slide 1

Back to the List of the Granted Patents                                      Click here to download KE000286 PDF

(11) Patent Number: KE 286 (45) Date of grant: 12/01/2009
 
(12) PATENT
 
(51) Int.C1.7:
A 01N 43/40
(21)    Application Number: 2006/ 000390
(22)    Filing Date:
10/08/2006 (10/02/2005)
(30) Priority data:
04356014.3 12/02/2004 EP and 60/636,956 17/12/2004 US
 
(73)    Owner:
BAYER CROPSCIENCE SA of , 16 rue Jean-Marie Leclair, F¬69009 Lyon., France
(72) Inventor:
GOUOT, Jean-Marie and GROJEAN COURNOYER, Marie-Clair
(74)    Agent/address for correspondence: Kaplan & Stratton Advocates, P.O. Box 40111-00100, Nairobi (85) PCT data:
WO 2005 077183 Al 25/08/2005
 

 
(54) Title:
FUNGICIDAL COMPSITION COMPRISING A PYRIDYLETHYLBENZAMIDE DERIVATIVE AND A COMPOUND CAPABLE OF INHIBITING THE ERGOSTEROL BIOSYNTHESIS
(57) Abstract:
A composition comprising at least a pyridylethylbenzamide derivative of general formula (1) (a) and a compound capable of nhibiting the ergosterol biosynthesis (b) in a (a)/(b) weight ratio of from 0.01 to 20. A composition further comprising an additional fungicidal compound. A method of preventively or curatively combating the phytopathogenic fungi of crops by using this composition.
 
Fungicidal composition comprising a pyridylethylbenzamide derivative and a
compound capable of inhibiting the ergosterol biosynthesis
The present invention relates to novel fungicide compositions comprising a
5 pyridylethylbenzamide derivative and a compound capable of inhibiting the ergosterol biosynthesis. The present invention also relates to a method of combating or controlling phytopathogenic fungi by applying at a locus infested or liable to be infested such a composition.
10    International patent application WO 01/11965 generically discloses numerous
pyridylethylbenzamide derivatives. The possibility of combining one or more of these numerous pyridylethylbenzamide derivatives with known fungicidal products to develop a fungicidal activity is disclosed in general terms, without any specific example or biological data.
15    It is always of high-interest in agriculture to use novel pesticidal mixtures
showing a synergistic effect in order notably to avoid or to control the development of resistant strains to the active ingredients or to the mixtures of known active ingredients used by the farmer while minimising the doses of chemical products spread in the environment and reducing the cost of the treatment.
20    We have now found some novel fungicidal compositions which possess the
above mentioned characteristics.
Accordingly, the present invention relates to a composition comprising : a) a pyridylethylbenzamide derivative of general formula (I)
(X)P,.\(,         (Y)q    (I)

25    in which :
- p is an integer equal to 1, 2, 3 or 4;
- q is an integer equal to 1, 2, 3, 4 or 5;
- each substituent X is chosen, independently of the others, as being halogen, alkyl or haloalkyl;
30    - each substituent Y is chosen, independently of the others, as being halogen, alkyl,
alkenyl, alkynyl, haloalkyl, alkoxy, amino, phenoxy, alkylthio, dialkylamino, acyl,
 
2
cyano, ester, hydroxy, aminoalkyl, benzyl, haloalkoxy, halosulphonyl, halothioalkyl, alkoxyalkenyl, alkylsuiphonamide, nitro, alkylsuiphonyl, phenylsulphonyl or benzylsulphonyl;
as to the N-oxides of 2-pyridine thereof;
5 and
b) a compound capable of inhibiting the ergosterol biosynthesis;
in a (a) / (b) weight ratio of from 0.01 to 20.
In the context of the present invention :
10 - halogen means chlorine, bromine, iodine or fluorine;
- each of the alkyl or acyl radicals present in the molecule contains from 1 to 10 carbon atoms, preferably from 1 to 7 carbon atoms, more preferably from 1 to 5 carbon atoms, and may be linear or branched;
- each of the alkenyl or allcynyl radicals present in the molecule contains from 2 to 10 15 carbon atoms, preferably from 2 to 7 carbon atoms, more preferably from 2 to 5 carbon atoms, and may be linear or branched.
The composition according to the present invention provides a synergistic effect. This synergistic effect allows a reduction of the chemical substances spread
20 into the environment and a reduction of the cost of the fungal treatment.
In the context of the present invention, the term "synergistic effect" is defined by Colby according to the article entitled "Calculation of the synergistic and antagonistic responses of herbicide combinations" Weeds, (1967), 15, pages 20-22.
The latter article mentions the formula:
25    E = x + y —x* y
100
in which E represents the expected percentage of inhibition of the disease for the combination of the two fungicides at defined doses (for example equal to x and y respectively), x is the percentage of inhibition observed for the disease by the compound (I) at a defined dose (equal to x), y is the percentage of inhibition
30 observed for the disease by the compound (II) at a defined dose (equal to y). When the percentage of inhibition observed for the combination is greater than E, there is a synergistic effect.
The composition according to the present invention comprises a 35 pyridylethylbenzamide derivative of general formula (I). Preferably, the present
 
3
invention relates to a composition comprising a pyridylethylbenzamide derivative of general formula (I) in which the different characteristics may be chosen alone or in combination as being :
- as regards p, p is 2;
5    - as regards q, q is 1 or 2. More preferably, q is 2;
- as regards X, X is chosen, independently of the others, as being halogen or haloalkyl. More preferably, X is chosen, independently of the others, as being a chloro atom or a trifluoromethyl group;
- as regards Y, Y is chosen, independently of the others, as being halogen or 10    haloalkyl. More preferably, Y is chosen, independently of the others, as being a
chloro atom or a trifluoromethyl group;
More preferably, the pyridylethylbenzamide derivative of general formula (I) present in the composition of the present invention is :
- N-{243-chloro-5-(trifluoromethyl)-2-pyridinylJethyl -2 -trifl uoromethylbenzamide 15 (compound 1);
- N-{243-chloro-5-(trifluoromethyl)-2-pyridinylJethyl } -2 -i odobenzamide (compound 2); or
- N- { 243,5 -dichloro-2-pyrid nyl] ethyl } -2 -tri fl uoromethylbenzamide (compound 3).
Even more preferably, the pyridylethylbenzamide derivative of general
20        formula (I) present in the composition of the present invention is N- (2-13-chloro-5-
(trifluoromethyl)-2-pyridinyllethyl)-2-trifluoromethylbenzamide (compound 1).
The composition according to the present invention comprises a compound capable of inhibiting the ergosterol biosynthesis. Preferably, the present invention
25 relates to a composition comprising a compound capable of inhibiting the ergosterol biosynthesis selected from triazole derivatives, imidazole derivatives, morpholine derivatives, piperidine derivatives, fenhexamid, spiroxamine or triforine. Spiroxamine, triforine and fenhexamid are preferred.
. Triazole derivatives are also preferred. According to the present invention,
30 triazole derivatives may for example be azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole,
35    diclobutrazole, etaconazole, fluotrimazole, furconazole, furconazole-cis, triamiphos,
 
