Pyridinamine compounds, processes for their preparation and uses thereof

Abstract

The present application provides a pyridine amine compound, a preparation method and application thereof, in particular, the present application relates to a compound shown in formula (I), a preparation method of the compound shown in formula (I), and the use of a composition and / or preparation containing the compound shown in formula (I) as an insecticide in agriculture, forestry and / or horticulture;Wherein, in formula (I), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 And A have the meanings described in the present application.

Description

Technical Field

[0001] This invention relates to the field of pesticides, and more specifically, to a pyridineamine compound, its preparation method, and the application of such derivatives and compositions containing such derivatives as pest control agents in agriculture, forestry, or horticulture. Background Technology

[0002] Through years of research and development of insecticides, many types of insecticides have been developed, such as organophosphates, carbamates, and neonicotinoids, and have been put into use. These pesticides play an extremely important role in improving agricultural production. However, in recent years, problems such as residues and cumulative environmental pollution have limited their use, and long-term use has led to varying degrees of insect resistance. Therefore, there is a need to continuously develop compounds that possess excellent insecticidal properties against various pests, have novel structures, are more effective, more economical, less toxic, safer for the environment, have different sites of action, and can be safely used. Summary of the Invention

[0003] This invention relates to a pyridine amine compound with a novel structure that exhibits excellent control efficacy against pests in agriculture, forestry, or horticulture, particularly alfalfa aphids, peach aphids, and whiteflies.

[0004] Specifically:

[0005] On one hand, the present invention relates to a compound, which is a compound of formula (I) or a stereoisomer of the compound of formula (I), a nitrogen oxide or a salt thereof:

[0006] I);

[0007] in:

[0008] R 1 R 2 R 3 and R 4 Each of these groups can be independently identified as hydrogen, halogen, hydroxyl, nitro, amino, carboxyl, cyano, or C. 1-6 Alkyl, C 1-6 Alkoxy, halogenated C 1-6 Alkyl, Halogenated C 1-6 Alkoxy, C 1-6 Alkyl thiols, halogenated C 1-6 Alkylthio, C 3-8 cycloalkyl, C 3-8 Cycloalkyloxy, C 3-8 cycloalkyl-C 1-3 Alkylene-, -N(C) 1-6 Alkyl)2、-C(=O)N(C 1-6 Alkyl)2, C 1-6Alkyl-C(=O)-, Halogenated C 1-6 Alkyl-C(=O)-, C 1-6 alkoxy-C (=O)- or halogenated C 1-6 Alkyloxy-C(=O)-;

[0009] R 5 and R 6 Each is independently hydrogen, halogen, C 1-6 Alkyl, C 1-6 Alkoxy, halogenated C 1-6 Alkyl or halogenated C 1-6 Alkoxy;

[0010] A is or ,in,

[0011] R a1 R a2 R a3 R a4 R b1 R b2 R c1 and R c2 Each group independently represents hydrogen, halogen, cyano, hydroxyl, nitro, carboxyl, amino, and C. 1-6 Alkyl, C 1-6 Alkoxy, halogenated C 1-6 Alkyl, Halogenated C 1-6 Alkoxy, C 1-6 alkylthio or halogenated C 1-6 Alkylthio;

[0012] R b3 and R c3 Each independently is hydrogen, C 1-6 Alkyl or halogenated C 1-6 alkyl.

[0013] In some implementation schemes, R 1 R 2 R 3 and R 4 Each of these groups can be independently identified as hydrogen, halogen, hydroxyl, nitro, amino, carboxyl, cyano, or C. 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 Alkyl, Halogenated C 1-4 Alkoxy, C 1-4 Alkyl thiols, halogenated C 1-4 Alkylthio, C 3-6 cycloalkyl, C 3-6 Cycloalkyloxy, C 3-6 cycloalkyl-C 1-3 Alkylene-, -N(C) 1-4Alkyl)2、-C(=O)N(C 1-4 Alkyl)2, C 1-4 Alkyl-C(=O)-, Halogenated C 1-4 Alkyl-C(=O)-, C 1-4 alkoxy-C (=O)- or halogenated C 1-4 Alkoxy-C(=O)-.

[0014] In some implementation schemes, R 5 and R 6 Each is independently hydrogen, halogen, C 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 Alkyl or halogenated C 1-4 Alkyl group.

[0015] In some implementation schemes, R 1 R 2 R 3 and R 4 Each can be independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, hydroxyl, nitro, carboxyl, amino, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CF3, -CHF2, -CH2CF3, -OCH3, -OCH2CH3, -OCF3, -OCH2CF3, -SCH3, -SCH2CH3, -SCF3 or -SCH2CHF2.

[0016] In some implementation schemes, R 5 and R 6 Each can be independently hydrogen, fluorine, chlorine, bromine, iodine, -CH3, -CH2CH3, -OCH3, -OCH2CH3, -CF3, or -OCF3.

[0017] Preferably, R 5 and R 6 Each is hydrogen independently.

[0018] In some implementation schemes, A is or ;

[0019] Among them, R a1 R a2 R a3 R a4 R b1 R b2 R c1 and R c2 Each group independently represents hydrogen, halogen, cyano, hydroxyl, nitro, carboxyl, amino, and C. 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 Alkyl, Halogenated C1-4 Alkoxy, C 1-4 alkylthio or halogenated C 1-4 Alkylthio;

[0020] R b3 and R c3 Each independently is hydrogen, C 1-4 Alkyl or halogenated C 1-4 alkyl.

[0021] In some implementation schemes, A is or

[0022] Among them, R a1 R a2 R a3 R a4 R b1 R b2 R c1 and R c2 Each can be independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, hydroxyl, nitro, carboxyl, amino, -CH3, -CH2CH3, -CH(CH3)2, -OCH3, -OCH2CH3, -SCH3, -SCH2CH3, -CF3, -CHF2, -CH2CF3, -OCF3, -OCHF2, -OCH2CF3, -SCF3 or -SCH2CHF2;

[0023] R b3 and R c3 Each can be independently hydrogen, -CH3, -CH2CH3, -CH(CH3)2, -CF3, -CH2CHF2 or -CH2CF3.

