WO1995018106A1 - Derive de 4-trifluoromethylpyridine et procede pour sa preparation - Google Patents

Derive de 4-trifluoromethylpyridine et procede pour sa preparation Download PDF

Info

Publication number
WO1995018106A1
WO1995018106A1 PCT/JP1994/002287 JP9402287W WO9518106A1 WO 1995018106 A1 WO1995018106 A1 WO 1995018106A1 JP 9402287 W JP9402287 W JP 9402287W WO 9518106 A1 WO9518106 A1 WO 9518106A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
general formula
groups
substituted
represented
Prior art date
Application number
PCT/JP1994/002287
Other languages
English (en)
Japanese (ja)
Inventor
Masaharu Ishiguro
Tatsuyoshi Ishida
Ikuo Tomino
Original Assignee
Mitsui Petrochemical Industries, 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 Mitsui Petrochemical Industries, Ltd. filed Critical Mitsui Petrochemical Industries, Ltd.
Publication of WO1995018106A1 publication Critical patent/WO1995018106A1/fr

Links

Classifications

    • 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
    • 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
    • C07D213/69—Two or more oxygen atoms

Definitions

  • the present invention provides a compound represented by the general formula (I):
  • X represents a halogen atom, a hydrogen atom or a lower alkoxy group
  • R 1 represents a hydrogen atom or a lower alkoxycarbonyl group
  • R 2 represents a lower alkanesulfonyl group, a benzenesulfonyl group or the following formula:
  • R 3 is an alkyl group, a haloalkyl group, a lower alkoxy-substituted lower alkyl group, a lower alkoxycarbonyl group-substituted lower alkyl group, a carboxyl group-substituted lower alkyl group, a cycloalkyl group, a phenyl group (the phenyl group)
  • a pyridyl group, a furyl group, a phenyl group It represents an amino group or a di-lower alkylamino group.
  • the compounds of the present invention are useful as herbicides, and exhibit high herbicidal activity, particularly against various annual weeds in paddy fields or fields. Background art
  • Ar represents an optionally substituted aromatic or heteroaromatic compound (having one or more ⁇ , N and S), and R represents a hydrogen atom, an alkyl substitution force
  • R represents a hydrogen atom, an alkyl substitution force
  • hydroxylamine derivatives used as a growth factor for plants represented by the following are disclosed. And 3 ⁇ 4 to force, not described in detail for 4 one triflumizole Ruo b-piperidine lysine derivative of a specific structure of the present invention. Disclosure of the invention
  • the present inventors have synthesized a large number of various compounds for the purpose of developing a herbicide, and have conducted extensive screening tests. As a result, a novel 4-trifluoromethylpyridine derivative having a specific substituent has been obtained. Showed high herbicidal activity, and completed the present invention.
  • the present invention provides a compound represented by the general formula (I):
  • X represents a halogen atom, a hydrogen atom or a lower alkoxy group
  • R 1 represents a hydrogen atom or a lower alkoxycarbonyl group
  • R 2 represents a lower alkanesulfonyl group, a benzenesulfonyl group or the following formula:
  • R 3 is an alkyl group, a haloalkyl group, a lower alkoxy-substituted lower alkyl group, a lower alkoxycarbonyl group-substituted lower alkyl group, a carboxyl group-substituted lower alkyl group, a cycloalkyl group, a phenyl group (the phenyl group)
  • the alkyl group may be substituted with 1 to 5 lower alkyl groups, halogen atoms, trifluoromethyl groups, nitro groups, cyano groups or lower alkoxy groups), pyridyl groups, furyl groups, chenyl groups, amino groups Or a di-lower alkylamino group).
  • -Trifluoromethylpyridine derivative represented by the formula:
  • the present invention relates to a method for producing a 4-trifluoromethylpyridine derivative represented by the following formula:
  • the present invention relates to a process for producing a 4-trifluoromethylpyridine derivative represented by the following formula:
