DK2908641T3 - Fremgangsmåde til behandling af planter mod svampe, der er resistente over for fungicider, ved anvendelse af carboxamid- eller thiocarboxamidderivater - Google Patents

Description

Description [0001] The invention relates to a method comprising using N-cyclopropyl-N-[substituted-benzyl]-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide or thiocarboxamide derivatives (I) and/or salts thereof for improving growth in crops, comprising preventively and/or curatively controlling strains of fungi resistant to SDHI fungicides.

[0002] Severals fungicides are known as SDH (Succinate Dehydrogenase)

Inhibitors, which describes their mode of action. The target enzyme of SDH Inhibitors is succinate dehydrogenase (so-called complex II in the mitochondrial respiration chain), which is a functional part of the tricarboxylic cycle and linked to the mitochondrial electron transport chain (Keon et al., 1991, Current Genetics 19, 475-481). SDHI (Succinate Dehydrogenase Inhibitors) fungicides were discovered more than 40 years ago, and are very efficient fungicides for controlling a broad variety of major diseases in various crops, including cereals, soybean, corn, oilseed rape and speciality crops.

[0003] But, because of their single-site specificity, these SDHI fungicides can be prone to resistance development. Even more dramatic, resistance development leads often to cross-resistance, wherein resistance to a particular SDHI fungicide results in resistance to other SDHI fungicides, to which the fungi may not have been exposed.

[0004] Strains of fungi resistant to SDH inhibitors wherein the resistance is due to mutation(s) in the fungi succinate dehydrogenase gene are already known for several fungal species and the target site mutations have been already detected both in lab generated mutants and filed studies. Considering the apparition of strains resistant to fungicides as an urge problem, and particularly strains resistant to SDHI fungicides, FRAC (Fungicide Resistance Action Committee)-SDHI working group has been created for common resistance management recommendations.

[0005] The inventors of the present invention surprisingly found that N-cyclopropyl-N-[substituted-benzyl]-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide or thiocarboxamide derivatives are able to control strains of fungi resistant to other carboxamides fungicides.

[0006] N-cyclopropyl-N-[substituted-benzyl]-3-(difluoromethyl)-5-fluoro-1 -methyl-1 H-pyrazole-4-carboxamide or thiocarboxamide derivatives, their preparation from commercially available materials and their use as fungicides are disclosed in W02007/087906, W02009/016220, 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 PCTEP2012/001676 and PCT/EP2012/001674).

[0007] WO2012/110464 discloses the use of a succinate dehydrogenase inhibitor (SDHI) fungicide on conventionally bred ASR-tolerant, stem canker resistant and/or frog-eye leaf spot resistant soybean variety for controlling Asian soybean rust (ASR).

[0008] It is an object of the present invention to provide a method of plant growth in order to better control resistant strain of fungi, and obtain better plants, higher crop yield, better crop quality and better conditions of agricultural practices.

[0009] We have found that this object is achieved by a method for treating plants curatively and/or preventively against at least one strain of fungi which is resistant to at least one SDH I (succinate dehydrogenase inhibitor) fungicide, comprising applying to said plants, to the seeds from which they grow or to the locus in which they grow, a non-phytotoxic, effective plant growth promoting amount of a compound having the formula I

wherein 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), 2-ethyl, 2-trimethylsilyl and 2-ethyl-4,5-dimethyl, or an agrochemically acceptable salt thereof.

[0010] Preference is given to compound of the formula (I) selected from the group consisting of: N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1 -methyl-1 H-pyrazole-4-carboxamide (compound A1), N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound A2), N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound A3), N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound A4), N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound A5), N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (compound A6), N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide (compound A7), N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (compound A8), N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (compound A9), N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide (compound A10), N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound A11), N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide (compound A12), N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (compound A13), N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (compound A14), N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound A15), N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1 H-pyrazole-4-carboxamide (compound A16), N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1 -methyl-1 H-pyrazole-4-carboxamide (compound A17), N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1 -methyl-1 H-pyrazole-4-carboxamide (compound A18). N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (compound A19), N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1 H-pyrazole-4-carbothio-amide (compound A20), N-cyclopropyl-3-(difluoromethyl)-N-(2-ethylbenzyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound A21), and N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[2-(trimethylsilyl)benzyl]-1H-pyrazole-4-carboxamide (compound A22).

[0011] In the context of the invention a "resistant strain of fungi" means a mutated strain of fungi which is resistant to a fungicide when the wild-type of this strain is sensitive to said fungicide, when the fungicide is used at the usual rate of utilisation. The resistance can be due to a mutation in the gene encoding the target of the fungicide.

[0012] In the invention, compound of formula (I) or salt thereof are used for treating plants curatively and/or preventively against at least one resistant strain of fungi which is resistant to at least one SDHI (succinate dehydrogenase inhibitor) fungicide. Said "resistant strain of fungi" is a mutated strain of fungi which is resistant to at least one SDHI fungicide, when the wild-type of this strain is sensitive to said fungicide. The resistance may be a cross-resistance, which results in resistance to several SDHI fungicides, which may be from similar chemical classes, and/or may have the same target and/or binding site. The resistance is generally due to a mutation in the gene encoding the target of the SDHI fungicide, i.e. in the fungi succinate dehydrogenase gene.

The target enzyme of SDHI fungicides is succinate dehydrogenase (SDH, so-called complex II in the mitochondrial respiration chain) which is a functional part of the tricarboxylic cycle and linked to the mitochondrial electron transport chain. SDH consists of four subunits (A, B, C and D) and the binding site of ubiquitone (and SDHIs) is formed by the subunits B, C and D.

[0013] SDHI fungicides belong generally to two classes of compounds, i.e. benzamide derivatives or carboxamide derivatives. Cases of resistance and often cross-resistance of fungi species against SDHI fungicides are known in field populations and lab mutants. The above-mentioned SDHI fungicides are in general cross-resistant and have been grouped under the FRAC code N°7 in the revised FRAC code list visible on the FRAC site (http://www.frac.info/frac/work/work sdhi.htm). FRAC code N°7 (October 2012)

[0014] In a particular embodiment of the invention, compound of formula (I) or salt thereof are used for treating plants curatively and/or preventively against at least one resistant strain of fungi which is resistant to at least one SDHI (succinate dehydrogenase inhibitor) fungicide which is a benzamide or carboxamide derivative.

[0015] In a particular embodiment of the invention, compound of formula (I) or salt thereof are used for treating plants curatively and/or preventively against at least one resistant strain of fungi which is resistant to at least one SDHI (succinate dehydrogenase inhibitor) fungicide which belongs to a chemical group selected in the list of phenyl-benzamides, pyridinyl-ethyl-benzamides, furan-carboxamides, oxathiin-carboxamides, thiazole-carboxamides, pyrazole-carboxamides and pyridine-carboxamides.

In a particular embodiment of the invention, compound of formula (I) or salt thereof are used for treating plants curatively and/or preventively against at least one resistant strain of fungi which is resistant to at least one SDHI (succinate dehydrogenase inhibitor) fungicide selected in the list consisting of benodanil, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, trifluzamid, benzovindiflupyr, isofetamid.

[0016] A list of fungal species with resistance reports towards SDHI fungicides and the corresponding mutations in the succinate dehydrogenase gene is regularly published by the FRAC, and visible on their site http://www.frac.info/frac/work/work sdhi.htm.

The fungal species with resistance reports cited in the FRAC updated March 2012 document are

Ustilago maydis, Mycosphaerella graminicola, Aspergillus oryzae, Botrytis cinerea, Botrytis elliptica, Alternaria alternata, Corynespora cassiicola, Didymella bryoniae, Podosphaera xanthii, Sclerotinia sclerotiorum and Stemphylium botryose, and the resistance mechanism (subunit mutation) are the following:

Species name I Resistance mechanism (subunit-mutation)

Ustilago maydis IB-H257L j I Mycosphaerella |B-H267Y/R/L ; B-I269V ; C-H152R ; C-N86K ; D-H139E | graminicola land many others j

Aspergillus oryzae (B-H249Y/L/N ; C-T90I ; D-D124E j

Botrytis cinerea |B-P225L/T/F ; B-H272Y/R/L ; B-N230I ; D-H132R j

{Botrytis elliptica IB-H272Y/R I

Alternaria alternata IB-H277Y/R ; C-H134R ; D-D123E ; D-H133R

{Corynespora cassiicola IB-H287Y/R ; C-S73P ; D-S89P I

{Didymella bryoniae |B-H277R/Y I

{Podosphaera xanthii |B-H->Y J

{Sclerotinia sclerotiorum ID-H132R I

{Stemphylium botryose |B-P225L ; H272Y/R

[0017] In a particular embodiment of the invention, compound of formula (I) or salt thereof are used for treating plants curatively and/or preventively against at least one resistant strain of fungi, resistant to at least one SDHI (succinate dehydrogenase inhibitor) fungicide, selected in the list consisting of Ustilago maydis, Mycosphaerella graminicola, Aspergillus oryzae, Botrytis cinerea, Botrytis elliptica, Alternaria alternata, Corynespora cassiicola, Didymella bryoniae, Podosphaera xanthii, Sclerotinia sclerotiorum and Stemphylium botryose.

[0018] In a particular embodiment of the invention, compound of formula (I) or salt thereof are used for treating plants curatively and/or preventively against at least one resistant strain of fungi resistant to at least one SDHI (succinate dehydrogenase inhibitor) fungicide wherein the fungi resistance to fungicide is conferred by a mutation on the amino acid at position 73, 86, 89, 90,123,124, 132, 133, 134,139, 152, 225, 230, 249, 257, 267, 269, 272, 277 or 287 in the sequence of the succinate dehydrogenase from said fungi. More particularly on mutation at position 225.

[0019] In a particular embodiment of the invention, compound of formula (I) or salt thereof are used for treating plants curatively and/or preventively against at least one resistant strain of fungi resistant to at least one SDHI (succinate dehydrogenase inhibitor) fungicide wherein the fungi resistance to fungicide is conferred by a mutation selected from the list of the following mutations in the amino acid sequence of the succinate dehydrogenase from said fungi: B-H257L; B-H267Y/R/L ; B-I269V ; C-H152R ; C-N86K ; D-H139E; B-H249Y/L/N ; C-T90I ; D-D124E ; B-P225L/T/F/H ; B-H272Y/R/L ; B-N230I ; D-H132R; B-H277Y/R ; C-H134R ; D-D123E ; D-H133R; B-H287Y/R ; C-S73P ; D-S89P; D-H132R. More particularly B-P225L/T/F/H.

[0020] The application rates of the compounds of formula (I) used in the method of the present invention are generally from 0.005 to 0.5 kg/ha, preferably 0.01 to 0.2 kg/ha, in particular 0.02 to 0.1 kg/ha.

[0021] For seed treatment, the application rates are generally from 0.001 to 250 g/kg of seeds, preferably 0.01 to 100 g/kg, in particular 0.01 to 50 g/kg.