[0024] In some implementation schemes, A is ;

[0025] Among them, R a1 R a2 R a3 and R a4 Each group independently represents hydrogen, halogen, cyano, hydroxyl, nitro, carboxyl, amino, and C. 1-4 Alkyl, C 1-4 Alkoxy, halogenated C 1-4 Alkyl, Halogenated C 1-4 Alkoxy, C 1-4 alkylthio or halogenated C 1-4 Alkylthio group.

[0026] In some implementation schemes, A is ;

[0027] Among them, R a1 R a2 Ra3 and R a4 Each can be independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, hydroxyl, nitro, carboxyl, amino, -CH3, -CH2CH3, -CH(CH3)2, -OCH3, -OCH2CH3, -SCH3, -SCH2CH3, -CF3, -CHF2, -CH2CF3, -OCF3, -OCHF2, -OCH2CF3, -SCF3, or -SCH2CHF2.

[0028] In some embodiments, the present invention relates to a compound, which is a compound of formula (Ia) or a stereoisomer of the compound of formula (Ia), a nitride, or a salt thereof:

[0029] (Ia);

[0030] Among them, R 1 R 2 R 3 R 4 R a1 R a2 R a3 and R a4 It has the meaning described in this invention.

[0031] In some implementation schemes, for or

[0032] In some implementation schemes, for or

[0033] In some embodiments, the present invention relates to a compound having one of the following structures, or a stereoisomer, nitride, or salt thereof having one of the following structures:

[0034]

[0035]

[0036] On the other hand, the present invention relates to a composition comprising at least one compound described herein and at least one pesticide-acceptable adjuvant.

[0037] On the other hand, the present invention relates to the application of the compounds or compositions described herein as pest control agents in agriculture, forestry or horticulture.

[0038] In some embodiments, the present invention relates to the use of the compounds or compositions described herein in the prevention and / or control of alfalfa aphids, peach aphids and / or whiteflies.

[0039] Furthermore, in some embodiments, the present invention relates to the use of the compounds or compositions described herein in the prevention and / or control of pests, said pests including at least one of alfalfa aphids, peach aphids, and whiteflies.

[0040] Furthermore, in some embodiments, the present invention relates to the use of the compounds or compositions described herein in the prevention and / or control of alfalfa aphids.

[0041] Furthermore, in some embodiments, the present invention relates to the use of the compounds or compositions described herein in the prevention and / or control of peach aphids.

[0042] Furthermore, in some embodiments, the present invention relates to the use of the compounds or compositions described herein in the prevention and / or control of whiteflies.

[0043] On the other hand, the present invention relates to a method for controlling pests, the method comprising applying an effective amount of the compound or composition described herein to the pest or the location of the pest.

[0044] Detailed Description of the Invention

[0045] Definitions and general terms

[0046] Certain embodiments of the invention will now be described in detail, examples of which are illustrated by the accompanying structural and chemical formulas. The invention is intended to cover all alternatives, modifications, and equivalents, all of which are included within the scope of the invention as defined in the claims. Those skilled in the art will recognize that many similar or equivalent methods and materials can be used to practice the invention. The invention is by no means limited to the methods and materials described herein. In the event that one or more of the incorporated documents, patents, and similar materials differ from or contradict this application (including, but not limited to, defined terminology, application of terminology, described techniques, etc.), this application shall prevail.

[0047] It should be further appreciated that certain features of the invention, for clarity, have been described in multiple independent embodiments, but may also be provided in combination in a single embodiment. Conversely, various features of the invention, for brevity, have been described in a single embodiment, but may also be provided individually or in any suitable sub-combination.

[0048] Unless otherwise stated, all technical terms used in this invention have the same meaning as commonly understood by one of ordinary skill in the art. All patents and publications related to this invention are incorporated herein by reference in their entirety.

[0049] Unless otherwise stated, the following definitions as used in this invention shall apply. For the purposes of this invention, chemical elements are consistent with the periodic table (CAS edition) and the Handbook of Chemistry and Physics, 75th edition, 1994. Furthermore, general principles of organic chemistry can be found in "Organic Chemistry," Thomas Sorrell, University Science Books, Sausalito: 1999, and "March's Advanced Organic Chemistry" by Michael B. Smith and Jerry March, John Wiley & Sons, New York: 2007, the entire contents of which are incorporated herein by reference.

[0050] Unless otherwise stated or there is an obvious conflict in the context, the articles “a,” “an,” and “described” as used in this invention are intended to include “at least one” or “one or more.” Therefore, these articles as used in this invention refer to articles for one or more (i.e., at least one) objects. For example, “a component” refers to one or more components, meaning that more than one component may be considered for use or employed in the embodiments described.

[0051] The term "comprising" is an open-ended expression, meaning it includes the contents specified in this invention, but does not exclude other aspects.

[0052] "Stereoisomers" are compounds that have the same chemical structure but whose atoms or groups are arranged differently in space. Stereoisomers include enantiomers, diastereomers, conformational isomers (rotational isomers), geometric isomers (cis / trans) isomers, and hindered isomers, etc.

[0053] "Enantiomers" refer to two non-overlapping but mirror-image isomers of a compound.

[0054] A diastereomer is a stereoisomer that has two or more chiral neutral molecules that are not mirror images of each other. Diastereomers possess different physical properties, such as melting point, boiling point, spectral properties, and reactivity. Mixtures of diastereomers can be separated using high-resolution analytical techniques such as electrophoresis and chromatography, for example, HPLC.

[0055] The stereochemical definitions and rules used in this invention generally follow the descriptions in 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.

[0056] Many organic compounds exist in an optically active form, meaning they possess the ability to rotate the plane of plane-polarized light. In describing optically active compounds, the prefixes D and L or R and S are used to indicate the absolute configuration of the molecule with respect to one or more of its chiral centers. The prefixes d and l or (+) and (-) are symbols used to specify the plane-polarized light rotation caused by the compound, where (-) or l indicates that the compound is levorotatory. Compounds with the prefix (+) or d are dextrorotatory. A specific stereoisomer is an enantiomer, and a mixture of such isomers is called an enantiomeric mixture. A 50:50 mixture of enantiomers is called a racemic mixture or racemate, which can occur when there is no stereoselectivity or stereospecificity in the chemical reaction or process.

