WO2003087058A1 - Nouveau compose d'oxime o-ether, procede de production et bactericide agricole ou horticole - Google Patents

Nouveau compose d'oxime o-ether, procede de production et bactericide agricole ou horticole Download PDF

Info

Publication number
WO2003087058A1
WO2003087058A1 PCT/JP2003/004747 JP0304747W WO03087058A1 WO 2003087058 A1 WO2003087058 A1 WO 2003087058A1 JP 0304747 W JP0304747 W JP 0304747W WO 03087058 A1 WO03087058 A1 WO 03087058A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
alkoxy
formula
alkyl
compound
Prior art date
Application number
PCT/JP2003/004747
Other languages
English (en)
Japanese (ja)
Inventor
Daisuke Ichinari
Akira Mitani
Hiroshi Sano
Hiroshi Hamamura
Takahiro Ando
Original Assignee
Nippon Soda Co.,Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Soda Co.,Ltd. filed Critical Nippon Soda Co.,Ltd.
Priority to AU2003235153A priority Critical patent/AU2003235153A1/en
Priority to JP2003584014A priority patent/JPWO2003087058A1/ja
Publication of WO2003087058A1 publication Critical patent/WO2003087058A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—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
    • 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
    • C07D213/61—Halogen atoms or nitro radicals

Definitions

  • Novel oxime 0-ether compound, production method and fungicide for agricultural and horticultural use Novel oxime 0-ether compound, production method and fungicide for agricultural and horticultural use
  • the present invention relates to a novel oxime 0-ether compound, a method for producing the same, and a fungicide for agricultural and horticultural use containing the compound as an active ingredient.
  • the oxime 0-ether compounds similar to the compounds of the present invention include, for example, EP 4754, EP 2488 88, W093 / 21 57, etc. Active compounds are described.
  • Japanese Patent Application Laid-Open No. Hei 9-13047 describes that an oxime 0-ether compound containing a compound represented by the following structural formula is useful as a fungicide.
  • WO O 1/3 456 688 lists oxime 0-ether compounds having a pyridyl group substituted at the 4-position with a fluorine atom in Table 1 as useful as fungicides. However, their production examples and biological test examples are not described. DISCLOSURE OF THE INVENTION:
  • An object of the present invention is to provide a novel oxime 0-ether compound which can be synthesized industrially advantageously, can be an effective fungicide having a certain effect and little phytotoxicity, and can be an excellent agricultural and horticultural fungicide.
  • an oxime ether compound in which the 4-position of the pyridine moiety is substituted with a fluorine atom has a particularly excellent control effect on agricultural and horticultural crop diseases as compared with known compounds. That is, the present invention has been completed.
  • the present invention provides a compound of the formula [I]
  • R 1 C 1 - 6 alkyl group, C 2 ⁇ 6 alkenyl, C 2 - 6 alkynyl group, 0 3-6 cycloalkyl group, an alkoxy group, ( ⁇ 1-6 alkylthio group, an amino group, Mono or di C 6 alkylamino group, C ⁇ 6 alkylcarbonyloxy group, Ci- 6 alkoxy C i alkyl group, C alkoxy Represents an alkoxy group, a nitro group, a cyano group, a hydroxy group or a halogen atom.
  • n represents an integer of 0 to 3, and when m is 2 or more, R 1 may be the same or different.
  • R 2 and R 3 are the same or different and represent a hydrogen atom or an alkyl group.
  • R 4 is an alkyl group, 3 to 6 cycloalkyl group, C 2 to alkenyl group 6 , C 2 to 6 alkynyl group, Ci to 6 alkoxy group, alkoxy Ci to 6 alkyl group, Ci to 6 alkoxy C ⁇ s alkoxy groups, C 3 ⁇ 6 cycloalkyl O alkoxy group, haloalkoxy groups, C 2 ⁇ 6 alkenyl Ruokishi groups, C 2 ⁇ 6 Arukiniruokishi groups, C alkylcarbonyl O alkoxy group, d ⁇ 6 alkoxide aryloxycarbonyl O carboxymethyl group, a mono- or di-C Bok 6 alkyl force Rubamoiruokishi group, C 1 alkylsulfonyl O carboxymethyl group, C!
