WO1999040076A1 - Composes de thiazole, procede de production, agent antiparasitaire et agent antifongique - Google Patents

Composes de thiazole, procede de production, agent antiparasitaire et agent antifongique Download PDF

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Publication number
WO1999040076A1
WO1999040076A1 PCT/JP1999/000473 JP9900473W WO9940076A1 WO 1999040076 A1 WO1999040076 A1 WO 1999040076A1 JP 9900473 W JP9900473 W JP 9900473W WO 9940076 A1 WO9940076 A1 WO 9940076A1
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Prior art keywords
group
compound
het
general formula
alkyl
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PCT/JP1999/000473
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English (en)
Japanese (ja)
Inventor
Teruyuki Iihama
Masahiro Miyazawa
Osamu Miyahara
Shinji Marumo
Shinsuke Sano
Hiroshi Hamamura
Chinami Yokota
Masahiro Kawaguchi
Hidemitsu Takahashi
Masae Takagi
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Nippon Soda Co., Ltd.
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Application filed by Nippon Soda Co., Ltd. filed Critical Nippon Soda Co., Ltd.
Priority to AU22989/99A priority Critical patent/AU2298999A/en
Publication of WO1999040076A1 publication Critical patent/WO1999040076A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/34—Oxygen atoms

Definitions

  • the present invention relates to a novel thiazole compound, a production method, and a pesticidal and antifungal agent containing them as an active ingredient.
  • Compounds similar to the compound of the present invention include, for example, phenyl monomethoxycarbamate in WO96Z0125, WO96 / 0128, W0963 / 34777, and the like. It is described that the compounds and phenylacrylic acid compounds are useful as agricultural and horticultural fungicides, insecticides and acaricides. However, these documents do not describe a compound having a heteroylthiazolyloxy (thio) methyl group as a substituent of a phenyl group as in the compound of the present invention.
  • W09 5/3 4 5 2 6 discloses a general formula (B)
  • R ′ represents a heterocyclic group containing a thiazole group.
  • An object of the present invention is to provide a novel thiazole compound which can be used as a pesticidal agent o which is surely effective and can be used safely, and a method for producing the same.
  • the present invention provides a compound represented by the general formula (1)
  • R 1 and R 2 each independently represent a hydrogen atom, a halogen atom or a ds alkyl group
  • X 0, S, SO, and S 0 2
  • Y represents one of the following groups (a), (b) and (c).
  • Het represents a heterocyclic group optionally substituted with Z. -Where the heterocyclic group is a phenyl, furyl, pyridyl, thiazolyl, pyrimidinyl or birazinyl group;
  • Z represents a cyano group, a hydroxy group, a halogen atom, a C alkyl group, a dalkenyl group, a d alkynyl group, a C i alkoxy group, a C!
  • Het may be substituted with a plurality of the same or different Z.
  • R 1 and R 2 each independently represent a halogen atom such as fluorine, chlorine, bromine, iodine,
  • Y represents any one of the groups shown in the above (a), (b) and (c).
  • Het represents a 2-phenyl, 3-phenyl, 2-phenyl, 2-furyl, 3-furyl group which may have a plurality of the same or different substituents Z at any position of the heterocyclic ring.
  • 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-pyrimidinyl, 4-pyrimidinyl, 5 Represents a heterocyclic group such as a pyrimidinyl group, a 2-birazinyl group, or a 3-birazinyl group.
  • the substituent Z of the heterocyclic ring is a cyano group, a hydroxy group,
  • Halogen atoms such as fluorine, chlorine, and bromine
  • C alkynyl groups such as ethynyl, 1-propynyl, 1 monobutynyl, and 2-butynyl groups;
  • alkylthio groups such as methylthio, ethylthio, propylthio, isopropylthio, and butylthio groups;
  • C1-6 alkylsulfinyl groups such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, and butylsulfinyl groups; C! -6 alkylsulfonyl group,