[0057] Any asymmetric atom (e.g., carbon, etc.) in the compounds disclosed in this invention can exist in a racemic or enantiomerically enriched form, such as in (R)-, (S)-, or (R,S)- configurations. In some embodiments, each asymmetric atom has at least 50% enantiomeric excess, at least 60% enantiomeric excess, at least 70% enantiomeric excess, at least 80% enantiomeric excess, at least 90% enantiomeric excess, at least 95% enantiomeric excess, or at least 99% enantiomeric excess in the (R)- or (S)- configuration.

[0058] Depending on the choice of starting materials and methods, the compounds of this invention can exist as one or a mixture of possible isomers, such as racemic mixtures and mixtures of non-corresponding isomers (depending on the number of asymmetric carbon atoms). 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 substituents may be E or Z configurations; if the compound contains a disubstituted cycloalkyl group, the cycloalkyl substituents may be cis or trans configurations.

[0059] Any mixture of stereoisomers obtained can be separated into pure or substantially pure geometric isomers, enantiomers, and diastereomers based on differences in the physicochemical properties of the components, for example, by chromatography and / or fractional crystallization.

[0060] Racemic derivatives of any resulting end product or intermediate can be separated into optical enantiomers using known methods familiar to those skilled in the art, such as by separating the obtained diastereomeric salts. 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 via asymmetric synthesis.

[0061] As described in this invention, the compounds of this invention may optionally be substituted with one or more substituents, such as the general formula compounds above, or the specific examples, subclasses, and classes of compounds included in this invention, as described in the embodiments. It should be understood that the term "optionally substituted" is used interchangeably with the term "substituted or unsubstituted." Generally, the term "substituted" means that one or more hydrogen atoms in the given structure are substituted by a specific substituent. Unless otherwise indicated, an optional substituent group may be substituted at each substituted position of the group. When more than one position in the given structural formula can be substituted by one or more substituents selected from a specific group, the substituents may be substituted at the same or different positions. Specifically, examples of "one or more" refer to 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. The substituents described therein can be, but are not limited to, deuterium, fluorine, chlorine, bromine, iodine, cyano, hydroxyl, nitro, amino, carboxyl, alkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, alkoxyalkylamino, aryloxy, heteroaryloxy, heterocyclic alkoxy, arylalkoxy, heteroarylalkoxy, heterocyclic alkoxy, cycloalkylalkoxy, alkylamino, alkylaminoalkyl, alkylaminoalkylamino, cycloalkylalkylamino, alkylthio, haloalkyl, haloalkoxy, hydroxy-substituted alkyl, hydroxy-substituted alkylamino, cyano-substituted alkyl, cyano-substituted alkoxy, cyano-substituted alkylamino, amino-substituted alkyl, alkylacyl, heteroalkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, heterocyclic, heterocyclic alkyl, heterocyclic acyl, aryl, arylalkyl, arylamino, heteroaryl, heteroarylalkyl, heteroarylamino, amide, sulfonyl, aminosulfonyl, etc.

[0062] Additionally, it should be noted that, unless otherwise explicitly stated, the descriptive terms “each…independently is”, “…each independently is”, and “…independently is” used in this invention are interchangeable and should be interpreted broadly. They can mean that the specific options expressed by the same symbols in different groups do not affect each other, or that the specific options expressed by the same symbols in the same group do not affect each other.

[0063] In various parts of this specification, the substituents of the compounds disclosed herein are disclosed according to the type or scope of the groups. In particular, this invention includes every independent secondary combination of the various members of these group types and scopes. For example, the terms "C1-C6 alkyl" or "C..." 1-6 "Alkyl" specifically refers to independently disclosed methyl, ethyl, C3 alkyl, C4 alkyl, C5 alkyl, and C6 alkyl.

[0064] As used in this invention, the term "alkyl" or "alkyl group" refers to a saturated straight-chain or branched monovalent hydrocarbon group containing 1 to 20 carbon atoms; wherein the alkyl group is optionally substituted by one or more substituents described in this invention. Unless otherwise specified, the alkyl group contains 1 to 20 carbon atoms. In one embodiment, the alkyl group contains 1 to 12 carbon atoms; in another embodiment, the alkyl group contains 1 to 8 carbon atoms; in yet another embodiment, the alkyl group contains 1 to 6 carbon atoms; in still another embodiment, the alkyl group contains 1 to 4 carbon atoms; and in yet another embodiment, the alkyl group contains 1 to 3 carbon atoms.

[0065] Examples of alkyl groups include, but are not limited to, methyl (Me, -CH3), ethyl (Et, -CH2CH3), n-propyl (n-Pr, -CH2CH2CH3), isopropyl (i-Pr, -CH(CH3)2), n-butyl (n-Bu, -CH2CH2CH2CH3), isobutyl (i-Bu, -CH2CH(CH3)2), sec-butyl (s-Bu, -CH(CH3)CH2CH3), tert-butyl (t-Bu, -C(CH3)3), and so on. Pentyl (-CH2CH2CH2CH2CH3), 2-pentyl (-CH(CH3)CH2CH2CH3), 3-pentyl (-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-methyl-1-butyl (-CH2CH(CH3)CH2CH3), etc.

[0066] The term "alkoxy" indicates that an alkyl group is attached to the rest of the molecule by an oxygen atom, wherein the alkyl group has the meaning as described in this invention. Examples of alkoxy groups include, but are not limited to, methoxy (MeO, -OCH3), ethoxy (EtO, -OCH2CH3), 1-propoxy (n-PrO, n-propoxy, -OCH2CH2CH3), 2-propoxy (i-PrO, i-propoxy, -OCH(CH3)2), etc.

[0067] The term "alkylthio" indicates that an alkyl group is attached to the rest of the molecule via a sulfur atom, wherein the alkyl group has the meaning as described in this invention. Examples of alkylthio groups include, but are not limited to, -SCH3, -SCH2CH3, -SCH2CH2CH3, -SCH(CH3)2, etc.

[0068] The term "halogen" refers to fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0069] The term “halogenated alkyl” means that an alkyl group is replaced by one or more halogen atoms. Examples of such substitutions include, but are not limited to, -CF3, -CHF2, -CH2Cl, -CH2CF3, -CH2CHF2, -CH2CH2CF3, etc.

[0070] The term “haloalkoxy” means that the alkoxy group is replaced by one or more halogen atoms. Examples of such substitutions include, but are not limited to, -OCF3, -OCHF2, -OCHCl2, -OCH2CHF2, -OCH2CHCl2, -OCH(CH3)CHF2, etc.