  • ⁇ 6 haloalkylsulfonyl O alkoxy group Haroaruki Le group, C WINCH 6 alkylthio group, amino group, mono- or di-C ⁇ s Represents an alkylamino group, an alkylcarbonylamino group, a hydroxy group or a halogen atom.
  • n represents an integer of 0 to 5, and when n is 2 or more, R 4 may be the same or different, and the two R 4 form a 5- to 7-membered alkylene chain containing a hetero atom. May form a condensed ring of ) Oxime 0-ether conjugates or salts thereof represented by the formula (I), their production methods, novel production intermediates, and one or more of the oxime 0-ether compounds or salts thereof as an active ingredient Agricultural and horticultural fungicides.
  • R 1 is a 6- alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, t-butyl, pentyl and its isomers, hexyl and its isomers, vinyl, and propenyl , C 2 ⁇ 6 alkenyl groups such as isopropenyl,
  • Cyclopropyl, cyclopentyl, 1-methylstyrene cyclopentyl, cyclohexyl, 1-main to Chirushikuro have a substituent hexyl, etc. may C 3 be 1-6 cycloalkyl group, D alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy, t-butoxy,
  • Ci- 6 alkylthio groups such as methylthio, ethylthio, isopropylthio, and butylthio, amino groups,
  • Mono- or di-C-alkylamino groups such as methylamino, ethylamino, propylamino, dimethylamino, getylamino, dibupyramino, dibutylamino, ethylisopropylamino, etc.
  • C 6 alkyl carboxy groups such as acetoxy, propionyloxy, and bivaloyloxy;
  • C 6 alkoxy C 6 alkyl groups such as methoxymethyl, methoxyshethyl, ethoxymethyl, propoxymethyl, butoxymethyl,
  • Ci- 6 alkoxyalkoxy groups such as methoxymethoxy, methoxyethoxy, ethoxymethoxy, propoxymethoxy, butoxymethoxy, etc.
  • n represents an integer of 03.
  • R 1 may be the same or different.
  • RR 3 is the same or different,
  • heptyl a C 6 alkyl group such as pentyl and hexyl and its isomers its isomers, to - methyl, Echiru, propyl, isopropyl, heptyl, sec one heptyl, Isopuchiru, t.
  • R 4 is an alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, iso-butyl, t-butyl, pentyl and its isomers, hexyl and its isomers, cyclopropyl, cyclopentyl, 1-methyl cyclopentyl, cyclohexyl, C 4 ⁇ 6 cycloalkyl group cyclohexyl, etc., to 1 over main Chirushikuro,
  • Alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy, t-butoxy,
  • a C alkoxy C 6 alkyl group such as methoxymethyl, methoxethyl, ethoxymethyl, propoxymethyl, butoxymethyl,
  • Alkoxy alkoxy groups such as methoxy methoxy, methoxy ethoxy, ethoxy methoxy, propoxy methoxy, butoxy methoxy, etc.
  • C-alkyl carbonyl groups such as acetoxy, propionyloxy, and bivaloyloxy;
  • Ci- 6 alkoxycarbonyloxy groups such as methoxycarbonyloxy, ethoxycarbonyloxy and propoxycarbonyloxy;
  • Mono- or di-alkyl radicals such as methylcarbamoyloxy, dimethylcarbamoyloxy, ethylcarbamoyloxy, t-butylcarbamoyloxy, and C ⁇ 6 alkylsulfonyloxy such as methylsulfonyloxy and ethylsulfonyloxy Xy group,
  • haloalkylsulfonyloxy groups such as chloromethylsulfonyloxy, fluoromethylsulfonyloxy, trifluoromethylsulfonyloxy,
  • Chloromethyl Furuoromechiru, bromomethyl, dichloromethyl, Jifuruoromechiru, di- bromomethyl, trichloromethyl, triflumizole Ruo Russia methyl, tri promo methyl, Torikuroroe chill, torr full O Roe chill, pentaerythritol full O Roe C Bok 6 haloalkyl group chill like,
  • D- 6 alkylthio groups such as methylthio, ethylthio, and isopropylthio
  • Mono- or dialkylamino groups such as methylamino, ethylamino, propylamino, dimethylamino, getylamino, dibupyramino, dibutylamino and ethylisopropylamino;
  • C 6 alkylcarbonyl amino groups such as acetylamino, propionylamino, and vivaloylamino
  • n represents an integer of 0 to 3, and when m is 2 or more, R 1 may have the same or different, and in the two R 4, alkylene containing heteroatoms of such as methylene Nji O alkoxy group It may be a chain to form a 5- to 7-membered fused ring.
  • C i _ 6 alkyl group or a halogen atom R 4 is an alkyl group
  • C i - I ⁇ product is preferably an s alkoxy group or a halogen atom, in particular, but the 6-position are preferred.
