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WO2020133123A1 - Dérivés d'oxime-tétrazole et leur utilisation en médecine - Google Patents

Dérivés d'oxime-tétrazole et leur utilisation en médecine Download PDF

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Publication number
WO2020133123A1
WO2020133123A1 PCT/CN2018/124548 CN2018124548W WO2020133123A1 WO 2020133123 A1 WO2020133123 A1 WO 2020133123A1 CN 2018124548 W CN2018124548 W CN 2018124548W WO 2020133123 A1 WO2020133123 A1 WO 2020133123A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
present
alkoxy
och
compound
Prior art date
Application number
PCT/CN2018/124548
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English (en)
Chinese (zh)
Inventor
李义涛
林健
熊力
卢辉
田宇
李艳芳
朱德豆
黄昌
何利强
Original Assignee
东莞市东阳光农药研发有限公司
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
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Application filed by 东莞市东阳光农药研发有限公司 filed Critical 东莞市东阳光农药研发有限公司
Priority to CN201880085923.8A priority Critical patent/CN111630044A/zh
Priority to PCT/CN2018/124548 priority patent/WO2020133123A1/fr
Publication of WO2020133123A1 publication Critical patent/WO2020133123A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—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
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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

Definitions

  • the present invention relates to the field of pesticides, in particular to oxime-tetrazole derivatives and pesticides containing such derivatives as active ingredients, especially phytopathogenic fungus control agents.
  • the present invention provides a novel oxime derivative and a composition containing such a derivative.
  • the oxime derivative and its composition are used to control phytopathogenic fungi in agriculture.
  • the present invention provides a compound having a compound represented by formula (I) or a stereoisomer of a compound represented by formula (I), a nitrogen oxide, and a salt thereof:
  • Y is hydrogen or C 1-6 alkyl
  • n 1, 2, 3 or 4;
  • Each R a is independently hydrogen, halogen, nitro, cyano, hydroxy, C 1-6 alkyl, halogenated C 1-6 alkyl, C 1-6 alkoxy, halogenated C 1-6 alkoxy Group, C 2-6 alkenyl, C 2-6 alkynyl, C 2-6 alkenyloxy, C 2-6 alkynyloxy, C 3-8 cycloalkyl, phenyl or phenoxy;
  • R 1 , R 2 , R 3 , R 4 and R 5 are each independently hydrogen, halogen, nitro, cyano, hydroxy, amino, mercapto, C 1-6 alkyl, halogenated C 1-6 alkyl, C 1-6 alkoxy, halogenated C 1-6 alkoxy, C 1-6 alkylthio, halogenated C 1-6 alkylthio, C 1-6 alkoxy-C 1-6 alkyl Or halogenated C 1-6 alkoxy-C 1-6 alkyl.
  • Y is hydrogen or C 1-4 alkyl
  • n 1, 2, 3 or 4;
  • Each R a is independently hydrogen, halogen, nitro, cyano, hydroxy, C 1-4 alkyl, halogenated C 1-4 alkyl, C 1-4 alkoxy, halogenated C 1-4 alkoxy Group, C 2-4 alkenyl, C 2-4 alkynyl, C 2-4 alkenyloxy, C 2-4 alkynyloxy or C 3-6 cycloalkyl;
  • R 1 , R 2 , R 3 , R 4 and R 5 are each independently hydrogen, halogen, nitro, cyano, hydroxy, C 1-4 alkyl, C 1-4 alkoxy, halo C 1- 4 alkyl or halogenated C 1-4 alkoxy.
