Pyridine diamide derivatives, their preparation methods and applications

Abstract

This invention relates to the field of pesticide technology, and discloses a pyridine diamide derivative, its preparation method, and its application. The derivative has the structure shown in Formula I. Compared with the prior art, this invention provides a novel pyridine diamide derivative with high crop growth-promoting activity, especially significant effects on gramineous crops, and has excellent market application prospects.

Description

Technical Field

[0001] This invention relates to the field of pesticide technology, specifically to a pyridine diamide derivative, its preparation method, and its application. Background Technology

[0002] Plant growth regulators are a class of substances that regulate plant growth and development. Their presence can influence and effectively regulate plant growth and development, improve the relationship between plants and the environment, enhance crop resistance to stress, increase crop yield, and improve the quality of agricultural products. Their applications cover the entire plant life cycle, from cell growth and division to rooting, germination, flowering, fruiting, ripening, and abscission.

[0003] my country began producing and using plant growth regulators in the 1950s. After about 70 years of development, plant growth regulators are widely used in agricultural production and occupy a very important position. Therefore, developing new, more effective, economical, and less toxic plant growth regulators is of great significance.

[0004] CN110698392A and others disclose that diamide compounds have insecticidal, acaricidal, bactericidal, herbicidal, and plant growth-regulating activities.

[0005] In the prior art, there are no reports of pyridine diamide derivatives as shown in this invention and their crop growth-promoting activities. Summary of the Invention

[0006] The purpose of this invention is to overcome the problems existing in the prior art and provide a pyridine diamide derivative, its preparation method, and its application. The pyridine diamide derivative provided by this invention has high crop growth-promoting activity.

[0007] To achieve the above objectives, a first aspect of the present invention provides a pyridine diamide derivative, wherein the derivative has the structure shown in Formula I:

[0008]

[0009] R1 and R2 are each independently selected from H, phenyl, halogen-containing substituted phenyl, C1-C6 alkoxy-substituted phenyl, C1-C6 alkyl-substituted phenyl, trifluoromethyl-substituted phenyl, trifluoromethoxy-substituted phenyl, nitro-substituted phenyl, cyano-substituted phenyl, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, pyridyl, halogen-containing substituted pyridyl, thiophene, or halogen-containing substituted thiophene.

[0010] R3 is selected from trifluoromethyl.

[0011] A second aspect of the present invention provides an intermediate compound, said intermediate compound being intermediate I for preparing the derivative described in the first aspect, wherein the structure of said intermediate compound is as follows:

[0012]

[0013] A third aspect of the present invention provides an intermediate compound, said intermediate compound being intermediate II for preparing the derivative described in the first aspect, wherein the structure of said intermediate compound is as follows:

[0014]

[0015] A fourth aspect of the present invention provides a method for preparing the derivative described in the first aspect, wherein the method includes the following steps:

[0016] S1) In the presence of a catalyst, trifluoromethylnicotinic acid is reacted with thionyl chloride or phosgene in a first solvent to obtain acyl chloride;

[0017] S2) Add L-proline methyl ester or methyl ester derivative hydrochloride to the acyl chloride obtained in step S1) to carry out a second reaction, and then add the first acid-binding agent to obtain intermediate I;

[0018] S3) Intermediate I is hydrolyzed in a second solvent by an alkaline compound to obtain intermediate II;

[0019] S4) The intermediate II is subjected to an amidation reaction in a third solvent and a second acid-binding agent to obtain the pyridine diamide derivative.

[0020] The fifth aspect of this invention provides the application of the pyridine diamide derivatives described in the first aspect or the pyridine diamide derivatives prepared by the preparation method described in the fourth aspect in promoting crop growth.

[0021] The sixth aspect of the present invention provides a pesticide composition, wherein the composition comprises the pyridine diamide derivative described in the first aspect or the pyridine diamide derivative prepared by the preparation method described in the fourth aspect as an active ingredient and an agriculturally acceptable carrier.

[0022] The seventh aspect of the present invention provides a method for promoting crop growth, wherein an effective amount of the composition described in the sixth aspect is applied to the crop.