  • 1-6 haloalkyl groups such as fluoromethyl, 1-fluoroethyl, 2-fluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, penfluorofluorethyl, etc.
  • a hydroxyminomethyl group such as a 1-hydroxyminoethyl group
  • Ci-B alkoxyimino ⁇ alkyl groups such as methoxyiminomethyl, 1-methoxyiminoethyl, and 2-ethoxyiminoethyl groups;
  • a substituted benzyl group such as a rubamoyl group, and-which may have a substituent at any position of the benzene ring (benzyl, methylbenzyl, ⁇ , ⁇ -dimethylpentyl);
  • a phenyl group which may have a substituent at any position of the benzene ring, and a substituent which may have a substituent at any position of the benzene ring (benzyloxy, permethylbenzyloxy, a, ⁇ — Represents a substituted benzyloxy group such as dimethylbenzyloxy).
  • substituents which may have a substituent (a phenyl group, a benzyl group, a phenoxy group and a benzyloxy group) include:
  • Halogen atoms such as chlorine, bromine and fluorine
  • D- 6 alkoxy groups such as methoxy and ethoxy groups
  • a C ⁇ 6 haloalkyl group such as a trifluoromethyl group
  • Alkylthio groups such as methylthio and ethylthio groups
  • phenyl group, benzyl group, phenoxy group and benzyloxy group may have the same or different plural substituents.
  • the salt of the compound of the present invention is not particularly limited as long as it is an agriculturally and horticulturally and pharmaceutically acceptable salt.
  • salts of alkali metals such as sodium, calcium and lithium, salts of alkaline earth metals such as calcium and magnesium, and metals such as transition metals such as nickel, cobalt, manganese, copper and zinc.
  • examples thereof include salts, salts of mineral acids such as hydrochloric acid and sulfuric acid, and salts of organic acids such as methanesulfonic acid, P-toluenesulfonic acid, and oxalic acid.
  • the compound of the present invention can be produced by the following method. (Production method 1)
  • R 1, R 2, Y and H et represents the same meaning as defined above, X 'represents 0 or S, L is chlorine, bromine, CH 3 S 0 2 0 group, Bok Shiruokishi group Represents a leaving group such as.)
  • This method comprises reacting a compound represented by the general formula (2) with a compound represented by the general formula (3) in an inert solvent in the presence of a base at a reaction temperature of 50 to 150 ° C, The reaction is carried out preferably at 0 to 100 for 1 to 48 hours to produce the compound represented by the general formula (1-1).
  • Solvents that can be used in this reaction include benzene, toluene ⁇ ⁇ aromatic hydrocarbons, ethers such as dimethyl ether, tetrahydrofuran (THF), acetonitril, N, N-dimethyl Examples thereof include formamide (DMF) and dimethyl sulfoxide (DMS 0), and preferred examples include DMF and acetonitrile.
  • Examples of the base that can be used in the reaction include inorganic bases such as sodium hydride, potassium carbonate, potassium hydroxide, and sodium hydroxide, and triethylamine, 1,8-diazabicyclo [5.4.0].
  • examples thereof include amides such as dendecene-17 (DBU), and metal salts such as silver oxide (Ag 20 ) and silver carbonate.
  • a compound in which X is SO or S 02 is converted to a corresponding compound in which X is S by a known oxidation reaction using an oxidizing agent such as hydrogen peroxide, peracetic acid, or m-chloroperbenzoic acid.
  • an oxidizing agent such as hydrogen peroxide, peracetic acid, or m-chloroperbenzoic acid.
  • a compound represented by the general formula (4) is mixed with a formate such as methyl formate in a solvent or without solvent in the presence of a base at a reaction temperature of 50 to 100 ° C, preferably.
  • the reaction is carried out at 0 to 50 for 1 to 48 hours to obtain an intermediate (5).
  • Solvents that can be used in this reaction include aromatic hydrocarbons such as benzene and toluene, ethers such as dimethyl ether, THF, and dimethoxetane (DME), acetonitril, DMF, and the like. DMS O and the like. Of these, the use of DMF or DME is preferred.
