WO2011101303A2 - Compound comprising a pesticide and an alkoxylate of isoheptadecylamine - Google Patents

Abstract

The invention relates to a compound comprising a pesticide and an alkoxylate. The invention further relates to the alkoxylate, to a method for the production thereof, and to the use thereof as an additive in spray mixtures containing pesticides. The invention further relates to a method for combating phytopathogenic fungi and/or undesired plant growth and/or undesired insect or mite infestation and/or for regulating the growth of plants. The compound can be applied onto the respective pests, the habitat thereof or the plants that are to be protected from the respective pest, the soil and/or onto undesired plants and/or the useful plants and/or the habitat thereof. The invention further relates to seeds containing the compound.

Description

 A composition comprising a pesticide and an alkoxylate of isoheptadecylamine

The present invention is a composition comprising a pesticide and an alkoxylate. Moreover, the invention relates to the alkoxylate, a process for its preparation, and its use as auxiliaries in pesticide-containing spray liquors. The invention further relates to a method for controlling phytopathogenic fungi and / or undesired plant growth and / or undesired insect or Mi Iben infestation and / or for the regulation of the growth of plants, wherein the composition of the respective pests, their habitat or the plants to be protected from the respective pest, the soil and / or undesirable plants and / or the crops and / or their habitat. Furthermore, the invention relates to seed containing the composition. Combinations of preferred features with other preferred features are encompassed by the present invention.

Alkoxylates and their use in agrochemical formulations as adjuvants are well known:

WO 2009/004044 discloses a herbicidal composition comprising a phenoxyacid herbicide and an alkoxylated alkylamine as adjuvant.

US 5,668,085 discloses a herbicidal composition comprising an aqueous solution of glyphosate and surfactant. The surfactant may be an alkoxylated alkylamine wherein the alkyl group contains from 8 to 22 carbon atoms.

WO 2001/97614 discloses herbicidal compositions comprising a herbicide and a surfactant, which may be, for example, an alkoxylated alkylamine.

Alkoxylated alkylamines, in particular commercially available ethoxylated tallow fatty amines (POEA), have critical toxic (such as skin and eye irritation) and ecotoxic properties (such as high ecotoxicity against aquatic organisms such as algae and daphnia). Thus, for example, the POEA (CAS No. 61791-26-2) often used as wetting agent in Roundup® herbicides is considered to be relatively aquatoxic (Tsui and Chu, Chemosphere 2003, 52, 1 189-1 197).

The object of the present invention was therefore to find an adjuvant which is well suited for herbicides such as glyphosate and is less toxic (less toxic at first). Furthermore, the adjuvant should allow a storage stable formulation of the pesticides.

The object is achieved by a composition comprising a pesticide and an alkoxylate, wherein the alkoxylate is an amine alkoxylate (A)

or a quaternized derivative (AQ)

the Aminalkoxylats (A), wherein

R ^{1 is} a branched, aliphatic alkyl radical C17H35,

R ² , R ³ , and R ^{7 are} independently ethylene, propylene, butylene, or a mixture thereof,

R ^{4 is} H, -OH, -OR ⁶ , - [R ⁷ -O] _p -R ⁵ , C ₁ -C ₆ -alkyl or an oxygen anion,

R ^{5 is} H, dC ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, -SO ₃ R ^a , -P (O) OR ^b OR ^c ,

-CH ₂ C0 ₂ R ^d , or -C (O) R ^e

R ⁶ is a Ci-C ₆ alkyl, C ₂ -C ₆ alkenyl, or C ₂ -C ₆ alkynyl,

R ^a and R ^d independently of one another denote an H, inorganic or organic cation, R ^b and R ^c independently of one another denote an H, inorganic or organic cation,

C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl,

R ^e d C ₂₂ alkyl, C ₂ -C ₂₂ alkenyl, C ₂ -C ₂₂ alkynyl, C ₆ -C ₂₂ aryl, C ₇ -C ₂₂ alkylaryl, n, m and p independently of one another have a value of 1 to 30, and

A- is an agriculturally acceptable anion or, if R ^{4 is} an oxygen anion, A- is not present. The composition according to the invention preferably comprises a pesticide and an alkoxylate, the alkoxylate being an amine alkoxylate (A).

The radical R ¹ is a branched, aliphatic alkyl radical C17H35. Preferably, R ¹ comprises several different, branched, aliphatic Ci7H3sAlkylreste. The average degree of branching of R ¹ is usually from 2.8 to 3.7, preferably from 2.9 to 3.6, more preferably from 3.01 to 3.5, very particularly preferably from 3.05 to 3.4, and for example about 3 ,1 .

The term "degree of branching" is hereby defined in a manner known in principle as the number of methyl groups in a molecule of the alcohol minus 1. The mean degree of branching is the statistical average of the degrees of branching of all molecules of a sample The radical R ^{1 used can} be a mixture of different alkyl groups C 17 H 35. Accordingly, the alcohol R ¹ -OH used as starting material for the synthesis can be a mixture of different alcohols.

The average degree of branching can be determined as follows ¹ H-NMR spectroscopy: For this purpose, a sample of the alcohol R ¹ -OH first with a derivatization with Trichloroacetyl isocyanate (TAI) subjected. The alohol is converted into the carbamic acid esters. The signals of the esterified primary alcohols are at δ = 4.7 to 4.0 ppm, those of the (if present) esterified secondary alcohols at about 5 ppm and water present in the sample reacts with TAI to carbamic acid. All methyl, methylene and methine protons are in the range of 2.4 to 0.4 ppm. The signals <1 ppm are assigned to the methyl groups. From the spectrum thus obtained, the average degree of branching (iso-index) can be calculated as follows:

Iso Index = ((F (CH ₃ ) / 3) / (F (CH ₂ -OH) / 2)) - 1 where F (CH ₃ ) is the signal surface corresponding to the methyl protons and F (CH ₂ -OH) is the signal surface the methylene protons in the Ch -OH group.

N preferably has a value of from 1 to 20, particularly preferably from 1 to 15. m preferably has a value of from 1 to 20, more preferably from 1 to 15. p preferably has a value of from 1 to 30, particularly preferably from 1 to 20 The values of n, m and o are usually average values, as they usually arise in the alkoxylation with alkoxides. Therefore, n, m, and o can take both integer values and all values between integers.

In the case of the amine alkoxiate (A), the sum of n and m is preferably from 2 to 40, and its quaternized derivative (AQ) is the sum of n, m and p is from 3 to 80.

In the case of aminalkoxiate (A), the sum of n and m is particularly preferably 3 to 30, and especially 5 to 25. In another particularly preferred embodiment, the sum of n and m is 6 to 9, in particular 6.5 to 8.5 and in particular 6.9 to 7.9. In another particularly preferred embodiment, the sum of n and m is 1 to 40, in particular 12 to 30 and in particular 13.5 to 25. In the quaternized derivative (AQ) of Aminalkoxiat (A) is the sum of n, m and p more preferably 3 to 40, and especially 5 to 25.

