WO2005103004A1 - 2-pyridinylcycloalkylbenzamide derivatives and their use as fungicides - Google Patents
2-pyridinylcycloalkylbenzamide derivatives and their use as fungicides Download PDFInfo
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- WO2005103004A1 WO2005103004A1 PCT/EP2005/005800 EP2005005800W WO2005103004A1 WO 2005103004 A1 WO2005103004 A1 WO 2005103004A1 EP 2005005800 W EP2005005800 W EP 2005005800W WO 2005103004 A1 WO2005103004 A1 WO 2005103004A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Definitions
- the present invention relates to novel N-[2-(2- pyridinyl)cycloalkyl]benzamide derivatives, their process of preparation, their use as fungicides, particularly in the form of fungicidal compositions, and methods for the control of phytopathogenic fungi of plants using these compounds or their compositions.
- International patent application WO 01/11965 discloses a broad family of fungicidal compounds.
- N-[2-(2- pyridinyl)cycloalkyl]benzamide derivatives It is always of high-interest in the field of agrochemicals to use pesticidal compounds more active than the compounds already known by the man ordinary skilled in the art whereby less compound can be used whilst retaining equivalent efficacy.
- the present invention relates to a N-[2-(2- pyridinyl)cycloalkyl]benzamide derivative of general formula (I)
- - halogen means fluorine, bromine, chlorine or iodine.
- the invention thus relates equally to all the optical isomers and to their racemic or scalemic mixtures (the term "scalemic” denotes a mixture of enantiomers in different proportions), and to the mixtures of all the possible stereoisomers, in all proportions.
- the diastereoisomers and/or the optical isomers can be separated according to the methods which are known per se by the man ordinary skilled in the art. Any of the compound of the present invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound.
- the invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions.
- the geometric isomers can be separated according to general methods, which are known per se by the man ordinary skilled in the art. Any of the compound of general formula (I) wherein Ri represents a hydroxy or sulfanyl group, and/or X represents a hydroxy, sulfanyl or amino group, may be found in its tautomeric form resulting of the shift of the proton of said hydroxy, sulfanyl or amino group. Such tautomeric forms of such compounds are also part of the present invention.
- the 2-pyridyl may be substituted in every position by (X) n and R a , in which X, R a and n are as defined above.
- the present invention relates to N-[2-(2-pyridinyl)cycloalkyl]benzamide derivative of general formula (I) in which the different characteristics may be chosen alone or in combination as being :
- n is 1 or 2. More preferably n is 1.
- X is preferably chosen as being a halogen atom. More preferably X is chlorine; - as regards R a , R a is preferably chosen as being -CF 3 ;
- the 2-pyridyl is substituted in 3- and/or in 5 -position. More preferably, the 2-pyridyl is substituted in 3 -position by X and in 5 -position by R a . Even more preferably, the 2-pyridyl is substituted in 3-position by -CI and in 5 -position by -CF 3 .
- A is a 3-, 4-, 5-, 6- or 7-membered non aromatic carbocycle.
- A is a 3-, 5-, 6- or 7-membered non aromatic carbocycle.
- A is chosen from cyclopropyl, cyclopentyl, cyclohexyl and cycloheptyl.
- the phenyl group is substituted in any position by (Y) p , in which Y and p are as defined above.
- the present invention relates to N-[2-(2-pyridinyl)cycloalkyl]benzamide derivative of general formula (I) in which the different characteristics may be chosen alone or in combination as being : - as regards p, p is 1 or 2;
- Y is a hydrogen atom, a halogen atom, a Ci-C ⁇ -alkyl, a -C ⁇ -alkoxy or a Ci-C ⁇ -halogenoalkyl having 1 to 5 halogen atoms;
- the phenyl moiety is substituted by Y preferentially first in ortho position.
