WO2014060502A1 - Active compound combinations comprising carboxamide derivatives - Google Patents

Active compound combinations comprising carboxamide derivatives Download PDF

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Publication number
WO2014060502A1
WO2014060502A1 PCT/EP2013/071694 EP2013071694W WO2014060502A1 WO 2014060502 A1 WO2014060502 A1 WO 2014060502A1 EP 2013071694 W EP2013071694 W EP 2013071694W WO 2014060502 A1 WO2014060502 A1 WO 2014060502A1
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WIPO (PCT)
Prior art keywords
methyl
plants
fluoro
cyclopropyl
pyrazole
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PCT/EP2013/071694
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English (en)
French (fr)
Inventor
Pierre Cristau
Peter Dahmen
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Bayer CropScience AG
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Bayer CropScience AG
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Priority to US14/432,815 priority Critical patent/US9801374B2/en
Priority to BR112015008797-3A priority patent/BR112015008797B1/pt
Priority to UAA201504671A priority patent/UA114822C2/uk
Priority to AU2013333916A priority patent/AU2013333916B2/en
Priority to CA2888600A priority patent/CA2888600C/en
Priority to EP13777076.4A priority patent/EP2908639A1/en
Priority to EA201590771A priority patent/EA026839B1/ru
Priority to BR122020002297-3A priority patent/BR122020002297B1/pt
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to JP2015537246A priority patent/JP6153619B2/ja
Priority to CN201380054677.7A priority patent/CN105357968A/zh
Publication of WO2014060502A1 publication Critical patent/WO2014060502A1/en
Anticipated expiration legal-status Critical
Priority to AU2017213448A priority patent/AU2017213448B2/en
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals

Definitions

  • the present invention relates to active compound combinations, in particular within a composition, which comprises (A) ) a N-cyclopropyl-N-[substituted-benzyl]-3-(difluoromethyl)-5-fluoro-l-methyl- lH-pyrazole-4-carboxamide or thiocarboxamide derivative and (B) a further herbicidally active compound or (C) a plant growth regulator and/or (D) a safener for reducing phytotoxic actions of agro- chemicals.
  • the invention relates to a method for curatively or preventively controlling the phytopathogenic fungi of plants or crops, to the use of a combination according to the invention for the treatment of seed, to a method for protecting a seed and not at least to the treated seed.
  • N-cyclopropyl-N-[substimted-benzyl]-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4- carboxamide or thiocarboxamide derivatives their preparation from commercially available materials and their use as fungicides are disclosed in WO2007/087906, WO2009/016220, WO2010/130767 and EP2251331. It is also known that these compounds can be used as fungicides and mixed with other fungicides or insecticides (cf. patent applications PCT/EP2012/001676 and PCT/EP2012/001674).
  • the useful plants When controlling unwanted organisms in crops of plants which are useful for agriculture or forestry by using pesticides, the useful plants are sometimes also damaged to a greater or lesser extent by the pesticides employed. This unwanted phytotoxic effect is encountered in particular with the use of a considerable number of herbicides in crops of useful plants such as, for example, corn, rice or cereals- and there primarily in the post-emergence application.
  • the useful plants can be protected against the phytotoxic properties of the pesticides by employing safeners or antidotes, without diminishing or substantially impairing the pesticidal activity against the harmful organisms. In some cases, even an improved pesticidal action against harmful organisms such as weeds was observed.
  • the combinations according to the invention not only bring about the additive enhancement of the spectrum of action with respect to the phytopathogen to be controlled that was in principle to be expected but achieves a synergistic effect which extends the range of action of the component (A) and of the component (B) in two ways. Firstly, the rates of application of the component (A) and of the component (B) are lowered whilst the action remains equally good. Secondly, the combination still achieves a high degree of phytopathogen control even where the two individual compounds have become totally ineffective in such a low application rate range. This allows, on the one hand, a substantial broadening of the spectrum of phytopathogens that can be controlled and, on the other hand, increased safety in use.
  • the active compound combinations according to the invention have further surprising properties which, in a wider sense, may also be called synergistic, such as, for example: broadening of the activity spectrum to other phytopathogens, for example to resistant strains of plant diseases; lower application rates of the active compounds; sufficient control of pests with the aid of the active compound combinations according to the invention even at application rates where the individual compounds show no or virtually no activity; advantageous behavior during formulation or during use, for example during grinding, sieving, emulsifying, dissolving or dispensing; improved storage stability and light stability; advantageous residue formation; improved toxicological or ecotoxicological behavior; improved properties of the plant, for example better growth, increased harvest yields, a better developed root system, a larger leaf area, greener leaves, stronger shoots, less seed required, lower phytotoxicity, mobilization of the defense system of the plant, good compatibility with plants.
  • synergistic such as, for example: broadening of the activity spectrum to other phytopathogens, for example to resistant strains of plant diseases; lower application rates of the active compounds;
  • the use of the active compound combinations or compositions according to the invention contributes considerably to keeping young cereal stands healthy, which increases, for example, the winter survival of the cereal seed treated, and also safeguards quality and yield.
  • the active compound combinations according to the invention may contribute to enhanced systemic action. Even if the individual compounds of the combination have no sufficient systemic properties, the active compound combinations according to the invention may still have this property. In a similar manner, the active compound combinations according to the invention may result in higher persistency of the fungicidal action.
  • the present invention provides a combination comprising:
  • T represents an oxygen or a sulfur atom and X is selected from the list of 2-isopropyl, 2- cyclopropyl, 2-tert-butyl, 5-chloro-2-ethyl, 5-chloro-2-isopropyl, 2-ethyl-5-fluoro, 5-fluoro-2- isopropyl, 2-cyclopropyl-5-fluoro, 2-cyclopentyl-5-fluoro, 2-fluoro-6-isopropyl, 2-ethyl-5-methyl, 2- isopropyl-5-methyl, 2-cyclopropyl-5-methyl, 2-tert-butyl-5-methyl, 5-chloro-2-(trifluoromethyl), 5- methyl-2-(trifluoromethyl), 2-chloro-6-(trifluoromethyl), 3-chloro-2-fluoro-6-(trifluoromethyl) and 2-ethyl-4,5-dimethyl, or an agrochemically acceptable salt thereof,
  • Suitable as combination partners for the active N-cyclopropyl-N-[substituted-benzyl]-3- (difluoromethyl)-5-fluoro-l -methyl- lH-pyrazole-4-carboxamide or thiocarboxamide derivatives of formula (I) in formulations of mixtures or in tank-mixes are, for example, known, preferably herbicidal- ly active compounds whose action is based on the inhibition of, for example, acetolactate synthase, ace- tyl-coenzyme-A carboxylase, PS I, PS II, HPPDO, phytoene desaturase, protoporphyrinogen oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate 3-phosphate synthetase.
  • herbicides known from the literature and also safeners which may be combined with the N-cyclopropyl-N-[substimted-benzyl]-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4- carboxamide or thiocarboxamide derivatives of formula (I) are the active compounds indicated herein (note: the compounds are referred to either by the "common name” according to the International Organization for Standardization (ISO) or by the chemical name, if appropriate together with a customary code number):
  • acetochlor acibenzolar-S-methyl; acifluorfen(-sodium); aclonifen; AD-67; AKH 7088, i.e. [[[l-[5-[2- chloro-4-(trifluoromethyl)phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and methyl [[[l-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]- amino]oxy]acetate; alachlor; alloxydim(-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; aminopyralid; amitrol; AMS, i.e.
  • ammonium sulfamate ancimidol
  • anilofos asulam
  • atrazine avi- glycine
  • azafenidin azimsulfuron (DPX-A8947); aziprotryn
  • barban BAS 516 H, i.e.
  • Herbicides of Group (B) which are suitable for combination with the N-cyclopropyl-N- [substituted- benzyl]-3-(difluoromethyl)-5-fluoro- l -methyl-lH-pyrazole-4-carboxamide or thiocarboxamide derivatives of formula (I) are preferably selected from the group consisting of:
  • (B-l . l) phenoxyphenoxy- and benzyloxyphenoxycarboxylic acid derivatives for example (B- 1.1.1 ) methyl 2-(4-(2,4-dichlorophenoxy)phenoxy)propionate (diclofop-methyl), (B- 1.1.2) methyl 2-(4-(4-bromo-2-chlorophenoxy)phenoxy)propionate (DE-A 26 01 548), (B- l .1.3) methyl 2-(4-(4-bromo-2-fluorophenoxy)phenoxy)propionate (US 4,808,750), (B-l .1.4) methyl 2-(4-(2-chloro-4-trifluoromethylphenoxy)phenoxy)- propionate (DE-A 24 33 067), (B- l .1.5) methyl 2-(4-(2-fluoro-4-trifluoromethylphen- oxy)phenoxy)propionate (US 4,808,750), (B- l .1.6)
  • (B-l .3) "bicyclic" heteroaryloxyphenoxyalkanecarboxylic acid derivatives, for example (B- l .3.1) quizalofop-methyl, (B- l .3.2) quizalofop-ethyl, (B-l .3.3) quizalofop-P- methyl, (B- l .3.4) quizalofop-P-ethyl, (B-l .3.5) methyl 2-(4-(6-fluoro-2- quinoxalyloxy)phenoxy)propionate (see J. Pest. Sci.
  • (B-2) Herbicides from the group of the sulfonylureas, such as pyrimidinyl- or triazinylaminocar- bonyl[benzene-, -pyridine-, -pyrazole-, -thiophene- and -(alkyl- sulfonyl)alkylamino]sulfamides, with preferred substituents on the pyrimidine ring or the tria- zine ring selected from alkoxy, alkyl, haloalkoxy, haloalkyl, halogen or dimethylamino, it being possible to combine all substituents independently of one another and with preferred substituents in the benzene, pyridine, pyrazole, thiophene or (alkylsulfonyl)alkylamino moiety selected from alkyl, alkoxy, halogen, nitro, alkoxycarbonyl, aminocarbonyl, alkylaminocar- bony
  • B-2.1 phenyl- and benzylsulfonylureas and related compounds, for example (B-2.1.1) chlor- sulfuron, (B-2.1.2) chlorimuron-ethyl, (B-2.1.3) metsulfuron-methyl, (B-2.1.4) triasul- furon, (B-2.1.5) sulfometuron-methyl, (B-2.1.6) tribenuron-methyl, (B-2.1.7) bensul- furon-methyl, (B-2.1.8) primisulfuron-methyl, (B-2.1.9) 3-(4-ethyl-6-methoxy- 1,3,5- triazin-2-yl)- 1 -(2,3-dihydro- 1 , 1 -dioxo-2-methylbenzo[b]thiophene-7-sulfonyl)urea (EP-A 0 079 83), (B-2.1.10) 3-(4-ethoxy-6-ethyl-l-
  • B-2.3 pyrazolylsulfonylureas, for example (B-2.3.1) pyrazosulfuron-ethyl, (B-2.3.2) methyl halosulfuron-methyl, (B-2.3.3) methyl 5-(4,6-dimethylpyrimidin-2-yl- carbamoylsulfamoyl)-l-(2-pyridyl)pyrazole-4-carboxylate (NC-330, see Brighton Crop Prot.
