ricin, maize RIP, abrin, luffin, saporin or bryodin; steroid—metabolizing enzymes, for example oxysteroid oxidase, ecdysteroid IDP glycosyl erase, cholesterol oxidase, ecdysone inhibitors 40 or HMG ductase; ion channel blockers, for example inhibitors of sodium or calcium channels; juvenile e esterase; receptors for the diuretic hormone (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases and PF 71968 W0 2012/116939 31 ases. These toxins can also be produced, in the plants, in the form of pretoxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are distinguished by a novel combination of different protein domains (see, for example, WO 2002015701). Further examples of such toxins or genetically d plants which produce these toxins are disclosed in EP—A 374 753, WO 93/07278, WO 95/34656, EP—A 427 529, EP—A 451 878, WO 03/18810 and WO 03/52073. The methods for generating these cally modified plants are known to the skilled worker and explained, for example, in the abovementioned ations. A large number of the abovementioned toxins impart to the plants which produce them a tolerance for pests from all taxonomic classes of the arthropods, in particular beetles (Coeleropta), dipterans (Diptera) and lepidopterans optera) and nematodes (Nematoda). Genetically modified plants which produce one or more genes which code for insecticidal toxins are described for example in the abovementioned publications and are in some cases commercially available such as, for e, YieldGard® (maize varieties which produce the toxin Cry1Ab), YieldGard® Plus (maize varieties which produce the toxins Cry1Ab and Cry3Bb1), Starlink® (maize varieties which produce the toxin Cry9c), ex® RW (maize varieties which produce the toxins Cry34Ab1, b1 and the enzyme phosphinothricin yltransferase [PAT]); NuCOTN® 338 (cotton varieties which produce the toxin ), Bollgard® l (cotton varieties which produce the toxin Cry1Ac), Bollgard® || (cotton varieties which produce the toxins Cry1Ac and Cry2Ab2); VIPCOT® (cotton varieties which produce a VIP ; NewLeaf® (potato varieties which produce the toxin Cry3A); Bt—Xtra®, NatureGard®, KnockOut®, rd®, Protecta®, Bt11 (for example Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (maize varieties which produce the toxin Cry1Ab and the PAT enzyme), MIR604 from Syngenta Seeds SAS, France (maize varieties which produce a modified version of the toxin Cry3A, see in this context WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (maize varieties which produce the toxin Cry3Bb1), IPC 531 from Monsanto Europe S.A., m (cotton varieties which produce a modified version of the toxin Cry1Ac) and 1507 from Pioneer Overseas Corporation, Belgium (maize varieties which produce the toxin Cry1 F and the PAT enzyme).

Also comprised are plants which, with the aid of recombinant measures, produce one or more proteins which bring about an increased resistance to, or ability to withstand, bacterial, viral or fungal pathogens such as, for example, so-called pathogenesis- related ns (PR proteins, see EP—A O 392 225), resistance proteins (for example potato varieties which produce two resistance genes against Phytophthora infestans from the Mexican wild potato So/anum bu/bocastanum) or T4 me (for example potato varieties which, as the result of the production of this protein, are resistant to 40 bacteria such as a amy/vora).

PF 71968 W0 2012/116939 32 Also comprised are plants whose productivity has been improved with the aid of recombinant methods, for example by increasing the yield potential (for example biomass, grain yield, starch content, oil content or n content), the tolerance for drought, salt or other limiting environmental factors, or the resistance to pests and fungal, bacterial and viral ens.

Also comprised are plants whose constituents, in particular for improving human or animal nutrition, have been modified with the aid of recombinant methods, for example by oil plants producing health-promoting long—chain omegafatty acids or monounsaturated omegafatty acids (for example Nexera® oilseed rape, DOW Agro Sciences, Canada).