[0022] The compounds of formula (I) used in the method of the present invention can be formulated for example in the form of ready-to-spray solutions, powders and suspensions or in the form of highly concentrated aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting or granules, and applied by spraying, atomizing, dusting, broadcasting or watering. The use form depends on the intended purpose; in any case, it should ensure as fine and uniform as possible a distribution of the mixture according to the invention.

[0023] The formulations are prepared in a known manner, e. g. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants, it being possible also to use other organic solvents as auxiliary solvents if water is used as the diluent. Suitable auxiliaries for this purpose are essentially: solvents such as aromatics (e. g. xylene), chlorinated aromatics (e. g. chlorobenzenes), paraffins (e. g. mineral oil fractions), alcohols (e. g. methanol, butanol), ketones (e. g. cyclohexanone), amines (e. g. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (e. g. kaolins, clays, talc, chalk) and ground synthetic minerals (e. g. finely divided silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (e. g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignosulfite waste liquors and methylcellulose.

[0024] Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e. g. ligno-, phenol-, naphthalene-and dibutyinaphthalenesulfonic acid, and of fatty acids, alkyl-and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfate hexa-, hepta-and octadecanols, or of fatty alcohol glycol ethers, condensates of sulfonate naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl-or nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors or methylcellulose.

[0025] Powders, materials for broadcasting and dusts can be prepared by mixing or jointly grinding the compounds of formula (I) I with a solid carrier.

[0026] Granules (e. g. coated granules, impregnated granules or homogeneous granules) are usually prepared by binding the active ingredient, or active ingredients, to a solid carrier.

[0027] Fillers or solid carriers are, for example, mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials and fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders or other solid carriers.

[0028] The formulations generally comprise from 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of the compound. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum or HPLC).

[0029] The compounds according to the invention may also be present in combination with other active compounds, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers. In many cases, a mixture of the compounds of formula (I), or of the compositions comprising them, in the use form as growth promoters with other active compounds results in a broader spectrum of activity.

The following list of fungicides in combination with which the compounds according to the invention can be used is intended to illustrate the possible combinations, but not to impose any limitation:

The active ingredients specified herein by their "common name" are known and described, for example, in the Pesticide Manual or can be searched in the internet (e.g. http://www.alanwood.net/pesticides).