R ² , R ³ and R ⁷ are preferably independently of one another ethylene, ethylene and propylene, ethylene and butylene, or ethylene, propylene and butylene. In a further preferred embodiment, R ² , R ³ and R ^{7 are} propylene. In a further preferred embodiment, R ² , R ³ and R ^{7 are} butylene. More preferably, R ² , R ³ and R ^{7 are} independently of each other ethylene, or ethylene and propylene. Most preferably, R ² , R ³ and R ^{7 are} ethylene. If R ² , R ³ or R ⁷ contain a butylene radical, this can be described as n-butylene, iso-

Butylene, or 2,3-butylene group, with n-butylene and iso-butylene being preferred and n-butylene being most preferred. R ² , R ³ , and R ⁷ may independently be a mixture of ethylene, propylene, or butylene. In this case, for example, one or all radicals R ² , R ³ , and R ⁷ each contain in a Alkoxiyatkette a mixture of these groups. Such mixtures may be linked together in any order, for example randomly or in block fashion (such as one block of ethylene and one block of propylene). It is also possible in each case one or more of the radicals R ^2, R ^3, and R be constructed a complete Alkoxiyatkette from different alkylene groups. ⁷ For example, R ² and R ^{3 may be} composed of ethylene and R ^{7 may be} composed of propylene.

R ⁴ is preferably an H, OH, C 1 -C ⁴ alkyl or an oxygen anion, more preferably it is H, methyl, butyl or an oxygen anion. In a particularly preferred embodiment, R ^{4 is} a methyl. In another particularly preferred embodiment, R ^{4 is} an oxygen anion. In another particularly preferred embodiment, R ^{4 is} H.

R ⁵ is preferably an H or C ₁ -C ₆ -alkyl, particularly preferably an H or methyl, in particular H. R ⁶ is preferably a C ₁ -C ₆ -alkyl, such as methyl.

R ^a and R ^d are independently H, or inorganic or organic cations, which may be mono- or poly-positively charged. Examples of inorganic cations are cations of ammonium, Na ⁺ , K ⁺ , Mg ⁺ , Ca ²⁺ , or Zn ²⁺ . Examples of organic cations are methylammonium, dimethylammonium, trimethylammonium, tetramethylammonium, (2-hydroxyethyl) ammonium, bis (2-hydroxyethyl) ammonium, tris (2-hydroxyethyl) ammonium, tetra (2-hydroxyethyl) ammonium. Preferably, R ^a and R ^d are independently H, or inorganic cations. If an inorganic or organic cation is present, then the associated anionic group would be formed from the corresponding functional group (eg, -SO 3 ^" , -Ρ (O) ΟΌ ^" , or -CH 2 CO 2 ^" ) on R ⁶ .

R ^b and R ^c are preferably independently H, inorganic or organic cations. Suitable inorganic or organic cations are those mentioned under R ^a .

In a further embodiment, in the quaternary derivative (AQ), the radicals R ^a , R ^b , R ^c and R ^{d may} independently be organic cations, the cationic group being the quaternary nitrogen cation of AQ itself. Thus, AQ could thus form a zwitterion, the anionic group being formed by the corresponding functional group (eg -SO 3 -, -Ρ (O) ΟΌ ^" , or -CH ₂ CO ₂ -) on R ⁶ in AQ, and the cationic one Group of the quaternary nitrogen of AQ. In this zwitterion A form of AQ is the presence of an agriculturally acceptable anion A- optional.

R ^e is preferably C 1 -C 12 -alkyl, C 6 -C 12 -aryl, or C 7 -C 12 -alkylaryl, particularly preferably C 1 -C 6 -alkyl.

A- is an agriculturally acceptable anion, as well known to those skilled in the art. Preferably, A is a halide (such as chloride or bromide), phosphate, sulfate or an anionic pesticide. Propionate, acetate or formate are also suitable as A-. A- is particularly preferably an anionic pesticide, such as glyphosate anion or glufosinate anion. If R ^{4 is} an oxygen anion, an amine oxide is present. In this case, another anion such as A- is not present.

In the case of the amine alkoxylate (A), R ² and R ³ are preferably each independently ethylene, ethylene and propylene, ethylene and butylene, or ethylene, propylene and butylene, and the sum of n and m is 2 to 60, preferably 2 to 40, particularly preferred 3 to 30, and especially 5 to 25. In another preferred embodiment, R ² and R ^{3 are} ethylene, ethylene and propylene, ethylene and butylene, or ethylene, propylene and butylene and the sum of n and m is 6 to 9, especially 6 , 5 to 8.5 and in particular 6.9 to 7.9. In a further preferred embodiment, R ² and R ^{3 are} ethylene, ethylene and propylene, ethylene and butylene, or ethylene, propylene and butylene and the sum of n and m 1 1 to 40, in particular 12 to 30 and in particular 13.5 to 25 In a particularly preferred embodiment, R ¹ and R ^{2 are} ethylene, ethylene and propylene, ethylene and butylene, or ethylene, propylene and butylene and the sum of n and m is 6 to 14, in particular 8 to 12 and in particular 9 to 1 1 .

In the case of the amine alkoxylate (A), R ² and R ³ are particularly preferably ethylene, and the sum of n and m is 2 to 60, preferably 2 to 40, more preferably 3 to 30 and in particular 5 to 25. In a further particularly preferred embodiment R ² and R ^{3 is} ethylene and the sum 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 particularly preferred embodiment, R ² and R ^{3 are} ethylene and the sum of n and m 1 1 to 40, in particular 12 to 30 and in particular 13.5 to 25. The compounds (A) and (AQ) can be used as mixtures of Stereoisomers present or as isolated stereoisomers. Tautomers and betaines are also included among structures (A) and (AQ).

The composition according to the invention usually contains 0.1 to 90% by weight of the alkoxylate, preferably 1 to 50% by weight and in particular 3 to 30% by weight. The term pesticides denotes at least one active substance selected from the group of fungicides, insecticides, nematicides, herbicides, safeners, molluscicides, rodentizides and / or growth regulators. Preferred pesticides are fungicides, insecticides, herbicides, and growth regulators. Particularly preferred pesticides are herbicides and growth regulators. Also, mixtures of pesticides of two or more of the above classes may be used. One skilled in the art will be familiar with such pesticides as described, for example, in Pesticide Manual, 14th Ed. (2006), The British Crop Protection Council, London. Suitable pesticides are: A) strobilurins:

 Azoxystrobin, Dimoxystrobin, Coumoxystrobin, Coumethoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Metominostrobin, Orysastrobin, Picoxystrobin, Pyracoltrobin, Pyrametostrobin, Pyraoxystrobin, Pyribencarb, Trifloxystrobin, 2- [2- (2,5-dimethylphenyl-oxymethyl) phenyl] -3-methoxy-acrylic acid methyl ester, 2- (2- (3- (2,6-dichlorophenyl) -1-methyl-allylideneaminooxymethyl) -phenyl) -2-methoxyimino-N-methyl-acetamide;

 B) Carboxylic acid amides:

 - carboxylic acid anilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carbo-xin, fenfuram, fenhexamide, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, Penflufen (N- (2- (1,3-dimethyl-butyl) -phenyl) -1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide), penthiopyrad, sedaxanes, tecloftalam, thifluzamide, Tiadinil, 2-amino-4-methyl-thiazole-5-carboxanilide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4 carboxamide, N- (4'-trifluoromethylthiobiphenyl-2-yl) -3-difluoro-methyl-1-methyl-1H-pyrazole-4-carboxamide, N- (2- (1,3,3-trimethyl-butyl) -phenyl) -1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide;

 - Carboxylic acid morpholides: dimethomorph, flumorph, pyrimorph;

 Benzoic acid amides: flumetover, fluopicolide, fluopyram, zoxamide;

 Other carboxamides: carpropamide, diclocymet, mandipropamide, oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropanecarboxamide;

 C) Azoles:

 - Triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole , Prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole;

- imidazoles: cyazofamide, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizole;

Benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;

 - Other: ethaboxam, etridiazole, hymexazole, 2- (4-chloro-phenyl) -N- [4- (3,4-dimethoxyphenyl) -isoxazol-5-yl] -2-prop-2-ynyloxy-acetamide ;