  • Y is hydrogen, -CH 3 or -CH 2 CH 3 ;
  • n 1, 2, 3 or 4;
  • Each R a is independently hydrogen, fluorine, chlorine, bromine, iodine, nitro, cyano, hydroxyl, -CH 3 , -CH 2 CH 3 , -CH 2 CH 2 CH 3 , -CH(CH 3 ) 2 , -CH 2 CH 2 CH 2 CH 3 , -CH(CH 3 )CH 2 CH 3 , -CH 2 CH(CH 3 )CH 3 , -C(CH 3 ) 3 , -CH 2 Cl, -CHF 2 ,- CF 3 , -CF(CF 3 ) 2 , -OCH 3 , -OCH 2 CH 3 , -OCH 2 CH 2 CH 3 , -OCH(CH 3 ) 2 or -OCF 3 ;
  • R 1 , R 2 , R 3 , R 4 and R 5 are each independently hydrogen, fluorine, chlorine, bromine, iodine, nitro, cyano, hydroxyl, -CH 3 , -CH 2 CH 3 , -CH 2 CH 2 CH 3 , -CH(CH 3 ) 2 , -CH 2 CH 2 CH 2 CH 3 , -CH(CH 3 )CH 2 CH 3 , -CH 2 CH(CH 3 )CH 3 , -C(CH 3 ) 3 , -OCH 3 , -OCH 2 CH 3 , -OCH 2 CH 2 CH 3 , -OCH(CH 3 ) 2 , -CH 2 Cl, -CHF 2 , -CF 3 , -CF(CF 3 ) 2 or- OCF 3 .
  • the present invention provides a compound that has a compound represented by formula (II) or a stereoisomer of a compound represented by formula (II), a nitrogen oxide, and a salt thereof:
  • R 1 , R 2 , R 3 , R 4 and R 5 have the meanings described in the present invention.
  • the present invention provides a compound that is a compound having one of the following structures or a stereoisomer of a compound having one of the following structures, a nitrogen oxide compound, and a salt thereof:
  • the invention provides a composition comprising at least one compound according to the invention.
  • compositions described herein further comprise agrochemically acceptable surfactants and/or carriers.
  • the present invention provides the use of the compound of the present invention or the composition of the present invention for controlling phytopathogenic fungi.
  • the invention provides methods of using the compounds of the invention or the compositions of the invention for controlling phytopathogenic fungi.
  • the articles “a”, “an” and “said” used in the present invention are intended to include “at least one” or “one or more”. Therefore, the articles used in the present invention refer to one or more than one (ie at least one) object articles.
  • a component refers to one or more components, that is, there may be more than one component that is considered to be employed or used in the implementation of the embodiment.
  • Stereoisomer refers to compounds that have the same chemical structure, but differ in the way the atoms or groups are arranged in space. Stereoisomers include enantiomers, diastereomers, conformational isomers (rotamers), geometric isomers (cis/trans) isomers, atropisomers, etc. .
  • Enantiomer refers to two isomers of a compound that cannot overlap but are mirror images of each other.
  • Diastereomer refers to a stereoisomer that has two or more chiral neutrals and whose molecules are not mirror images of each other. Diastereomers have different physical properties, such as melting point, boiling point, spectral properties and reactivity. Diastereomer mixtures can be separated by high-resolution analytical operations such as electrophoresis and chromatography, such as HPLC.
  • optically active compounds that is, they have the ability to rotate the plane of plane polarized light.
  • the prefixes D and L or R and S are used to denote the absolute configuration of the molecule with respect to one or more chiral centers.
  • the prefixes d and l or (+) and (-) are symbols used to specify the rotation of plane polarized light caused by a compound, where (-) or l indicates that the compound is levorotatory.
  • Compounds prefixed with (+) or d are right-handed.
  • a specific stereoisomer is an enantiomer, and a mixture of such isomers is called a mixture of enantiomers.
  • a 50:50 mixture of enantiomers is called a racemic mixture or a racemate, which can occur when there is no stereoselectivity or stereospecificity in a chemical reaction or process.
  • any asymmetric atoms (for example, carbon, etc.) of the compounds disclosed in the present invention can exist in racemic or enantiomerically enriched forms, such as (R)-, (S)-, or (R,S)-configuration forms exist.
  • each asymmetric atom has an enantiomeric excess of at least 50%, an enantiomeric excess of at least 60%, an enantiomeric excess of at least 70%, at least in the (R)- or (S)-configuration, at least 80% enantiomeric excess, at least 90% enantiomeric excess, at least 95% enantiomeric excess, or at least 99% enantiomeric excess.
  • the compounds of the present invention may be in one of the possible isomers or their mixtures, such as racemates and diastereomer mixtures (this depends on the number of asymmetric carbon atoms) Form exists.