  • X represents a halogen atom, a hydrogen atom or a lower alkoxy group.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and among them, a chlorine atom is preferable.
  • the lower alkoxy group an alkoxy group having 1 to 4 carbon atoms, for example, methoxy group, ethoxy group, ⁇ -propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group or t-butoxy group Among them, a methoxy group is preferred.
  • X is preferably a halogen atom, particularly a chlorine atom.
  • R 1 represents a hydrogen atom or a lower alkoxycarbonyl group.
  • the lower alkoxycarbonyl group an alkoxycarbonyl group having 2 to 5 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an isopropoxycarbonyl group, an n-butoxycarbonyl group, an isobutoxycarbonyl group, Examples thereof include a sec-butoxycarbonyl group and a t-butoxycarbonyl group.
  • R 2 is a lower alkanesulfonyl group, a benzenesulfonyl group or the following formula:
  • examples of the lower alkanesulfonyl group include an alkanesulfonyl group having 1 to 4 carbon atoms, such as a methanesulfonyl group and an ethanesulfonyl group.
  • R 3 is an alkyl group, haloalkyl group, lower alkoxy C-substituted lower alkyl group, lower alkoxycarbonyl group-substituted lower alkyl group, methoxyl-substituted lower alkyl group, cycloalkyl group, phenyl group (the phenyl group is a lower alkylyl group, a halogen atom, a trifluoromethylyl group, a nitro group) , A cyano group or a lower alkoxy group which may be substituted by 1 to 5), a pyridyl group, a furyl group, a phenyl group, a phenyl group, an amino group or a di-lower alkylamino group.
  • Examples of the alkyl group represented by R 3 include an alkyl group having 1 to 10 carbon atoms, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a t-butyl group.
  • Examples of the lower alkoxy-substituted lower alkyl group represented by R 3 include an alkyl group having 1 to 4 carbon atoms substituted with an alkoxy group having 1 to 4 carbon atoms, specifically, a methoxymethyl group and a 1-methoxyethyl group. , 2-methoxyl, 3-methoxypropyl, 4-methoxybutyl, 2-ethoxyl, isopropoxymethyl, 41-t-butoxybutyl and the like.
  • alkyl group having 1 to 4 carbon atoms which is substituted by an alkoxyl group having 2 to 5 carbon atoms, specifically, a methoxycarbonylmethyl group.
  • 2-methoxycarbonylethyl, 3-methoxycarbonylpropyl, 4-methoxycarbonylbutyl, 2-ethoxycarbonylethyl, isopropoxycarbonylmethyl, 4-t-butoxycarbonyl A butyl group and the like can be mentioned.
  • a carboxyl group-substituted alkyl group having 1 to 4 carbon atoms such as carboxymethyl group
  • Examples include a boxyshethyl group, a 3-carboxypropyl group, and a 4-carboxybutyl group.
  • the cycloalkyl group represented by R 3 can be exemplified a cycloalkyl group having 3 to 6 carbon atoms, specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, a key sill group cyclohexylene.
  • the lower alkyl group to be substituted includes an alkyl group having 1 to 4 carbon atoms, specifically the same as those described above, and the lower alkoxy group has 1 carbon atom.
  • the same alkoxy groups as described above in Examples 4 to 4 can be mentioned, and the halogen atom can be the same as described above.
  • Examples of the pyridyl group represented by R 3 include a 2-pyridyl group, a 3-pyridyl group and a 4-pyridyl group.
  • Examples of the furyl group include a 2-furyl group and a 3-furyl group.
  • Examples of the phenyl group include a 2-phenyl group and a 3-phenyl group.
  • di-lower alkylamino group examples include an amino group substituted with an alkyl group having 1 to 4 carbon atoms, such as a dimethylamino group, a getylamino group, a di-n-propylamino group, a diisopropylamino group, a di-n-butylamino group, Diisobutylamino group, di-sec-butylamino group, di-t-butylamino group and the like.
  • an amino group substituted with an alkyl group having 1 to 4 carbon atoms such as a dimethylamino group, a getylamino group, a di-n-propylamino group, a diisopropylamino group, a di-n-butylamino group, Diisobutylamino group, di-sec-butylamino group, di-t-butylamino group and the like.
  • preferred compounds include, for example, the compounds shown in Table 1.