 D) Nitrogen-containing heterocyclyl compounds

Pyridines: fluazinam, pyrifenox, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] - Pyridine, 3- [5- (4-methylphenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine;

 Pyrimidines: Bupirimat, Cyprodinil, Diflumetorim, Fenarimol, Ferimzone, Mepanipyrim, Nitrapyrin, Nuarimol, Pyrimethanil;

 - piperazines: triforins;

- Pyrroles: fludioxonil, fenpiclonil;

 - morpholines: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph;

- piperidines: fenpropidine;

 Dicarboximides: fluorimide, iprodione, procymidone, vinclozolin;

 non-aromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, octhilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydropyrazole-1-thiocarboxylic acid allyl ester;

 - Other: acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, quinomethionate, dazomet, debacarb, diclomethine, difenzoquat, difenzoquat-methylsulfate, fenoxanil, folpet, oxolinic acid, piperaline, proquinazid, pyroquilon, qui - Noxyfen, triazoxide, tricyclazole, 2-butoxy-6-iodo-3-propyl-chromen-4-one, 5-chloro-1 - (4,6-dimethoxypyrimidin-2-yl) -2-methyl-1 H-benzoimidazole, 5-chloro-7- (4-methyl-piperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a ] pyrimidine, 5-ethyl-6-octyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ylamine;

E) carbamates and dithiocarbamates

Thio and dithiocarbamates: Ferbam, Mancozeb, Maneb, Metam, Methasulphocarb, Metiram, Propineb, Thiram, Zineb, Ziram;

 Carbamates: Diethofencarb, Benthiavalicarb, Iprovalicarb, Propamocarb, Propamocarb hydrochloride, Valiphenal, N- (1- (1- (4-cyanophenyl) ethanesulfonyl) -but-2-yl) carbamic acid- (4-fluorophenyl) ester;

F) Other fungicides

 Guanidines: dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadin tris (albesilat);

 Antibiotics: kasugamycin, kasugamycin hydrochloride hydrate, polyoxines, streptomycin, validamycin A;

Nitrophenyl derivatives: binapacryl, diclorane, dinobutone, dinocap, nitrothal-isopropyl, tecnazene;

 Organometallics: fentin salts such as fentin acetate, fentin chloride, fentin hydroxide;

 Sulfur-containing heterocyclyl compounds: dithianone, isoprothiolanes;

Organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;

 Organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophene, flusulphamide, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phthalide, quintozene, thiophanate-methyl, tolylfluanid, N- (4-chloro-2-nitro-phenyl) -N-ethyl-4- methyl-benzenesulfonamide;

Inorganic active substances: phosphorous acid and its salts, Bordeaux broth, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic beautiful copper sulphate, sulfur;

- Biological fungicides, plant strengthening agents: Bacillus subtilis strain NRRL no. B-21661 (for example, the products Rhapsody ^®, SERENADE ^® MAX and SERENADE ^® ASO of Fa. AgraQuest, Inc., USA.), Bacillus pum / ^'/ us strain NRRL no. B- 30087 (eg SONATA ^® and BALLAD ^® Plus from. AgraQuest, Inc., USA), Ulocladi- to oudemansii (eg BOTRY ZEN Fa. BotriZen Ltd., New Zealand), chitosan (eg ARMOR ZEN Fa. BotriZen Ltd., New Zealand).

 - Other: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamine, metrafenone, mildiomycin, oxine-copper, prohexadione-calcium, spiroxamine, tolylfluanid, N- (cyclopropylmethoxyimino- (6-difluoromethoxy-2,3-difluorophenyl) - methyl) -2-phenylacetamide, N '- (4- (4-chloro-3-trifluoromethylphenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamide, N' - (4- (4-Fluoro-3-trifluoromethylphenoxy) -2,5-dimethylphenyl) -N-ethyl-N-methylformamidine, N '- (2-methyl-5-trifluoromethyl-4- (3-trimethylsilanyl) propoxy) -phenyl) -N-ethyl-N-methylformamidine, N '- (5-difluoromethyl-2-methyl-4- (3-trimethylsilanyl-propoxy) -phenyl) -N-ethyl-N-methylformamidine, 2- { 1 - [2- (5-Methyl-3-trifluoromethyl-pyrazol-1-yl) -acetyl] -piperidin-4-yl} -thiazole-4-carboxylic acid-methyl- (1,2,3,4-tetra- hydronaphthalene-1-yl) -amide, 2- {1- [2- (5-methyl-3-trifluoromethyl-pyrazol-1-yl) -acetyl] -piperidin-4-yl} -thiazole-4-carboxylic acid-methyl - (R) -1, 2,3,4-tetrahydronaphthalene-1-yl-amide, acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl-es methoxyacetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester, A / methyl 2- {1 - [2- (5-meth - yl-3-trifluoromethyl-1H-pyrazol-1-yl) -acetyl] -piperidin-4-yl} -A / - [(1R) -1, 2,3,4-tetrahydronaphthalene-1 - yl] -4-thiazolecarboxamide;

 G) growth regulator

 Abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butraline, chlormequat (chlorequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipine, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfid , indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), metconazole, naphthalene acetic acid, N-6-benzyladenine, paclobutrazole, prohexadione (prohexadione-calcium), Prohydrojasmon, thidiazoron, tri-penthenol, tributyl phosphorotrithioate, 2,3 5-tri-iodobenzoic acid, trinexapac-ethyl and uniconazole;

 H) herbicides

 Acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamide, pretilachlor, propachlor, thenylchloro;

 Amino acid analogues: bilanafos, glyphosate, glufosinate, sulfosate;

 Aryloxyphenoxypropionates: Clodinafop, Cyhalofop-butyl, Fenoxaprop, Fluazifop, Haloxyfop, Metamifop, Propaquizafop, Quizalofop, Quizalofop-P-tefuryl;

 Bipyridyls: diquat, paraquat;

Carbamates and thiocarbamates: asulam, butylates, carbamides, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinates, orbencarb, phenmedipham, prosulphocarb, pyributicarb, thiobencarb, triallates; - cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim;

 - Dinitroanilines: Benfluralin, Ethalfluralin, Oryzalin, Pendimethalin, Prodiamine, Trifluralin;

Diphenyl ether: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;

 Hydroxybenzonitriles: bromoxynil, dichlobenil, loxynil;

 - imidazolinones: imazamethabenz, imazamox, 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, Pyridate;

 Pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, piclamoram, picolinafen, thiazopyr;

Sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl,

Chlorosulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, lodosulfuron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, Trisulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 - ((2-chloro)

6-propylimidazo [1,2-b] pyridazin-3-yl) sulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea;

 Triazines: ametryn, atrazine, cyanazine, dimethametryn, ethiozine, hexazinone, metachronon, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;

Ureas: chlorotoluron, da- muron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron;

 - other inhibitors of acetolactate synthase: bispyribac sodium, cloransulam methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, orthosulphamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxime, pyriftalid, pyriminobac-methyl, pyrimisulphane, pyrithiobac, pyroxasulphone, pyroxsulam;