[0023] The beneficial technical effects achieved by the present invention through the above technical solution are as follows:

[0024] Compared with the prior art, the present invention provides a novel pyridine diamide derivative with high crop growth promoting activity, especially for gramineous crops, and has a very good market application prospect. Attached Figure Description

[0025] Figure 1 The image shows the 1H NMR spectrum of compound 1.

[0026] Figure 2 The 1H NMR spectrum of compound 6;

[0027] Figure 3 This is the 1H NMR spectrum of compound 22. Detailed Implementation

[0028] The endpoints and any values ​​of the ranges disclosed herein 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 the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

[0029] A first aspect of the present invention provides a pyridine diamide derivative, wherein the derivative has the structure shown in Formula I:

[0030]

[0031] R1 and R2 are each independently selected from H, phenyl, halogen-containing substituted phenyl, C1-C6 alkoxy-substituted phenyl, C1-C6 alkyl-substituted phenyl, trifluoromethyl-substituted phenyl, trifluoromethoxy-substituted phenyl, nitro-substituted phenyl, cyano-substituted phenyl, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, pyridyl, halogen-containing substituted pyridyl, thiophene, or halogen-containing substituted thiophene.

[0032] R3 is selected from trifluoromethyl.

[0033] In some embodiments of the present invention, R1 and R2 are each independently selected from H, phenyl, halogen-containing substituted phenyl, C1-C6 alkoxy-substituted phenyl, trifluoromethyl-substituted phenyl, trifluoromethoxy-substituted phenyl or C1-C6 cyanoalkyl.

[0034] R3 is located at the para position of N in the pyridine ring.

[0035] In some embodiments of the present invention, the derivative has the structure shown in Formula I:

[0036]

[0037] Where R1 is H;

[0038] R2 is selected from H, phenyl, halogen-containing substituted phenyl, C1-C6 alkoxy-substituted phenyl, trifluoromethyl-substituted phenyl, trifluoromethoxy-substituted phenyl, or C1-C6 cyanoalkyl.

[0039] In the definitions of general formula compounds given above, the terms used generally represent the following substituents:

[0040] Halogens: refer to fluorine, chlorine, bromine or iodine.

[0041] Alkyl: Straight-chain or branched alkyl, such as methyl, ethyl, n-propyl, isopropyl or different butyl, pentyl or hexyl isomers.

[0042] Halogenated alkyl groups: straight-chain or branched alkyl groups in which hydrogen atoms may be partially or completely replaced by halogens, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, heptafluoroisopropyl, 1,1,2,2,2-pentafluoroethyl, etc.

[0043] Halogenated substituted phenyl groups: 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,4-dichlorophenyl, etc.

[0044] Alkoxy-substituted phenyl groups: 4-methoxyphenyl, 3-ethoxyphenyl, 2-methoxyphenyl, etc.

[0045] Trifluoromethyl substituted phenyl groups: 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, etc.

[0046] Trifluoromethoxysubstituted phenyl groups: 4-trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, etc.

[0047] Nitro-substituted phenyl groups: 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, etc.

[0048] Cyano-substituted phenyl groups: 4-cyanophenyl, 3-cyanophenyl, etc.

[0049] Cyanoalkyl groups: methylene nitrile, methyl isopropyl nitrile, etc.

[0050] Halogenated substituted pyridyl groups: 2-chloro-4-pyridyl, 2-chloro-3-pyridyl, etc.

[0051] Halogenated substituted thiophene groups: 2-chloro-3-thiophene, etc.

[0052] In some embodiments of the present invention, the derivative has any of the following structures:

[0053]

[0054]

[0055]

[0056]

[0057] The pyridine diamide derivatives of this invention and their appearance and melting point are shown in Table 1.

[0058] Table 1

[0059]

[0060]

[0061] The substituents in the pyridine diamide derivatives described in this invention can also be selected from the following:

[0062] R1 is methyl, R2 is 3,5-difluorophenyl, and R3 is para-trifluoromethyl; R1 is H, R2 is 3,5-difluorophenyl, and R3 is ortho-trifluoromethyl.