  • the general formula (Ia) corresponds to the case where R 1 in the general formula (I) is a hydrogen atom and R 2 is —CO—R 3 .
  • the general formula (Ib) corresponds to the case where R 1 in the general formula (I) is a hydrogen atom.
  • H a1 represents a halogen atom, and includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the compound (I) of the present invention can be synthesized by the following three methods.
  • the first method (hereinafter referred to as “method a” :) is represented by the general formula ( ⁇ ): CF
  • a base examples include sodium hydroxide, alkali metal hydroxides such as hydroxide hydroxide, alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide, and sodium hydride.
  • Metal hydrides such as hydrogen hydride and the like are preferred.
  • the amount of the base to be used is generally 0.5 to 5 mol, preferably 0.8 to 3 mol, particularly preferably 1 to 2 mol, per 1 mol of the compound represented by the formula (III).
  • reaction is carried out in the presence of hydrocarbons such as benzene and toluene, ethers such as methyl ether, tetrahydrofuran and dioxane, alcohols such as methanol, ethanol, isopropanol and t-butanol, or N, N-dimethylform.
  • hydrocarbons such as benzene and toluene
  • ethers such as methyl ether, tetrahydrofuran and dioxane
  • alcohols such as methanol, ethanol, isopropanol and t-butanol, or N, N-dimethylform.
  • the reaction temperature is usually from 20 ° C to 150 ° C, preferably from 0 ° C to 120 ° C, particularly preferably from 10 ° C to 100 ° C.
  • the compound represented by the formula (III) is usually used in an amount of 0.5 to 3 mol, preferably 0.7 to 2 mol, particularly preferably 0.1 to 2 mol per mol of the compound represented by the formula (II). Use 9 to 1.5 moles.
  • the compound (I) of the present invention can be produced by the second method (hereinafter, referred to as “method b”) in addition to the above method a.
  • This method b has the general formula (IV):
  • the base used is Amines such as gin, bicholine, lutidine, dimethylaminopyridine, trimethylamine and triethylamine; alkali metal carbonates such as carbon dioxide, sodium carbonate and sodium bicarbonate; sodium hydroxide; Alkali metal hydroxides such as potassium thiocyanate; alkaline earth metal hydroxides such as calcium hydroxide; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide; Amines such as picoline and triethylamine are preferred.
  • Amines such as gin, bicholine, lutidine, dimethylaminopyridine, trimethylamine and triethylamine
  • alkali metal carbonates such as carbon dioxide, sodium carbonate and sodium bicarbonate
  • sodium hydroxide Alkali metal hydroxides such as potassium thiocyanate
  • alkaline earth metal hydroxides such as calcium hydroxide
  • alkali metal alkoxides such as sodium
  • the amount of the base to be used is generally 0.5 to 10 mol, preferably 0.8 to 8 mol, particularly preferably 1.0 to 6 mol, per 1 mol of the compound represented by the general formula (IV).
  • the reaction is carried out without solvent or in a solvent such as halogenated hydrocarbons such as dichloromethane, dichloroethane, and chloroform, hydrocarbons such as benzene and toluene, and ethers such as dimethyl ether, tetrahydrofuran, and dioxane. Is preferred.
  • the reaction temperature is usually from 150 ° C to 100 ° C, preferably from ⁇ 30 ° C to 80 ° C. C, particularly preferably 0 ° C to 60 ° C.
  • the compound represented by the formula (V) is usually 0.5 to 8 mol, preferably 1.0 to 6 mol, particularly preferably 1.0 to 1 mol of the compound represented by the formula (IV). Use 5-4 moles.
  • compound (I) of the present invention can also be produced by a third method (hereinafter, referred to as “method c”).
  • This method c has the general formula (VI):
  • a base For this reaction, it is preferable to use a base.
  • the base include alkali metal hydroxides such as hydroxydium hydroxide and potassium potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide.
  • Alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide, and alkali metal hydrides such as sodium hydride and potassium hydride are preferred.