The present invention also relates to seed (such as seeds or other plant propagation materials) sing the ition according to the invention. Plant propagation materials can be treated preventively with the composition according to the invention at the point of or even before sowing or at the point of or even before transplanting. For the treatment of seed, one will generally use water—soluble concentrates (LS), suspensions (FS), dusts (DS), water—dispersible and water—soluble powders (WS, SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF). These compositions can be applied to the propagation materials, in particular seed, in undiluted form or, 2O preferably, in diluted form. Here, the composition in question can be diluted 2— to —fold, so that from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, of active substance is present in the compositions used for the seed dressing. The application may be effected before or during . The treatment of plant propagation material, in ular the ent of seed, is known to the skilled worker and carried out by dusting, coating, pelleting, dipping or soaking the plant ation material, the treatment ably being d out by pelleting, coating and g or by in—furrow treatment so that, for example, untimely early germination of the seed is ted. It is preferred to use suspensions for the treatment of seed. Usually, such compositions comprise from 1 to 800 g/l of active substance, from 1 to 200 g/I of surfactants, from 0 to 200 g/l of antifreeze , from 0 to 400 g/l of binders, from 0 to 200 g/l of colorants and solvent, preferably water.

The advantages of the ion are high stability of the formulation and of the spray mixture, little wind-caused drift in the case of spray applications, good adhesion of the formulation on the surface of the treated plants, increased solubility of the pesticides in the formulation, sed tion of the pesticides into the plant and, as a result, more rapid and enhanced activity. An ant advantage is the low toxicity of the alkoxylates, in particular the low aquatic toxicity. Another advantage is the low harmful effect against crop plants, i.e., low phytotoxic effects. A further advantage is the simple 40 handling of these alkoxides since, for example, no gelling takes place upon their oration into formulations. Another advantage is that no phase separation and no salt precipitation occurs in compositions with a high salt content, such as over 400 g/l PF 71968 W0 2012/116939 33 2012/053230 glyphosate; but the alkoxylates are highly compatible with surfactants, specifically anionic surfactants.

Another important advantage is that the invention permits the stable formulation of anionic, H—acidic pesticides in the presence of cationic surfactants. This was particularly surprising since usually the precipitation of salts may occur in compositions which comprise anionic and cationic compounds, for example during e, in the spray mixture or in r dilution.

The es which follow illustrate the invention t imposing any limitation.

Examples Surfactant A: C10.13—alkylbenzenesulfonate, free acid. tant B: Phosphate ester of —alkanol alkoxylate, the alkoxylate being composed of ethylene oxide and/or ene oxide, and having a mean number of alkoxide units in the range of from 12 to 18.

Surfactant C: Cum—alkanol alkoxylate, the alkoxylate being composed of ethylene oxide and propylene oxide, and having a mean number of alkoxide units in the range of from 17 to 26. 2O Surfactant D: iso—C13—alkanol alkoxylate, the alkoxylate being composed of ethylene oxide and having a mean number of alkoxide units in the range of from 4.5 to 8.

Surfactant E: C1o—guerbet alkanol alkoxylate, the alkoxylate being composed of ethylene oxide and having a mean number of alkoxide units in the range of from 2.5 to 6.

Surfactant F: C4-3—alkanol alkoxylate, the alkoxylate being composed of ethylene oxide and having a mean number of alkoxide units in the range of from 3.5 to 7.

Surfactant G: Fatty acid mixture comprising 50—60% dodecanoic acid and 20—30% of C14—alkanolic acid, and further C10-1a—alkanoic acids, acid number 250—260.

Surfactant H: 08.1o—alkylpolyglucoside, D.P. 1.7.

Example 1 — Preparation of amine alkoxylate A First, 2—propylheptylamine was prepared starting from 2—propylheptanol and ammonia, as described in Example 1 of . 40 Then 1280 g (8.15 mol) of the 2—propylheptylamine were admixed with 40 g of water.

Then, after flushing with nitrogen, at 100°C, 717 g (16.3 mol) of ethylene oxide were metered in (2 bar, 16 h). Subsequently, at 90°C, ing traces of ethylene oxide PF 71968 were d under reduced pressure. This gave a quantitative yield with an amine number of 229 mg KOH/g. In the next step, 821.5 g (3.35 mol) of this precursor product were d with 8.0 g of 50% strength KOH and dewatering was carried out at 90°C under reduced pressure. Afterflushing with nitrogen, at 120°C, 1179 g (= 26.8 mol) of ne oxide were metered in (1.5 bar, 12 h). This gave a quantitative yield of the yellowish low—viscosity, liquid amine—alkoxylate A.