- Other: Amicarbazone, Aminotriazole, Anilofos, Beflubutamide, Benazoline, Bencarbazone, Benfluresat, Benzofenap, Bentazone, Benzobicyclone, Bromacil, Bromobutide, Bu- tattacil, Butamifos, Cafenstrole, Carfentrazone, Cinidone-Ethlyl, Chlorthal, Cinmethyllin, Clomazone , Cumyluron, cyprosulfamide, dicamba, difenzoquat, diflufenzopyr, Drechsler's monoceras, endothal, ethofumesate, etobenzanide, fentrazamide, flumiclorac-pentyl, flumioxazine, flupoxam, fluorochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, Quinclorac, quinmerac, mesotrione, methylarsenoic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefon, pentoxazone, pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotol, pyrazoxyfen, pyrazolynate, quinoclamin, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, Topramezone, 4-hydroxy-3- [2- (2-methoxy-ethoxymethyl) -6-trifluoromethyl-pyridine-3-carbonyl] -bicyclo [3.2.1] oct-3-en-2-one, (3- [2-Chloro-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidine-1-yl) -phenoxy] -pyridine-2-one. yloxy) -acetic acid ethyl ester, 6-amino-5-chloro-2-cyclopropyl-pyrimidiri-4-carboxylic acid methyl ester, 6-chloro-3- (2-cyclopropyl-6-methyl-phenoxy) - pyridazin-4-ol, 4-amino 3-chloro-6- (4-chloro-phenyl) -5-fluoro-pyridine-2-carboxylic acid, 4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methoxy-phenyl) -pyridine-2-carboxylic acid methyl ester and 4-amino-3-chloro-6- (4-chloro-3-dimethylamino-2-fluoro-phenyl) -pyridine-2-carboxylic acid methyl ester;

I) insecticides

 Organo (thio) phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulphoton, ethion, fenitrothion, fenthione, isoxathione, malathion, methamidophos, methidathion , Methyl Parathion, Mevinphos, Monocrotophos, Oxydemeton-Methyl, Paraoxone, Parathion, Phenthoate, Phosalone, Phosmet, Phosphamidon, Phorate, Phoxim, Pirimiphos-Methyl, Profenofos, Prothiofos, Sulprophos, Tetrachlororphos, Terbufos, Triazophos, Trichlorfon;

 Carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamates;

 - pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalo- thrin, permethrin, prallethrin , Pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin,

Insect growth inhibitors: a) chitin synthesis inhibitors: benzoylureas: chlorofluorazuron, cyramazine, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; Buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) Juvenoids: Pyriproxyfen, Methoprene, Fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spinotetramat;

 Nicotine receptor agonists / antagonists: clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1- (2-chlorothiazol-5-ylmethyl) -2-nitrimino-3,5-dimethyl- [1, 3,5] triazinane;

 - GABA antagonists: endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, 5-amino-1 - (2,6-dichloro-4-methyl-phenyl) -4-sulfinamoyl-1H-pyrazole-3-thiocarbon acid amide;

 Macrocyclic lactones: Abamectin, Emamectin, Milbemectin, Lepimectin, Spinosid, Spinetoram;

 - mitochondrial electron transport chain inhibitor (METI) I acaricides: Fenazaquin, Pyridaben, Tebufenpyrad, Tolfenpyrad, Flufenerim;

 - METI II and III substances: Acequinocyl, Fluacyprim, Hydramethylnon;

- decoupler: chlorfenapyr; - inhibitors of oxidative phosphorylation: cyhexatin, diafenthiuron, fenbutatin oxide, propargite;

 Inhibitors of the sloughing of insects: Cryomazine;

 Inhibitors of mixed function oxidases: piperonyl butoxide;

Sodium channel blocker: indoxacarb, metaflumizone;

 - Other: Benclothiaz, Bifenazate, Cartap, Flonicamid, Pyridalyl, Pymetrozine,

 Sulfur, thiocyclam, flubendiamide, chlorantraniliprole, cyazypyr (HGW86); Cynopyphron, Flupyrazofos, Cyflumetofen, Amidoflumet, Imicyafos, Bistrifluron and Pyrifluquinazone.

Preferred pesticides comprise at least one pesticide having at least one H-acidic group (such as carboxylic acid group, phosphonic acid group, phosphinic acid group) or their anionic salts (eg mono-, di- or trisalts). These anionic salts of pesticides having an H-acidic group. Acid group are also suitable as anionic pesticides in the group A-. Preferred pesticides having an H-acidic group are herbicides having an H-acidic group. Examples of herbicides with an H-acidic group are amino acid analogues (such as glyphosate or glufosinate) or imidazolinones (such as imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr).

Particularly preferred pesticides with an H-acid group are glyphosate and glufosinate. In a further preferred embodiment, pesticides having an H-acidic group are imidazolinones.

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

In another preferred embodiment, the pesticide comprises glyphosate (e.g., as the free acid, sodium salt, sesquioxium salt, potassium salt, dipotassium salt, ammonium salt, diammonium salt, dimethyl ammonium salt, trimesium salt or isopropylamine salt) or glufosinate (e.g., ammonium salt). Most preferably, the pesticide comprises glyphosate (e.g., potassium salt, ammonium salt, isopropylamine salt). Particularly preferably, the pesticide comprises glyphosate or glufosinate, and in addition a further herbicide. In another preferred embodiment, the pesticide comprises glyphosate or glufosinate, and additionally another pesticide (such as at least one fungicide, herbicide, insecticide, and / or safener, with fungicides and / or herbicides being preferred).

The compositions according to the invention can furthermore also be used for agrochemicals. see formulations contain conventional adjuvants, with the choice of adjuvant according to the specific application form, the type of formulation or the drug is directed. Examples of suitable auxiliaries are solvents, solid carriers, surface-active substances (such as surfactants, solubilizers, protective colloids, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, if appropriate dyes and adhesives (for example for seed treatment ) or conventional adjuvants for bait formulations (eg attractants, feeds, bitter substances).

Suitable solvents are water or organic solvents, such as mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, gycols, ketones such as cyclohexanone, gamma-butyrolactone, dimethyl fatty acid amides, fatty acids and fatty acid esters and highly polar Solvent, eg Amines such as N-methylpyrrolidone, into consideration. In principle, solvent mixtures and mixtures of the abovementioned solvents and water can also be used. Solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell meal, cellulose powder or other solid carriers.

As surfactants (adjuvants, wetting agents, adhesives, dispersants or emulsifiers) are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, eg. B. of lignin (Borresperse ^® grades, Borregaard, Norway), phenol, naphthalene (Morwet ^® types, Akzo Nobel, USA) and dibutyl (nekal ^® types, BASF, Germany), and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acids with Phenol and formaldehyde, polyoxyethylene nonylphenol ethers, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin Sulfite liquors as well as proteins, denatured proteins, polysaccharides (eg Methy lcellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol ^® types, Clariant, Switzerland), Polycarboxyla- te (Sokalan ^® types, BASF, Germany), polyalkoxylates, polyvinylamine (Lupamin ^® - Types, BASF, Germany), polyethyleneimine (Lupasol ^® types, BASF, Germany), polyvinylpyrrolidone and copolymers thereof.

The composition according to the invention may comprise from 0.1 to 40% by weight, preferably from 1 to 30 and in particular from 2 to 20% by weight of surface-active substances, the amount of alkoxlylate (A) and (AQ) not being included.

Suitable thickeners are compounds which impart a modified flow behavior to the formulation, ie a high viscosity at rest and low viscosity in an agitated state. Examples are polysaccharides, proteins (such as casein or gelatin), synthetic polymers, or inorganic layer minerals. Such thickeners are commercially available, such as Xanthan Gum (Kelzan ^®, CP Kelco, U.S.A.), Rhodopol ^® 23 (Rhodia, France) or Veegum ^® (RT Vanderbilt, USA) or Attac lay ^® (Engelhard Corp., NJ, USA) , The content of thickener in the formulation depends on the effectiveness of the thickener. One skilled in the art will select a level to obtain the desired viscosity of the formulation. The content will usually be 0.01 to 10 wt.%.