[0071] The term "haloalkylthio" means that the alkylthio group is replaced by one or more halogen atoms.

[0072] The term "cyano" refers to -CN.

[0073] The term "hydroxyl group" refers to -OH.

[0074] The term "nitro" refers to -NO2.

[0075] The term "carboxyl group" refers to -COOH.

[0076] The term "amino" refers to -NH2.

[0077] The term "cycloalkyl" refers to a monovalent or polyvalent saturated monocyclic, bicyclic, or tricyclic system containing 3-12 carbon atoms. In one embodiment, the cycloalkyl group comprises 3-12 carbon atoms; in another embodiment, it comprises 3-10 carbon atoms; in yet another embodiment, it comprises 3-8 carbon atoms; and in still another embodiment, it comprises 3-6 carbon atoms. The cycloalkyl group may optionally be substituted by one or more substituents described in this invention. Examples of such substituents include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, adamantyl, etc.

[0078] The term "cycloalkyl-alkylene-" indicates that the cycloalkyl group is attached to the rest of the molecule via an alkylene group, wherein the alkylene and cycloalkyl groups have the meanings as described in this invention.

[0079] The term "cycloalkyloxy group" means that a cycloalkyl group is attached to the rest of the molecule by an oxygen atom, wherein the cycloalkyl group has the meaning as described in this invention.

[0080] The salts of the compounds described in this invention include those derived from alkali metals or alkaline earth metals, as well as those derived from ammonia and amines. Preferred cations include sodium, potassium, magnesium, and those having the chemical formula N. + (R AA R BB R CC R DD The ammonium cation of ) where R AA R BB R CC and R DD The compounds are independently selected from hydrogen, C1-C6 alkyl, and C1-C6 hydroxyalkyl. Salts of compounds having chemical formula (I) or (Ia) can be prepared by treating the compounds having chemical formula (I) or (Ia) with a metal hydroxide (e.g., sodium hydroxide) or an amine (e.g., ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, diallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine).

[0081] When the compounds of the present invention contain a base moiety, the 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, malonic 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 similarly known acceptable acids.

[0082] Compositions and formulations of the compounds of the present invention

[0083] The compounds of the present invention can generally be used as insecticidal active ingredients in compositions and / or formulations, and typically also include adjuvants commonly used in pesticide science, including surfactants and carriers.

[0084] The surfactants mentioned above can be various surfactants known in the field of pesticide formulation, and the present invention is preferably one or more of emulsifiers, dispersants and wetting agents.

[0085] Other carriers besides the surfactants mentioned above can be any type of carrier known in the field of pesticide formulation, including various silicates, carbonates, sulfates, oxides, phosphates, plant carriers, and synthetic carriers. Specifically, examples include: silica, kaolin, diatomaceous earth, clay, talc, organobentonite, pumice, titanium dioxide, dextrin, cellulose powder, light calcium carbonate, soluble starch, corn starch, sawdust, urea, amine fertilizer, mixtures of urea and amine fertilizer, glucose, maltose, sucrose, anhydrous potassium carbonate, anhydrous sodium carbonate, anhydrous potassium bicarbonate, anhydrous sodium bicarbonate, attapulgite, mixtures of anhydrous potassium carbonate and anhydrous potassium bicarbonate, and mixtures of anhydrous sodium carbonate and anhydrous sodium bicarbonate, or one or more of these.

[0086] The emulsifier mentioned above can be any emulsifier known in the field of pesticide formulation. Specifically, the emulsifier can be one or more of the following: calcium dodecylbenzenesulfonate, triphenylethylphenol polyoxyethylene ether phosphate, fatty alcohol polyoxyethylene ether, alkylphenol polyoxyethylene ether, alkylphenol polyoxyethylene polyoxypropylene ether, fatty amine, ethylene oxide adduct of fatty amide, fatty acid polyoxyethylene ester, rosin acid ethylene oxide adduct, polyol fatty acid ester and its ethylene oxide adduct, styrene-based phenyl polyoxyethylene ether, alkylphenol formaldehyde resin polyoxyethylene ether, hydroxyl-terminated polyoxyethylene polyoxypropylene ether, styrene-based phenol formaldehyde resin polyoxyethylene polyoxypropylene ether, and castor oil polyoxyethylene ether.

[0087] The dispersant mentioned above can be any dispersant known in the field of pesticide formulation. Specifically, the dispersant is one or more of the following: sodium salt of acrylic acid homopolymer, disodium salt of maleate, sodium salt of naphthalene sulfonate formaldehyde condensate, rosin block polyoxyethylene ether polyoxypropylene ether sulfonate, hydroxyl-terminated polyoxyethylene polyoxypropylene ether block copolymer, triphenylethylphenol polyoxyethylene ether phosphate, fatty alcohol polyoxyethylene ether phosphate, and sodium salt of p-hydroxyphenyl lignin sulfonate.

[0088] The aforementioned wetting agent can be any wetting agent known in the field of pesticide formulation. Specifically, the wetting agent can be one or more of sodium dodecyl sulfate, sodium secondary alkyl sulfate, sodium dodecylbenzene sulfonate, fatty alcohol polyoxyethylene ether, alkyl naphthalene sulfonate, and alkylphenol resin polyoxyethylene ether sulfate.

[0089] According to the insecticide composition of the present invention, the insecticide composition may further contain various formulation adjuvants commonly used in the field of pesticide formulation. Specifically, the formulation adjuvant may be one or more of solvents, cosolvents, thickeners, antifreeze agents, encapsulating materials, protectants, defoamers, disintegrants, stabilizers, preservatives, and binders.

[0090] The solvents mentioned above can be various solvents known in the field of pesticide formulations. Specifically, the solvent can be one or more of organic solvents, vegetable oils, mineral oils, solvent oils, and water.

[0091] The organic solvent includes one or more of N-methylpyrrolidone, tetrahydrofuran, dimethyl sulfoxide, N,N-dimethyldecylamide, N,N-dimethylformamide, trimethylbenzene, tetramethylbenzene, xylene, toluene, octane, heptane, methanol, isopropanol, n-butanol, tetrahydrofurfuryl alcohol, tributyl phosphate, 1,4-dioxane, and cyclohexanone.