  • the amount of base used is the general formula
  • the amount is generally 0.5 to 30 mol, preferably 1 to 15 mol, particularly preferably 3 to 10 mol, per 1 mol of the compound represented by (VI).
  • the reaction includes alcohols such as methanol, ethanol, isopropanol and t-butanol, water, halogenated hydrocarbons such as dichloromethane and dichloroethane, ethers such as dimethyl ether, tetrahydrofuran and dioxane, N, N-dimethylformamide, It is preferable to carry out the reaction in a solvent such as an aprotic polar solvent such as N, N-dimethylacetamide.
  • a solvent such as an aprotic polar solvent such as N, N-dimethylacetamide.
  • the reaction temperature is usually from 0 ° C to 150.
  • Z preferably from 10 ° C to 50 ° C, particularly preferably from 20 ° C to 40 ° C.
  • the compound of the present invention as a herbicide, the compound of the present invention alone, or a carrier, a surfactant, a dispersing agent, an auxiliary agent, and the like, and a wettable powder, an emulsion, a powder, a fine granule, or a granule in combination with the compound of the present invention And dilute it to an appropriate concentration before spraying or applying directly.
  • the compound of the present invention or a preparation containing the compound can be used as a surface treatment or admixed with soil, which can be directly sprayed and used on weeds.
  • the application rate is about 10 to 400 g / ha as a normally active ingredient amount that varies depending on the type of target weed, the type of target crop, and the mode of application.
  • Example 3 The same operation was performed in the same manner as in Example 3 except that methanesulfonyl chloride was replaced with acetyl, propionyl chloride, isobutyryl chloride, bivaloyl chloride, nonanoyl chloride, ethanesulfonyl chloride, or benzenesulfonyl chloride.
  • the results and physical properties data are shown in Table 3 (mp: ° C) o
  • a wettable powder was prepared by uniformly mixing and grinding 10% of the compound of the present invention, 3% of a sodium salt of a higher alcohol sulfate and 87% of kaolin.
  • Emulsion An emulsion was prepared by uniformly dissolving 20% of the compound of the present invention, 10% of polyoxyethylene alkylaryl ether, 30% of cyclohexanone and 40% of xylene.
  • Filter paper (2 sheets) was spread over a petri dish with a lid of 9 cm in diameter, and seeds of Nobie, Mehishiba, Aobu and Alfalpha were sown. 20 ml of a diluted aqueous solution of liquid fertilizer and a wettable powder of a test compound (prepared according to Example 7) were diluted with water at a rate of 1 OOg / lha as an active ingredient and sprayed. After 10 days at 30 ° C under light irradiation (3000 lux), the herbicidal effect was visually evaluated based on the criteria shown in Table 4.
  • a novel 4-trifluoromethylpyridine derivative is provided.
  • the 4-trifluoromethylpyridine derivative of the present invention is useful as a herbicide, and particularly exhibits a high herbicidal effect on various annual weeds in paddy fields or fields.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Dérivé de 4-trifluorométhylpyridine représenté par la formule générale (I) et utile comme herbicide. Dans cette formule, X représente halogène, hydrogène ou alcoxy inférieur; R1 représente hydrogène ou alcoxycarbonyle inférieur; et R2 représente alcanesulfonyle inférieur, benzènesulfonyle ou bien -CO-R?3, où R3¿ représente alkyle, haloalkyle, alkyle inférieur substitué par alcoxy inférieur, alkyle inférieur substitué par alcoxycarbonyle inférieur, alkyle inférieur substitué par carboxyle, cycloalkyle, phényle (qui peut être substitué par un à cinq groupes alkyle inférieur, halogène, trifluorométhyle, nitro, cyano ou alcoxy inférieur), pyridyle, furyle, thiényle, amino ou di(alkyle inférieur) amino.
PCT/JP1994/002287 1993-12-28 1994-12-28 Derive de 4-trifluoromethylpyridine et procede pour sa preparation WO1995018106A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP5/338665 1993-12-28
JP33866593A JPH07196619A (ja) 1993-12-28 1993-12-28 ４−トリフルオロメチルピリジン誘導体及びその製造方法