4
triazbutil. Cyproconazole, fluquinconazole, prothioconazole and tebuconazole are still preferred.
Imidazole derivatives are also preferred. According to the present invention, imidazole derivatives may for example be imazalil, prochloraz, oxpoconazole 5 fumarate, pefurazoate or triflumizole. Prochloraz is still preferred.
Morpholine derivatives are also preferred. According to the present invention, morpholine derivatives may for example be aldimorph, dodemorph, fenpropimorph or tridemorph. Fenpropimorph and tridemorph are still preferred.
Piperidine derivatives are also preferred. According to the present invention, 10 piperidine derivatives may for example be fenpropidin or piperalin.
The composition according to the present invention comprises at least a pyridylethylbenzamide derivative of general formula (I) (a) and a compound capable of inhibiting the ergosterol biosynthesis (b) in an (a) / (b) weight ratio of from 0.01 to
15 20; preferably of from 0.05 to 10; even more preferably, of from 0.1 to 5.
The composition of the present invention may further comprise at least one other different fungicide active ingredient (c).
The fungicidal active ingredient (c) may be selected from azaconazole,
20 azoxystrobin, (Z)-N[a-(cyclopropylmethoxyimino)-2,3-difluoro-6- (trifluoromethypbenzy11-2-phenylacetamide, 6-iodo-2-propoxy-3-propyl quinazolin¬4(311)-one, benalaxyl, benomyl, benthiavalicarb, biphenyl, bitertanol, blasticidin-S, boscalid, borax, bromuconazole, bupirimate, sec-butylamine, calcium polysulfide, captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat,
25 chlorothalonil, chlozolinate, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, cuprous oxide, cyazofamid, cymoxanil, cyproconazole, cyprodinil, dammet, debacarb, dichlofluanid, dichlorophen, diclobutrazole, diclocymet, diclomezine, dicloran, diethofencarb, difenoconazole, difenzoquat metilsulfate, difenzoquat, diflumetorim, dimethirimol, dimethomorph, diniconazole,
30 dinobuton, dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine, edifenphos, epoxiconazole, etaconazole, ethaboxam, ethirimol, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenpiclonil, fenoxanil, fenpropidin, fenpropimorph, fentin, fentin hydroxide, fentin acetate, ferbam, ferimzone, fluazinam, fludioxonil, fluoroimide,
35        fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet,
formaldehyde, fosetyl, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr,
 
5
guazatine, guazatine acetates, hexachlorobenzene, hexaconazole, 8-hydroxyquinoline sulfate, potassium hydroxyquinoline sulfate, hymexazol, imazalil sulfate, imazalil, imibenconazole, iminoctadine, iminoctadine triacetate, ipconazole, iprobenfos, iprodione, iprovalicarb, isoprothiolane, kasugamycin, kasugamycin hydrochloride
5 hydrate, kresoxim-methyl, mancopper, mancozeb, maneb, mepanipyrim, mepronil, mercuric chloride, mercuric oxide, mercurous chloride, metalaxyl, metalaxyl-M, metam-sodium, metam, metconazole, methasulfocarb, methyl isothiocyanate, metiram, metominostrobin, mildiomycin, myclobutanil, . nabam, nickel bis(dimethyldithiocarbamate), nitrothal-isopropyl, nuarimol, octhilinone, ofurace,
10    oleic acid, oxadixyl, oxine-copper, oxpoconazole furnarate, oxycarboxin,
pefurazoate, penconazole, pencycuron, pentachlorophenol, sodium pentachlorophenoxide, pentachlorophenyl laurate, phenylmercury acetate, sodium 2- phenylphenoxide, 2-phenylphenol, phosphorous acid, phthalide, picoxystrobin, piperalin, polyoxinspolyoxin B, polyoxin, polyoxorim, probenazole, prochloraz,
15 procymidone, propamocarb hydrochloride, propamocarb, propiconazole, propineb, prothioconazole, pyraclostrobin, pyrazophos, pyributicarb, pyrifenox, pyrimethanil, pyroquilon, quinoxyfen, quintozene, silthiofam, simeconazole, spiroxamine, sulfur, tar oils, tebuconazole, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,
20  triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, vinclozolin, zineb, ziram and zoxamide.
Preferably, fungicidal active ingredient (c) is selected from trifloxystrobin, fluoxastrobin, pyrimethanil, thiabendazole, guazatine, imidoctadine, picoxystrobin, pyraclostrobin, azoxystrobin, dimoxystrobin, metaminostrobin, 2-{2-[6-(3-chloro-2-
25 methylphenoxy)-5-fl uoro-pyrimidin-4-yloxy] -phenyl ) 2 -methoxyimino-N-methylacetam ide, captane, dodine, propineb, mancozeb, spiroxamine, prothioconazole, tebuconazole, thirame, tolylfluanid, iminoctadine, dithianon, sulphur, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, dinocap, quinoxyfen, 2-butoxy-6-iodo-3-propyl-benzopyran-4-one, fludioxonil,
30    triazoxide, fosetyl-Al and phosphorous acid.
Where the third active ingredient (c) as defined above is present in the composition, this compound may be present in an amount of (a) : (b) : (c) weight ratio of from 1 : 0.01 : 0.01 to 1 : 20 : 20; the ratios of compound (a) and compound
35        (c) varying independently from each other. Preferably, the (a) : (b) : (c) weight ratio
may be of from 1 : 0.05 : 0.05 to 1 : 10 : 10.
 
6
Following compositions may be cited to illustrate in a non-limited manner the present invention : compound 1 with fenhexatnid, compound 1 with spiroxamine, compound 1 with triforine, compound 1 with azaconazole, compound 1 with
5 bitertanol, compound 1 with bromuconazole, compound 1 with cyproconazole, compound 1 with difenoconazole, compound I with diniconazole, compound 1 with epoxiconazole, compound 1 with fenbuconazole, compound I with fluquinconazole, compound 1 with flusilazole, compound I with flutriafol, compound 1 with hexaconazole, compound 1 with imibenconazole, compound I with ipconazole,
10 compound 1 with metconazole, compound 1 with myclobutanil, compound I with penconazole, compound I with propiconazole, compound 1 with prothioconazole, compound 1 with simeconazole, compound I with tebuconazole, compound 1 with tetraconazole, compound 1 with triadimefon, compound 1 with triadimenol, compound I with triticonazole, compound I with diclobutrazote, compound I with
15 etaconazole, compound 1 with fluotrimazole, compound 1 with furconazole, compound I with furconazole-cis, compound 1 with triamiphos, compound t with triazbutil, compound I with imazalil, compound I with prochloraz, compound 1 with oxpoconazole fumarate, compound I with pefurazoate, compound 1 with triflumizole, compound 1 with aldimorph, compound 1 with dodemorph, compound
20 I with fenpropimorph, compound 1 with tridemorph, compound I with fenpropidin, compound 1 with piperalin, compound 2 with fenhexamid, compound 2 with spiroxamine, compound 2 with triforine, compound 2 with azaconazole, compound 2 with bitertanol, compound 2 with bromuconazole, compound 2 with cyproconazole, compound 2 with difenoconazole, compound 2 with diniconazole, compound 2 with
25 epoxiconazole, compound 2 with fenbuconazole, compound 2 with fluquinconazole, compound 2 with flusilazole, compound 2 with flutriafol, compound 2 with hexaconazole, compound 2 with imibenconazole, compound 2 with ipconazole, compound 2 with metconazole, compound 2 with myclobutanil, compound 2 with penconazole, compound 2 with propiconazole, compound 2 with prothioconazole,
30 compound 2 withsimeconazole, compound 2 with tebuconazole, compound 2 with tetraconazole, compound 2 with triadimefon, compound 2 with triadimenol, compound 2 with triticonazole, compound 2 with diclobutrazole, compound 2 with etaconazole, compound 2 with fluotrimazole, compound 2 with furconazole, compound 2 with furconazole-cis, compound 2 with triamiphos, compound 2 with
35 triazbutil, compound 2 with ima7alil, compound 2 with prochloraz, compound 2 with oxpoconazole fumarate, compound 2 with pefurazoate, compound 2 with
 