  • the compound of the present invention can be produced as follows.
  • the compound represented by the formula [I] is prepared by mixing the compound represented by the formula [II] and the compound represented by the formula [III] or a salt thereof without a solvent, preferably in a solvent, at a reaction temperature of 0 to 15: It is obtained by stirring at 0 ° C for 10 minutes to 24 hours.
  • Solvents that can be used include alcohols such as ethanol and methanol; ethers such as getyl ether, tetrahydrofuran and dioxane; cellosolves such as methyl sorb and ethyl sorb; aromatic hydrocarbons such as benzene and toluene; and acetic acid. , Water, N, N-dimethylformamide, dimethylsulfoxide and the like. These solvents can be used alone or as a mixture of two or more solvents at various mixing ratios. This reaction does not necessarily require the presence of a catalyst, but the addition of an acid or base may significantly accelerate the reaction. Examples of the acid include inorganic acids such as sulfuric acid and hydrochloric acid, organic acids such as paratoluenesulfonic acid, and bases such as sodium acetate.
  • the acid include inorganic acids such as sulfuric acid and hydrochloric acid, organic acids such as paratoluenesulfonic acid, and bases such as sodium acetate
  • the compound represented by the formula [ ⁇ ] which is the starting material of the compound of the present invention, can be synthesized as follows.
  • the compound represented by the formula [W] or a salt thereof is obtained by stirring for 10 minutes to 24 hours at a reaction temperature of 0 to 150 ° C. in the absence of a solvent, preferably in a solvent, in the presence of a suitable oxidizing agent.
  • Solvents that can be used include ethers such as getyl ether, tetrahydrofuran, and dioxane; esters such as methyl acetate and ethyl acetate; aromatic hydrocarbons such as benzene and toluene; acetic acid; water; N, N-dimethylformamide And dimethyl sulfoxide. These solvents can be used alone or as a mixed solvent of two or more kinds in various mixing ratios.
  • the oxidizing agent that can be used include metal oxides such as manganese dioxide, and halogen oxides such as sodium dichlorite.
  • the oxyamines represented by the formula [m] can be produced as follows.
  • R 2 , R 3 , R 4 and n represent the same meaning as described above.
  • L represents a halogen atom such as chlorine, bromine or iodine, a methanesulfonyloxy group, a paratoluenesulfonyloxy group or the like. Represents a leaving group.
  • the compound represented by the formula [V] is reacted with N-hydroxyphthalimide in the presence of a base such as triethylamine to convert the compound into the compound represented by the formula [VI], and further reacted with hydrazine to give the compound represented by the formula [V].
  • a benzyloxyamine represented by the formula [III] can be produced.
  • the compound represented by the formula [V-1] in which R 2 and R 3 are hydrogen atoms and L is a halogen atom is produced as follows. be able to.
  • R 4 and n represent the same meaning as described above, and L 1 represents a halogen atom such as chlorine, bromine, and iodine.
  • the compound represented by the formula [VII] may be added to a halogenated succinimide such as N-chlorosuccinimide (NCS), N-butyl succinimide (NBS), or N-n-succinimide (NIS). Is reacted under light irradiation to synthesize a compound represented by the formula [V-1].
  • a halogenated succinimide such as N-chlorosuccinimide (NCS), N-butyl succinimide (NBS), or N-n-succinimide (NIS).
  • R 4 , n, and L represent the same meaning as described above, and W represents a halogen atom such as chlorine, a hydroxy group, a hydrogen atom, or a lower alkoxy group.
  • a ketone or aldehyde represented by the formula [X] is reacted with a Grignard reagent represented by the formula [XI] to induce an alcohol represented by the formula [XII].
  • a halogenating agent such as chloride
  • a sulfonyl halide such as methanesulfonyl chloride