Where a compound (A) or a compound (B) can be present in tautomeric form, such a compound is understood hereinabove and herein below also to include, where applicable, corresponding tautomeric forms, even when these are not specifically mentioned in each case. 1. 1) Inhibitors of the ergosterol biosynthesis, for example (1.1) aldimorph, (1.2) azaconazole, (1.3) bitertanol, (1.4) bromuconazole, (1.5) cyproconazole, (1.6) diclobutrazole, (1.7) difenoconazole, (1.8) diniconazole, (1.9) diniconazole-M, (1.10) dodemorph, (1.11) dodemorph acetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamid, (1.17) fenpropidin, (1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafol, (1.23) furconazole, (1.24) furconazole-cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalil sulfate, (1.28) imibenconazole, (1.29) ipconazole, (1.30) metconazole, (1.31) myclobutanil, (1.32) naftifine, (1.33) nuarimol, (1.34) oxpoconazole, (1.35) paclobutrazol, (1.36) pefurazoate, (1.37) penconazole, (1.38) piperalin, (1.39) prochloraz, (1.40) propiconazole, (1.41) prothioconazole, (1.42) pyributicarb, (1.43) pyrifenox, (1.44) quinconazole, (1.45) simeconazole, (1.46) spiroxamine, (1.47) tebuconazole, (1.48) terbinafine, (1.49) tetraconazole, (1.50) triadimefon, (1.51) triadimenol, (1.52) tridemorph, (1.53) triflumizole, (1.54) triforine, (1.55) triticonazole, (1.56) uniconazole, (1.57) uniconazole-p, (1.58) viniconazole, (1.59) voriconazole, (1.60) 1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, (1.61) methyl 1-(2,2-dimethyl-2,3-dihydro-1H-inden-1 -yl)-1 H-imidazole-5-carboxylate, (1.62) N'-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide, (1.63) N-ethyl-N-methyl-N'-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide, (1.64) 0-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl] 1 H-imidazole-1-carbothioate, (1.65) Pyrisoxazole. 2. 2) Inhibitors of the respiratory chain at complex I or II, for example (2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4) diflumetorim, (2.5) fenfuram, (2.6) fluopyram, (2.7) flutolanil, (2.8) fluxapyroxad, (2.9) furametpyr, (2.10) furmecyclox, (2.11) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (2.12) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (2.13) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.14) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (2.15) isopyrazam (syn epimeric racemate 1RS,4SR,9RS), (2.16) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.18) mepronil, (2.19) oxycarboxin, (2.20) penflufen, (2.21) penthiopyrad, (2.22) sedaxane, (2.23) thifluzamide, (2.24) 1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1 H-pyrazole-4-carboxamide, (2.25) 3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide, (2.26) 3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1 H-pyrazole-4-carboxamide, (2.27) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl )-1 -methyl-1 H-pyrazole-4-carboxamide, (2.28) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.29) benzovindiflupyr, (2.30) N- [(1 S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1 -methyl-1 H-pyrazole-4-carboxamide, (2.31) N-[(1 R,4S)- 9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-l-methyl-1 H-pyrazole-4-carboxamide, (2.32) 3-(difluoromethyl)-l -methyl-N-(1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)-1 H-pyrazole-4-carboxamide, (2.33) 1,3,5-trimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)-1 H-pyrazole-4-carboxamide, (2.34) 1-methyl-3-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)-1 H-pyrazole-4-carboxamide, (2.35) 1-methyl-3-(trifluoromethyl)-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1 H-pyrazole-4-carboxamide, (2.36) 1-methyl-3-(trifluoromethyl)-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1 H-pyrazole-4-carboxamide, (2.37) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1 H-pyrazole-4-carboxamide, (2.38) 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1 H-pyrazole-4-carboxamide, (2.39) 1,3,5-trimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1 H-pyrazole-4-carboxamide, (2.40) 1,3,5-trimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.41) benodanil, (2.42) 2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)pyridine-3-carboxamide, (2.43) Isofetamid. 3. 3) Inhibitors of the respiratory chain at complex III, for example (3.1) ametoctradin, (3.2) amisulbrom, (3.3) azoxystrobin, (3.4) cyazofamid, (3.5) coumethoxystrobin, (3.6) coumoxystrobin, (3.7) dimoxystrobin, (3.8) enoxastrobin, (3.9) famoxadone, (3.10)fenamidone, (3.11) flufenoxystrobin, (3.12) fluoxastrobin, (3.13) kresoxim-methyl, (3.14) metominostrobin, (3.15) orysastrobin, (3.16) picoxystrobin, (3.17) pyraclostrobin, (3.18) pyrametostrobin, (3.19) pyraoxystrobin, (3.20) pyribencarb, (3.21) triclopyricarb, (3.22) trifloxystrobin, (3.23) (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide, (3.24) (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1 E)-1 -[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)acetamide, (3.25) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3- (trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}acetamide, (3.26) (2E)-2-{2-[({[(1 E)-1 -(3-{[(E)-1 -fluoro-2- phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.27) Fenaminostrobin, (3.28) 5-methoxy-2-methyl-4-(2-{[({(1 E)-1 -[3- (trifluoromethyl)phenyl]ethylidene}amino)oxymethyl}phenyl)-2,4-dihydro-3H- 1,2,4-triazol-3-one, (3.29) methyl (2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl}-3-methoxyacrylate, (3.30) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.31) 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.32) 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide; (3.33) (2E,3Z)-5-{[1 -(4-chlorophenyl)-1 H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide. 4. 4) Inhibitors of the mitosis and cell division, for example (4.1) benomyl, (4.2) carbendazim, (4.3) chlorfenazole, (4.4) diethofencarb, (4.5) ethaboxam, (4.6) fluopicolide, (4.7) fuberidazole, (4.8) pencycuron, (4.9) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate, (4.12) zoxamide, (4.13) 5-chloro-7-(4-methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine, (4.14) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine. 5. 5) Compounds capable to have a multisite action, for example (5.1) bordeaux mixture, (5.2) captafol, (5.3) captan, (5.4) chlorothalonil, (5.5) copper hydroxide, (5.6) copper naphthenate, (5.7) copper oxide, (5.8) copper oxychloride, (5.9) copper(2+) sulfate, (5.10) dichlofluanid, (5.11) dithianon, (5.12) dodine, (5.13) dodinefree base, (5.14) ferbam, (5.15) fluorofolpet, (5.16) folpet, (5.17) guazatine, (5.18) guazatine acetate, (5.19) iminoctadine, (5.20) iminoctadine albesilate, (5.21) iminoctadine triacetate, (5.22) mancopper, (5.23) mancozeb, (5.24) maneb, (5.25) metiram, (5.26) metiram zinc, (5.27) oxine-copper, (5.28) propamidine, (5.29) propineb, (5.30) sulfur and sulfur preparations including calcium polysulfide, (5.31) thiram, (5.32) tolylfluanid, (5.33) zineb, (5.34) ziram, (5.35) anilazine. 6. 6) Compounds capable to induce a host defence, for example (6.1) acibenzolar-S-methyl, (6.2) isotianil, (6.3) probenazole, (6.4) tiadinil, (6.5) laminarin. 7. 7) Inhibitors of the amino acid and/or protein biosynthesis, for example (7.1) andoprim, (7.2) blasticidin-S, (7.3) cyprodinil, (7.4) kasugamycin, (7.5) kasugamycin hydrochloride hydrate, (7.6) mepanipyrim, (7.7) pyrimethanil, (7.8) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1 -yl)quinoline, (7.9) oxytetracycline, (7.10) streptomycin. 8. 8) Inhibitors of the ATP production, for example (8.1) fentin acetate, (8.2) fentin chloride, (8.3) fentin hydroxide, (8.4) silthiofam. 9. 9) Inhibitors of the cell wall synthesis, for example (9.1) benthiavalicarb, (9.2) dimethomorph, (9.3) flumorph, (9.4) iprovalicarb, (9.5) mandipropamid, (9.6) polyoxins, (9.7) polyoxorim, (9.8) validamycin A, (9.9) valifenalate, (9.10) polyoxin B. 10.10) Inhibitors of the lipid and membrane synthesis, for example (10.1) biphenyl, (10.2) chloroneb, (10.3) dicloran, (10.4) edifenphos, (10.5) etridiazole, (10.6) iodocarb, (10.7) iprobenfos, (10.8) isoprothiolane, (10.9) propamocarb, (10.10) propamocarb hydrochloride, (10.11) prothiocarb, (10.12) pyrazophos, (10.13) quintozene, (10.14) tecnazene, (10.15) tolclofos-methyl. 11.11) Inhibitors of the melanin biosynthesis, for example (11.1) carpropamid, (11.2) diclocymet, (11.3) fenoxanil, (11.4) phthalide, (11.5) pyroquilon, (11.6) tricyclazole, (11.7) 2,2,2-trifluoroethyl {3-methyl-1 -[(4-methylbenzoyl)amino]butan-2-yl}carbamate. 12.12) Inhibitors of the nucleic acid synthesis, for example (12.1) benalaxyl, (12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate, (12.4) clozylacon, (12.5) dimethirimol, (12.6) ethirimol, (12.7) furalaxyl, (12.8) hymexazol, (12.9) metalaxyl, (12.10) metalaxyl-M (mefenoxam), (12.11)ofurace, (12.12) oxadixyl, (12.13) oxolinic acid, (12.14) octhilinone. 13.13) Inhibitors of the signal transduction, for example (13.1) chlozolinate, (13.2) fenpiclonil, (13.3) fludioxonil, (13.4) iprodione, (13.5) procymidone, (13.6) quinoxyfen, (13.7) vinclozolin, (13.8) proquinazid. 14.14) Compounds capable to act as an uncoupler, for example (14.1) binapacryl, (14.2) dinocap, (14.3) ferimzone, (14.4) fluazinam, (14.5) meptyldinocap. 15.15) Further compounds, for example (15.1) benthiazole, (15.2) bethoxazin, (15.3) capsimycin, (15.4) carvone, (15.5) chinomethionat, (15.6) pyriofenone (chlazafenone), (15.7) cufraneb, (15.8) cyflufenamid, (15.9) cymoxanil, (15.10) cyprosulfamide, (15.11) dazomet, (15.12) debacarb, (15.13) dichlorophen, (15.14) diclomezine, (15.15) difenzoquat, (15.16) difenzoquat metilsulfate, (15.17) diphenylamine, (15.18) ecomate, (15.19) fenpyrazamine, (15.20) flumetover, (15.21) fluoroimide, (15.22) flusulfamide, (15.23) flutianil, (15.24) fosetyl-aluminium, (15.25) fosetyl-calcium, (15.26) fosety I-sodium, (15.27) hexachlorobenzene, (15.28) irumamycin, (15.29) methasulfocarb, (15.30) methyl isothiocyanate, (15.31) metrafenone, (15.32) mildiomycin, (15.33) natamycin, (15.34) nickel dimethyldithiocarbamate, (15.35) nitrothal-isopropyl, (15.37) oxamocarb, (15.38) oxyfenthiin, (15.39) pentachlorophenol and salts, (15.40) phenothrin, (15.41) phosphorous acid and its salts, (15.42) propamocarb-fosetylate, (15.43) propanosine-sodium, (15.44) pyrimorph, (15.45) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1 -(morpholin-4-yl)prop-2-en-1 -one, (15.46) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)- 1- (morpholin-4-yl)prop-2-en-1-one, (15.47) pyrrolnitrine, (15.48) tebufloquin, (15.49) tecloftalam, (15.50) tolnifanide, (15.51) triazoxide, (15.52) trichlamide, (15.53) zarilamid, (15.54) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate, (15.55) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1-yl]ethanone, (15.56) 1 -(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1 -yl)- 2- [5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1-yl]ethanone, (15.57) 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1 -yl)- 2- [5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1-yl]ethanone, (15.58) 1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl 1 H-imidazole-1-carboxylate, (15.59) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, (15.60) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, (15.61) 2,6-dimethyl-1H,5H- [1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone, (15.62) 2-[5-methyl- 3- (trifluoromethyl)-1 H-pyrazol-1 -yl]-1 -(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone, (15.63) 2-[5-methyl-3-(trifluoromethyl)-l H-pyrazol-1 -yl]-1 -(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone, (15.64) 2-[5-methyl-3-(trifluoromethyl)-l H-pyrazol-1 -yl]-1 -{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone, (15.65) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.66) 2-chloro-5-[2-chloro-1 -(2,6-difluoro-4-methoxyphenyl)-4-methyl-1 H-imidazol-5-yl]pyridine, (15.67) 2-phenylphenol and salts, (15.68) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.69) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (15.70) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (15.71) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (15.72) 5-amino- 1.3.4- thiadiazole-2-thiol, (15.73) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide, (15.74) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.75) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.76) 5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, (15.77) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.78) N'-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (15.79) N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1 -yloxy)phenyl]propanamide, (15.80) N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide, (15.81) N-[(5-bromo-3-chloropyridin-2-yl)methyl]- 2.4- dichloronicotinamide, (15.82) N-[1 -(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide, (15.83) N-[1 -(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide, (15.84) N-{(E)-[(cyclopropylmethoxy)imino][6- (difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, (15.85) N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, (15.86) N'-{4-[(3-tert-butyl-4-cyano- 1.2- thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylimidoformamide, (15.87) N-methyl-2-(1 -{[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1 -yl)- 1.3- thiazole-4-carboxamide, (15.88) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-l H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-N-[(1 R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide, (15.89) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-N-[(1 S)- 1,2,3,4-tetrahydronaphthalen-1 -yl]-1,3-thiazole-4-carboxamide, (15.90) pentyl {6-[({[(1-methyl-1 H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.91) phenazine-1-carboxylic acid, (15.92) quinolin-8-ol, (15.93) quinolin-8-ol sulfate (2:1), (15.94) tert-butyl {6-[({[(1-methyl-1 H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.95) 1 -methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (15.96) N-(4'-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1 -methyl-1 H-pyrazole-4-carboxamide, (15.97) N-(2',4'-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-l -methyl-1 H-pyrazole-4-carboxamide, (15.98) 3-(difluoromethyl)-1-methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (15.99) N-(2',5'-difluorobiphenyl-2-yl)-1 -methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, (15.100) 3-(difluoromethyl)-1-methyl-N-[4'-(prop-1 -yn-1 -yl)biphenyl-2-yl]-1 H-pyrazole-4-carboxamide, (15.101) 5-fluoro-1,3-dimethyl-N-[4'-(prop-1 -yn-1 -yl)biphenyl-2-yl]-1 H-pyrazole-4-carboxamide, (15.102) 2-chloro-N-[4'-(prop-1 -yn-1 -yl)biphenyl-2-yl]nicotinamide, (15.103) 3-(difluoromethyl)-N-[4'-(3,3-dimethylbut-1 -yn-1 -yl)biphenyl-2-yl]-1 -methyl-1 H-pyrazole-4-carboxamide, (15.104) N-[4'-(3,3-dimethylbut-1 -yn-1 -yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1 H-pyrazole-4-carboxamide, (15.105) 3-(difluoromethyl)-N-(4'-ethynylbiphenyl-2-yl)-1 -methyl-1 H-pyrazole-4-carboxamide, (15.106) N-(4'-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1 H-pyrazole-4-carboxamide, (15.107) 2-chloro-N-(4'-ethynylbiphenyl-2-yl)nicotinamide, (15.108) 2-chloro-N-[4'-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide, (15.109) 4-(difluoromethyl)-2-methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide, (15.110) 5-fluoro-N-[4'-(3-hydroxy-3-methylbut-1 -yn-1 -yl)biphenyl-2-yl]-1,3-dimethyl-1 H-pyrazole- 4-carboxamide, (15.111) 2-chloro-N-[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide, (15.112) 3-(difluoromethyl)-N-[4'-(3-methoxy-3-methylbut-1 -yn-1 -yl)biphenyl-2-yl]-1 -methyl-1 H-pyrazole-4-carboxamide, (15.113) 5-fluoro-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1 H-pyrazole-4-carboxamide, (15.114) 2-chloro-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide, (15.115) (5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone, (15.116) N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulfonyl)valinamide, (15.117) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.118) but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1 H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.119) 4-amino-5-fluoropyrimidin-2-ol(tautomeric form: 4-amino-5-fluoropyrimidin-2(1 H)-one), (15.120) propyl 3,4,5-trihydroxybenzoate, (15.121) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)-1 H-pyrazole-4-carboxamide, (15.122) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1 H- pyrazole-4-carboxamide, (15.123) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (15.124) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.125) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.126) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.127) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.128) 1 -{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1 H-1,2,4-triazol-5-yl thiocyanate, (15.129) 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (15.130) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.131)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.132) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.133) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (15.134) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (15.135) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1 H-1,2,4-triazole, (15.136) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1 H-1,2,4-triazole, (15.137) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.138) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.139) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.140) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy- 2.6.6- trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.141) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.142)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.143) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy- 2.6.6- trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.144) 2-[(2S,4R,SS)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.145) 2-fluoro-6-(trifluoromethyl)-N- (1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)benzamide, (15.146) 2-(6-benzylpyridin-2-yl)quinazoline, (15.147) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.148) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.149) Abscisic acid, (15.150) 3-(d ifl uoromethyl)-N-methoxy-1 -methyl-N-[1 -(2,4,6-trichlorophenyl )propan-2-yl]-1 H-pyrazole-4-carboxamide, (15.151) N'-[5-bromo-6-(2,3-dihydro-1 H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, (15.152) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (15.153) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (15.154) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (15.155) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (15.156) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N- methylimidoformamide, (15.157) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1 -methyl-1 H-pyrazole-4-carboxamide, (15.158) N-cyclopropyl-N-(2-cyclopropylbenzyl )-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide, (15.159) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide, (15.160) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide, (15.161) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1 -methyl-1 H-pyrazole-4-carboxamide, (15.162) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1 -methyl-1 H-pyrazole-4-carboxamide, (15.163) N-cyclopropyl-3-(difluoromethyl)- 5- fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1 H-pyrazole-4-carboxamide, (15.164) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide, (15.165) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide, (15.166) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro- 6- isopropylbenzyl)-1 -methyl-1 H-pyrazole-4-carboxamide, (15.167) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluorc>-1-methyl-1 H-pyrazole-4-carboxamide, (15.168) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1 H-pyrazole-4-carboxamide, (15.169) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1 -methyl-1 H-pyrazole-4-carboxamide, (15.170) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1 -methyl-1 H-pyrazole-4-carboxamide, (15.171) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide, (15.172) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (15.173) N- [2-chloro-6-(trifluoromethyl)benzyl] -N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-H-pyrazole-4-carboxamide, (15.174) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide, (15.175) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl- 4.5- dimethylbenzyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide, (15.176) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1 H-pyrazole-4-carbothioamide, (15.177) 3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl)-1 -methyl-1 H-pyrazole-4-carboxamide, (15.178) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1-methyl-1 H-pyrazole-4-carboxamide, (15.179) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1-methyl-1 H-pyrazole-4-carboxamide, (15.180) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (15.181) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]- 2.5- dimethylphenylJ-N-ethyl-N-methylimidoformamide, (15.182) N-(4-chloro- 2.6- difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine; (15.183) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 H-1,2,4-triazol-1-yl)propan-2-ol, (15.184) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 H-1,2,4-triazol-1-yl)butan-2-ol, (15.185) 2-(4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 H-1,2,4-triazol-1 -yl)pentan-2-ol, (15.186) 2- [2-chloro-4-(4-chlorophenoxy)phenyl]-1 -(1 H-1,2,4-triazol-1 -yl)butan-2-ol, (15.187) 2- [2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H- 1,2,4-triazol-1-yl)propan-2-ol, (15.188) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)- 2,3-dihydro-1,4-benzoxazepine, (15.189) 2-{2-fluoro-6-[(8-fluoro-2- methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.190) 2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol.