[0092] The vegetable oils include one or more of the following: methylated vegetable oils, rosin-based vegetable oils, turpentine oil, epoxidized soybean oil, soybean oil, peanut oil, rapeseed oil, castor oil, corn oil, and pine nut oil.

[0093] The mineral oil includes one or more of liquid wax, engine oil, kerosene, and lubricating oil.

[0094] In addition, the above solvents can also be used as cosolvents.

[0095] The antifreeze agent mentioned above can be any antifreeze agent known in the field of pesticide formulation, and the present invention preferably includes one or more of ethylene glycol, propylene glycol, glycerin and urea.

[0096] The aforementioned thickener can be any thickener known in the field of pesticide formulation. Specifically, the thickener can be one or more of xanthan gum, polyvinyl alcohol, polyacryl alcohol, polyethylene glycol, silica, diatomaceous earth, kaolin, clay, sodium alginate, magnesium aluminum silicate, sodium aluminum silicate, carboxymethyl cellulose, sodium hydroxypropyl cellulose, and organobentonite.

[0097] The aforementioned encapsulating material can be any of the encapsulating materials known in the field of pesticide formulations, and the present invention preferably uses one or more of polyurethane, polyurea, and urea-formaldehyde resin.

[0098] The aforementioned protective agent can be any of the protective agents known in the field of pesticide formulation, and the present invention preferably uses polyvinyl alcohol and / or polyethylene glycol.

[0099] The defoamer mentioned above can be any defoamer known in the field of pesticide formulations. The present invention preferably includes one or more of organosiloxanes, tributyl phosphate and silicones.

[0100] The stabilizer is selected from one or more of triphenyl phosphite, epichlorohydrin, and acetic anhydride.

[0101] The above-mentioned preservatives are selected from one or more of benzoic acid, sodium benzoate, 1,2-benzisothiazolin-3-one (BIT), Kathon and potassium sorbate.

[0102] This invention also provides a formulation prepared from the above-described insecticide composition, wherein the formulation is in the form of an emulsifiable concentrate, an emulsion, a microemulsion, a soluble liquid, an aqueous suspension, a suspension emulsion, an ultra-low volume spray, an oil suspension, a microcapsule suspension, a water-spreading oil, a wettable powder, a water-dispersible granule, a dry suspension, a soluble powder, a soluble granule, an emulsifiable powder, an emulsifiable granule, granules, a solid microcapsule formulation, an effervescent tablet, an effervescent granule, a water-floating dispersible granule, or a seed coating agent. All of the above formulations can be prepared by conventional methods in the art.

[0103] The preparation method of the above-mentioned emulsifiable concentrate formulation may include mixing and stirring the active components, solvent, cosolvent and emulsifier to form a uniform and transparent oil phase, thereby obtaining the emulsifiable concentrate formulation.

[0104] The above-mentioned method for preparing water-in-water emulsions may include, for example, mixing active ingredients, emulsifiers, co-solvents, and solvents to form a homogeneous oil phase; or mixing water, thickeners, antifreeze, etc., to form a homogeneous aqueous phase. Under high-speed shearing, the aqueous phase is added to the oil phase or the oil phase is added to the aqueous phase to form a well-dispersible water-in-water emulsion.

[0105] The preparation method of the above-mentioned microemulsion may include, for example, mixing and stirring the active ingredient, emulsifier, and solvent to form a homogeneous and transparent oil phase. Under stirring conditions, water is gradually added to form a homogeneous and transparent microemulsion.

[0106] The preparation method of the above-mentioned water / oil suspension is as follows: For example, water or oil can be used as the medium. The active component, surfactant, and other additives are added to a sand mill and ground to a certain particle size, then filtered. A metered thickener is then added to the ground mother liquor and sheared to disperse it evenly. This produces an oil suspension or a water suspension.

[0107] The preparation methods of the above-mentioned water-dispersible granules and soluble granules are as follows: For example, the active components, dispersants, wetting agents, carriers, etc. are mixed evenly, then pulverized to a certain particle size by airflow, water is added and kneaded, and finally added to a granulator for granulation. After drying, water-dispersible granules or soluble granules can be obtained.

[0108] The preparation methods of the above-mentioned soluble powders and wettable powders include, for example, thoroughly mixing each active component, various additives and other carriers and fillers, and then pulverizing them using an ultrafine pulverizer.

[0109] The insecticide composition of the present invention can be provided as a finished formulation, i.e., the substances in the composition have been mixed; or it can be provided as a separate formulation, which can be mixed in a bucket or can before use and selectively diluted with water according to the desired concentration of active substances.

[0110] For further information related to the formulation field, see T.S. Woods, “The Formulator’s Toolbox – Product Forms for Modern Agriculture,” Pesticide Chemistry and Bioscience, The Food-Environment Challenge, edited by T. Brooks and TR. Roberts, Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120–133. See also US 3,235,361, column 6, lines 16-7, line 19 and Examples 10-41; U.S. 3,309,192, column 5, lines 43-7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; US 2,891,855, column 3, lines 66-5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp. 81-96; Hance et al., Weed Control Handbook, 8th edition, Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB. Publications, Richmond, UK, 2000.

[0111] Application of the compounds and compositions of the present invention

[0112] The compounds and / or compositions of the present invention are suitable for controlling pests in useful plants, such as arthropods, gastropods, and nematodes, including but not limited to:

[0113] Homoptera, for example: whitefly (Aleurodes brassicae), smoke fly (Bemisiatabaci), greenhouse whitefly (Trialeurodes vaporariorum), cotton aphid (Aphis gossypii), cabbage aphid (Brevicoryne brassicae), burcher aphid (Cryptomyzus ribis), black bean aphid (Aphis fabae), apple yellow aphid (Aphis pomi), apple woolly aphid (Eriosoma lanigerum), plum aphid (Hyalopterusarundinis), grape root phylloxera (Phylloxera vastatrix), gall aphid (Pemphigus spp.), wheat long-tube aphid (Macrosiphum avenae), gall aphid (Myzus spp.), hopa humuli, rice constrictor aphid (Rhopalosiphum padi), small green leafhopper (Empoasca spp.), Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvatalugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

