CN108947964B - Fungicide hydroximoyl-tetrazole derivatives - Google Patents

Fungicide hydroximoyl-tetrazole derivatives Download PDF

Info

Publication number
CN108947964B
CN108947964B CN201710362005.2A CN201710362005A CN108947964B CN 108947964 B CN108947964 B CN 108947964B CN 201710362005 A CN201710362005 A CN 201710362005A CN 108947964 B CN108947964 B CN 108947964B
Authority
CN
China
Prior art keywords
compound
alkyl
diseases
base
group
Prior art date
Legal status (The legal status 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 status listed.)
Active
Application number
CN201710362005.2A
Other languages
Chinese (zh)
Other versions
CN108947964A (en
Inventor
李义涛
熊力
卢辉
程健
刘新烁
林健
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dongguan dongyangguang pesticide R & D Co., Ltd
Original Assignee
Dongguan Dongyang Guangke Research and Development 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 Dongguan Dongyang Guangke Research and Development Co Ltd filed Critical Dongguan Dongyang Guangke Research and Development Co Ltd
Priority to CN201710362005.2A priority Critical patent/CN108947964B/en
Publication of CN108947964A publication Critical patent/CN108947964A/en
Application granted granted Critical
Publication of CN108947964B publication Critical patent/CN108947964B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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
    • A01N43/80—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 1,2
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • 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
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (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)

Abstract

The present invention provides a kind of fungicide hydroximoyl-tetrazole derivatives；Specifically, the present invention relates to oximido-terazole derivatives, their preparation method, and their purposes as fungicide active agents, and its form of Fungicidal composition, and the method for controlling with these compound or compositions plant pathogenic fungi (plant pathogenic fungi especially in plant).