Example 2 — Amine alkoxylate + surfactant A For the ouse tests, winter wheat (cultivar Cubus) and soybean (cultivar Oxford) 1O were sown or potted in loamy sandy soil to a depth of 1-2 cm. When the plants had reached a growth height of 10 to 25 cm (i.e., around 10 to 21 days after sowing), the spray mixtures were applied to the plants in a spraying cabin.

A trated formulation comprising glyphosate isopropylammonium in solution in water comprising the tants stated and amine alkoxylate A from Example 1 was diluted with zed water and applied at a water application rate of 375 l/ha (140 g or 280 g of glyphosate/ha). The temperatures in the experimental period were n 18—35°C. During this time, the experimental plants received optimum watering, with nutrients being supplied via the water used for watering.

The herbicidal activity was evaluated by awarding scores to the treated plants (four each time) in ison to the untreated control plants. The evaluation scale ranges from 0% to 100% activity. 100% activity means the complete death at least of those parts of the plant that are above ground. Conversely, 0% activity means that there were no differences between treated and untreated .

The results in Tables 1 demonstrate the increased activity of the active substance as a result of addition of the amine alkoxylate in admixture with surfactant.

Table 1A: Efficacy after 21 days at 140 g/ha glyphosate Amine alkoxylate/surfactant Winter wheat Soybean efficacy efficacy W [%] ———— Amineankoxwaw euactantArr> Amine alkoxylate A + surfactant A 255 + 45 “— a) not according to the invention PF 71968 W0 2012/116939 35 Table 1B: Efficacy after 21 days at 280 g/ha glyphosate Amine alkoxylate/surfactant Winter wheat Soybean efficacy efficacy Without a) Amine alkoxylate A a) Surfactant A a) Amine late A + surfactant A 25500+ 45 a)not according to the invention Table 10: Efficacy after 21 days at 140 g/ha sate Amine alkoxylate/surfactant Winter wheat Soybean efficacy efficacy [%] [%] Amine alkoxylate A a) Amine late A + surfactant A 3500+050“— a) not according to the invention Table 1D: Efficacy after 21 days at 280 g/ha glyphosate Amine alkoxylate/surfactant Winter wheat Soybean efficacy efficacy Amine alkoxylate A a) _ Amine alkoxylate A + surfactant A 350 + 50 a) not according to the invention Example 3 — Amine alkoxylate + surfactant A + tant B The experiments were carried out as in Example 2 and the results are ed in Table 2.

Table 2A: Efficacy after 21 days at 140 g/ha glyphosate Amine alkoxylate/surfactant Winter wheat n efficacy efficacy []% [‘70] Amine alkoxylate A a ——_ Surfactantw ——— Amine alkoxylate A + surfactant A + 250 + 50 + 100 81 61 surfactant B a) not according to the invention PF 71968 W0 2012/116939 36 Table 2B: Efficacy after 21 days at 280 g/ha glyphosate Amine alkoxylate/surfactant Winter wheat Soybean efficacy efficacy a) not ing to the invention Example 4 — Amine late + surfactant A + surfactant C The experiments were carried out as in Example 2 and the results are compiled in Table 3.

Table 3A: Efficacy after 21 days at 140 g/ha glyphosate Amine alkoxylate/surfactant Winter wheat Soybean efficacy efficacy eurractantca> Amine alkoxylate A + surfactant A + 250 + 50 + 100 78 surfactant C a) not according to the invention Table 3B: Efficacy after 21 days at 280 g/ha glyphosate Amine alkoxylate/surfactant Winter wheat Soybean cy efficacy ———m- Amine alkoxylate A + surfactant A + 250 + 50 + 100 93 84 tant C a) not according to the invention PF 71968 Example 5 — Amine alkoxylate + surfactant A + surfactant D The ments were carried out as in Example 2 and the results are compiled in Table 4.

Table 4A: Efficacy after 21 days at 140 g/ha glyphosate Amine late/surfactant Winter wheat Soybean efficacy efficacy W [%] Amineankoxwaw ———m_ Amine alkoxylate A + surfactant A + 200 + 50 + 50 88 75 surfactant D a) not according to the invention Table 4B: Efficacy after 21 days at 280 g/ha glyphosate Amine alkoxylate/surfactant Winter wheat Soybean efficacy efficacy W [%] Amine alkoxylate A + surfactant A + 200 + 50 + 50 91 85 surfactant D 1O a) not according to the ion Example 6 — Amine alkoxylate + surfactant A + surfactant E The experiments were carried out as in Example 2 and the results are compiled in Table 5.