  • the salt of the compound represented by the formula [I] can be obtained by reacting the compound represented by the formula [I] with an inorganic acid or an organic acid in a suitable solvent.
  • the oxime moiety of the compound of the present invention has isomers, and these isomers are included in the scope of the present invention.
  • the structure of the compound of the present invention is determined by NMR, mass spectrum and the like.
  • Table 1 shows typical examples of the compounds of the present invention including the above Examples. / Saichi
  • Table 2 shows typical examples of the compounds of the present invention including the above Examples.
  • the compound represented by the formula [1] or a salt thereof of the present invention can be used for a wide variety of filamentous fungi, for example, ascomycetes (COomv cetes). Ascomycetes (Ascomvcetes). omy cetes) and has excellent bactericidal activity against bacteria belonging to the basidiomycetes (Basidi omy cetes).
  • composition containing the compound of the present invention as an active ingredient is used for controlling various diseases that occur during the cultivation of agricultural and horticultural crops including flowers, turf, and grass by seed treatment, foliage application, soil application, or water application. be able to.
  • Laccasey (My cos p aer e l l a a r a c hi i d i s)
  • Leaf mold (C l a do s p o r i um f u 1 v um)
  • Powdery mildew (Soha e r o t he c a a p h a n i s)
  • Rin Tsudonko (Podo s pha e r a 1 e u c o t r i c n a)
  • Leaf spot (Co ch l i o b o 1 u s s a t i v u s)
  • Powdery mildew (Erysiphegramini.inisf.sp.triticci) Red snow rot (Micronnectriie1 1 aniivaliis)
  • Sesame leaf blight (Co ch l i obo l u s n i yab e anu s), octopus sclerotium sclerotium (S c l e r o t i n i a s c l e r o t i o r um)
  • Powdery mildew (Ery s i p h e c i c ho r a c e a rum)
  • Bentgrass snow rot Bacterial sclerotium (S c l e ro t i n i a b o r e a 1 is),
  • Orchardgrass powdery mildew (Ery si ph egraminis), Soybean purpura (Cercosporakikuchii),
  • Potato and Tomato Blight (Phv toph thora ain fes t ans.
  • Kiyuribe and Byung P s eudop e r ono s por a cub e n s is
  • It can be used for pest control.
  • the compound of the present invention is a drug having an excellent bactericidal effect not only on pathogenic bacteria sensitive to such drugs but also on resistant bacteria.
  • the compound of the present invention is also effective against gray mold fungus (Botryticinsinea) which is resistant to dicarboximide fungicides (for example, vinclozolin, procymidone, iprodione) as well as susceptible bacteria.
  • gray mold fungus Botryticinsinea
  • dicarboximide fungicides for example, vinclozolin, procymidone, iprodione
  • the compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to aquatic organisms such as ship bottoms and fish nets.
  • the fungicide of the present invention contains one or more of the compounds of the present invention as an active ingredient.
  • the obtained compound of the present invention when the obtained compound of the present invention is actually applied, it can be used in a pure form without adding other components, and can be in the form of a general pesticide for use as a pesticide, i.e. , Powder, emulsion, 7j solvent, suspension, flowable and the like.
  • a general pesticide for use as a pesticide i.e. , Powder, emulsion, 7j solvent, suspension, flowable and the like.
  • Additives and carriers that can be added to the pesticide formulation include, for solid formulations, plant powders such as soybean flour and wheat flour, diatomaceous earth, apatite, gypsum, talc, bentonite, and no. Mineral fine powders such as irophyllite and clay, and organic and inorganic compounds such as sodium benzoate, urea and sodium sulfate are used.
  • petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone , Mineral oil, vegetable oil, water and the like can be used as the solvent.
  • a surfactant may be added as necessary.