Bactericides may be added to stabilize the composition. Examples of bactericides are those based on dichlorophen and benzyl alcohol formal and isothiazolinone derivatives such as alkylisothiazolinones and Benzisothiazolino- nen (Acetide ^® MBS from Thor Chemie).. Examples of suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin. Examples of defoamers are silicone emulsions (such as, for example, silicone ^® SRE, Wacker, Germany or Rhodorsil ^®, Rhodia, France), long chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.

The composition of the invention may preferably be in the form of an agrochemical formulation. Examples of such formulations and their preparation are:

i) Water-soluble concentrates (SL, LS): 10 parts by weight of the active ingredients are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a composition with 10 wt .-% active ingredient content.

ii) Dispersible Concentrates (DC): 20 parts by weight of the active ingredients are used in 70

 Parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant z. B. dissolved polyvinylpyrrolidone. Dilution in water gives a dispersion. The active ingredient content is 20% by weight

iii) Emulsifiable Concentrates (EC): 15 parts by weight of the active compounds are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water gives an e mulsion. The composition has 15% by weight active ingredient content.

iv) Emulsions (EW, EO, ES): 25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is added by means of an emulsifying machine (eg Ultra-Turrax) in 30 parts by weight of water and brought to a homogeneous emulsion. Dilution in water results in an emulsion. The composition has an active ingredient content of 25 wt .-%.

v) Suspensions (SC, OD, FS): 20 parts by weight of the active ingredients are mixed with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine

Crushed active ingredient suspension. Dilution in water results in a stable suspension of the active ingredient. The active ingredient content in the composition is 20% by weight.

vi) Water-dispersible and water-soluble granules (WG, SG): 50 parts by weight of the active ingredients are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and by means of technical equipment (eg., Extrusion, spray tower, fluidized bed) water-dispersible or water-soluble granules produced. Dilution in water results in a stable dispersion or solution of the active ingredient. The composition has an active substance content of 50% by weight.

vii) Water-dispersible and water-soluble powders (WP, SP, SS, WS): 75 parts by weight of the active ingredients are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient. The active ingredient content of the composition is 75% by weight.

viii) Gels (GF): In a ball mill, 20 parts by weight of the active ingredients, 10 parts by weight of dispersant, 1 part by weight of swelling agent ("gelling agent") and 70 parts by weight of water or an organic solvent are added When diluted with water, a stable suspension with 20% by weight active substance content results.

ix) dusts (DP, DS): 5 parts by weight of the active ingredients are finely ground and mixed with 95

Parts by weight of finely divided kaolin intimately mixed. This gives a dust with 5 wt .-% active ingredient content.

x) Granules (GR, FG, GG, MG): 0.5 parts by weight of the active ingredients are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray-drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.

xi) ULV solutions (UL): 10 parts by weight of the active compounds are dissolved in 90 parts by weight of an organic solvent, for. B. dissolved xylene. This gives a composition for direct application with 10 wt .-% active ingredient content.

The compositions generally contain from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight of the pesticides. The user usually uses the composition according to the invention for use in a pre-metering device, in the back splash, in the spray tank or in the spray plane. The formulation is brought to the desired application concentration with water and / or buffer, further adjuvants being added if necessary, and the ready-to-use spray mixture (so-called tank mix) is thus obtained. Usually, 50 to 500 liters of ready-spray mixture per hectare of agricultural land, preferably 100 to 400 liters. In special segments, these quantities can also be exceeded (eg orchards) or undershot (eg aircraft applications). The active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%. Oils of various types, wetting agents, drift reducing agents, stickers, spreaders, adjuvants, fertilizers, plant strengthening agents, trace elements, herbicides, bactericides, fungicides and / or pesticides, if appropriate also immediately before use, can be added to the active substances or compositions containing them become. These agents can be mixed into the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1. As adjuvants in this sense are in particular: organically modified polysiloxanes, eg. B. Break Thru S ^240® ; Alcohol alkoxylates, eg. B. Atplus 245 ^®, Atplus MBA ^® 1303 Plurafac ^® LF 300 and Lutensol ON 30 ^®; EO-PO block polymers, eg. B. Pluronic RPE 2035 ^® and Genapol B ^®; Alcohol ethoxylates, eg. B. Lutensol ^® XP 80; and sodium dioctylsulfosuccinate, e.g. B. Leophen ^® RA.

Depending on the nature of the desired effect, the application rates of the active substance are between 0.001 and 2.0 kg of active ingredient per ha, preferably between 0.005 and 2 kg per ha, more preferably between 0.05 and 0.9 kg per ha. in particular between 0.1 and 0.75 kg per ha.

The present invention further relates to a method for controlling phytopathogenic fungi and / or undesired plant growth and / or undesired insect or mite infestation and / or for regulating the growth of plants, wherein the composition according to the invention on the respective pests, their habitat or the plants to be protected from the respective pest, the soil and / or undesirable plants and / or the crops and / or their habitat. Suitable crops are, for example, cereals, z. Wheat, rye, barley, triticale, oats or rice; Beets, z. Sugar or fodder beets; Kernel, stone and berry fruits, z. Apples, pears, plums, peaches, almonds, cherries, strawberries, brain berries, currants or gooseberries; Legumes, z. Beans, lentils, peas, alfalfa or soybeans; Oil plants, e.g. Rapeseed, mustard, olives, sunflowers, coconut, cocoa, castor beans, oil palm, peanuts or soya; Cucurbits, z. Pumpkins, cucumbers or melons; Fiber plants, z. Cotton, flax, hemp or jute; Citrus fruits, z. Oranges, lemons, grapefruit or mandarins; Vegetables, z. Spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, squash or paprika; Laurel family, z. Avocados, cinnamon or camphor; Planting energy and raw materials, eg. Corn, soy, wheat, rapeseed, sugarcane or oil palm; Corn; Tobacco; Nuts; Coffee; Tea; bananas; Wine (table and grapes); Hop; Grass, z. B. lawn; Sweet herb (Stevia rebaudania); Rubber plants; Ornamental and forest plants, z. As flowers, shrubs, deciduous and coniferous trees and propagating material, eg. B. seeds, and crops of these plants.

The term "crops" also includes those plants that have been modified by breeding, mutagenesis or genetic engineering, including biotechnological agricultural products on the market or in development. Genetically engineered plants are plants whose genetic material has been altered in a manner that does not occur under natural conditions by crossing, mutations or natural recombination (i.e., rearrangement of genetic information). As a rule, one or more genes are integrated into the genome of the plant in order to improve the properties of the plant. Such genetic engineering also includes post-translational modifications of proteins, oligo- or polypeptides, e.g. by glycolylation or binding of polymers such as e.g. prenylated, acetylated or farnelysierter residues or PEG residues.