Publications (1)

Publication Number Publication Date
WO1995018106A1 true WO1995018106A1 (fr) 1995-07-06

Family

ID=18320313

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1994/002287 WO1995018106A1 (fr) 1993-12-28 1994-12-28 Derive de 4-trifluoromethylpyridine et procede pour sa preparation

Country Status (2)

Country Link
JP (1) JPH07196619A (fr)
WO (1) WO1995018106A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987007269A1 (fr) * 1986-05-26 1987-12-03 Mitsui Petrochemical Industries, Ltd. Aryloxyurees, procede de preparation et leur utilisation
JPS649969A (en) * 1987-07-02 1989-01-13 Mitsui Petrochemical Ind N-aryloxycarbamic acid esters, production thereof and herbicide comprising said esters as active ingredient
JPH01131146A (ja) * 1987-07-02 1989-05-24 Mitsui Petrochem Ind Ltd アリールオキシ尿素類、その製造法およびそれを有効成分として含有する除草剤

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987007269A1 (fr) * 1986-05-26 1987-12-03 Mitsui Petrochemical Industries, Ltd. Aryloxyurees, procede de preparation et leur utilisation
JPS649969A (en) * 1987-07-02 1989-01-13 Mitsui Petrochemical Ind N-aryloxycarbamic acid esters, production thereof and herbicide comprising said esters as active ingredient
JPH01131146A (ja) * 1987-07-02 1989-05-24 Mitsui Petrochem Ind Ltd アリールオキシ尿素類、その製造法およびそれを有効成分として含有する除草剤

Also Published As

Publication number Publication date
JPH07196619A (ja) 1995-08-01

Similar Documents

Publication Publication Date Title
JP2598540B2 (ja) アルコキシ‐１，２，４‐トリアゾロ〔１，５‐ｃ〕ピリミジン‐２‐スルホンアミド，その製造法及び中間体
CN111315742B (zh) 制备氨基嘧啶衍生物的方法
CA2556480A1 (fr) Derives de pyrimidine et utilisation de ceux-ci comme fongicides agricoles et horticoles
TW202005958A (zh) 製備可滅蹤之製程、其新穎形式及其用途
JPH05294920A (ja) 新規な３−アリールウラシル誘導体および雑草防除に対するそれらの使用方法
AU674240B2 (en) Indazolesulfonylurea derivative, use thereof, and intermediate for production thereof
WO2002002540A1 (fr) Compose de benzoxazole, son procede de production, et desherbant
JPH04235171A (ja) スルホヒドロキサム酸誘導体、その製造法およびそれを有効成分とする除草剤
AU2003211534A1 (en) Cyclic compound, process for producing the same, and pest control agent
WO1995018106A1 (fr) Derive de 4-trifluoromethylpyridine et procede pour sa preparation
JPH07267931A (ja) スルホンアミド誘導体の製造方法
JPH08291146A (ja) 除草性ｎ−（置換フェニル）スルホンアミド化合物
WO1996020195A1 (fr) Derives d'hydantoine, procede de production et herbicides les incluant comme ingredients actifs
JPH05246998A (ja) アリールインダゾール誘導体およびそれを有効成分とする除草剤
EP0427445B1 (fr) Dérivés amidés d'acides benzylidène-aminooxyalcane(thi)oiques, procédé pour leur préparation et herbicides
JP2794056B2 (ja) Ｎ−置換フェニル−３、４、５、６−テトラヒドロフタルイミド誘導体及びそれを有効成分とする除草剤
RU2626957C2 (ru) 2,6 -дигалоген-5-алкокси-4-замещенные-пиримидины, пиримидинкарбальдегиды и способы получения и применения
JP2730021B2 (ja) ３−ベンジルオキシアルカン酸誘導体、その製造法及び除草剤
JP3064371B2 (ja) ベンゾオキサジルウラシル誘導体、その製造法およびそれを有効成分とする除草剤
JPH01305089A (ja) トリアゾリルスルホンアミド、その製法および該化合物を含む除草剤
JP2809483B2 (ja) ６―インドリジンカルボキサミド誘導体、その中間体それらの製造法および除草剤
JP5016760B2 (ja) ベンゾオキサゾール誘導体，その製法及び除草剤
JPH08208613A (ja) ２−クロロ−６−ヒドロキシイソニコチン酸誘導体及び植物病害防除剤
CN118221605A (zh) 一类含异噁唑啉类化合物、其制备方法及应用
JPH03251582A (ja) イミダゾ［１，２―ａ］ピリジル化合物

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA