Amide compound and / or salt thereof and application thereof

Abstract

The invention relates to the field of pesticide chemistry, and discloses an amide compound and / or salt thereof and application thereof. The compound has a structure as shown in a formula (1), and the compound and / or the salt thereof and the composition comprising the compound and / or the salt thereof have excellent insecticidal and bactericidal effects and have wide application prospects in the aspect of preventing and treating diseases and insect pests of crops. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to the field of pesticide chemistry, and in particular to an amide compound and / or its salt and application thereof. Background Art

[0002] Amide compounds are used for sterilization mainly by hindering the electron transfer of succinate dehydrogenase in the respiratory chain and inhibiting mitochondrial respiration, and have the characteristics of broad bactericidal spectrum and good bactericidal effect. At the same time, it is also reported in the prior art that amide compounds have good insecticidal effects. However, there are few reports on amide compounds with excellent bactericidal effects and good insecticidal effects. Therefore, a compound and / or its salt having excellent bactericidal effects and good insecticidal effects is needed. Summary of the invention

[0003] The purpose of the present invention is to overcome the problem that the prior art cannot achieve both excellent bactericidal and insecticidal effects, and to provide a compound and / or its salt and application thereof.

[0004] In order to achieve the above object, the present invention provides an amide compound and / or its salt in a first aspect, wherein the compound has a structure shown in formula (1):

[0005]

[0006] Wherein, R1 is selected from H, halogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted aryl, or R1 and the carbon atom directly connected thereto are combined to form a 3-8 membered ring structure containing or not containing heteroatoms;

[0007] R2 and R3 are each independently selected from halogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclyl, substituted or unsubstituted aryl;

[0008] X is selected from halogen;

[0009] Wherein, the substituted substituent is selected from halogen, C1-C8 alkyl, halogenated C1-C8 alkyl, cyano, and cyano.

[0010] The second aspect of the present invention provides a composition, wherein the composition comprises an auxiliary agent and the compound and / or its salt described in the first aspect of the present invention; wherein the auxiliary agent is selected from at least one of a surfactant, a solid diluent and a liquid diluent.

[0011] The third aspect of the present invention provides a use of the compound and / or its salt described in the first aspect of the present invention and the composition described in the second aspect of the present invention in preventing and controlling plant fungal and insect pests.

[0012] Through the above technical scheme, the amide compounds and / or their salts and the compositions comprising the compounds and / or their salts described in the present invention have excellent insecticidal and fungicidal effects and have broad application prospects in preventing and controlling diseases and insect pests of crops. DETAILED DESCRIPTION

[0013] The endpoints and any values ​​of the ranges disclosed in this article are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of each range, the endpoint values ​​of each range and the individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed in this article.

[0014] As mentioned above, the first aspect of the present invention provides an amide compound and / or its salt, wherein the compound has a structure shown in formula (1):

[0015]

[0016] Wherein, R1 is selected from H, halogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted aryl, or R1 and the carbon atom directly connected thereto are combined to form a 3-8 membered ring structure containing or not containing heteroatoms;

[0017] R2 and R3 are each independently selected from halogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclyl, substituted or unsubstituted aryl;

[0018] X is selected from halogen;

[0019] Wherein, the substituted substituent is selected from halogen, C1-C8 alkyl, halogenated C1-C8 alkyl, and cyano.

[0020] In some embodiments of the present invention, preferably, R1 is selected from H, halogen, substituted C1-C8 alkyl, substituted C3-C8 cycloalkyl, substituted aryl, or R1 and the carbon atom directly connected thereto are combined to form a 3-8 membered ring structure containing or not containing heteroatoms;

[0021] R2 and R3 are each independently selected from halogen, substituted C1-C8 alkyl, substituted C3-C8 cycloalkyl, substituted C3-C8 heterocyclyl, substituted aryl;

[0022] X is selected from halogen;

[0023] Wherein, the substituted substituent is selected from halogen, halogenated C1-C8 alkyl, and cyano.