7
triflumizole, compound 2 with aldimorph, compound 2 with dodemorph, compound 2 with fenpropimorph, compound 2 with tridemorph, compound 2 with fenpropidin, compound 2 with piperalin, compound 3 with fenhexamid, compound 3 with spiroxamine, compound 3 with triforine, compound 3 with azaconazole, compound 3
5 with bitertanol, compound 3 with bromuconazole, compound 3 with cyproconazole, compound 3 with difenoconazole, compound 3 with diniconazole, compound 3 with epoxiconazole, compound 3 with fenbuconazole, compound 3 with fluquinconazole, compound 3 with flusilazole, compound 3 with flutriafol, compound 3 with hexaconazole, compound 3 with imibenconazole, compound 3 with ipconazole,
10 compound 3 with metconazole, compound 3 with myclobutanil, compound 3 with periconazole, compound 3 with propiconazole, compound 3 with prothioconazole, compound 3 withsimeconazole, compound 3 with tebuconazole, compound 3 with tetraconazole, compound 3 with triadimefon, compound 3 with triadimenol, compound 3 with triticonazole, compound 3 with diclobutrazole, compound 3 with
15 etaconazole, compound 3 with fluotrimazole, compound 3 with furconazole, compound 3 with fiirconazole-cis, compound 3 with triamiphos, compound 3 with triazbutil, compound 3 with imazalil, compound 3 with prochloraz, compound 3 with oxpoconazole fumarate, compound 3 with pefurazoate, compound 3 with triflumizole, compound 3 with aldimorph, compound 3 with dodemorph, compound
20 3 with fenpropimorph, compound 3 with tridemorph, compound 3 with fenpropidin, compound 3 with piperalin.
The composition according to the present invention may further comprise an other additional component such as an agriculturally acceptable support, carrier or 25    filler.
In the present specification, the term "support" denotes a natural or synthetic, organic or inorganic material with which the active material is combined to make it easier to apply, notably to the parts of the plant. This support is thus generally inert and should be agriculturally acceptable. The support may be a solid or a liquid.
30 Examples of suitable supports include clays, natural or synthetic silicates, silica, resins, waxes, solid fertilisers, water, alcohols, in particular butanol, organic solvents, mineral and plant oils and derivatives thereof. Mixtures of such supports may also be used.
The composition may also comprise other additional components. In
35 particular, the composition may further comprise a surfactant. The surfactant can be
an emulsifier, a dispersing agent or a wetting agent of ionic or non-ionic type or a
 
8
mixture of such surfactants. Mention may be made, for example, of polyacrylic acid salts, lignosulphonic acid salts, phenolsulphonic or naphthalenesulphonic acid salts, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amities, substituted phenols (in particular alkylphenols or arylphenols), salts of
5  sulphosuccinic acid esters, taurine derivatives (in particular alkyl taurates), phosphoric esters of polyoxyethylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the above compounds containing sulphate, sulphonate and phosphate functions. The presence of at least one surfactant is generally essential when the active material and/or the inert support are water-insoluble and when the
10 vector agent for the application is water. Preferably, surfactant content may be comprised between 5% and 40% by weight of the composition.
Additional components may also be included, e.g. protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilisers, sequestering agents. More generally, the active materials can be combined with any solid or liquid
15 additive, which complies with the usual formulation techniques.
In general, the composition according to the invention may contain from 0.05 to 99% (by weight) of active material, preferably 10 to 70% by weight.
Compositions according to the present invention can be used in various forms such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable
20 powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate. for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment,
25  seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra low volume (ulv) liquid, ultra low volume (ulv) suspension, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder.
30    These compositions include not only compositions which are ready to be
applied to the plant or seed to be treated by means of a suitable device, such as a spraying or dusting device, but also concentrated commercial compositions which must be diluted before they are applied to the crop.
35    The fungicidal compositions of the present invention can be used to curatively
or preventively control phytopathogenic fungi of crops. Thus, according to a further
 
9
aspect of the present invention, there is provided a method for preventively or curatively controlling phytopathogenic fungi of crops characterised in that a fungicidal composition as hereinbefore defined is applied to the seed, the plant and/or to the fruit of the plant or to the soil in which the plant is growing or in which it is desired to grow.
5  The composition as used against phytopathogenic fungi of crops comprises an effective and non-phytotoxic amount of an active material of general formula (I).
The expression "effective and non-phytotoxic amount" means an amount of composition according to the invention which is sufficient to control or destroy the fungi present or liable to appear on the crops, and which does not entail any appreciable
10 symptom of phytotoxicity for the said crops. Such an amount can vary within a wide range depending on the fungus to be combated or controlled, the type of crop, the climatic conditions and the compounds inchAded in the fungicidal composition according to the invention.
This amount can be determined by systematic field trials, which are within the 15 capabilities of a person skilled in the art.
The method of treatment according to the present invention is useful to treat propagation material such as tubers or rhizomes, but also seeds, seedlings or seedlings pricking out and plants or plants pricking out. This method of treatment can also be useful to treat roots. The method of treatment according to the present
20 invention can also be useful to treat the overground parts of the plant such as trunks, stems or stalks, leaves, flowers and fruits of the concerned plant.
Among the plants that can be protected by the method according to the
invention, mention may be made of cotton; flax; vine; fruit crops such as Rosaceae
sp. (for instance pip fruits such as apples and pears, but also stone fruits such as
25 apricots, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp.,
Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp.,
Lauraceae sp., Musaceae sp. (for instance banana trees and plantins), Rubiaceae sp.,
Theaceae sp., Sterculiceae sp., Rutaceae sp. (for instance lemons, oranges and
grapefruits); leguminous crops such as Solanaceae sp. (for instance tomatoes),
30 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); big crops such as Graminae sp. (for
instance maize, cereals such as wheat, rice, barley and triticale), Asteraceae sp. (for
instance sunflower), Cruciferae sp. (for instance colza), Papilionaceae sp. (for
35 instance soja), Solanaceae sp. (for instance potatoes), Chenopodiaceae sp. (for
 