[0114] Hemiptera: Planthoppers (Delphacidae) such as the brown planthopper (Nilaparvatalugens) and the small gray planthopper (Laodelphax striatellus); leafhoppers (Deltecephalidae) such as the green rice leafhopper (Nephotettix cincticeps); aphids (Aphididae) such as the cotton aphid (Aphisgossypii) and the alfalfa aphid (Aphis craccivora Koch); stink bugs (Pentatomidae) such as the green stink bug (Nezaraantennata); whiteflies (Aleyrodidae) such as the greenhouse whitefly (Trialeurodes vaporariorum); scale insects (Coccidae) such as the California red scale (Calformia red scale) (Aonidiella). aurantii); Tingidae; Homoptera, Psyllidea;

[0115] Lepidoptera: Pyralidae moths such as the rice stem borer (Chilo suppressalis); Noctuidae moths such as the fall armyworm (Spodoptera litura), armyworm (Pseudaletia separata), *Heliothis* spp., and *Helicoverpa* spp.; Pieridae butterflies such as the cabbage white butterfly (Pierisrapae); Tortricidae moths such as the brown-banded leafroller (Adoxophyes); Gracillariidae moths such as the tea leafroller (Caloptilia theivora) and the apple leafroller (Phyllonorycter ringoneella); Carposinidae moths such as the peach leafroller (Carposina niponensis); Lyonetiidae moths such as the genus *Lyonetia*. spp.); tussock moths (Lymantriidae) such as the genera *Lymantria* spp. and *Euproctis* spp.; nest moths (Yponomeutidae) such as the diamondback moth (*Plutella xylostella*); wheat moths (Gelechiidae) such as the red boll moth (*Pectinophora gossypiella*) and the potato moth (*Phthorimaea operculella*); light moths (Arctiidae) such as the fall webworm (*Hyphantria cunea*); and grain moths (Tineidae) such as the clothes moth (*Tinea translucens*) and the curtain grain moth (*Tineola bisselliella*);

[0116] Thysanoptera: Western flower thrips (Frankliniella occidentalis), palm thrips (Thrips palmi), yellow hard thrips (Scirtothrips dorsalis), tobacco thrips (Thrips tabaci), beautiful flower thrips (Frankliniella intonsa), and potato thrips (Frankliniella fusca);

[0117] Diptera: Housefly (Musca domestica), Culex popienspallens, Tabanus trigonus, Onion fly (Hylemya anitqua), Grey ground fly (Hylemyaplatura), Anopheles sinensis, Japanese rice leafminer (Agromyza oryzae), Rice leafminer (Hydrellia griseola), Rice straw fly (Chlorops oryzae), Melon fruit fly (Dacus cucurbitae), Mediterranean fruit fly (Ceratitis capitata), and Clover leafminer (Liriomyza trifolii);

[0118] Coleoptera: *Epilachna vigintioctopunctata*, *Phyllotreta striolata*, *Oulema oryzae*, *Echinocnemus squameus*, *Lissorhoptrus oryzophilus*, *Anthonomus grandis*, *Callosobruchus chinensis*, *Sphenophorus venatus*, *Popillia japonica*, *Anomala cuprea*, *Diabrotica spp.*, *Leptinotarsa ​​decemlineata*, *Agriotes spp.*, *Lasioderma serricorne*, *Anthrenus* The species include verbasci, Tribolium castaneum, Lyctus brunneus, Anoplophora malasiaca, and Tomicus piniperda.

[0119] Orthoptera: Locusta migratoria, Gryllotalpaafficana, Oxya yezoensis, and Oxya japanica;

[0120] Hymenoptera: Xinjiang cabbage bee (Athalia rosae), leafcutter ant (Acromyrmex spp.), and fire ant (Solenopsis spp.);

[0121] Nematodes: Rice stem tip nematode (Aphelenchoides besseyi), strawberry bud nematode (Nothotylenchus acris), soybean cyst nematode (Heterodera glycines), southern root-knot nematode (Meloidogyne incognita), short-bodied nematode (Pratylenchus penetrans), and abnormal pearl nematode (Nacobbus aberrans);

[0122] Blattariae: German cockroach (Blattella germanica), black-breasted cockroach (Periplaneta fulliginosa), American cockroach (Periplaneta Americana), brown-spotted cockroach (Periplaneta brunnea), and oriental cockroach (Blatta orientalis);

[0123] Order Acarina: Tetranychidae (e.g., Tetranychus cinnabarinus, Tetranychusurticae, Panonychus citri, and Oligoychus spp.)); Eriophyidae (e.g., Aculops pelekassi)); Tarsonemidae; Tenuipalpidae; Tuckerellidae; Tuckerellidae Acaridae; Pyroglyphidae (e.g., Dermatophagoides farinae and Dermatophagoides ptrenyssnus)); Cheyletidae; Cheyletus malaccensis and Cheyletus moorei; and Dermanyssidae.

[0124] Within the scope of this invention, useful plants include the following plant species: cereals (wheat, barley, rye, oats, rice, corn, sorghum, and related species); sugar beets (sugar beets and forage sugar beets); pome fruits, stone fruits, and soft fruits (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, and blackberries); legumes (lentils, beans, peas, soybeans); oil crops (rapeseed, mustard, olives, sunflowers, coconuts, castor oil plants, cocoa beans, peanuts, or soybeans); and cucurbits (pumpkins, cucumbers, melons). ; fiber plants (cotton, flax, hemp, jute); citrus fruits (oranges, lemons, grapefruits, tangerines); vegetables (spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, red peppers); laurel plants (avocados, camphor, camphor) or plants such as tobacco, nuts, coffee, eggplant, sugarcane, tea, pepper, grapevines, hops, bananas, and natural rubber plants, along with turf, ornamental and forest plants such as flowers, shrubs, broad-leaved trees or evergreen trees such as conifers, and plant propagation materials.

[0125] The term “plant propagation material” should be understood to refer to the reproductive parts of the plant, such as seeds, which can be used for the propagation of the plant, as well as nutrient materials, such as cuttings or tubers (e.g., potatoes).

[0126] The compounds and / or compositions of the present invention can kill pests with an effective amount of active substance. Among them, the effective amount of the compound of formula (I) or (Ia) is within 10g-5kg per hectare, and the effect of controlling pests is better.