[0063] In some embodiments of the present invention, the derivative has any of the following structures:

[0064]

[0065]

[0066] In some embodiments of the present invention, the derivative has any of the following structures:

[0067]

[0068] A second aspect of the present invention provides an intermediate compound, said intermediate compound being intermediate I for preparing the derivative described in the first aspect, wherein the structure of said intermediate compound is as follows:

[0069]

[0070] In some embodiments of the present invention, the structure of the intermediate compound is as follows:

[0071]

[0072] A third aspect of the present invention provides an intermediate compound, said intermediate compound being intermediate II for preparing the derivative described in the first aspect, wherein the structure of said intermediate compound is as follows:

[0073]

[0074] In some embodiments of the present invention, the structure of the intermediate compound is as follows:

[0075]

[0076] A fourth aspect of the present invention provides a method for preparing the derivative described in the first aspect, wherein the method includes the following steps:

[0077] S1) In the presence of a catalyst, trifluoromethylnicotinic acid is reacted with thionyl chloride or phosgene in a first solvent to obtain acyl chloride;

[0078] S2) Add L-proline methyl ester or methyl ester derivative hydrochloride to the acyl chloride obtained in step S1) to carry out a second reaction, and then add the first acid-binding agent to obtain intermediate I;

[0079] S3) Intermediate I is hydrolyzed in a second solvent by an alkaline compound to obtain intermediate II;

[0080] S4) The intermediate II is subjected to an amidation reaction in a third solvent and a second acid-binding agent to obtain the pyridine diamide derivative.

[0081] In some embodiments of the present invention, the catalyst is DMF.

[0082] In some embodiments of the present invention, the trifluoromethylnicotinic acid is 4-trifluoromethylnicotinic acid.

[0083] In some embodiments of the present invention, the first solvent and the third solvent are each independently selected from at least one of toluene, xylene, dichloromethane, dichloroethane, methyl tert-butyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, acetone, ethyl acetate and acetonitrile, preferably dichloromethane.

[0084] In some embodiments of the present invention, the second solvent is selected from at least one of methanol, ethanol, tetrahydrofuran and 1,4-dioxane, preferably tetrahydrofuran.

[0085] In some embodiments of the present invention, the first acid-binding agent and the second acid-binding agent are each independently selected from basic compounds; the basic compounds are preferably selected from at least one of potassium carbonate, sodium carbonate, potassium bicarbonate, sodium bicarbonate, triethylamine and pyridine, and are preferably triethylamine.

[0086] In some embodiments of the present invention, the alkaline compound in step S3) is selected from at least one of sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate, preferably sodium hydroxide.

[0087] In some embodiments of the present invention, the thionyl chloride in step S1) is added by dropwise addition; the temperature for adding thionyl chloride is preferably -5 to 30°C, and more preferably 5-10°C.

[0088] In some embodiments of the present invention, the temperature of the first reaction is 5-110°C, preferably 40-60°C.

[0089] In some embodiments of the present invention, the temperature of the second reaction is 0-45°C, preferably 25-30°C.

[0090] In some embodiments of the present invention, the temperature of the hydrolysis reaction is -5 to 40°C, preferably 20-25°C.

[0091] In some embodiments of the present invention, the temperature of the amidation reaction is -5 to 110°C, preferably 15 to 30°C.

[0092] This invention does not impose any particular limitation on the purification method of each step of the product; any purification method well known to those skilled in the art can be used, such as recrystallization or column chromatography. This invention preferably employs column chromatography, and the eluent for column chromatography is preferably an ethyl acetate-petroleum ether system.

[0093] The fifth aspect of this invention provides the application of the pyridine diamide derivatives described in the first aspect or the pyridine diamide derivatives prepared by the preparation method described in the fourth aspect in promoting crop growth.

[0094] In some embodiments of the present invention, the crop is a grass (Poaceae).

[0095] The sixth aspect of the present invention provides a pesticide composition, wherein the composition comprises the pyridine diamide derivative described in the first aspect or the pyridine diamide derivative prepared by the preparation method described in the fourth aspect as an active ingredient and an agriculturally acceptable carrier.

[0096] In the above pesticide composition, the pyridine diamide derivative can be used as the sole active ingredient or in combination with other active ingredients.

[0097] In some embodiments of the present invention, the pyridine diamide derivative in the composition comprises 0.1-90% by weight.

[0098] The seventh aspect of the present invention provides a method for promoting crop growth, wherein an effective amount of the composition described in the sixth aspect is applied to the crop.

[0099] The pesticide composition of the present invention can be applied in the form of a formulation.