[0030] All named mixing partners of the classes (1) to (15) can, if their functional groups enable this, optionally form salts with suitable bases or acids.

[0031] The precise amount of compound according to the invention may depend upon the particular plant species being treated. This may be determined by the man skilled in the art with a few experiments and may vary in plant responses depending upon the total amount of compound used, as well as the particular plant species, which is being treated. Of course, the amount of compound should be non-phytotoxic with respect of the plant being treated.

[0032] Although a particularly suitable method of application of the compounds used in the process of this invention is directly to the foliage, fruits and stems of plants, such compounds may be also applied to the soil in which the plants are growing.

They will then be root-absorbed to a sufficient extent so as to result in plant responses in accordance with the teachings of this invention. The compounds of the invention may also be provided to the treated crop by seed-treatment.

[0033] The compounds of the invention are able to regulate plant growth both for monocotyledonous or dicotyledonous plants.

Among the plants that can be protected by the method according to the invention, mention can be made of cotton; flax; vine; fruit or vegetable crops such as Rosaceae sp. (for instance pip fruit such as apples and pears, but also stone fruit such as apricots, almonds and peaches), Ribesioidae sp., Juglaudaceae sp., Betulaceae sp., Auacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actiuidaceae sp., Lauraceae sp., Musaceae sp. (for instance banana trees and plantins), Rubiaceae sp., Theaceae sp., Sterculiceae sp., Rutaceae sp. (for instance lemons oranges and grapefruit); Solanaceae sp. (for instance tomatoes), Liliaceae sp., Asteraceae sp. (for instance lettuces), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp., Papilionaceae sp. (for instance peas), Rosaceae sp. (for instance strawberries); major crops such as Graminae sp. (for instance maize, lawn or cereals such as wheat, rice, barley and triticale), Asteraceae sp. (for instance sunflower), Cruciferae sp. (for instance colza), Fabacae sp. (for instance peanuts), Papilionaceae sp. (for instance soybean), Solanaceae sp. (for instance potatoes), Cheuopodiaceae sp. (for instance beetroots); horticultural crops such as Rosaceae sp. (for examples rose) and forest crops; oil-rich plants such as Brassicaceae sp. (for instance oilseed rape), Asteraceae sp. (for instance sunflower); grasses such as turf, as well as genetically modified homologues of these crops.

The compounds of the invention are particularly suitable for regulating plant growth of cotton, vine, cereals (such as wheat, rice, barley, triticale), 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.

[0034] According to the invention all plants and plant parts can be treated. By plants is 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. By plant parts is 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.

Among the 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. (for instance pip fruit such as apples and pears, but also stone fruit such as apricots, cherries, almonds and peaches, berry fruits such as strawberries), Ribesioidae sp., Juglaudaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oieaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for instance banana trees and plantings), Rubiaceae 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., Compositiae sp. (for instance lettuce, artichoke and chicory -including root chicory, endive or common chicory), Umbelliferae sp. (for instance carrot, parsley, celery and celeriac), Cucurbitaceae sp. (for instance cucumber -including pickling cucumber, squash, watermelon, gourds and melons), Alliaceae sp. (for instance onions and leek), 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), Cheuopodiaceae sp. (for instance mangold, spinach beet, spinach, beetroots), Malvaceae (for instance okra), Asparagaceae (for instance asparagus); horticultural and forest crops; ornamental plants; as well as genetically modified homologues of these crops.

[0035] The method of treatment according to the invention can be used in the treatment of genetically modified organisms (GMOs), e.g. plants or seeds.

Genetically modified plants (or transgenic 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 improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression technology, RNA interference - RNAi - technology or microRNA -miRNA - 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.

[0036] Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, 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.

[0037] At certain application rates, 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. In the present case, unwanted microorganisms are to be understood as meaning phytopathogenic fungi, bacteria and viruses. Thus, 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 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds.

[0038] 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. Examples of nematode resistant plants are described in e.g. US Patent Application Nos 11/765,491, 11/765,494, 10/926,819, 10/782,020, 12/032,479, 10/783,417, 10/782,096, 11/657,964, 12/192,904, 11/396,808, 12/166,253, 12/166,239, 12/166,124, 12/166,209, 11/762,886, 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 W011/002992, W011/014749, W011/103247, W011/103248.

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.

[0039] 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. In that case, and especially when seed is the desired product to be harvested from the hybrid plants it is typically useful to ensure that male fertility in the hybrid plants is fully restored. This can be accomplished by ensuring that the male parents have appropriate fertility restorer genes which are capable of restoring the male fertility in hybrid plants that contain the genetic determinants responsible for male-sterility. Genetic determinants for male sterility may be located in the cytoplasm. Examples of cytoplasmic male sterility (CMS) were for instance described in Brassica species (WO 92/05251, WO 95/09910, WO 98/27806, WO 05/002324, WO 06/021972 and US 6,229,072). However, genetic determinants for male sterility can also be located in the nuclear 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).

[0040] 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. For example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS 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. (Barry et al., 1992, Curr. Topics Plant Physiol. 7,139-145), the genes encoding a Petunia EPSPS (Shah et al., 1986, Science 233, 478-481), a Tomato EPSPS (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289), or an Eleusine EPSPS (WO 01/66704). It can also be a mutated EPSPS as described in for example EP 0837944, WO 00/66746, WO 00/66747, WO02/26995, W011/000498. 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, 11/312,866, 11/315,678, 12/421,292, 11/400,598, 11/651,752, 11/681,285, 11/605,824, 12/468,205, 11/760,570, 11/762,526, 11/769,327, 11/769,255, 11/943801 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.

[0041] Other 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 11/760,602. 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 7,112,665.

Further herbicide-tolerant plants are also plants that are made tolerant to the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase (HPPD). HPPD is an enzyme that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is transformed into homogentisate. 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, W011/076877, W011/076882, W011/076885, W011/076889, W011/076892. 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 prephenate deshydrogenase (PDH) activity in addition to a gene encoding an HPPD-tolerant enzyme, as described in WO 2004/024928. Further, 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.

Still further herbicide resistant plants are plants that are made tolerant to acetolactate synthase (ALS) inhibitors. Known ALS-inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidines, pryimidinyoxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinone herbicides. Different mutations in the ALS enzyme (also known as acetohydroxyacid synthase, AHAS) are known to confer tolerance to different herbicides and groups of herbicides, as described for example in Tranel and Wright (2002, Weed Science 50:700-712), but also, in U.S. Patent No. 5,605,011, 5,378,824, 5,141,870, and 5,013,659. The production of sulfonylurea-tolerant plants and imidazolinone-tolerant plants is described in U.S. Patent Nos. 5,605,011; 5,013,659; 5,141,870; 5,767,361; 5,731,180; 5,304,732; 4,761,373; 5,331,107; 5,928,937; and 5,378,824; and international publication WO 96/33270. Other 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, W011/076345, WO2012058223 and US Patent Application No 61/288958.

Other 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.

[0042] 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: 1. 1) 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. (2005) at the Bacillus thuringiensis toxin nomenclature, online at: http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal portions thereof, e.g., proteins of the Cry protein classes CrylAb, CrylAc, Cry1B, Cry1C, Cry1D, Cry1F, 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 2. 2) 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 Cry1 A or Cry1 F proteins and the Cry2Aa or Cry2Ab or Cry2Ae proteins (US Patent Appl. No. 12/214,022 and EP 08010791.5); or 3. 3) 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 Cry1A.105 protein produced by corn event MON89034 (WO 2007/027777); or 4. 4) a protein of any one of 1) to 3) 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, such as the Cry3Bb1 protein in corn events MON863 or MON88017, or the Cry3A protein in corn event MIR604; or 5. 5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus, or an insecticidal portion thereof, such as the vegetative insecticidal (VIP) proteins listed at: http://www.lifesci.sussex.ac.uk/home/Neil CrickmoreBt/vip.html. e.g., proteins from the VIP3Aa protein class; or 6. 6) 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 7. 7) 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. 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 COT102; or 9. 9) 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 Cry1 A or Cry1 F (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). 10.10) a protein of 9) 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) [0043] Of course, an insect-resistant transgenic plant, as used herein, also includes any plant comprising a combination of genes encoding the proteins of any one of the above classes 1 to 10. In one embodiment, 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.

[0044] 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 RNA 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.

[0045] 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: 1. 1) plants which contain a transgene capable of reducing the expression and/or the activity of poly(ADP-ribose) polymerase (PARP) gene in the plant cells or plants as described in WO 00/04173, WO/2006/045633, EP 04077984.5, or EP 06009836.5. 2. 2) plants which contain a stress tolerance enhancing transgene capable of reducing the expression and/or the activity of the PARG encoding genes of the plants or plants cells, as described e.g. in WO 2004/090140. 3. 3) plants which contain a stress tolerance enhancing transgene coding for a plant-functional enzyme of the nicotineamide adenine dinucleotide salvage synthesis pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyl transferase, nicotinamide adenine dinucleotide synthetase or nicotine amide phosphorybosyltransferase as described e.g. in EP 04077624.7, WO 2006/133827, PCT/EP07/002433, EP 1999263, or WO 2007/107326.

[0046] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention 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 : 1. 1) 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. Said 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 97/11188, 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 2005/095619, WO 2005/095618, WO 2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823, WO 00/22140, WO 2006/063862, WO 2006/072603, WO 02/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP 07090009.7, WO 01/14569, WO 02/79410, WO 03/33540, WO 2004/078983, WO 01/19975, WO 95/26407, WO 96/34968, WO 98/20145, WO 99/12950, WO 99/66050, WO 99/53072, US 6,734,341, WO 00/11192, WO 98/22604, WO 98/32326, WO 01/98509, WO 01/98509, WO 2005/002359, US 5,824,790, US 6,013,861, WO 94/04693, WO 94/09144, WO 94/11520, WO 95/35026, WO 97/20936, WO 10/012796, WO 10/003701 2. 2) 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. WO 00/47727, WO 00/73422, EP 06077301.7, US 5,908,975 and EP 0728213, 3. 3) transgenic plants which produce hyaluronan, as for example disclosed in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, JP 2006304779, and WO 2005/012529. 4. 4) 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. 5. 5) Transgenic plants displaying an increase yield as for example disclosed in W011/095528 [0047] Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) 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: 1. a) Plants, such as cotton plants, containing an altered form of cellulose synthase genes as described in WO 98/00549 2. b) Plants, such as cotton plants, containing an altered form of rsw2 or rsw3 homologous nucleic acids as described in WO 2004/053219 3. c) Plants, such as cotton plants, with increased expression of sucrose phosphate synthase as described in WO 01/17333 4. d) Plants, such as cotton plants, with increased expression of sucrose synthase as described in WO 02/45485 5. e) Plants, such as cotton plants, wherein the timing of the plasmodesmatal gating at the basis of the fiber cell is altered, e.g. through downregulation of fiber-selective p-1,3-glucanase as described in WO 2005/017157, or as described in EP 08075514.3 or US Patent Appl. No. 61/128,938 6. f) 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 W011/089021, WO2012074868 [0048] Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) 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: 1. a) Plants, such as oilseed rape plants, producing oil having a high oleic acid content as described e.g. in US 5,969,169, US 5,840,946 or US 6,323,392 or US 6,063,947 2. b) Plants such as oilseed rape plants, producing oil having a low linolenic acid content as described in US 6,270,828, US 6,169,190, US 5,965,755, or W011/060946. 3. c) Plant such as oilseed rape plants, producing oil having a low level of saturated fatty acids as described e.g. in US Patent No. 5,434,283 or US Patent Application No 12/668303 4. d) Plants such as oilseed rape plants, producing oil having an aleter glucosinolate content as described in WO2012075426.