Description

Fungicide hydroximoyl-tetrazole derivatives
Technical field
The present invention relates to oximido (hydroximoyl)-terazole derivatives, their preparation method and their conducts are killed The purposes of fungi activity agent and its form of Fungicidal composition, and phytopathy is controlled with these compound or compositions The method of fungal pathogens (plant pathogenic fungi especially in plant).
Background technique
In PCT Patent Application WO 2009130193, the tetrazole radical 9 oxime derivate with following formula chemical structure is disclosed:
Wherein T indicates to be selected from T1-T117Substituted or unsubstituted heterocycle；A is selected from A1-A116It is substituted or unsubstituted Aryl, heteroaryl or heterocycle；Q is selected from Q1-Q112Substituted or unsubstituted aryl, heteroaryl, heterocycle, naphthenic base or ring Alkenyl；L1Indicate direct key or bilvalent radical.
In Japanese patent application JP 2011012088, the tetrazole radical 9 oxime derivate with following formula chemical structure is disclosed:
Wherein A is substituted or unsubstituted heterocycle；B is a key or substituted or unsubstituted alkylidene；X be replace or Unsubstituted aromatic rings or non-aromatic ring；Y is substituted or unsubstituted aryl.
The compound of the present invention is not disclosed in this two patents document.
People pay high attention to always the application of novel pesticide compound in agriculture field, to avoid or prevention and control to active ingredient There is the generation of the bacterial strain of drug resistance.Same people pay high attention to use compounds more higher than known compound activity, mesh Be marked in reduce used in reactive compound amount, maintain at the same time at least with the comparable effect of known compound.This hair It is bright provide one kind have the advantages that said effect or noval chemical compound.
Summary of the invention
The present invention provides formula (I) compound represented, the salt of compound shown in formula (I), N- oxide, metal complex, Metal complexes or (E) and (Z) isomers and their mixture:
Wherein:
X is hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, alkyl, alkoxy, alkylamino or alkane sulphur Base；
Y is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, naphthenic base, heterocycle, aryl alkyl, heteroaryl alkyl, ring Alkyl-alkyl, heterocyclylalkyl group ,-C (=O)-alkyl ,-C (=O)-alkenyl ,-C (=O)-alkynyl ,-C (=O)-aryl ,-C (= O)-heteroaryl ,-C (=O)-naphthenic base ,-C (=O)-heterocycle ,-C (=O)-O- alkyl ,-C (=O)-O- alkenyl ,-C (= O)-O- alkynyl ,-C (=O)-alkylene-aryl ,-C (=O)-alkenylene-aryl ,-C (=O)-alkylene-heteroaryl ,-C (= O)-alkenylene-heteroaryl ,-C (=O)-alkylene-cycloalkyl ,-C (=O)-alkenylene-naphthenic base ,-C (=O)-alkylidene- Heterocycle ,-C (=O)-alkenylene-heterocycle ,-S (=O)2Alkyl ,-S (=O)2Alkenyl ,-S (=O)2Alkynyl ,-S (= O)2Aryl ,-S (=O)2Heteroaryl ,-S (=O)2Naphthenic base or-S (=O)2Heterocycle；Wherein Y optionally by 1,2,3, 4,5,6,7,8,9 or 10 are selected from R1Substituent group replaced；
Each R1It independently is fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, alkyl, halogenated alkyl, alcoxyl Base, halogenated alkoxy, alkylamino, halogenated alkylamino, alkylthio group, halogenated alkylthio ,-C (=O)-alkyl ,-C (=O)-alkenyl ,- C (=O)-alkynyl ,-S (=O)2Alkyl ,-S (=O)2Alkenyl or-S (=O)2Alkynyl；
A and T is each independently aryl, heteroaryl, naphthenic base, cycloalkenyl or heterocycle；Wherein A and T respectively independently appoints Selection of land is selected from R by 1,2,3,4,5,6,7,8,9 or 102Substituent group replaced；
Each R2It independently is fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, alkyl, halogenated alkyl, alcoxyl Base, halogenated alkoxy, alkylamino, halogenated alkylamino, alkylthio group or halogenated alkylthio；
Wherein X, R1And R2R is optionally selected from by one or more3Substituent group replaced；
Each R3It independently is hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, amino, carboxyl, C1-6Alkyl, C2-6Alkenyl, C2-6Alkynyl, halogenated C1-6Alkyl, halogenated C2-6Alkenyl, halogenated C2-6The C that alkynyl, hydroxyl replace1-6The C that alkyl, amino replace1-6Alkane The C that base, cyano replace1-6Alkyl, C1-6Alkoxy, halogenated C1-6The C that alkoxy, hydroxyl replace1-6Alkoxy, amino replace C1-6The C that alkoxy, cyano replace1-6Alkoxy, C1-6Alkylamino, C3-8Naphthenic base, C6-10Aryl or C1-9Heteroaryl.
In some of embodiments, X is hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, C1-6Alkane Base, C1-6Alkoxy, C1-6Alkylamino or C1-6Alkylthio group.
In some of embodiments, Y is hydrogen, C1-10Alkyl, C2-8Alkenyl, C2-8Alkynyl, C6-10Aryl, C1-9Heteroaryl, C3-12Naphthenic base, C2-12Heterocycle, C6-10Aryl C1-6Alkyl, C1-9Heteroaryl C1-6Alkyl, C3-12Naphthenic base C1-6Alkyl, C2-12It is miscellaneous Ring group C1-6Alkyl ,-C (=O)-C1-10Alkyl ,-C (=O)-C2-8Alkenyl ,-C (=O)-C2-8Alkynyl ,-C (=O)-C6-10Virtue Base ,-C (=O)-C1-9Heteroaryl ,-C (=O)-C3-12Naphthenic base ,-C (=O)-C2-12Heterocycle ,-C (=O)-O-C1-8Alkyl ,- C (=O)-O-C2-8Alkenyl ,-C (=O)-O-C2-8Alkynyl ,-C (=O)-C1-6Alkylidene-C6-10Aryl ,-C (=O)-C2-6Sub- alkene Base-C6-10Aryl ,-C (=O)-C1-6Alkylidene-C1-9Heteroaryl ,-C (=O)-C2-6Alkenylene-C1-9Heteroaryl ,-C (=O)- C1-6Alkylidene-C3-8Naphthenic base ,-C (=O)-C2-6Alkenylene-C3-8Naphthenic base ,-C (=O)-C1-6Alkylidene-C2-10Heterocycle Base ,-C (=O)-C2-6Alkenylene-C2-10Heterocycle ,-S (=O)2-C1-6Alkyl ,-S (=O)2-C2-6Alkenyl ,-S (=O)2-C2-6 Alkynyl ,-S (=O)2-C6-10Aryl ,-S (=O)2-C1-9Heteroaryl ,-S (=O)2-C3-8Naphthenic base or-S (=O)2-C2-10Heterocycle Base；Wherein Y is optionally selected from R by 1,2,3,4,5,6,7,8,9 or 101Substituent group replaced；
Wherein each R1With meaning as described in the present invention.
In some of embodiments, each R1Independently be fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, C1-6Alkyl, halogenated C1-6Alkyl, C1-6Alkoxy, halogenated C1-6Alkoxy, C1-6Alkylamino, halogenated C1-6Alkylamino, C1-6Alkane sulphur Base, halogenated C1-6Alkylthio group ,-C (=O)-C1-6Alkyl ,-C (=O)-C2-6Alkenyl ,-C (=O)-C2-6Alkynyl ,-S (=O)2-C1-6 Alkyl ,-S (=O)2-C2-6Alkenyl or-S (=O)2-C2-6Alkynyl.
In some of embodiments, A and T are each independently C6-10Aryl, C1-9Heteroaryl, C3-8Naphthenic base, C3-8Ring Alkenyl or C2-10Heterocycle；Wherein A and T is selected from R by 1,2,3,4,5,6,7,8,9 or 10 respectively individually optionally2Substituent group It is replaced；
Wherein each R2With meaning as described in the present invention.
In some of embodiments, each R2Independently be fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, C1-6Alkyl, halogenated C1-6Alkyl, C1-6Alkoxy, halogenated C1-6Alkoxy, C1-6Alkylamino, halogenated C1-6Alkylamino, C1-6Alkylthio group Or halogenated C1-6Alkylthio group.
In some of embodiments, Y is hydrogen, C1-8Alkyl, C2-6Alkenyl, C2-6Alkynyl, C6-10Aryl, C1-5Heteroaryl, C3-6Naphthenic base, C3-8Heterocycle, C6-10Aryl C1-3Alkyl, C1-9Heteroaryl C1-3Alkyl, C3-6Naphthenic base C1-3Alkyl, C3-8Heterocycle Base C1-3Alkyl ,-C (=O)-C1-8Alkyl ,-C (=O)-C2-6Alkenyl ,-C (=O)-C2-6Alkynyl ,-C (=O)-C6-10Aryl ,-C (=O)-C1-9Heteroaryl ,-C (=O)-C3-10Naphthenic base ,-C (=O)-C3-8Heterocycle ,-C (=O)-O-C1-6Alkyl ,-C (= O)-O-C2-6Alkenyl ,-C (=O)-O-C2-6Alkynyl ,-C (=O)-C1-4Alkylidene-C6-10Aryl ,-C (=O)-C2-4Alkenylene- C6-10Aryl ,-C (=O)-C1-4Alkylidene-C1-5Heteroaryl ,-C (=O)-C2-4Alkenylene-C1-5Heteroaryl ,-C (=O)-C1-4 Alkylidene-C3-6Naphthenic base ,-C (=O)-C2-4Alkenylene-C3-6Naphthenic base ,-C (=O)-C1-4Alkylidene-C2-6Heterocycle ,-C (=O)-C2-4Alkenylene-C2-6Heterocycle ,-S (=O)2-C1-4Alkyl ,-S (=O)2-C2-4Alkenyl ,-S (=O)2-C2-4Alkynyl ,- S (=O)2-C6-10Aryl ,-S (=O)2-C1-5Heteroaryl ,-S (=O)2-C3-6Naphthenic base or-S (=O)2-C2-6Heterocycle；Wherein Y is optionally selected from R by 1,2,3,4,5,6,7,8,9 or 101Substituent group replaced；
Wherein each R1With meaning as described in the present invention.
In some of embodiments, each R1Independently be fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, C1-4Alkyl, halogenated C1-4Alkyl, C1-4Alkoxy, halogenated C1-4Alkoxy, C1-4Alkylamino, halogenated C1-4Alkylamino, C1-4Alkane sulphur Base, halogenated C1-4Alkylthio group ,-C (=O)-C1-4Alkyl ,-C (=O)-C2-4Alkenyl ,-C (=O)-C2-4Alkynyl ,-S (=O)2-C1-4 Alkyl ,-S (=O)2-C2-4Alkenyl or-S (=O)2-C2-4Alkynyl.
In some of embodiments, Y is hydrogen ,-CH3、-CH2CH3、-CH2CH2CH3、-CH(CH3)2、-CH2CH(CH3)2、- C(CH3)3、-CH2CH2CH2CH2CH3、-CH2CH2CH(CH3)2、-CH2CH(CH3)CH2CH3、-CH(CH2CH3)2、-C(CH3)2CH2CH3、-CH2CH2CH2CH2CH2CH3,-CH=CH2、-CH2CH=CH2、-CH2CH2CH=CH2、-CH2CH=CHCH3、- CH2CH2CH2CH=CH2、-CH2CH2CH=CHCH3、-C≡CH、-CH2-C≡CH、-CH2-C≡CCH3、-CH2CH2-C≡CH、- CH2-C≡CCH2CH3,-C (=O)-CH3,-C (=O)-CH2CH3,-C (=O)-CH2CH2CH3,-C (=O)-CH (CH3)2、-C (=O)-CH2CH(CH3)2,-C (=O)-C (CH3)3,-C (=O)-CH2CH2CH2CH2CH3,-C (=O)-CH2CH2CH(CH3)2、- C (=O)-CH2CH(CH3)CH2CH3,-C (=O)-CH (CH2CH3)2,-C (=O)-C (CH3)2CH2CH3,-C (=O)- CH2CH2CH2CH2CH2CH3,-C (=O)-CH=CH2,-C (=O)-CH2CH=CH2,-C (=O)-CH2CH2CH=CH2,-C (= O)-CH2CH=CHCH3,-C (=O)-CH2CH2CH2CH=CH2,-C (=O)-CH2CH2CH=CHCH3,-C (=O)-C ≡ CH ,- C (=O)-CH2- C ≡ CH ,-C (=O)-CH2-C≡CCH3,-C (=O)-CH2CH2- C ≡ CH ,-C (=O)-CH2-C≡ CCH2CH3,-C (=O)-O-CH3,-C (=O)-O-CH2CH3,-C (=O)-O-CH2CH2CH3,-C (=O)-O-CH (CH3)2、-C (=O)-O-CH2CH(CH3)2,-C (=O)-O-C (CH3)3,-C (=O)-O-CH2CH2CH2CH2CH3,-C (=O)-O- CH2CH2CH(CH3)2,-C (=O)-O-CH2CH(CH3)CH2CH3,-C (=O)-O-CH (CH2CH3)2,-C (=O)-O-C (CH3)2CH2CH3,-C (=O)-O-CH2CH2CH2CH2CH2CH3,-C (=O)-O-CH=CH2,-C (=O)-O-CH2CH=CH2,-C (= O)-O-CH2CH2CH=CH2,-C (=O)-O-CH2CH=CHCH3,-C (=O)-O-CH2CH2CH2CH=CH2,-C (=O)-O- CH2CH2CH=CHCH3,-C (=O)-O-C ≡ CH ,-C (=O)-O-CH2- C ≡ CH ,-C (=O)-O-CH2-C≡CCH3,-C (= O)-O-CH2CH2- C ≡ CH or-C (=O)-O-CH2-C≡CCH2CH3；
Or Y is following subformula:
Wherein Y is optionally selected from R by 1,2,3,4,5 or 61Substituent group replaced；
Wherein each R1With meaning as described in the present invention.
In some of embodiments, each R1Independently be fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, Methyl, ethyl, n-propyl, isopropyl, normal-butyl, tert-butyl, trifluoromethyl, methoxyl group, ethyoxyl, positive propoxy, isopropyl oxygen Base ,-NHCH3、-N(CH3)2、-NHCH2CH3、-SCH3、-SCH2CH3、-SCF3Or-SCH2CF3。
In some of embodiments, A and T are each independently C6-10Aryl, C1-9Heteroaryl, C3-6Naphthenic base, C3-6Ring Alkenyl or C2-8Heterocycle；Wherein A and T is selected from R by 1,2,3,4,5,6,7,8,9 or 10 respectively individually optionally2Substituent group It is replaced；
Wherein each R2With meaning as described in the present invention.
In some of embodiments, each R2Independently be fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, C1-4Alkyl, halogenated C1-4Alkyl, C1-4Alkoxy, halogenated C1-4Alkoxy, C1-4Alkylamino, halogenated C1-4Alkylamino, C1-4Alkylthio group Or halogenated C1-4Alkylthio group.
In some of embodiments, A is following subformula:
In some of embodiments, T is following subformula:
In some of embodiments, the present invention provides a kind of compound, for such as formula (II) compound represented or formula (II) salt of compound shown in, N- oxide, metal complex, metal complexes or (E) and (Z) isomers and they Mixture:
In some of embodiments, the present invention provides a kind of compound, for such as formula (III) compound represented or formula (III) salt, N- oxide, metal complex, metal complexes and their mixture of compound shown in:
In some of embodiments, the present invention provides a kind of compound, is the compound with one of following structure Or salt, N- oxide, metal complex, metal complexes or (E) and (Z) isomery with one of following structural compounds Body and their mixture:
On the other hand, the present invention provides a kind of composition, includes compound of the present invention.
Some of embodiments are that it is living that composition of the present invention further includes acceptable surface in Pesticide Science Property agent and carrier.
On the other hand, the present invention provides compound of the present invention or composition of the present invention in control of plant disease Application.
Some of embodiments are that compound of the present invention or composition of the present invention are therapeutic or preventative Control the application in the plant pathogenic fungi of plant or crop.
On the other hand, the present invention provides the side of the plant pathogenic fungi of the therapeutic or preventive control plant of one kind or crop Compound of the present invention or composition of the present invention are administered to seed, plant or fruit or are administered to just by method In the soil for growing or needing growing plant.
Formula (I) compound represented may be deposited with different stereoisomer or optical isomer or tautomeric form ?.The present invention includes the mixture and isotope form example of all such isomers and tautomer and its various ratios Such as deuterated compound.
It is worth noting that, the stereochemical structure of oxime part present in oximido-terazole derivatives of the present invention include (E) or (Z) isomers, and these stereoisomers constitute a part of the invention.
In the presence of the compound of the present invention can be in the form of tautomer, in where applicable, institute above and below It states compound and is interpreted as also including corresponding tautomeric form, even if these tautomeric forms are not bright in each case Really refer to.
The structure that the general formula that there is the compound of isotope enrichment the present invention to provide is described, in addition to one or more atom quilts It is replaced with selected atomic weight or the atom of mass number.The Exemplary isotopes that can be introduced into the compounds of this invention include hydrogen, Carbon, nitrogen, oxygen, phosphorus, sulphur, fluorine and chlorine isotope, such as2H,3H,11C,13C,14C,15N,17O,18O,18F,31P,32P,35S,36Cl With125I。
Any asymmetric atom (for example, carbon etc.) of disclosed compound of present invention can be enriched with racemic or enantiomer Form exist, such as (R)-, (S)-or (R, S)-configuration exist.
Content noted earlier only outlines certain aspects of the invention, but be not limited to these aspect and it is otherwise in Appearance will make more specific complete description below.
Detailed description of the invention
Definition and general terms
It will now be described in more detail certain embodiments of the present invention, the example is by the structural formula and chemical formula explanation that are appended.This Invention is intended to cover all replacement, modification and equivalent technical solutions, they are included in the present invention defined such as claim In range.Those skilled in the art will appreciate that many can be used in similar or equivalent method and material of the present invention The practice present invention.The present invention is not limited to method of the present invention and material.In document, patent and the similar material combined One or more or contradict in the case where (including but not limited to defined in term, term application, institutes different from the application Technology of description, etc.), it is subject to the application.