  • Optically active (R)- or (S)-isomers can be prepared using chiral synthons or chiral reagents, or resolved using conventional techniques. If the compound contains a double bond, the substituent may be in the E or Z configuration; if the compound contains a disubstituted cycloalkyl, the cycloalkyl substituent may have a cis or trans configuration.
  • the resulting mixture of any stereoisomers can be separated into pure or substantially pure geometric isomers, enantiomers, diastereomers, for example, by chromatography Method and/or step crystallization method.
  • racemates of any resulting end products or intermediates can be resolved into optical enantiomers by methods known to those skilled in the art using known methods, for example, by obtaining the diastereomeric salts obtained Separate. Racemic products can also be separated by chiral chromatography, such as high-performance liquid chromatography (HPLC) using chiral adsorbents. In particular, enantiomers can be prepared by asymmetric synthesis.
  • HPLC high-performance liquid chromatography
  • the compounds of the present invention may be optionally substituted with one or more substituents, such as the compounds of the general formula above, or like the specific examples, subclasses, and inclusions of the present invention in the examples.
  • substituents such as the compounds of the general formula above, or like the specific examples, subclasses, and inclusions of the present invention in the examples.
  • a class of compounds such as the compounds of the general formula above, or like the specific examples, subclasses, and inclusions of the present invention in the examples.
  • substituents such as the compounds of the general formula above, or like the specific examples, subclasses, and inclusions of the present invention in the examples.
  • a class of compounds A class of compounds.
  • substituted is used interchangeably with the term “substituted or unsubstituted”.
  • substituted means that one or more hydrogen atoms in a given structure are replaced by specific substituents. Unless otherwise indicated, an optional substituent may be substituted at each substitutable position of the group.
  • substituents When more than one position in the given structural formula can be substituted by one or more substituents selected from specific groups, the substituents may be substituted at the same positions or differently. Specifically, examples of "one or more" refer to 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
  • the substituents described herein may be, but not limited to, deuterium, fluorine, chlorine, bromine, iodine, cyano, hydroxy, nitro, amino, carboxy, alkyl, alkoxy, alkoxyalkyl, alkyl Oxyalkoxy, alkoxyalkylamino, aryloxy, heteroaryloxy, heterocyclyloxy, arylalkoxy, heteroarylalkoxy, heterocyclylalkoxy, cycloalkane Alkoxy, alkylamino, alkylaminoalkyl, alkylaminoalkylamino, cycloalkylamino, cycloalkylalkylamino, alkylthio, haloalkyl, haloalkoxy, hydroxy-substituted alkyl, hydroxy-substituted alkyl Amino, cyano-substituted alkyl, cyano-substituted alkoxy, cyano-
  • C 1 -C 6 alkyl or "C 1-6 alkyl” particularly refers to independently disclosed methyl, ethyl, C 3 alkyl, C 4 alkyl, C 5 alkyl, and C 6 alkyl base.
  • alkyl or “alkyl group” means a saturated linear or branched monovalent hydrocarbon group containing 1 to 20 carbon atoms; wherein the alkyl group is optionally One or more substituents described in this invention are substituted. Unless otherwise specified, alkyl groups contain 1-20 carbon atoms. In one embodiment, the alkyl group contains 1-12 carbon atoms; in one embodiment, the alkyl group contains 1-8 carbon atoms; in another embodiment, the alkyl group contains 1- 6 carbon atoms; in yet another embodiment, the alkyl group contains 1-4 carbon atoms; in still another embodiment, the alkyl group contains 1-3 carbon atoms.
  • alkyl groups include, but are not limited to, methyl (Me, -CH 3 ), ethyl (Et, -CH 2 CH 3 ), n-propyl (n-Pr, -CH 2 CH 2 CH 3 ), isopropyl (i-Pr, -CH(CH 3 ) 2 ), n-butyl (n-Bu, -CH 2 CH 2 CH 2 CH 3 ), isobutyl (i-Bu, -CH 2 CH (CH 3 ) 2 ), sec-butyl (s-Bu, -CH(CH 3 )CH 2 CH 3 ), tert-butyl (t-Bu, -C(CH 3 ) 3 ), n-pentyl (-CH 2 CH 2 CH 2 CH 3 ), 2-pentyl (-CH(CH 3 )CH 2 CH 2 CH 3 ), 3-pentyl (-CH(CH 2 CH 3 ) 2 ), 2-methyl -2-butyl(-C(CH 3 ) 2
  • alkoxy means that the alkyl group is connected to the rest of the molecule through an oxygen atom, wherein the alkyl group has the meaning as described in the present invention.
  • alkoxy groups include, but are not limited to, methoxy (MeO, -OCH 3 ), ethoxy (EtO, -OCH 2 CH 3 ), 1-propoxy (n-PrO, n- Propoxy, -OCH 2 CH 2 CH 3 ), 2-propoxy (i-PrO, i-propoxy, -OCH(CH 3 ) 2 ), etc.
  • alkylthio means that the alkyl group is connected to the rest of the molecule through a sulfur atom, wherein the alkyl group has the meaning as described in the present invention.
  • alkylthio groups include, but are not limited to, -SCH 3 , -SCH 2 CH 3 , -SCH 2 CH 2 CH 3 , -SCH(CH 3 ) 2 and the like.
  • alkoxy-alkyl means that the alkyl group is substituted with one or more alkoxy groups, wherein the alkyl and alkoxy groups have the meaning as described in the present invention.
  • alkenyl refers to a straight-chain or branched monovalent hydrocarbon group containing 2-12 carbon atoms, in which there is at least one unsaturated site, that is, there is a carbon-carbon sp 2 double bond, wherein, the alkenyl group
  • the group may be optionally substituted with one or more substituents described in the present invention, which includes the positioning of "cis” and “tans", or the positioning of "E” and "Z”.
  • the alkenyl group contains 2-8 carbon atoms; in another embodiment, the alkenyl group contains 2-6 carbon atoms; in yet another embodiment, the alkenyl group contains 2 -4 carbon atoms.
  • alkynyl refers to a linear or branched monovalent hydrocarbon group containing 2-12 carbon atoms, in which there is at least one carbon-carbon sp triple bond, wherein the alkynyl group may be optionally substituted by one or more Substituted by the substituents described in this invention.
  • the alkynyl group contains 2-10 carbon atoms; in one embodiment, the alkynyl group contains 2-8 carbon atoms; in another embodiment, the alkynyl group contains 2- 6 carbon atoms; in yet another embodiment, the alkynyl group contains 2-4 carbon atoms.
  • alkynyl groups include, but are not limited to, -C ⁇ CH, -C ⁇ CCH 3 , -CH 2 -C ⁇ CH, -CH 2 -C ⁇ CCH 3 , -CH 2 CH 2 -C ⁇ CH , -CH 2 -C ⁇ CCH 2 CH 3 , -CH 2 CH 2 -C ⁇ CCH 3, etc.
  • cycloalkyl denotes a monovalent or polyvalent saturated monocyclic, bicyclic or tricyclic ring system containing 3-12 carbon atoms.
  • the cycloalkyl group contains 3-10 carbon atoms; in another embodiment, the cycloalkyl group contains 3-8 carbon atoms; in yet another embodiment, the cycloalkyl group contains 3-6 carbon atoms carbon atom.
  • the cycloalkyl group is optionally substituted with one or more substituents described in the present invention.
  • Such examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl Alkyl, etc.
  • halogen refers to fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
  • haloalkyl denotes an alkyl group is substituted with one or more halogen atoms, such examples include, but are not limited to, -CF 3, -CHF 2, -CH 2 Cl, -CH 2 CF 3, - CH 2 CHF 2 , -CH 2 CH 2 CF 3 and so on.
  • haloalkoxy means that the alkoxy group is substituted with one or more halogen atoms, such examples include, but are not limited to, -OCF 3 , -OCHF 2 , -OCHCl 2 , -OCH 2 CHF 2 , -OCH 2 CHCl 2 , -OCH(CH 3 )CHF 2 and so on.
  • haloalkylthio means that the alkylthio group is substituted with one or more halogen atoms, wherein the alkylthio group has the meaning as described in the present invention.
  • haloalkoxy-alkyl means that the "alkoxy-alkyl” group is substituted with one or more halogen atoms, wherein the "alkoxy-alkyl” group has the meaning as described in the present invention.
  • alkenyloxy means that an alkenyl group is connected to the rest of the molecule through an oxygen atom, wherein the alkenyl group has the meaning as described in the present invention.
  • alkynyloxy means that an alkynyl group is connected to the rest of the molecule through an oxygen atom, wherein the alkynyl group has the meaning as described in the present invention.
  • oxime portion of the oxime derivative described in the present invention there are stereostructures of the (Z) and (E) forms, and both stereoisomers and mixtures thereof are included in the present invention.
  • the two stereoisomers can be separated according to methods well known to those skilled in the art.
  • Salts of the compounds described in the present invention include those derived from alkali metals or alkaline earth metals and those derived from ammonia and amines.
  • Preferred cations include sodium, potassium, magnesium and ammonium cations having the chemical formula N + (R A R B R C R D ), where R A , R B , R C and R D are independently selected from hydrogen, C 1 -C 6 alkyl and C 1 -C 6 hydroxyalkyl.
  • Salts of compounds of formula (I) or (II) can be obtained by using metal hydroxides (eg sodium hydroxide) or amines (eg ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, diallyl) Amine, 2-butoxyethylamine, morpholine, cyclododecylamine or benzylamine) are prepared by treating compounds of formula (I) or formula (II).
  • metal hydroxides eg sodium hydroxide
  • amines eg ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, diallyl
  • acceptable salts can be formed from organic and inorganic acids, such as acetic acid, propionic acid, lactic acid, citric acid, tartaric acid, succinic acid, fumaric acid, maleic acid, propanediol Acid, mandelic acid, malic acid, phthalic acid, hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, methanesulfonic acid, naphthalenesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, camphorsulfonic acid and the like are known Accepted acid.
  • organic and inorganic acids such as acetic acid, propionic acid, lactic acid, citric acid, tartaric acid, succinic acid, fumaric acid, maleic acid, propanediol Acid, mandelic acid, malic acid, phthalic acid, hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, me
  • compositions and formulations of compounds of the present invention are provided.
  • the compounds of the present invention are generally useful as fungicidal active ingredients in compositions, ie, formulations, and generally also include pesticide-acceptable surfactants and/or carriers.
  • the above surfactants may be various surfactants known in the field of pesticide formulations, such as anionic surfactants, cationic surfactants, nonionic surfactants and amphoteric surfactants, block polymers, polyelectrolytes, and their mixture.
  • Such surfactants can be used as emulsifiers, dispersants, wetting agents, penetration enhancers or adjuvants.
  • Suitable anionic surfactants are alkali metal, alkaline earth metal or ammonium salts of sulfonic acid, sulfuric acid, phosphoric acid, carboxylic acid, and mixtures thereof.
  • sulfonates are alkyl aryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, ethoxylated alkylphenols Sulfonates, alkoxylated arylphenol sulfonates, condensed naphthalene sulfonates, dodecyl- and tridecylbenzene sulfonates, naphthalene and alkyl naphthalene sulfonates, sulfonates Succinate or sulfosuccinate.
  • sulfates are sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols or sulfates of fatty acid esters.
  • An example of phosphate is phosphate ester.
  • carboxylates are alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymer surfactants and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters that have been alkoxylated with 1-50 equivalents.
  • Ethylene oxide and/or propylene oxide can be used for alkoxylation, preferably ethylene oxide.
  • N-substituted fatty acid amides are fatty acid glucamide or fatty acid alkanolamide.
  • esters are fatty acid esters, glycerides or monoglycerides.
  • sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides.
  • polymer surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol or vinyl acetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with 1 or 2 hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkyl betaines and imidazolines.
  • Suitable block polymers are A-B or A-B-A type block polymers containing blocks of polyoxyethylene and polyoxypropylene, or A-B-C type block polymers containing alkanol, polyoxyethylene and polyoxypropylene.
  • a suitable polyelectrolyte is polyacid or polybase. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamine or polyvinylamine.
  • the above carrier may be various carriers known in the field of pesticide formulations, including various silicates, carbonates, sulfates, oxides, phosphates, plant carriers, and synthetic carriers. Specifically, for example: white carbon black, kaolin, diatomaceous earth, clay, talc, organic bentonite, pumice, titanium dioxide, dextrin, cellulose powder, light calcium carbonate, soluble starch, corn starch, sawdust powder, urea, amine Fertilizer, mixture of urea and amine fertilizer, glucose, maltose, sucrose, anhydrous potassium carbonate, anhydrous sodium carbonate, anhydrous potassium bicarbonate, anhydrous sodium bicarbonate, attapulgite, anhydrous potassium carbonate and anhydrous bicarbonate One or more of a mixture of potassium and a mixture of anhydrous sodium carbonate and anhydrous sodium bicarbonate.
  • the fungicide composition may further contain various auxiliary agents commonly used in the field of pesticide formulations, specifically, the auxiliary agents for the preparation may be solvents, co-solvents, thickeners , Antifreeze, capsules, protective agents, defoamers, disintegrants, stabilizers, preservatives, adhesives, chelating agents one or more.
  • the auxiliary agents for the preparation may be solvents, co-solvents, thickeners , Antifreeze, capsules, protective agents, defoamers, disintegrants, stabilizers, preservatives, adhesives, chelating agents one or more.
  • Suitable solvents are water and organic solvents, such as medium to high boiling mineral oil fractions, such as kerosene, diesel; oils of vegetable or animal origin; aliphatic, cyclic, and aromatic hydrocarbons, such as toluene, paraffin, tetralin , Alkylated naphthalene; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, such as cyclohexanone; esters, such as lactate, carbonate, Fatty acid esters, ⁇ -butyrolactone; fatty acids; phosphonates; amines; amides, such as N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.
  • medium to high boiling mineral oil fractions such as kerosene, diesel
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic, and aromatic hydrocarbons such as
  • the above solvent can also be used as a co-solvent.
  • Suitable thickeners are selected from polysaccharides (eg xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.
  • Suitable antifreeze agents are selected from ethylene glycol, propylene glycol, glycerin, urea, glycerin and mixtures thereof.
  • Suitable bladders are selected from polyurethane, polyurea, urea-formaldehyde resin and mixtures thereof.
  • Suitable protective agents are selected from polyvinyl alcohol and/or polyethylene glycol.
  • Suitable defoamers are selected from polysiloxanes, silicone milks, long-chain alcohols, fatty acids and their salts, and fluorine-containing organics and mixtures thereof.
  • Suitable disintegrants are selected from bentonite, urea, ammonium sulfate, aluminum chloride, citric acid, succinic acid, sodium bicarbonate and mixtures thereof
  • Suitable stabilizers are selected from triphenyl phosphite, epichlorohydrin, acetic anhydride and mixtures thereof.
  • Suitable preservatives are selected from benzoic acid, sodium benzoate, 1,2-benzisothiazolin-3-one (abbreviated as BIT), carson, potassium sorbate, and mixtures thereof.
  • Suitable binders are selected from polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylate, biowax or synthetic wax, and cellulose ether.
  • the fungicides of the present invention can be applied in the form of their formulations or the use forms prepared therefrom, such as aerosols, capsule suspensions, cold-fogging concentrates, hot-mist concentrates, capsules Granules, fine granules, flowable concentrates for seed treatment, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, Large granules, micro granules, oil-dispersible powders, oil-miscible flow concentrates, oil-miscible liquids, aerosols (under pressure), gas-generating products, foams, pastes, suspension concentrates, suspension milk Concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, powders and granules, water-soluble and water-dispersible granules or tablets, water-soluble or water-dispersible powders for seed treatment, can be Wet powders
  • the compounds of the present invention can be used as plant disease control agents. Therefore, the present invention may also include a method for controlling plant diseases caused by phytopathogenic fungi, which method comprises applying an effective amount of a compound of the present invention to the plant to be protected or a part thereof or to the plant seed to be protected or comprising Fungicidal composition of the compound.