  • B-2.4 sulfonediamide derivatives, for example (B-2.4.1) amidosulfuron and (B-2.4.2) its structural analogs (EP-A 0 131 258 and Z. Pfl. Krankh. Pfl. Schutz, special issue XII, 489-497 (1990));
  • (B-2.5) pyridylsulfonylureas for example (B-2.5.1) nicosulfuron, (B-2.5.2) rimsulfuron, (B-2.5.3) flupyrsulfuron-methyl, (B-2.5.4) flupyrsulfuron-methyl-sodium, (B-2.5.5) 3-(4,6-dimethoxypyrimidin-2-yl)-l-(3-N-methylsulfonyl-N-methylaminopyridin-2- yl)sulfonylurea or its salts (DE-A 40 00 503 and DE-A 40 30 577), (B-2.5.6) fla- zasulfuron, (B-2.5.7) trifloxysulfuron-sodium, (B-2.5.8) flucetosulfuron;
  • (B-2.7) imidazolylsulfonylureas for example (B-2.7.1) sulfosulfuron, (B-2.7.2) imazosulfu- ron, (B-2.7.3) 2-chloro-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-6- propylimidazo[l,2-b]pyridazine-3-sulfonamide;
  • B-2.8 phenylaminosulfonylureas, for example (B-2.8.1) cyclosulfamuron, (B-2.8.2) ortho- sulfamuron;
  • (B-3) Chloroacetanilides for example (B-3.1) acetochlor, (B-3.1) alachlor, (B-3.2) butachlor, (B-3.3) dimethachlor, (B-3.4) dimethenamid, (B-3.5) dimethanamid-P metazachlor, (B-3.6) metolachlor, (B-3.7) S-metolachlor, (B-3.8) pethoxamid, (B-3.9) pretilachlor, (B-3.10) propachlor, (B-3.11) propisochlor and (B-3.12)thenylchlor;
  • B-4 Thiocarbamates, for example (B-4.1) S-ethyl ⁇ , ⁇ -dipropylthiocarbamate (EPTC), (B-4.2) S- ethyl ⁇ , ⁇ -diisobutylthiocarbamate (butylate), (B-4.3) cycloate, (B-4.4) dimepiperate, (B-4.5) esprocarb, (B-4.6) molinate, (B-4.7) orbencarb, (B-4.8) pebulate, (B-4.9) prosulfocarb, (B-4.10) thiobencarb, (B-4.11) tiocarbazil, (B-4.12) tri-allate and (B-4.13) vernolate;
  • EPTC S-ethyl ⁇ , ⁇ -dipropylthiocarbamate
  • B-4.2 S- ethyl ⁇ , ⁇ -diisobutylthiocarbamate (butylate),
  • Cyclohexanedione oximes for example (B-5.1) alloxydim, (B-5.2) butroxydim, (B-5.3) clethodim, (B-5.4) cloproxydim, (B-5.5) cycloxydim, (B-5.6) profoxydim, (B-5.7) sethox- ydim, (B-5.8) tepraloxydim and (B-5.9) tralkoxydim;
  • (B-6) Imidazolinones, for example (B-6.1) imazamethabenz-methyl, (B-6.2) imazapic, (B-6.3) ima- zamox, (B-6.4) imazapyr, (B-6.5) imazaquin and (B-6.6) imazethapyr; (B-7) Triazolopyrimidinesulfonamide derivatives, for example (B-7.1) chloransulam-methyl, (B-7.2) diclosulam, (B-7.3) florasulam, (B-7.4) flumetsulam, (B-7.5) metosulam, (B-7.6) pe- noxsulam (B-7.7) and pyroxsulam;
  • B-8.8 Benzoylcyclohexanediones, for example (B-8.1) sulcotrione, (B-8.2) 2-(2-nitrobenzoyl)-4,4-di- methylcyclohexane-l,3-dione (EP-A 0 274 634), (B-8.3) 2-(2-nitro-3-methylsulfonylbenzoyl)- 4,4-dimethylcyclohexane-l,3-dione (WO 91/13548), (B-8.4) mesotrione, (B-8.5) 2-[2-chloro- 3-(5-cyanomethyl-4,5-dihydroisoxazol-3-yl)-4-(ethylsulfonyl)benzoyl]-l,3-cyclohexanedione, (B-8.6) 2-[2-chloro-3-(5-cyanomethyl-4,5-dihydroisoxazol-3-yl)-4-(
  • B-10.10 Benzoylpyrazoles, for example (B-10.1) benzofenap, (B-10.2) pyrazolynate, (B-10.3) pyra- zoxyfen, (B-10.4) 5-hydroxy-l-methyl-4-[2-(methylsulfonyl)-4- trifluoromethylbenzoyl]pyrazole (WO 01/74785), (B-10.5) l-ethyl-5-hydroxy-4-[2- (methylsulfonyl)-4-trifluoromethylbenzoyl]pyrazole (WO 01/74785), (B-10.6) l,3-dimethyl-5- hydroxy-4-[2-(methylsulfonyl)-4-trifluoromethylbenzoyl]pyrazole (WO 01/74785), (B-10.7) pyrasulfotole, (B- 10.8) 5-hydroxy- 1 -methyl-4-[-2-chloro-3-(4,5-dihydroisoxazol-3-yl)
  • B-12 Triazolinones, for example (B-12.1) amicarbazone, (B- 12.2) azafenidin, (B-12.3) carfentra- zone-ethyl, (B- 12.4) sulfentrazone, (B- 12.5) bencarbazone;
  • B- 13 Phosphinic acids and derivatives, for example (B- 13.1) bilanafos, (B- 13.2) glufosinate, (B- 13.3) glufosinate-ammonium;
  • B- 14 Glycine derivatives, for example (B-14.1) glyphosate, (B- 14.2) glyphosate-sodium, (B- 14.3) glyphosate-isopropylammonium,
  • N-(phosphonomethyl)glycine trimesium salt (sulfosate);
  • B- 15 Pyrimidinyloxypyridinecarboxylic acid derivatives and pyrimidinyloxybenzoic acid derivatives, for example (B-l 5.1) benzyl 3-(4,6-dimethoxypyrimidin-2-yl)oxypyridine-2- carboxylate (EP-A 0 249 707), (B-l 5.2) methyl 3-(4,6-dimethoxypyrimidin-2- yl)oxypyridine-2-carboxylate (EP-A 0 249 707), (B- 15.3) l-(ethoxycarbonyloxyethyl) 2,6- bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate (EP-A 0 472 1 13), (B- 15.4) bispyribac- sodium, (B- 15.5) pyribambenz-isopropyl, (B- 15.6) pyribambenz-propyl, (B- 15.7) pyriben- zoxim, (B-l
  • B-17 Triazinones, for example (B-17.1) hexazinone, (B-17.2) metamitron, (B-17.3) metribuzin;
  • B-18 Pyridinecarboxylic acids, for example (B-18.1) aminopyralid, (B-18.2) clopyralid, (B-18.3) fluroxypyr, (B-18.4) picloram and (B-18.5) triclopyr;
  • (B-19) pyridines for example (B-19.1) dithiopyr and (B-19.2) thiazopyr;
  • (B-21) 1,3,5-Triazines for example (B-21.1) ametryn, (B-21.2) atrazine, (B-21.3) cyanazine, (B-21.4) dimethametrin, (B-21.5) prometon, (B-21.6) prometryn, (B-21.7) propazine, (B-21.8) simazine, (B-21.9) symetryn, (B-21.10) terbumeton, (B-21.11) terbuthylazine, (B-21.12) terbutryn and (B-21.13) trietazine;
  • the herbicides of Groups (B-l) to (B-23) are known, for example, from the respective abovemen- tioned publications and from "The Pesticide Manual", The British Crop Protection Council, 14 th Edition, 2006, or the e-Pesticide Manual, Version 4.0, British Crop Protection Council 2006 or else from the "Compendium of Pesticide Common Names”.
  • herbicides listed above according to structural types, also share structure-overlapping characteristics when it comes to their mode of action, and some are also similar to one another with respect to their behaviour in the combinations with the N-cyclopropyl-N-[substituted-benzyl]-3- (difluoromethyl)-5-fluoro- 1 -methyl- lH-pyrazole-4-carboxamide or thiocarboxamide derivatives of formula (I).
  • Suitable herbicides of Group (B) which can be combined with the N-cyclopropyl-N-[substituted- benzyl]-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide or thiocarboxamide derivatives of formula (I) are particularly preferably those selected from the group consisting of
  • (B-A.1) Herbicides which prevent or inhibit the formation of chlorophyll (herbicides acting as bleachers), for example (B-A.1.1) Inhibitors of hydroxyphenylpyruvate dioxygenase (HPPD inhibitors), such as (B- A.1.1.1) sulcotrione, (B-A.1.1.2) 2-(2-nitrobenzoyl)-4,4-dimethylcyclohexane-l,3- dione (EP-A 0 274 634), (B-A.1.1.3) 2-(2-nitro-3-methylsulfonylbenzoyl)-4,4- dimethylcyclohexane-l,3-dione (WO 91/13548), (B-A.1.1.4) mesotrione, (B-A.1.1.5) 2-[2-chloro-3-(5-cyanomethyl-4,5-dihydroisoxazol-3-yl)-4-(ethylsulfonyl)benzoy
  • (B-A.1.2) inhibitors of carotenoid biosynthesis including phytoene desaturase inhibitors, such as, for example (B-A.1.2.1) norflurazon, (B-A.1.2.2) beflubutamide, (B-A.1.2.3) flu- ridone, (B-A.1.2.4) flurochloridone, (B-A.1.2.5) flurtamone, (B-A.1.2.6) amitrole, (B- A.1.2.7) clomazone, (B-A.1.2.8) aclonifen, (B-A.1.2.9) diflufenican and (B-A.1.2.10) picolinafen,
  • phytoene desaturase inhibitors such as, for example (B-A.1.2.1) norflurazon, (B-A.1.2.2) beflubutamide, (B-A.1.2.3) flu- ridone, (B-A.1.2.4) flurochloridone, (B-A.1.2.5) flurtamone,
  • DHP synthase inhibitors of dihydropteroate synthase (DHP synthase), such as, for example (B- A.1.3.1) asulam;
  • (B-A.2.1) inhibitors of acetolactate synthase in plants such as, for example, (B-A.2.1.1) chlor- sulfuron, (B-A.2.1.2) chlorimuron-ethyl, (B-A.2.1.3) metsulfuron-methyl, (B-A.2.1.4) triasulfuron, (B-A.2.1.5) sulfometuron-methyl, (B-A.2.1.6) tribenuron-methyl, (B- A.2.1.7) bensulfuron-methyl, (B-A.2.1.8) primisulfuron-methyl, (B-A.2.1.9) 3-(4- ethyl-6-methoxy- 1 ,3,5-triazin-2-yl)- 1 -(2,3-dihydro- 1 , 1 -dioxo-2-methylbenzo- [b]thiophene-7-sulfonyl)urea (EP-A 0 796 83), (B-
  • (B-A.3.1) inhibitors of acetyl-coenzyme A carboxylase for example (B-A.3.1.1) di- clofop-methyl, (B-A.3.1.1a) diclofop-P-methyl, (B-A.3.1.2) methyl 2-(4-(4-bromo-2- chlorophenoxy)phenoxy)propionate (DE-A 26 01 548), (B-A.3.1.3) methyl 2-(4-(4- bromo-2-fluorophenoxy)phenoxy)propionate (US-A 4,808,750), (B-A.3.1.4) methyl 2-(4-(2-chloro-4-trifluoromethylphenoxy)phenoxy)propionate (DE-A 24 33 067), (B- A.3.1.5) methyl 2-(4-(2-fluoro-4-trifluoromethylphenoxy)phenoxy)propionate (US 4,808,750), (B-A.3.1.6) methyl 2-(4-(4-(4-
  • (B-A.4.1) inhibitors of cell wall synthesis (cellulose synthesis inhibitors), for example (B- A.4.1.1) dichlobenil, (B-A.4.1.2) chlorthiamid, (B-A.4.1.3) isoxaben, (B-A.4.1.4) flupoxam and (B-A.4.1.5) triaziflam;
  • (B-A.4.2) inhibitors of microtubuli inhibitors of the formation of microtubuli and their organisation
  • DCPA chlorthal-dimethyl, (B-A.4.2.13) chlorpropham, (B-A.4.2.14) propham, (B-A.4.2.15) carbetamide, (B-A.4.2.11
  • (B-A.4.3) inhibitors of mitosis or microtubuli organisation such as (B-A.4.3.1) chlorpropham, (B-A.4.3.2) propham, (B-A.4.3.3) carbetamide; (B-A.4.4) inhibitors of the synthesis of very long-chain fatty acids (VLCFAs), such as (B- A.4.4.1) acetochlor, (B-A.4.4.2) alachlor, (B-A.4.4.3) butachlor, (B-A.4.4.4) di- methachlor, (B-A.4.4.5) dimethenamid, (B-A.4.4.6) metazachlor, (B-A.4.4.7) metolachlor, (B-A.4.4.8) S-metolachlor, (B-A.4.4.9) pethoxamid, (B-A.4.4.10) preti- lachlor, (B-A.4.4.1 1) propachlor, (B-A.4.4.12) propisochlor,
  • (B-B. l) Herbicides which negatively affect the electron transport in the photo system I, such as (B- B. l . l) diquat, (B-B.1.1a) diquat dibromide, (B-B.1.2) paraquat, (B-B.1.2a) paraquat dichlo- ride;
  • (B-B.3) Destroyers of the cell membranes in plants, such as (B-B.3.1) DNOC, (B-B.3.2) dinoseb and (B-B.3.3) dinoterb;
  • the herbicide Groups (B-A) and (B-B) and their subgroups comprise active compounds from various structural classes.