[0049] Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) 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, W009/068313, W010/006732 and WO2012090499.

[0050] Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) 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 [0051] 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. At any time this information is readily available from APHIS (4700 River Road

Riverdale, MD 20737, USA), for instance on its internet site (URL http://www.aphis.usda.gov/brs/not_reg.html). On the filing date of this application the petitions for nonregulated status that were pending with APHIS or granted by APHIS were those which contains the following information: • 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. • Institution : the name of the entity submitting the petition. • Regulated article : the plant species concerned. • 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.

[0052] Additional particularly useful plants containing single transformation events or combinations of transformation events are listed for example in the databases from various national or regional regulatory agencies (see for example httD://amoinfo.irc.it/amD browse.aspx and http://www.agbios.com/dbase.php).

[0053] 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 1143-14A (cotton, insect control, not deposited, described in W02006/128569); Event 1143-51B (cotton, insect control, not deposited, described in W02006/128570); Event 1445 (cotton, herbicide tolerance, not deposited, described in US2002120964 or W02002/034946); 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 W02005/103266 or US2005216969); Event 3006-210-23 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in US2007143876 or W02005/103266); Event 3272 (corn, quality trait, deposited as PTA-9972, described in W02006098952 or US2006230473); Event 40416 (corn, insect control - herbicide tolerance, deposited as ATCC PTA-11508, described in WO2011/075593); Event 43A47 (corn, insect control - herbicide tolerance, deposited as ATCC PTA-11509, described in WO2011/075595); Event 5307 (corn, insect control, deposited as ATCC PTA-9561, described in WO2010/077816); Event ASR-368 (bent grass, herbicide tolerance, deposited as ATCC PTA-4816, described in US2006162007 or W02004053062); Event B16 (corn, herbicide tolerance, not deposited, described in US2003126634); Event BPS-CV127-9 (soybean, herbicide tolerance, deposited as NCIMB No. 41603, described in WO2010/080829); Event CE43-67B (cotton, insect control, deposited as DSM ACC2724, described in US2009217423 or W02006/128573); Event CE44-69D (cotton, insect control, not deposited, described in US20100024077); Event CE44-69D (cotton, insect control, not deposited, described in W02006/128571); Event CE46-02A (cotton, insect control, not deposited, described in W02006/128572); Event COT102 (cotton, insect control, not deposited, described in US2006130175 or W02004039986); Event COT202 (cotton, insect control, not deposited, described in US2007067868 or W02005054479); Event COT203 (cotton, insect control, not deposited, described in W02005/054480); Event DAS40278 (corn, herbicide tolerance, deposited as ATCC PTA-10244, described in WO2011/022469); Event DAS-59122-7 (corn, insect control - herbicide tolerance, deposited as ATCC PTA 11384 , described in US2006070139); Event DAS-59132 (corn, insect control -herbicide tolerance, not deposited, described in W02009/100188); Event DAS68416 (soybean, herbicide tolerance, deposited as ATCC PTA-10442, described in WO2011/066384 or WO2011/066360); Event DP-098140-6 (corn, herbicide tolerance, deposited as ATCC PTA-8296, described in US2009137395 or W02008/112019); Event DP-305423-1 (soybean, quality trait, not deposited, described in US2008312082 or W02008/054747); Event DP-32138-1 (corn, hybridization system, deposited as ATCC PTA-9158, described in US20090210970 or W02009/103049); Event DP-356043-5 (soybean, herbicide tolerance, deposited as ATCC PTA-8287, described in US20100184079 or W02008/002872); Event EE-1 (brinjal, insect control, not deposited, described in W02007/091277); Event FI117 (corn, herbicide tolerance, deposited as ATCC 209031, described in US2006059581 or W01998/044140); Event GA21 (corn, herbicide tolerance, deposited as ATCC 209033, described in US2005086719 or W01998/044140); Event GG25 (corn, herbicide tolerance, deposited as ATCC 209032, described in US2005188434 or W01998/044140); Event GHB119 (cotton, insect control - herbicide tolerance, deposited as ATCC PTA-8398, described in W02008/151780); Event GHB614 (cotton, herbicide tolerance, deposited as ATCC PTA-6878, described in US2010050282 or W02007/017186); Event GJ11 (corn, herbicide tolerance, deposited as ATCC 209030, described in US2005188434 or W01998/044140);

Event GM RZ13 (sugar beet, virus resistance , deposited as NCIMB-41601, described in WO2010/076212); Event H7-1 (sugar beet, herbicide tolerance, deposited as NCIMB 41158 or NCIMB 41159, described in US2004172669 or W02004/074492); Event JOPLIN1 (wheat, disease tolerance, not deposited, described in US2008064032); Event LL27 (soybean, herbicide tolerance, deposited as NCIMB41658, described in W02006/108674 or US2008320616); Event LL55 (soybean, herbicide tolerance, deposited as NCIMB 41660, described in W02006/108675 or US2008196127); Event LLcotton25 (cotton, herbicide tolerance, deposited as ATCC PTA-3343, described in W02003013224 or US2003097687);

Event LLRICE06 (rice, herbicide tolerance, deposited as ATCC-23352, described in US6468747 or W02000/026345); Event LLRICE601 (rice, herbicide tolerance, deposited as ATCC PTA-2600, described in US20082289060 or W02000/026356); Event LY038 (corn, quality trait, deposited as ATCC PTA-5623, described in US2007028322 or W02005061720); Event MIR162 (corn, insect control, deposited as PTA-8166, described in US2009300784 or W02007/142840); Event MIR604 (corn, insect control, not deposited, described in US2008167456 or W02005103301); Event MON15985 (cotton, insect control, deposited as ATCC PTA-2516, described in US2004-250317 or W02002/100163); Event MON810 (corn, insect control, not deposited, described in US2002102582); Event MON863 (corn, insect control, deposited as ATCC PTA-2605, described in W02004/011601 or US2006095986); Event MON87427 (corn, pollination control, deposited as ATCC PTA-7899, described in WO2011/062904); Event MON87460 (corn, stress tolerance, deposited as ATCC PTA-8910, described in W02009/111263 or US20110138504); Event MON87701 (soybean, insect control, deposited as ATCC PTA-8194, described in US2009130071 or W02009/064652); Event MON87705 (soybean, quality trait -herbicide tolerance, deposited as ATCC PTA-9241, described in US20100080887 or WO2010/037016); Event MON87708 (soybean, herbicide tolerance, deposited as ATCC PTA9670, described in WO2011/034704); Event MON87754 (soybean, quality trait, deposited as ATCC PTA-9385, described in WO2010/024976); Event MON87769 (soybean, quality trait, deposited as ATCC PTA-8911, described in US20110067141 or W02009/102873); Event MON88017 (corn, insect control -herbicide tolerance, deposited as ATCC PTA-5582, described in US2008028482 or W02005/059103); Event MON88913 (cotton, herbicide tolerance, deposited as ATCC PTA-4854, described in W02004/072235 or US2006059590); Event MON89034 (corn, insect control, deposited as ATCC PTA-7455, described in W02007/140256 or US2008260932); Event MON89788 (soybean, herbicide tolerance, deposited as ATCC PTA-6708, described in US2006282915 or W02006/130436); Event MS11 (oilseed rape, pollination control-herbicide tolerance, deposited as ATCC PTA-850 or PTA-2485, described in W02001/031042); Event MS8, (oilseed rape, pollination control - herbicide tolerance, deposited as ATCC PTA-730, described in W02001/041558 or US2003188347); Event NK603 (corn, herbicide tolerance, deposited as ATCC PTA-2478, described in US2007-292854); Event PE-7 (rice, insect control, not deposited, described in W02008/114282); Event RF3, (oilseed rape, pollination control - herbicide tolerance, deposited as ATCC PTA-730, described in W02001/041558 or US2003188347); Event RT73 (oilseed rape, herbicide tolerance, not deposited, described in W02002/036831 or US2008070260); Event T227-1 (sugar beet, herbicide tolerance, not deposited, described in W02002/44407 or US2009265817); Event T25 (corn, herbicide tolerance, not deposited, described in US2001029014 or W02001/051654); Event T304-40 (cotton, insect control - herbicide tolerance, deposited as ATCC PTA-8171, described in US2010077501 or W02008/122406); Event T342-142 (cotton, insect control, not deposited, described in W02006/128568); Event TC1507 (corn, insect control - herbicide tolerance, not deposited, described in US2005039226 or W02004/099447); Event VIP1034 (corn, insect control- herbicide tolerance, deposited as ATCC PTA-3925., described in W02003/052073), Event 32316 (corn,insect control-herbicide tolerance,deposited as PTA-11507, described in WO2011/153186A1), Event 4114 (corn, insect control-herbicide tolerance,deposited as PTA-11506, described in WO2011/084621), event EE-GM3 / FG72 (soybean, herbicide tolerance, ATCC Accession N° PTA-11041, WO2011/063413A2), event DAS-68416-4 (soybean, herbicide tolerance, ATCC Accession N° PTA-10442, W02011/066360A1), event DAS-68416-4 (soybean, herbicide tolerance, ATCC Accession N° PTA-10442, WO2011/066384A1), event DP-040416-8 (corn, insect control, ATCC Accession N° PTA-11508, WO2011/075593A1), event DP-043A47-3 (corn, insect control, ATCC Accession N° PTA-11509, WO2011/075595A1), event DP-004114-3 (corn, insect control, ATCC Accession N° PTA-11506, WO2011/084621A1), event DP-032316-8 (corn, insect control, ATCC Accession N° PTA-11507, WO2011/084632A1), event MON-88302-9 (oilseed rape, herbicide tolerance, ATCC Accession N° PTA-10955, WO2011/153186A1), event DAS-21606-3 (soybean, herbicide tolerance, ATCC Accession No. PTA-11028, WO2012/033794A2), event MON-87712-4 (soybean, quality trait, ATCC Accession N°. PTA-10296, WO2012/051199A2), event DAS-44406-6 (soybean, stacked herbicide tolerance, ATCC Accession N°. PTA-11336, WO2012/075426A1), event DAS-14536-7 (soybean, stacked herbicide tolerance, ATCC Accession N°. PTA-11335, WO2012/075429A1), event SYN-000H2-5 (soybean, herbicide tolerance, ATCC Accession N°. PTA-11226, WO2012/082548A2), event DP-061061-7 (oilseed rape, herbicide tolerance, no deposit N° available, W02012071039A1), event DP-073496-4 (oilseed rape, herbicide tolerance, no deposit N° available, US2012131692), event 8264.44.06.1 (soybean, stacked herbicide tolerance, Accession N° PTA-11336, WO2012075426A2), event 8291.45.36.2 (soybean, stacked herbicide tolerance, Accession N°. PTA-11335, WO2012075429A2).