- the present invention also relates to N-[2-(2- pyridinyl)cycloalkyl]benzamide derivative of general formula (I) in which R 1 and R 2 may be chosen, independently of each other, as being a hydrogen atom, a halogen atom, a cyano group, a hydroxy group, a Ci-C 6 -alkyl, a C C ⁇ -halogenoalkyl having 1 to 5 halogen atoms, a C 2 -C 6 -alkenyl, a -C ⁇ -alkoxy, a C ⁇ -C 6 -alkylsulfanyl, a Ci- C 6 -alkylsulfenyl, a CrC ⁇ -alkylsulfinyl, a CrCe-alkoxycarbonyl, a
- R 1 and R 2 may be chosen, independently of each other, as being a hydrogen atom, a halogen atom, a C t -C ⁇ -alkyl, a C ⁇ -C 6 - halogenoalkyl having 1 to 5 halogen atoms or a Ci-C 6 -alkylcarbonylamino. Even 1 9 more preferably, R and R are both a hydrogen atom.
- the nitrogen atom of the carboxamide moiety of the compound of formula (I) is substituted by R 3 , R 3 being as defined above.
- the present invention also relates to N-[2-(2- pyridinyl)cycloalkyl]benzamide derivative of general formula (I) in which R 3 may be chosen as being a hydrogen atom or a C 3 -C 7 -cycloalkyl. Even more preferably, the C 3 -C -cycloalkyl is cyclopropyl.
- the present invention also relates to a process for the preparation of the compound of general formula (I).
- a process for the preparation of compound of general formula (I) as defined above which comprises reacting a 2-pyridine derivative of general formula (II) or one of its salt :
- - L is a leaving group chosen as being a halogen atom, a hydroxyl group, -OR , - 7 7 OCOR , R being a Ci-C 6 alkyl, a C ⁇ -C 6 haloalkyl, a benzyl, 4-methoxybenzyl, pentafluorophenyl or a group of formula in the presence of a catalyst and, if L 1 is a hydroxyl group, in the presence of a condensing agent.
- the process according to the present invention is conducted in the presence of a catalyst.
- Suitable catalyst may be chosen as being 4-dimethyl-aminopyridine, 1- hydroxy-benzotriazole or dimethylformamide.
- L 1 is a hydroxy group
- the process according to the present invention is conducted in the presence of condensing agent.
- Suitable condensing agent may be chosen as being acid halide former, such as phosgene, phosphorous tribromide, phosphorous trichloride, phosphorous pentachloride, phosphorous trichloride oxide or thionyl chloride; anhydride former, such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl- chloride; carbodiimides, such as N s N'-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorous pentoxide, polyphosphoric acid, N,N'-carbonyl-diimidazole, 2-ethoxy-N-ethoxycarbonyl- 1 ,2-dihydroquinoline
- acid halide former such as phosgene, phosphorous tribromide, phosphorous trichloride,
- EEDQ triphenylphosphine/tetrachloromethane
- - R 1 , R 2 , A, R a , X,Y, n and p are as defined above;
- - R 3a is chosen as being a hydrogen atom, a cyano group, a formyl group, a hydroxy group, a CrC 6 -alkyl, a CrC ⁇ -halogenoalkyl having 1 to 5 halogen atoms, a C ⁇ -C 6 -alkoxy, a C ⁇ -C 6 -halogenoalkoxy having 1 to 5 halogen atoms, a C 3 -C 6 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 2 -C 6 -alkenyl, a C 2 -C 6 -alkynyl, a -C ⁇ -alkoxy-Ci-Ce-alkyl, a CrCe-cyanoalkyl, a Cr -aminoalkyl, a Ci-C ⁇
- amine derivatives of general formula (II) may be prepared by different processes.
- One example (a) of such a process may be when : - R 1 , R 2 , A, R a , X, n are as defined above; - R 3 is a hydrogen atom, a -C ⁇ alkyl, a C ⁇ -C 6 haloalkyl, a alkoxy or a C 3 -C cycloalkyl; then, the amine derivative of general formula (II) may be prepared according to a process comprising :
- VIII (Ha) in which : - R a , A, X and n are as defined above; - R 1 is a hydrogen atom, a Ci-C ⁇ alkyl, - R 3 is a hydrogen atom, a C C 6 alkyl, a Ci-C 6 haloalkyl, a C C ⁇ alkoxy or a C 3 -C cycloalkyl; comprising the reduction of an imine derivative of general formula (VIII) by hydrogenation or by an hydride donor, in the same or a different pot to provide an amine derivative of general formula (Ila) or one of its salt.