  • examples of the base that can be used in the reaction include inorganic bases such as sodium hydride and hydride hydride.
  • the compound represented by the general formula (1-2) can be obtained by subjecting the obtained intermediate (5) to a usual methylation reaction using a methylating agent such as dimethyl sulfate or methyl iodide. .
  • the compound (1) of the present invention includes, for example, a compound wherein Y is (a): , Z isomers, also as a substituent on the heterocyclic ring, human Dorokishii Mi Roh ds alkyl le group, C, - 6 Arukokishii Mi Bruno C -!
  • Y is (a):
  • Z isomers, also as a substituent on the heterocyclic ring, human Dorokishii Mi Roh ds alkyl le group, C, - 6 Arukokishii Mi Bruno C -!
  • the i E and Z isomers of the amino moiety may exist, respectively, and all such forms are included in the scope of the present invention.
  • the target product after the completion of the reaction, the target product can be obtained by performing ordinary post-treatment.
  • the structure of the compound of the present invention can be determined from IR, NMR, and Mass spectrum.
  • Table 1 shows examples of the compounds included in the present invention.
  • the abbreviations in the table have the following meanings.
  • the compounds in Table 1 are compounds represented by the following structural formulas.
  • 2-CH 2 Ph-5-PM HH 2-CH 2 Ph-4-TZ HH (Pest control agent)
  • the compound of the present invention thus obtained is actually used as an agricultural and horticultural fungicide, insecticide, acaricide, antifungal, etc. It can be used in any form.
  • the form that general agricultural medicines can take for the purpose of using them as agricultural chemicals and pharmaceuticals i.e., solid preparations such as granules and powders, liquid preparations such as wettable powders, emulsions, aqueous solvents, suspensions, and floors Etc. can be used after being formulated.
  • plant powders such as soybean grains and flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, and other mineral powders, sodium benzoate, urea, Additives and carriers such as organic and inorganic compounds such as sodium sulfate can be used.
  • petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, DMF, DMSO, alcohol, acetate, trichloroethylene, methyl iso- Petil ketone, mineral oil, vegetable oil, water, etc. can be used as the solvent.
  • a surfactant can be added to these preparations as needed.
  • the surfactant include, but are not limited to, alkyl phenyl ether to which polyoxyethylene is added, alkyl ether to which polyoxetylene is added, higher fatty acid ester to which polyoxetylene is added, Non-ionic surfactants such as sorbitan higher fatty acid ester to which polyoxetylene is added, tristylphenyl ether to which polyoxetylene is added, and alkylphenol to which polyoxetylene is added.
  • liquid preparations such as wettable powders, emulsions, suspensions, and flowables
  • solid preparations such as powders and granules are prepared by diluting with water to the specified concentration as suspensions or emulsions. In the case of, it can be used as it is.
  • the composition of the compound (1) of the present invention which is an active ingredient
  • the content in the composition is preferably from 0.01 to 90% by weight, more preferably from 0.05 to 85% by weight.
  • the compound of the present invention can be used for a wide variety of filamentous fungi, such as algae (00 my cetes), ascomycetes ( ⁇ ), fungi (Asco my cetes), incomplete fungi (Deutero my cetes), It has excellent bactericidal activity against bacteria belonging to B. asidio mycetes).
  • the composition containing the compound of the present invention as an active ingredient can be used for controlling various diseases that occur during the cultivation of agricultural and horticultural crops including flowers, turf, and pasture, by seed treatment, foliage application, soil application or water application. Can be.
  • Eye spot disease Pseudocercosporel la herpotr ichoides
  • Fusarium wilt Fusarium wilt (Leptosphaer ia nodorum)