It will further be appreciated that certain features of the invention, be it is clearly visible, carry out in a number of independent embodiments Description, but can also provide in combination in a single embodiment.Conversely, various features of the invention, for brevity, It is described in a single embodiment, but can also be individually or with the offer of any suitable sub-portfolio.
Unless otherwise stated, all scientific and technical terminologies used in the present invention have with those skilled in the art of the invention's It is generally understood identical meaning.All patents of the present invention and public publication are integrally incorporated this hair by reference It is bright.
Unless otherwise stated, following definition used in the present invention should be applied.For purposes of the present invention, chemical element With the periodic table of elements CAS editions, and " Handbook of Chemistry and Physics ", the 75th edition, 1994 is consistent.In addition, organic chemistry General Principle can With reference to " Organic Chemistry ", Thomas Sorrell, University Science Books, Sausalito: 1999, and " March's Advanced Organic Chemistry " by Michael B.Smith and Jerry Description in March, John Wiley&Sons, New York:2007, entire contents are incorporated by reference into the present invention.
There is apparent conflict unless otherwise indicated or in context, the article " one " used herein, " one (kind) " " described " is intended to include "at least one" or " one or more ".Therefore, these articles used herein refer to one or The article of more than one (i.e. at least one) object.For example, " component " refers to one or more components, it is possible to have more than one Component be taken into account in the embodiment of the embodiment and use or use.
Term "comprising" is open language, that is, includes content specified by the present invention, but be not precluded otherwise Content.
" stereoisomer " refers to identical chemical constitution, but the spatially different change of arrangement mode of atom or group Close object.Stereoisomer includes enantiomter, diastereoisomer, conformer (rotational isomer), geometric isomer (cis/trans) isomers, atropisomer, etc..
" enantiomter " refers to two isomers that cannot be overlapped but be mutually mirror of a compound.
" diastereoisomer " refer to there are two or multiple chiral centres and its molecule not alloisomerism of mirror image each other Body.Diastereoisomer has different physical properties, such as fusing point, boiling point, spectral property and reactivity.Diastereoisomer is mixed Such as electrophoresis and chromatography, such as HPLC can be operated by high resolution analysis to separate by closing object.
Stereochemical definitions used in the present invention and rule generally follow S.P.Parker, Ed., McGraw-Hill Dictionary of Chemical Terms(1984)McGraw-Hill Book Company,New York；and Eliel,E.and Wilen,S.,“Stereochemistry of Organic Compounds”,John Wiley&Sons, Inc.,New York,1994。
Many organic compounds exist with optical active forms, i.e., they, which have, rotates the plane of linearly polarized light Ability.When describing optically active compound, indicate molecule about one or more hand using prefix D and L or R and S The absolute configuration at property center.Prefix d and l or (+) and (-) are the symbols for the rotation of linearly polarized light caused by appointed compound, Wherein (-) or l indicate that compound is left-handed.Prefix is (+) or the compound of d is dextrorotation.A kind of specific alloisomerism Body is enantiomter, and the mixture of this isomers is referred to as enantiomeric mixture.The 50:50 mixture of enantiomter Referred to as racemic mixture or racemic modification, when chemical reaction or in the process without stereoselectivity or stereospecificity when, It may occur in which such case.
As described in the invention, the compound of the present invention can be optionally replaced one or more substituent groups, such as General formula compound above, or as example special inside embodiment, subclass, and a kind of compound that the present invention is included. It should be appreciated that this term can be used interchangeably " optionally replacing " this term with " substituted or non-substituted ".In general, art " substituted " the one or more hydrogen atoms indicated in given structure of language are replaced specific substituent group.Unless other aspect tables Bright, an optional substituent group can be replaced at various substitutable position of that group.When in given structural formula not Only a position can be replaced one or more substituent groups selected from specific group, then substituent group can identical or differently Replace at various locations.Wherein the substituent group can be, but be not limited to, deuterium, fluorine, chlorine, bromine, iodine, cyano, hydroxyl, nitre Base, amino, carboxyl, alkyl, alkoxy, alkoxyalkyl, alkyloxy-alkoxy, alkoxy alkylamino, aryloxy group, heteroaryl oxygen Base, heterocycle oxygroup, alkoxy aryl, heteroarylalkoxy, heterocyclylalkoxy, cycloalkyl alkoxy, alkylamino, alkylamino Alkyl, alkylamino alkylamino, cycloalkyl amino, amino-n-cycloalkyl, alkylthio group, halogenated alkyl, halogenated alkoxy, hydroxyl replace Alkyl, hydroxyl replace alkylamino, cyano replace alkyl, cyano replace alkoxy, cyano replace alkylamino, amino Substituted alkyl, alkyl acyl, miscellaneous alkyl, naphthenic base, cycloalkenyl, cycloalkyl-alkyl, heterocycle, heterocyclylalkyl group, heterocycle Acyl group, aryl, aryl alkyl, fragrant amino, heteroaryl, heteroaryl alkyl, heteroaryl amino, amide groups, sulfonyl, aminosulfonyl Base etc..
In addition, it is necessary to explanation, unless otherwise explicitly point out, in the present invention used by describing mode " each ... independently be " and " ... be each independently " and " ... independently be " can be interchanged, and shall be understood in a broad sense, both may be used To refer among the different groups, does not influence mutually, can also indicate in phase between expressed specific option between the same symbol In same group, do not influenced mutually between expressed specific option between the same symbol.
It is disclosed in the substituent group of each section of this specification, disclosed compound of present invention according to radical species or range.It is special It does not point out, the present invention includes each independent sub-combinations thereof of each member of these radical species and range.For example, term “C1-C6Alkyl " or " C1-6Alkyl " refers in particular to the methyl being individually disclosed, ethyl, C3Alkyl, C4Alkyl, C5Alkyl and C6Alkyl.
Terminology used in the present invention " alkyl " or " alkyl group ", indicate contain 1 to 20 carbon atom, the straight chain of saturation or Branch univalent hydrocarbyl group；Replaced the substituent group that wherein alkyl group is optionally described by one or more present invention. Unless otherwise detailed instructions, alkyl group contains 1-20 carbon atom.In one embodiment, alkyl group contains 1-12 carbon Atom；In one embodiment, alkyl group contains 1-8 carbon atom；In another embodiment, alkyl group contains 1-6 A carbon atom；In yet another embodiment, alkyl group contains 1-4 carbon atom；Also in one embodiment, alkyl group contains There is 1-3 carbon atom.
The example of alkyl group includes, but is not limited to, methyl (Me ,-CH3), ethyl (Et ,-CH2CH3), n-propyl (n- Pr、-CH2CH2CH3), isopropyl (i-Pr ,-CH (CH3)2), normal-butyl (n-Bu ,-CH2CH2CH2CH3), isobutyl group (i-Bu ,- CH2CH(CH3)2), sec-butyl (s-Bu ,-CH (CH3)CH2CH3), tert-butyl (t-Bu ,-C (CH3)3), n-pentyl (- CH2CH2CH2CH2CH3), 2- amyl (- CH (CH3)CH2CH2CH3), 3- amyl (- CH (CH2CH3)2), 2- methyl -2- butyl (- C (CH3)2CH2CH3), 3- methyl -2- butyl (- CH (CH3)CH(CH3)2), 3- methyl-1-butyl (- CH2CH2CH(CH3)2), 2- first Base -1- butyl (- CH2CH(CH3)CH2CH3), etc..
Term " alkylidene " expression removes the two of two obtained saturations of hydrogen atom from the linear chain or branched chain hydrocarbon of saturation Valency alkyl group.Unless otherwise detailed instructions, alkylidene group contains 1-12 carbon atom.In one embodiment, alkylidene Group contains 1-8 carbon atom；In one embodiment, alkylidene group contains 1-6 carbon atom；In another embodiment In, alkylidene group contains 1-4 carbon atom；In yet another embodiment, alkylidene group contains 1-3 carbon atom；Also exist In one embodiment, alkylidene group contains 1-2 carbon atom.Such example includes methylene (- CH2), ethylidene (- CH2CH2), propylidene (- CH2CH2CH2) ,-CH (CH3)CH2,-C (CH3)2,-CH2CH2CH(CH3)-,-CH2CH2C (CH3)2, etc..
Term " alkenyl " indicates the linear chain or branched chain monovalent hydrocarbon containing 2-12 carbon atom, wherein at least one insatiable hunger And site, that is, there is a carbon-to-carbon sp2Double bond, wherein the alkenyl group can be retouched optionally by one or more present invention Replaced the substituent group stated comprising the positioning of " cis " and " tans ", or the positioning of " E " and " Z ".In one embodiment, Alkenyl group includes 2-8 carbon atom；In another embodiment, alkenyl group includes 2-6 carbon atom；In another embodiment party In case, alkenyl group includes 2-4 carbon atom.The example of alkenyl group includes, but is not limited to, vinyl (- CH=CH2), Allyl (- CH2CH=CH2), acrylic (CH3- CH=CH-), the cyclobutenyl (CH of oxo3- C (=O)-CH=CH-) etc..
The obtained divalent alkylene base base of two hydrogen atoms is removed in term " alkenylene " expression from linear chain or branched chain alkene Group.Unless otherwise detailed instructions, alkenylene group contains 1-12 carbon atom.In one embodiment, alkenylene group contains 1-8 carbon atom；In one embodiment, alkenylene group contains 1-6 carbon atom；In another embodiment, alkenylene Group contains 1-4 carbon atom；In yet another embodiment, alkenylene group contains 1-3 carbon atom；Also in an embodiment In, alkenylene group contains 1-2 carbon atom.Such example includes-CH=CH- ,-CH=CH-CH2,-CH=CH-CH (CH3)-,-CH=CH-C (CH3)2, etc..
Term " alkynyl " indicates the linear chain or branched chain monovalent hydrocarbon containing 2-12 carbon atom, wherein at least one carbon- Tri- key of carbon sp.In one embodiment, alkynyl group includes 2-8 carbon atom；In another embodiment, alkynyl group includes 2-6 carbon atom；In yet another embodiment, alkynyl group includes 2-4 carbon atom.The example of alkynyl group includes, but simultaneously It is not limited to ,-C ≡ CH ,-CH2-C≡CH、-CH2-C≡CCH3、-CH2CH2-C≡CH、-CH2-C≡CCH2CH3Etc..
Term " alkoxy " indicates that alkyl group is connected by oxygen atom with molecule rest part, and wherein alkyl group has Meaning as described in the present invention.The example of alkoxy base includes, but is not limited to, methoxyl group (MeO ,-OCH3), ethyoxyl (EtO、-OCH2CH3), 1- propoxyl group (n-PrO, n- propoxyl group ,-OCH2CH2CH3), 2- propoxyl group (i-PrO, i- propoxyl group ,- OCH(CH3)2) etc..
Term " alkyl amino " or " alkylamino " include " N- alkyl amino " and " N, N- dialkyl amido ", wherein amino base Group is separately replaced one or two alkyl group.Some of embodiments are that alkyl amino is one or two C1-6Alkyl is connected to the alkylamino group of the lower level on nitrogen-atoms.Other embodiment is that alkyl amino is C1-3's The alkylamino group of lower level.Suitable alkylamino group can be alkyl monosubstituted amino or dialkyl amido, such reality Example includes, but is not limited to, N- methylamino, N- ethylamino, N, N- dimethylamino, N, N- lignocaine etc..
Term " alkylthio group " refers to that the alkyl of linear chain or branched chain is connected on the sulphur atom of divalent, and wherein alkyl group has such as Meaning of the present invention.The example of alkylthio radicals includes, but is not limited to ,-SCH3、-SCH2CH3、-SCH2CH2CH3Deng Deng.
Term " halogen " refers to fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
Term " halogenated alkyl " indicates alkyl group replaced one or more halogen atoms.
Term " halogenated alkoxy " indicates alkoxy base replaced one or more halogen atoms.
Term " halogenated alkylamino " indicates alkylamino radicals replaced one or more halogen atoms.
Term " halogenated alkylthio " indicates alkylthio radicals replaced one or more halogen atoms.
Term " naphthenic base " indicates containing 3-12 carbon atom, monovalent or multivalence saturation monocyclic, bicyclic or tricyclic body System.In one embodiment, naphthenic base includes 3-10 carbon atom；In another embodiment, naphthenic base includes that 3-8 carbon is former Son；In yet another embodiment, naphthenic base includes 3-6 carbon atom.The group of naphthene base is optionally by one or more sheets It invents replaced described substituent group.Such example includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopenta, hexamethylene Base, suberyl, cyclooctyl, cyclononyl, cyclodecyl, ring undecyl, cyclo-dodecyl, etc.；Or naphthenic base includes, but simultaneously It is not limited to having structure:
Term " cycloalkenyl " indicates containing 3-12 carbon atom, monovalent or multivalence monocyclic, bicyclic or tricyclic system, until It less include a carbon-carbon double bond, the ring system is nonaromatic.In one embodiment, cycloalkenyl includes that 3-10 carbon is former Son；In another embodiment, cycloalkenyl includes 3-8 carbon atom；In yet another embodiment, cycloalkenyl includes 3-6 carbon Atom.The cycloalkenyl groups are optionally replaced one or more substituent groups described in the invention.Such example packet It includes, but is not limited to, cyclobutane base, cyclopentenyl, cyclohexenyl group, cyclohexadienyl etc.
Term " heterocycle " and " heterocycle " are used interchangeably here, all refer to the saturation comprising 3-15 annular atom or portion Divide unsaturated monocyclic, bicyclic or tricyclic, does not include aromatic rings, and at least one annular atom in monocyclic, bicyclic or tricyclic wherein Selected from nitrogen, sulphur and oxygen atom.Unless otherwise stated, heterocycle can be carbon-based or nitrogen base, and-CH2Group can be optionally It is substituted by-C (=O)-.The sulphur atom of ring can optionally be oxidized to S- oxide.The nitrogen-atoms of ring can be optionally by oxygen It is melted into N- oxygen compound.The example of heterocycle includes, but are not limited to Oxyranyle, azelidinyl, oxetanylmethoxy, sulphur Heterocycle butyl, pyrrolidinyl (such as 2- pyrrolidinyl), 2- pyrrolinyl, 3- pyrrolinyl, pyrazolidinyl, imidazolinyl, imidazoles Alkyl, tetrahydrofuran base, dihydrofuryl, tetrahydro-thienyl, dihydrothiophene, 1,3- dioxy cyclopenta, two sulphur cyclopenta, four Hydrogen pyranose, dihydro pyranyl, 2H- pyranose, 4H- pyranose, tetrahydro thiapyran base, piperidyl (2- piperidyl, 3- piperidyl, 4- piperidyl), morpholinyl, thio-morpholinyl, (1- oxo)-thio-morpholinyl, (1,1- dioxo)-thio-morpholinyl, piperazine Base, dioxanes base, dithianyl, thiophene oxane base, high piperazine base, homopiperidinyl, oxepane alkyl, thia cycloheptyl alkyl, 2- Oxa- -5- azabicyclo [2.2.1] hept- 5- base, tetrahydro pyridyl.- CH in heterocycle2The reality that group is replaced by-C (=O)- Example includes, but are not limited to 2- oxo-pyrrolidine base, oxo -1,3-thiazoles alkyl, 2- piperidone base, 3,5- dioxy piperazine piperidinyls. The example that sulphur atom is oxidized in heterocycle includes, but are not limited to sulfolane base, 1,1- dioxothiomorpholinyl.It is described miscellaneous Cyclic groups are optionally replaced one or more substituent groups described in the invention.