- a second example (b) of such a process may be when : - R a , R 2 , R 3 , A, X and n are as defined above;
- the amine derivative of general formula (II) may be prepared according to a process comprising :
- reaction scheme b-1 a first step according to reaction scheme b-1 :
- - R a , R 2 , A, X and n are as defined above;
- - U is a leaving group chosen as being a halogen, a Ci-C ⁇ alkylsulfonate or a Ci-C ⁇ haloalkylsulfonate;
- - M is a metal or a metalloid specie; comprising a coupling reaction of a pyridine derivative of general formula (IV) with a vinylic specie of general formula (IX), at a temperature of from 0°C to 200°C, to provide a compound of general formula (X);
- - a second step according to reaction scheme b-2 Scheme b-2
- step b-1 of the process b according to the present invention is conducted in the presence of a vinylic specie of general formula (IX) in which M can be a metal or a metalloid specie.
- M can be a metal or a metalloid specie.
- M is a tin derivative or a boron derivative. More preferably M is a tri- «butyltin group.
- the first step (step b-1) of the process b according to the present invention is conducted at a temperature of from 0°C to 200°C.
- the first step (step b-1) of the process b according to the present invention may be conducted in the presence of a solvent.
- the solvent is chosen as being water, an organic solvent or a mixture of both. Suitable organic solvents may for example be aliphatic, alicyclic or aromatic solvent.
- the first step (step b-1) of the process b according to the present invention may also be conducted in the presence of a catalyst.
- the catalyst is chosen as being palladium salts or complexes. More preferably, the catalyst is chosen as being a palladium complex.
- Suitable palladium complex catalyst may for example be generated directly in the reaction mixture by separately adding to the reaction mixture a palladium salt and a complex ligand.
- Suitable ligands may for example be bulky phosphines or arsines ligands, such as (R)-(-)-l-[(S)-2- (dicyclohexylphosphino)ferrocenyl] ethyldicyclohexylphosphine and its corresponding enantiomer, or a mixture of both; (R)-(-)-l[(S)-2- (dicyclohexylphosphino)ferrocenyl]ethyldiphenylphosphine and its corresponding enantiomer, or a mixture of both; (R)-(-)-l[(S)-2-
- the first step (step b-1) of the process b according to the present invention may also be conducted in the presence of a base.
- the base is chosen as being an inorganic or an organic base. Suitable examples of such bases may for example be alkaline earth metal or alkali metal hydrides, hydroxides, amides, alco- holates, carbonates or hydrogen carbonates, acetates or tertiary amines.
- a third example (c) of such a process may be when - R a , R 1 , X, n are as defined above; - R 2 , R 3 are a hydrogen atom - A is a cyclopropyl ring; then, the amine derivative of general formula (II) may be prepared according to a process comprising :
- R a , R 1 , X and n are as defined above; comprising a rearrangement reaction of a primary amide derivative of general formula (XVI) in presence of a halogenating agent, to provide an amine of general formula (lie).
- the first step (step c-1) of the process c according to the present invention is conducted in the presence of a vinylic specie of general formula (XII) in which M can be a metal or a metalloid specie.
- M can be a metal or a metalloid specie.
- M is a tin derivative or a boron derivative. More preferably M is a tri- ⁇ butyltin group.
- the first step (step c-1) of the process c according to the present invention is conducted at a temperature of from 0°C to 200°C.
- the first step (step c-1) of the process c according to the present invention may be conducted in the presence of a solvent.
- the solvent is chosen as being water, an organic solvent or a mixture of both.
- Suitable organic solvents may for example be aliphatic, alicyclic or aromatic solvent.
- the first step (step c-1) of the process c according to the present invention may also be conducted in the presence of a catalyst.
- the catalyst is chosen as being palladium salts or complexes. More preferably, the catalyst is chosen as being a palladium complex.
- Suitable palladium complex catalyst may for example be generated directly in the reaction mixture by separately adding to the reaction mixture a palladium salt and a complex ligand.
- Suitable ligands may for example be bulky phosphines or arsines ligands, such as (R)-(-)-l-[(S)-2- (dicyclohexylphosphino)ferrocenyl]ethyldicyclohexylphosphine and its corresponding enantiomer, or a mixture of both; (R)-(-)-l[(S)-2- (dicyclohexylphosphino)ferrocenyl]ethyldiphenylphosphine and its corresponding enantiomer, or a mixture of both; (R)-(-)-l[(S)-2- (diphenylphosphino)ferrocenyl]ethyldi-t-butylphosphine and its corresponding enantiomer, or a mixture of both; or (R)-(-)-l[(S)-2- (diphenylphosphino)ferrocenyl
- the first step (step c-1) of the process c according to the present invention may also be conducted in the presence of a base.
- the base is chosen as being an inorganic or an organic base. Suitable examples of such bases may for example be alkaline earth metal or alkali metal hydrides, hydroxides, amides, alco- holates, carbonates or hydrogen carbonates, acetates or tertiary amines.
- Compounds according to the present invention can be prepared according to the above described processes. It will nevertheless be understood that, on the basis of his general knowledge and of available publications, the skilled worker will be able to adapt these processes according to the specifics of each of the compounds which it is desired to synthesise.
- the present invention also relates to a fungicidal composition comprising an effective amount of an active material of general formula (I).
- a fungicidal composition comprising, as an active ingredient, an effective amount of a compound of general formula (I) as defined above and an agriculturally acceptable support, carrier or filler.
- 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.
- 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 additional components.
- 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 mixture of such surfactants.
- 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 amines substituted phenols (in particular alkylphenols or
- 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 vector agent for the application is water.
- 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.
- the active materials can be combined with any solid or liquid additive, which complies with the usual formulation techniques.
- 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 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, 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.
- These compositions include not only compositions which are ready to be applied to the plant or seed
- the compounds of the invention can also be mixed with one or more insecticides, fungicides, bactericides, attractant acaricides or pheromones or other compounds with biological activity.
- the mixtures thus obtained have a broadened spectrum of activity.
- the mixtures with other fungicides are particularly advantageous.
- the fungicidal compositions of the present invention can be used to curatively or preventively control the phytopathogenic fungi of crops.
- a method for curatively or preventively controlling the 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.
- the composition as used against phytopathogenic fungi of crops comprises an effective and non-phytotoxic amount of an active material of general formula (I).
- an amount of composition according to the invention 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 symptom of phytotoxicity for the said crops.
- Such an amount can vary within a wide range depending on the fungus to be controlled, the type of crop, the climatic conditions and the compounds included in the fungicidal composition according to the invention. This amount can be determined by systematic field trials, which are within the 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 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.
- 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.
- leguminous crops such as 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); big crops such as Graminae sp. (for instance maize, cereals such as wheat, rice, barley and triticale), Asteraceae sp. (for instance sunflower), Cruciferae sp.
- Solanaceae sp. for instance tomatoes
- Liliaceae sp. for instance lettuces
- Umbelliferae sp. for instance lettuces
- Cruciferae sp. Chenopodiaceae sp.
- Cucurbitaceae sp. for instance peas
- - wheat as regards controlling the following seed diseases: fusaria (Microdochium nivale and Fusarium roseum), stinking smut (Tilletia caries, Tilletia controversa or Tilletia indic ⁇ ), 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 (Gaeumannomyces graminis), foot blight (F. culmorum, F.
- - wheat and barley as regards controlling bacterial and viral diseases, for 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 plant: cereal eyespot (Tapesia yallundae), net blotch (Pyrenophora teres and Coch
- fungicide composition according to the present invention may also be used against fungal diseases liable to grow on or inside timber.
- Timber 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, dipping, injection or any other suitable means.
- the dose of active material usually applied in the treatment according to the present invention is generally and advantageously between 10 and 800 g/ha, preferably between 50 and 300 g/ha for applications in foliar treatment.
- the dose of active substance applied is generally and advantageously between 2 and 200 g per 100 kg of seed, preferably between 3 and 150 g per 100 kg of seed in the case of seed 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 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 whose genome a 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.
- compositions according to the present invention may also be used for 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., for example Aspergillus fumigatus.
- fungal diseases such as, for example, mycoses, dermatoses, trichophyton diseases and candidiases or diseases caused by Aspergillus spp., for example Aspergillus fumigatus.