  • Powdery mildew Erys iphe gaminis f. Sp.t r i t i c i
  • Red snow rot Monographel la nival is
  • Potato blight Plant blight
  • Penile disease (Moj i 1 inia m l i)
  • Anthracnose Cold letotr ichum theae-sinensis
  • Kankitsu souka disease El is inoe fawce ⁇ ti
  • It can be used for pest control.
  • the compound of the present invention is an agent having an excellent bactericidal effect not only on sensitivity but also on pathogenic bacteria resistant to benzimidazole agents and dicarboximide agents.
  • the compound of the present invention shows an excellent control effect on gray mold which is generally inferior to the control effect of acrylic acid compounds.
  • the compound of the present invention can be used for controlling agricultural pests, sanitary pests, storage pests, clothing pests, house pests, and the like, and has an insecticidal, nymphal, larvicidal, and ovicidal action.
  • the following are typical examples.
  • Lepidopteran insect pests for example, Hasmontoto, Totoga, Tamanayaga, Aomushi, Tamanaginba, Konaga, Tyano Kokamakumaki, Tiyahamaki, Momoshingiga, Nashihime Shinki, Mikanhamogriga, Chiyanoga, Kigamo, Kigamo, Kigamo, Kigamoga Bivalve corn borer, squirrel, squirrel, squirrel stalk, squirrel stalk, sclerophyllum, heliotis, helicovelpa, agrotis, iga, kodlinga, scorpion .
  • Hemiptera pests for example, peach aphid, peter aphid, saccharomyces aphid, barley vilae aphid, scorpion beetle, stag beetle, yano nekada, kukonakayara, shikonashi-nami-bashi, shikoku-nashi-nami , Himetobin power, Sage roonka, Tsumaguroyoko etc.
  • Coleoptera pests for example, Lepidoptera criscivore, Leaf beetle, Colorado beetle, Rice beetle, Rice beetle, Kokuzumushi, Azukizomushi, Bean beetle, Scarabae beetle, Giabrotica, Tobacco beetle, Hirata beetle, Yellow moss Agriotis spp.
  • Diptera insect pests for example, house flies, oak blows, sentinella flies, perilla flies, mycophores, pods, rice flies, flies, flies, stag flies, mosquitoes, and mosquitoes.
  • Pterodactyl pests for example, southern thistle ⁇ ,.
  • Hymenopteran pests such as house ants, Japanese hornets, and power wasps.
  • Orthoptera pests for example, Japanese cockroaches, cockroaches, black cockroaches, and tosamaba.
  • Isopterid pests for example, house termites and mountain termites.
  • Lepidopteran insects for example, rat flea, lice, etc.
  • Pests for example, human louse, etc., mites, for example, Nami-hadani, Kanzahada-ni, Rutani mite, Lingo spider mite
  • Plant-parasitic nematodes for example, sweet potato nematode, Negusaresenchyu II, soybean ciscentium, rice singarecentenyu, matsunosaicentiyu, and the like.
  • the compound of the present invention is an agent having an excellent insecticidal and acaricidal effect against not only susceptible strains but also pests of organic phosphorus, carbamate or pyrethroid-resistant strains and mites of acaricide-resistant strains.
  • the compound of the present invention has low phytotoxicity, low toxicity to fish poisons and warm-blooded animals, and is a highly safe drug.
  • the compound of the present invention has an excellent growth inhibitory effect against human parasitic fungi such as Trichophyton mentagrophytes, and can be used as a medical antifungal agent. You.
  • the compound of the present invention has an antiprotozoal activity against Plasmodium malaria (Plasmodium), and can be used as an antimalarial drug.
  • 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 compound of the present invention by mixing the compound of the present invention into paints, fibers, and the like, it can be used as an antibacterial and antifungal agent for walls and bathtubs, or shoes and clothes.
  • the compound of the present invention When the compound of the present invention is used as an agricultural and horticultural fungicide, insecticide or acaricide, it exhibits sufficient efficacy even when used alone, but is used in combination with at least one of various fungicides, insecticides, acaricides or synergists. They can be used in combination.