  • the compounds and/or compositions of the present invention can provide control of diseases caused by broad-spectrum plant pathogenic fungi of the Basidiomycetes, Ascomycetes, Oomycetes, and Semimycetes. They can effectively control broad-spectrum plant diseases, especially leaf pathogens of ornamental crops, lawn crops, vegetable crops, field crops, cereal crops and fruit tree crops.
  • pathogens include: Oomycetes, including Phytophthora diseases such as Phytophthora infestans, Phytophthora megasperma, Phytophthora parasitica, Phytophthora diseases of cinnamomi and Phytophthora capsici, diseases of Pythium species such as Pythium aphanidermatum, and diseases of Peronosporaceae species such as grape downy mildew Plasmopara viticola, Peronospora diseases (including Peronospora tabacina and Peronospora parasitica), Pseudoperonospora diseases (including cucumber downy mildew) (Pseudoperonospora cubensis) and Bremia lactucae); Ascomycetes (including Alternaria) such as Alternaria solani and Alternaria brassicae, Cocci (Guignardia) diseases such as grape black rot fungus (Guignardia bidwell), genus Vent
  • Basidiomycetes including rust fungus caused by Puccinia spp. (such as Puccinia reconcondita, Puccinia striiformis), Leaf rust fungus (Puccinia hordei), Puccinia graminis and Puccinia arachidis, coffee rust fungus (Hemileia vastatrix) and soybean rust fungus (Phakopsora pachyrhizi); other pathogens include Rhizoctonia species ( Rhizoctonia spp.
  • Rhizoctonia solani Fusarium species diseases such as Fusarium pink (Fusarium roseum), Fusarium graminearum (Fusarium graminearum) and Fusarium oxysporum (Fusarium oxysporum) ); Verticillium dahliae; Sclerotium rolfsii; Rynchosporium secalis; Cercosporidium personsatum, Cercospora arachidicola and Cercospora beticola ); and other categories and strains closely related to these pathogens.
  • composition or combination is effective against bacteria such as Erwinia amylovora, Xanthomonas campestris, Pseudomonas syringae, and others
  • bacteria such as Erwinia amylovora, Xanthomonas campestris, Pseudomonas syringae, and others
  • the strain is resistant.
  • the method of using the fungicide composition of the present invention is simple. Before or after germination of plant diseases, it is applied to crops and crop growth sites according to conventional methods, such as soil mixing, spraying, spraying, pouring, etc., and the application amount depends on the climate. Depends on the conditions or crop conditions, generally apply 10-5000g per mu, diluted to 10-400mg/L application.
  • the diluent is preferably water.
  • the fungicidal composition of the present invention is usually related to external factors such as climate, but by using an appropriate dosage form can reduce the impact of climate.
  • composition of the present invention can also be used in combination with other compounds having bactericidal, insecticidal or herbicidal properties, and can also be mixed with nematicides, acaricides, protective agents, herbicide safeners, growth regulators, phytonutrients or soil regulators Etc. mixed use.
  • the compound of the present invention can be prepared by the method described in the present invention, unless otherwise specified, wherein the definition of the substituent is as shown in (I).
  • the chemical reactions described in the present invention can be used to properly prepare many other compounds of the present invention, and other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention Inside.
  • the synthesis of non-exemplified compounds according to the present invention can be successfully accomplished by those skilled in the art through modification methods, such as appropriate protection of interfering groups, by using other known reagents (in addition to those described in the present invention), Or the reaction conditions can be modified routinely.
  • the reactions disclosed in the present invention or known reaction conditions are also generally applicable to the preparation of other compounds of the present invention.
  • the reaction of the present invention is performed at room temperature, where the room temperature is -10 to 40°C.
  • the target compound 1-1 can be prepared by Synthesis Scheme 1. Intermediate a and intermediate b are reacted in a basic system to obtain the target compound I-1.
  • Step 2 Synthesis of (6-(hydroxymethyl)pyridin-2-yl)carbamic acid tert-butyl ester
  • Step 3 Synthesis of (6-(bromomethyl)pyridin-2-yl)carbamic acid tert-butyl ester
  • Step 3 Synthesis of (1-methyl-1H-tetrazol-5-yl) (4-phenoxyphenyl) ketone
  • This test example was used to determine the fungicidal activity of the compounds prepared in the examples.
