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CN116947749B - Amide compounds and application thereof - Google Patents

Amide compounds and application thereof Download PDF

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Publication number
CN116947749B
CN116947749B CN202311195463.3A CN202311195463A CN116947749B CN 116947749 B CN116947749 B CN 116947749B CN 202311195463 A CN202311195463 A CN 202311195463A CN 116947749 B CN116947749 B CN 116947749B
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optionally substituted
compound
compounds
alkyl
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CN116947749A (en
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李晶
张丽斌
焦体
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Purpana Beijing Technologies Co Ltd
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Purpana Beijing Technologies Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P5/00—Nematocides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Insects & Arthropods (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention discloses a compound of formula I and its salt and stereoisomer,

Description

Amide compounds and application thereof
Technical Field
The invention belongs to the field of pesticide chemistry, and particularly relates to an amide compound with a novel structure. The invention also relates to compositions comprising the compounds of the invention and to their use in agriculture for the prevention of plant diseases and insect pests.
Background
The amide compound is used for sterilization, inhibits mitochondrial respiration mainly by blocking electron transfer of succinic dehydrogenase in respiratory chain, and has the characteristics of broad sterilization spectrum and good sterilization effect. The invention discloses an amide compound with a novel structure, which has an excellent insecticidal effect.
Disclosure of Invention
The invention provides an amide compound with excellent insecticidal activity, which can be used for preventing and controlling plant diseases and insect pests of crops.
The invention provides a compound of formula I and its salts and stereoisomers thereof,i, wherein R is selected from H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted heteroaryl.
The present invention also provides a composition comprising a compound of formula I of the present invention and its salts and stereoisomers thereof, and at least one adjuvant selected from the group consisting of surfactants, solid diluents and liquid diluents.
The invention also provides application of the compound I and the salt and the stereoisomer thereof and the composition in preventing and controlling plant diseases and insect pests.
Advantageous effects
The compound has excellent insecticidal effect and wide application prospect in the aspect of controlling plant diseases and insect pests of crops.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention. Throughout the specification and claims, unless explicitly stated otherwise, the term "comprise" or variations thereof such as "comprises" or "comprising", etc. will be understood to include the stated elements or steps without excluding other material elements or steps.
In addition, numerous specific details are set forth in the following description in order to provide a better illustration of the invention.
It will be understood by those skilled in the art that the present invention may be practiced without some of these specific details. In some embodiments, materials, methods, means, etc. well known to those skilled in the art are not described in detail in order to highlight the gist of the present invention.
When the compounds of the invention can exist in tautomeric forms, the compounds mentioned above and below are to be understood as also including the corresponding tautomeric forms, where applicable, even if these tautomeric forms are not explicitly mentioned in each case.
If the compounds of the formula I according to the invention have functional groups which can be ionized, they can also be used in the form of their agriculturally acceptable salts or mixtures thereof.
The term "alkyl" (as well as in other groups containing alkyl groups, such as alkyl moieties of alkoxy, halo)The alkyl moiety of an alkyl group, the alkyl moiety of an arylalkyl group) in each case represents a linear or branched alkyl group having generally from 1 to 20 carbon atoms, frequently from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, in particular from 1 to 3 carbon atoms. Examples of C1-C4 alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), 1-dimethylethyl (tert-butyl). C (C) 1 -C 6 Examples of alkyl groups are, in addition to those mentioned for C1-C4 alkyl, also n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2-dimethylpropyl, 1-ethylpropyl, 1-dimethylpropyl, 1, 2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 2-trimethylpropyl, 1, 2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl.