Contain one or more degrees of unsaturation in " unsaturated " the expression group of term as used in the present invention.
Term " hetero atom " refers to O, S, N, P and Si, the form including any oxidation state of N, S and P；Primary, secondary, tertiary amine and season The form of ammonium salt；Or the substituted form of hydrogen in heterocycle on nitrogen-atoms, for example, N is (as in 3,4- dihydro-2 h-pyrrole base N), NH (as the NH in pyrrolidinyl) or NR (NR in pyrrolidinyl replaced as N-).
Term " aryl " indicates the monocycle containing 6-14 annular atom or 6-12 annular atom or 6-10 annular atom, double The carbocyclic ring system of ring and tricyclic, wherein at least one ring system be it is aromatic, wherein each ring system include 3-7 original Molecular ring, and there are one or more attachment points to be connected with the rest part of molecule.Term " aryl " can be with term " fragrance Ring " is used interchangeably.The example of aryl group may include phenyl, indenyl, naphthalene and anthryl.The aryl group is optionally by one Replaced a or multiple substituent groups described in the invention.
Monocycle of term " heteroaryl " expression containing 5-12 annular atom or 5-10 annular atom or 5-6 annular atom, Bicyclic and three-ring system, wherein at least one ring system are aromatic, and at least one ring system includes one or more miscellaneous Atom, wherein each ring system includes 5-7 former molecular ring, and has one or more attachment points and molecule rest part It is connected.Term " heteroaryl " can be used interchangeably with term " hetero-aromatic ring " or " heteroaromatics ".The heteroaryl groups are appointed Selection of land is replaced one or more substituent groups described in the invention.In one embodiment, 5-10 original is molecular miscellaneous Aryl includes 1,2,3 or 4 hetero atom for being independently selected from O, S and N.
The example of heteroaryl groups includes, but is not limited to, 2- furyl, 3- furyl, TMSIM N imidazole base, 2- imidazole radicals, 4- imidazole radicals, 5- imidazole radicals, 3- isoxazolyl, 4- isoxazolyl, 5- isoxazolyl, 2- oxazolyl, 4- oxazolyl, 5- oxazole Base, N- pyrrole radicals, 2- pyrrole radicals, 3- pyrrole radicals, 2- pyridyl group, 3- pyridyl group, 4- pyridyl group, 2- pyrimidine radicals, 4- pyrimidine radicals, 5- Pyrimidine radicals, pyridazinyl (such as 3- pyridazinyl), 2- thiazolyl, 4- thiazolyl, 5- thiazolyl, tetrazole radical (such as 5- tetrazole radical), triazole Base (such as 2- triazolyl and 5- triazolyl), 2- thienyl, 3- thienyl, pyrazolyl, isothiazolyl, 1,2,3-oxadiazoles base, 1, 2,5- oxadiazoles bases, 1,2,4- oxadiazoles base, 1,2,3-triazoles base, 1,2,3- thio biphosphole base, 1,3,4- thio biphosphole base, 1, 2,5- thio biphosphole bases, pyrazinyl, 1,3,5-triazines base, pyrimidine ketone group, pyriconyl；It also include below bicyclic, but never It is bicyclic to be limited to these: benzimidazolyl, benzofuranyl, benzo tetrahydrofuran base, benzothienyl, indyl (such as 2- indoles Base), etc..
In one embodiment, heteroaryl groups are following subformula:
Etc..
Term " aryl alkyl " refers to that alkyl is substituted with aryl, and is connected by alkyl group with the rest part of molecule；Its Middle alkyl and aryl group have meaning as described in the present invention.
Term " heteroaryl alkyl " refers to that alkyl is substituted by heteroaryl, and passes through the rest part phase of alkyl group and molecule Even；Wherein alkyl or heteroaryl groups have meaning as described in the present invention.
Term " cycloalkyl-alkyl " refers to that alkyl is substituted by cycloalkyl, and passes through the rest part phase of alkyl group and molecule Even；Wherein alkyl or cycloalkyl group has meaning as described in the present invention.
Term " heterocyclylalkyl group " refers to that alkyl is replaced by heterocycle, passes through the rest part phase of alkyl group and molecule Even；Wherein alkyl or heterocyclyl groups have meaning as described in the present invention.
As described herein, attachment point can be connected any attachable position on ring with molecule rest part；Such as formula a In have an attachment point that can be connected with molecule rest part, as shown in formula b, formula c and formula d.It is attached when ring is bicyclic or polycyclic Point can be connected with molecule rest part any attachable position on each ring；As there is an attachment point can be in formula e Molecule rest part is connected, as shown in formula f, formula g, formula h, formula i and formula j.
As described herein,It indicates that the compound comprising carbon-to-nitrogen double bon can be Z configuration, is also possible to E configuration, Or indicate the mixture of Z configuration and E configuration.
When the compound of the present invention includes an acid moieties, the salt of compound of the present invention, including derived from alkali gold Belong to or those of alkaline-earth metal and is derived from those of ammonia and amine.Preferred cation includes sodium, potassium, magnesium and has chemistry Formula N+(R19R20R21R22) ammonium cation, wherein R19、R20、R21And R22Independently selected from hydrogen, C1-C6Alkyl and C1-C6Hydroxyl alkane Base.The salt of compound with chemical formula (I) can by with metal hydroxides (such as sodium hydroxide) or amine (such as ammonia, Trimethylamine, diethanol amine, 2- methyl mercapto propylamine, diallyl amine, 2- butoxyethylamine, morpholine, ring lauryl amine or benzylamine) to tool There is the compound of chemical formula (I) to be handled to prepare.
When the compound of the present invention includes an alkali part, acceptable salt can be formed by organic acid and inorganic acid, Such as acetic acid, propionic acid, lactic acid, citric acid, tartaric acid, succinic acid, fumaric acid, maleic acid, malonic acid, mandelic acid, malic acid, neighbour Phthalic acid, hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, methanesulfonic acid, naphthalene sulfonic acids, benzene sulfonic acid, toluenesulfonic acid, camphorsulfonic acid with And similarly known acceptable acid.
Composition and preparation of the compounds of this invention and application thereof
The present invention provides a kind of fungicide composite, the composition includes: a effective amount of logical as herein defined Formula (I) compound acceptable carrier (support), carrier or filler (filler) as active constituent and agriculturally.
According to the present invention, term " carrier " indicates a kind of natural or synthesis organic or inorganic compound, with formula (I) Active compound or joint so that reactive compound is easier to be applied to plant, especially to the part of plant. Therefore, this carrier is usually inert, and should be agriculturally acceptable.Carrier can be solid or liquid.Suitable load The example of body include clay, natural or synthetic silicate, silica, resin, wax, solid fertilizer, water, alcohols (especially Butanol), organic solvent, mineral oil and vegetable oil and its derivative.Also the mixture of such carrier can be used.
Composition of the invention can also include other components.Specifically, the composition also may include surfactant. The surfactant can be ionic or non-ionic emulsifier, dispersing agent or wetting agent or these surfactants Mixture.Such as, it may include polyacrylate, lignosulphonates, sulfocarbolate or naphthalene sulfonate, ethylene oxide and fatty alcohol or With fatty acid or with the condensation polymer of fatty amine, substituted phenol (especially alkyl phenol or aryl phenol), the salt of sulfosuccinate, ox Sulfonic acid (especially taurine Arrcostab), the phosphate of oxyethylated alcohol or phenol, polyalcohol aliphatic ester and The derivative of above compound comprising sulfate radical, sulfonate radical or phosphonate functional group.In general, when reactive compound and/or lazy When medium reagent that is that property carrier is insoluble in water and being applied is water, it is necessary to which there are at least one surfactants.Preferably, With the poidometer of composition, the content of surfactant is 5-40 weight %.
Optionally, may also include other components, for example, protective colloid, adhesive, thickener, thixotropic agent, bleeding agent, Stabilizer, chelating agent.It more generally, can be by the reactive compound and any solid or liquid that meet common preparation technique Additive is combined.
In general, composition of the invention may include the reactive compound of 0.05-99 weight %, preferably 10-70 weight %.
Composition of the invention can in a variety of manners using and can be used for various preparations, such as aerosol dispersing agent, glue Capsule suspending agent (capsule suspension), harl concentrating agents, can dusting powder, emulsifiable concentrating agents, oil-in-water emulsion, oil Packet aqueous emulsion, encapsulated granula, fine grained agent, the flowable concentrating agents for seed treatment, gas (under pressure) preparation, gas hair Raw agent, granule, hot mist concentrating agents, big granula, fine granule, oily dispersible powder, the flowable concentrating agents of oily compatibility, oil are mixed Insoluble liquid, paste, plant spillikin, the seed for doing kind of a pulvis for processing, coated pesticidal, soluble concentrating agents, solubility Pulvis, the solution for seed treatment, suspension concentrating agents (flowable concentrating agents), ultra-low volume (ULV) liquid, ultra-low volume (ULV) granula or tablet, water dispersible pulvis, water-soluble granule or tablet for slurries processing, use can be dispersed in suspending agent, water In the water solube powder and wettability pulvis of seed treatment.These compositions not only include that will use suitable equipment (example Such as sprayer or dusting equipment) it is applied to the composition on processed plant or seed, and be included in and be applied to crops The commercial composite for the concentration that must be diluted before.
Preparation can be prepared by mode known to script, such as by the way that active constituent and at least one is following conventional It is prepared by material mixing: expanding material, surfactant, solvent or diluent, adjuvant, emulsifier, dispersing agent and/or binder or Fixative, wetting agent, waterproofing agent, (if applicable) desiccant and UV stabilizer, and (if applicable) dyestuff With pigment, defoaming agent, preservative, inorganic and organic thickening agent, adhesive, gibberellin and other processing aids and water.According to Preparation type to be prepared needs other procedure of processings, such as wet grinding, dry grinding and granulation.
In solid pharmaceutical preparation, the vegetalitas such as soy meal, wheat flour powder, diatomite, apatite, gypsum, cunning can be used Organic and inorganic compounds such as the minerals such as stone, bentonite, pyrophillite, clay micropowder, sodium benzoate, urea, sodium sulphate etc. Additive and/or carrier.
In liquid preparation, can be used the petroleum distillates such as kerosene, dimethylbenzene and solvent naphtha, hexamethylene, cyclohexanone, Dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloro ethylene, methyl iso-butyl ketone (MIBK), mineral oil, vegetable oil, water equal solvent.
It is a further object of the invention to provide a kind of method of control plant, the plant pathogenic fungi of crop or seed, It is characterized in that, by agriculturally effectively and substantially non-phytotoxic amount microbicide compositions of the invention with seed treatment, Leaf portion applies, stem applies, be impregnated with or the mode of trickle irrigation application (chemistry applies) is applied to following part: seed, plant or plant Object fruit, or planted or intended the soil or inert base (such as inorganic matrix, such as sand, asbestos, mineral wool of planting plants； Expand minerals, such as perlite, vermiculite, zeolite or expanded clay), float stone, pyroclast substance or material, synthesis it is organic Matrix (such as polyurethane), organic substrate (such as peat, compost, trees waste product (such as coconut husk, wood-fibred or sawdust, tree Skin)) or fluid matrix (such as floating hydroponic system, nutrient film techinique, gas carrying agent system).
The amount of application of fungicide of the present invention according to meteorological condition, dosage form, Dressing date, method of administration, application place, Control object disease, object crop etc. are different and different, but usually every 1 hectare of effective component chemical combination object amount is 0.01~1000g, excellent It is selected as 10~100g.
Term administering is in plant to be processed " it is understood to refer to for purposes of the present invention, it can be by following various Processing method applies the composition pesticide as present subject matter:
To liquid of the aerial part of the plant spraying comprising one of the composition；
It dusts in the surrounding plants, particle or powder is incorporated into soil, is spraying and when the plant is trees In the case where injected or smeared；
By the plant protection mixture comprising one of the composition, coating is carried out to the seed of the plant or film applies It covers.
Method of the invention can be healing, prevention or the method eradicated.
It is such as but not limited to the crop of composition pesticide or combined treatment of the invention, such as vine, can also be Cereal, vegetables, clover, soybean, commercially available garden crop, turf, trees or gardening plant.
Processing method of the invention can also be used to handling propagation material (such as stem tuber or rhizome) and seed, seedling or Transplant seedling and plant or transplanting plant.The processing method can also be used for processing root.Processing method of the invention can also be used for Handle the aerial part of plant, such as the trunk in relation to plant, stem or stalk, leaf, flower and fruit.
Can with or can have cotton, flax, liana, fruit or vegetables with the plant that method of the invention is protected Crop, as (for example, pip fruit, such as apple and pears, there are also drupe, such as apricot, almond for rosaceae (Rosaceae sp.) (almond) and peach), tea sugarcane scarabaeidae (Ribesioidae sp.), Juglandaceae (Juglandaceae sp.), Betulaceae (Betulaceae sp.), Anacardiaceae (Anacardiaceae sp.), Fagaceae (Fagaceae sp.), Moraceae (Moraceae sp.), Oleaceae (Oleaceae sp.), Actinidiaceae (Actinidaceaesp.), Lauraceae (Lauraceae Sp.), Musaceae (Musaceae sp.) (such as Banana tree and powder bajiao banana (plantins)), Rubiaceae (Rubiaceae Sp.), Theaceae (Theaceae sp.), Sterculiaceae (Sterculiceae sp.), Rutaceae (Rutaceae sp.) (such as Lemon, orange and grape fruit)；Solanaceae (Solanaceae sp.) (such as tomato), Liliaceae (Liliaceae sp.) are purple Aster section (Asteraceae sp.) (such as lettuce), Umbelliferae (Umbelliferae sp.), Cruciferae (Cruciferae Sp.), Chenopodiaceae (Chenopodiaceae sp.), Curcurbitaceae (Cucurbitaceae sp.), Papilionaceae (Papilionaceae sp.) (such as pea), rosaceae (Rosaceae sp.) (such as strawberry)；Chief crop, such as grass Section (Graminae sp.) (such as corn, lawn or cereal such as wheat, rice, barley and triticale), aster section (Asteraceae Sp.) (such as sunflower), crucifer (such as rape), pulse family (Fabacae sp.) (such as peanut), Papilionaceae (Papilionaceae sp.) (such as soybean), Solanaceae (Solanaceae sp.) (such as potato), Chenopodiaceae (Chenopodiaceae sp.) (such as beet root)；Garden crop and forestry crop；And the genetic changec of these crops Homologue.
