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WO1999033810A1 - Derives amides d'acide pyridyloxy(thio)alcanoique et bactericides a usage agricole ou horticole - Google Patents

Derives amides d'acide pyridyloxy(thio)alcanoique et bactericides a usage agricole ou horticole Download PDF

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Publication number
WO1999033810A1
WO1999033810A1 PCT/JP1998/005816 JP9805816W WO9933810A1 WO 1999033810 A1 WO1999033810 A1 WO 1999033810A1 JP 9805816 W JP9805816 W JP 9805816W WO 9933810 A1 WO9933810 A1 WO 9933810A1
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Prior art keywords
group
alkyl group
come
alkyl
substituted
Prior art date
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PCT/JP1998/005816
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English (en)
Japanese (ja)
Inventor
Katsumi Masuda
Atsushi Shibayama
Katsunori Matsumoto
Norihisa Yonekura
Katsumi Furuse
Kazuo Kumakura
Norimichi Muramatsu
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Ihara Chemical Industry Co Ltd
Kumiai Chemical Industry Co Ltd
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Ihara Chemical Industry Co Ltd
Kumiai Chemical Industry Co Ltd
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Priority to AU16859/99A priority Critical patent/AU1685999A/en
Publication of WO1999033810A1 publication Critical patent/WO1999033810A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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

Definitions

  • the present invention relates to a pyridyloquin (thio) alkanoic acid amide derivative which is a novel compound not described in any literature, and a fungicide for agricultural and horticultural use containing the same as an active ingredient.
  • Japanese Patent Application Laid-Open Nos. 5-286937 and 6-36050 disclose that pyridyloxycarboxylic acid amide derivatives have bactericidal activity. .
  • the compound of the present invention is not described at all.
  • the present invention provides a pyridyloxy (thio) alkanoic acid amide derivative having a novel and excellent bactericidal activity.
  • the present inventors have synthesized various pyridyloxy (thio) alkanoic acid amide derivatives and examined the physiological activities thereof. It has been found that it has a bactericidal activity and does not cause any harm to useful crops, and thus completed the present invention.
  • the present invention provides:
  • n represents an integer of 1-4
  • R 1 represents hydrogen
  • Atom, di-alkyl group, C. Represents ⁇ CP a cycloalkyl group or a C ⁇ -C 4 Ha port alkyl group
  • R 2 and R 3 are each independently, C j C g alkyl group, C 0 -C Arukeniru group, c 3 to c Hashikuroaruki Le group (This group may be substituted by a halogen atom or a C ⁇ -C 6 alkyl group.)
  • Q is a C 2 -C p alkyl group, ethynyl group, group — COR 4 (R 4 is a
  • the C. 1 to C 6 alkyl group a linear or indicates branched alkyl group, for example, methylation group, Echiru group, n- propyl group, an isopropyl group, n- butyl group, Isobuchi Le group, sec- butyl Group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, isohexyl group, 3,3-dimethylbutyl group and the like.
  • the 99/33810 c 3 ⁇ c 6 cycloalkyl group includes for example cyclopropyl group, a cyclopentyl group, cyclohexylene a cyclohexyl group.
  • ⁇ c Ha cycloalkyl Ci ⁇ c 6 alkyl group for example, cyclopropylmethyl group, cyclopentylmethyl group, forces include cyclohexylmethyl group or the like cyclohexane, can be '.
  • the Ci ⁇ c 4 Ha port alkyl group substituted by a halogen atom, a linear or represents a branched alkyl group, for example Furuoromechiru group, chloromethyl group, blanking Romomechiru group, Jifuruoromechiru group, dichloromethyl group, Examples thereof include a dibromomethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, and a pentafluoroethyl group.
  • Halogen atom means fluorine atom, chlorine atom, bromine atom and iodine atom.
  • the C. 1 to c 6 alkoxy group a linear or branched alkoxy group, for example if main butoxy group, an ethoxy group, n - propoxy group, isopropoxy group, n- butoxy sheet group, Isobutokishi group, sec —Butoxy group, tert-butyne group, n-pentyloxy group, isopentyloxy group, n-hexyloxy group and the like.
  • c 2 -c 6 alkenyloxy group refers to a linear or branched alkenyloxy group, and examples thereof include an aryloxy group, an isopropyloxy group, a 2-butenyloxy group and the like.
  • c 2 -c 6 alkynyloxy group refers to a linear or branched alkynyloxy group, and examples thereof include a 2-propynyloxy group, a 2-butynyloxy group, and a 3-butynyloxy group. .
  • Chokukusarimata represents a branched chain alkoxy group, for example Furuorome butoxy group, Jifuruorome Bok alkoxy group, Torifuruorome butoxy group, penta full O b ethoxy And the like.
  • the ci- 6 alkylthio group is a linear or branched alkylthio group, for example, a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, a sec-butylthio group, tert- Examples thereof include a butylthio group and an n-hexylthio group.
  • the C ⁇ -C 4 haloalkylthio group, substituted by a halogen atom, a linear or branched shows an alkylthio group, for example, full-O b methyl thio group, Jifuruo Romechiruchio group, triflate Ruo b methylthio group, Pentafuruo And a loethylthio group.
  • Some of the compounds of the present invention represented by the general formula [I] have one or more asymmetric carbon atoms in the molecule, and such compounds have optical isomers. Exists. Pure individual diastereomers, enantiomers and mixtures thereof are also included in the compounds of the present invention.
  • Preferred compounds of the compound of the present invention represented by the general formula [I] include X is a methyl group, trifluoromethyl group, chlorine atom, bromine atom or iodine atom and R 1 is a hydrogen atom, methyl group or ethyl group.
  • R 2 is a hydrogen atom, a methyl group, an ethyl group or an n-propyl group
  • R 3 is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a tert-butyl group, a cyclopropyl group, a cyclopentyl group Or a compound in which Q is an ethynyl group, an acetyl group, a propionyl group, a cyclopropylcarbonyl group or a 1-hydroxyxethyl group in a dichloromethyl group.
  • Me represents a methyl group
  • Et represents an ethyl group
  • Pr represents an n-propyl group
  • Pri represents an isopropyl group
  • Bu represents an n-butyl group.
  • Bu-i represents an isobutyl group
  • Bu-t represents a tert-butyl group
  • Pr-cyc represents a cyclopropyl group
  • Pen-cyc represents a cyclopentyl group
  • P-cyc represents a cyclopentyl group.
  • h represents a phenyl group.
  • P h (4-C 1) represents a 4_chlorophenyl group. (table 1 )
  • the compound of the present invention represented by the general formula [I] can be produced, for example, according to the following production method.
  • the compound [I] of the present invention is a pyridyloxy (thio) alkane represented by the general formula [II]
  • the acid derivative can be produced by reacting an acid derivative with an amine represented by the general formula [III] using a condensing agent in the presence of a catalyst and / or a base, if necessary. This reaction is usually performed in a solvent.
  • Solvents that can be used may be solvents that do not inhibit the reaction, for example, pentane, hexane, heptane, cyclohexane, petroleum ether, rigoin, hydrocarbons such as benzene, toluene or xylene, dichloromethane, dichloroethane. Halogenated hydrocarbons such as chloroform, carbon tetrachloride, chlorobenzene, or dichlorobenzene; ethers such as ethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, or dioxane; acetone, methylethyl ketone , / Ten
  • Ketones such as methyl isopropyl ketone or methyl isobutyl ketone; acetates such as methyl acetate or ethyl acetate; ditriles such as acetonitril or propionitrile; or dimethyl sulfoxide, N,
  • a nonprotonic polar solvent such as N-dimethylformamide or sulfolane, or a mixed solvent in which a solvent selected from these is combined can be used.
  • condensing agent examples include 1-ethyl-3- (3-dimethylaminopropyl) force rubodiimide 'hydrochloride, N, ⁇ '-dicyclohexylcarbodiimide, carbonyldimidazole, and 2 — Black mouth—1,3-dimethylimidazolium chloride, etc.