"Ring" in the context of the present invention means "cycloalkyl" or "heterocyclyl" which means a monocyclic monovalent hydrocarbon radical of three to ten carbon atoms which may be saturated or contain one double bond. Cycloalkyl groups may be unsubstituted or substituted with one or two substituents independently selected from alkyl, halogen, alkoxy, hydroxy, or cyano, but are not limited thereto. Cycloalkyl radicals are preferably C 3 -C 8 Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. When cycloalkyl contains a double bond, it may be referred to herein as cycloalkenyl. "heterocyclyl" refers to a saturated or unsaturated monovalent monocyclic group of 4 to 8 ring atoms, wherein one or two ring atoms are heteroatoms selected from N, O or S (O) p, wherein p is an integer from 0 to 2 and the remaining ring atoms are C. More specifically, examples of the heterocyclic group include, but are not limited to, azetidinyl, oxetanyl, pyrrolidino, piperidino, homopiperidino, 2-oxopyrrolidino, 2-oxopiperidyl, morpholino, piperazinyl, tetrahydropyranyl, thiomorpholino, and the like. When cycloalkyl, heterocyclyl, etc., is substituted, it may be substituted with alkyl, halogen, cyanoSubstituted with a group, nitro group, aryl group, amido group, ester group, or the like, but is not limited thereto.
The term "optionally substituted" means that the relevant group may or may not be substituted with a substituent.
When the group is substituted, the substituent may be an alkyl group, a halogen, a cyano group, a nitro group, a cycloalkyl group, a heterocyclic group, an amido group, an ester group, an alkoxy group, a halogen, or the like, but is not limited thereto, for example, when the alkyl group is substituted with a halogen, a haloalkyl group is formed, but is not limited thereto.
Halogen in the present invention is typically fluorine, chlorine, bromine or iodine, preferably fluorine, bromine or chlorine. Accordingly, this also applies to halogens, such as haloalkyl, which are bonded to other structures. The haloalkyl group preferably has a chain length of 1 to 6 carbon atoms, more preferably a chain length of 1 to 4 carbon atoms. Examples of the alkyl groups of the haloalkyl group, such as fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2-trifluoroethyl, 2-fluoroethyl 2-chloroethyl, pentafluoroethyl, 1-difluoro-2, 2-trichloroethyl, 2, 3-tetrafluoroethyl and 2, 2-trichloroethyl; preferred are fluoromethyl, difluoromethyl, trifluoromethyl, trichloromethyl, difluoromethyl and dichlorofluoromethyl.
"aryl" in the present invention means a monovalent monocyclic or bicyclic aromatic hydrocarbon group of 6 to 10 ring atoms, such as phenyl or naphthyl, especially naphthyl, but is not limited thereto. The aryl group may be substituted with an alkyl group, a halogen group, a cyano group, a nitro group, a cycloalkyl group, a heterocyclic group, an amido group, an ester group, or the like, but is not limited thereto.
"heteroaryl" in the present invention encompasses: a 5 to 10 membered aromatic monocyclic ring, an aromatic fused ring, wherein the aromatic monocyclic ring contains one or more (e.g., 1 to 4, or in certain embodiments 1 to 3) heteroatoms selected from N, O and S and the remaining atoms are carbon; an aromatic fused ring comprising one or more (e.g., 1 to 4, or in certain embodiments 1 to 3) heteroatoms selected from N, O and S and the remaining ring atoms are carbon, and wherein at least one heteroatom is present in the aromatic ring. For example, heteroaryl includes a 5-to 10-membered heterocycloalkyl aromatic ring fused with a 5-to 10-membered cycloalkyl or heterocycloalkyl ring. For such fusions where only one ring contains one or more heteroatoms, the point of attachment may be on either ring. When the total number of S and O atoms in the heteroaryl group exceeds 1, these heteroatoms are not adjacent to each other. In certain embodiments, the total number of S and O atoms in the heteroaryl group is no more than 2. In certain embodiments, the total number of S and O atoms in the aromatic heterocycle is no more than 1. Examples of heteroaryl groups include, but are not limited to (numbered from the attachment position at position 1) 2-pyridyl, 3-pyridyl, 4-pyridyl, 2, 3-pyridazinyl, 3, 4-pyridazinyl, 2, 4-pyrimidinyl, 3, 5-pyrimidinyl, 2, 3-pyrazolinyl, 2, 4-imidazolinyl, isoxazolinyl, oxazolinyl, thiazolinyl, thiadiazolinyl, tetrazolyl, thienyl, benzothiophenyl, furyl, benzofuryl, benzimidazolinyl, indolinyl, pyrazinyl, triazolyl, quinolinyl, pyrazolyl and 5,6,7, 8-tetrahydroisoquinolinyl. Divalent radicals derived by removing a hydrogen atom from a carbon having a free valence in a monovalent heteroaryl radical whose name ends with a "radical" are named by adding a "subunit" to the name of the corresponding monovalent radical, e.g., the pyridyl radical having two points of attachment is a pyridine subunit. Heteroaryl does not encompass or overlap with aryl, cycloalkyl or heterocycloalkyl, as defined herein.
"arylalkyl" refers to a residue in which the aryl moiety is attached to the parent structure through an alkyl residue. Examples include benzyl, phenethyl, phenylvinyl, phenylallyl, and the like.
"heteroaralkyl" refers to a residue in which the heteroaryl moiety is attached to the parent structure through an alkyl residue. Examples include furanylmethyl, pyridylmethyl, pyrimidinylethyl, and the like.
Specifically, the invention firstly provides a compound of formula I and salts and stereoisomers thereof,i, wherein R is selected from H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted heteroaryl.
Advancing oneFurther, R is preferably optionally substituted C 1 -C 6 Alkyl, optionally substituted C 3 -C 6 Cycloalkyl, optionally substituted C 3 -C 8 Heterocyclyl, optionally substituted phenyl, and optionally substituted pyridinyl.
In some preferred embodiments, R is phenyl, halogen substituted phenyl, C 3 -C 8 A heterocyclic group.
Particularly preferably, the compounds of formula I according to the invention are selected from the following compounds:，，/>，/>，/>most preferably。
General synthetic procedure
In this specification, a structure is dominant if there is any difference between a chemical name and a chemical structure. In general, the compounds of the invention may be prepared by the methods described herein unless otherwise indicated. The following synthetic schemes and examples are provided to further illustrate the teachings of the present invention.
Those skilled in the art will recognize that: the chemical reactions described herein may be used to suitably prepare a wide variety of 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. For example, the synthesis of those non-exemplified compounds according to the invention can be successfully accomplished by modification methods by those skilled in the art, such as appropriate protection of interfering groups, by use of other known reagents (other than those described herein), or by making some conventional modifications to the reaction conditions. In addition, the reactions disclosed herein or known reaction conditions are also well-known to be applicable to the preparation of other compounds of the present invention.
Synthetic scheme
In the general synthesis process, the compound of the formula I reacts with an acylating reagent to generate acyl chloride, and an acylated product reacts with the compound of the formula III in a contact manner under alkaline conditions to synthesize the compound I. Preferably, the acylating agent is: the reaction solvent is dichloroethane, dichloromethane, toluene, chloroform, chlorobenzene, etc., the alkali is triethylamine, pyridine, potassium carbonate, sodium carbonate, etc., and the reaction temperature is 20-80 deg.
The present invention also provides a composition comprising a compound of formula I of the present invention and at least one adjuvant selected from the group consisting of surfactants, solid diluents and liquid diluents.
The compound or the composition of the invention is applied to the prevention and treatment of plant diseases and insect pests.
The compounds of the present invention are generally useful as pesticide active ingredients in compositions, i.e., formulations, and typically also include an agropharmaceutically acceptable surfactant and carrier. The carrier may be a solid carrier or a liquid carrier.
Suitable solid carriers include natural or synthetic clays and silicates, such as natural silica and diatomaceous earth; magnesium silicate, such as talc; magnesium aluminum silicate such as kaolinite, kaolin, montmorillonite and mica; white carbon black, calcium carbonate and light calcium carbonate; calcium sulfate; limestone; sodium sulfate; ammonium salts such as ammonium sulfate, hexamethylenediamine, urea, and the like.
The liquid carrier includes water and an organic solvent, which can also be used as an adjuvant or an anti-freezing additive when water is used as a solvent or diluent. Useful liquefied gaseous fillers or carriers are those liquids which are gaseous at standard temperature and standard pressure, for example aerosol propellants such as halogenated hydrocarbons, and butane, propane, nitrogen, carbon dioxide and the like.