10
instance beetroots); horticultural and forest crops; as well as genetically modified homologues of these crops.
Among the plants and the possible diseases of these plants protected by the method according to the present invention, mention may be made of :
5    - wheat, as regards controlling the following seed diseases: fusaria
(Microdochium nivale and Fusarium roseum), stinking smut (Tilletia chries, Tilletia controversa or Tilletia indica), septoria disease (Septoria nodorum) and loose smut;
- wheat, as regards controlling the following diseases of the aerial parts of the plant: cereal eyespot (Tapesia yallundae, Tapesia acuiformis), take-all
10 (Oaeumannomyces graminis), foot blight (F. culmorum, F. graminearum), black speck (Rhizoctonia cerealis), powdery mildew (Erysiphe graminis forma specie tritici), rusts (Puccinia striiformis and Puccinia recondita) and septoria diseases (Septoria tritici and Septoria nodorum);
- wheat and barley, as regards controlling bacterial and viral diseases, for 15 example barley yellow mosaic;
- barley, as regards controlling the following seed diseases: net blotch (Pyrenophora graminea, Pyrenophora teres and Cochliobolus sativus), loose smut (Ustilago nuda) and fusaria (Microdochium nivale and Fusarium roseum);
- barley, as regards controlling the following diseases of the aerial parts of the
20 plant: cereal eyespot (Tapesia yallundae), net blotch (Pyrenophora teres and Cochliobolus sativus), powdery mildew (Erysiphe graminis forma specie hordei), dwarf leaf rust (Puccinia hordei) and leaf blotch (Rhynchosporium secalis);
- potato, as regards controlling tuber diseases (in particular Helminthosporium solani, Phoma tuberosa, Rhizoctonia solani, Fusarium solani), mildew (Phytopthora
25    infestans) and certain viruses (virus Y);
- potato, as regards controlling the following foliage diseases: early blight (Alternaria solani), mildew (Phytophthora infestans);
- cotton, as regards controlling the following diseases of young plants grown from seeds: damping-off and collar rot (Rhizoctonia solani, Fusarium oxysporum) and 30 black root rot (Thielaviopsis basicola);
- protein yielding crops, for example peas, as regards controlling the following seed diseases: anthracnose (Ascochyta pisi, Mycosphaerella pinodes), fusaria (Fusarium oxysporum), grey mould (Botrytis cinerea) and mildew (Peronospora pisi);
35    - oil-bearing crops, for example rape, as regards controlling the following
seed diseases: Phoma lingam, Alternaria brassicae and Sclerotinia sclerotiorum;
 
1I
- corn, as regards controlling seed diseases: (Rhizopus sp., Penicillium sp., Trichoderma sp., Aspergillus sp., and Gibberella fujikuroi);
- flax, as regards controlling the seed disease: Alternaria linicola;
-    forest trees, as regards controlling damping-off (Fusarium oxysporum, 5 Rhizoctonia solani);
- rice, as regards controlling the following diseases of the aerial parts: blast disease (Magnaporthe grisea), bordered sheath spot (Rhizoctonia solani);
-    leguminous crops, as regards controlling the following diseases of seeds or of young plants grown from seeds: damping-off and collar rot (Fusarium oxysporum, 10 Fusarium roseum, Rhizoctonia solani, Pythium sp.);
- leguminous crops, as regards controlling the following diseases of the aerial parts: grey mould (Botrytis sp.), powdery mildews (in particular Erysiphe cichoracearum, Sphaerotheca fuliginea and Leveillula taurica), fusaria (Fusarium oxysporum, Fusarium roseum), leaf spot (Cladosporium sp.), alternaria leaf spot
15 (Alternaria sp.), anthracnose (Colletotrichum sp.), septoria leaf spot (Septoria sp.), black speck (Rhizoctonia solani), mildews (for example Bremia lactucae, Peronospora sp., Pseudoperonospora sp., Phytophthora sp.);
- fruit trees, as regards diseases of the aerial parts: monilia disease (Monilia fructigenae, M laxa), scab (Venturia inaequalis), powdery mildew (Podosphaera 20 leucotricha);
- vine, as regards diseases of the foliage: in particular grey mould (Botrytis cinerea), powdery mildew (Uncinula necator), black rot (Guignardia biwelli) and mildew (Plasmopara viticola);
- beetroot, as regards the following diseases of the aerial parts: cercospora 25 blight (Cercospora beticola), powdery mildew (Erysiphe beticola), leaf spot (Ramularia beticola).
The fungicidal composition according to the present invention may also be used against fungal diseases liable to grow on or inside timber. The term "timber"
30 means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood. The method for treating timber according to the invention mainly consists in contacting one or more compounds of the present invention, or a composition according to the invention; this includes for example direct application, spraying,
35 dipping, injection or any other suitable means.
 
12
The fungicidal composition according to the present invention may also be used in the treatment of genetically modified organisms with the compounds according to the invention or the agrochemical compositions according to the invention. Genetically modified plants are plants into in which genome a
5 heterologous gene encoding a protein of interest has been stably integrated. The expression "heterologous gene encoding a protein of interest" essentially means genes which give the transformed plant new agronomic properties, or genes for improving the agronomic quality of the transformed plant.
10    The dose of active material usually applied in the treatment according to the
present invention is generally and advantageously between 10 and 2000 g/ha, preferably between 20 and 1500 g(ha for applications in foliar treatment. The dose of active substance applied is generally and advantageously between 1 and 200 g per 100 kg of seed, preferably between 2 and 150 g per 100 kg of seed in the case of seed
15 treatment. It is clearly understood that the doses indicated above are given as illustrative examples of the invention. A person skilled in the art will know how to adapt the application doses according to the nature of the crop to be treated.
The compositions according to the present invention may also be used fore
20 the preparation of composition useful to curatively or preventively treat human and animal fungal diseases such as, for example, mycoses, dermatoses, trichophyton diseases and candidiases or diseases caused by Aspergillus spp. or Candida spp., for example Aspergillus fumigatus or Candida albicans respectively.
25    The present invention will now be illustrated with the following example :
Example 1 : Efficacy against Mycosphaerella rraminicola of a mixture containing N-{2-13-chloro-5-(trifluoromethyl)-2-pyridinyllethyll-2.- ttifluoromethylbenzamide (Compound 1) and tebuconazole
30
The active ingredients tested are prepared by potter homogenisation in a mixture of acetone/tween/water . This suspension is then diluted with water to obtain the desired active material concentration.
Wheat plants (Scipion variety), sown on a 50/50 peat soil-pozzolana substrate 35    in starter cups and grown at 12°C, are treated at the 1-leaf stage (10 cm tall) by
 
13
spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material.
After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Mycosphaerella graminicola spores (500 000 spores per m1). The
5 spores are collected from a 7-day-old culture .The contaminated wheat plants are incubated for 72 hours at 18°C and at 100% relative humidity, and then for 21 to 28 days at 90% relative humidity.
Grading (% of efficacy) is carried out 21 to 28 days after the contamination, in comparison with the control plants.
10
The following table summarises the results obtained when tested compound 1 and tebuconazole alone and in a 1/1 weight ratio mixture.
    Dose
(Oa)    % Efficacy    Synergism
(Colby)
-
Compound 1    15    25   
    31    65    -
Tebuconazole    15    15    -
    31     15    -
Compound 1 + tebuconazole
(Ratio 111)    15+15    75    +39
    31+31    80    +10

15    According to the Colby method, a synergistic effect of the mixtures tested has
been observed.
Example 2 : Efficacy against Erysiphe graminis f. sp. graminis of a mixture containing    N-{2-13-chloro-5-(trifluoromethyl)-2-pyrid inyllethyl)-2-
20 trifluoromethy1benzamide (Compound 1) and prothioconazole
The active ingredients tested are prepared by potter homogenisation in a mixture of acetone/tween/water . This suspension is then diluted with water to obtain the desired active material concentration.
25    Wheat plants (Audace variety) in starter cups, sown on 50/50 peat
soil-pozzolana substrate and grown at 12°C, are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above.
 