[0024] In some embodiments of the present invention, preferably, R1 is selected from H, halogen, or R1 and the carbon atom directly connected thereto are combined to form a 3-8 membered ring structure containing or not containing heteroatoms; more preferably, R1 is selected from H, or R1 and the carbon atom directly connected thereto are combined to form a 3-8 membered ring structure containing or not containing oxygen atoms;

[0025] In some embodiments of the present invention, preferably, R2 and R3 are each independently selected from halogen, substituted C1-C6 alkyl, substituted C3-C6 cycloalkyl, substituted C3-C8 heterocyclyl, substituted phenyl; more preferably, R2 and R3 are each independently selected from halogen, halogenated C1-C4 alkyl or cyano substituted C3-C6 cycloalkyl;

[0026] Wherein, the substituted substituent is selected from halogen, halogenated C1-C8 alkyl, and cyano.

[0027] In some embodiments of the present invention, preferably, X is fluorine or chlorine; more preferably, X is fluorine.

[0028] In some embodiments of the present invention, preferably, the compound has a structure shown in formula (1-1) to (1-3):

[0029]

[0030] General synthesis process

[0031] In this specification, if there is any difference between chemical name and chemical structure, the structure is dominant. Generally, the compounds of the present invention can be prepared by the methods described in the present invention, unless further specified. The following synthetic schemes and examples are used to further illustrate the content of the present invention.

[0032] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many other compounds of the invention, and other methods for preparing the compounds of the invention are considered to be within the scope of the invention. For example, the synthesis of non-exemplified compounds according to the invention can be successfully accomplished by those skilled in the art through modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents (except 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 recognized to be applicable to the preparation of other compounds of the invention.

[0033] Synthesis scheme

[0034]

[0035] Wherein, R4 is hydroxyl or chlorine; the definitions of R1, R2 and R3 are the same as those described in the first aspect of the present invention.

[0036] One synthesis process is that the compound of formula 3 and the compound of formula 2 undergo a condensation reaction in the presence of a first alkaline substance and a condensation agent to generate compound 1.

[0037] In some embodiments of the present invention, preferably, the condensing agent is selected from at least one of HATU, HOBT, PyBOP and EDCI.

[0038] In some embodiments of the present invention, preferably, the first alkaline substance is selected from at least one of triethylamine, pyridine, potassium carbonate and sodium carbonate.

[0039] In some embodiments of the present invention, preferably, the temperature of the condensation reaction is 20-40° C. This temperature range can make the condensation reaction complete with less by-products.

[0040] Another synthesis process is that the compound of formula 3 reacts with an acylating agent to generate an acyl chloride, and the acylated product reacts with the compound of formula 2 in the presence of a second alkaline substance to generate compound 1.

[0041] In some embodiments of the present invention, preferably, the acylating agent is thionyl chloride or oxalyl chloride.

[0042] In some embodiments of the present invention, preferably, the solvent for the acylation reaction is selected from at least one of dichloroethane, dichloromethane, toluene, chloroform and chlorobenzene.

[0043] In some embodiments of the present invention, preferably, the second alkaline substance in the acylation reaction is selected from at least one of triethylamine, pyridine, potassium carbonate and sodium carbonate.

[0044] In some embodiments of the present invention, preferably, the temperature of the acylation reaction is 20-80° C. This temperature range allows the acylation reaction to be completed with less by-products.

[0045] The second aspect of the present invention provides a composition, wherein the composition comprises an auxiliary agent and the compound and / or its salt described in the first aspect of the present invention; wherein the auxiliary agent is selected from at least one of a surfactant, a solid diluent and a liquid diluent.