  • the respective herbicides from the same structural class of a group or subgroup of the Groups (B-A) and (B-B) mentioned thus form in each case a more preferred subgroup within the respective mechanism-of-action or phenomenological group.
  • compositions comprising a combination of a compound (Al), (A2), (A3), (A4), (A5), (A6), (A7), (A8), (A9), (A10), (Al l), (A12), (A13), (A14), (A15), (A16) (A17), (A18), (A19) or (A20) with one or more active compounds from the group of the herbicide groups (B-
  • Suitable plant growth regulators are compounds or mixtures which may have an influence on the germination, growth, maturation and ripening or the development of plants or their fruits. These plant growth regulators may be divided in certain subclasses as exemplified below.
  • (C- l) Antiauxins such as (C- 1.1) clofibrin [2-(4-Chlorphenoxy)-2-methylpropansaure] and (C- 1.2) 2,3,5-tri-iodobenzoic acid;
  • (C-2) Auxins such as (C-2.1) 4-CPA (4-chlorophenoxyacetic acid), (C-2.2) 2,4-D (2,4- dichlorophenoxyacetic acid), (C-2.3) 2,4-DB [4-(2,4-dichlorophenoxy)butanoic acid], (C-2.4) 2,4-DEP ⁇ tris[2-(2,4-dichlorophenoxy)ethyl]phosphite ⁇ , (C-2.5) dichlorprop, (C-2.6) fenoprop, (C-2.7) IAA ( ⁇ -indoleacetic acid), (C-2.8) IBA (4-indol-3-ylbutanoic acid), (C-2.9) naphthalineacetamide, (C-2.10) a-naphthalineacetic acid, (C-2.1 1) 1-naphthol, (C-2.12) naph- thoxyacetic acid, (C-2.13) potassium naphthenate, (C-2.1
  • Cytokinins such as (C-3.1) 2iP [N-(3-methylbut-2-enyl)- lH-purin-6-amine], (C-3.2) ben- zyladenine, (C-3.3) kinetin, (C-3.3) zeatin;
  • (C-4) Defoliants such as (C-4.1) calcium cyanamide, (C-4.2) dimethipin, (C-4.3) endothal, (C-4.4) ethephon, (C-4.5) merphos, (C-4.6) metoxuron, (C-4.7) pentachlorophenol, (C-4.8) thidi- azuron, (C-4.9) tribufos;
  • Ethylene inhibitors such as (C-5.1) aviglycine, (C-5.2) aviglycine-hydrochloride, (C-5.3) 1 - methylcyclopropene;
  • C-6 Ethylene generators, such as (C-6.1) ACC (1-aminocyclopropanecarboxylic acid), (C-6.2) et messagingl, (C-6.3) ethephon, (C-6.4) glyoxime;
  • (C-8) Growth inhibitors such as (C-8.1) abscisic acid, (C-8.2) ancymidol, (C-8.3) butralin, (C-8.4) carbaryl, (C-8.5) chlo ⁇ honium or (C-8.5 A) its chloride, (C-8.6) chlorpropham, (C-8.7) dikegulac, (C-8.8) dikegulac-sodium, (C-8.9) flumetralin, (C-8.10) fluoridamid, (C-8.11) fos- amine, (C-8.12) glyphosine, (C-8.13) isopyrimol, (C-8.14) jasmonic acid, (C-8.15) maleic acid hydrazide or (C-8.15A) its potassium salt, (C-8.16) mepiquat or (C-8.16A) its chloride, (C- 8.17) piproctanyl or (C-8.17A) its bromide, (C-8.18) prohydro
  • C-9) Morphactins such as (C-9.1) chlorfluren, (C-9.2) chlorflurenol, (C-9.3) chlorflurenol-methyl, (C-9.4) dichloroflurenol, (C-9.5) flurenol;
  • C-10) Growth retardants/modifiers such as (C-10.1) chlormequat, (C-10.2) chlormequat-chloride, (C-10.3) daminozide, (C-10.4) flurprimidol, (C-10.5) mefluidide, (C-10.6) mefluidide- diolamine, (C-10.7) paclobutrazol, (C-10.8) cyproconazole, (C-10.9) tetcyclacis, (C-10.10) uniconazole, (C-10.11) uniconazole-P;
  • (C-l 1) Growth stimulants such as (C- 1 1.1) brassinolide, (C-l 1.2) forchlorfenuron, (C-l 1.3) hymex- azol, (C-l 1.4) 2-amino-6-oxypurine derivatives, (C-l 1.5) indolinone derivates, (C-l 1.6) 3,4- disubstituted maleimide derivatives and (C- 11.7) azepinone derivatives;
  • (C-12) non-classified PGRs such as (C-12.1) benzofluor, (C-12.2) buminafos, (C-12.3) carvone, (C- 12.4) ciobutide, (C-12.5) clofencet, (C-12.6) clofence-potassium, (C-12.7) cloxyfonac, (C- 12.8) cloxyfonac-sodium, (C-12.9) cyclanilide, (C-12.10) cycloheximide, (C-12.11) epocholeone, (C-12.12) ethychlozate, (C-12.13) ethylene, (C-12.14) fenridazon, (C-12.15) heptopargil, (C-12.16) holosulf, (C-12.17) inabenfide, (C-12.18) karetazan, (C-12.19) bleiar- senat, (C- 12.
  • (C-13) and other PGRs such as (C-13.1) 2,6-diisopropylnaphthaline, (C-13.2) cloprop, (C-13.3) ethyl 1-naphthylacetate, (C-l 3.4) isoprothiolane, (C-l 3.5) MCPB-ethyl [ethyl 4-(4-chloro-o- tolyloxy)butanoate], (C-13.6) N-acetylthiazolidin-4-carboxylic acid, (C-l 3.7) «-decanol, (C- 13.8) pelargonic acid, (C-13.9) N-phenylphthalimic acid, (C-13.10) tecnazene, (C-13.11) tri- acontanol, (C-13.12) 2,3-dihydro-5,6-diphenyl-l,4-oxathiine, (C-13.13) 2-cyano-3-(2,4- dichlor
  • chlormequat Preferably chlormequat, chlormequat-chlorid, cyclanilide, dimethipin, ethephon, flumetralin, flur- primidol, inabenfide, mepiquat, mepiquat-chlorid, 1-methylcyclopropen, paclobutrazol, prohexadion- calcium, prohydrojasmon, tribufos, thidiazuron, trinexapac, trinexapac-ethyl or uniconazol are used as mixing partner for N-cyclopropyl-N-[substituted-benzyl]-3-(difluoromethyl)-5-fluoro-l-methyl-lH- pyrazole-4-carboxamide or thiocarboxamide derivatives of formula (I).
  • the safener of Group (D) is generally a crop plant compatibility-improving compound selected from the group consisting of (D-l) 4-dichloroacetyl-l-oxa-4-azaspiro[4.5]decane (AD-67), (D-2) dicyclo- non, (D-3) benoxacor, (D-4) cloquintocet-mexyl (cf.
  • EP-A-0 086750 EP-A-0 094349, EP-A-0191736, EP-A-0492366), (D-5) cumyluron, (D-6) cyometrinil, (D-7) 2,4- dichlorophenoxyacetic acid (2,4-D), (D-8) 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (D-9) dai- muron (dymron), (D-10) dicamba, (D-l l) dimepiperate, (D-l 2) 2,2-dichloro-N-(2-oxo-2-(2- propenylamino)ethyl)-N-(2-propenyl)acetamide (DKA-24), (D-l 3) dichlormid, (D-l 4) fenclorim, (D- 15) fenchlorazole-ethyl (cf.
  • Preferred safeners of Group (D) are (D-4) cloquintocet-mexyl, (D-5) cumyluron, (D-9) dymron, (D-l 1) dimepiperate, (D-14) fenclorim, (D- 15) fenchlorazol-ethyl, (D-18) furilazole, (D- 19) isoxadifen-ethyl, (D-23) mefenpyr-diethyl, (D-62) N- ⁇ [4-(cyclopropylcarbamoyl)phenyl]sulfonyl ⁇ -2- methoxybenzamide (cyprosulfamide) and (D-63) N- ⁇ [4-(cyclopropylcarbamoyl)phenyl]sulfonyl ⁇ -2- methoxy-5-methylbenzamide.