14
Plants, used as controls, are treated with an aqueous solution not containing the active material.
After 24 hours, the plants are contaminated by dusting them with Erysiphe
graminis f. sp. tritici spores, the dusting being carried out using diseased plants.
5        Grading is carried out 7 to 14 days after the contamination, in comparison
with the control plants.
The following table summarises the results obtained when tested compound 1 and pmthioconazole alone and in a 1/2 weight ratio mixture.
10
    Dose
(g/ha)    % Efcacyfi    Synergism
(Colby)
Compound 1    125    20    -
    62,5    0    -
Prothioconazote    250    60    -
    125    0    -
Compound 1 + prothioconazole
- (Ratio 1/2)    125 + 250    85    +17
    62 + 125    70    +70

According to the Colby method, a synergistic effect of the mixtures tested has been observed.
15 Example 3 : Efficacy against Botrytis cinerea of a mixture containing N-1243- chloro-5-(t rifluoromethyl)-2-ny ridinyll etbv11-2-trifluoromethylbenzamide (Compound 1) and propiconazole
The active ingredients tested are prepared by potter homogenisation in a 20 mixture of acetone/tweenJwater This suspension is then diluted with water to obtain the desired active material concentration.
Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 18-20°C, are treated at the cotyledon Z11 stage by spraying with the aqueous suspension described above. Plants, used as
25 controls, are treated with an aqueous solution not containing the active material.
After 24 hours, the plants are contaminated by depositing drops of an aqueous suspension of Botrytis cinerea spores (150,000 spores per ml) on upper surface of the
 
15
leaves. The spores are collected from a 15-day-old culture and are suspended in a nutrient solution composed of :
- 20 g/L of gelatine
- 50 g/L of cane sugar
5    - 2 g/L of NH4NO3
-1 g/L of KH2PO4
The contaminated gherkin plants are settled for 5/7 days in a climatic room at
15-11°C (day/night) and at 80% relative humidity. Grading (% of efficacy) is carried
out 5 to 7 days after the contamination, in comparison with the control plants.
10
The following table summarises the results obtained when tested compound 1 and propiconazole alone and in different weight, ratio mixtures.
    Dose
(ppm)    % Efficacy    Synergism
(Colby)
-
Compound 1    12    0   
    37    30    -
    111    80   
Propiconazole    37    30    -
    111    50    -
    333    70    -
Compound 1 4- propiconazole
(Ratio 1/9)    37 + 333    100    21
    12 + 111    100    50
Compound 1 + propiconazole
(Ratio 1/3)    37 +111    100    + 35
Compound 1 + propiconazole
(Ratio 1/1)    37 + 37    80    + 29

15    According to the Colby method, a synergistic effect of the mixtures tested has
been observed.
 
16
Example 4 : Efficacy aaainst Ervsiphe fframinis f. so. zraminis of a mixture containina N42-13-ehloro-5-(trifluoromethvi)-2-pyridinyllethvII-2- trifluoromethylbenzanaide (Compound I) and cyproconazole
5    The formulated {concentrated suspension) compounds are diluted with water
to obtain the desired active material concentration Wheat plants (Audace variety) in starter cups, sown on 50/50 peat soil-pozzolona substrate and grown at I 2'C, are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above.
10    Plants, used as controls, are treated with an aqueous solution not containing
the active material.
After 24 hours, the plants are contaminated by dusting them with Ery_ ha
graminis f. sp. Wild spores, the dusting being carried out using diseased plants. Grading is carried out 7 to 14 days after the contamination, in comparison
15    with the control plants.
The following table summarises the results obtained when tested compound and cyproconazole alone and in a 2/1 weight ratio mixture.

    Dose
(g/ha)    % Efficacy    Synergism
(Colby)
Compound 1    62.5    10   
Cyproconazole    31.2    15    .
Compound I + cyproconazole
(Ratio 2/1)    62.5 +31 2    60    +37

20
According to the Colby method, a synergistic effect of the mixtures testa been observed.
 
17
Example 5 : Efficacy against &midis cinerea of a mixture containing N-42-13-
chloro-5-(trifluoromethvI)-2-pyridinyllethyll-2-trifluoromethylbenzamide Compound 11 and difenconazole
5    The active ingredients tested are prepared by potter homogenisation in a
mixture of acetone/tween/water . This suspension is then diluted with water to obtain the desired active material concentration.
Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 18-20°C, are treated at the cotyledon Z11
10 stage by spraying with the aqueous suspension described above. Plants, used as
controls, are treated with an aqueous solution not containing the active material.
After 24 hours, the plants are contaminated by depositing drops of an aqueous suspension of Botrytis cinerea spores (150,000 spores per ml) on upper surface of the leaves. The spores are collected from a 15-day-old culture and are suspended in a
15 nutrient solution composed of :
- 20 g/L of gelatine
- 50 g/L of cane sugar
- 2 g/L of N114NO3
- 1 g/L of KH2PO4
20    The contaminated gherkin plants are settled for 517 days in a climatic room at
15-11°C (day/night) and at 80% relative humidity. Grading (% of efficacy) is carried out 5 to 7 days after the contamination, in comparison with the control plants.
The following table summarises the results obtained when tested compound 1 25 and difenconazole alone and in different weight ratio mixtures.

    Dose
(PPm)    °A Efficacy    Synergism
(Colby)
Compound 1    37    0    -
    111    80    -
Difenconazole    1 1 I    15    -
    333    25    -
Compound 1 + difenconazole
(Ratio 1/3)    37 + 111    80    + 65
 
18

Compound 1+ difenconazole
(Ratio 1/1)    111+111    100    + 17
Compound 1 + difenconazole    (Ratio 1/9)
111+333    80    + 55

According to the Colby method, a synergistic effect of the mixtures tested has been observed.
5 Example 6 : Efficacy aitainst Botrytis cinerea of a mixture containinE N42-13-  chloro-5-(trifluoromethyl)-2-pyridinyllethyll-2-trifluoromethylbenzamide cCompound I) and hexaconazole
The active ingredients tested are prepared by potter homogenisation in a 10 mixture of acetone/tween/water . This suspension is then diluted with water to obtain the desired active material concentration.
Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 18-20°C, are treated at the cotyledon Z11 stage by-spraying with the aqueous suspension described above. Plants, used as
15    controls, are treated with an aqueous solution not containing the active material.
After 24 hours, the plants are contaminated by depositing drops of an aqueous suspension of Botrytis cinerea spores (150,000 spores per ml) on upper surface of the leaves. The spores are collected from a 15-day-old culture and are suspended in a nutrient solution composed of :
20    - 20 g/L of gelatine
- 50 g/L of cane sugar
- 2 g/L of NH4NO3
- 1 g/L of KH2PO4
The contaminated gherkin plants arc settled for 5/7 days in a climatic room at 25    15-11°C (day/night) and at 80% relative humidity. Grading (% of efficacy) is carried
out 5 to 7 days after the contamination, in comparison with the control plants.
The following table summarises the results obtained when tested compound 1 and hexaconazole alone and in a 1:27 weight ratio mixture.
 