[0054] The present invention further relates to the use of a compound of formula (I) ' (i) wherein 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), 2-ethyl, 2-trimethylsilyl and 2-ethyl-4,5-dimethyl, or an agrochemically acceptable salt thereof, for treating plants curatively and/or preventively against at least one strain of fungi which is resistant to at least one SDHI (succinate dehydrogenase inhibitor) fungicide.

[0055] Preference is given to the use, for treating plants curatively and/or preventively against at least one resistant strain of fungi, of a compound of formula (I) selected from the group consisting of: N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1 H- pyrazole-4-carboxamide (compound A1), N-cydopropyl-N-(2-cydopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl- 1 H-pyrazole-4-carboxamide (compound A2), N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound A3), N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (compound A4), N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (compound A5), N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (compound A6), N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide (compound A7), N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound A8), N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound A9), N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1 H-pyrazole-4-carboxamide (compound A10), N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound A11), N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide (compound A12), N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (compound A13), N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (compound A14), N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound A15), N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1 H-pyrazole-4-carboxamide (compound A16), N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound A17), N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1 -methyl-1 H-pyrazole-4-carboxamide (compound A18). N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (compound A19), N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1 H-pyrazole-4-carbothio-amide (compound A20), N-cyclopropyl-3-(difluoromethyl )-N-(2-ethyl benzyl )-5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide (compound A21), and N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[2-(trimethylsilyl)benzyl]-1H-pyrazole-4-carboxamide (compound A22).

[0056] The invention refers to the use of a compound of formula (I) as herein defined for treating plants curatively and/or preventively against at least one resistant strain of fungi, wherein the strain of fungi is resistant to at least one SDHI (succinate dehydrogenase inhibitor) fungicide.

In a particular embodiment, the invention refers to the use of a compound of formula (I) as herein defined for treating plants curatively and/or preventively against at least one resistant strain of fungi, wherein the strain of fungi is resistant to at least one SDHI (succinate dehydrogenase inhibitor) fungicide which is a benzamide or carboxamide derivative.

In a particular embodiment, the invention refers to the use of a compound of formula (I) as herein defined for treating plants curatively and/or preventively against at least one resistant strain of fungi, wherein the SDHI fungicide belongs to a chemical group selected in the list of phenyl-benzamides, pyridinyl-ethyl-benzamide, furan-carboxamides, oxathiin-carboxamides, thiazole-carboxamides, pyrazole-carboxamides and pyridine-carboxamides.

In a particular embodiment, the invention refers to the use of a compound of formula (I) as herein defined for treating plants curatively and/or preventively against at least one resistant strain of fungi, wherein the SDHI fungicide is selected in the list consisting of benodanil, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, trifluzamid, benzovindiflupyr, isofetamid.

[0057] In a particular embodiment, the invention refers to the use of a compound of formula (I) as herein defined for treating plants curatively and/or preventively against at least one resistant strain of fungi, wherein the strain of fungi resistant to SDHI fungicides is selected in the list consisting of Ustilago maydis, Mycosphaerella graminicola, Aspergillus oryzae, Botrytis cinerea, Botrytis elliptica, Alternaria alternata, Coryuespora cassiicola, Didymella bryoniae, Podosphaera xanthii, Sclerotinia sclerotiorum and Stemphylium botryose [0058] In a particular embodiment, the compound of formula (I) as herein defined is applied to the plants or to the locus in which they grow at an application rate of from 0.005 kg/ha to 0.5 kg/ha of compound of formula (I), preferably 0.01 to 0.2 kg/ha, in particular 0.02 to 0.1 kg/ha.

[0059] In another particular embodiment, the compound of formula (I) as herein defined is applied as seed treatment at an application rate of from 0.001 to 250 g/kg of seeds, preferably 0.01 to 100 g/kg, in particular 0.01 to 50 g/kg.

[0060] In a particular embodiment, the plant is selected from the group consisting of cotton, vine, cereals (such as wheat, rice, barley, triticale), 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.

[0061] 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-1-methyl-1 H-pyrazole-4-carbonyl chloride according to WO-2007/087906 (process PI) and WO-2010/130767 (process P1 - step 10).

[0062] Substituted 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).

[0063] 3-(difluoromethyl)-5-fluoro-1 -methyl-1 H-pyrazole-4-carbonyl chloride can be prepared according to WO-2010/130767 (process P1 - steps 9 or 11) [0064] N-cyclopropyl thioamides of formula (I) wherein T represents a sulfur atom, can be prepared by thionation 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).

[0065] The following examples illustrate in a non limiting manner the preparation of the compounds of formula (I) according to the invention.

Preparation of N-cvclopropvl-3-fdifluoromethvl)-5-fluoro-N-(2-isopropvlbenzvh-1 -methyl-1 H-pyrazole-4-carboxamide (compound A1)

Step A : preparation of N-(2-isopropylbenzyl)cyclopropanamine [0066] To a solution of 55.5 g (971 mmol) of cyclopropanamine in 900 ml_ of methanol, are successively added 20 g of 3 Å molecular sieves and 73 g (1.21 mol) of acetic acid. 72 g (486 mmol) of 2-isopropyl-benzaldehyde are then added dropwise and the reaction mixture is further heated at reflux for 4 hours. The 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.

[0067] The hydrochloride salt can be prepared by dissolving N-(2-isopropylbenzyl)cyclopropanamine in diethyl-ether (1.4 ml_ / g) at 0 °C followed by addition of a 2 M solution of hydrochloric acid in diethylether (1.05 eq.). After a 2 hours stirring, N-(2-isopropylbenzyl)cyclopropanamine hydrochloride (1:1) is filtered off, washed by diethylether and dried under vacuum at 40 °C for 48 hours. Mp (melting point) = 149 °C

Step B : preparation of N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1 -methyl-1 H-pyrazole-4-carboxamide [0068] To 40.8 g (192 mmol) of N-(2-isopropylbenzyl)cyclopropanamine in 1 L of dry tetrahydrofurane are added at room temperature, 51 ml_ (366 mmol) of triethylamine. A solution of 39.4 g (174 mmol) of 3-(difluoromethyl)-5-fluoro-1 -methyl-1 H-pyrazole-4-carbonyl chloride in 800 ml_ of dry tetrahydrofurane is then added dropwise while maintaining the temperature below 34 °C. The reaction mixture is heated at reflux for 2 hours then left overnight at room temperature. Salts are filtered off and the filtrate is concentrated under vacuum to yield 78.7 g of a brown oil. Column chromatography on silica gel (750 g - gradient n-heptane/ethyl acetate) yields 53 g (71% yield) of N-cyclopropyl-3-(difluoromethyl )-5-fluoro-N-(2-isopropylbenzyl )-1-methyl-1 H-pyrazole-4-carboxamide as a yellow oil that slowly crystallizes. Mp = 76-79 °C.

[0069] In the same way, compounds A2 to A19, A21, A22 can be prepared according to the preparation described for compound A1.

Preparation of N-cvclopropvl-3-(difluoromethvl)-5-fluoro-N-(2-isopropylbenzvl)-1 -methvl-1 H-pvrazole-4-carbothioamide (compound A20) [0070] A solution of 14.6 g (65 mmol) of phosphorus pentasulfide and 48 g (131 mmol) of N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1 -methyl-1 H-pyrazole-4-carboxamide in 500 ml of dioxane are heated at 100 °C for 2 hours. 50 ml of water are then added and the reaction mixture is further heated at 100 °C for another hour. The cooled reaction mixture is filtered over a basic alumina cartridge. The cartridge is washed by dichloromethane and the combined organic extracts are dried over magnesium sulfate and concentrated under vacuum to yield 55.3 g of an orange oil. The residue is tritured with a few ml_ of diethyl-ether until crystallisation occurs. Crystals are filtered off and dried under vacuum at 40 °C for 15 hours to yield 46.8 g (88% yield) of N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1 H-pyrazole-4-carbothioamide. Mp = 64-70 °C. Table 1 provides the logP and NMR data (1H) of compounds A1 to A20.

In table 1, the 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 :

Temperature: 40 °C ; Mobile phases : 0.1% aqueous formic acid and acetonitrile ; linear gradient from 10% acetonitrile to 90% acetonitrile.

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.

[0071] The following examples are illustrative of methods of plant growth regulation according to the invention, but should not be understood as limiting the said instant invention.

Example I: Lack of cross resistance in highly boscalid-resistant field isolated [0072] Botrytis cinerea boscalid-resistant populations were collected from the field and characterized by sequencing the SDHB gene which encodes the subunit B of succinate dehydrogenase. Four to five strains with SDHB_P225H, F substitutions were retained for subsequent sensitivity assays in microtiter plate. IC50 oftest compounds were determined and resistance factors (RF) calculated as the ratio of IC50 mutant/IC50 WT (Bo47). The activity of compounds of formula (I) according to the invention was compared to Boscalid, Fluxapyroxad, Penthiopyrad and Isopyrazam (Table 1). Strains giving a RF below 10 were considered sensitive, moderately resistant when RF was comprised between 10 and 50, resistant above 50.

[0073] Our results nicely demonstrated that strains harboring P225H and F substitutions remained sensitive to compounds of formula (I) according to the invention whereas they became moderately resistant to isopyrazam and resistant to other tested SDHi inhibitors.

[0074] Additionally, one tested compound (Compound A18) was seen to be always more active on strains with P225 substitutions than on wild type strain. These results emphasize the potential of compounds of formula (I) according to the invention as resistance breakers of fungi strains resistant to SDHI fungicide, and particularly to strains having SDHB_P225H,F substitutions.

Table 1 : Cellular sensitivity of carboxamide resistant strains

Example 2 : Mitochondrial sensitivity of boscalid resistant mutants [0075] Compounds activity was investigated at the level of the mitochondrial target and compared to other SDH inhibitors. The 3884 isolate was collected from field and SDHB gene sequencing revealed a P225H substitution.

[0076] Mitochondria were extracted according to Cramer et al. (1983) Analytical biochemistry , 128, 384-392 and the mycelium prepared according to Fritz et al., (1993). Agronomie 13, 225-230 except that spore's incubation was pursued for 48 hours. SDH activity was measured by following DCPIP (2,6-dichlorphenol-indophenol) reduction at 595 nm overtime. To test SDH inhibitors, mitochondria were incubated with test compounds for 20 min prior the initiation of the reaction. Inhibition of the succinate-ubiquinone redutase activity was expressed as pl50 which represents the -Iog10 of the concentration inhibiting DCPIP reduction by 50% (IC50). pl50 obtained on mutated mitochondria were compared to those calculated for the Bo47 WT strain used as the reference in these experiments.