  • this invention is directed to mixtures comprising the compound (Al), (A2), (A3), (A4), (A5), (A6), (A7), (A8), (A9), (A10), (Al l), (A12), (A13), (A14), (A15), (A16) (A17), (A18), (A19) or (A20) as compound of formula (I) and one component (B), (C) or (D).
  • this invention is directed to mixtures comprising the compound (Al), (A2), (A3), (A4), (A5), (A6), (A7), (A8), (A9), (A10), (Al l), (A12), (A13), (A14), (A15), (A16) (A17), (A18), (A19) or (A20) as compound of formula (I) and at least one compound selected among the list LI consisting of (B-A.1.1.1), (B-A. l .1.2), (B-A. l .1.3), (B-A. l .1.4), (B-A.1.1.5),(B-A.1.1.6), (B-A.1.1.7), (B-A.
  • this invention is directed to mixtures comprising the compound (A2), (A5), (A7) or (A 12), particularly (A5), as compound of formula (I) and at least one compound selected among the list LI as herein described. If the active compounds in the active compound combinations according to the invention are present in certain weight ratios, the synergistic effect is particularly pronounced. However, the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range.
  • the compounds (A) and (B) are present in a synergistically effective weight ratio of A:B in a range of 100: 1 to 1 : 100, preferably in a weight ratio of 50: 1 to 1 :50, more preferably in a weight ratio of 20: 1 to 1 :20, and even more preferably in a weight ratio of 10: 1 to 1 : 10.
  • active compound combinations according to the invention are applied to leaves in a dose from 0.1 to 10 000 g/ha and are applied to seeds in a dose from 2 to 200 g per 100 kg of seed.
  • Compounds (A), (B), (C) or (D) having at least one basic centre are capable of forming, for example, acid addition salts, e.g. with strong inorganic acids, such as mineral acids, e.g. perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as unsubstituted substituted, e.g. halo-substituted, C1-C4 alkanecarboxylic acids, e.g. acetic acid, saturated or unsaturated dicarboxylic acids, e.g.
  • strong inorganic acids such as mineral acids, e.g. perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid
  • strong organic carboxylic acids such as unsubstituted substituted, e.g. halo-substituted, C
  • oxalic, malonic, succinic, maleic, fumaric and phthalic acid hydroxycarboxylic acids, e.g. ascorbic, lactic, malic, tartaric and citric acid, or benzoic acid, or with organic sulfonic acids, such as unsubstituted or substituted, e.g. halo-substituted, Ci- C4alkane- or aryl-sulfonic acids, e.g. methane- or p-toluene-sulfonic acid.
  • Compounds (A), (B), (C) or (D) having at least one acid group are capable of forming, for example, salts with bases, e.g.
  • metal salts such as alkali metal or alkaline earth metal salts, e.g. sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri- lower alkylamine, e.g. ethyl-, diethyl-, triethyl- or dimethyl-propyl-amine, or a mono-, di- or tri- hydroxy-lower alkylamine, e.g. mono-, di- or tri-ethanolamine.
  • corresponding internal salts may optionally be formed. In the context of the invention, preference is given to agrochemically advantageous salts.
  • any reference to the free compounds (A), (B), (C) or (D) or to their salts should be understood as including also the corresponding salts or the free compounds (A), (B), (C) or (D), respectively, where appropriate and expedient.
  • the equivalent also applies to tautomers of compounds (A), (B), (C) or (D) and to their salts.
  • the expression “combination” stands for the various combinations of compounds (A) and compounds (B), (C) and/or (D), for example in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active compounds, such as a "tank-mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • the order of applying the compounds (A) and compounds (B), (C) or (D) is not essential for working the present invention.
  • the "combination" of compounds (A) and compounds (B), (C) and/or (D) is a composition comprising compound (A) and compound (B), (C) and/or (D).
  • the present invention furthermore relates to compositions for combating/controlling undesirable microorganisms comprising the active compound combinations according to the invention.
  • the compositions are fungicidal compositions comprising agriculturally suitable auxiliaries, solvents, carriers, surfactants or extenders.
  • the invention relates to a method of combating undesirable microorganisms, characterized in that the active compound combinations according to the invention are applied to the phytopathogen- ic fungi and/or their habitat.
  • carrier is to be understood as meaning a natural or synthetic, organic or inorganic substance which is mixed or combined with the active compounds for better applicability, in particular for application to plants or plant parts or seeds.
  • the carrier which may be solid or liquid, is generally inert and should be suitable for use in agriculture.
  • Suitable solid or liquid carriers are: for example ammonium salts and natural ground minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral oils and vegetable oils, and also derivatives thereof. It is also possible to use mixtures of such carriers.
  • natural ground minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
  • ground synthetic minerals such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral oils and vegetable oils, and also derivatives thereof. It is also possible to use mixtures of such carriers.
  • Solid carriers suitable for granules are: for example crushed and fractionated natural minerals, such as calcite, marble, pumice, sepiolite, dolomite, and also synthetic granules of inorganic and organic meals and also granules of organic material, such as sawdust, coconut shells, maize cobs and tobacco stalks.
  • Suitable liquefied gaseous extenders or carriers are liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants, such as butane, propane, nitrogen and C0 2 .
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules and latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, or else natural phospholipids, such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other possible additives are mineral and vegetable oils and waxes, optionally modified.
  • Suitable liquid solvents are essentially: aromatic compounds, such as xylene, toluene or al- kylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and also ethers and esters thereof, ketones, such as acetone, methyl ethyl ketone, methyl isobu- tyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulph- oxide, and also water.
  • aromatic compounds such as xylene, toluene or al- kylnaphthalenes
  • chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlor
  • compositions according to the invention may comprise additional further components, such as, for example, surfactants.
  • surfactants are emulsifiers, dispersants or wetting agents having ionic or nonionic properties, or mixtures of these surfactants. Examples of these are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polyconden- sates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates.
  • the presence of a surfactant is required if one of the active compounds and/or one of the inert carriers is insoluble in water and when the application takes place in water.
  • the proportion of surfactants is between 5 and 40 per cent by weight of the composition according to the invention.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments for example iron oxide, titanium oxide, Prussian blue
  • organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • additional components may also be present, for example protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, sequestering agents, complex formers.
  • the active compounds can be combined with any solid or liquid additive customarily used for formulation purposes.
  • compositions according to the invention comprise between 0.05 and 99 per cent by weight, 0.01 and 98 per cent by weight, preferable between 0.1 and 95 per cent by weight, particularly preferred between 0.5 and 90 per cent by weight of the active compound combination according to the invention, very particularly preferable between 10 and 70 per cent by weight.
  • the active compound combinations or compositions according to the invention can be used as such or, depending on their respective physical and/or chemical properties, in the form of their formulations or the use forms prepared therefrom, such as aerosols, capsule suspensions, cold-fogging concentrates, warm-fogging concentrates, encapsulated granules, fine granules, flowable concentrates for the treatment of seed, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emul- sions, water-in-oil emulsions, macrogranules, microgranules, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible liquids, foams, pastes, pesticide-coated seed, suspension concentrates, suspoemulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble granules or tablets, water-soluble powder
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds or the active compound combinations with at least one additive.
  • Suitable additives are all customary formulation auxiliaries, such as, for example, organic solvents, extenders, solvents or diluents, solid carriers and fillers, surfactants (such as adjuvants, emulsifiers, dispersants, protective colloids, wetting agents and tackifiers), dispersants and/or binders or fixatives, preservatives, dyes and pigments, defoamers, inorganic and organic thickeners, water repellents, if appropriate siccatives and UV stabilizers, gibberellins and also water and further processing auxiliaries.
  • further processing steps such as, for example, wet grinding, dry grinding or granulation may be required.
  • compositions according to the invention do not only comprise ready-to-use compositions which can be applied with suitable apparatus to the plant or the seed, but also commercial concentrates which have to be diluted with water prior to use.
  • the active compound combinations according to the invention can be present in (commercial) formulations and in the use forms prepared from these formulations as a mixture with other (known) active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners and Semiochemicals.
  • active compounds such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners and Semiochemicals.
  • the treatment according to the invention of the plants and plant parts with the active compounds or compositions is carried out directly or by action on their surroundings, habitat or storage space using customary treatment methods, for example by dipping, spraying, atomizing, irrigating, evaporating, dusting, fogging, broadcasting, foaming, painting, spreading-on, watering (drenching), drip irrigating and, in the case of propagation material, in particular in the case of seeds, furthermore as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for slurry treatment, by in- crusting, by coating with one or more layers, etc. It is furthermore possible to apply the active compounds by the ultra-low volume method, or to inject the active compound preparation or the active compound itself into the soil.
  • the invention furthermore comprises a method for treating seed.
  • the invention furthermore relates to seed treated according to one of the methods described in the preceding paragraph.
  • the active compounds or compositions according to the invention are especially suitable for treating seed.
  • a large part of the damage to crop plants caused by harmful organisms is triggered by an infection of the seed during storage or after sowing as well as during and after germination of the plant. This phase is particularly critical since the roots and shoots of the growing plant are particularly sensitive, and even small damage may result in the death of the plant. Accordingly, there is great interest in protecting the seed and the germinating plant by using appropriate compositions.
  • the present invention also relates in particular to a method for protecting seed and germinating plants against attack by phytopathogenic fungi by treating the seed with a composition according to the invention.
  • the invention also relates to the use of the compositions according to the invention for treating seed for protecting the seed and the germinating plant against phytopathogenic fungi.
  • the invention relates to seed treated with a composition according to the invention for protection against phytopathogenic fungi.
  • compositions according to the invention treatment of the seed with these compositions not only protects the seed itself, but also the resulting plants after emergence, from phytopathogenic fungi. In this manner, the immediate treatment of the crop at the time of sowing or shortly thereafter can be dispensed with.
  • the mixtures according to the invention can be used in particular also for transgenic seed where the plant growing from this seed is capable of expressing a protein which acts against pests.
  • the active compound combinations or compositions according to the invention even by the expression of the, for example, insecticidal protein, certain pests may be controlled.
  • a further synergistic effect may be observed here, which additionally increases the effectiveness of the protection against attack by pests.
  • compositions according to the invention are suitable for protecting seed of any plant variety employed in agriculture, in the greenhouse, in forests or in horticulture or viticulture.
  • this takes the form of seed of cereals (such as wheat, barley, rye, triticale, millet, oats), maize (corn), cotton, soya bean, rice, potatoes, sunflowers, beans, coffee, beets (e.g. sugar beets and fodder beets), peanuts, oilseed rape, poppies, olives, coconuts, cacao, sugar cane, tobacco, vegetables (such as tomatoes, cucumbers, onions and lettuce), lawn and ornamental plants (also see below).
  • the treatment of seeds of cereals (such as wheat, barley, rye, triticale, and oats), maize (corn) and rice is of particular importance.
  • transgenic seed As also described further below, the treatment of transgenic seed with the active compound combinations or compositions according to the invention is of particular importance.
  • the heterologous gene in transgenic seed can originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • this heterologous gene is from Bacillus sp., the gene product having activity against the European corn borer and/or the Western corn rootworm.
  • the heterologous gene originates from Bacillus thuringiensis.