19
    Dose
Win)    % Efficacy    Synergism
(Colby)
Compound 1    4    10    .    -
Hexaconazole    1 i 1    15    -
Compound 1 + hexaconazole
(Ratio I :27)    4 + 111    98    + 19

According to the Colby method, a synergistic effect of the mixtures tested has been observed.
Example 7 : Efficacy against Erysiphe Eraminis f. sp. Rraminis of a mixture containing N- f243-ch lo ro-5-(triflu oromethv11-2-pyrid inyll ethyll -2- trifluoromethvlbenzamide (Compound and metconazole
10    The formulated compounds are diluted with water to obtain the desired active
material concentration. Wheat plants (Audace variety) in starter cups, sown on 50150 peat soil-pozzolana substrate and grown at 12°C, are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above.
Plants, used as controls, are treated with an aqueous solution not containing 15    the active material.
After 24 hours, the plants are contaminated by dusting them with Erysiphe
graminis f. sp. hind spores, the dusting being carried out using diseased plants.
Grading is carried out 7 to 14 days after the contamination, in comparison with the control plants.
20
The following table summarises the results obtained when tested compound 1 and metconazole alone and in a 8:1 weight ratio mixture.

    Dose
(tea)    % Efficacy    Synergism
(Colby)
Compound 1    250    40    -
Metconazole    31.2    50   
Compound 1 + metconazole
(Ratio 8:1)    250 + 31.2    80    + I 0
 
20
According to the Colby method, a synergistic effect of the mixtures tested has been observed.
5 Example 8 : Efficacy against Puccinia recanditu of a mixture containing N-12- 3-chloro-5- frifluormneth I -2-    -2-trifluorometh Mecum'
(Compound 1) and epoxiconazole
The formulated compounds are diluted with water to obtain the desired active
10 material concentration Wheat plants (Scipion variety) in starter cups, sown on 50/50 peat soil-pozzolana substrate and grown at 12°C, are treated at the 1.-leaf stage (10 cm tall) by spraying with the aqueous suspension described above.
Plants, used as controls, are treated with an aqueous solution not containing the active material.
15    After 24 hours, the plants arc contaminated by spraying the leaves with an
aqueous suspension of Puccinia recondite spores (100,000 spores per ml). The spores are collected from a 10-day-old contaminated wheat and are suspended in water containing 2.5 m1/1 of tween 80 10%. The contaminated wheat plants are incubated for 24 hours at 20°C and at 100% relative humidity, and then for 10 days
20 at 20°C and at 70% relative humidity. Grading is carried out 10 days after the contamination, in comparison with the control plants.
The following table summarises the results obtained when tested compound 1 and epoxiconazole alone and in different weight ratio mixtures.
25
    Dose
(Oa)    % Efficacy    Synergism
(Colby)
-
Compound 1    62.5    0   
    250    0    .
Epoxiconazole     15.6    25    -
Compound I + epoxiconazole
(Ratio 16:1)    250 + 15.6    80    + 55
Compound 1 + epoxiconazole
(Ratio 4:1)    62.5 + 15.6    85    + 60
 
21
According to the Colby method, a synergistic effect of the mixtures tested has been observed
Example 9 : Efficacy against Botrvtis cinerea of a mixture containing N-(2-13¬5    chloro-5-(trifluoromethy11-2-pyridinyllethyff-2-trifluorom ethylbenzam ide
(Compound 1) and myclobutanil
The formulated compounds are diluted with water to obtain the desired active material concentration.
10    Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a 50/50
peat soil-pozzolana substrate and grown at 18-20°C, are treated at the cotyledon Z11 stage by spraying with the aqueous suspension, described above. Plants, used as controls, are treated with an aqueous solution not containing the active material.
After 24 hours, the plants are contaminated by depositing drops of an aqueous
15 suspension of Botrytis cinerea spores (150,000 spores per ml) on upper surface of the leaves. The spores are collected from a 15-day-old culture and are suspended in a nutrient solution composed of :
- 20 g/L of gelatine
- 50 g/L of cane sugar
20    - 2 g/L of NH4NO3
- 1 g/L of KH2PO4
The contaminated gherkin plants are settled for 5/7 days in a climatic room at 15-11°C (day/night) and at 80% relative humidity. Grading (% of efficacy) is carried out 5 to 7 days after the contamination, in comparison with the control plants.
25
The following table summarises the results obtained when tested compound 1 and myclobutanil alone and in different weight ratio mixtures.

•    Dose
(1)Pni)    To Efficacy    Synergism
(Colby)
-
Compound 1    12.3    0   
    37    50    -
Myclobutanil    333    0    -
Compound 1 + myclobutanil
(Ratio 1:27)    12.3 + 333    53    + 53
 
22

Compound I + myclobutanil
(Ratio 1:9)    37 + 333    70    + 20

According to the Colby method, a synergistic effect of the mixtures tested has been observed.
Example 10 : Efficacy against Puccinia recandita of a mixture containing N-12-
(3-chloro-5-(trifluoromethyl)-2-pyridinyllethyll-2-trifluoromethy lbenzamide (Compound 1) and triadimenol
The active ingredients tested are prepared by potter homogenisation in a 10 mixture of acetone/tween/water . This suspension is then diluted with water to obtain the desired active material concentration.
Wheat plants (Scipion variety) in starter cups, sown on 50/50 peat soil-pozzolana substrate and grown at 12°C, are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above.
15    Plants, used as controls, are treated with an aqueous solution not containing
the active material.
After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores (100,000 spores per ml). The spores are collected from a 10-day-old contaminated wheat and are suspended in
20 water containing 2.5 m1/1 of tween 80 10%. The contaminated wheat plants are incubated for 24 hours at 20°C and at 100% relative humidity, and then for 10 days at 20°C and at 70% relative humidity. Grading is carried out 10 days after the contamination, in comparison with the control plants.
25    The following table summarises the results obtained when tested compound I
and triadimenol alone and in a 1:1 weight ratio mixture.

    Dose
(tea)    % Efficacy
_.    Synergism
(Colby)
Compound 1    250    0    -
Triadimenol    250    50    -
Compound I + triadimenol
(Ratio 1:I)    250 + 250
_    70
_    + 20
 
23
According to the Colby method, a synergistic effect of the mixtures tested has been observed.
5 Example 11 : Efficacy against Sphaerotheca fulieinea of a composition containing N-12-13-chloro-5-(trifluorarnethyll-2-nv rid inyll ethy11-2- trifluaromethylbenzamide (Compound 1) and fenhexamid
The formulated compounds are diluted with water to obtain the desired active 10    material concentration
Gherkin plants (Vert petit de Paris variety) in starter cups, sown on a 50150 peat soil-pozzolana substrate and grown at 20°C/23°C, are treated at the 2-leaves stage by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material.
15  After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Sphaerotheca fuliginea spores (100 000 spores per ml). The spores are collected from a contaminated plants .The contaminated gerkhin plants are incubated at about 20°C/25°C and at 60/70% relative humidity.
Grading (% of efficacy) is carried out 21 days after the contamination, in 2D comparison with the control plants.
The following table summarises the results obtained when tested compound 1 and fenhexamid alone and in a 1:9 weight ratio mixture.