By way of example, plants may be mentioned which, through breeding and genetic engineering measures, tolerate certain types of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, Sulfonylureas (EP-A 257 993, US 5,013,659) or imidazolinones (eg US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, 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. Glyphosate (see, for example, WO 92/00377), glutamine synthetase (GS) inhibitors such as. Glufosinate (see eg EP-A 242 236, EP-A 242 246) or oxynil herbicides (see eg US 5,559,024). By breeding and mutagenesis z. B. Clearfield ^® rapeseed (BASF SE, Germany) produced, the tolerance to imidazolinones, z. As imazamox, has. Using genetic engineering methods, crop plants such as soybean, produces cotton, corn, beets and rape, which are resistant to glyphosate or glufosinate, and sold under the trade name RoudupReady ^® (glyphosate-resistant, Monsanto, USA) and Liberty Link ^® ( Glufosinate-resistant, Bayer CropScience, Germany). Furthermore, plants are included which, with the aid of genetic engineering measures one or more toxins, eg. B. those from the bacterial strain Bacillus produce. Toxins produced by such genetically engineered plants include e.g. B. Insecticidal proteins of Bacillus spp., In particular B. thuringiensis, such as the endotoxins CrylAb, CrylAc, Cry1F, Cry1Fe2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs), e.g. VIP1, VIP2, VIP3, or VIP3A; Insecticidal proteins of nematode-colonizing bacteria, e.g. B. Photorhabdus spp. or Xenorhabdus spp .; Toxins from animal organisms, eg. B. Wepsen, spider or scorpion toxins; fungal toxins, e.g. Eg from Streptomyces; herbal lectins, e.g. From pea or barley; agglutinins; Proteinase inhibitors, e.g. Trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; Ribosome Inactivating Proteins (RIPs), e.g. Ricin, corn RIP, abrin, luffin, saporin or bryodin; Steroid metabolizing enzymes, e.g. 3-hydroxy steroid oxidase, ecdysteroid IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase; ion channel blocker, e.g. B. inhibitors of sodium or calcium channels; Juvenile hormone esterase; Receptors for the diuretic hormone (helicokinin receptors); Stilbene synthase, bibenzyl synthase, chitinases and glucanases. These toxins can also be produced in the plants as proteoxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a novel combination of different protein domains (see, for example, WO 2002/015701). Further examples of such toxins or genetically modified plants which produce these toxins are described 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 discloses. The methods for producing these genetically modified plants are known to the person skilled in the art and z. As set forth in the publications mentioned above. Numerous of the aforementioned toxins confer on the plants that produce them tolerance to pests of all taxonomic arthropod classes, in particular to beetles (Coeleropta), diptera (Diptera) and

Butterflies (Lepidoptera) and nematodes (Nematoda). Genetically modified plants which produce one or more genes coding for insecticidal toxins, eg. As described in the publications mentioned above and partly commercially available, such as. B. YieldGard ^® (corn cultivars producing the toxin CrylAb), YieldGard ^® Plus (corn cultivars producing the toxins CrylAb and Cry3Bb1), StarLink ^® (corn cultivars producing the toxin Cry9c), Herculex ^® RW (corn cultivars produce the toxins Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin N-acetyltransferase [PAT]); NuCOTN ^® 33B (cotton cultivars producing the toxin CrylAc), Bollgard ^® I (cotton cultivars producing the toxin CrylAc), Bollgard ^® II (cotton cultivars producing the toxins CrylAc and Cry2Ab2); VIP COT ^® (cotton cultivars producing a VIP-toxin); NewLeaf ^® (potato cultivars producing the Cry3A toxin); Bt Xtra ^®, NatureGard® ^®, KnockOut ^®, BiteGard ^®, Protec ta ^®, Bt1 1 (z. B. Agrisure ^® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which the toxin CrylAb and the PAT Produce enzyme), MIR604 from Syngene ta Seeds SAS, France (maize varieties producing a modified version of the toxin Cry3A, see WO 03/018810), MON 863 from Monsanto Europe SA, Belgium (maize varieties producing the toxin Cry3Bb1), IPC 531 from Monsanto Europe SA, Belgium (cotton varieties producing a modified version of the toxin CrylAc) and 1507 from Pioneer Overseas Corporation, Belgium (maize varieties producing the toxin Cryl F and the PAT enzyme).

Furthermore, plants are also included which, with the aid of genetic engineering measures, produce one or more proteins which bring about increased resistance or resistance against bacterial, viral or fungal pathogens, such as, for example, For example, so-called pathogenesis-related proteins (PR proteins, see EP-A 0 392 225), resistance proteins (eg potato varieties which produce two resistance genes against Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum) or T4 lysozyme (For example, potato varieties that are resistant to bacteria such as Erwinia amylvora as a result of the production of this protein).

Furthermore, plants are included whose productivity has been improved by genetic engineering methods by z. For example, yield (eg biomass, grain yield, starch, oil or protein content), tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens may be increased.

Furthermore, plants are included whose ingredients have been modified in particular to improve the human or animal diet using genetic engineering methods by z. For example, oil plants can produce health-promoting long-chain omega-3 fatty acids or monounsaturated omega-9 fatty acids (eg Nexera ^® rapeseed, DOW Agro Sciences, Canada).

The present invention also relates to seeds (such as seeds or other plant propagating materials) containing the composition according to the invention.

Herbal propagating materials may be preventively treated with or with the composition of the invention prior to sowing or together with or even before transplanting. For the treatment of seeds usually water-soluble concentrates (LS), suspensions (FS), dusts (DS), water-dispersible and water-soluble powders (WS, SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are used. These compositions can be applied to the propagating materials, in particular seeds, undiluted or, preferably, diluted. In this case, the corresponding composition can be diluted 2 to 10 times, so that 0.01 to 60% by weight, preferably 0.1 to 40% by weight of active compound are present in the compositions to be used for the stain. The application can be done before or during sowing. The

Treatment of plant propagating material, in particular the treatment of seed, are known to the person skilled in the art and are carried out by dusting, coating, Pelleting, dipping or soaking the plant propagating material, wherein the treatment is preferably carried out by pelleting, coating and dusting or by furrow treatment, so that z. B. premature germination of the seed is prevented. For seed treatment, suspensions are preferably used. Such compositions usually contain 1 to 800 g / l of active ingredient, 1 to 200 g / l of surfactants, 0 to 200 g / l of antifreeze, 0 to 400 g / l of binder, 0 to 200 g / l of dyes and solvents, preferably water ,

The present invention furthermore relates to an alkoxylate, where the alkoxylate is an aminoalkoxylate (A)

is, where

R ^{1 is} a branched, aliphatic alkyl radical C17H35,

R ² , R ³ , and R ^{7 are} independently ethylene, propylene, butylene, or a mixture thereof,

R ^{4 is} H, -OH, -OR ⁶ , - [R ⁷ -O] _p -R ⁵ , C ₁ -C ₆ -alkyl or an oxygen anion,

R ^{5 is} H, dC ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, -SO ₃ R ^a , -P (O) OR ^b OR ^c ,

-CH ₂ C0 ₂ R ^d , or -C (O) R ^e

R ⁶ is a Ci-C ₆ alkyl, C ₂ -C ₆ alkenyl, or C ₂ -C ₆ alkynyl,

R ^a and R ^d independently of one another are H, inorganic or organic cations,

R ^b and R ^{c are} independently H, inorganic or organic cations, C1-

C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl,

R ^e d C ₂₂ alkyl, C ₆ -C ₂₂ aryl, C ₇ -C ₂₂ alkylaryl,

n, m and p independently of one another a value of 1 to 30, and

A- is an agriculturally acceptable anion or, if R ^{4 is} an oxygen anion, A- is not present.

Further preferred embodiments are as described above.

The present invention furthermore relates to an alkoxylate, where the alkoxylate is a quaternized derivative (AQ).

the Aminalkoxylats (A), wherein

R ^{1 is} a branched, aliphatic alkyl radical C17H35,

R ² , R ³ , and R ^{7 are} independently ethylene, propylene, butylene, or a mixture thereof,

R ^{4 is} H, -OH, -OR ⁶ , - [R ⁷ -O] _p -R ⁵ , C ₁ -C ₆ -alkyl or an oxygen anion,

R ^{5 is} H, dC ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, -SO ₃ R ^a , -P (O) OR ^b OR ^c ,

-CH ₂ C0 ₂ R ^d , or -C (O) R ^e R ⁶ is a Ci-C ₆ alkyl, C ₂ -C ₆ alkenyl, or C ₂ -C ₆ alkynyl,

R ^a and R ^d independently of one another denote H, inorganic or organic cations, R ^b and R ^c independently of one another denote H, inorganic or organic cations,

C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl,

R ^e Ci-C ₂₂ alkyl, C ₆ -C ₂₂ -aryl, C ₇ -C ₂₂ alkylaryl,

n, m and p independently of one another a value of 1 to 30, and

A- is an agriculturally acceptable anion or, if R ^{4 is} an oxygen anion, A- is not present.