[0127] The present invention also relates to a method for controlling pests, said method by applying the compounds or compositions of the present invention to seeds, plants or plant parts, fruits or the soil in which plants grow. Application can be carried out before and after the seeds, plants or plant parts, fruits or the soil in which plants grow are infected by pests.

[0128] The term "effective amount" as used refers to the amount of the compound or composition of the present invention sufficient to control pests on cultivated plants or in the protection of materials without causing significant damage to the treated plants. This amount can vary over a wide range and depends on various factors such as the pest species, the cultivated plant or material being treated, climatic conditions, and the specific compound used.

[0129] The method of using the compounds and / or compositions of the present invention is simple: apply the compounds and / or compositions of the present invention to the pests or their growth media. The dosage of the compounds and / or compositions of the present invention varies depending on weather conditions, formulation, timing of application, method of application, area covered, target disease, and target crop.

[0130] General Synthesis Process

[0131] The following describes the preparation of the compounds of the present invention. Unless otherwise specified, the compounds of the present invention can be prepared by the methods described herein. The raw materials, reagents, etc., used to prepare the compounds of the present invention are commercially available or can be prepared by conventional methods in the art. In this specification, if there are any differences between chemical names and chemical structures, the structure is preferred.

[0132] The testing conditions for the proton NMR spectra of this invention are as follows: room temperature, Bruker 400MHz or 600MHz NMR spectrometer, using CDCl3, d6-DMSO, CD3OD, or d6-acetone as solvents (reported in ppm), and TMS (0ppm) or chloroform (7.26ppm) as reference standards. When multiplets are observed, the following abbreviations will be used: s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet), br (broadened), dd (doublet of doublets), dt (doublet of triplets). The coupling constant J is expressed in Hertz (Hz).

[0133] The mass spectrometry analysis methods used in this invention are: Agilent 1260 HPLC; Agilent 6120 ESI.

[0134] Phase A: Water (containing 0.1% formic acid); Phase B: Acetonitrile (containing 0.1% formic acid).

[0135] Gradient elution: 0-3 min, 5-100% B; 3-6 min, 100% B.

[0136] Flow rate: 0.6 mL / min.

[0137] Detection wavelength: 254nm.

[0138] MS parameters: ESI positive scan, collision-induced ionization: 70V.

[0139] Dry nitrogen: 12 L / min, atomizing gas pressure: 40 psi, gas temperature: 350 °C.

[0140] Take an appropriate amount of sample, dissolve it in 0.5 mL of methanol, inject the sample, and perform a single-stage MS full scan in positive ESI mode to obtain the quasi-molecular ion peak [M+1]. + reading.

[0141] The following abbreviations are explained throughout this invention:

[0142] DMSO: Dimethyl sulfoxide;

[0143] g: gram; mg: milligram; mol: mole; mmol: millimole; M: mol / L, mol / liter; mL: milliliter.

[0144] "Room temperature" means a temperature of approximately 0°C-40°C, approximately 20°C-30°C, approximately 23°C-28°C, or approximately 25°C. In the context of this invention, all figures disclosed herein are approximate values, regardless of whether the words "approximately" or "about" are used.

[0145] Synthesis Scheme 1

[0146]

[0147] The target compound shown in formula (I) can be prepared by synthetic scheme one. The compound shown in formula (a) reacts with the compound shown in formula (b) under high temperature conditions (70-120℃) to obtain the target compound shown in formula (I);

[0148] Among them, R 1 R 2 R 3 R 4 R 5 R 6 A and A have the meanings described in this invention. Specific Implementation

[0149] Example 1: Preparation of 4-(((6-fluoropyridin-3-yl)methyl)(6-fluoropyridin-3-yl)amino)furan-2(5H)-one

[0150]

[0151] Step 1: Preparation of methyl 2-methoxy-2-oxoethylmalonate

[0152]

[0153] Potassium monomethyl malonate (1092 mg, 7 mmol) was dissolved in N,N-dimethylformamide (20 mL) at room temperature and heated to 35 °C. Methyl bromoacetate (0.62 mL, 6.72 mmol) was then added dropwise, and the reaction was continued at 35 °C for 8 hours after the addition was complete. After the reaction was complete, the solvent was removed by vacuum distillation, water (50 mL) was added, and the mixture was extracted with ethyl acetate (30 mL x 3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give 1252 mg of a colorless oily liquid, with a yield of 98%.

[0154] Step 2: Preparation of sodium methyl 4-hydroxy-2-oxo-2,5-dihydro-3-furanoate

[0155]

[0156] At room temperature, methyl 2-methoxy-2-oxoethyl malonate (1207 mg, 6.35 mmol) was dissolved in anhydrous methanol (20 mL), heated to 40 °C, and a methanol solution of sodium methoxide (411 mg, 7.62 mmol) (10 mL) was added dropwise. After the addition was complete, the resulting mixture was heated to 70 °C and refluxed for 3 hours, cooled to 0 °C, filtered, and the filter cake was washed with dichloromethane (25 mL). After vacuum drying at 50 °C, 720 mg of white solid was obtained, with a yield of 63%.

[0157] Step 3: Preparation of N-((6-fluoropyridin-3-yl)methyl)-6-fluoropyridin-3-amine

[0158]

[0159] 2-Fluoro-5-aminopyridine (336 mg, 3 mmol) was dissolved in anhydrous methanol (20 mL), and then 6-fluoropyridine-3-carboxaldehyde (450 mg, 3.6 mmol) was added. The resulting mixture was reacted overnight at room temperature. Then, sodium borohydride (340 mg, 9 mmol) was slowly added in portions at 0 °C. After the reaction was complete, the solvent was removed by vacuum distillation, water (50 mL) was added, and the mixture was extracted with ethyl acetate (30 mL x 3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give 640 mg of a light red solid, with a yield of 97%.

[0160] Step 4: Preparation of 4-(((6-fluoropyridin-3-yl)methyl)(6-fluoropyridin-3-yl)amino)furan-2(5H)-one

[0161]

[0162] N-((6-fluoropyridin-3-yl)methyl)-6-fluoropyridin-3-amine (660 mg, 3 mmol) was dissolved in butyronitrile (10 mL), followed by the addition of sodium methyl 4-hydroxy-2-oxo-2,5-dihydro-3-furanose (720 mg, 4 mmol) and potassium hydrogen sulfate (1089 mg, 8 mmol), and the reaction was heated to 95 °C. The reaction was monitored by TLC. After the reaction was completed, the reaction system was cooled to room temperature and poured directly into water (45 mL). The mixture was extracted with ethyl acetate (25 mL × 3), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was separated by column chromatography [petroleum ether / ethyl acetate (v / v) = 1 / 3] to give 110 mg of white solid, yield 12.1%.