- M+1 means the molecular ion peak, plus or minus 1 a.m.u. (atomic mass units) respectively, as observed in mass spectroscopy.
- Example A in vivo test on Alternaria brassicae (Leaf spot of crucifers)
- the active ingredient tested is prepared by potter homogenisation in a concentrated suspension type formulation at 100 g/1. This suspension is then diluted with water to obtain the desired active material concentration. Radish plants (Pernot variety) in starter cups, sown on a 50/50 peat soil-pozzolana substrate and grown at 18-20°C, are treated at the cotyledon 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 spraying them with an aqueous suspension of Alternaria brassicae spores (40,000 spores per cm 3 ). The spores are collected from a 12-13-day-old culture.
- the contaminated radish plants are incubated for 6-7 days at about 18°C, under a humid atmosphere. Grading is carried out 6 to 7 days after the contamination, in comparison with the control plants. Under these conditions, good (at least 50%) or total protection is observed at a dose of 330ppm with the following compounds : 1, 2, 3, 4 and 5.
- Example B in vivo test on Erysiphe sraminis f. sp. tritici (powdery mildew of wheat)
- the active ingredient tested is prepared by potter homogenisation in a concentrated suspension type formulation at 100 g/l.This suspension is then diluted with water to obtain the desired active 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. 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. Under these conditions, good (at least 50%) or total protection is observed at a dose of 330 ppm with the following compounds : 1 and 2.
- Example C in vivo test on Pyrenophora teres (Barley Net blotch).
- the active ingredient tested is prepared by potter homogenisation in a concentrated suspension type formulation at 100 g/1. This suspension is then diluted with water to obtain the desired active material concentration. Barley plants (Express variety) in starter cups, sown on a 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. After 24 hours, the plants are contaminated by spraying them with an aqueous suspension of Pyrenophora teres spores (12,000 spores per ml).
- the spores are collected from a 12-day-old culture .
- the contaminated barley plants are incubated for 24 hours at about 20°C and at 100% relative humidity, and then for 12 days at 80% relative humidity. Grading is carried out 12 days after the contamination, in comparison with the control plants. Under these conditions, good (at least 50%) or total protection is observed at a dose of 330 ppm with the following compounds : 1, 2, 3, 4, 5, 6 and 7.
- N- ⁇ l-methylcarbamoyl-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]- ethyl ⁇ -4-phenylbenzamide disclosed by Patent Application WO 01/11965 showed poor effectiveness on Alternaria brassicae, and zero effectiveness on Botrytis cinerea at 330 ppm;
- the N- ⁇ l-ethylcarbamoyl- 2- [3 -chloro-5 -(trifluoromethyl)-2-pyridinyl] ethyl ⁇ -3 -nitrobenzamide also disclosed by Patent Application WO 01/11965 (see compound 307 in Table D) showed poor effectiveness on Alternaria brassicae and zero effectiveness on Botrytis cinerea at 330 ppm;
Abstract
Description
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Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002560692A CA2560692A1 (en) | 2004-04-26 | 2005-04-25 | 2-pyridinylcycloalkylbenzamide derivatives and their use as fungicides |
BRPI0508745-7A BRPI0508745A (en) | 2004-04-26 | 2005-04-25 | compost, process for preparing a compost, fungicidal composition and method for preventively or curatively combating plant pathogenic fungi |
JP2007509999A JP2007534721A (en) | 2004-04-26 | 2005-04-25 | 2-pyridinylcycloalkylbenzamide derivatives and their use as fungicides |
MXPA06012160A MXPA06012160A (en) | 2004-04-26 | 2005-04-25 | 2-pyridinylcycloalkylbenzamide derivatives and their use as fungicides. |
EP05744556A EP1740542A1 (en) | 2004-04-26 | 2005-04-25 | 2-pyridinylcycloalkylbenzamide derivatives and their use as fungicides |
US11/587,908 US7524968B2 (en) | 2004-04-26 | 2005-04-25 | 2-pyridinylcycloalkylbenzamide derivatives and their use as fungicides |
IL178765A IL178765A0 (en) | 2004-04-26 | 2006-10-19 | 2-pyridinylcycloalkylbenzamide derivatives and their use as fungicides |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04356056.4 | 2004-04-26 | ||
EP04356056A EP1591442A1 (en) | 2004-04-26 | 2004-04-26 | 2-Pyridinycycloalkylbenzamide derivatives and their use as fungicides |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005103004A1 true WO2005103004A1 (en) | 2005-11-03 |
Family
ID=34931748
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2005/005800 WO2005103004A1 (en) | 2004-04-26 | 2005-04-25 | 2-pyridinylcycloalkylbenzamide derivatives and their use as fungicides |
Country Status (11)
Country | Link |
---|---|
US (1) | US7524968B2 (en) |
EP (2) | EP1591442A1 (en) |
JP (1) | JP2007534721A (en) |
KR (1) | KR20070004124A (en) |
CN (1) | CN1946694A (en) |
BR (1) | BRPI0508745A (en) |
CA (1) | CA2560692A1 (en) |
IL (1) | IL178765A0 (en) |
MX (1) | MXPA06012160A (en) |
WO (1) | WO2005103004A1 (en) |
ZA (1) | ZA200608237B (en) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2289880A1 (en) | 2009-07-08 | 2011-03-02 | Bayer CropScience AG | 2-Pyridinylcyclopropylbenzamide fungicides |
EP2589292A1 (en) | 2011-11-02 | 2013-05-08 | Bayer CropScience AG | Compounds with nematicidal activity |
EP2589294A1 (en) | 2011-11-02 | 2013-05-08 | Bayer CropScience AG | Compounds with nematicidal activity |
WO2013064460A1 (en) | 2011-11-02 | 2013-05-10 | Bayer Intellectual Property Gmbh | Compounds with nematicidal activity |
WO2013064461A2 (en) | 2011-11-02 | 2013-05-10 | Bayer Intellectual Property Gmbh | Compounds with nematicidal activity |
EP2606728A1 (en) | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | Compounds with nematicidal activity |
EP2606727A1 (en) | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | Compounds with nematicidal activity |
EP2644595A1 (en) | 2012-03-26 | 2013-10-02 | Syngenta Participations AG. | N-Cyclylamides as nematicides |
WO2015003951A1 (en) | 2013-07-08 | 2015-01-15 | Syngenta Participations Ag | 4-membered ring carboxamides used as nematicides |
WO2015040141A1 (en) | 2013-09-23 | 2015-03-26 | Syngenta Participations Ag | Cyclobutylcarboxamides as nematicides |
US9776967B2 (en) | 2013-10-14 | 2017-10-03 | Bayer Animal Health Gmbh | Carboxamide derivatives as pesticidal compounds |
WO2018114657A1 (en) | 2016-12-20 | 2018-06-28 | Syngenta Participations Ag | N-cyclobutyl-thiazol-5-carboxamides with nematicidal activity |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1885698A1 (en) * | 2005-05-18 | 2008-02-13 | Bayer CropScience S.A. | 2-pyridinylcycloalkylbenzamide derivatives and their use as fungicides |
BRPI0712027B1 (en) * | 2006-05-18 | 2015-12-15 | Syngenta Ltd | microbiocidal compounds, method and composition for control and protection against phytopathogenic microorganisms |
CN105452225B (en) | 2013-08-13 | 2018-07-06 | 先正达参股股份有限公司 | Cyclobutylmethyl amide compound as nematicide |
Citations (3)
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WO1999042447A1 (en) * | 1998-02-19 | 1999-08-26 | Aventis Cropscience Uk Limited | 2-pyridylmethylamine derivatives useful as fungicides |
WO2001011965A1 (en) * | 1999-08-18 | 2001-02-22 | Aventis Cropscience Gmbh | Fungicides |