  • the active compound combinations or compositions according to the invention are applied on their own or in a suitable formulation to the seed.
  • the seed is treated in a state in which it is sufficiently stable so that the treatment does not cause any damage.
  • treatment of the seed may take place at any point in time between harvesting and sowing.
  • the seed used is separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits.
  • seed which has been harvested, cleaned and dried to a moisture content of less than 15 % by weight.
  • the amount of the composition according to the invention applied to the seed and/or the amount of further additives is chosen in such a way that the germination of the seed is not adversely affected, or that the resulting plant is not damaged. This must be borne in mind in particular in the case of active compounds which may have phytotoxic effects at certain application rates.
  • compositions according to the invention can be applied directly, that is to say without comprising further components and without having been diluted.
  • suitable formulations and methods for the treat- ment of seed are known to the person skilled in the art and are described, for example, in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 Al, WO 2002/080675 Al, WO 2002/028186 A2.
  • the active compound combinations which can be used according to the invention can be converted into customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating materials for seed, and also ULV formulations.
  • formulations are prepared in a known manner by mixing the active compounds or active compound combinations with customary additives, such as, for example, customary extenders and also solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water as well.
  • customary additives such as, for example, customary extenders and also solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water as well.
  • Suitable colorants that may be present in the seed dressing formulations which can be used according to the invention include all colorants customary for such purposes. Use may be made both of pigments, of sparing solubility in water, and of dyes, which are soluble in water. Examples that may be mentioned include the colorants known under the designations Rhodamine B, C.I. Pigment Red 112, and C.I. Solvent Red 1.
  • Suitable wetting agents that may be present in the seed dressing formulations which can be used according to the invention include all substances which promote wetting and are customary in the formulation of active agrochemical substances. With preference it is possible to use alkylnaphthalene- sulphonates, such as diisopropyl- or diisobutylnaphthalene-sulphonates.
  • Suitable dispersants and/or emulsifiers that may be present in the seed dressing formulations which can be used according to the invention include all nonionic, anionic, and cationic dispersants which are customary in the formulation of active agrochemical substances. With preference, it is possible to use nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers, and tristyrylphenol polyglycol ethers, and their phosphated or sulphated derivatives.
  • Particularly suitable anionic dispersants are lignosulphonates, polyacrylic salts, and arylsulphonate- formaldehyde condensates.
  • Defoamers that may be present in the seed dressing formulations to be used according to the invention include all foam-inhibiting compounds which are customary in the formulation of agrochemically active compounds. Preference is given to using silicone defoamers, magnesium stearate, silicone emulsions, long-chain alcohols, fatty acids and their salts and also organofluorine compounds and mixtures thereof.
  • Preservatives that may be present in the seed dressing formulations to be used according to the invention include all compounds which can be used for such purposes in agrochemical compositions.
  • agrochemical compositions By way of example, mention may be made of dichlorophen and benzyl alcohol hemiformal.
  • Secondary thickeners that may be present in the seed dressing formulations to be used according to the invention include all compounds which can be used for such purposes in agrochemical compositions.
  • Suitable adhesives that may be present in the seed dressing formulations to be used according to the invention include all customary binders which can be used in seed dressings.
  • Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose may be mentioned as being preferred.
  • the gibberellins are known (cf. R. Wegler "Chemie der Pflan- zenschutz- and Schadlingsbekampfungsmitter' [Chemistry of Crop Protection Agents and Pesticides], Vol. 2, Springer Verlag, 1970, pp. 401-412).
  • the seed dressing formulations which can be used according to the invention may be used directly or after dilution with water beforehand to treat seed of any of a very wide variety of types.
  • the seed dressing formulations which can be used according to the invention or their dilute preparations may also be used to dress seed of transgenic plants.
  • synergistic effects may also arise in interaction with the substances formed by expression.
  • Suitable mixing equipment for treating seed with the seed dressing formulations which can be used according to the invention or the preparations prepared from them by adding water includes all mixing equipment which can commonly be used for dressing.
  • the specific procedure adopted when dressing comprises introducing the seed into a mixer, adding the particular desired amount of seed dressing formulation, either as it is or following dilution with water beforehand, and carrying out mixing until the formulation is uniformly distributed on the seed.
  • a drying operation follows.
  • the active compounds or compositions according to the invention have strong microbicidal activity and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and material protection.
  • fungicides can be used for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • bactericides can be used for controlling Pseudomonadaceae, Rhizobiaceae, Enter- obacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • the fungicidal compositions according to the invention can be used for the curative or protective control of phytopathogenic fungi. Accordingly, the invention also relates to curative and protective methods for controlling phytopathogenic fungi using the active compound combinations or compositions according to the invention, which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow. Preference is given to application onto the plant or the plant parts, the fruits or the soil in which the plants grow.
  • compositions according to the invention for combating phytopathogenic fungi in crop protection comprise an active, but non-phytotoxic amount of the compounds according to the invention.
  • Active, but non-phytotoxic amount shall mean an amount of the composition according to the invention which is sufficient to control or to completely kill the plant disease caused by fungi, which amount at the same time does not exhibit noteworthy symptoms of phytotoxicity.
  • These application rates generally may be varied in a broader range, which rate depends on several factors, e.g. the phytopathogenic fungi, the plant or crop, the climatic conditions and the ingredients of the composition according to the invention.
  • plants and plant parts can be treated.
  • plants are meant all plants and plant populations such as desirable and undesirable wild plants, cultivars and plant varieties (whether or not protectable by plant variety or plant breeder's rights).
  • Cultivars and plant varieties can be plants obtained by conventional propagation and breeding methods which can be assisted or supplemented by one or more biotechnological methods such as by use of double haploids, protoplast fusion, random and directed mutagenesis, molecular or genetic markers or by bioengineering and genetic engineering methods.
  • plant parts all above ground and below ground parts and organs of plants such as shoot, leaf, blossom and root, whereby for example leaves, needles, stems, branches, blossoms, fruiting bodies, fruits and seed as well as roots, tubers, corms and rhizomes are listed.
  • Crops and vegetative and generative propagating material for example cuttings, corms, rhizomes, tubers, runners and seeds also belong to plant parts.
  • the active compounds of the invention in combination with good plant tolerance and favourable toxicity to warm-blooded animals and being tolerated well by the environment, are suitable for protecting plants and plant organs, for increasing the harvest yields, for improving the quality of the harvested material. They may be preferably employed as crop protection agents. They are active against normally sensitive and resistant species and against all or some stages of development.
  • plants that can be protected by the method according to the invention mention may be made of major field crops like corn, soybean, cotton, Brassica oilseeds such as Brassica napus (e.g. canola), Brassica rapa, B. juncea (e.g. mustard) and Brassica carinata, rice, wheat, sugarbeet, sugarcane, oats, rye, barley, millet, triticale, flax, vine and various fruits and vegetables of various botanical taxa such as Rosaceae sp.
  • Brassica oilseeds such as Brassica napus (e.g. canola), Brassica rapa, B. juncea (e.g. mustard) and Brassica carinata, rice, wheat, sugarbeet, sugarcane, oats, rye, barley, millet, triticale, flax, vine and various fruits and vegetables of various botanical taxa such as Rosaceae sp.
  • Brassica oilseeds such as Brassica napus (e.g. canola
  • Ribesioidae sp. Juglan- daceae sp.
  • Betulaceae sp. Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Ac- tinidaceae sp., Lauraceae sp., Musaceae sp. (for instance banana trees and plantings), Rubiaceae sp.
  • Theaceae sp. for instance coffee
  • Theaceae sp. Sterculiceae sp.
  • Rutaceae sp. for instance lemons, oranges and grapefruit
  • Solanaceae sp. for instance tomatoes, potatoes, peppers, eggplant
  • Liliaceae sp. Compo- sitiae sp.
  • lettuce, artichoke and chicory - including root chicory, endive or common chicory for instance Umbelliferae sp. (for instance carrot, parsley, celery and celeriac)
  • Cucurbitaceae sp. for instance cucumber - including pickling cucumber, squash, watermelon, gourds and melons
  • Cruciferae sp. for instance white cabbage, red cabbage, broccoli, cauliflower, brussel sprouts, pak choi, kohlrabi, radish, horseradish, cress, Chinese cabbage
  • Leguminosae sp. for instance peanuts, peas and beans beans - such as climbing beans and broad beans
  • Chenopodiace- ae sp. for instance mangold, spinach beet, spinach, beetroots
  • Malvaceae for instance okra
  • Aspara- gaceae for instance asparagus
  • horticultural and forest crops ornamental plants; as well as genetically modified homologues of these crops.
  • the plants that can be protected by the method according to the invention are selected among cotton, vine, cereals (such as wheat, rice, barley, triticale), maize (corn), soybean, oilseed rape, sunflower, turf, horticultural crops, shrubs, fruit-trees and fruit-plants (such as apple-tree, peer-tree, citrus, banana, coffea, strawberry plant, raspberry plant), vegetables, particularly cereals, corn, oilseed rape, shrubs, fruit-trees and fruit-plants, vegetables and vines.
  • cereals such as wheat, rice, barley, triticale
  • maize corn
  • soybean oilseed rape
  • sunflower turf
  • horticultural crops shrubs
  • fruit-trees and fruit-plants such as apple-tree, peer-tree, citrus, banana, coffea, strawberry plant, raspberry plant
  • vegetables particularly cereals, corn, oilseed rape, shrubs, fruit-trees and fruit-plants, vegetables and vines.
  • plants and plant parts can be treated.
  • plants are meant all plants and plant populations such as desirable and undesirable wild plants, cultivars and plant varieties (whether or not protectable by plant variety or plant breeder's rights).
  • Cultivars and plant varieties can be plants obtained by conventional propagation and breeding methods which can be assisted or supplemented by one or more biotechnological methods such as by use of double haploids, protoplast fusion, random and directed mutagenesis, molecular or genetic markers or by bioengineering and genetic engineering methods.
  • plant parts are meant all above ground and below ground parts and organs of plants such as shoot, leaf, blossom and root, whereby for example leaves, needles, stems, branches, blossoms, fruiting bodies, fruits and seed as well as roots, corms and rhizomes are listed.
  • Crops and vegetative and generative propagating material for example cuttings, corms, rhizomes, runners and seeds also belong to plant parts.
  • the method of treatment according to the invention can be used in the treatment of genetically modified organisms (GMOs), e.g. plants or seeds.
  • GMOs genetically modified organisms
  • Genetically modified plants are plants of which a heterologous gene has been stably integrated into genome.
  • the expression "heterologous gene” essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome gives the transformed plant new or im- proved agronomic or other properties by expressing a protein or polypeptide of interest or by downreg- ulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression technology, RNA interference - R Ai - technology or microR A - miR A - technology).
  • a heterologous gene that is located in the genome is also called a transgene.
  • a transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.
  • the treatment according to the invention may also result in superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the active compounds and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, bigger fruits, larger plant height, greener leaf color, earlier flowering, higher quality and/or a higher nutritional value of the harvested products, higher sugar concentration within the fruits, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected.
  • the active compound combinations according to the invention may also have a strengthening effect in plants. Accordingly, they are also suitable for mobilizing the defense system of the plant against attack by unwanted microorganisms. This may, if appropriate, be one of the reasons of the enhanced activity of the combinations according to the invention, for example against fungi.
  • Plant-strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, those substances or combinations of substances which are capable of stimulating the defense system of plants in such a way that, when subsequently inoculated with unwanted microorganisms, the treated plants display a substantial degree of resistance to these microorganisms.
  • the substances according to the invention can be employed for protecting plants against attack by the abovementioned pathogens within a certain period of time after the treatment.
  • the period of time within which protection is effected generally extends from 1 to 28 days, preferably 1 to 14 days, after the treatment of the plants with the active compounds.
  • Plants and plant cultivars which are preferably to be treated according to the invention include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means).
  • Plants and plant cultivars which are also preferably to be treated according to the invention are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.
  • nematode resistant plants are described in e.g. US Patent Application Nos 1 1/765,491, 11/765,494, 10/926,819, 10/782,020, 12/032,479, 10/783,417, 10/782,096, 1 1/657,964, 12/192,904, 11/396,808, 12/166,253, 12/166,239, 12/166,124, 12/166,209, 1 1/762,886, 12/364,335, 11/763,947, 12/252,453, 12/209,354, 12/491,396, 12/497,221, 12/644,632, 12/646,004, 12/701,058, 12/718,059, 12/721,595, 12/638,591 and in WO 11/002992, WOl 1/014749, WOl 1/103247, WOl 1/103248.
  • Plants and plant cultivars which may also be treated according to the invention are those plants which are resistant to one or more abiotic stresses.
  • Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.
  • Plants and plant cultivars which may also be treated according to the invention are those plants characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation.
  • Yield can furthermore be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance.
  • Further yield traits include seed composition, such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction in anti-nutritional compounds, improved processability and better storage stability.
  • Plants that may be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stresses). Such plants are typically made by crossing an inbred male-sterile parent line (the female parent) with another inbred male-fertile parent line (the male parent). Hybrid seed is typically harvested from the male sterile plants and sold to growers. Male sterile plants can sometimes (e.g. in corn) be produced by detasseling, i.e. the mechanical removal of the male reproductive organs (or males flowers) but, more typically, male sterility is the result of genetic determinants in the plant genome.
  • Male sterile plants can also be obtained by plant biotechnology methods such as genetic engineering.
  • a particularly useful means of obtaining male-sterile plants is described in WO 89/10396 in which, for example, a ribonuclease such as barnase is selectively expressed in the tapetum cells in the stamens. Fertility can then be restored by expression in the tapetum cells of a ribonuclease inhibitor such as barstar (e.g. WO 91/02069).
  • Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance.
  • Herbicide-resistant plants are for example glyphosate-tolerant plants, i.e. plants made tolerant to the herbicide glyphosate or salts thereof. Plants can be made tolerant to glyphosate through different means.
  • glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5 -enolpyruvylshikimate-3 -phosphate synthase (EPSPS).
  • EPSPS 5 -enolpyruvylshikimate-3 -phosphate synthase
  • Examples of such EP- SPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp.
  • Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate oxido-reductase enzyme as described in U.S. Patent Nos. 5,776,760 and 5,463,175. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate acetyl transferase enzyme as described in for example WO 02/36782, WO 03/092360, WO 05/012515 and WO 07/024782. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above-mentioned genes, as described in for example WO 01/024615 or WO 03/013226.
  • Plants expressing EPSPS genes that confer glyphosate tolerance are described in e.g. US Patent Application Nos 11/517,991, 10/739,610, 12/139,408, 12/352,532, 1 1/312,866, 11/315,678, 12/421,292, 1 1/400,598, 11/651,752, 11/681,285, 11/605,824, 12/468,205, 11/760,570, 11/762,526, 11/769,327, 11/769,255, 1 1/943801 or 12/362,774. Plants comprising other genes that confer glyphosate tolerance, such as decarboxylase genes, are described in e.g. US patent applications 11/588,811, 11/185,342, 12/364,724, 11/185,560 or 12/423,926.
  • herbicide resistant plants are for example plants that are made tolerant to herbicides inhibiting the enzyme glutamine synthase, such as bialaphos, phosphinothricin or glufosinate.
  • Such plants can be obtained by expressing an enzyme detoxifying the herbicide or a mutant glutamine synthase enzyme that is resistant to inhibition, e.g. described in US Patent Application No 1 1/760,602.
  • One such efficient detoxifying enzyme is an enzyme encoding a phosphinothricin acetyltransferase (such as the bar or pat protein from Streptomyces species).
  • Plants expressing an exogenous phosphinothricin acetyltransferase are for example described in U.S. Patent Nos. 5,561,236; 5,648,477; 5,646,024; 5,273,894; 5,637,489; 5,276,268; 5,739,082; 5,908,810 and 7,1 12,665.
  • HPPD hydroxyphenylpyruvatedioxygenase
  • Plants tolerant to HPPD-inhibitors can be transformed with a gene encoding a naturally-occurring resistant HPPD enzyme, or a gene encoding a mutated or chimeric HPPD enzyme as described in WO 96/38567, WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387, or US 6,768,044, WOl 1/076877, WOl 1/076882, WOl 1/076885, WOl 1/076889, WOl 1/076892.
  • Tolerance to HPPD-inhibitors can also be obtained by transforming plants with genes encoding certain enzymes enabling the formation of homogentisate despite the inhibition of the native HPPD enzyme by the HPPD-inhibitor. Such plants and genes are described in WO 99/34008 and WO 02/36787. Tolerance of plants to HPPD inhibitors can also be improved by transforming plants with a gene encoding an enzyme having pre- phenate deshydrogenase (PDH) activity in addition to a gene encoding an HPPD-tolerant enzyme, as described in WO 2004/024928.
  • PDH pre- phenate deshydrogenase
  • plants can be made more tolerant to HPPD-inhibitor herbicides by adding into their genome a gene encoding an enzyme capable of metabolizing or degrading HPPD inhibitors, such as the CYP450 enzymes shown in WO 2007/103567 and WO 2008/150473.
  • an enzyme capable of metabolizing or degrading HPPD inhibitors such as the CYP450 enzymes shown in WO 2007/103567 and WO 2008/150473.
  • Still further herbicide resistant plants are plants that are made tolerant to acetolactate synthase (ALS) inhibitors.
  • ALS-inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrim- idines, pryimidinyoxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinone herbicides.
  • Different mutations in the ALS enzyme also known as acetohydroxyacid synthase, AHAS
  • AHAS acetohydroxyacid synthase
  • imidazolinone-tolerant plants are also described in for example WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351, and WO 2006/060634. Further sulfonylurea- and imidazolinone-tolerant plants are also described in for example WO 07/024782, WO 11/076345, WO2012058223 and US Patent Application No 61/288958.
  • plants tolerant to imidazolinone and/or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or mutation breeding as described for example for soybeans in U.S. Patent 5,084,082, for rice in WO 97/41218, for sugar beet in U.S. Patent 5,773,702 and WO 99/057965, for lettuce in U.S. Patent 5,198,599, or for sunflower in WO 01/065922.
  • Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance.
  • An "insect-resistant transgenic plant”, as used herein, includes any plant containing at least one transgene comprising a coding sequence encoding:
  • an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof such as the insecticidal crystal proteins listed by Crickmore et al. (1998, Microbiology and Molecular Biology Reviews, 62: 807-813), updated by Crickmore et al.
  • insecticidal portions thereof e.g., proteins of the Cry protein classes CrylAb, CrylAc, CrylB, CrylC, CrylD, CrylF, Cry2Ab, Cry3Aa, or Cry3Bb or insecticidal portions thereof (e.g. EP 1999141 and WO 2007/107302), or such proteins encoded by synthetic genes as e.g. described in and US Patent Application No 12/249,016 ; or
  • a crystal protein from Bacillus thuringiensis or a portion thereof which is insecticidal in the presence of a second other crystal protein from Bacillus thuringiensis or a portion thereof, such as the binary toxin made up of the Cry34 and Cry35 crystal proteins (Moellenbeck et al. 2001, Nat. Biotechnol. 19: 668-72; Schnepf et al. 2006, Applied Environm. Microbiol. 71, 1765-1774) or the binary toxin made up of the CrylA or CrylF proteins and the Cry2Aa or Cry2Ab or Cry2Ae proteins (US Patent Appl. No.
  • a hybrid insecticidal protein comprising parts of different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g., the CrylA.105 protein produced by corn event MON89034 (WO 2007/027777); or
  • VIP vegetative insecticidal proteins listed at: http://www.lifesci.sussex.ac.u home/Keil_Crickmore/Bt/vip.html, e.g., proteins from the VIP3Aa protein class; or
  • a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin made up of the VIP1A and VIP2A proteins (WO 94/21795); or
  • a hybrid insecticidal protein comprising parts from different secreted proteins from Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins in 1) above or a hybrid of the proteins in 2) above; or
  • 8) a protein of any one of 5) to 7) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation (while still encoding an insecticidal protein), such as the VIP3Aa protein in cotton event COT 102; or
  • a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a crystal protein from Bacillus thuringiensis, such as the binary toxin made up of VIP3 and CrylA or CrylF (US Patent Appl. No. 61/126083 and 61/195019), or the binary toxin made up of the VIP3 protein and the Cry2Aa or Cry2Ab or Cry2Ae proteins (US Patent Appl. No. 12/214,022 and EP 08010791.5).
  • a crystal protein from Bacillus thuringiensis such as the binary toxin made up of VIP3 and CrylA or CrylF (US Patent Appl. No. 61/126083 and 61/195019), or the binary toxin made up of the VIP3 protein and the Cry2Aa or Cry2Ab or Cry2Ae proteins (US Patent Appl. No. 12/214,022 and EP 08010791.5).
  • an insect-resistant transgenic plant also includes any plant comprising a combination of genes encoding the proteins of any one of the above classes 1 to 10.
  • an insect-resistant plant contains more than one transgene encoding a protein of any one of the above classes 1 to 10, to expand the range of target insect species affected when using different proteins directed at different target insect species, or to delay insect resistance development to the plants by using different proteins insecticidal to the same target insect species but having a different mode of action, such as binding to different receptor binding sites in the insect.
  • An "insect-resistant transgenic plant”, as used herein, further includes any plant containing at least one transgene comprising a sequence producing upon expression a double-stranded R A which upon ingestion by a plant insect pest inhibits the growth of this insect pest, as described e.g. in WO 2007/080126, WO 2006/129204, WO 2007/074405, WO 2007/080127 and WO 2007/035650.
  • Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering which may also be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance. Particularly useful stress tolerance plants include:
  • plants which contain a stress tolerance enhancing transgene coding for a plant-functional enzyme of the nicotineamide adenine dinucleotide salvage synthesis pathway including nico- tinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyl transferase, nicotinamide adenine dinucleotide synthetase or nicotine amide phosphorybosyl- transferase as described e.g. in EP 04077624.7, WO 2006/133827, PCT/EP07/002433, EP 1999263, or WO 2007/107326.
  • Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering
  • Plants or plant cultivars show altered quantity, quality and/or storage- stability of the harvested product and/or altered properties of specific ingredients of the harvested product such as :
  • transgenic plants which synthesize a modified starch, which in its physical-chemical characteristics, in particular the amylose content or the amylose/amylopectin ratio, the degree of branching, the average chain length, the side chain distribution, the viscosity behaviour, the gelling strength, the starch grain size and/or the starch grain morphology, is changed in comparison with the synthesised starch in wild type plant cells or plants, so that this is better suited for special applications.
  • a modified starch which in its physical-chemical characteristics, in particular the amylose content or the amylose/amylopectin ratio, the degree of branching, the average chain length, the side chain distribution, the viscosity behaviour, the gelling strength, the starch grain size and/or the starch grain morphology, is changed in comparison with the synthesised starch in wild type plant cells or plants, so that this is better suited for special applications.
  • transgenic plants synthesizing a modified starch are disclosed, for example, in EP 0571427, WO 95/04826, EP 0719338, WO 96/15248, WO 96/19581, WO 96/27674, WO 97/11 188, WO 97/26362, WO 97/32985, WO 97/42328, WO 97/44472, WO 97/45545, WO 98/27212, WO 98/40503, W099/58688, WO 99/58690, WO 99/58654, WO 00/08184, WO 00/08185, WO 00/08175, WO 00/28052, WO 00/77229, WO 01/12782, WO 01/12826, WO 02/101059, WO 03/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO 2005/095617, WO
  • transgenic plants which synthesize non starch carbohydrate polymers or which synthesize non starch carbohydrate polymers with altered properties in comparison to wild type plants without genetic modification.
  • Examples are plants producing polyfructose, especially of the inulin and levan-type, as disclosed in EP 0663956, WO 96/01904, WO 96/21023, WO 98/39460, and WO 99/24593, plants producing alpha- 1,4-glucans as disclosed in WO 95/31553, US 2002031826, US 6,284,479, US 5,712,107, WO 97/47806, WO 97/47807, WO 97/47808 and WO 00/14249, plants producing alpha-1,6 branched alpha- 1 ,4-glucans, as disclosed in WO 00/73422, plants producing alternan, as disclosed in e.g.
  • transgenic plants or hybrid plants such as onions with characteristics such as 'high soluble solids content', 'low pungency' (LP) and/or 'long storage' (LS), as described in US Patent Appl. No. 12/020,360 and 61/054,026.
  • Plants or plant cultivars which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics.
  • Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics and include: a) Plants, such as cotton plants, containing an altered form of cellulose synthase genes as described in WO 98/00549
  • Plants such as cotton plants, having fibers with altered reactivity, e.g. through the expression of N-acetylglucosaminetransferase gene including nodC and chitin synthase genes as described in WO 2006/136351 WOl 1/089021, WO2012074868
  • Plants or plant cultivars which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil profile characteristics.
  • Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered oil profile characteristics and include: a) Plants, such as oilseed rape plants, producing oil having a high oleic acid content as described e.g.
  • Plants or plant cultivars which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered seed shattering characteristics.
  • Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered seed shattering characteristics and include plants such as oilseed rape plants with delayed or reduced seed shattering as described in US Patent Appl. No. 61/135,230, WO09/068313, WO10/006732 and WO2012090499.
  • Plants or plant cultivars which may also be treated according to the invention are plants, such as Tobacco plants, with altered post-translational protein modification patterns, for example as described in WO 10/121818 and WO 10/145846
  • Particularly useful transgenic plants which may be treated according to the invention are plants containing transformation events, or combination of transformation events, that are the subject of petitions for non-regulated status, in the United States of America, to the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) whether such petitions are granted or are still pending.
  • APHIS Animal and Plant Health Inspection Service
  • USA United States Department of Agriculture
  • Petition the identification number of the petition.
  • Technical descriptions of the transformation events can be found in the individual petition documents which are obtainable from APHIS, for example on the APHIS website, by reference to this petition number. These descriptions are herein incorporated by reference.
  • Extension of Petition reference to a previous petition for which an extension is requested.
  • Transgenic phenotype the trait conferred to the plants by the transformation event. Transformation event or line : the name of the event or events (sometimes also designated as lines or lines) for which nonregulated status is requested.
  • APHIS documents various documents published by APHIS in relation to the Petition and which can be requested with APHIS.
  • Particularly useful transgenic plants which may be treated according to the invention are plants containing transformation events, or a combination of transformation events, and that are listed for example in the databases for various national or regional regulatory agencies including Event 1 143-14A (cotton, insect control, not deposited, described in WO2006/128569); Event 1 143-51B (cotton, insect control, not deposited, described in WO2006/128570); Event 1445 (cotton, herbicide tolerance, not deposited, described in US2002120964 or WO2002/034946); Event 17053 (rice, herbicide tolerance, deposited as PTA-9843, described in WO2010/117737); Event 17314 (rice, herbicide tolerance, deposited as PTA-9844, described in WO2010/117735); Event 281-24-236 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in WO2005/103266 or US2005216969); Event 3006-210-23 (cotton, insect control - herbicide tolerance, deposited as PTA-6233,
  • Event CE43-67B (cotton, insect control, deposited as DSM ACC2724, described in US2009217423 or WO2006/128573); Event CE44-69D (cotton, insect control, not deposited, described in US20100024077); Event CE44-69D (cotton, insect control, not deposited, described in WO2006/128571); Event CE46-02A (cotton, insect control, not deposited, described in WO2006/128572); Event COT102 (cotton, insect control, not deposited, described in US2006130175 or WO2004039986); Event COT202 (cotton, insect control, not deposited, described in US2007067868 or WO2005054479); Event COT203 (cotton, insect control, not deposited, described in WO2005/054480); Event DAS40278 (corn, herbicide tolerance, deposited as ATCC PTA- 10244, described in WO2011/022469); Event DAS-59122-7
  • the substances of the invention may be used for the protection of technical materials against infestation and destruction by undesirable fungi and/or microorganisms.
  • Technical materials are understood to be in the present context non-living materials that have been prepared for use in engineering.
  • technical materials that are to be protected against micro-biological change or destruction by the active materials of the invention can be adhesives, glues, paper and cardboard, textiles, carpets, leather, wood, paint and plastic articles, cooling lubricants and other materials that can be infested or destroyed by micro-organisms.
  • materials to be protected are also parts of production plants and buildings, for example cooling circuits, cooling and heating systems, air conditioning and ventilation systems, which can be adversely affected by the propagation of fungi and/or microorganisms.
  • adhesives preferably mentioned as technical materials are adhesives, glues, paper and cardboard, leather, wood, paints, cooling lubricants and heat exchanger liquids, particularly preferred is wood.
  • the combinations according to the invention can prevent disadvantageous effects like decaying, dis- and decoloring, or molding.
  • the active compound combinations and compositions according to the invention can likewise be employed for protecting against colonization of objects, in particular ship hulls, sieves, nets, buildings, quays and signalling installations, which are in contact with sea water or brackish water.
  • the method of treatment according to the invention can also be used in the field of protecting storage goods against attack of fungi and microorganisms.
  • the term "storage goods” is understood to denote natural substances of vegetable or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired.
  • Storage goods of vegetable origin such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted.
  • storage goods are timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood.
  • Storage goods of animal origin are hides, leather, furs, hairs and the like. The combinations according the present invention can prevent disadvantageous effects such as decay, discoloration or mold.
  • storage goods is understood to denote natural substances of vegetable origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.
  • Blumeria species such as, for example, Blumeria graminis
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Uncinula species such as, for example, Uncinula necator
  • Gymnosporangium species such as, for example, Gymnosporangium sabinae
  • Hemileia species such as, for example, Hemileia vastatrix
  • Phakopsora species such as, for example, Phakopsora pachyrhizi and Phakopsora meibomiae
  • Puc- cinia species such as, for example, Puccinia recondita or Puccinia triticina
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae
  • Phytophthora species such as, for example Phytophthora infestans
  • Plasmopara species such as, for example, Plasmopara viticola
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis
  • Pythium species such as, for example, Pythium ultimum
  • Pythium species such as, for example, Pythium ultimum
  • Ear and panicle diseases caused, for example, by Alternaria species, such as, for example, Alternaria spp.; Aspergillus species, such as, for example, Aspergillus flavus; Cladosporium species, such as, for example, Cladosporium cladosporioides; Claviceps species, such as, for example, Claviceps purpurea; Fusarium species, such as, for example, Fusarium culmorum; Gibberella species, such as, for example, Gibberella zeae; Monographella species, such as, for example, Monographella nivalis; Septoria species, such as for example, Septoria nodorum;
  • Seed- and soil-borne decay, mould, wilt, rot and damping-off diseases caused, for example, by Alternaria diseases caused for example by Alternaria brassicicola; Aphanomyces diseases caused for example by Aphanomyces euteiches; Ascochyta diseases caused for example by Ascochyta lentis; Aspergillus diseases caused for example by Aspergillus flavus; Cladosporium diseases caused for example by Cladosporium herbarum; Cochliobolus diseases caused for example by Cochliobolus sativus; (Conidia- form: Drechslera, Bipolaris Syn: Helminthosporium); Colletotrichum diseases caused for example by Colletotrichum coccodes; Fusarium diseases caused for example by Fusarium culmorum; Gibberella diseases caused for example by Gibberella zeae; Macrophomina diseases caused for example by Mac- rophomina phaseolina; Microdochium diseases caused for example by Micro
  • Sphacelotheca species such as, for example, Sphacelotheca reiliana
  • Tilletia species such as, for example, Tilletia caries
  • T. controversa Urocystis species, such as, for example, Urocystis occulta
  • Ustilago species such as, for example, Usti- lago nuda; U. nuda tritici;
  • Seed- and soil-borne rot and wilt diseases, and also diseases of seedlings caused, for example, by Fusarium species, such as, for example, Fusarium culmorum; Phytophthora species, such as, for example, Phytophthora cactorum; Pythium species, such as, for example, Pythium ultimum; Rhizoctonia species, such as, for example, Rhizoctonia solani; Sclerotium species, such as, for example, Scleroti- um rolfsii;
  • Nectria species such as, for example, Nectria galligena
  • Degenerative diseases of woody plants caused, for example, by Esca species, such as, for example, Phaemoniella clamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea;
  • Botrytis species such as, for example, Botrytis cinerea
  • Rhizoctonia species such as, for example, Rhizoctonia solani
  • Helminthosporium species such as, for example, Helminthosporium solani
  • bacteriopathogens such as, for example, Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae; Pseudomonas species, such as, for example, Pseudo- monas syringae pv. lachrymans; Erwinia species, such as, for example, Erwinia amylovora.
  • Fungal diseases on roots and the stem base caused, for example, by black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmopspora vasinfec- ta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var.
  • phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia Southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).
  • Microorganisms capable of degrading or changing the industrial materials are, for example, bacteria, fungi, yeasts, algae and slime organisms.