[0100] As a first possible example, the formulation is a soluble liquid, aqueous solution, suspension, or microemulsion, and the adjuvants include desired components such as emulsifiers and solvents.

[0101] Optionally, the emulsifier includes any one or more of the following: calcium dodecylbenzenesulfonate, alkylphenol formaldehyde resin polyoxyethylene ether, nonylphenol polyoxyethylene ether, sorbitan stearate, polyoxyethylene sorbitan stearate, nonylphenol polyoxyethylene ether, triphenylethylphenol polyoxypropylene polyoxyethylene block polymer, tristyrylphenol polyoxyethylene ether, nonylphenol polyoxyethylene ether, phenethylphenol polyoxyethylene ether, and special phenethylphenol formaldehyde resin polyoxyethylene ether.

[0102] Optionally, the solvent includes any one or more of methanol, dimethylformamide, N-methylpyrrolidone, cyclohexanone, acetone, and dimethyl sulfoxide.

[0103] In the examples above, aqueous solutions, soluble liquids, suspensions, and microemulsions are aqueous dosage forms of the active pharmaceutical ingredient, which are true solution formulations in which the active ingredient is dispersed in water in a molecular or ionic state.

[0104] As a second possible example, the formulation is a water-dispersible granule, and the adjuvants include dispersants, wetting agents, disintegrants, binders, and fillers.

[0105] Optionally, the dispersant includes any one or more of polycarboxylate, lignin sulfonate, and alkylnaphthalene sulfonate.

[0106] Optionally, the wetting agent includes any one or more of alkyl sulfates, alkyl sulfonates, and naphthalene sulfonates.

[0107] Optionally, the disintegrant includes any one or more of ammonium sulfate, urea, sucrose, and glucose.

[0108] Alternatively, the binder may include any one or more of diatomaceous earth, corn starch, polyvinyl alcohol, and carboxymethyl (ethyl) cellulose.

[0109] Optionally, the filler includes any one or more of diatomaceous earth, kaolin, silica, light calcium carbonate, talc, attapulgite, and clay.

[0110] In the above example, water-dispersible granules, also known as dry suspensions or wettable powders, can quickly disintegrate and disperse once placed in water, forming a granular preparation with a highly suspended solid-liquid dispersion system.

[0111] As a third possible example, the formulation is a wettable powder or a soluble powder, and the adjuvants include dispersants, wetting agents, and fillers.

[0112] Optionally, the dispersant includes any one or more of polycarboxylate, lignin sulfonate, and alkyl naphthalene sulfonate;

[0113] Optionally, the wetting agent includes any one or more of alkyl sulfates, alkyl sulfonates, and naphthalene sulfonates;

[0114] Optionally, the filler includes any one or more of ammonium sulfate, urea, sucrose, glucose, diatomaceous earth, kaolin, silica, light calcium carbonate, talc, attapulgite, and clay.

[0115] In the above examples, wettable powders and soluble powders are formulations made by thoroughly mixing and pulverizing pesticide technicals, fillers and adjuvants in a certain proportion to achieve a certain particle size. Their active ingredients are soluble in water, and their fillers can be dispersed in water in an extremely fine and uniform manner.

[0116] Typically, pesticide formulations are prepared by uniformly mixing the components in a specific ratio. This preparation method is simple, and the resulting formulation exhibits good and stable performance.

[0117] The formulation can be used to increase the chlorophyll content of plants, enhance photosynthesis, increase crop yield, and improve crop quality.

[0118] Example of a soluble liquid formulation: Compound 1 10%, calcium dodecylbenzenesulfonate 5%, alkylphenol formaldehyde resin polyoxyethylene ether 10%, nonylphenol polyoxyethylene ether 10%, polyoxyethylene sorbitan stearate 10%, N-methylpyrrolidone 25%, cyclohexanone 30%.

[0119] Example of a suspension concentrate formulation: Compound 1 10%, tristyrene-phenylphenol polyoxyethylene ether 3%, nonylphenol polyoxyethylene ether 4%, phosphate ester wetting and dispersing agent 3%, magnesium aluminum silicate 1.5%, xanthan gum 0.1%, sodium sulfite 0.3%, ethylene glycol 5%, silicone defoamer 0.3%, water to make up 100%.