[0077] Our results showed that pl50 obtained with compounds of formula (I) according to the invention on mitochondria extracted from the 3884 strain (P225H substitution) are always higher or equal to those obtained on the reference strain (classification A). This demonstrates that SDHB P225H substitution does not compromise the activity of the compound of formula (I) on the Sdh complex while this mutation significantly affects the activity of other tested SDH inhibitors (pl50 reduction by more than one unit was commonly observed with other SDH inhibitors). To confirm these data, the IC50 of compounds of formula (I) according to the invention were recorded on the 3884 strain (P225H substitution) and compared to the Bo47 WT strain. As expected, compounds of formula (I) were still controlling the wild type and 3884 strains when the activity of other SDH inhibitors was impaired on the 3884 strain.

Table 2 : Sensitivity conferred by amino acid substitutions at the mitochondrial (PI50 value) and at the cellular (IC50) levels

REFERENCES CITED IN THE DESCRIPTION

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

Patent documents cited in the description • W02007087906A Γ00061 Γ00611 • WQ2009Q16220A Γ0008Ι [00641 • WQ2010130767A Γ00061 [00611 Γ00β31 Γ0084Ι • EP22S1331A [00061 • EP2Q12QQ1676W Γ00061 • EP2Q12Q01874W Γ00061 • WQ2Q1211Q464A Γ0007Ί • US11765491B Γ00381 • US11765494B Γ00381 • US10926819B Γ0038Ί • US10782020B Γ0038Ί • US12032479B Γ00381 • US10783417B Γ00381 • US10782096B Γ00381 • US11657964B Γ00381 . US12192904B Γ00381 • US11396808B ΙΌ0381 • US12166253B Γ00381 • US12166239B Γ00381 • US12188124B Γ00381 • US121682Q9B Γ00381 • US11762888B Γ00381 • US12384335B Γ00381 • US11783947B Γ00381 • US12252453B [00381 • US12209354B Γ00381 • US12491398B Γ00381 • US12497221Β Γ00381 • US12844832B Γ00381 • US12646Q04B Γ0038Ί • US127Q1Q58B [00381 • US12718059B Γ00381 • US12721595B Γ00381 • US12838591Β Γ00381 • W011002992A [00381 • WOi 1Q14749A [00381 • WOi 1103247A [00381 • WQ111Q3248A Γ00381 • WQ9205251A [00391 • WQ9509910A f00391 • WO9827806A Γ00391 • WOQ5QQ2324A [00391 • WQ08021972A Γ00391 • US8229072B Γ00391 • WQ8910398A [00391 • WQ9102089A Γ00391 • WOQ1887Q4A F004Q] • EP0837944A [00401 • WQ0Q86748A [0040] • WOOQ88747A [0040] • WO0228995A Γ00401 • WOi 1Q0Q498A [0040] • US5778760A [00401 • US5483175A [00401 • WO0238782A [00401 • W003092380A Γ00401 • WQ0S012S1SA Γ0040] • WOQ7Q24782A [0040] [0041] • WO01024815ΑΓ00401 • WQ03013228A Γ0040] • US11517991Β Γ00401 • US10739810B [00401 • US121394Q8B [00401 • US12352532B Γ00401 • US1131288SB Γ00401 • US11315878B Γ0040] • US12421292B Γ00401 • US1140Q598B Γ0040] • US11851752B [0040] • US11881285B Γ00401 • US11805824B Γ00401 • US12468205B Γ0040] • US11780570B Γ00401 • US11782528B Γ00401 • US11789327B [00401 • US11789255B Γ00401 • US11943801Β Γ00401 • US12382774B F004Q] • US11588811Β Γ00401 • US11185342B Γ0040Ί • US12384724B [0040] • US11185580B Γ00401 • US12423926B Γ0040] • US11780802B [00411 • US5581236A Γ00411 • US5848477A Γ0041] • US5646024A Γ00411 • US5273894A Γ0041] • US5837489A [0041] • US5278288A Γ00411 • US5739082A Γ0041] • US5908810A Γ0041] • US7112865B Γ00411 • WQ9638567A [0041] • W09924585A [00411 • WQ9924586A Γ00411 • WQ20Q9144079A [0041] • W02002048387A Γ00411 • US8788044B Γ0041Ί • W011078877A Γ00411 • W011078882A [00411 • W011076885A [0041] • W011078889A [00411 • W011078892A Γ00411 • WQ9934008A Γ00411 • WO0238787A [00411 • WQ20Q4Q24928A F00411 • WQ20Q71Q3587A [0041] • WQ2008150473A Γ00411 • US5605011A Γ0041] [00411 • US5378824A Γ00411 Γ00411 • US514187QA Γ00411 Γ00411 • US5Q13859A Γ00411 Γ00411 • US5787361A Γ00411 • US573118QA Γ00411 • US53Q4732A [0041] • US4781373A Γ00411 • US53311Q7A Γ0041] • US5928937A Γ0041] • WO9833270A [00411 • W02004040012A Γ00411 • WQ2Q041Q8529A Γ0041] • WQ2005020673A Γ00411 • W02005093093A [00411 • WQ20Q60Q7373A [00411 • W02006015376A Γ00411 • WQ2Q08024351Α Γ00411 • WO2Q06Q6Q634A Γ0041] • W011076345A [00411 • WQ2012058223A [0041Ί • US61288958B [0041] • US5084Q82A [00411 • WQ9741218A [0041] • US5773702A Γ00411 • WO99057965A [00411 • US5198599A Γ0041] • WOQ1Q85922A [00411 • ΕΡ1999141Α Γ00421 • WQ2Q07107302Α Γ0042] • US12249018Β [00421 • US12214Q22B Γ0042Ί [00421 • ΕΡ08010791Α Γ00421 Γ0042] • W02007027777A Γ00421 • WQ9421795A Γ00421 • US81128083Β Γ00421 • US61195019B Γ00421 • W020Q7080128Α [0044] • WQ2008129204Α Γ00441 • WQ2Q070744Q5A Γ0044] • WO2Q07Q8Q127Α Γ0044] • W02007035850A [00441 • WOQOQ4173A Γ0045Ί • W02008045633A Γ00451 • ΕΡ04077984Α Γ00451 • EPQ8Q09838A Γ00451 • W02004090140Α [00451 • EP04Q77624A Γ00451 • WQ20Q8133827Α [00451 • EP07002433W Γ0045] • ΕΡ1999283Α Γ00451 • WQ2Q071Q7328A Γ00451 • ΕΡ0571427Α [00461 • WQ9504826A Γ00461 • EPQ719338A [00481 • WQ9615248A Γ00481 • W09819581A [00461 • W09627874A [00461 • W09711188A Γ00461 • W09728382A Γ00461 • W09732985A [00461 • W09742328A [00461 • WQ9744472A [00461 • WQ9745545A ί00481 • W09827212A f00461 • WQ984Q5Q3A F0046] • W09958888A Γ00461 • WQ9958890A Γ00461 • W09958654A [00461 • WOOOQ8184A f00461 • WOQOQ8185A Γ00461 • WOQOQ8175A Γ00461 • W00028052A [00461 • WQ0077229A [00461 • WQ0112782Α [00481 • WOQ112828Α Γ00461 • WQQ21Q1Q59A [00461 • W003071880A [00481 • WQ2004058999A Γ00461 • WO20Q5Q3Q942A Γ00461 • W02005030941A Γ00481 • WO20Q5Q95632A Γ0046Ί • WQ2005095617A [00461 • W02005095619A Γ00481 • WQ2005095618A Γ00461 • WQ2005123927Α Γ00461 • W02008018319A Γ00461 • WQ20Q6103107Α [00481 • WQ2008108702Α Γ00461 • WQ2007009823A Γ0046] • W00022140A F0048] • W02008083862A Γ00461 • W02008072803A Γ0046] • WQ02034923A [00481 • EPQ8Q9Q134A [00461 • EPQ8Q9Q228A Γ00461 • EPQ8090227A [00481 • EPQ7Q9Q007A Γ00461 • EP07090QQ9A Γ00461 • WOQ114589Α [00461 • WQ0279410A [00461 • WQ0333540A Γ00461 • W02004078983A Γ00461 • WQQ119975Α F0046] • WO9528407A Γ00481 • WQ9634988A Γ00461 • WQ9820145A [00461 • WQ9912950A [00481 • W09968Q5QA Γ0046Ί • WO9953072A Γ00461 • US8734341B Γ00461 • WOOQ11192A [00461 • WQ9822804A [00461 • W09832326A ί00481 • WQ0198509A [00461 Γ00461 • WQ20Q50Q2359A [00481 • US5824790A [00461 • US8Q13881A Γ00481 • WO9404893A [00461 • WQ9409144A Γ00461 • W0941152QA Γ0046Ί • WO9535028A Γ00461 • WO9720938A [00461 • WQ1QQ12796A Γ0046] • W010003701Α Γ00461 • EP0883958A [00461 • WQ98Q19Q4A F0046] • WQ9621023A Γ00461 • WQ9839460A [00481 • WQ9924593A [00461 • WQ9531553A [00461 • US2002Q31828A [00461 • US8284479B Γ00461 • US57121Q7A [00461 • WQ9747808A [00481 • WO9747807A [00481 • WQ9747808A [00461 • WOQQ14249A F0046] • WQ0073422A Γ00461 [0046] • WQ0047727A [00481 • EP08Q77301A [00481 • US5908975A Γ00481 • EP0728213A [00481 • W02008032538A Γ00461 • W02007039314A Γ00481 • WO2Q07Q39315A Γ00461 • WQ2007Q33318A [00461 • JP2006304779B Γ00461 • WO20Q5Q12529A [00481 • US12020380B Γ00481 • US81054028B [00461 • W011095528A Γ00461 • WQ9800549A [00471 • WO20Q4Q53219A Γ00471 • WOQ117333A Γ00471 • WQ0245485A Γ00471 • WQ2Q05Q17157A Γ0047] • EPQ8075514A [00471 • US81128938F Γ0047Ί • WQ20Q8138351A [0047] • W011089021A [00471 • WQ2012074888A Γ00471 • US5989189A Γ0048Ί • US5840946A Γ00481 • US6323392B Γ00481 • US6063947A Γ00481 • US8270828B Γ00481 • US818919QB F00481 • US5985755A [00481 • W011080948A Γ00481 • US5434283A Γ00481 • US12888303B [00481 • WQ2012075426A Γ00481 • US81135230B Γ00491 • WQ09088313A Γ00491 • W010008732A Γ00491 • WQ2012090499A [00491 • WQ10121818A [00501 • WQ1Q145846A Γ0050] • WO2Q08128589A Γ00531 • WQ2008128570A f00531 • US2002120984A [00531 • WO20Q2Q34948A [00531 • WQ2010117737A Γ00531 • WQ2Q1Q117735A Γ00531 • WQ2005103268A Γ00531 [0053] • US2005216969A Γ0053] • US2007143876A ί0053Ί • W02008098952A Γ00531 • US200823Q473A Γ00531 • W02Q11Q75593A Γ00531 • WQ2011075595A Γ00531 • WQ2010077818A Γ0053Ί • US2008162007A Γ00531 • W02004053082A Γ00531 • US20Q3128834A Γ00531 • WQ2010080829Α Γ00531 • US2009217423A [00531 • WQ20Q8128573Α [00531 • US2010QQ24Q77A Γ0053] • WQ2008128571A Γ00531 • WQ2008128572Α Γ00531 • US2Q0813Q175A [00531 • WQ20Q4039988A [00531 • US2007067888A Γ00531 • WQ2005054479A Γ00531 • WQ2Q05Q54480A Γ00531 • WQ2011022469Α [00531 • US20Q8Q70139A [00531 • WQ20Q91Q0188A [00531 • WQ2011088384Α Γ00531 • WQ2011068380A Γ00531 • US2009137395A [00531 • WQ2QQ8112Q19A Γ00531 • US2008312082A [00531 • WO20Q8054747A [00531 • US20090210970Α [0053] • WQ2Q091Q3049A Γ00531 • US2Q100184079Α [0053Ί • W02008002872A [00531 • WO20Q7Q91277Α [00531 • US2006059581A ί0053Ί • υ520050887Ϊ9Α~ί00531^ ^ • US2005188434A [0053] [00531 • WQ2008151780Α [00531 • US2Q1Q050282A ί0053Ί • W02007017186Α Γ00531 • WQ2Q10078212Α [00531 • US20Q4172889A [00531 • W02004074492A [00531 • US2008Q84Q32A [00531 • WQ20Q8108874A [00531 • US2008320616A Γ00531 • WQ20061Q8875A [00531 • US2008196127A [0053] • W02003013224Α [00531 • US2003097687A [00531 • US8488747B [00531 • WQ2000028345A [00531 • US20082289060A [00531 • W02000028358A [00531 • US2007Q28322A [00531 • W02005081720Α Γ00531 • US2009300784A Γ00531 • WQ2Q07142840Α Γ00531 • US2008187458A [0053] • W02005103301Α Γ00531 • US20G4250317A [00531 • WQ2002100183Α Γ00531 • US2002102582A [00531 • W02004011801Α Γ00531 • US2008095988A [00531 • WQ2011082904Α [00531 • WQ2009111283Α [00531 • US2Q1101385Q4A [00531 • US20Q9130071A [00531 • W02009084852A Γ00531 • US2010QQ8Q887A [00531 • WQ2010037018Α [00531 • WQ2011Q347Q4A Γ00531 • WQ2010024976A Γ00531 • US2Q110067141A [00531 • WQ2009102873A Γ00531 • US2008028482A [00531 • WQ20Q5059103A [00531 • W02004072235A Γ00531 • US2006059590A [00531 • WQ2Q0714Q258A Γ00531 • US2008260932A [00531 • US2006282915A [00531 • WQ20Q6130436A [00531 • WQ2001031042A Γ00531 • WQ2001041558A Γ00531 [00531 • US2003188347A [00531 [00531 • US2007292854A [00531 • WQ20Q8114282A [00531 • W02002036831A Γ00531 • US2Q0807Q260A [00531 • WQ2Q0244407A [00531 • US2009265817A [00531 • US20Q1029014A [00531 • WQ20Q1051654A [00531 • US2010077501A [00531 • WQ20081224Q8A Γ00531 • WQ2006128568A [00531 • US2005039226A [00531 • WQ20Q4099447A [00531 • W02003052073A [00531 • WQ20111531SSA1 [00531 [00531 • W02Q11084621A Γ00531 • WQ2011063413A2 [00531 • WQ2011Q6636QA1 [00531 • WQ2011066384A1 [00531 • WQ2011075593A1 [00531 • W02Q11Q75595A1 [00531 • WQ2011084621A1 [00531 • WQ2011Q84632A1 [00531 • WQ2012033794A2 Γ00531 • WQ2012051199A2 [00531 • WQ2012075426A1 [00531 • WQ2012075429A1 [00531 • WQ2012082548A2 [00531 • WQ2012071Q39A1 Γ00531 • US2012131692A [00531 • WQ2012075426A2 [00531 • W02Q12075429A2 [00531 • WQ2009140769A [00821