[0046] In some embodiments of the present invention, preferably, the surfactant is selected from ionic surfactants and / or nonionic surfactants; further preferably, the reaction product of polyalkylene glycol ethers of linear or branched alcohols, fatty acid amines and ethylene oxide and / or propylene oxide, alkyl sulfonates, alkyl sulfates, alkyl ether sulfates, alkyl ether phosphates, aryl sulfates, polyacrylates, lignin sulfonates, benzene sulfonates, salts of sulfosuccinates, taurine derivatives, substituted phenols, gelatin, gum arabic, phospholipids, starch, cellulose derivatives, polyvinyl alcohol, polyvinyl acetate, polyvinyl pyrrolidone, polyacrylic acid, polymethacrylic acid, copolymers of (meth) acrylic acid and (meth) acrylic acid esters, polyoxyethylene. At least one of phosphate esters of ethylated alcohols or phenols, fatty acid esters of polyols, taurine alkyl esters, copolymers of methacrylic acid and methacrylic acid esters neutralized with alkali metal hydroxides, condensates of substituted naphthalenesulfonates and formaldehyde, and derivatives of the above compounds containing sulfate, sulfonate and phosphate functional groups; more preferably at least one of ethoxylated aryl alkylphenols, ethoxylated aryl alkylphenols, propoxylated aryl alkylphenols, aryl alkylphenol-ethoxy-propoxylates, tristyryl-phenol-ethoxylates, hydrophobically modified starches, cellulose esters, cellulose ethers, sulfated aryl alkylphenol-ethoxylates, phosphorylated aryl alkylphenol-ethoxylates and ethoxylated nonylphenols.

[0047] The surfactant may play the roles of adjuvant, emulsifier, protective colloid, dispersion, stabilization, wetting and adhesion in the composition.

[0048] In some embodiments of the present invention, optionally, the composition includes an auxiliary agent, wherein the auxiliary agent is selected from at least one of an adhesive, a defoamer, a foaming agent, an antioxidant, a crystallization inhibitor, a viscosity regulator, a suspending agent, a spray drop regulator, a pigment, a neutralizer, a buffer, a corrosion inhibitor, a dye, a flavoring agent, a spreading agent, a penetration aid, a trace nutrient, a dispersant, a thickener, a freezing point depressant and an antimicrobial agent.

[0049] In some embodiments of the present invention, preferably, the solid diluent is selected from silicates; further preferably, it is at least one of talc, kaolinite, kaolin, montmorillonite, mica, white carbon black, limestone, sodium sulfate and ammonium salts; more preferably, it is at least one of calcium carbonate, calcium sulfate, magnesium silicate, magnesium aluminosilicate, ammonium sulfate, hexamethylenediamine and urea.

[0050] In some embodiments of the present invention, preferably, the liquid diluent is selected from water and organic solvents; more preferably, it is at least one of water, aromatic hydrocarbons, halogenated hydrocarbons, unsubstituted hydrocarbons, alcohols, ethers, esters, ketones, aldehydes and vegetable oils; more preferably, it is at least one of benzene, xylene, toluene, chlorobenzene, vinyl chloride, chloroform, dichloromethane, cyclohexane, light mineral oil, isopropanol, butanol, ethylene glycol, glycerol, cyclohexanol, acetone, cyclohexanone, dimethylformamide, N-methylpyrrolidone, soybean oil, rapeseed oil and cottonseed oil. The liquid diluent can play the role of antifreeze additive, gaseous filler and aerosol propellant.

[0051] In some embodiments of the present invention, preferably, the mass ratio of the compound and / or its salt to the auxiliary agent is 1:1-10, more preferably 1:1-3.

[0052] The third aspect of the present invention provides a use of the compound and / or its salt described in the first aspect of the present invention and the composition described in the second aspect of the present invention in preventing and controlling plant fungal and insect pests.

[0053] In some embodiments of the present invention, preferably, the fungal pest is Bletilla striata of the Poaceae family.

[0054] In some embodiments of the present invention, preferably, the insect pest is a root-knot nematode.

[0055] In some embodiments of the present invention, preferably, the application method includes preparing the composition described in the second aspect of the present invention into a fungicide / insecticide for controlling plant fungal and insect pests.

[0056] In some embodiments of the present invention, preferably, the pesticide / insecticide can be applied in the form of its formulation or in a use form prepared therefrom;

[0057] The use form includes at least one of capsule suspension, fine granules, foam, paste, suspension concentrate, emulsion concentrate, soluble concentrate, suspension, wettable powder, soluble powder, powder, granule, water-soluble and / or water-dispersible granule and / or tablet.

[0058] In some embodiments of the present invention, preferably, the preparation of the present invention comprises at least one of a fungicide, an insecticide, a herbicide, a plant growth regulator, an attractant, a miticide, a nematicide, a fertilizer and a safener. The preparation can achieve the effect of being prepared with a liquid fertilizer or a solid or granular fertilizer carrier or mixed with fine sand or soil.

[0059] In some embodiments of the present invention, preferably, the plant comprises at least one of: cereals, beets, pome fruits, stone fruits, soft fruits, legumes, oil crops, melons, fiber plants, citrus fruits, vegetables, laurel plants and plant propagation materials, more preferably wheat, barley, rye, oats, rice, corn, sorghum, related species, sugar radish, fodder beet, apple, pear, plum, peach, almond, cherry, strawberry, raspberry, blackberry, lentil, bean, pea, radish. beans, rapeseed, mustard, olives, sunflowers, coconuts, castor oil plants, cocoa beans, peanuts, pumpkins, cucumbers, melons, cotton, flax, hemp, jute, oranges, lemons, grapefruits, citrus, spinach, lettuce, asparagus, kale, carrots, onions, tomatoes, potatoes, red peppers, avocados, cinnamon, camphor, tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, grapevines, hops, bananas, natural rubber plants, turf, ornamentals, flowers, shrubs, hardwood trees, evergreen trees.

[0060] The composition of the present invention is simple to use, and the composition of the present invention is applied to the pest or its growth medium. The application dosage of the composition of the present invention varies according to weather conditions, dosage form, application timing, application method, application area, target pests and diseases, target crops, etc.

[0061] The present invention will be described in detail below through examples. In the following examples, all parameters were measured by Agilent high performance liquid chromatography analysis method; and the raw materials were purchased from Beijing Coupling Technology Co., Ltd.

[0062] Preparation Example 1

[0063]

[0064] Synthesis of compound 6-1

[0065] In a 250 mL reaction bottle equipped with a stirrer, reflux condenser and thermometer, 2,4-dichloro-5-trifluoromethylpyridine (21.6 g, 0.1 mol), 100 mL DMF and potassium carbonate (20.8 g, 0.15 mol) were added to form a reaction system, the reaction system was heated to 100 ° C and methyl cyanoacetate (11.9 g, 0.12 mol) was added dropwise, and the addition was completed after 0.5 h. After maintaining the reaction at 100 ° C for 4 h, the mixture was filtered, the filter cake was washed with 50 mL DCM, and the filtrate was directly used in the next step reaction.

[0066] Synthesis of compound 5-1

[0067] In a 500mL reaction flask equipped with a stirrer, reflux condenser and thermometer, add the filtrate from the previous step, slowly drop hydrochloric acid containing 0.4mol HCl (a large amount of yellow solid precipitates during the dropwise addition, and 100mL DMF needs to be added), heat to 110°C and react for 4h, then cool the reaction solution to room temperature and add 500mL of water and 100mL of ethyl acetate, stir for 20min, let stand and separate, add 50mL of ethyl acetate to the aqueous phase and separate again, remove the organic phase, and obtain 19.6g of compound 5-1 with a yield of 89%.

[0068] Synthesis of compound 4-1

[0069] In a 250mL reaction bottle equipped with a stirrer, reflux condenser and thermometer, 19.6g of compound 5-1 and 100mL of DMF were added. After cooling to 0°C, sodium hydride (12g, 0.3mol) was added in batches. The addition was completed in 0.5h, and the temperature was raised to room temperature. 1,2-dibromoethane (56.5g, 0.3mol) was added dropwise to the reaction solution over 0.5h. After the addition was completed, the reaction was carried out at 25 degrees for 4h, and the reaction was stopped. 10g of methanol was added to quench, 200mL of water and 50ml of ethyl acetate were added, and the mixture was stirred for 20min. The mixture was allowed to stand and the layers were separated. 50mL of ethyl acetate was added to the aqueous phase and the layers were separated again. The organic phase was combined and washed once with 100mL of water. The organic phase was desolvated to obtain 23g. 9g of yellow-green compound 4-1 was obtained by column chromatography with a yield of 41% (eluent petroleum ether to ethyl acetate 20:1).