[0163] 1H NMR (400MHz, DMSO-d6) δ (ppm): 8.27 (d, J = 2.0 Hz, 1H), 8.16 (s, 1H), 8.06-8.00 (m, 1H), 7.93 (td, J = 8.2, 2. 4Hz, 1H), 7.26 (dd, J=8.7, 3.1Hz, 1H), 7.16 (dd, J=8.4, 2.7Hz, 1H), 5.06 (s, 1H), 4.94 (s, 2H), 4.72 (s, 2H).

[0164] MS(ES-API,pos.ion)m / z:304.10[M+1] + .

[0165] Referring to the synthesis method of Example 1, and combining with the synthesis scheme of the present invention, using the corresponding raw materials and conditions, or referring to the preparation methods in the prior art, the target compounds in Table 1 can be obtained.

[0166] Table 1

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174] Bioactivity test

[0175] 1) Experimental Method - Target Specimen: Alfalfa Aphid

[0176] Spraying method: Select cowpea leaves of uniform growth and make leaf discs using a perforator, two leaf discs per dish. Place a damp sponge block in the petri dish, place the leaf discs on the sponge, and add water until it is level with the leaf discs. Inoculate 2nd-3rd instar alfalfa aphids raised indoors onto the prepared leaf discs, at least 15 aphids per disc. Use a spray tower for treatment, spraying 0.5 mL of pesticide solution per treatment. Place the treated materials in an observation room and observe the results after 2 days. Touch the insects with a brush; no reaction indicates dead insects. The experimental concentration is 50 mg / L.

[0177] The test results showed that the compound of the present invention has certain biological activity against alfalfa aphids at a dose of 50 mg / L. Specifically, the control efficacy against alfalfa aphids in Examples 15 and 19 was more than 75%, while the control efficacy against alfalfa aphids in Example 12 was 50%, and the control efficacy against alfalfa aphids in Example 13 was 30%.

[0178] 2) Experimental Method - Target Peach Aphid

[0179] Spraying method: Select uniformly growing cowpea leaves and make leaf discs using a perforator, two leaf discs per dish. Place a damp sponge block in the petri dish, place the leaf discs on the sponge, and add water until it is level with the leaf discs. Inoculate 2nd-3rd instar peach aphids (raised indoors) onto the prepared leaf discs, at least 15 aphids per disc. Use a spray tower for treatment, spraying 0.5 mL of pesticide solution per treatment. Place the treated materials in an observation room and observe the results after 2 days. Touch the insects with a brush; no reaction indicates dead insects. The experimental concentration is 50 mg / L.

[0180] The test results showed that the compound of the present invention has certain biological activity against peach aphids at a dose of 50 mg / L. Specifically, Example 15 showed an efficacy of 80% against peach aphids; Examples 9, 10, and 25 showed an efficacy of 100% against peach aphids; Example 12 showed an efficacy of 50% against peach aphids; and Example 13 showed an efficacy of 0% against peach aphids.

[0181] 3) Experimental Method - Test Target: Whitefly (1st Instar)

[0182] Spraying method: Eggplant seedlings with uniform growth were placed in whitefly rearing cages. After 24 hours, the plants that had laid eggs were transferred to insect-free cages for normal cultivation. When the nymphs reached the first instar, samples were taken using a 12mm diameter punch. The sampled leaf discs were placed in 9cm petri dishes (moistened with agar). The number of nymphs was counted under a stereomicroscope. Then, the prepared pesticide solution was sprayed using a potter sprayer. After air-drying, the plants were placed in an artificial climate chamber. After 3 days, the number of dead and live nymphs was counted under a stereomicroscope, and the mortality rate was calculated. The experimental concentration was 50mg / L.

[0183] The test results showed that the compound of the present invention had good activity against whiteflies (1st instar) at a dose of 50 mg / L. Among them, the control efficacy of Examples 1, 2, 3, 5, 6, 8 and 9 against whiteflies (1st instar) was 100%; the control efficacy of Examples 7, 10 and 11 against whiteflies (1st instar) was 90%.

[0184] 4) Experimental Method - Target: Whitefly (adult)

[0185] Spraying method: Eggplant seedlings with uniform growth were placed in whitefly rearing cages. After 24 hours, the plants that had laid eggs were transferred to insect-free cages for normal cultivation. When the nymphs grew into adults, samples were taken using a 12mm diameter punch. The sampled leaf discs were placed in 9cm petri dishes (moistened with agar). The number of adults was counted under a stereomicroscope. Then, the prepared pesticide solution was sprayed using a potter sprayer. After air-drying, the plants were placed in an artificial climate chamber. After 3 days, the number of dead and live adults was counted under a stereomicroscope, and the mortality rate was calculated. The experimental concentration was 50mg / L.

[0186] The test results showed that the compound of the present invention had good activity against whiteflies (adults) at a dose of 50 mg / L. Among them, the control efficacy of Examples 20, 24 and 25 against whiteflies (adults) was more than 75%, while the control efficacy of Example 12 against whiteflies (adults) was 20%, and the control efficacy of Example 13 against whiteflies (adults) was 25%.

[0187] The preferred embodiments of the present invention have been described in detail above. However, the present invention is not limited to the specific details in the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all fall within the protection scope of the present invention.

Claims

1. A compound having one of the following structures or a salt thereof: (1) (2) (3) (5) (6) (7) (8) (9) (10) (11) (15) (19) (20) (24) or (25).

2. A composition comprising the compound of claim 1 and at least one pesticide-acceptable adjuvant.

3. The use of the compound of claim 1 or the composition of claim 2 as a pest control agent in agriculture, forestry, or horticulture, wherein, The pests mentioned are alfalfa aphids, peach aphids, and / or whiteflies.

4. A method for controlling pests, the method comprising applying an effective amount of the compound of claim 1 or the composition of claim 2 to the pest or the location of the pest, wherein, The pests mentioned are alfalfa aphids, peach aphids, and / or whiteflies.

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