  • the surfactant include alkyl phenyl ether to which polyoxyethylene is added, alkyl ether to which polyoxyethylene is added, higher fatty acid ester to which polyoxyethylene is added, higher sorbitan fatty acid ester to which polyoxethylene is added, and polyoxyethylene.
  • Nonionic surfactants such as tristyryl phenyl ether added with oxyethylene, sulfates of alkyl phenyl ether added with polyoxyethylene, alkyl benzene sulfonates, sulfates of higher alcohols, alkyl Examples include naphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkylnaphthalene sulfonates, and copolymers of isobutylene monomaleic anhydride.
  • the amount of the active ingredient is usually preferably 0.01 to 90% by weight based on the whole composition (formulation). And more preferably 0.05 to 85% by weight.
  • the fungicidal composition of the present invention thus formulated is applied to a plant, a seed, a water surface or soil as it is or after being diluted with water or the like.
  • Water-dispersible powders, emulsions and flowables are used as a suspension or emulsion by diluting them to a predetermined concentration with water, and powders and granules are used as they are sprayed on plants.
  • the application rate varies depending on the weather conditions, formulation, application time, application method, application site, target disease, target crop, etc., but it is usually 1 to 1000 g, preferably 10 to 10 g, as active compound per hectare. ⁇ 100 g.
  • the application concentration is 1 to 1000 ppm, preferably 10 to 250 ppm.
  • the compound of the present invention is sufficiently effective alone, but it can also be used in combination with one or more of various fungicides, insecticides and acaricides, or synergists.
  • various fungicides, insecticides, acaricides, and plant growth regulators that can be used by mixing with the compound of the present invention are shown below.
  • Copper agents basic copper chloride, basic copper sulfate, and the like.
  • Sulfur agents Sulfur agents; thiuram, zineb, maneb, mancozeb, ziram, provevineb, polycarbamate, etc.
  • Organophosphorus agents IBP, EDDP, triclofosmethyl, pyrazophos, Josetyl and the like.
  • Benzimidazole agents thiophane-methyl, benomyl, carbendazim, thiabendazole and the like.
  • Dicarboximide agents iprodione, procymidone, vinclozolin, fluorimide and the like.
  • Carboxamide agents oxycarboxin, mepronisole, flutranil, teclophthalam, triclamide, pencyclone and the like.
  • Asylalanine preparations metalaxyl, oxadixyl, furalaxyl and the like.
  • Methoxyacrylates kresoxim-methyl, azoxystrobin, metominost oral bottles and the like.
  • Anilinovirimidine andpurine, mepanipyrim, pyrimethanil, diprodinil and the like.
  • SB I agent Triadimefon, Triadimenol, Bite / Tanol, Microbutanil, Hexaconazole, Propiconazole, Triflumizole, Prochloraz, ⁇ Frazoet, Funarimol, Pyrifenox, Triforin, Flusilazole, Etaconazole , Zik Mouth butrazole, fluotrimazole, flutriafon, penconazole, diniconazole, imazalil, tridemorph, phenylpropimorph, pthiobate, epoxyconazole, metconazole, etc.
  • Antibiotics polyoxin, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate and the like.
  • Cyanophos isoxathion, pyridaf Xinthion, hosalon, methidathion, sulprophos, chlorfenvinphos, tetrachlorovinphos, dimethylvinphos, prochaphos, isofenphos, ethylthiomethone, profenophos, piraclophos, monocrotophos, azidinphos-methyl, aldicarb Methomyl, Chozikarb, Carpofuran, Carbosulfan, Benfracarb, Fratiocarp, Robokisuru, B P M C MTM C M I P C, Kanorebariru, pyridinium Mika one blanking, E Chio Fen Culp, Fueno Kishikarupu like.
  • Permethrin Permethrin, Cypermethrin, Deltamethrin, Fuemperate, Fuemptrin, Pyrethrin, Aresulin, Tetramethrin, Resmethrin, Dimethrin, Propasulin, Phenotrin, Protrin, Fulvalinate, Cyfluthrin, Cyhalothrin, Flucitrine, Xetoprofic Prothrin, trolamethrin, silafluofyun, brofenprox, acrinasulin, etc.
  • Nematicides fenamiphos, phosthiazate and the like.
  • Plant growth regulator Plant growth regulator
  • Gibberellins eg, gibberellin A3, gibberellin A4, gibberellin A7 I ⁇ ⁇ , ⁇ A ⁇ and the like.