  • hornworm medium examples include 4-dimethylaminopyridine, 1-hydroxybenzotriazole, dimethylformamide and the like.
  • alkali metal hydroxides such as sodium hydroxide or hydroxylated lime
  • alkaline earth metal hydroxides such as calcium hydroxide
  • alkalis such as sodium carbonate or carbonated lime
  • Metal carbonates or triethylamine, trimethylamine, ⁇ , ⁇ -methylylaniline, pyridine, ⁇ -methylpiperidine, 1,5-diazabicyclo [4.3.0] non-15-ene (DBN) or Organic bases such as 1,8-diazabicyclo [5.4.0] -17-pandacene (DBU) and the like, preferably tertiary amines such as triethylamine, pyridine and ⁇ -methylbiperidine Is mentioned.
  • the reaction temperature was 150. C. is carried out in the range of 150 ° C., preferably in the range of 0 ° C. to 100 ° C.
  • the reaction time is preferably 1 to 30 hours.
  • the compound represented by the general formula [II] can be produced, for example, according to the following production method. 99/33810
  • R 1 X, n and A represent the same meaning as described above, 6 represents a 1 to 6 alkyl group, and Z represents a leaving group such as a halogen atom.
  • the pyridyloxy (thio) alkanoic acid derivative represented by the general formula [II] can be obtained, for example, by converting a pyridine derivative represented by the general formula [IV] or [VII] in the presence of a base into the general formula [V] or [VIII] By reacting with an alkanoic acid ester derivative represented by the general formula [VI], and then hydrolyzing the pyridyloxy (thio) alkanoic acid ester derivative. be able to.
  • the reaction between the pyridine derivative represented by the general formula [IV] or [VII] and the ester derivative represented by the general formula [V] or [VIII] is usually performed in a solvent.
  • Solvents that can be used may be solvents that do not inhibit the reaction, for example, pentane, hexane, heptane, cyclohexane, petroleum ether, rig-mouth, benzene, toluene or hydrocarbons such as xylene, dichloromethane, Halogenated hydrocarbons such as chloroethane, chloroform, carbon tetrachloride, carbon benzene or dichlorobenzene, dimethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran or dioxane W 99/33810
  • Ethers acetone, methyl ethyl ketone, ketones such as methyl isopropyl ketone or methyl isobutyl ketone, ester acetates such as methyl acetate or ethyl acetate, nitriles such as acetonitrile or propionitrile,
  • a non-protonic polar solvent such as dimethyl sulfoxide, N, N-dimethylformamide or sulfolane, or a mixed solvent obtained by combining solvents selected from these solvents can be used.
  • an inorganic base such as sodium hydroxide, sodium hydroxide, sodium carbonate, carbonated carbonate, sodium bicarbonate, sodium hydride or hydrogenated potassium, or triethylamine, trimethylamine, N , N-dimethylaniline or pyridine.
  • the reaction is carried out at a temperature in the range of 50 ° C to 150 ° C, preferably in the range of 0 ° C to 100 ° C.
  • the reaction time is preferably 1 to 30 hours.
  • a reaction for hydrolyzing a pyridyloxy (thio) alkanoic acid ester derivative represented by the general formula [VI] in the presence of an acid or an alkali to obtain a pyridyloxy (thio) alkanoic acid derivative represented by the general formula [II] Is usually performed in a solvent.
  • Any solvent that does not inhibit the reaction may be used, for example, water, alcohols such as methanol, ethanol or 2-propanol, getyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran or dioxane.
  • Ethers ketones such as acetone, methylethylketone, methylisopropylketone or methylisobutylketone, or a mixed solvent obtained by combining solvents selected from these.
  • the compound represented by the general formula [III] can be prepared by a known method [for example, Journal of the Chemical Society. Parkin Transaction Society. 1, Journal of Chemical Society]. y. Perkin Transaction s. 1), Vol. 8, pp. 1645 (1998); The 'Journal' Ob '' Organic 'Chemistry (The Journal of O.) rganic Chemistry), vol. 49, p. 1208 (1 984)] or a method analogous thereto. be able to
  • the compound [I] of the present invention is a pyridine derivative represented by the general formula [VII] It can be produced by reacting with an alkanoic acid amide derivative represented by the general formula [IX] in the presence of a base. This reaction is usually performed in a solvent.