  • Fungicides, insecticides, acaricides, nematicides, and plant growth regulators that can be used by mixing with the compound of the present invention include the following.
  • Organophosphorus and carbamate pesticides Phenthione, phenytrothion, diazinon, chlorpyrifos, EP; nomidothion, pentitol, dimethate, formotion, malathone, trichlorfon, thiomethone, phosmet, Dichlorvos, aseptate, EPBP, methyl parathion, oxydimethonmethyl, ethione, salicion, cyanophos, isoxathion, pyridafenthion, hosalon, methidathione, sulprophos, chlorphenvirbinphos, tetraclomilphos , Propaphos, isofenphos, ethylthiomethone, profenophos, pyraclophos, monocrotophos, azinphosmethyl, aldicarb, mesomezole, thiodicarb, carbofuran, carbosulfan, Benfracalp, Fratio
  • Plant growth regulator Plant growth regulator
  • Jibereri emissions such Jibereri down A 3, Jibereri emissions A 4, Jibereri emissions A 7), IAA, NAA and the like.
  • the antifungal agent for medical use of the present invention is approved as a mode of administration of the compound of the general formula (1) or a pharmaceutically acceptable complex thereof in a pure form or a drug having similar utility. It can be administered in any manner.
  • a pharmaceutically acceptable antifungal composition will comprise one or more of the compounds of general formula (1) or a pharmaceutically acceptable one thereof. Admixture with appropriate pharmaceutical excipients, binders, lubricants, disintegrants, coatings, emulsifiers, dispersants, solvents, stabilizers, adsorption enhancers and / or ointment bases By doing so, it is administered in a suitably formulated pharmaceutical mixture for the particular use and desired purpose, wherein the mixture is used for oral, injection, rectal or topical administration. can do.
  • Pharmaceutical dosage forms for oral administration may be granules, tablets, dragees, capsules, pills, suspensions or emulsions.
  • the preparation may be used in the form of a sterile aqueous solution containing, for example, salts or glucose to make the solution isotonic. Can be done.
  • the antifungal agent of the present invention can also be administered in the form of suppositories or vaginal insertion suppositories, which are prepared, for example, into solutions, tablets, suppositories, emulsifiers, ointments, creams, lotions, cataplasms and the like It may be administered locally.
  • these preparations can also contain auxiliaries, stabilizers, wetting or emulsifying agents, buffers and other commonly used additives.
  • the dose of the compound varies depending on the symptoms, age, weight, dosage form, etc., but in the case of systemic treatment, it is generally 0.05 to 100 mg / kg of body weight per adult, preferably 0.05 to 100 mg / day. 0.5 to 50 m can be administered once or several times.
  • the concentration of the active ingredient in topical treatment ranges from 0.001 to 5%, preferably from 0.1 to 2%.
  • the actual production method of such a dosage form is a usual method, for example, Rem in g t on s P h a r ma c e u t i c a l S c i e n c e s, 18th edition, Mack P u b l i s h i n C omp a n y, E as t o n, P e n n s y l v a n
  • the active ingredient 10 If the above components are mixed and wet-milled until the particle size becomes 1 micron or less, the active ingredient 10
  • Example 9 water-absorbing ointment
  • Compound of the present invention 50 parts Lactose 29 parts Corn starch 10 parts Starch sodium glycolate 5 parts Polyvinyl pyrrolidone 3 parts Talc 2 parts Magnesium stearate 1 part Examples 16 capsules
  • Each is filled into a suitable hard gelatin capsule so as to contain 20 mg of the active ingredient.
  • Test Examples show that the compounds of the present invention are useful as effective components of various plant disease controlling agents.
  • the control effect was determined by visually observing the growth of the diseased flora that appeared on the leaves, stems, etc. at the time of the survey, and determining the control effect.
  • Test example 1 Wheat powdery mildew control test