In the disease of controllable plant or crop by the method for the invention, it can be mentioned that:
Powdery mildew, such as:
Powdery mildew (Blumeria diseases) is caused by such as wheat powdery mildew (Blumeria graminis)；
Podosphaera disease (Podosphaera diseases), by for example white cross hair list softgel shell (Podosphaera Leuco-tricha) cause；
Sphaerotheca disease (Sphaerotheca diseases), by such as Siberian cocklebur monofilament shell (Sphaerotheca Fuliginea caused by)；
Uncinula disease (Uncinula diseases), such as caused by grape fishing line shell (Uncinula necator)； Rust, such as:
Glue Rust is sick (Gymnosporangium diseases), by such as absorption unit rest fungus (Gymnosporangium Sabinae) cause；
Hunchbacked spore rust (Hemileia diseases), is drawn by such as coffee rust (Hemileia vastatrix) It rises；
Phakopsora disease (Phakopsora diseases), by such as Phakopsora pachyrhizi (Phakopsora Pachyrhizi) or mountain horseleech layer rest fungus (Phakopsora meibomiae) causes；
Puccinia disease (Puccinia diseases), such as drawn by Puccinia recondita (Puccinia recondite) It rises；
Uromyces disease (Uromyces diseases), by such as wart top uromyce (Uromyces Appendiculatus) cause；Oomycetes disease (Oomycete diseases), such as:
Bremia disease (Bremia diseases) is obstructed mould (Bremia lactucae) by such as lettuce disk and is caused；
Peronospora disease (Peronospora diseases), by such as pea downy mildew (Peronospora pisi) or rape Downy mildew (P.brassicae) causes；
Phytophthora disease (Phytophthora diseases), by such as phytophthora infestans (Phytophthora Infestans) cause；
Plasmopara disease (Plasmopara diseases), by the raw uniaxial mould (Plasmopara of such as grape Viticola) cause；
Pseudoperonospora disease (Pseudoperonospora diseases), by such as humulus grass downy mildew Caused by (Pseudoperonospora humuli) or cucumber downy mildew (Pseudoperonospora cubensis)；
Pythium disease (Pythium diseases), is caused by such as Pythium ultimum (Pythium ultimum)；
Leaf spot, leaf blotch and leaf blight, such as:
Alternaria disease (Alternaria diseases), such as drawn by alternaria solani sorauer (Alternaria solani) It rises；
Cercospora disease (Cercospora diseases), it is raw tail spore (Cercospora beticola) by such as beet Cause；
Chrysosporium disease (Cladiosporum diseases), such as by melon fruit fly (Cladiosporium Cucumerinum) cause；
Cochliobolus disease (Cochliobolus diseases), such as by standing grain cochliobolus (Cochliobolus Sativus) cause；
Colletotrichum disease (Colletotrichum diseases) pierces disk spore (Colletotrichum by such as beans Lindemuthianum) cause；
Olive peacock's eye disease disease (Cycloconium diseases), by such as olive peacock plaque (Cycloconium oleaginum) causes；
Beancurd sheet shell bacterium layer is sick (Diaporthe diseases), is drawn by seat shell between such as citrus (Diaporthe citri) It rises；
Elsinoe disease (Elsinoe diseases), by such as citrus Elsinochrome (Elsinoe fawcettii) Cause；
Long spore belongs to sick (Gloeosporium diseases), by for example happy long spore (Gloeosporium of colour disk Laeticolor) cause；
Small cluster shell belongs to sick (Glomerella diseases), by such as GLOMERFLLA CINGULATA (Glomerella cingulata) Cause；
Ball seat Pseudomonas is sick (Guignardia diseases), by such as grape Guignardia (Guignardia Bidwellii) cause；
Leptosphaeria disease (Leptosphaeria diseases), by such as Cruciferae ball cavity bacteria (Leptosphaeria maculans), the withered ball cavity bacteria (Leptosphaeria nodorum) of grain husk cause；
Rice blast (Magnaporthe diseases) is caused by such as rice blast fungus (Magnaporthe grisea)；
Mycosphaerella disease (Mycosphaerella diseases), by such as standing grain green-ball chamber bacterium (Mycosphaerella Graminicola), peanut spherical cavity bacterium (Mycosphaerella arachidicola), banana secret note tikka bacterium Caused by (Mycosphaerella fijiensis)；
Septoria disease (Phaeosphaeria diseases), by such as phaeosphaeria nodorum (Phaeosphaeria Nodorum) cause；
Pyrenophora disease (Pyrenophora diseases), such as drawn by circle nuclear cavity bacteria (Pyrenophora teres) It rises；
Ramularia disease (Ramularia diseases), by for example pungent strutting every spore (Ramularia collo- Cygni) cause；
Beak genuss disease (Rhynchosporium diseases), by such as rye beak spore (Rhynchosporium Secalis) cause；
Septoria disease (Septoria diseases), by such as Septoria apii (Septoria apii) or tomato Septoria musiva (Septoria lycopersici) causes；
Core coral bacterium is sick (Typhula diseases), is caused by for example yellowish pink core coral bacterium (Typhula incarnata)；
Venturia disease (Venturia diseases), such as drawn by venturia inaequalis (Venturia inaequalis) It rises；
Root disease and stem disease, such as:
Photovoltaicing leather bacteria disease (Corticium diseases), is drawn by such as standing grain photovoltaicing leather bacteria (Corticium graminearum) It rises；
(mould) category of Fusariumsp is sick (Fusarium diseases), is drawn by for example sharp fusarium (Fusarium oxysporum) It rises；
Sturgeon shape belongs to sick (Gaeumannomyces diseases), by such as gaeumannomyce (Gaeumannomyces Graminis) cause；
Rhizoctonia disease (Rhizoctonia diseases), by such as Rhizoctonia solani Kuhn (Rhizoctonia solani) Cause；
Ta Pusi (Tapesia diseases), by such as Ta Pusi clostruidium (Tapesia acuformis) Cause；
Thiclaviopsis disease (Thielaviopsis diseases), by such as thielaviopsis sp (Thielaviopsis Basicola) cause；
Ear fringe and panicle disease, such as:
Alternaria disease (Alternaria diseases), is caused by such as rod method (Alternaria spp.)；
Aspergillosis (Aspergillus diseases) is caused by such as aspergillus flavus (Aspergillus flavus)；
Branch spore is sick (Cladosporium diseases), is caused by such as branch spore (Cladosporium spp.)；
Claviceps disease (Claviceps diseases), is caused by such as ergot (Claviceps purpurea)；
(mould) category of Fusariumsp is sick (Fusarium diseases), is drawn by such as machete fusarium (Fusarium culmorum) It rises；
Head blight (Gibberella diseases) is caused by such as Gibberella zeae (Gibberella zeae)；
Rice Gerlachia oryaae (Monographella diseases), by such as rice cloud shape bacterium (Monographella Nivalis) cause；
Smut and bunt, such as:
Axis Ustilago is sick (Sphacelotheca diseases), by such as silk axis smut (Sphacelotheca Reilinana) cause；
Tilletia disease (Tilletia diseases), by such as Tilletia caries (Tilletia caries) Cause；
Urocystis disease (Urocystis diseases), by such as hidden smut (Urocystis occulta) Cause；
Ustilago disease (Ustilago diseases), is caused by such as naked smut (Ustilago nuda)；
Fruit rot and mycosis, such as:
Aspergillosis (Aspergillus diseases) is caused by such as aspergillus flavus (Aspergillus flavus)；
Botrytis belongs to sick (Botrytis diseases), is caused by such as botrytis (Botrytis cinerea) 's；
Penicilliosis (Penicillium diseases) is drawn by such as sweet potato mould (Penicillium expansum) It rises；
Sclerotinia disease (Sclerotinia diseases), by such as sclerotinite (Sclerotinia Sclerotiorum) cause；
Verticillium disease (Verticilium diseases), by such as black and white wheel branch spore (Verticillium Alboatrum) cause；
Rotten, mouldy, withered, corrupt and samping off in seed and soil:
Alternariosis (Alternaria diseases), by such as mustard rod method (Alternaria brassicicola) Cause；
Aphanomyces disease (Aphanomyces diseases), by such as mould (Aphanomyces of pea silk capsule Euteiches) cause；
Ascochyta disease (Ascochyta diseases), is drawn by such as two born of the same parents bacterium of crystalline lens (Ascochyta lentis) It rises；
Aspergillosis (Aspergillus diseases) is caused by such as aspergillus flavus (Aspergillus flavus)；
Branch spore is sick (Cladosporium diseases), is drawn by such as multi-trunk natalensis (Cladosporium herbarum) It rises；
Cochliobolus disease (Cochliobolus diseases), such as by standing grain cochliobolus (Cochliobolus Sativus) (Conidiaform:Drechslera, Bipolaris Syn:Helminthosporium) causes；
It is sick (Colletotrichum diseases) to pierce disk spore, disk spore (Colletotrichum is pierced by such as coccoid Coccodes) cause；
(mould) category of Fusariumsp is sick (Fusarium diseases), is drawn by such as machete fusarium (Fusarium culmorum) It rises；
Head blight (Gibberella diseases) is caused by such as Gibberella zeae (Gibberella zeae)；
Shell ball spore is sick (Macrophomina diseases), by such as beans shell ball spore (Macrophomina Phaseolina) cause；
Rice Gerlachia oryaae (Monographella diseases), by such as rice cloud shape bacterium (Monographella Nivalis) cause；
Penicilliosis (Penicillium diseases) is drawn by such as sweet potato mould (Penicillium expansum) It rises；
Phoma sp disease (Phoma diseases), is caused by such as balck shank (Phoma lingam)；
Fungi point mold (Phomopsis diseases) is caused by such as soybean Phoma sp (Phomopsis sojae)；
Phytophthora disease (Phytophthora diseases), is drawn by such as Phytophthora cactorum (Phytophthora cactorum) It rises；
Nuclear cavity bacteria disease (Pyrenophora diseases), by such as wheat nuclear cavity bacteria (Pyrenophora graminea) Cause；
Pyricularia Sacc. disease (Pyricularia diseases), is caused by such as Magnaporthe grisea (Pyricularia oryzae) 's；
Pythium disease (Pythium diseases), is caused by such as Pythium ultimum (Pythium ultimum)；
Rhizoctonia disease (Rhizoctonia diseases), by such as Rhizoctonia solani Kuhn (Rhizoctonia solani) Cause；
Head mold disease (Rhizopus diseases) is caused by such as Rhizopus oryzae (Rhizopus oryzae)；
Pyrenomycetes disease (Sclerotium diseases), is drawn by such as Sclerotium rolfsii (Sclerotium rolfsii) It rises；
Septoria musiva disease (Septoria diseases), such as caused by phaeosphaeria nodorum (Septoria nodorum)；
Core coral bacterium is sick (Typhula diseases), is caused by for example yellowish pink core coral bacterium (Typhula incarnata)；
It is sick (Verticillium diseases) to take turns branch spore, by such as Verticilliumdahliae (Verticillium Dahliae) cause；
Ulcer, cracking and top dry, such as:
Nectria disease (Nectria diseases), is drawn by for example dry red shell bacterium of cancer clump (Nectria galligena) It rises；
Wilt disease, such as:
Chain sclerotinia sclerotiorum belong disease (Monilinia diseases), is drawn by such as drupe chain sclerotinia sclerotiorum (Monilinia laxa) It rises；
Leaf bubble or leaf curl, such as:
Exoascus disease (Taphrina diseases) is drawn by for example lopsided external capsule bacterium (Taphrina deformans) It rises；
Wood plant decline disease, such as:
It is sick (Esca diseases) according to section, drawn by such as head mold lattice spore bacterium (Phaeomoniella clamydospora) It rises；
Eutypa dieback (Eutypa dyeback) is caused by such as grapevine da mping-off fungi (Eutypa lata)；
Dutch elm disease (Dutch elm disease), is caused by such as silique category mite (Ceratocystsc ulmi)；
Colored and seed disease, such as:
Botrytis belongs to sick (Botrytis diseases), is caused by such as botrytis (Botrytis cinerea) 's；
Tubers disease, such as:
Rhizoctonia disease (Rhizoctonia diseases), by such as Rhizoctonia solani Kuhn (Rhizoctonia solani) Cause；
Helminthosporium disease (Helminthosporium diseases), by for example founding the compacted spore of withered length (Helminthosporium solani) causes.
The compound of the present invention can also be with one or more insecticides, fungicide, bactericide, attractant, acaricide Or pheromonal activity substance or other biologically active compounds mix.Thus obtained mixture has broad spectrum of activity. It is particularly advantageous with the mixture of other Fungicidal compounds.The mixture of compound comprising formula (I) and bactericidal compound It is also particularly advantageous with composition of the invention.
The example for the fungicide that can be suitably mixed is selected from following: benzimidazole methyl carbamate class is antifungal The compound of agent, the compound of dicarboximide class fungicide, demethylation inhibin class fungicide compound, benzamide Compound, the amine/morpholine of class fungicide kill the change of the compound of class epiphyte pharmaceutical, phosphatide biosynthesis inhibin class fungicide Close object, the compound of carboxyl acylamide fungicide, the compound of hydroxyl (2- amino -) pyrimidine fungicide, aniline pyrimidine class The compound of fungicide, the compound of N- carbanilate class fungicide, inhibin class fungicide outside quinone Compound, the compound of phenylpyrrole class fungicide, the compound of quinolines fungicide, lipid peroxidized inhibin class are killed The compound of epiphyte pharmaceutical, melanocyte biosynthesis inhibin-reduction enzyme fungicide compound, melanocyte biosynthesis inhibit Element-the compound of dehydration enzyme fungicide, the compound of hydroxy benzenes amine fungicide, squalene-epoxidase inhibin class The compound of fungicide, the compound of polyoxin class fungicide, the compound of phenyl ureas fungicide, the suppression of quinone inside Compound, the enol pyrans uronic acid antibiotics of the compound, benzamides fungicide of making plain class fungicide kill very The compound of microbial inoculum, the compound of own pyrans sugar-antibiotics fungicide, glucopyranosyl antibiotic: protein synthesizes class Compound, the glucopyranosyl antibiotic of fungicide: the compound of trehalase and inose biosynthesis class fungicide, The compound of cyanoacetamide oximes fungicide, the compound of Carbamates fungicide, oxidative phosphorylation uncoupling The compound of class fungicide, the compound of organic tin fungicide, the compound of carboxylic acids fungicide, the heteroaryl same clan kill The compound of epiphyte pharmaceutical, the compound of phosphonic acid ester fungicide, the compound of phthalamidic acid class fungicide, phentriazine class are killed The compound of epiphyte pharmaceutical, the compound of benzene sulfonamide fungicide, pyridazinone fungicide compound, thiophenecarboxamides The compound of class fungicide, the compound of pyrimidine amides fungicide, carboxyl acylamide fungicide compound, tetracycline The compound of antibiotics fungicide, the compound of thiocarbamates fungicide, benzamides fungicide Compound, the host plant defence compound of induction type fungicide, multidigit point contact activity class fungicide compound And the compound of other fungicides.