  • any solvent that does not inhibit the reaction may be used.
  • examples include pentane, hexane, heptane, cyclohexane, petroleum ether, rigoin, hydrocarbons such as benzene, toluene, and xylene, dichloromethane, and the like.
  • Halogenated hydrocarbons such as dichloroethane, chloroform, carbon tetrachloride, cyclobenzene or dichlorobenzene, ethers such as getyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran or dioxane, acetone, methyl Ketones such as rutile ketone, methyl isopropyl ketone or methyl isobutyl ketone; acetates such as methyl acetate or ethyl acetate; nitriles such as acetonitrile or pentionitrile; or dimethyl sulfoxide, N
  • Non pro ton polar solvents such as N- dimethyl formamide or sulfolane, or may be a mixed solvent combining solvents selected from these.
  • inorganic bases such as 7K sodium oxide, hydroxylated lime, sodium carbonate, carbonated lime, sodium bicarbonate, sodium hydride or hydrogenated lime, or triethylamine, trimethylamine, N, N-dimethyl Organic salts such as aniline or pyridine And the like.
  • the reaction temperature is in the range of —50 ° C. to 150 ° C., preferably 0 ° C. to 100 ° C.
  • the reaction time is preferably 1 to 30 hours.
  • the compound represented by the general formula [IX] can be produced, for example, by reacting a halogenated alkanoic acid halide with an amide derivative represented by the general formula [III]. .
  • the compound [I] of the present invention is obtained by converting a pyridine derivative represented by the general formula [IV] into a base In the presence, the compound can be produced by reacting with an alkanoic acid amide derivative represented by the general formula [X]. This reaction is usually performed in a solvent.
  • a solvent that can be used any solvent that does not inhibit the same reaction as in Production Method 2 may be used.
  • the reaction is carried out at a temperature ranging from ⁇ 50 ° C. to 150, preferably from 0 ° C. to 100 ° C.
  • the reaction time is preferably 1 to 30 hours.
  • the compound represented by the general formula [X] is obtained, for example, by reacting the halogenated alkanoic acid amide derivative represented by the general formula [IX] with sodium acetate. It can be produced by deacylation of a derivative.
  • the compound of the present invention ⁇ —II] is a pyridyloxy (thio) represented by the general formula [II]
  • the alkanoic acid amide derivative can be produced by performing a hydration reaction in the presence of an acid. This reaction is performed without a solvent or in a solvent.
  • Solvents that can be used may be any solvents that do not inhibit the reaction, such as ethers such as getyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran or dioxane, acetone, methyl ethyl ketone, and methyl iso- Ketones such as propyl ketone or methyl isobutyl ketone; acetates such as methyl acetate or ethyl acetate; nitriles such as acetonitrile or propionitrile; or dimethyl sulfoxide, N, N-dimethylformamide or sulfolane Or a mixed solvent obtained by combining solvents selected from these aprotic polar solvents.
  • ethers such as getyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran or dioxane, acetone, methyl ethyl
  • Examples of the acid include sulfuric acid, hydrochloric acid, formic acid and the like.
  • the reaction is carried out at a temperature in the range of 0 to 150 ° C, preferably in the range of 20 to 100 ° C.
  • the reaction time is preferably 1 to 10 hours.
  • the compound [I-IV] of the present invention reduces the pyridyloxy (thio) alkanoic acid amide derivative represented by the general formula [I-III]. It can be produced by reacting with an agent. This reaction is usually performed in a solvent. As a solvent that can be used, any solvent that does not inhibit the reaction may be used. For example, pentane, hexane, heptane, cyclohexane, petroleum ether, lignin, benzene, toluene, xylene, etc.
  • Halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, chlorobenzene, dichlorobenzene, ethers such as dimethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, etc. , methanol, ethanol, 2-alcohols such as propanol or water and it is in monkey c a mixed solvent of alcohol
  • reducing agent those generally used in this type of reaction can be used.
  • examples include lithium borohydride, sodium borohydride, potassium borohydride, lithium trialkylborohydride, sodium trialkylborohydride or sodium cyanoborohydride, and preferably sodium borohydride. Is mentioned.
  • the reaction is carried out at a temperature in the range of 170 ° C. to 150 ° C., preferably in the range of ⁇ 20 ° C. to 50 ° C.
  • the reaction time is preferably 1 to 30 hours.
  • the isomer A represents diastereomer A
  • the isomer B represents diastereomer B
  • the isomer M represents diastereomer mixture.
  • Diastereomer A indicates a low-polarity diastereomer separated by silica gel column chromatography or high performance liquid chromatography
  • diastereomer B indicates a similarly separated high-polarity diastereomer.
  • the agricultural and horticultural fungicide of the present invention contains a pyridyloquin (thio) carboxylic acid amide derivative represented by the general formula [I] as an active ingredient.
  • the active ingredient can be used in an appropriate dosage form depending on the purpose. Normally, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, a surfactant and other substances can be added to the active ingredient for use in the form of powders, wettable powders, emulsions, granules, etc. .
  • Suitable carriers include, for example, talc, bentonite, clay, kaolin, diatoms
  • solid carriers such as soil, white water, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea
  • liquid carriers such as 2-propyl alcohol, xylene, cyclohexanone, and methylnaphthalene.
  • surfactants and dispersants include dinaphthyl methanesulfonate, alcohol sulfate, alkylaryl sulfonate, lignin sulfonate, polyoxyethylene glycol ether, polyoxyethylene alkylaryl ether, and polyoxyethylene. Sorbi monoalkylate and the like.
  • Auxiliary agents include carboxymethylcellulose and the like. These preparations are diluted to an appropriate concentration and sprayed or applied directly.
  • the fungicide for agricultural and horticultural use of the present invention can be used by foliage application, nursery box application, soil application or water surface application.
  • the compounding ratio of the active ingredient is appropriately selected as required, but is preferably 0.1 to 20% (by weight) in the case of powders and granules, and 5 to 80% (by weight) in the case of emulsions and wettable powders. It is.
  • the application rate of the agricultural and horticultural fungicide of the present invention varies depending on the type of the compound used, the target disease, the tendency to occur, the degree of damage, the environmental conditions, the dosage form used, and the like.
  • a suitable amount from the range of O.lg to 5 kg, preferably lg to lkg, per 10 ares of the active ingredient.
  • a suitable amount from the range of O.lg to 5 kg, preferably lg to lkg, per 10 ares of the active ingredient.
  • a liquid such as an emulsion and a wettable powder
  • the compound according to the present invention can control plant diseases caused by fungi belonging to algal fungi (Oomycetes), ascomycetes (Ascomycetes), incomplete fungi (Deuteromycetes), and basidiomycetes (Basidiomycetes) by the above-mentioned application forms.
  • fungi belonging to algal fungi Olemycetes
  • ascomycetes Ascomycetes
  • Deuteromycetes incomplete fungi
  • Basidiomycetes Basidiomycetes
  • Genus Pyricularia for example, Pyricularia oryzae
  • Gibberella for example, Gibberella fujikuroi
  • Botrytis j Botrytis j
  • the compound of the present invention may be mixed with an insecticide, other fungicides, herbicides, plant growth regulators, fertilizers and the like, if necessary.
  • the formulation method will be specifically described with reference to typical examples of the agricultural and horticultural fungicides of the present invention. In the following description, “%” indicates weight percentage.
  • Emulsion was prepared by uniformly dissolving 30% of compound (A-1), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzenesulfonate and 35% of methylnaphthalene.
  • the compound of the present invention has a high control effect against rice blast and the like, and also has characteristics that it does not cause phytotoxicity to crops and has excellent residual effect and rain resistance. Useful as a fungicide.