  • Example 4 wettable powder
  • Example 9 wettable powder for granules
  • the above mixture is uniformly mixed and finely ground, and then an appropriate amount of water is added and kneaded to form a clay. If the clay-like material is granulated and dried, the active ingredient is a 40% water dispersible granule. Get.
  • Test Examples show that the compound of the present invention is useful as an active ingredient of various plant disease controlling agents.
  • the control effect was determined by visually observing the disease state of the test plant at the time of the survey, that is, the degree of the growth of the bacterial spots on the leaves, stems, etc., and comparing it with that of no treatment.
  • compound A (Table 1, compound number 262) represented by the following structural formula described in WO 00Z07744 was used.
  • Test Example 1 Test for controlling common bean gray mold
  • the flowers of the kidney beans (variety “Nagauzura”) cultivated in the seedling raising bat were excised, and immersed in a medicinal solution adjusted to a concentration of 200 Ppm of the active ingredient of the compound of the present invention. After immersion, it was air-dried at room temperature and spray-inoculated with kidney bean fungus (Botrytiscinnare). The inoculated flowers were placed on untreated leaf leaves and kept in a high-humidity constant temperature room (20 ° C) where light and dark were repeated every 12 hours for 7 days. The lesion diameter on leaves was compared with that of untreated leaves, and the control value was determined. As a result, the following compounds showed 100% control value. The control value of Compound A used for comparison was 100%. The compound numbers correspond to the compound numbers in Tables 1 to 3.
  • the first true leaf of a kidney bean (variety “Nagauzura”) cultivated in a pot was sprayed with a chemical solution prepared by adjusting an emulsion of the compound of the present invention 1-62, 1-72 or comparative compound A to a concentration of 200 ppm of the active ingredient. .
  • the kidney pot was placed in a glass greenhouse. Seven days later, the first true leaf was cut off, and a pink flower vase inoculated with a pink gray mold fungus (Botrytsiscinerea) in advance was placed on the leaf. After being kept in a high humidity constant temperature room (20 ° C) for 5 days, the diameter of lesions formed on the leaves was compared with that of untreated leaves, and the control value was determined.
  • the compounds of the present invention 1-62 and 1-72 showed a control value of 100%, whereas the comparative compound A showed 36%. From these results, it was found that the compound of the present invention is a compound having significantly better activity in practical use than the known compound.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un nouveau composé d'oxime O-éther représenté par la formule (I), un procédé de production dudit composé et un bactéricide agricole ou horticole contenant le composé comme ingrédient actif. Dans la formule (I), R1 représente C1-6 alkyle, C2-6 alcényle, C2-6 alcynyle, C3-6 cycloalkyle, C1-6 alcoxy, C1-6 alkylthio, amino, etc.; m représente un nombre entier compris entre 0 et 3; R2 et R3 sont identiques ou différents et représentent chacun hydrogène ou C1-6 alkyle; et R4 représente C1-6 alkyle, C3-6 cycloalkyle, C2-6 alcényle, C2-6 alcynyle, C1-6 alcoxy, (C1-6 alcoxy) C1-6 alkyle, etc.
PCT/JP2003/004747 2002-04-15 2003-04-15 Nouveau compose d'oxime o-ether, procede de production et bactericide agricole ou horticole WO2003087058A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2003235153A AU2003235153A1 (en) 2002-04-15 2003-04-15 Novel oxime o-ether compound, production process, and agricultural or horticultural bactericide
JP2003584014A JPWO2003087058A1 (ja) 2002-04-15 2003-04-15 新規なオキシムｏ−エーテル化合物、製造方法及び農園芸用殺菌剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2002-111592 2002-04-15
JP2002111592 2002-04-15