Suitable organic solvents include aromatic hydrocarbons such as benzene, xylene, toluene, and the like; chlorinated hydrocarbons such as chlorobenzene, vinyl chloride, chloroform, methylene chloride, etc.; aliphatic hydrocarbons such as petroleum fractions, cyclohexane, light mineral oils; alcohols such as isopropanol, butanol, ethylene glycol, propylene glycol, cyclohexanol, and the like; and their ethers and esters; ketones such as acetone, cyclohexanone, dimethylformamide and N-methyl-pyrrolidone, vegetable oils such as soybean oil, rapeseed oil and cottonseed oil, and the like.
Suitable surfactants (adjuvants, emulsifiers, dispersants, protective colloids, wetting agents and binders) include all customary ionic and nonionic substances, for example ethoxylated nonylphenols, polyalkylene glycol ethers of straight-chain or branched alcohols, reaction products of alkylphenols with ethylene oxide and/or propylene oxide, reaction products of fatty acid amines with ethylene oxide and/or propylene oxide, and also fatty acid esters, alkyl sulfonates, alkyl sulfates, alkyl ether phosphates, aryl sulfates, ethoxylated arylalkyl phenols (e.g. tristyryl-phenol-ethoxylates), and ethoxylated and propoxylated arylalkyl phenols such as sulfated and phosphated arylalkyl phenol-ethoxylates and-ethoxy and-propoxylates. Other examples are natural and synthetic water-soluble polymers, such as lignosulfonates, gelatin, gum arabic, phospholipids, starches, hydrophobically modified starches and cellulose derivatives, in particular cellulose esters and cellulose ethers, and also polyvinyl alcohol, polyvinyl acetate, polyvinylpyrrolidone, polyacrylic acid, polymethacrylic acid and copolymers of (meth) acrylic acid and (meth) acrylic esters, and copolymers of methacrylic acid and methacrylic esters neutralized by alkali metal hydroxides, and optionally substituted naphthalenesulfonates condensed with formaldehyde. The presence of a surfactant is necessary if one of the active ingredients and/or one of the inert carriers is insoluble in water and the application takes place in water.
The pesticide sterilization/pesticide of the present invention can be prepared by a general method. For example, the active substances are mixed with liquid solvents and/or solid carriers, while surfactants such as emulsifiers, dispersants, stabilizers, wetting agents, and also other auxiliaries such as binders, defoamers, foaming agents, antioxidants, crystallization inhibitors, viscosity regulators, suspending agents, spray droplet regulators, pigments, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, permeation aids, micronutrients, dispersants, thickeners, freezing point depressants, biocides, etc. are added.
The pesticidal sterilization/insecticide of the present invention may be applied in the form of its formulation or in the form of use prepared therefrom, such as capsule suspension, fine granule, foam, paste, suspension concentrate, soluble concentrate, suspension, wettable powder, soluble powder, powder and granule, water-soluble and water-dispersible granule or tablet, and the like, but is not limited thereto.
The formulations of the present invention may also contain other components, for example other bactericides, insecticides, herbicides, plant growth regulators, attractants, acaricides, nematicides, fertilizers, safeners and the like, can be formulated with liquid fertilizers or solid, granular fertilizer carriers such as ammonium nitrate, urea and the like or mixed with fine sand or soil.
The present invention relates to the use of said compounds or compositions comprising said compounds as fungicides and insecticides in agriculture or in gardens for controlling or preventing the infestation of useful plants by pests.
Within the scope of the present invention, useful plants include the following plant species: grains (wheat, barley, rye, oats, rice, corn, sorghum and related species); beet (sugar beet); pome, stone fruit, and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, and blackberries); leguminous plants (lentils, bingo, peas, soybeans); oil crops (rape, mustard, olives, sunflowers, coconuts, castor oil plants, cocoa beans, groundnuts or soybeans); melon plants (pumpkin, cucumber, melon); fiber plants (cotton, flax, hemp, jute); citrus fruits (orange, lemon, grapefruit, mandarin); vegetables (spinach, lettuce, asparagus, cabbage, carrot, onion, tomato, potato, red pepper); laures (avocado, camphor) or plants, such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, grape vine, hops, bananas and natural rubber plants, as well as turf, ornamental and forest plants, such as flowers, shrubs, broad-leaved trees or evergreen trees, such as conifers, and plant propagation material.