  • Test example 1 Rice blast prevention effect test
  • Rice seedlings in the 1.5 leaf stage were transplanted into four white spots at a height of 9 cm in white porcelain pots and raised in a greenhouse.
  • the wettable powder prepared according to Formulation Example 2 at the 2.5 leaf stage was subjected to water application to the pot such that the active ingredient concentration was 300 g per 10 ares.
  • a conidia suspension of the rice blast fungus (Pyricu 1 ariaoryzae) was inoculated by spraying and immediately placed in 25 wet chambers for 24 hours. Then, they were transferred to a greenhouse, and 5 days after the inoculation, the number of lesions on the highest leaf at the time of the inoculation was examined.
  • the control value was determined by Equation 1, and the results of evaluation based on the criteria in Table 19 are shown in Tables 24 to 25.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne des dérivés amides d'acide pyridyloxy(thio)alcanoïque de la formule générale (I) dans laquelle X est hydrogène, alkyle C1-6, haloalkyle C1-4, etc.; n est un entier compris entre 1 et 4; R1 est hydrogène, alkyle C¿1-6?, etc.; R?2 et R3¿ sont chacun, indépendamment, alkyle C¿1-6?, alcényle C2-6, etc.; Q est alkyle C2-6, ethynyl, -COR?4 (R4¿ étant alkyle C¿1-6?, etc.) ou -CH(OH)R?5 (R5¿ étant alkyle C¿1-6?, etc.); et A est oxygène ou soufre. Ces bactéricides ont une action préventive sur la piriculariose du riz, etc., et présentent en outre des caractéristiques telles qu'ils ne constituent aucun danger chimique pour les cultures, ainsi qu'une excellente efficacité en termes d'effets résiduels et de résistance aux précipitations.
PCT/JP1998/005816 1997-12-24 1998-12-22 Derives amides d'acide pyridyloxy(thio)alcanoique et bactericides a usage agricole ou horticole Ceased WO1999033810A1 (fr)

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Application Number Priority Date Filing Date Title
AU16859/99A AU1685999A (en) 1997-12-24 1998-12-22 Pyridyloxy(thio)alkanoic acid amide derivatives and agricultural/horticultural bactericides

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JP9/366367 1997-12-24
JP36636797 1997-12-24

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003042167A1 (fr) * 2001-11-16 2003-05-22 Syngenta Participations Ag Nouveaux derives phenethylamide de l'acide carboxylique $g(a)-oxygenes ou $g(a)-thioles
WO2003042168A1 (fr) * 2001-11-16 2003-05-22 Syngenta Participations Ag NOUVEAUX DERIVES PHENETHYLAMIDES D'ACIDE CARBOXYLIQUE α-OXYGENES OU α-THIOLES
WO2003048128A1 (fr) * 2001-12-06 2003-06-12 Syngenta Limited Derives d'amide d'acide pyridyloxyalcanoique utiles comme fongicides
WO2004047538A1 (fr) * 2002-11-26 2004-06-10 Syngenta Limited Oxyalkylamides de quinoline, d'isoquinoline et de quinazoline et leur utilisation comme fongicides
WO2004048337A1 (fr) * 2002-11-26 2004-06-10 Syngenta Limited Pyridyloxyalkylamides substitues et leur utilisation comme fongicides
WO2004108663A1 (fr) 2003-06-04 2004-12-16 Syngenta Limited Derives de n-alkynyle-2- (substitue aryloxy) alkylthioamide comme fongicides
US7271130B2 (en) 2002-11-26 2007-09-18 Syngenta Limited N-alkynyl-2-(substituted phenoxy) alkylamides and their use as fungicides