  • Emulsions of the compound of the present invention were sprayed at a concentration of 200 ppm of the active ingredient on ringo seedlings (variety “Kunimitsu”, 3-4 leaf stage) cultivated in unglazed pots. After spraying, air-dry at room temperature, inoculate conidia of the scab of the lingo scab (Venturiainaequa 1 is), and in a high-humidity constant temperature room (20 ° C) where light and dark are repeated every 12 hours for 2 weeks. Held. The appearance of lesions on the leaves was compared with that of no treatment, and the control effect was determined. As a result, the following compounds showed an excellent control effect of 75% or more.
  • Grape seedlings (variety “Kaiji”, 2 leaf stage) grown in unglazed pots were sprayed with an emulsion of the compound of the present invention at a concentration of 200 ppm of the active ingredient. After spraying, air-dry at room temperature, inoculate with a suspension of zoospores of Grape downy mildew (Plasmoparavitico 1a), and in a high-humidity constant temperature room (20 ° C) where light and dark are repeated every 12 hours. Held for 10 days. The appearance of disease spots on the leaves was compared with that of no treatment, and the control effect was determined. As a result, the following compounds exhibited excellent control effects of 75% or more.
  • the flowers of the kidney beans (variety “Nagauzura”) cultivated in the seedling raising bucket were excised, and the emulsion of the compound of the present invention was immersed in a drug solution prepared to a concentration of 200 ppm of the active ingredient. After immersion, it was air-dried at room temperature and spray-inoculated with green bean fungus (B0trytyscisinerea_).
  • B0trytyscisinerea_ green bean fungus
  • the inoculated flowers were placed on untreated bean 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 the leaves was compared with that of the untreated group, and the control value was determined. As a result, the following compounds exhibited a controlling rate of 105%.
  • the compound was diluted with water so that the compound concentration became 125 ppm.
  • the corn leaves were immersed in the solution for 30 seconds and air-dried.
  • the leaves were put into a petri dish containing five second instar larvae. They were covered with a glass lid and placed in a constant temperature room at a temperature of 25 ° C and a humidity of 65%, and the insecticidal rate was measured after 5 days.
  • the test was performed in duplicate.
  • Chlordimeform (125 ppm) was used as a control compound.
  • the following compounds showed an excellent insecticidal rate of 80% or more.
  • the insecticidal rate of the control compound chlordimeform was 40%.
  • a 10-day old germinated soybean seeded in a three-dimensional bowl was inoculated with a petal aphid adult.
  • the adults were removed, and the cucumber parasitized by the nymphs produced was diluted with water so that the compound concentration became 125 ppm according to the emulsion formulation shown in Example 4 of the above-mentioned drug.
  • insecticidal rate of the control compound pirimicarb was 9%.
  • the malaria parasite was cultured at 36.5 ° C with an oxygen concentration of 5.0%, a carbon dioxide concentration of 5.0%, and a nitrogen concentration of 9.0%.
  • the pre-cultured P. falciparum was diluted with uninfected erythrocytes so that the initial infection rate was 0.5%, and dispensed into 24-well culture plates.
  • the compound of Compound No. 67 in Table 2 was dissolved in DMS0 to prepare a sample solution having a predetermined concentration. This sample solution was added to the 24-well plate, and the solution was mixed by pitting. After culturing for 72 hours, a thin-layered smear was prepared for each pellet, and the infection rate was measured under a light microscope. Antiprotozoal activity was evaluated from the infection rate of the drug-added and control infection rates. As a result, it did not grow want to wait even Izure of the parasite at a concentration of 1 0 one 6 M.