  • the test target in this test example is cucumber downy mildew. Use N,N-dimethylformamide to dissolve into 1% emulsifiable concentrate.
  • the in vivo pot method was used to evaluate the fungicidal activity of these compounds against the test target at a dose of 200 mg/L.
  • the test method adopts the SOP (Fungicide Volume) for biological activity evaluation of the created pesticide.
  • the temperature is maintained at approximately 21°C and a relative humidity of 95 Moisture induced by about 3%, and a graded investigation of the incidence of the blank control in the backsight after 5 days, and the prevention effect was calculated according to the disease index.
  • Example 1 Control effect on cucumber downy mildew (%) Example 1 100 Example 2 100 Example 3 100
  • Example 4 100 Example 5 100 Example 6 90 Example 8 95 Example 10 100 Example 11 100 Example 12 100 Example 13 98 Example 14 95
  • the compound of the present invention has a good control effect on phytopathogenic fungi, especially on cucumber downy mildew, and has the value of further research and development.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
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  • Wood Science & Technology (AREA)
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  • Agronomy & Crop Science (AREA)
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Abstract

L'invention concerne un dérivé d'oxime-tétrazole. Plus particulièrement, l'invention concerne un dérivé d'oxime-tétrazole représenté par la formule (I), ou un sel, un N-oxyde, des isomères (E) et (Z) ou un mélange de ceux-ci, le dérivé d'oxime-tétrazole représenté par la formule (I), un procédé de préparation du dérivé d'oxime-tétrazole, et une utilisation de celui-ci en tant que fongicide, une forme d'une composition fongicide de celui-ci, et un procédé de prévention et de traitement de champignons phytopathogènes de plantes utilisant un tel composé ou une telle composition.
PCT/CN2018/124548 2018-12-28 2018-12-28 Dérivés d'oxime-tétrazole et leur utilisation en médecine WO2020133123A1 (fr)

Priority Applications (2)

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CN201880085923.8A CN111630044A (zh) 2018-12-28 2018-12-28 肟基-四唑衍生物及其在农业中的应用
PCT/CN2018/124548 WO2020133123A1 (fr) 2018-12-28 2018-12-28 Dérivés d'oxime-tétrazole et leur utilisation en médecine

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CN114195763B (zh) * 2020-09-17 2025-01-10 东莞市东阳光农药研发有限公司 一种苯甲酰氧基取代的肟类衍生物及其应用

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JP2004131392A (ja) * 2002-10-08 2004-04-30 Sumitomo Chem Co Ltd テトラゾール化合物およびその用途
JP2004131416A (ja) * 2002-10-10 2004-04-30 Sumitomo Chem Co Ltd テトラゾール化合物およびその植物病害防除用途
CN1553907A (zh) * 2001-08-20 2004-12-08 ���ձ���ī��ѧ��ҵ��ʽ���� 四唑基肟衍生物以及把其作为有效成分的农药
CN101977502A (zh) * 2008-03-19 2011-02-16 拜尔农科股份公司 杀真菌剂肟基-四唑衍生物
CN102083816A (zh) * 2008-07-04 2011-06-01 拜尔农科股份公司 杀真菌剂肟基-四唑衍生物

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CN1553907A (zh) * 2001-08-20 2004-12-08 ���ձ���ī��ѧ��ҵ��ʽ���� 四唑基肟衍生物以及把其作为有效成分的农药
JP2004131392A (ja) * 2002-10-08 2004-04-30 Sumitomo Chem Co Ltd テトラゾール化合物およびその用途
JP2004131416A (ja) * 2002-10-10 2004-04-30 Sumitomo Chem Co Ltd テトラゾール化合物およびその植物病害防除用途
CN101977502A (zh) * 2008-03-19 2011-02-16 拜尔农科股份公司 杀真菌剂肟基-四唑衍生物
CN102083816A (zh) * 2008-07-04 2011-06-01 拜尔农科股份公司 杀真菌剂肟基-四唑衍生物

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