[0070] Synthesis of compound 2-1

[0071] Add 7.38g of compound 4-1, 40g of ethanol, 0.7g of Raney nickel and 30kg of hydrogen to a 250mL hydrogenation kettle, react at 30°C for 6h, filter, rinse the filter cake with 10g of ethanol, and spin-dry the filtrate to obtain 6.9g of compound 2-1.

[0072] Preparation Example 2

[0073]

[0074] Synthesis of compound 4-2

[0075] In a 250mL reaction bottle equipped with a stirrer, reflux condenser and thermometer, 11g of compound 5-2 and 100mL of DMF were added. After cooling to 0°C, sodium hydride (6g, 0.15mol) was added in batches. The addition was completed in 0.5h, and the mixture was warmed to room temperature. 2,2-dibromodiethyl ether (34g, 0.15mol) was added dropwise to the reaction solution over 0.5h. After the addition was completed, the mixture was reacted at 25°C for 4h. The reaction was stopped, 5g of methanol was added to quench, 200mL of water and 50mL of ethyl acetate were added, and the mixture was stirred for 20min. The mixture was allowed to stand and the layers were separated. 50mL of ethyl acetate was added to the aqueous phase and the layers were separated again. The organic phase was combined and washed once with 100mL of water. The organic phase was desolvated to obtain 16g. 11g of white compound 4-2 was obtained by column chromatography with a yield of 75% (eluent: petroleum ether: ethyl acetate 20:1).

[0076] Synthesis of compound 2-2

[0077] Add 5.8 g of compound 4-2, 40 g of ethanol, 0.7 g of Raney nickel, and 30 kg of hydrogen to a 250 mL hydrogenation kettle, react at 30 ° C for 6 h, filter, rinse the filter cake with 10 g of ethanol, and spin-dry the filtrate to obtain 6 g of compound 2-2.

[0078] Preparation Example 3

[0079]

[0080] Synthesis of compound 6-3

[0081] In a 250mL reaction bottle equipped with a stirrer, reflux condenser and thermometer, add 2,4-dichloro-5-methylpyridine (compound 9-3, 16.2g, 0.1mol), 100mL DMF, potassium carbonate (20.8g, 0.15mol), heat to 100℃ and start adding methyl cyanoacetate (11.9g, 0.12mol) dropwise. After 0.5h, react at 100℃ for 4h, stop the reaction, filter, wash the filter cake with 50mL DM, and use the filtrate directly in the next reaction.

[0082] In a 500mL reaction flask equipped with a stirrer, reflux condenser and thermometer, add the filtrate from the previous step, slowly add hydrochloric acid containing 0.4mol HCl (a large amount of yellow solid precipitates during the addition, and 100mL DMF needs to be added), heat to 110°C and react for 4h, then cool the reaction solution to room temperature and add 500mL of water and 100mL of ethyl acetate, stir for 20min, let stand and separate, add 50mL of ethyl acetate to the aqueous phase and separate again, desolventize the organic phase to obtain 14.1g of product with a yield of 85%.

[0083] To a 250 ml hydrogenation kettle, add 14.1 g of compound 3, 50 g of ethanol, 1.4 g of Raney nickel, and 30 kg of hydrogen. React at 30 °C for 6 h, filter, rinse the filter cake with 10 g of ethanol, and spin-dry the filtrate to obtain 15.3 g of compound 6-3.