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  • 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)
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  • Wood Science & Technology (AREA)
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  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des composés de thiazole représentés par la formule générale (1) ou leurs sels; ainsi qu'un bactéricide, un insecticide/acaricide et un fongicide, tous ces produits étant destinés à un usage agricole ou horticole; dans la formule (1) selon l'invention, R1 et R2 représentent chacun indépendamment un halogéno, un alkyle en C¿1-6?, etc.; X représente O, S, etc.; et Y représente n'importe lequel des groupes représentés par les formules (a) à (c) (dans lesquelles Het représente éventuellement un thiényle, un furyle, un pyridyle, un thiazolyle, un pyrimidinyle ou un pyrazinyle substitués).
PCT/JP1999/000473 1998-02-05 1999-02-04 Composes de thiazole, procede de production, agent antiparasitaire et agent antifongique WO1999040076A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU22989/99A AU2298999A (en) 1998-02-05 1999-02-04 Thiazole compounds, production process, pest control agent, and antifungal agent

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2485398 1998-02-05
JP10/24853 1998-02-05
JP37169498 1998-12-25
JP10/371694 1998-12-25

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WO1999040076A1 true WO1999040076A1 (fr) 1999-08-12

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PCT/JP1999/000473 WO1999040076A1 (fr) 1998-02-05 1999-02-04 Composes de thiazole, procede de production, agent antiparasitaire et agent antifongique

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WO (1) WO1999040076A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003050096A1 (fr) * 2001-12-13 2003-06-19 Isagro Ricerca S.R.L. Derives de thiazole avec une activite fongicide
WO2015005499A1 (fr) * 2013-07-12 2015-01-15 住友化学株式会社 Composé de tétrazolinone et son utilisation
CN105873911A (zh) * 2014-01-06 2016-08-17 住友化学株式会社 噻唑化合物及其有害生物防除用途

Citations (4)

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Publication number Priority date Publication date Assignee Title
JPS6431746A (en) * 1987-07-11 1989-02-02 Schering Agrochemicals Ltd Acrylic fungicide
JPH05213815A (ja) * 1991-05-17 1993-08-24 Basf Ag α−フェニルアクリル酸誘導体およびこれを使用する有害虫類、真菌類の防除方法
JPH07502747A (ja) * 1992-01-29 1995-03-23 ビーエーエスエフ　アクチェンゲゼルシャフト カルバメートおよびそれらを含む作物保護剤
JPH08507055A (ja) * 1993-02-23 1996-07-30 ビーエーエスエフ アクチェンゲゼルシャフト オルト置換２−メトキシイミノフェニル酢酸メチルアミド

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6431746A (en) * 1987-07-11 1989-02-02 Schering Agrochemicals Ltd Acrylic fungicide
JPH05213815A (ja) * 1991-05-17 1993-08-24 Basf Ag α−フェニルアクリル酸誘導体およびこれを使用する有害虫類、真菌類の防除方法
JPH07502747A (ja) * 1992-01-29 1995-03-23 ビーエーエスエフ　アクチェンゲゼルシャフト カルバメートおよびそれらを含む作物保護剤
JPH08507055A (ja) * 1993-02-23 1996-07-30 ビーエーエスエフ アクチェンゲゼルシャフト オルト置換２−メトキシイミノフェニル酢酸メチルアミド

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003050096A1 (fr) * 2001-12-13 2003-06-19 Isagro Ricerca S.R.L. Derives de thiazole avec une activite fongicide
WO2015005499A1 (fr) * 2013-07-12 2015-01-15 住友化学株式会社 Composé de tétrazolinone et son utilisation
JPWO2015005499A1 (ja) * 2013-07-12 2017-03-02 住友化学株式会社 テトラゾリノン化合物及びその用途
US9888688B2 (en) 2013-07-12 2018-02-13 Sumitomo Chemical Company, Limited Tetrazolinone compounds and applications thereof
CN105873911A (zh) * 2014-01-06 2016-08-17 住友化学株式会社 噻唑化合物及其有害生物防除用途
US9730449B2 (en) 2014-01-06 2017-08-15 Sumitomo Chemical Company, Limited Thiazole compound and its use in pest control
CN105873911B (zh) * 2014-01-06 2018-07-24 住友化学株式会社 噻唑化合物及其有害生物防除用途

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