The composition comprising the compound of the present invention is simple to use and the composition comprising the compound of the present invention is applied to the pest or its growing medium. The dosage of the composition of the present invention to be applied varies depending on weather conditions, dosage forms, application timing, application method, application area, target plant diseases and insect pests, target crops, etc. The compounds of the invention can be formulated in the application at a suitable concentration, for example 0.5ppm to 1000ppm, preferably 1ppm to 200ppm, depending on the control object, and have a certain activity against nematodes. Particularly preferred compounds 1 have a better insecticidal effect against pests at lower concentrations, for example, a control effect of approximately 60% against nematodes at a concentration of 1 ppm.
Preparation example
In this specification, a structure is dominant if there is any difference between a chemical name and a chemical structure. In general, the compounds of the invention may be prepared by the methods described herein unless otherwise indicated. The starting materials, reagents, and the like used in preparing the compounds of the invention are all commercially available or may be prepared by methods conventional in the art.
Example 1 Synthesis of N- (2- (3-chloro-5- (trifluoromethyl) pyridin-2-yl) ethyl) -4- (4-chlorophenoxy) -2- (trifluoromethyl) benzamide (Compound 1)
1.1 Synthesis of 4- (4-chlorophenoxy) -2- (trifluoromethyl) benzoic acid
Into a 250 mL reaction flask equipped with a reflux condenser and a thermometer, N2 was introduced, 100mL of DMF, 0.1mol of 3-chloro-2-trifluoromethylbenzoic acid, 0.11mol of p-chlorophenol, 0.12mol of potassium carbonate was added, and the temperature was raised to 100℃to react 8h. Stopping the reaction, filtering, concentrating, extracting with 200mL ethyl acetate, washing with 100mL saturated ammonium chloride solution, drying, desolventizing to obtain an orange concentrated solution of 4- (4-chlorophenoxy) -2- (trifluoromethyl) benzoic acid, and directly adding the orange concentrated solution into the next reaction without treatment.
1.2 Synthesis of N- (2- (3-chloro-5- (trifluoromethyl) pyridin-2-yl) ethyl) -4- (4-chlorophenoxy) -2- (trifluoromethyl) benzamide
Introducing N2 into a 1000 mL reaction bottle with a stirrer reflux condenser and a thermometer, adding 100mL dichloroethane, heating and refluxing to obtain 4- (4-chlorophenoxy) -2- (trifluoromethyl) benzoic acid, 1ml DMF, starting dropwise adding 0.12mol of sulfoxide chloride, dropwise adding 2h, detecting the reaction completion, adding 0.2mol of pyridine, adding 100ml dichloroethane, dropwise adding 0.2mol of 2- (3-chloro-5- (trifluoromethyl) pyridin-2-yl) ethane-1-amine at 0 degree, slowly heating to room temperature for reaction for 10h, detecting the reaction completion in a liquid phase, adding 200ml of ethyl acetate, adding 100ml of water, stirring for 20min, standing for layering, desolventizing an organic phase, crystallizing with ethyl acetate to obtain a white solid product, and obtaining the yield of 50%.
1 H NMR (500 MHz, DMSO) δ 8.91 (s, 1H,H-2), 8.59 (t,J= 5.6 Hz, 1H,H-1), 8.42 (d,J= 1.2 Hz, 1H, H-3), 7.55 – 7.48 (m, 3H,H-4, H-4’, H-4’’), 7.36 (d,J= 2.3 Hz, 1H, H-5), 7.30 (dd,J= 8.4, 2.3 Hz, 1H, H-6), 7.15 (m, 2H, H-7, H-7’), 3.69 (dd,J= 12.8, 6.6 Hz, 2H, H-8), 3.22 (t,J= 6.8 Hz, 2H, H-9).