Publications (1)

Publication Number Publication Date
WO2003087058A1 true WO2003087058A1 (fr) 2003-10-23

Family

ID=29243282

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2003/004747 WO2003087058A1 (fr) 2002-04-15 2003-04-15 Nouveau compose d'oxime o-ether, procede de production et bactericide agricole ou horticole

Country Status (5)

Country Link
JP (1) JPWO2003087058A1 (fr)
AR (1) AR039426A1 (fr)
AU (1) AU2003235153A1 (fr)
TW (1) TW200306154A (fr)
WO (1) WO2003087058A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07196617A (ja) * 1993-12-28 1995-08-01 Nippon Soda Co Ltd ケトンオキシムエーテル誘導体、その製造方法及び農園芸用殺菌剤
JPH093047A (ja) * 1995-06-21 1997-01-07 Nippon Soda Co Ltd ケトンオキシムエーテル誘導体、その製造方法及び農園芸用殺菌剤
WO2001034568A1 (fr) * 1999-11-05 2001-05-17 Nippon Soda Co., Ltd. Composes oxime o-ether et fongicides utiles dans l'agriculture et l'horticulture
WO2002064566A1 (fr) * 2001-02-14 2002-08-22 Nippon Soda Co.,Ltd. Composes d'oxime o-ether et fongicides a usage agricole et horticole
WO2002066434A1 (fr) * 2001-02-20 2002-08-29 Nippon Soda Co.,Ltd. Compose d'oximether et bactericides agricole et horticoles

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07196617A (ja) * 1993-12-28 1995-08-01 Nippon Soda Co Ltd ケトンオキシムエーテル誘導体、その製造方法及び農園芸用殺菌剤
JPH093047A (ja) * 1995-06-21 1997-01-07 Nippon Soda Co Ltd ケトンオキシムエーテル誘導体、その製造方法及び農園芸用殺菌剤
WO2001034568A1 (fr) * 1999-11-05 2001-05-17 Nippon Soda Co., Ltd. Composes oxime o-ether et fongicides utiles dans l'agriculture et l'horticulture
WO2002064566A1 (fr) * 2001-02-14 2002-08-22 Nippon Soda Co.,Ltd. Composes d'oxime o-ether et fongicides a usage agricole et horticole
WO2002066434A1 (fr) * 2001-02-20 2002-08-29 Nippon Soda Co.,Ltd. Compose d'oximether et bactericides agricole et horticoles