 In this case, A- is preferably a halide (such as chloride or bromide), phosphate, sulfate or an anionic pesticide. More preferably, A is an anionic pesticide, such as

Glyphosate anion or glufosinate anion. Further preferred embodiments are as described above.

The present invention further relates to processes for preparing the Aminalkoxyl- (A) or a quaternized derivative (AQ) of Aminalkoxylats (A) comprising the alkoxylation of amines R ¹ -NH ₂ with ethylene oxide, propylene oxide, butylene oxide or a mixture thereof.

Another object of the present invention is the amine R ¹ -NH ₂ . It is an important intermediate for the preparation of the amine alkoxylate (A) or a quaternized derivative (AQ) of the amine alkoxylate (A). Preferred embodiments of R1 are as described above. The amines R ¹ -NH ₂ can be prepared by reacting ammonia with alcohols R ¹ -OH. Suitable catalysts and reaction conditions are described in US 5,808,158.

The alcohols R ¹ -OH can in principle be synthesized by any desired process, provided that they each have the described degree of branching. Alcohols R ¹ -OH can be obtained, for example, from a branched C 16 -olefin by hydroformylation followed by hydrogenation of the resulting aldehyde to give the alcohol. The carrying out of a hydroformylation and the subsequent hydrogenation is known in principle to the person skilled in the art, as is known from WO 2009/124979. The Ci6 olefins used for this purpose can be prepared by tetramerization of butene.

Preferably, the Ci7 alcohol mixture can be prepared by a) providing a hydrocarbon feedstock containing at least one olefin having 2 to 6 carbon atoms, b) subjecting the hydrocarbon feedstock to oligomerization on a transition metal-containing catalyst, c) subjecting the oligomerization product obtained in step b) to distillative separation to give an olefin stream enriched in C 16 -olefins, d) the olefin stream of a hydroformylation enriched in C 6 -olefins obtained in step c) by reaction with carbon monoxide and hydrogen in the presence of a cobalt Hydroformylation and then subjected to hydrogenation.

The details of this synthesis are generally known to the person skilled in the art, for example from WO 2009/124922 [step a) see page 8, line 27 to page 11, line 8; Step b) see page 1 1, line 10 to page 13, line 41; Step c) see page 14, line 1 to page 15, line 15; Step d) see page 15, line 17 to page 17, line 26]. A particularly suitable alcohol R ¹ -OH can be prepared as described in WO 2009/124922 Example IA (page 29, line 5 to page 31, line 23).

The alkoxylation can be carried out by strong bases, such as alkali metal hydroxides and alkaline earth hydroxides, Brönsted acids or Lewis acids, such as AlC, BF3. be catalyzed. For narrow alcohol alkoxylates, catalysts such as hydrotalcite or DMC can be used. The alkoxylation is preferably carried out at temperatures in the range of about 80 to 250 ° C, preferably about 100 to 220 ° C. The pressure is preferably between ambient pressure and 600 bar. If desired, the alkylene oxide may be an inert gas admixture, e.g. From about 5 to 60%.

The quaternized derivative (AQ) of the amine alkoxylate (A) can be prepared in a further reaction step from the aminal alkoxylate (A) by quaternization. For the introduction of the radical R ⁴ into the Aminalkoxylat (A), it can be reacted for example with an alkylating reagent such as methyl chloride, dimethyl sulfate, or butyl chloride. For the introduction of an oxygen anion into the amine alkoxylate (A) it can be oxidized, for example by reaction of the amino group with hydrogen peroxide, peracids (such as meta-chloroperbenzoic acid or peracetic acid) or peroxomonosulphuric acid.

The preparation of the quaternized derivative (AQ) with R ⁴ = H can be carried out by simple protonation of starting compounds of structure (A). The preparation of the quaternized derivatives (AQ) with R ⁴ = OH can be carried out by simple protonation of starting compounds (AQ) with R ⁴ = oxygen anion. Suitable acids for protonation are organic acids (for example C.sub.1 to C.sub.20 carboxylic acids, in particular benzoic acid) or inorganic acids (for example hydrochloric acid, phosphoric acid or sulfuric acid). Also suitable are H-azide pesticides such as glyphosate acid or glyphosate monosalts. The protonation can be carried out in a separate synthesis step, so that the quaternized derivative (AQ) can be isolated. It is also possible to protonation by mixing the starting compounds with to carry out one or more acids in the composition or in the spray mixture.

The present invention also relates to the use of the Aminalkoxylats (A) or a quaternized derivative (AQ) of Aminalkoxylats (A) as described above as an aid in pesticide-containing spray liquors. The auxiliary is preferably an agent that increases the efficiency. Such enhancers are also called adjuvants. They increase or accelerate the effect of pesticides compared to the action of the pesticide in the absence of the adjuvant.

The advantages of the invention are high formulation stability and spray liquor, low wind drift on spray application, high adhesion of the formulation to the surface of the treated plants, increasing the solubility of the pesticides in the formulation, increased permeation of the pesticides into the plant and with it a faster and increased effectiveness. An important advantage is the low toxicity of the new alkoxlyates, especially the low aquatoxicity. An advantage is also the low harmfulness against crop plants, i. a low phytotoxic effect. Another advantage lies in the ease of handling these alkoxides, as e.g. when incorporated in formulations no gelation occurs.

The following examples illustrate the invention without limiting it.

Examples

Example 1: Preparation of branched Ci7 amine from Ci7 alcohol

 The branched Ci7 alcohol (degree of branching of 3.1) was prepared as in WO

2009/124922, Example I (page 29, line 5 to page 31, line 23). The C 18 -alcohol (1500 g) and an alcohol-amination catalyst (described in EP 696 572 A1, 6.7% by weight with respect to C 14 -alcohol) were initially charged in an autoclave and purged with nitrogen and hydrogen. Then, 8000 g of ammonia was charged and heated with stirring. After a reaction time of ten hours at 250 ° C and a pressure of 250 bar 250, the Ci7 amine thus obtained was filtered and freed from water on a rotary evaporator. The amine content was 199.6 g KOH / g, and the water content below 0.1 wt.%.

Example 2: Alkoxylation of branched C 7 -amine

First of all 650 g (2.3 mol) of the C 7 -amine from Example 1 (amine number 299 mg KOH / g) were admixed with 17.1 g of water. Then, at 100 ° C., 203 g (4.61 mol) of ethylene oxide (EO) were metered in in a mass-controlled manner over 12 h. The mixture was then stirred at 100 ° C for 6 h. At- closing was dehydrated at 90 ° C under vacuum for 2 h. This gave a yield of 855 g (= 101% dT) with an amine number of 152 mg KOH / g (152 mg KOH / g theory). In the second step, 200 g (0.54 mol) of this precursor was 2.0 g 50%

KOH added and dehydrated at 90 ° C under vacuum for 2h. After purging with nitrogen, 309 g (7.0 mol) of ethylene oxide were metered in at a controlled rate at 120 ° C. over a period of 6 hours. The mixture was then stirred at 120 ° C for 6 h. The product was degassed under vacuum and neutralized with a few drops of acetic acid. Iso-Ci7-amine-15 EO was obtained with a yield of 513 g (101% of theory) as a brownish, low-viscosity liquid having an amine value of 60 mg KOH / g (60 mg KOH / g theory).