Further, the example of fungicide compound is selected from following: benomyl, carbendazim, thiophanate-methyl, corruption are mould Benefit, iprodione, vinclozolin, epoxiconazole, Fluquinconazole, Triadimenol, simeconazoles, kind bacterium azoles, triforine, cyproconazole, Difenoconazole, Flusilazole, Flutriafol, metconazole, nitrile bacterium azoles, prochloraz, propiconazole, prothioconazoles, Tebuconazole, fluorine ether azoles, Metalaxyl-M, first White spirit, mefenoxam, M 9834, benalaxyl-M, furalaxyl, ofurace, Wakil, cartap, dodemorph, butylbenzene Morpholine, tridemorph, Trimorfamid Fademorf, fenpropidin, pipron, volution bacterium amine, edifenphos, Isoprothiolane, Boscalid, pyrrole thiophene bacterium Amine, bixafen, carboxin, oxycarboxin, ethirimol, cyprodinil, diethofencarb, Fluoxastrobin, pyraclostrobin, gram glad, oxime of receipts Bacterium ester, ZEN 90160, pyribencarb, Famoxate, Fenamidone, discostrobin, enestrobin, dimoxystrobin, benzene Oxygen bacterium amine, orysastrobin, fluoxastrobin, fenpiclonil, fludioxonil, fast promise sweet smell, chloroneb, pyroquilon, tricyclazole, cyclopropyl acyl bacterium Amine, fenhexamid, pyributicarb, polyoxin, Pencycuron, match seat go out, amisulbrom, oxamides, blasticidin S-S, spring thunder Mycin, streptomysin, jinggangmeisu, cymoxanil, Propamocarb, prothiocarb, iodo propinyl butyl carbamate, fluazinam, pleasure are killed Mite, ferimzone, dinocap, dinocap, fentin acetate, oxolinic acid, hymexazol, phosphorous acid and its various salt, triethylphosphine acid Aluminium, tecloftalam, azoles bacterium piperazine, flusulfamide, diclomezine, Silthiopham, difluoro woods, dimethomorph, benzene metsulfovax, benzene metsulfovax-are different Propyl, Propineb, downy mildew go out, mandipropamid, flumorph, oxytetracycline, methasulfocarb, fluopicolide, fluopyram, I Acid benzene-S-methyl, Cupravit, copper sulphate, Kocide SD, Bordeaux mixture composition (ternary copper sulphate), elementary sulfur, maneb Zinc, Carbatene, Propineb, fervam, maneb, arasan, zineb, ziram, folpet, captan, enemy Bacterium pellet, Bravo, Guardian, cyflufenamid, the third oxygen quinoline, metrafenone, the chloro- 6- of 5- (2,4,6- trifluorophenyl) -7- (4- first Phenylpiperidines -1- base) [1,2,4] triazol [1,5-a] pyrimidine, the iodo- 3- propyl -4H-1- benzopyran-4-one of 2- butoxy -6-, 3- [5- (4- chlorphenyl) -2,3- dimethyl -3- isoxazolidinyl] pyridine, N- [1- [[[1- (4- cyano-phenyl) ethyl] sulphonyl Base] methyl] propyl] carbamic acid 4- fluorobenzene ester, N- [[(cyclo propyl methoxy) amino] [6- (difluoro-methoxy) -2,3- difluoro Phenyl] methylene] phenyl acetamide, N '-[4- [4- chloro- 3- (trifluoromethyl) phenoxy group] -2,5- 3,5-dimethylphenyl]-N- ethyl - N- methyl carboximidamide, 2- [[2- fluoro- 5- (trifluoromethyl) phenyl] sulfenyl] -2- [3- (2- methoxyphenyl) Asia -2- thiazole Alkyl] acetonitrile and N- (the chloro- 2- nitrobenzophenone of 4-)-N- ethyl -4- methyl benzenesulfonamide.
The example for the bactericide that can be suitably mixed can be selected from following: bronopol, double fluorine phenol, N-Serve, dimethyl Aminodithioformic acid nickel, kasugarnycin, octhilinone, furancarboxylic acid, terramycin, probenazole, streptomysin, tecloftalam, copper sulphate With other copper agents.
General synthesis process
In the present specification, if there are any difference between chemical name and chemical structure, structure is dominant.Generally Ground, the compound of the present invention described method can be prepared through the invention, unless there are further instruction.Following Synthetic schemes and embodiment 1-64 are for being further illustrated the contents of the present invention.
Synthetic schemes one
Target compound 5 can be prepared by synthetic schemes one, and wherein X ' is halogen, and Y has as described in the present invention Meaning.Nucleophilic substitution is occurred into for compound 1 and X '-Y and obtains compound 2, compound 2 obtains compound 3 by bromo, most Compound 3 reacts to obtain target compound 5 with compound 4 afterwards.
Synthetic schemes two
Target compound 10 can be prepared by synthetic schemes two, and wherein Y ' is alkyl, alkenyl, alkynyl, aryl, heteroaryl Base, naphthenic base, heterocycle ,-alkylene-aryl ,-alkenylene-aryl ,-alkylene-heteroaryl ,-alkenylene-heteroaryl ,-Asia Alkyl-cycloalkyl ,-alkenylene-naphthenic base ,-alkylidenyl-heterocyclic base or-alkenylene-heterocycle.By compound 1 and chloro-carbonic acid second Ester reacts to obtain compound 6, then obtains compound 7 using bromo, and then compound 7 is reacted with compound 4 is made chemical combination Hydrolysis occurs under alkaline condition and obtains compound 9 for object 8, subsequent compound 8, and compound 9 with acyl chloride reaction by can be obtained Target compound 10.
Synthetic schemes three
Target compound 11 can be prepared by synthetic schemes three, and wherein X ' is halogen, and Y has as described in the present invention Meaning.Nucleophilic substitution is occurred into for compound 9 and X '-Y and obtains target compound 11.
Embodiment
Embodiment 1 (Z)-(1- methyl-1 H- tetrazolium -5- base) (phenyl) ketone O- ((bromo- 8- isobutoxy quinoline -2- of 5- Base) methyl) oxime
The synthesis of step 1, intermediate 8- isobutoxy -2- methylquinoline
8- hydroxyl quinaldine (3.18g, 20mmol) is dissolved in DMF (20mL), potassium carbonate is successively added into solution The bromo- 2- methylpropane (3.65mL, 40mmol) of (5.52g, 40mmol) and 1-, is heated to 60 DEG C, after being stirred overnight, to reaction solution In be slowly added dropwise water (50mL) quenching reaction, ethyl acetate extracts (50mL x 3), washes through water (50mL), saturated salt solution (50mL) is washed with after anhydrous sodium sulfate drying, is concentrated to give grease (4.02g, yield 93%).
The synthesis of step 2, intermediate 5- bromo- 2- (bromomethyl) -8- isobutoxy quinoline
It is under nitrogen protection, 8- isobutoxy -2- methylquinoline (4.02g, 20mmol) and NBS (7.12g, 40mmol) is molten In CCl4In (50mL).It is heated to flowing back, and initiator A IBN (660mg, 4mmol) is added, it is filtering, dense after the reaction was continued 8h Contracting, column chromatograph (petrol ether/ethyl acetate (v/v)=20/1), obtain white solid (1.28g, 18%).
Step 3, compound (Z)-(1- methyl-1 H- tetrazolium -5- base) (phenyl) ketone O- ((bromo- 8- isobutoxy quinoline of 5- Quinoline -2- base) methyl) oxime synthesis
At room temperature, 5- bromo- 2- (bromomethyl) -8- isobutoxy quinoline (540mg, 1.5mmol) is dissolved in DMF (15mL) In, sequentially add potassium carbonate (311mg, 3mmol) and (Z)-(1- methyl-1 H- tetrazolium -5- base) (phenyl) ketoxime (305mg, 1.5mmol), after being stirred overnight, water (50mL) is added into reaction solution, ethyl acetate extracts (50mL x 3), through water (50mL) It washes, saturated salt solution (50mL) is washed after drying with anhydrous sodium sulfate, concentration, column chromatography (petrol ether/ethyl acetate (v/v)=4/ 1) white solid (408mg, 57%), is obtained.
1H NMR(400MHz,DMSO-d6): δ 8.48 (d, J=8.7Hz, 1H), 7.83 (d, J=8.4Hz, 1H), 7.70 (d, J=8.7Hz, 1H), 7.55-7.39 (m, 5H), 7.18 (d, J=8.5Hz, 1H), 5.64 (s, 2H), 4.17 (s, 3H), 3.95 (d, J=6.8Hz, 2H), 2.15 (dt, J=13.4,6.7Hz, 1H), 1.00 (d, J=6.7Hz, 6H)
LC-MS:m/z 496.20[M+H]+.
Embodiment 2 (Z)-ethyl (2- (((((1- methyl-1 H- tetrazolium -5- base) (phenyl) methylene) amino) oxygroup) first Base) quinoline-8-yl) carbonic ester
The synthesis of step 1, intermediate ethyl (2- methylquinoline -8- base) carbonic ester
It is under nitrogen protection, 8- hydroxyl quinaldine (10.35g, 65mmol) and triethylamine (36.1mL, 260mmol) is abundant It is dissolved in dry CH2Cl2In (100mL), be added catalysis equivalent DMAP, and be added dropwise chloro-carbonic acid mono ethyl ester (12.4mL, 130mmol) in reaction flask.It is added dropwise to complete, keeps temperature-resistant stirring 1h, it is molten that reaction solution is slowly poured into saturated sodium bicarbonate In liquid, ethyl acetate extracts (200mL x3), washes through water (100mL), saturated salt solution (200mL) is washed and anhydrous sodium sulfate drying Afterwards, light yellow oil 15g, thick yield 99% are concentrated to give.
The synthesis of step 2, intermediate 2- (bromomethyl) quinoline-8-yl ethyl carbonate ester
Under nitrogen protection, by ethyl (2- methylquinoline -8- base) carbonic ester (15g, 65mmol) and NBS (23.2g, 130mmol) it is dissolved in CCl4In (150mL).It is heated to flowing back, and initiator A IBN (2.13g, 13mmol) is added, the reaction was continued After 6h, filtering, concentration, column chromatograph (petrol ether/ethyl acetate (v/v)=10/1), obtain white solid (8.1g, 40%).
Step 3, compound (Z)-ethyl (2- (((((1- methyl-1 H- tetrazolium -5- base) (phenyl) methylene) amino) oxygen Base) methyl) quinoline-8-yl) and carbonic ester synthesis
At room temperature, 2- (bromomethyl) quinoline-8-yl ethyl carbonate ester (3.2g, 10.4mmol) is dissolved in DMF (30mL), Sequentially add potassium carbonate (2.07g, 15mmol) and (Z)-(1- methyl-1 H- tetrazolium -5- base) (phenyl) ketoxime (2.03g, 10mmol), after being stirred overnight, water (50mL) quenching reaction is added into reaction solution, ethyl acetate extracts (50mL x 3), through water (100mL) is washed, saturated salt solution (100mL) is washed with after anhydrous sodium sulfate drying, is concentrated to give light yellow solid (3.6g, yield 81%).
LC-MS:m/z 433.35[M+H]+.
Embodiment 3 (Z)-(1- methyl-1 H- tetrazolium -5- base) (phenyl) ketone O- ((8-hydroxyquinoline -2- base) methyl) oxime
By (Z)-ethyl (2- (((((1- methyl-1 H- tetrazolium -5- base) (phenyl) methylene) amino) oxygroup) methyl) quinoline Quinoline -8- base) carbonic ester (4.32g, 10mmol) and sodium hydroxide (2g, 50mmol) be substantially soluble in tetrahydrofuran and water (30mL, 1: 1) in mixed solution, after being warming up to 65 DEG C and being stirred overnight, reaction solution is cooled to room temperature, is concentrated under reduced pressure and removes most of four After hydrogen furans, water is added to concentrate, and (50mL x 3) is extracted with ethyl acetate, is washed through water (100mL), saturated salt solution (100mL) is washed with after anhydrous sodium sulfate drying, and it is solid to obtain white for concentration, column chromatography (petrol ether/ethyl acetate (v/v)=4/1) Body (1.55g, 43%).
1H NMR(400MHz,DMSO-d6): δ 9.72 (s, 1H), 8.35 (d, J=8.5Hz, 1H), 7.60-7.34 (m, 8H), 7.12 (d, J=7.2Hz, 1H), 5.60 (s, 2H), 4.10 (s, 3H)
LC-MS:m/z 361.20[M+H]+.
Embodiment 4 (Z) -2- (((((1- methyl-1 H- tetrazolium -5- base) (phenyl) methylene) amino) oxygroup) methyl) quinoline Quinoline -8- base 4- bromo-benzoate
Under nitrogen protection, by (Z)-(1- methyl-1 H- tetrazolium -5- base) (phenyl) ketone O- ((8-hydroxyquinoline -2- base) Methyl) oxime (150mg, 0.42mmol) and triethylamine (234uL, 0.84mmol) be substantially soluble in dry CH2Cl2In (8mL), by 4- bromo-benzoyl chloride (164uL, 0.84mmol) is added dropwise in reaction flask.It is added dropwise to complete, keeps temperature-resistant stirring 1h, it is dense Contracting, column chromatography (petrol ether/ethyl acetate (v/v)=4/1), obtain white solid (120mg, 55%).
1H NMR(400MHz,DMSO-d6): δ 8.53 (d, J=8.5Hz, 1H), 8.26 (dd, J=8.7,5.5Hz, 2H), 7.94 (d, J=1.4Hz, 1H), 7.70 (dd, J=9.0,4.6Hz, 2H), 7.59 (d, J=8.5Hz, 1H), 7.51 (dd, J= 5.4,3.0Hz,1H),7.48–7.37(m,6H),5.42(s,2H),3.93(s,3H).
LC-MS:m/z 542.65[M+H]+.
Embodiment 5 (Z)-(1- methyl-1 H- tetrazolium -5- base) (phenyl) ketone O- ((8- ((3- chlorobenzyl) oxygroup) quinoline - 2- yl) methyl) oxime
At room temperature, by (Z)-(1- methyl-1 H- tetrazolium -5- base) (phenyl) ketone O- ((8-hydroxyquinoline -2- base) methyl) Oxime (150mg, 0.42mmol) is dissolved in DMF (8mL), sequentially adds potassium carbonate (116mg, 0.84mmol) and 3- chlorine Bian bromine After being stirred overnight, water (50mL) quenching reaction is added dropwise to reaction solution, ethyl acetate extracts (50mL x in (115uL, 0.84mmol) 3) it, is washed through water (100mL), saturated salt solution (100mL) is washed after drying with anhydrous sodium sulfate, concentration, column chromatography (petroleum ether/second Acetoacetic ester (v/v)=4/1), obtain white solid (110mg, 54%).
1H NMR(400MHz,DMSO-d6): δ 8.37 (d, J=8.5Hz, 1H), 7.61 (s, 1H), 7.58-7.42 (m, 9H), 7.39 (d, J=5.4Hz, 2H), 7.28 (d, J=6.9Hz, 1H), 5.60 (s, 2H), 5.36 (s, 2H), 4.10 (s, 3H)
LC-MS:m/z 485.10[M+H]+.
The objective body compound of table 1 can be obtained using corresponding raw material by the similar synthetic method of embodiment 1.
Table 1
The objective body compound of table 2 can be obtained using corresponding raw material by the similar synthetic method of embodiment 4.
Table 2
The objective body compound of table 3 can be obtained using corresponding raw material by the similar synthetic method of embodiment 5.
Table 3
Biological Examples
This test case is used to measure the bactericidal activity of compound obtained in embodiment.Experiment target in this test case is designated as Botrytis cinerea pers and bacterium of downy mildew of cucumber.It is spare that 1%EC is dissolved into DMF.Using living body pot-culture method, these compounds are evaluated To 2 experiment target target bactericidal activities under 500mg/L dosage.Test method (is killed using initiative pesticide bioactivity evaluation SOP Microbial inoculum volume).
Bacterium of downy mildew of cucumber (Pseudoperonospora cubensis)
Select 1 consistent potting cucumber seedling of leaf period (plucking growing point) growing way, naturally dry after spraying treatment, processing It is inoculated with afterwards for 24 hours afterwards, takes fresh cucumber downy mildew disease leaf, dipped the lower sick leaf back sporangium of distillation washing with writing brush, be made into Sporangia suspension (2-3 × 105/ml).With inoculation sprayer (pressure 0.1MPa), even spraying is inoculated on cucumber seedling, is connect Test material after kind moves to phjytotron, keeps relative humidity 100%, and temperature is 21 DEG C or so, keeps 21 DEG C of left sides of temperature afterwards for 24 hours The right side, 95% or so moisturizing of relative humidity induce, and 5d backsight blank control incidence carries out classification investigation, refer to that calculating is anti-by disease Effect.
Botrytis cinerea pers (Botrytis cinerea)
Using blade bacterination process.The consistent potting cucumber seedling of two leaf period growing ways is selected to connect bacterium after reagent spray dries Cake is on blade.After 24-26 DEG C of half-light moisturizing for 24 hours, restore natural lighting moisturizing culture about 3d.With card after the onset of wait compare sufficiently Ruler measures each vaccination lesion diameter, calculates preventive effect.
Test result
Embodiment 13, embodiment 14, embodiment 16, embodiment 17, embodiment 21, embodiment 23, embodiment 27, embodiment 28 and embodiment 30 100% is reached to cucumber downy mildew.
Embodiment 11, embodiment 14, embodiment 18, embodiment 22, embodiment 23, embodiment 27 and embodiment 28 are to cucumber The preventive effect of gray mold reaches 100%.
It is very good that the compounds of this invention has plant pathogenic fungi, especially bacterium of downy mildew of cucumber and botrytis cinerea pers Control efficiency；Better than oximido-tetrazole compound of commercially available fungicide and structure proximate.