    Dose
(ppm)    % Efficacy    Synergism
(Colby)
Compound 1    4.1    28    -
Fenhexamid    37    35    -
Compound 1 + fenhexamid
(Ratio 1:9)    4.1 + 37    74    +21

25
According to the Colby method, a synergistic effect of the mixtures tested has been observed.
 
24
Example 12 : Efficacy against Mycosphaerella eraminicola of a mixture containing N-(2-13-chloro-5-(trifluoromethyl)-2-pyridinyllethyl)-2- trifluoromethylbenzamide (Compound 1) and prochloraz
5    The formulated compounds are diluted with water to obtain the desired active
material concentration
Wheat plants (Scipion variety), sown on a 50/50 peat soil-pozzolana substrate in starter cups and grown at 12°C, are treated at the 1-Ieaf stage (10 cm tall) by spraying with the aqueous suspension described above. Plants, used as controls, are
10 treated with an aqueous solution not containing the active material.
After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Mycosphaerella graminicola spores (500 000 spores per ml). The spores are collected from a 7-day-old culture .The contaminated wheat plants are incubated for 72 hours at 18°C and at 100% relative humidity, and then for 21 to 28
15    days at 90% relative humidity.
Grading (% of efficacy) is carried out 21 to 28 days after the contamination, in comparison with the control plants.
The following table summarises the results obtained when tested compound I 20 and prochloraz alone and in a 1:4 weight ratio mixture.

    Dose
(Elba)    % Efficacy    Synergism
(Colby)
-
Compound 1    62.5    77   
Prochloraz    250    54    -
Compound 1 + Prochloraz
(Ratio 1/4)    62.5 + 250    98    +9

According to the Colby method, a synergistic effect of the mixtures tested has been observed.
 
25
Example 13 : Efficacy against Botrvtis cinerea of a mixture containing N-12-13-
chloro-5-(trifluoromethYD-2-pyridinyllethy11-2-trifluoromethylbenzamide  (Compound and fenpropimorph
5
The formulated compounds are diluted with water to obtain the desired active material concentration.
Gherkin plants (Petit veil de Paris variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 18-20°C, are treated at the cotyledon Z11
10 stage by spraying with the aqueous suspension described above. Plants, used as
controls, are treated with an aqueous solution not containing the active material.
After 24 hours, the plants are contaminated by depositing drops of an aqueous suspension of Botrytis cinerea spores (150,000 spores per ml) on upper surface of the leaves. The spores are collected from a 15-day-old culture and are suspended in a
15 nutrient solution composed of :
- 20 g/L of gelatine
- 50 g/L of cane sugar
- 2 g/L of NH4NO3
- 1 g/L of KH2PO4
20    The contaminated gherkin plants are settled for 5/7 days in a climatic room at
15-11°C (day/night) and at 80% relative humidity. Grading (% of efficacy) is carried out 5 to 7 days after the contamination, in comparison with the control plants.
The following table summarises the results obtained when tested compound 1 25 and fenpropimorph alone and in 1:2 weight ratio mixture.
    Dose
(tea)    % Efficacy    Synergism
(Colby)
Compound 1     31.2    20    -
    62.5    30    -
Fenpropimorph    62.5    10    -
    125    30    -
Compound 1 + fenpropimorph
(Ratio 1:2)    31.2 + 62.5    60    + 32
    62.5 + 125    80    + 29
 
26
According to the Colby method, a synergistic effect of the mixtures tested has been observed.
Example 14 : Efficacy against Erysiphe iframinis f. sp. Eraminis of a mixture 5    containing    N-{2-13-chloro-5-(triflu oromethy 1)-2-pyrid i nyll ethyl 1-2-
trifluo romethylbenzamide (Compound 1) and spiroxamine
The formulated compounds are diluted with water to obtain the desired active material concentration Wheat plants (Audace variety) in starter cups, sown on 50150
10 peat soil-pozzolana substrate and grown at 12°C, are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above.
Plants, used as controls, are treated with an aqueous solution not containing the active material.
After 24 hours, the plants are contaminated by dusting them with Erysiphe
15 graminis f. sp. tritici spores, the dusting being carried out using diseased plants. Grading is carried out 7 to 14 days after the contamination, in comparison
with the control plants.
The following table summarises the results obtained when tested compound I 20 and spiroxamine alone and in a 4:1 weight ratio mixture.

    Dose
(tea)    % Efficacy    Synergism
(Colby)
Compound 1    500    44    -
Spiroxamine    125    0    -
Compound 1 + spiroxamine
(Ratio 4:1)    500 + 125    72    + 28

According to the Colby method, a synergistic effect of the mixtures tested has been observed.
 
27
Example 15 : Efficacy against Botrvtis cinerea of a mixture containing N-12-13-
chloro-5-(trifluoromethyl)-2-Pyridinyllethyll-2-trifluoromethylbenzamide (Compound 1) and triforine
5
The formulated compounds are diluted with water to obtain the desired active material concentration.
Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 18-20°C, are treated at the cotyledon Z11
10 stage by spraying with the aqueous suspension described above. Plants, used as
controls, are treated with an aqueous solution not containing the active material.
After 24 hours, the plants are contaminated by depositing drops of an aqueous suspension of Botrytis cinerea spores (150,000 spores per ml) on upper surface of the leaves. The spores are collected from a 15-day-old culture and are suspended in a
15 nutrient solution composed of :
- 20 g/L of gelatine
- 50 g/L of cane sugar
- 2 g/L of NH4NO3
- 1 g/L of KH2PO4
20    The contaminated gherkin plants are settled for 5/7 days in a climatic room at
15-1 I °C (day/night) and at 80% relative humidity. Grading (% of efficacy) is carried out 5 to 7 days after the contamination, in comparison with the control plants.
The following table summarises the results obtained when tested compound 1 25 and triforine alone and in different weight ratio mixtures.

    Dose
(ppm)    % Efficacy    Synergism
(Colby)
Compound 1    37    50    -
Triforine    37    0    -
    111    15    -
Compound 1 + triforine
(Ratio 1:1)    37 + 37    65    + 15
Compound 1 + triforine
(Ratio 1:3)    37 + 111    70    + 13
 
28
According to the Colby method, a synergistic effect of the mixtures tested has been observed.
Example 16 : Efficacy at ainst &Inds cinerea of a mixture containing N-{2-13¬5 chloro-5-(trifluoromethyl)-2-pyridinvIlethyl)-2-trifluoromethylbenzamide (Compound 1) and bitertanol
The formulated compounds are diluted with water to obtain the desired active material concentration.
10    Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a 50/50
peat soil-pozzolana substrate and grown at 18-20°C, are treated at the cotyledon Z11 stage by spraying with the aqueous suspension described above. Plants, used as controls, are treated with an aqueous solution not containing the active material.
After 24 hours, the plants are contaminated by depositing drops of an aqueous
15 suspension of Botrytis cinerea spores (150,000 spores per ml) on upper surface of the leaves. The spores are collected from a 15-day-old culture and are suspended in a nutrient solution composed of :
- 20 g/L of gelatine
- 50 g/L of cane sugar
20    - 2 g/L of NH4NO3
-1 g/L of ICH2PO4
The contaminated gherkin plants are settled for 5/7 days in a climatic room at 15-11°C (day/night) and at 80% relative humidity. Grading (% of efficacy) is carried out 5 to 7 days after the contamination, in comparison with the control plants.
25
The following table summarises the results obtained when tested compound 1 and bitertanol alone and in a 1:9 weight ratio mixture.