[0084] Synthesis of compound 5-3

[0085] In a 250mL reaction bottle equipped with a stirrer, reflux condenser and thermometer, add 15.3g of compound 6-3 and 60mL of THF, and slowly add 15g of NBS in batches at room temperature. Add for 0.5h. React at room temperature for 1h, add 240mL of water and 60mL of EA, stir for 20min, let stand and separate, add 60ml of ethyl acetate to the aqueous phase and separate again, and desolventize the organic phase to obtain 21g of compound 5-3.

[0086] Synthesis of compound 4-3

[0087] In a 250mL reaction bottle equipped with a stirrer, reflux condenser and thermometer, add 21g crude compound 5-3, 100mL DMSO, 3.6g sodium cyanide, react at 100°C for 12h, add 200ml water and 60mL EA, stir for 20min, let stand to separate, add 60mL ethyl acetate to the aqueous phase and separate again, desolventize the organic phase to obtain 18g compound 4-3.

[0088] Synthesis of Compound 2-3

[0089] In a 250mL reaction bottle equipped with a stirrer, reflux condenser and thermometer, add 18g of compound 4-3 and 100mL of DMF. After cooling to 0°C, add 11g of sodium hydride in batches over 0.5h. Heat to room temperature, add 54g of 1,2-dibromoethane dropwise to the reaction solution over 0.5h. After the addition is completed, react at 25°C for 4h, stop the reaction, add 9g of methanol to quench, add 200mL of water and 50mL of ethyl acetate, stir for 20min, let stand and separate, add 50mL of ethyl acetate to the aqueous phase and separate again, combine and use organic phase, wash the organic phase once with 100ml of water, and desolventize the organic phase to obtain 20g of compound 2-3.

[0090] Example 1

[0091]

[0092] Synthesis of compound 1-1

[0093] In the presence of pyridine (first alkaline substance, 3.16 g, 0.04 mol), tetrahydrofuran 40 mL (solvent), HATU (condensing agent, 7.6 g, 0.02 mol) and EDCI (condensing agent, 3.8 g, 0.02 mol), 2-trifluoromethylbenzoic acid (the compound shown in Formula 3, R4 is hydroxyl, 3.8 g, 0.02 mol) and 5 g of compound 2-1 were condensed for 0.5 h, and the reaction temperature was 50°C.

[0094] After removing most of the tetrahydrofuran, add 160 mL of water and 30 mL of ethyl acetate, stir for 20 min, let stand and separate, add 30 mL of ethyl acetate to the aqueous phase and separate again, combine the organic phases, dry and concentrate the organic phases to obtain 8 g, and column chromatography (eluent petroleum ether / ethyl acetate volume ratio 4:1) to obtain 1.2 g of light yellow product compound 1-1.

[0095] 1 H NMR (500MHz, DMSO) δ8.86(d,J=1.1Hz,1H),8.61(t,J=6.2Hz,1H),8.41(d,J=1.9Hz,1H),7.72( m,2H),7.61(t,J=7.7Hz,1H),7.42(d,J=7.5Hz,1H),3.64(d,J=6.3Hz,2H),1.14-0.96(m,4H).

[0096] Example 2

[0097]

[0098] Compound 1-2

[0099] In the presence of pyridine (first alkaline substance, 3.16 g, 0.04 mol), tetrahydrofuran 40 mL (solvent), HATU (condensing agent, 7.6 g, 0.02 mol) and EDCI (condensing agent, 3.8 g, 0.02 mol), 2-trifluoromethylbenzoic acid (the compound shown in Formula 3, R4 is hydroxyl, 3.8 g, 0.02 mol) and 5.9 g of compound 2-2 were condensed for 0.5 h, and the reaction temperature was 50°C.