Non-patent literature cited in the description • KEON et al.Current Genetics, 1991, vol. 19, 475-481 [00021 . COMAI et al.Science, 1983, vol. 221,370-371 [00401 • BARRY et al.Curr. Topics Plant Physiol., 1992, vol. 7, 139-145 [00401 . SHAH et al.Science, 1986, vol. 233, 478-481 [00401 . GASSER et al.J. Biol. Chern., 1988, vol. 263, 4280-4289 [00401 . TRANELWRIGHTScience, 2002, vol. 50, 700-712 [00411 • CRICKMORE et al.Microbiology and Molecular Biology Reviews, 1998, vol. 62, 807-813 [00421 . MOELLENBECK et al.Nat. Biotechnol., 2001, vol. 19, 668-72 [00421 • SCHNEPF etal.Applied Environm. Microbiol., 2006, vol. 71, 1765-1774 [00421 . J. Med. Chem., 2012, vol. 55, 1169-196 [00621 • Bioorg. Med. Chem., 2006, vol. 14, 8506-8518 [00621 . CRAMER et al.Analytical biochemistry, 1983, vol. 128, 384-392 [00761 • FRITZ et al.Agronomie, 1993, vol. 13, 225-230 Γ00761

Claims (8)

1. Fremgangsmåde til kurativ og/eller forebyggende behandling af planter mod mindst én stamme af svampe, der er resistente over for mindst ét SDHI (succinatdehydrogenasehæmmer)-fungicid, som omfatter påføring på planterne, på frøene, hvorfra de vokser, eller på lokaliteten, hvor de vokser, af en ikke-fytotoksisk, effektiv plantevækstfremmende mængde af en forbindelse med formel I

hvor T er et oxygen- eller et svovlatom, og X er valgt fra listen, der består af 2-isopropyl, 2-cyclopropyl, 2-tert-butyl, 5-chlor-2-ethyl, 5-chlor-2-isopropyl, 2-ethyl-5-fluor, 5-fluor-2-isopropyl, 2-cyclopropyl-5-fluor, 2-cyclopentyl-5-fluor, 2-fluor-6-isopropyl, 2-ethyl-5-methyl, 2-isopropyl-5-methyl, 2-cyclopropyl-5-methyl, 2-tert-butyl-5-methyl, 5-chlor-2-(trifluormethyl), 5-methyl-2-(trifluormethyl), 2- chlor-6-(trifluormethyl), 3-chlor-2-fluor-6-(trifluormethyl), 2-ethyl, 2-trimethylsilyl og 2-ethyl-4,5-dimethyl, eller et agrokemisk acceptabelt salt deraf.

2. Fremgangsmåde ifølge krav 1, hvor forbindelsen med formel (I) er valgt fra gruppen, der består af: N-cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropylbenzyl)-l-methyl-lH-pyrazol-4-carboxamid (forbindelse Al), N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid (forbindelse A2), N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid (forbindelse A3), N-(5-chlor-2-ethylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid (forbindelse A4), N- (5-chlor-2-isopropylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid (forbindelse A5), N-cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-fluorbenzyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid (forbindelse A6), N-cyclopropyl-3-(difluormethyl)-5-fluor-N-(5-fluor-2-isopropylbenzyl)-l-methyl-lH-pyrazol-4-carboxamid (forbindelse A7) , N-cyclopropyl-N-(2-cyclopropyl-5-fluorbenzyl)-3-(difluormethyl)-5-fluor-1-methyl-lH-pyrazol-4-carboxamid (forbindelse A8), N-(2-cyclopentyl-5-fluorbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-lH-pyrazol-4-carboxamid (forbindelse A9), N-cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-fluor-6-isopropylbenzyl)-l-methyl-lH-pyrazol-4-carboxamid (forbindelse A10) , N-cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid (forbindelse All), N-cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropyl-5-methylbenzyl)-l-methyl-lH-pyrazol-4-carboxamid (forbindelse A12) , N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluormethyl)-5-fluor-1-methyl-lH-pyrazol-4-carboxamid (forbindelse A13), N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-lH-pyrazol-4-carboxamid (forbindelse A14), N-[5-chlor-2-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-lH-pyrazol-4-carboxamid (forbindelse A15) , N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-N-[5-methyl-2-(trifluormethyl)benzyl]-lH-pyrazol-4-carboxamid (forbindelse A16) , N-[2-chlor-6-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-lH-pyrazol-4-carboxamid (forbindelse A17), N-[3-chlor-2-fluor-6-(trifluormethyl) benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-lH-pyrazol-4-carboxamid (forbindelse A18). N-cyclopropyl-3-(difluormethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluor-1-methyl-lH-pyrazol-4-carboxamid (forbindelse A19), N-cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropylbenzyl)-l-methyl-lH-pyrazol-4-carbothioamid (forbindelse A20), N-cyclopropyl-3-(difluormethyl)-N-(2-ethylbenzyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid (forbindelse A21) og N-cyclopropyl-3-(difluormethyl)-5-fluor-l-methyl-N-[2-(trimethylsilyl)benzyl]-lH-pyrazol-4-carboxamid (forbindelse A22) .

3. Fremgangsmåde ifølge krav 1 eller 2, hvor SDHI-fungicidet tilhører en kemisk gruppe valgt fra listen, der består af phenylbenzamider, pyridinylethylbenzamid, furancarboxamider, oxathiincarboxamider, thiazolcarboxamider, pyrazolcarboxamider og pyridincarboxamider.

4. Fremgangsmåde ifølge krav 1 eller 2, hvor svampestammen er resistent over for mindst ét fungicid valgt fra listen, der består af benodanil, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxan, trifluzamid, benzovindiflupyr, isofetamid.

5. Fremgangsmåde ifølge krav 1 eller 2, hvor stammen af svampe, der er resistent over for SDHI-fungicider, er valgt fra listen, der består af Ustilago maydis, Mycosphaerella graminicola, Aspergillus oryzae, Botrytis cinerea, Botrytis elliptica, Alternaria alternata, Corynespora cassiicola, Didymella bryoniae, Podosphaera xanthii, Sclerotinia sclerotiorum og Stemphylium botryose.

6. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 5, hvor forbindelsen med formel (I) påføres planterne eller lokaliteten, hvor de vokser, ved en påføringsmængde fra 0,005 til 0,5 kg/ha af forbindelsen med formel (I).

7. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 5, hvor forbindelsen med formel (I) anvendes som frøbehandling ved en anvendelsesmængde fra 0,001 til 250 g/kg frø.

8. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 5, hvor planterne er valgt fra gruppen, der består af bemuld, vin, majs, sojabønne, raps, solsikke, græstørv, gartneriafgrøder, buske, frugttræer, frugtplanter, grøntsager.