    Dose
(PPm)    % Efficacy    Synergism
(Colby)
Compound 1    12.3    5    -
Bitertenol    333    0    -
Compound 1 + bitertanol
(Ratio 1:9)    12.3 + 333    95    + 90
 
29
According to the Colby method, a synergistic effect of the mixture tested has been observed.
Example 17 : Efficacy against Ervsiphe Rraminis f. sp. ,graminis of a mixture 5 containing    N-12-13-chloro-5-(trifluoromethyl)-2-nvridirtyllethyll-2-
trifluoromethylbenzamide (Compound 11, spiroxamine and nrothioconazole
The formulated compounds (Compound 1 and a mix of spiroxamine (300g11) and prothioconazole (160g/l) are diluted with water to obtain the desired active
10 material concentration Wheat plants (Audace variety) in starter cups, sown on 50/50 peat soil-pozzolana substrate and grown at 12°C, are treated at the 1-leaf stage (10 cm tall) by spraying with the aqueous suspension described above.
Plants, used as controls, are treated with an aqueous solution not containing the active material.
15    After 24 hours, the plants are contaminated by dusting them with Erysiphe
graminis f. sp. tritici spores, the dusting being carried out using diseased plants. Grading is carried out 7 to 14 days after the contamination, in comparison with the control plants.
20    The following table summarises the results obtained when tested compound 1
and the mix of spiroxamine and prothioconazole alone and in a 8:1 weight ratio mixture.

    Dose
(010    % Efficacy    Synergism
(Colby)
Compound 1    125    0    -
Spiroxamine +
prothioconazole    15.6    45    -
CoMpound I + spiroxamine +
prothioconazole
(Ratio 8:1)    125+ 15.6    95    + 50

25 According to the Colby method, a synergistic effect of the mixtures tested has been observed.
 
30
CLAIMS
5 1.    A composition comprising :
a) a pyridylethylbenzamide derivative of general formula (I)
(X)15(..
in which :
- p is an integer equal to 1, 2, 3 or 4;
- q is an integer equal to 1, 2, 3, 4 or 5;
10    - each substituent X is chosen, independently of the others, as being halogen, alkyl or
haloalkyl;
- each substituent Y is chosen, independently of the others, as being halogen, alkyl,
alkenyl, alkynyl, haloalkyl, alkoxy, amino, phenoxy, alkylthio, dialkylamino, acyl,
cyano, ester, hydroxy, aminoalkyl, benzyl, haloalkoxy, halosulphonyl, halothioalkyl,
15 alkoxyalkenyl, alkylsulphonamide, nitro, alkylsulphonyl, phenylsulphonyl or benzylsulphonyl;
as to the N-oxides of 2-pyridine thereof;
and
b) a compound capable of inhibiting the ergosterol biosynthesis;
20 in a (a) / (b) weight ratio of from 0.01 to 20.
2.    A composition according to claim 1, characterised in that p is 2.
3.    A composition according to claim 1 or 2, characterised in that q is or 2.
25
4.    A composition according to any of the claims 1 to 3, characterised in that X is
chosen, independently of the others, as being halogen or haloalkyl.
5.    A composition according to any of the claims 1 to 4, characterised in that X is
30 chosen independently of the others, as being a chloro atom or a trifluoromethyl group.
 
31
6.    A composition according to any of the claims 1 to 5, characterised in that Y is
chosen, independently of the others, as being halogen or haloalkyl.
5    7.    A composition according to any of the claims 1 to 6, characterised in that Y is
chosen, independently of the others, as being a chloro atom or a trifluoromethyl group.
8.    A composition according to any of the claims 1 to 7, characterised in that the
10 compound of general formula (I) is :
- N-1243-chloro-5-(trifluoromethyl)-2-pyridinyllethy1}-2-trifluoromethylbenzamide; - N-(243 -chloro-5-(trifl uoromethyl)-2-pyridinyllethyll-2-iodobenzamide; or
- N-{213,5-dichloro-2-pyridinyllethyl}-2-trifluoromethylbenzamide
15    9.    A composition according to claim 8, characterised in that the compound of
general formula (I) is N- (243-chloro-5-(trifluoromethyl)-2-pyridinyllethyl) -2- trifluoromethylbenzamide.
10.    A composition according to any of the claims 1 to 9, characterised in that the
20    compound capable of inhibiting the ergosterol biosynthesisis is a triazole derivative.
11.    A composition according to claim 10, characterised in that the triazole derivative is azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol,
25 hexaconawle, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, diclobutrazole, etaconazole, fluotrimazole, furconazole, furconazole-cis, triamiphos or triazbutil.
30    12.    A composition according to any of the claims 1 to 9, characterised in that the
compound capable of inhibiting the ergosterol biosynthesisis is an imidazole derivative.
13.    A composition according to claim 12, characterised in that the imidazole
35        derivative is imazalil, prochloraz, oxpoconazole fumarate, pefurazoate or
triflumizole.
 
32
    14.    A composition according to any of the claims 1 to 9, characterised in that the
compound capable of inhibiting the ergosterol biosynthesis is a morpholine derivative.
    5 15.    A composition according to claim 14, characterised in that the morpholine
derivative is aldimorph, dodemorph, fenpropimorph or tridemorph.
    16.    A composition according to any of the claims 1 to 9, characterised in that the
compound capable of inhibiting the ergosterol biosynthesis is a piperidine derivative.
10
    17:    A composition according to claim 16, characterised in that the piperidine
derivative is fenpropidin or piperalin.
18.    A composition according to any of the claims 1 to 9, characterised in that the 15 compound capable of inhibiting the ergosterol biosynthesis is fenhexamid, spiroxamine or triforine.
19.    Acomposition according to any one of the claims 1 to 18 further comprising a fungicidal compound (c).
20
20.    A composition according to claim 19, characterised in that the fungicidal compound (c) is selected from trifloxystrobin, fluoxastrobin, pyrimethanil, thiabendazole, guazatine, imidoctadine, picoxystrobin, pyraclostrobin, azoxystrobin, dimoxystrobin, metaminostrobin, 2-{2-[6-(3-chloro-2-methylphenoxy)-5-fluoro-
25 pyrimidin-4-yloxyl-pheny1)2-methoxyirnino-N-methyIacetamide, captane, dodine, propineb, mancozeb, spiroxamine, prothioconazole, tebuconazole, thirame, tolyifluanid, iminoctadine, dithianon, sulphur, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, dinocap, quinoxyfen, 2-butoxy-6-iodo-3-propyl¬benzopyran-4-one, fludioxonil, triazoxide, fosetyl-Al and phosphorous acid.
30
21.    A composition according to any one of the claims 1 to 20, characterised in that it further comprises an agriculturally acceptable support, carrier, filler and/or surfactant.
    35 22.    A method for preventively or curatively controlling phytopathogenic fungi of
crops, characterised in that an effective and non-phytotoxic amount of a composition
 
33
 
aceordin3 Co any croa of thu claim$ 1 lc 21 is arpd Lod to thc six& the ;Alit and:or to the
fi ti t of the plant Of &the liLL1 III %Lich the pbal is !grow irg of in which it i$ c:ILKSTICI 10
 
indexation.Ist QCOK tags.Ist

Newsletter

Join our newsletter for CIPIT news through subscriptions!

SEND

Social Media

    

Contact Us

TEL : (254) 703 034 612