[0100] After removing most of the tetrahydrofuran, add 160 mL of water and 30 mL of ethyl acetate, stir for 20 min, let stand and separate, add 30 mL of ethyl acetate to the aqueous phase and separate again, combine the organic phases, dry and concentrate the organic phases, and perform column chromatography (eluent petroleum ether / ethyl acetate volume ratio 4:1) to obtain 2.4 g of light yellow product compound 1-2. 1H NMR (500MHz, DMSO) δ9.00 (s, 1H), 8.47-8.33 (m, 2H), 7.75 (d, J = 7.8Hz, 1H), 7.71 (t, J = 7.4Hz, 1H), 7.64 (t, J = 7.6Hz, 1H), 7.29(d,J=7.5Hz,1H),4.00(d,J=6.3Hz,2H),3.88-3.79(m,2H),3.55-3.41(m,2H),2.72-2.69(m,2H),2.07-1.95(m,2H).

[0101] Example 3

[0102]

[0103] Synthesis of Compounds 1-3

[0104] In the presence of pyridine (first alkaline substance, 3.16 g, 0.04 mol), tetrahydrofuran 40 mL (solvent), HATU (condensing agent, 35 g) and EDCI (condensing agent, 17.6 g), 2-trifluoromethylbenzoic acid (the compound shown in Formula 3, R4 is hydroxyl, 17.6 g) and 20 g of compound 2-3 were condensed for 0.5 h at a reaction temperature of 50°C.

[0105] After removing tetrahydrofuran, 160 mL of water and 30 mL of ethyl acetate were added, stirred for 20 min, and allowed to stand for stratification. 30 mL of ethyl acetate was added to the aqueous phase and stratified again. The organic phases were combined, dried and concentrated, and column chromatography was performed to obtain 38 g of product compound 1-3. M / Z 393.09

[0106] Biological Example: Nematicide Activity Assay

[0107] 1. Preparation of nematode solution:

[0108] (1) Place the egg mass to be used in the experiment into a beaker filled with pure water, seal the beaker with filter paper, and continue to culture at 25°C for 48 hours.

[0109] (2) Preparation of nematode liquid: After culturing the eggs for 48 h, the egg masses were removed by filtration using filter cloth to obtain second-instar larvae of the same age.

[0110] (3) Insect population base survey: Take 1 mL of the mixed liquid containing root-knot nematodes into a counting plate and count under a dissecting microscope to ensure that the nematode suspension contains ≥100 nematodes per milliliter. If the amount of nymphs is small, centrifugation can be performed at 1000 r / min for 2 minutes, the supernatant is discarded, and centrifugation is repeated. Finally, the nematode liquid is diluted with pure water to ≥100 per milliliter for later use. The killing effects of the embodiment, the reference substance and the blank control (CK) on nematodes in the nematode liquid are shown in Table 1.

[0111] Table 1

[0112]

[0113] The results in Table 1 show that the killing effects of compounds 1-1, 1-2 and 1-3 on root-knot nematodes at the effective ingredient dosage are higher than those of the control, and the killing effects on root-knot nematodes at the effective ingredient dosage of 0.6 mg / L are all above 75%, showing good nematicidal effects.

[0114] Testing for wheat powdery mildew

[0115] 1. Spraying method: spray the prepared compound 1-1, 1-2, 1-3 evenly on the surface of cucumber leaves at a water volume of 60L / mu, and cultivate in a greenhouse at a temperature of 20 to 30 degrees Celsius and a humidity of more than 60%.

[0116] 2. Survey time and methods

[0117] 9d and 11d after application, all leaves of each treatment were investigated and compared with those of the control group. The disease situation of the control group was set as level 0, and the evaluation standard was set as level 9. The higher the level, the better the prevention effect:

[0118] Grade 0: There is no significant difference in the diseased area compared with the control group;

[0119] Grade 1: The diseased area is 1-10% lower than that in the control group;

[0120] Grade 2: The diseased area is 11-20% lower than that in the control group;

[0121] Grade 3: The diseased area is 21-30% lower than that in the control group;

[0122] Grade 4: The diseased area is 31-40% lower than that in the control group;

[0123] Grade 5: The diseased area is 41-60% lower than that in the control group;

[0124] Grade 6: The diseased area is 61-70% lower than that in the control group;

[0125] Grade 7: The diseased area is 71-80% lower than that in the control group;

[0126] Grade 8: The diseased area is 81-90% lower than that in the control group;

[0127] Grade 9: The diseased area is 91-100% lower than that in the control group.