Accordingly, iso-Ci7-amine-10 EO and iso-Ci7-amine-20 EO were prepared in quantitative yield, wherein in the second Ethoxilierungsschntt correspondingly less EO was used.

Example 3 - Glyphosate SL against winter wheat and soybean as a model plant

For the greenhouse tests, winter wheat (Cubus variety) or soybean (Oxford variety) were sown or potted in loamy sandy soil with a sowing depth of 1-2 cm. Once the plants had reached a height of growth of 10 to 25 cm (i.e., about 10 to 21 days after sowing), the spray liquors were applied to the plants in the spray booth.

A concentrated formulation containing glyphosate isoproylammonium dissolved in

Water and Aminalkoxylat from Example 2 was diluted with deionized water and were applied at a water application rate of 375 l / ha (140 g glyphosate / ha and

300 g of amine alkoxylate / ha). The temperatures in the 3- to 4-week trial period were between 18 - 35 ° C. During this time, the test plants were watered optimally, with the nutrient supply was via the irrigation water.

The evaluation of herbicidal activity was carried out by scoring the treated plants compared to the untreated control plants (Table 1). The rating scale ranges from 0% to 100% effect. 100% effect means complete extinction of at least the above-ground parts of the plant. In contrast, 0% means no differences between treated and untreated plants. The results in Tables 1 and 2 demonstrate the increased effectiveness of the active ingredient by adding the Aminalkoxylats.

Table 1: Increased effect of glyphosate on model plant winter wheat

 Aminal Koxylate Glyphosate Efficacy [%] Efficacy [%] Efficacy [%]

 [g / ha] after 14 days after 21 days after 28 days

- a) 140 64 73 73 C 16/18 amine 15 EO ^a >< ^b > 140 68 78 78 iso-C 7 -amine-10 EO 140 95 100 100 iso-C 17-amine-15 EO 140 95 100 100 iso-C 17-amine-20 EO 140 93 100 100

- a) 280 71 81 81

C16 / 18-amine-15 EO ^a >< ^b > 280 86 100 100 iso-Ci7-amine-10 EO 280 95 100 100 iso-Ci7-amine-15 EO 280 95 100 100 iso-Ci7-amine-20 EO 280 94 100 100 a) Comparative experiment, not according to the invention, b) Genamine® T-150, commercially available from Clariant, Germany.

Table 2: Increased effect of glyphosate on model plant soybean

 a) Comparative experiment, not according to the invention, b) Genamine® T-150, commercially available from Clariant, Germany.

Example 4 - Rainfastness

 Four plants of corn and winter wheat respectively were treated with 560 / ha glyphosate isopropylammonium salt and 300 g / ha amine alkoxylate. After 1, 5 or 3 hours after this treatment, the plants were rained for 20 minutes with 100 L of water at a pressure of 3.33 bar and a speed of 2.8 m / s. The plants were then placed in the greenhouse and scored after 14 and 21 days as in Example 3. For comparison, Genamine® T-150 was used (Ci6 / i8-amine ethoxylate with 15 EO units, commercially available from Clariant).

 Tables 7 and 8 show that sprinkling removes less glyphosate from the plant so that efficacy remains high even after irrigation.

Table 7: Efficacy [%] after 14 days Aminalkoxylat Without irrigation 1, 5 h irrigation 3 h

 Irrigation by application after application

No application ^a > corn 0 - -

Ci6 / 18-amine-15 EO ^a >< ^b > maize 86 45 55 iso-Ci7-amine-15 EO maize 93 61 80

No application ^a > Wheat 0 - -

Ci6 / 18-amine-15 EO ^a >< ^b > Wheat 89 55 76 iso-Ci7-amine-15 EO Wheat 93 83 90 a) Comparison test, not according to the invention, b) Genamine® T-150, commercially available from Clariant, Germany ,

Table 8: Efficacy [%] after 21 days

 a) Comparative experiment, not according to the invention, b) Genamine® T-150, commercially available Clariant, Germany.

Claims

claims

Composition comprising a pesticide and an alkoxylate, characterized in that the alkoxlate is an amine alkoxylate (A)

or a quaternized derivative (AQ)

 the Aminalkoxylats (A), wherein

R ^{1 is} a branched, aliphatic alkyl radical C17H35,

R ² , R ³ , and R ^{7 are} independently ethylene, propylene, butylene, or a mixture thereof,

R ^{4 is} H, -OH, -OR ⁶ , - [R ⁷ -O] _p -R ⁵ , C ₁ -C ₆ -alkyl or an oxygen anion,

R ^{5 is} H, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, -SO ₃ R ^a , -P (O) OR ^b OR ^c ,

-CH ₂ C0 ₂ R ^d , or -C (O) R ^e

R ⁶ is a Ci-C ₆ alkyl, C ₂ -C ₆ alkenyl, or C ₂ -C ₆ alkynyl,

R ^a and R ^d independently of one another are H, inorganic or organic cations,

R ^b and R ^{c are} independently H, inorganic or organic cations, Ci-C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl,

R ^e d C ₂₂ alkyl, C ₂ -C ₂₂ alkenyl, C ₂ -C ₂₂ alkynyl, C ₆ -C ₂₂ aryl, C ₇ -C ₂₂ alkylaryl, n, m and p independently of one another have a value of 1 to 30, and

A- is an agriculturally acceptable anion or, if R ^{4 is} an oxygen anion, A- is not present.

A composition according to claim 1 wherein R ² , R ³ and R ^{7 are} independently ethylene, ethylene and propylene, ethylene and butylene, or ethylene, propylene and butylene.

A composition according to claim 1 or 2, wherein A- is a halide, phosphate, sulfate or anionic pesticide.

A composition according to any one of claims 1 to 3, wherein R ^{4 is} H.

A composition according to any one of claims 1 to 4, wherein in the amine alkoxy (A) the sum of n and m is 2 to 40, and in its quaternized derivative (AQ) the sum of n, m and p is 3 to 80.

6. The composition according to any one of claims 1 to 5, wherein the middle degree of branching of R ^{1 is} 2.8 to 3.7.

A composition according to any one of claims 1 to 6, wherein the pesticide comprises glypho sat or glufosinate.

A composition according to any one of claims 1 to 7, wherein the pesticide comprises glyphosate or glufosinate, and additionally another pesticide.

9. Aminalkoxylat (A) according to any one of claims 1 to 6.

10. A process for preparing the Aminalkoxylats (A) or a quaternized derivative (AQ) of the Aminalkoxylats (A) according to any one of claims 1 to 6 comprising the alkoxylation of an amine R ¹ -NH2 with ethylene oxide, propylene oxide, Butyle- noxide or a mixture from that.

1 1. Amine R ¹ -NH 2, wherein R ^{1 is} a branched, aliphatic alkyl radical C17H35, wherein the average degree of branching of R ^{1 is} 2.8 to 3.7.

12. A method for controlling phytopathogenic fungi and / or undesired plant growth and / or undesired insect or Mi Iben infestation and / or

Regulation of the growth of plants, wherein the composition according to any one of claims 1 to 8 on the respective pests, their habitat or the plants to be protected from the respective pest, the soil and / or undesirable plants and / or crops and / or whose habitat has an effect.

13. Seed containing the composition according to any one of claims 1 to 8.

14. Use of the Aminalkoxylats (A) or a quaternized derivative (AQ) of Aminalkoxylats (A) according to any one of claims 1 to 6 as an aid in pesticide-containing spray liquors.