  • the active compounds according to the invention preferably act against fungi, in particular moulds, wood-discolouring and wood- destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • Microorganisms of the following genera may be mentioned as examples: Alternaria, such as Alternaria tenuis, Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum, Coniophora, such as Coniophora puetana, Lentinus, such as Lentinus tigrinus, Penicillium, such as Penicillium glaucum, Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa, and Staphylococcus, such as Staphylococcus aureus.
  • Alternaria such as Alternaria tenuis
  • the compounds of the formula (I) according to the invention also have very good antimy- cotic activity. They have a very broad antimycotic activity spectrum in particular against dermatophytes and yeasts, moulds and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Micro- sporon species such as Microsporon canis and audouinii.
  • Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum for example against Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum for example against Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum for example against Candida species such as Candida albicans, Candida glab
  • the application rates can be varied within a broad range.
  • the dose of active compound/application rate usually applied in the method of treatment according to the invention is generally and advantageously
  • the combination according to the invention can be used in order to protect plants within a certain time range after the treatment against pests and/or phytopathogenic fungi and/or microorganisms.
  • the time range, in which protection is effected spans in general 1 to 28 days, preferably 1 to 14 days, more preferably 1 to 10 days, even more preferably 1 to 7 days after the treatment of the plants with the combinations or up to 200 days after the treatment of plant propagation material.
  • compositions according to the invention may also be used to reduce the contents of mycotoxins in plants and the harvested plant material and therefore in foods and animal feed stuff made therefrom.
  • mycotoxins can be specified: Deoxynivalenole (DON), Nivalenole, 15-Ac-DON, 3-Ac-DON, T2- und HT2- Toxins, Fumonisines, Zearalenone Moniliformine, Fusarine, Diaceotoxyscirpenole (DAS), Beauvericine, En- niatine, Fusaroproliferine, Fusarenole, Ochratoxines, Patuline, Ergotalkaloides und Aflatoxines, which are caused for example by the following fungal diseases: Fusarium spec, like Fusarium acuminatum, F.
  • the compounds of the formula (I) or salts thereof in combination with compounds (B), (C) or (D) are also suitable for the selective control of harmful organisms in a number of plant crops, for example in crops of economic importance, such as cereals (wheat, barley, triticale, rye, rice, corn, millet), sugar beet, sugar cane, oilseed rape, cotton, sunflower, peas, beans and soybeans.
  • monocotyledonous crops such as cereals (wheat, barley, rye, triticale, sorghum), including corn and rice, and monocotyledonous vegetable crops, but also in dicotyledonous crops, such as, for example, soybean, oilseed rape, cotton, grape vines, vegetable plants, fruit plants and ornamental plants.
  • the combinations are preferred for the selective control of harmful plants in useful plants (crops).
  • the combinations according to the invention are also suitable for controlling harmful plants in beds and plots of useful plants and ornamental plants, such as, for example, lawn plots with useful or ornamental lawn, especially lolium, meadow grass or Bermuda grass.
  • the compounds of the formula (I) or salts thereof in combination with compounds (B), (C) or (D) are also suitable for the selective control of harmful organisms in a number of plants selected among cotton, vine, cereals (such as wheat, rice, barley, triticale), maize (corn), soybean, oilseed rape, sunflower, turf, horticultural crops, shrubs, fruit-trees and fruit-plants (such as apple-tree, peer-tree, citrus, banana, coffea, strawberry plant, raspberry plant), vegetables, particularly cereals, corn, oilseed rape, shrubs, fruit-trees and fruit-plants, vegetables and vines.
  • cereals such as wheat, rice, barley, triticale
  • maize corn
  • soybean oilseed rape
  • sunflower turf
  • horticultural crops shrubs
  • fruit-trees and fruit-plants such as apple-tree, peer-tree, citrus, banana, coffea, strawberry plant, raspberry plant
  • vegetables particularly cereals, corn, oilseed rape
  • mutant crops which are completely or partially tolerant to certain pesticides or completely or partially tolerant transgenic crops for example corn crops which are resistant to glufosinate or glyphosate, or soybean crops which are resistant to herbicidal imidazolinones.
  • corn crops which are resistant to glufosinate or glyphosate or soybean crops which are resistant to herbicidal imidazolinones.
  • the particular advantage of the combinations in this novel way is their efficient action in crops which normally are insufficiently tolerant to the pesticides being applied.
  • the invention also provides a method for the selective control of harmful plants in crops of useful plants which comprises applying an effective useful-plant-protecting amount of one or more compounds (I) in combination with compounds (B), (C) or (D) or salts thereof before, after or simultaneously with an amount, effective against harmful plants, of one or more herbicides to the plants, parts of plants, plant seeds or seed.
  • N-cyclopropyl amides of formula (I) wherein T represents an oxygen atom can be prepared by condensation of a substituted N-cyclopropyl benzylamine with 3-(difluoromethyl)-5-fluoro-l-methyl-lH- pyrazole-4-carbonyl chloride according to WO-2007/087906 (process PI) and WO-2010/130767 (process PI - step 10).
  • N-cyclopropyl benzylamines are known or can be prepared by known processes such as the reductive amination of a substituted aldehyde with cyclopropanamine (J. Med. Chem., 2012, 55 (1), 169-196) or by nucleophilic substitution of a substituted benzyl alkyl (or aryl)sulfonate or a substituted benzyl halide with cyclopropanamine (Bioorg. Med. Chem., 2006, 14, 8506-8518 and WO- 2009/140769).
  • 3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carbonyl chloride can be prepared according to WO-2010/130767 (process PI - steps 9 or 11)
  • N-cyclopropyl thioamides of formula (I) wherein T represents a sulfur atom can be prepared by thio- nation of a N-cyclopropyl amide of formula (I) wherein T represents a oxygen atom, according to WO-2009/016220 (process PI) and WO-2010/130767 (process P3).
  • process PI WO-2009/016220
  • process P3 WO-2010/130767
  • Step A preparation of N-(2-isopropylbenzyl)cyclopropanamine
  • reaction mixture is then cooled to 0 °C and 45.8 g (729 mmol) of sodium cyanoborohydride are added by portion in 10 min and the reaction mixture is stirred again for 3 hours at reflux.
  • the cooled reaction mixture is filtered over a cake of diatomaceous earth. The cake is washed abundantly by methanol and the methanolic extracts are concentrated under vacuum. Water is then added to the residue and the pH is adjusted to 12 with 400 mL of a 1 N aqueous solution of sodium hydroxide.
  • the watery layer is extracted with ethyl acetate, washed by water (2 x 300 mL) and dried over magnesium sulfate to yield 81.6 g (88%) of N-(2-isopropylbenzyl)cyclopropanamine as a yellow oil used as such in the next step.
  • Step B preparation of N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-l-methyl- 1 H-pyrazole-4-carboxamide
  • logP values were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a reversed-phase column (C 18), using the method described below :
  • Calibration was carried out using unbranched alkan-2-ones (comprising 3 to 16 carbon atoms) with known logP values (determination of the logP values by the retention times using linear interpolation between two successive alkanones). lambda-max- values were determined using UV-spectra from 200 nm to 400 nm and the peak values of the chromatographic signals.
  • the good fungicidal activity of the active compound combinations according to the invention is evident from the example below. While the individual active compounds exhibit weaknesses with regard to the fungicidal activity, the combinations have an activity which exceeds a simple addition of activities. A synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
  • the expected activity for a given combination of two active compounds can be calculated as follows (cf. Colby, S.R., "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds
  • X is the efficacy when active compound A is applied at an application rate of m ppm (or g/ha),
  • Y is the efficacy when active compound B is applied at an application rate of n ppm (or g/ha),
  • E is the efficacy when the active compounds A and B are applied at application rates of m and n ppm (or g/ha), respectively, and
  • the degree of efficacy, expressed in % is denoted. 0 % means an efficacy which corresponds to that of the control while an efficacy of 100 % means that no disease is observed. If the actual fungicidal activity exceeds the calculated value, then the activity of the combination is superadditive, i.e. a synergistic effect exists. In this case, the efficacy which was actually observed must be greater than the value for the expected efficacy (E) calculated from the abovementioned formula.
  • E expected efficacy
  • Example A Blumeria test (barley) / preventive
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are dusted with spores of Blumeria graminis f.sp. hordei.
  • the plants are placed in the greenhouse at a temperature of approximately 18 °C and a relative atmospheric humidity of approximately 80% to promote the development of mildew pustules.
  • the test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.
  • Example B Leptosphaeria nodorum test (wheat) / preventive
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are sprayed with a spore suspension of Leptosphaeria nodorum.
  • the plants remain for 48 hours in an incubation cabinet at approximately 20 °C and a relative atmospheric humidity of approximately 100%.
  • the plants are placed in the greenhouse at a temperature of approximately 22 °C and a relative atmospheric humidity of approximately 80%.
  • the test is evaluated 8 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.
  • the table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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PCT/EP2013/071694 2012-10-19 2013-10-17 Active compound combinations comprising carboxamide derivatives Ceased WO2014060502A1 (en)

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EA201590771A EA026839B1 (ru) 2012-10-19 2013-10-17 Комбинации активных соединений, содержащие карбоксамидные соединения
UAA201504671A UA114822C2 (uk) 2012-10-19 2013-10-17 Комбінації активних сполук, що містять карбоксамідні похідні
AU2013333916A AU2013333916B2 (en) 2012-10-19 2013-10-17 Active compound combinations comprising carboxamide derivatives
CA2888600A CA2888600C (en) 2012-10-19 2013-10-17 Active compound combinations comprising carboxamide derivatives
EP13777076.4A EP2908639A1 (en) 2012-10-19 2013-10-17 Active compound combinations comprising carboxamide derivatives
US14/432,815 US9801374B2 (en) 2012-10-19 2013-10-17 Active compound combinations comprising carboxamide derivatives
CN201380054677.7A CN105357968A (zh) 2012-10-19 2013-10-17 包含羧酰胺衍生物的活性化合物复配物
BR122020002297-3A BR122020002297B1 (pt) 2012-10-19 2013-10-17 composição de compostos ativos, método para controlar fungos fitopatogênicos e uso das referidas composições
JP2015537246A JP6153619B2 (ja) 2012-10-19 2013-10-17 カルボキサミド誘導体を含む活性化合物の組み合わせ
BR112015008797-3A BR112015008797B1 (pt) 2012-10-19 2013-10-17 composição de compostos ativos, método para controlar fungos fitopatogênicos e uso das composições
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Cited By (10)

* Cited by examiner, † Cited by third party
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US9439426B2 (en) 2012-10-19 2016-09-13 Bayer Cropscience Ag Active compound combinations comprising carboxamide derivatives and a biological control agent
WO2016174042A1 (en) 2015-04-27 2016-11-03 BASF Agro B.V. Pesticidal compositions
US9668480B2 (en) 2012-10-19 2017-06-06 Bayer Cropscience Ag Method for treating plants against fungi resistant to fungicides using carboxamide or thiocarboxamide derivatives
WO2017207368A1 (en) 2016-06-02 2017-12-07 BASF Agro B.V. Fungicidal compositions
WO2018069109A1 (en) 2016-10-10 2018-04-19 Basf Se Pesticidal mixtures
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