Claims (5)

1. a kind of compound is the salt of the compound as shown in formula (III) compound represented or formula (III):
Wherein:
X is hydrogen；
Y is-C (=O)-C1-6Alkyl ,-C (=O)-phenyl ,-C (=O)-morpholine or-C (=O)-O-C1-3Alkyl；Wherein Y is optional Ground is selected from R by 1 or 21Substituent group replaced；
Each R1It independently is fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, C1-4Alkyl, halogenated C1-4Alkyl, C1-4Alkane Oxygroup, halogenated C1-4Alkoxy, C1-4Alkylthio group or halogenated C1-4Alkylthio group.
2. compound according to claim 1, in which:
Y is-C (=O)-CH3,-C (=O)-CH2CH3,-C (=O)-CH2CH2CH3,-C (=O)-CH (CH3)2,-C (=O)- CH2CH(CH3)2,-C (=O)-C (CH3)3,-C (=O)-CH2CH2CH2CH2CH3,-C (=O)-CH2CH2CH(CH3)2,-C (= O)-CH2CH(CH3)CH2CH3,-C (=O)-CH (CH2CH3)2,-C (=O)-C (CH3)2CH2CH3,-C (=O)- CH2CH2CH2CH2CH2CH3,-C (=O)-O-CH3,-C (=O)-O-CH2CH3,-C (=O)-O-CH2CH2CH3Or-C (=O)-O- CH(CH3)2；
Or Y is following subformula:
Wherein Y is optionally selected from R by 1 or 21Substituent group replaced；
Each R1Independently be fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxyl, carboxyl, methyl, ethyl, n-propyl, isopropyl, Normal-butyl, tert-butyl, trifluoromethyl, methoxyl group, ethyoxyl, positive propoxy, isopropoxy ,-SCH3Or-SCF3。
3. a kind of compound is the compound with one of following structure or the salt with one of following structural compounds:
4. a kind of composition, living comprising surface acceptable in compound described in claim 1-3 any one and Pesticide Science Property agent and carrier.
5. compound described in claim 1-3 any one or composition as claimed in claim 4 are in control of plant disease Application.
CN201710362005.2A 2017-05-22 2017-05-22 Fungicide hydroximoyl-tetrazole derivatives Active CN108947964B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201710362005.2A CN108947964B (en) 2017-05-22 2017-05-22 Fungicide hydroximoyl-tetrazole derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201710362005.2A CN108947964B (en) 2017-05-22 2017-05-22 Fungicide hydroximoyl-tetrazole derivatives