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BANKS R.E. ET AL.: "Heterocyclic polyfluoro compounds. XXI. Synthesis of 2-substituted tetrafluoropyridines. 2,3,4,5-tetrafluoro-6-methoxypyridine and 3,4,5,6-tetrafluoropyridine-2-carboxaldehyde, -2-carboxylic acid, -2-carboxamide and -2-carbonitrile", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY (1972-1999), no. 20, 1974, pages 2367 - 2369, XP002971009 *
BROOKE G.M., FERGUSON J.A.K.J.: "Reactions of polyfluoroarenols and -heteroarenols with activated dimethyl sulfoxide. Facile (2,3)-sigmatropic rearrangement reactions giving dearomatized products", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY (1972-1999), no. 9, 1987, pages 2091 - 2097, XP008027004 *

Also Published As

Publication number Publication date
JPWO2003087058A1 (ja) 2005-08-18
AU2003235153A1 (en) 2003-10-27
TW200306154A (en) 2003-11-16
AR039426A1 (es) 2005-02-16

Similar Documents

Publication Publication Date Title
JPH10324687A (ja) ピロール化合物、製法および農園芸用殺菌剤
WO1992016527A1 (fr) Derive de pyridine substitue en position 2, sa production, et bactericide d'agrohorticulture
WO2019165798A1 (fr) Composé de thioéther de pyrimidine d'hydrocarbure insaturé, son procédé de préparation et son utilisation
JP4726373B2 (ja) オキシムｏ−エーテル化合物および農園芸用殺菌剤
WO1997011943A1 (fr) Composes de pyrazole, procede de preparation et bactericide agrohorticole
JP4387950B2 (ja) ヒドラジン誘導体、製造中間体および農園芸用殺菌剤および殺虫剤
WO2002066434A1 (fr) Compose d'oximether et bactericides agricole et horticoles
WO2002064566A1 (fr) Composes d'oxime o-ether et fongicides a usage agricole et horticole
WO1999002518A1 (fr) Composes pyridyltriazole, procedes de production associes, et germicides agricoles et horticoles
JPH08193067A (ja) ピラゾール化合物、製法、農園芸用殺菌剤および殺虫・殺ダニ剤
JP4170073B2 (ja) オキシアミン誘導体、製造中間体及び農園芸用殺菌剤
WO2001068589A1 (fr) Composes acrylonitrile et agents pesticides
WO1996017841A1 (fr) Composes de pyridylpyrrole, processus de production et bactericide agro-horticole
JPWO2003087056A1 (ja) 新規オキシムｏ−エーテル化合物、製造方法及び農園芸用殺菌剤
WO2003087058A1 (fr) Nouveau compose d'oxime o-ether, procede de production et bactericide agricole ou horticole
JP2009062277A (ja) ベンゾイソチアゾリン化合物及び有害生物防除剤
JPH09124640A (ja) ピリジルイミダゾール化合物、製法および農園芸用殺菌剤
CN105777640B (zh) 一种吡唑环己二醇醚类化合物及其应用
WO1999044993A1 (fr) Compose a base d'acryronitrile, son procede de production et agent de lutte contre les ravageurs renfermant ce compose
JPH08217754A (ja) イミダゾール化合物、殺虫・殺ダニ剤及び農園芸用殺菌剤
WO2004011445A1 (fr) Derive d'aminosalicylamide, procede de production de celui-ci et pesticide agri-horticole
WO1999040076A1 (fr) Composes de thiazole, procede de production, agent antiparasitaire et agent antifongique
JP2006327973A (ja) アリール複素環誘導体および農園芸用殺菌剤
JPH1067730A (ja) 新規なベンズアミドオキシム誘導体、その製法及び農園芸用殺菌剤
JPH11269154A (ja) ピリミジン化合物、その製造法および有害生物防除剤

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NI NO NZ OM PH PL PT RO RU SC SD SE SG SK SL TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2003584014

Country of ref document: JP

122 Ep: pct application non-entry in european phase