US7420090B2 (en) 2002-11-26 2008-09-02 Syngenta Limited Fungicides
WO2009087098A2 (fr) 2008-01-10 2009-07-16 Syngenta Participations Ag Fongicides
US11046658B2 (en) 2018-07-02 2021-06-29 Incyte Corporation Aminopyrazine derivatives as PI3K-γ inhibitors
US11926616B2 (en) 2018-03-08 2024-03-12 Incyte Corporation Aminopyrazine diol compounds as PI3K-γ inhibitors

Citations (2)

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US7700522B2 (en) 2001-11-16 2010-04-20 Syngenta Crop Protection, Inc. α-Oxygenated or α-thiolated carboxylic acid phenethylamide derivatives
US7601674B2 (en) 2001-11-16 2009-10-13 Syngenta Crop Protection, Inc. α-oxygenated or α-thiolated carboxylic acid phenethylamide derivatives
EP2314568A3 (fr) * 2001-11-16 2012-02-29 Syngenta Participations AG Nouveaux dérivés phénéthylamides d'acide carboxylique alpha-oxygenes ou alpha-thioles
EA011548B1 (ru) * 2001-11-16 2009-04-28 Зингента Партисипейшнс Аг НОВЫЕ ПРОИЗВОДНЫЕ ФЕНЕТИЛАМИДОВ α-КАРБОНОВЫХ ИЛИ α-ТИОКАРБОНОВЫХ КИСЛОТ
WO2003042167A1 (fr) * 2001-11-16 2003-05-22 Syngenta Participations Ag Nouveaux derives phenethylamide de l'acide carboxylique $g(a)-oxygenes ou $g(a)-thioles
US7166621B2 (en) 2001-12-06 2007-01-23 Syngenta Limited Pyridyloxyalkanoic acid amide derivatives useful as fungicides
WO2003048128A1 (fr) * 2001-12-06 2003-06-12 Syngenta Limited Derives d'amide d'acide pyridyloxyalcanoique utiles comme fongicides
WO2004048337A1 (fr) * 2002-11-26 2004-06-10 Syngenta Limited Pyridyloxyalkylamides substitues et leur utilisation comme fongicides
US7271130B2 (en) 2002-11-26 2007-09-18 Syngenta Limited N-alkynyl-2-(substituted phenoxy) alkylamides and their use as fungicides
CN100347160C (zh) * 2002-11-26 2007-11-07 辛根塔有限公司 喹啉－、异喹啉－和喹唑啉－氧烷基酰胺类化合物及其作为杀真菌剂的用途
RU2327687C2 (ru) * 2002-11-26 2008-06-27 Зингента Лимитед Хинолин-, изохинолин- и хиназолиноксиалкиламиды и их применение в качестве фунгицидов
US7420090B2 (en) 2002-11-26 2008-09-02 Syngenta Limited Fungicides
US7511151B2 (en) 2002-11-26 2009-03-31 Syngenta Limited Substituted pyridyloxyalkylamides and their use as fungicides
US7122672B2 (en) 2002-11-26 2006-10-17 Syngenta Limited Quinolin-, isoquinolin-, and quinazolin-oxyalkylamides and their use as fungicides
JP2006507339A (ja) * 2002-11-26 2006-03-02 シンジェンタ リミテッド キノリン、イソキノリン、及びキナゾリン−オキシアルキルアミド及び殺真菌剤としてのその使用
WO2004047538A1 (fr) * 2002-11-26 2004-06-10 Syngenta Limited Oxyalkylamides de quinoline, d'isoquinoline et de quinazoline et leur utilisation comme fongicides
RU2352559C2 (ru) * 2003-06-04 2009-04-20 Зингента Лимитед N-алкинил-2-(замещенные арилокси)-алкилтиоамидные производные как фунгициды
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US8067592B2 (en) 2003-06-04 2011-11-29 Syngenta Limited N-alkyny-2-(substituted aryloxy) alkylthioamine derivatives as fungicides
WO2004108663A1 (fr) 2003-06-04 2004-12-16 Syngenta Limited Derives de n-alkynyle-2- (substitue aryloxy) alkylthioamide comme fongicides
WO2009087098A3 (fr) * 2008-01-10 2009-10-01 Syngenta Participations Ag Fongicides
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US8415272B2 (en) 2008-01-10 2013-04-09 Syngenta Crop Protection Llc Quinoline derivatives and their use as fungicides
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