Publications (2)

Publication Number Publication Date
CN108947964A CN108947964A (en) 2018-12-07
CN108947964B true CN108947964B (en) 2019-10-18

Family

ID=64462635

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201710362005.2A Active CN108947964B (en) 2017-05-22 2017-05-22 Fungicide hydroximoyl-tetrazole derivatives

Country Status (1)

Country Link
CN (1) CN108947964B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112979633B (en) * 2019-12-12 2024-02-02 东莞市东阳光农药研发有限公司 Novel oxime derivative, preparation method and application thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000351772A (en) * 1999-06-09 2000-12-19 Sagami Chem Res Center Production of new oxide derivative
CN1281452A (en) * 1997-12-10 2001-01-24 大日本油墨化学工业株式会社 Oxime derivatives and agricultural chemicals containing same
JP2010248273A (en) * 2010-08-10 2010-11-04 Nippon Soda Co Ltd Oxime compound or salt thereof, and fungicide
CN102007120A (en) * 2008-04-22 2011-04-06 拜尔农科股份公司 Fungicide hydroximoyl-heterocycles derivatives

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1281452A (en) * 1997-12-10 2001-01-24 大日本油墨化学工业株式会社 Oxime derivatives and agricultural chemicals containing same
JP2000351772A (en) * 1999-06-09 2000-12-19 Sagami Chem Res Center Production of new oxide derivative
CN102007120A (en) * 2008-04-22 2011-04-06 拜尔农科股份公司 Fungicide hydroximoyl-heterocycles derivatives
JP2010248273A (en) * 2010-08-10 2010-11-04 Nippon Soda Co Ltd Oxime compound or salt thereof, and fungicide
JP2011012088A (en) * 2010-08-10 2011-01-20 Nippon Soda Co Ltd Oxime compound or salt thereof, and fungicide

Also Published As

Publication number Publication date
CN108947964A (en) 2018-12-07

Similar Documents

Publication Publication Date Title
RU2480457C2 (en) Fungicial n-cycloalkylbenzyl thiocarboxamides or n-cycloalkylbenzyl-n&#39;-substituted amidine derivatives
JP5133985B2 (en) Tetrazoyl oxime derivatives and plant disease control agents
JP5542671B2 (en) Fungicide N-cycloalkyl-N-bicyclic-carboxamide derivatives
KR101280112B1 (en) Fungicide 2-pyridyl-methylene-carboxamide derivatives
RU2440982C2 (en) Fungicidal derivatives of n-6-member condensed (hetero)arylmethylene-n-cycloalkylcarboxamide
RU2427577C2 (en) Fungicide hydroximoyl-tetrazole derivatives
KR20100029843A (en) Tetrazoyloxime derivative and plant disease control agent
BR112018008659B1 (en) TRISSUBSTITUTED SILILFENOXY-HETEROCYCLES COMPOUNDS, FUNGICIDE COMPOSITION, METHOD FOR CONTROLLING UNWANTED PHYTOPATHOGENIC MICROORGANISMS AND PROCESS TO PREPARE SUCH COMPOUNDS
CN105829306B (en) The crystalline form of compound, includes its composition and application thereof at preparation method
JP2010529959A (en) Fungicide heterocyclyl-pyrimidinyl-amino derivatives
CN109983010A (en) 1- [2- (1- chlorine cyclopropyl) -2- hydroxyl -3- (3- phenyl -1,2- oxazole -5- base) propyl] -1H- imidazoles -5- 6-carbonitrile derivatives and related compound as the fungicide for crop protection
CN110894190B (en) Triazole compound and application thereof in agriculture
CN108349895A (en) Substituted 2- difluoromethyls-nicotine (thio) formailide derivative and its purposes as fungicide
CN101765598B (en) Fungicide N-5-membered fused heteroaryl-methylene-N-cycloalkyl-carboxamide derivatives
CN108947964B (en) Fungicide hydroximoyl-tetrazole derivatives
CN108690043B (en) Quinoline derivatives and its preparation method and application
CN109305964B (en) Fungicide hydroximoyl-tetrazole derivatives
CN109320452B (en) Quinoline derivatives and its preparation method and application
CN109574990A (en) Fungicide hydroximoyl-tetrazole derivatives
CN109311853A (en) Triazole derivative and its application in agricultural
CN109983000A (en) The imidazolyl methyl-derivatives that new 5- replaces
CN110452220A (en) 9 oxime derivate and its application in agricultural
JP5319674B2 (en) Fungicides 2-pyridyl-methylene-thiocarboxamide or 2-pyridyl-methylene-N-substituted carboximido derivatives
CN109890795A (en) The imdazole derivatives that new 5- replaces
CN109996796A (en) The imidazolyl methyl epoxyethane derivative that 5- as fungicide replaces

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
TR01 Transfer of patent right
TR01 Transfer of patent right

Effective date of registration: 20191024

Address after: Room 608, building 2, No. 368, Zhong Zhen'an Road, Chang'an Town, Dongguan City, Guangdong Province

Patentee after: Dongguan dongyangguang pesticide R & D Co., Ltd

Address before: Changan town in Guangdong province Dongguan City Zhen'an road 523871 No. 368

Patentee before: DONGGUAN DONGYANG GUANGKE R & D CO., LTD.