[0128] The test results are shown in Table 2.

[0129] Table 2

[0130]

[0131] Wheat powdery mildew is caused by B. graminis. The test results in Table 2 show that the killing effects of compounds 1-1, 1-2 and 1-3 on B. graminis at the effective ingredient dose are higher than those of the reference substance, acetone and blank control (CK). Among them, the killing effects on B. graminis at the effective ingredient dose of 4 ga.i / mu reached level 6, showing a good bactericidal effect.

[0132] In summary, compared with the reference product, the compounds 1-1, 1-2 and 1-3 prepared by Examples 1-3 of the technical solution of the present application have excellent insecticidal and fungicidal effects at the dosage of the active ingredient.

[0133] The preferred embodiments of the present invention are described in detail above, but the present invention is not limited thereto. Within the technical concept of the present invention, the technical solution of the present invention can be subjected to a variety of simple modifications, including the combination of various technical features in any other suitable manner, and these simple modifications and combinations should also be regarded as the contents disclosed by the present invention and belong to the protection scope of the present invention.

Claims

1. An amide compound and / or its salt, wherein: The compound has a structure shown in formula (1): Wherein, R1 is selected from H, halogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted aryl, or R1 and the carbon atom directly connected thereto are combined to form a 3-8 membered ring structure containing or not containing heteroatoms; R2 and R3 are each independently selected from halogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C3-C8 heterocyclyl, substituted or unsubstituted aryl; X is selected from halogen; Wherein, the substituted substituent is selected from halogen, C1-C8 alkyl, halogenated C1-C8 alkyl, and cyano.

2. The compound and / or its salt according to claim 1, wherein R1 is selected from H, halogen, substituted C1-C8 alkyl, substituted C3-C8 cycloalkyl, substituted aryl, or R1 and the carbon atom directly connected thereto are combined to form a 3-8 membered ring structure containing or not containing heteroatoms; and / or, R2 and R3 are each independently selected from halogen, substituted C1-C8 alkyl, substituted C3-C8 cycloalkyl, substituted C3-C8 heterocyclyl, substituted aryl; and / or, X is selected from halogen; Wherein, the substituted substituent is selected from halogen, halogenated C1-C8 alkyl, and cyano.

3. The compound and / or salt thereof according to claim 1 or 2, wherein R1 is selected from H, halogen, or R1 and the carbon atom directly connected thereto form a 3-8 membered ring structure containing or not containing heteroatoms; and / or, R2 and R3 are each independently selected from halogen, substituted C1-C6 alkyl, substituted C3-C6 cycloalkyl, substituted C3-C8 heterocyclyl, substituted phenyl; and / or, X is fluorine or chlorine; Wherein, the substituted substituent is selected from halogen, halogenated C1-C8 alkyl, and cyano.

4. The compound and / or salt thereof according to any one of claims 1 to 3, wherein R1 is selected from H, or R1 and the carbon atom directly connected thereto are combined to form a 3-8 membered ring structure containing or not containing an oxygen atom.

5. The compound and / or salt thereof according to any one of claims 1 to 4, wherein R2 and R3 are each independently selected from halogen, halogenated C1-C4 alkyl or cyano-substituted C3-C6 cycloalkyl; And / or, X is fluorine.

6. The compound and / or salt thereof according to any one of claims 1 to 5, wherein The compound has a structure shown in formula (1-1):

7. The compound and / or salt thereof according to any one of claims 1 to 6, wherein The compound has a structure shown in formula (1-2):

8. The compound and / or salt thereof according to any one of claims 1 to 7, wherein The compound has a structure shown in formula (1-3):

9. Use of the compound and / or salt thereof according to any one of claims 1 to 8 in preventing and controlling plant fungal and insect pests.

10. The use according to claim 9, wherein: The fungal pest is Blumeria graminearum of the Poaceae family; and / or the insect pest is root-knot nematode.

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