Table 5A: Efficacy after 21 days at 140 g/ha glyphosate Amine alkoxylate/surfactant Winter wheat Soybean efficacy cy [%] [%] nkoxwaw Amine alkoxylate A + surfactant A + 200 + 50 + 50 81 surfactant E a) not according to the invention PF 71968 W0 2012/116939 38 Table SB: y after 21 days at 280 g/ha glyphosate Amine alkoxylate/surfactant Winter wheat Soybean efficacy efficacy W 300 Amine alkoxylate A + surfactant A + 200 + 50 + 50 83 surfactant E a) not according to the ion Example 7 — Amine alkoxylate + surfactant E + surfactant F The experiments were carried out as in Example 2 and the results are ed in Table 6.

Table 6A: Efficacy after 21 days at 140 g/ha glyphosate Amine alkoxylate/surfactant Winter wheat Soybean efficacy efficacy Suacrranw Amine alkoxylate A + surfactant E + surfactant F a) not according to the invention Table SB: Efficacy after 21 days at 280 g/ha glyphosate Amine alkoxylate/surfactant Winter wheat Soybean efficacy efficacy [%l W SurfactantFa> ——-zu Amine late A + surfactant E + 200 + 50 + 50 92 surfactant F a) not according to the invention PF 71968 W0 2012/116939 39 Example 8 — Amine alkoxylate + surfactant A + surfactant G The experiments were carried out as in e 2 and the results are ed in Table 7.

Table 7A: Efficacy after 21 days at 140 g/ha glyphosate Amine late/surfactant Winter wheat Soybean efficacy efficacy []% [‘70] Amine alkoxylate A a Amine alkoxylate A + surfactant A + —8—_250 + 50 + 100 surfactant G a)not according to the ion Table 7B: Efficacy after 21 days at 280 g/ha glyphosate Amine alkoxylate/surfactant Winter wheat Soybean efficacy efficacy [%] []% Amine alkoxylate A a> Amine late A + surfactant A + ——:“250 + 50 + 100 surfactant G a) not ing to the invention Example 9 — Stability test An aqueous solution composed of 480 g/I glyphosate isopropylamine salt, 225 g/I amine alkoxylate A and 75 g/I surfactant H was stored for four weeks, either at —5°C or +55°C. No phase separation occurred.

By way of ison, an aqueous solution composed of 480 g/I of glyphosate isopropylamine salt and 300 g/I of Genamine® T 150 (Cums—amine ethoxylate having 2O 15 E0 units, commercially available from Clariant) was stored correspondingly. A clear phase separation into an aqueous bottom phase with glyphosate salt and a top phase with Genamine® T150 occurred.

By way of further comparison, an aqueous solution composed of 480 g/l of glyphosate isopropylamine salt, 150 g/I of ne® T 150 and 150 g/l surfactant H was stored correspondingly. Likewise, a clear phase separation into an aqueous bottom phase with glyphosate salt and a top phase with Genamine® T150 occurred.

Claims (22)

We claim:

1. A composition comprising a pesticide, a surfactant and an late, wherein the alkoxylate is an amine alkoxylate (A) or a quaternized derivative (AQ) 10 of the amine alkoxylate (A), where R1, R2, and R5 ndently of one another are ethylene, propylene, butylene or a mixture of these, R3 is an H, -OH, -OR4, -[R5-O]p-R6, C1-C6-alkyl or an oxygen anion, R4 is a C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, 15 R6 is an H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, -SO3Ra, -P(O)ORbORc, -CH2CO2Rd, or -C(O)Re, R7 is 2-propylheptyl, Ra and Rd independently of one another are an H, inorganic or organic cations, Rb and Rc independently of one another are an H, nic or organic cations, 20 C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, Re is C1-C22-alkyl, C2-C22-alkenyl, C2-C22-alkynyl, C6-C22-aryl or C7-C22-alkylaryl n, m and p independently of one another have a value of from 1 to 30, A- is an agriculturally acceptable anion, or, if R3 is an oxygen anion, A- is 25 absent.