The following compounds were synthesized by analogy with the methods described above
Table 1 synthetic example Compounds
Biological example: nematicide Activity assay
1. Test agent:
96% fluopyram crude drug (commercially available), compound 1, compound 2, compound 3 and compound 4 were prepared in the laboratory.
2. Preparing a nematode liquid:
(1) Picking root knot nematode eggs: peeling off root eggs on root system surface of plant (tomato and cucumber) with pointed tweezers, placing into a beaker containing pure water, sealing with filter paper, and culturing at 25deg.C for 48 hr.
(2) Preparing a nematode liquid: after the eggs are cultured for 48 hours, the egg masses are removed by filtering through a filter cloth, and the second-instar larvae with consistent instar are obtained.
(3) Investigation of the insect population base number: 1ml of the evenly mixed liquid containing the root-knot nematodes is taken to a counting plate, and counted under a dissecting mirror, so that the nematode suspension is ensured to be more than or equal to 100 nematodes per ml. The method has the advantages that the method has small nymph, can be used for centrifugal operation, is used for centrifugal operation for 2 minutes at 1000r/min, removes supernatant, is used for centrifugal operation, and finally uses pure water to dilute nematode liquid to be more than or equal to 100 per milliliter for standby.
3. Preparation of medicament
Dissolving each test agent with dimethyl sulfoxide organic solvent, diluting with 0.1% Tween-80 to obtain mother solution, and mixing with at least 10ml of each solution.
4. Medicament treatment
Adding 1ml of the prepared medicament into a centrifuge tube with 15ml, adding 3ml of prepared nematode suspension, uniformly mixing the liquid medicine with nematodes, adding a ventilation cover, keeping the temperature at 25 ℃ and culturing for 72 hours without light. And the treatment without the drug was used as a control.
5. Investigation of
Taking 1ml of mixed solution from each treatment to a counting plate 72h after the medicine, observing the death condition of nematodes under a stereoscopic vision, and recording the number of living nematodes, the number of dead nematodes and the behavior state of test worms of each treatment respectively, wherein the number of nematodes observed repeatedly is not less than 50.
6. Data calculation method
Mortality and corrected mortality for each treatment were calculated in percent (%) based on the survey data. According to the calculation of the companies (1) and (2), the calculation results all keep four bits after the decimal point.
Wherein:
P 1 representing mortality;
k represents the number of dead nematodes;
n represents the total nematode count investigated.
Wherein:
P 2 indicating a corrected mortality rate;
P t indicating mortality of the treated nematodes;
P 0 control nematode mortality was indicated.
TABLE 2 data on the activity of test compounds on root knot nematodes
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, a number of simple variants of the technical solution of the invention are possible, including combinations of the individual technical features in any other suitable way, which simple variants and combinations should likewise be regarded as being disclosed by the invention, all falling within the scope of protection of the invention.

Claims (3)

1. A compound and its salts and stereoisomers thereof, characterized by the compound structure:
。
2. a composition comprising a compound of claim 1 and its salts and stereoisomers thereof, and at least one adjuvant selected from the group consisting of surfactants, solid diluents and liquid diluents.
3. Use of the compounds of claim 1 and their salts and stereoisomers thereof, and the compositions of claim 2 for controlling plant diseases and insect pests.
CN202311195463.3A 2023-09-18 2023-09-18 Amide compounds and application thereof Active CN116947749B (en)

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CN114031551A (en) * 2021-12-27 2022-02-11 利民化学有限责任公司 Fluopyram and synthesis method thereof
CN115215793A (en) * 2022-08-11 2022-10-21 南开大学 Synthesis method of fluopyram

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CN1898207A (en) * 2003-12-19 2007-01-17 拜尔农科股份有限公司 2-pyridinylethylbenzamide derivatives
CN104023534A (en) * 2011-11-02 2014-09-03 拜耳知识产权有限责任公司 Compounds With Nematicidal Activity
CN114031551A (en) * 2021-12-27 2022-02-11 利民化学有限责任公司 Fluopyram and synthesis method thereof
CN115215793A (en) * 2022-08-11 2022-10-21 南开大学 Synthesis method of fluopyram

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