WO2004016088A2 (en) * | 2002-08-12 | 2004-02-26 | Bayer Cropscience S.A. | Novel 2-pyridylethylbenzamide derivative |
-
2004
- 2004-04-26 EP EP04356056A patent/EP1591442A1/en not_active Withdrawn
-
2005
- 2005-04-25 CN CNA2005800127425A patent/CN1946694A/en active Pending
- 2005-04-25 BR BRPI0508745-7A patent/BRPI0508745A/en not_active IP Right Cessation
- 2005-04-25 MX MXPA06012160A patent/MXPA06012160A/en not_active Application Discontinuation
- 2005-04-25 EP EP05744556A patent/EP1740542A1/en not_active Withdrawn
- 2005-04-25 JP JP2007509999A patent/JP2007534721A/en active Pending
- 2005-04-25 WO PCT/EP2005/005800 patent/WO2005103004A1/en active Application Filing
- 2005-04-25 KR KR1020067024596A patent/KR20070004124A/en not_active Application Discontinuation
- 2005-04-25 CA CA002560692A patent/CA2560692A1/en not_active Abandoned
- 2005-04-25 US US11/587,908 patent/US7524968B2/en not_active Expired - Fee Related
-
2006
- 2006-10-03 ZA ZA200608237A patent/ZA200608237B/en unknown
- 2006-10-19 IL IL178765A patent/IL178765A0/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999042447A1 (en) * | 1998-02-19 | 1999-08-26 | Aventis Cropscience Uk Limited | 2-pyridylmethylamine derivatives useful as fungicides |
WO2001011965A1 (en) * | 1999-08-18 | 2001-02-22 | Aventis Cropscience Gmbh | Fungicides |
WO2004016088A2 (en) * | 2002-08-12 | 2004-02-26 | Bayer Cropscience S.A. | Novel 2-pyridylethylbenzamide derivative |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2289880A1 (en) | 2009-07-08 | 2011-03-02 | Bayer CropScience AG | 2-Pyridinylcyclopropylbenzamide fungicides |
US20140249149A1 (en) * | 2011-11-02 | 2014-09-04 | Bayer Intellectual Property Gmbh | Compounds with Nematicidal Activity |
EP2589292A1 (en) | 2011-11-02 | 2013-05-08 | Bayer CropScience AG | Compounds with nematicidal activity |
WO2013064460A1 (en) | 2011-11-02 | 2013-05-10 | Bayer Intellectual Property Gmbh | Compounds with nematicidal activity |
WO2013064461A2 (en) | 2011-11-02 | 2013-05-10 | Bayer Intellectual Property Gmbh | Compounds with nematicidal activity |
US9301526B2 (en) | 2011-11-02 | 2016-04-05 | Bayer Intellectual Property Gmbh | Compounds with nematicidal activity |
EP2589294A1 (en) | 2011-11-02 | 2013-05-08 | Bayer CropScience AG | Compounds with nematicidal activity |
EP2606728A1 (en) | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | Compounds with nematicidal activity |
EP2606727A1 (en) | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | Compounds with nematicidal activity |
WO2013143811A1 (en) | 2012-03-26 | 2013-10-03 | Syngenta Participations Ag | N-cyclylamides as nematicides |
EP2644595A1 (en) | 2012-03-26 | 2013-10-02 | Syngenta Participations AG. | N-Cyclylamides as nematicides |
WO2015003951A1 (en) | 2013-07-08 | 2015-01-15 | Syngenta Participations Ag | 4-membered ring carboxamides used as nematicides |
WO2015040141A1 (en) | 2013-09-23 | 2015-03-26 | Syngenta Participations Ag | Cyclobutylcarboxamides as nematicides |
US9776967B2 (en) | 2013-10-14 | 2017-10-03 | Bayer Animal Health Gmbh | Carboxamide derivatives as pesticidal compounds |
WO2018114657A1 (en) | 2016-12-20 | 2018-06-28 | Syngenta Participations Ag | N-cyclobutyl-thiazol-5-carboxamides with nematicidal activity |
Also Published As
Publication number | Publication date |
---|---|
CA2560692A1 (en) | 2005-11-03 |
EP1591442A1 (en) | 2005-11-02 |
ZA200608237B (en) | 2008-06-25 |
MXPA06012160A (en) | 2007-01-31 |
US7524968B2 (en) | 2009-04-28 |
EP1740542A1 (en) | 2007-01-10 |
JP2007534721A (en) | 2007-11-29 |
US20070203204A1 (en) | 2007-08-30 |
IL178765A0 (en) | 2007-02-11 |
CN1946694A (en) | 2007-04-11 |
KR20070004124A (en) | 2007-01-05 |
BRPI0508745A (en) | 2007-08-14 |
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