2. The composition according to claim 1, wherein the surfactant is an c tant comprising an anionic group, which is a sulfonate, sulfate, phosphate or carboxylate; and/or a nonionic surfactant, which is a based surfactant or 30 an alkanol late.

3. The composition ing to claim 1 or 2, wherein the weight ratio of surfactant to alkoxylate is in the range of from 1:99 to 70:30. 35

4. The composition according to any of claims 1 to 3, wherein the composition comprises from 1 to 80% by weight of the total of surfactant and alkoxylate.

5. The composition according to any of claims 1 to 4, wherein the composition comprises at least two ent surfactants.

6. The composition according to any of claims 1 to 5, n at least one surfactant is ed among the following surfactants: a) a C16-18 -alkanol alkoxylate, where the late is composed of ethylene oxide and/or propylene oxide, and the alkanol alkoxylate has a mean 5 number of alkoxide units in the range of from 12 to 35; b) a C10 –guerbet alkanol alkoxylate, where the alkoxylate is composed of ethylene oxide and the alkanol alkoxylate has a mean number of alkoxide units in the range of from 2 to 8; c) an 3 -alkanol late, where the alkoxylate is composed of ethylene 10 oxide and the alkanol alkoxylate has a mean number of alkoxide units in the range of from 3 to 10; d) a C4alkanol alkoxylate, where the alkoxylate is composed of ethylene oxide and the alkanol alkoxylate has a mean number of alkoxide units in the range of from 2 to 9; 15 e) a C8-10 -alkylpolyglucoside, with a D.P. of from 1.4 to 1.9; f) a C8-14 -alkylbenzenesulfonate; and g) a phosphate ester of C8-14 -alkanol alkoxylates.

7. The composition according to any of claims 1 to 5, wherein the pesticide is 20 glyphosate and the at least one surfactant is selected among a C8-10 - alkylpolyglucoside, with a D.P. of from 1.4 to 1.9.

8. The composition according to any of claims 1 to 5, wherein the pesticide is glyphosate and the at least one surfactant is selected among a C8-14 - 25 alkylbenzenesulfonate.

9. The composition according to any of claims 1 to 5, wherein at least one tant is a C6alkylpolyglucoside. 30

10. The composition according to any of claims 1 to 9, wherein R1, R2 and R5 independently of one another are ethylene, ethylene and propylene, ne and butylene, or ethylene, propylene and ne.

11 The composition according to any of claims 1 to 10, wherein the pesticide is a 35 pesticide with at least one H-acidic group or an anionic salt of the pesticide with at least one H-acidic group.

12. The composition according to any of claims 1 to 11, wherein, in the amine alkoxylate (A), the total of n and m is from 2 to 40, and in its quaternized 40 derivative (AQ) the total of n, m and p is from 3 to 80.

13. The composition according to any of claims 1 to 12, wherein R3 is an H.

14. The composition ing to any of claims 1 to 13, wherein the pesticide comprises a pesticide with at least one ic group. 5

15. A concentrate sing the surfactant according to any of claims 1 to 14 and the amine alkoxylate (A) or the quaternized derivative (AQ) of the amine alkoxylate (A) according to any of claims 1 to 12.

16. A method of preparing the composition according to any of claims 1 to 12, by 10 bringing the concentrate according to claim 13 and a pesticide into contact; or by bringing the pesticide, the surfactant and the amine alkoxylate (A) or the quaternized derivative (AQ) of the amine alkoxylate (A) into contact.

17. The use of a surfactant according to any of claims 1 to 12 for addition to a 15 mixture comprising the pesticide according to any of claims 1 to 12 and the amine alkoxylate according to any of claims 1 to 12.

18. A method of controlling phytopathogenic fungi and/or undesired vegetation and/or undesired insect or mite attack and/or for regulating the growth of plants, 20 wherein the composition according to any of claims 1 to 12 is allowed to act on the respective pests, their environment or the plants to be protected from the respective pest, on the soil and/or on undesired plants and/or the crop plants and/or their environment. 25

19. Seed, comprising the composition according to any of claims 1 to 12.

20. A composition according to claim 1, substantially as herein bed with reference to any one of the accompanying examples thereof. 30

21. A trate according to claim 15, substantially as herein bed with reference to any one of the anying examples thereof.

22. A method according to claim 16 or claim 18, substantially as herein described with reference to any one of the accompanying examples thereof.