[0120] The pyridine diamide derivative was prepared into a solution, and the concentration of each embodiment in the solution was 0.01-0.5 g / L.

[0121] In the above examples, the plant growth regulator solutions prepared using the above concentrations showed better effects on crop growth regulation.

[0122] The present invention will be described in detail below through embodiments.

[0123] Unless otherwise specified in the following examples and comparative examples, all conditions were performed under standard conditions or conditions recommended by the manufacturer. Reagents or instruments used, unless otherwise specified, are all commercially available products.

[0124] Example 1

[0125] This example illustrates the preparation of intermediate I.

[0126]

[0127] Add 230 mL of dichloromethane to a 1000 mL reaction flask and start stirring. Add 38.2 g (0.2 mol) of 4-trifluoromethylnicotinic acid and 1 drop of DMF. Stir at room temperature for 5 min, then slowly add 47.56 g (0.4 mol) of thionyl chloride. Control the temperature at 10 °C in an ice-water bath. After the thionyl chloride is added, raise the temperature to 40 °C and reflux for 12 h. After the reaction is completed, remove the solvent under reduced pressure. The remaining oily substance is 4-trifluoromethylnicotinic acid chloride.

[0128] Fresh dichloromethane (443 mL) was added to the reaction flask containing the above-mentioned oily substance, and the mixture was stirred at room temperature for 5 min to fully dissolve the oil. L-proline methyl ester hydrochloride (33.12 g, 0.2 mol) was added, and triethylamine (48.57 g, 0.48 mol) was added dropwise while maintaining the reaction temperature at 25 °C. After the addition was complete, the reaction was continued at 25 °C for 7 h. After the reaction was completed, 400 mL of water was added, and the pH was adjusted to 2 with hydrochloric acid. The dichloromethane was separated, and the aqueous phase was extracted twice with dichloromethane (200 mL × 2). The organic phases were combined. The combined dichloromethane was washed twice with saturated brine (100 mL × 2), dried overnight with anhydrous sodium sulfate, and after solvent removal, intermediate I (58.3 g, yield 96.4%) was obtained.

[0129] Example 2

[0130] This example illustrates the preparation of intermediate II.

[0131]

[0132] Add intermediate I (30 g, 0.1 mol) and THF (300 mL) to a 1000 mL reaction flask and stir for 5 min to dissolve the solid. Slowly add 10% NaOH solution (44 g) at room temperature and stir for 2 h. After the reaction is completed, add 10% hydrochloric acid solution to adjust the pH to 2, remove solvent under reduced pressure, and after the solvent is removed, add methanol (300 mL) to the system and stir to dissolve. Filter, and dry the filtrate with anhydrous sodium sulfate to obtain intermediate II (28.3 g, yield 98.3%).

[0133] Example 3

[0134] This example illustrates the preparation of compound 1.

[0135]

[0136] Intermediate II (1.44 g, 5 mmol) and dichloromethane (20 mL) were added to a 100 mL reaction flask. Triethylamine (0.57 g, 5.6 mmol) was added with stirring. Ethyl chloroformate (0.61 g, 5.6 mmol) was slowly added dropwise to the system at room temperature, and the reaction was maintained at room temperature for 1 h. Aniline (0.47 g, 5 mmol) was then added, and the reaction was maintained at room temperature for 12 h. After the reaction was completed, water (10 mL) was added to the system, and the pH was adjusted to 2 by adding 10% hydrochloric acid solution. The mixture was separated. The aqueous phase was extracted twice with dichloromethane (20 mL × 2). The organic phases were combined, washed with saturated brine (30 mL), dried over anhydrous sodium sulfate, and dissolved to obtain the crude product. The crude product was separated by column chromatography (ethyl acetate: petroleum ether = 1:10) to give compound 1 (1.78 g, yield 97.8%).

[0137] Compound 1 1 The H NMR data are as follows:

[0138] 1 H NMR (500MHz, CDCl3): δ9.32(s,1H), 8.89-8.90(d,1H), 8.77(s,1H), 7.63-7.64(d,1H), 7.52-7.54(d,2H), 7.27-7.29(d,2H), 7.0 5-7.08(m,1H), 4.98-4.99(m,1H), 3.34-3.38(m,1H), 3.21-3.26(m,1H), 2.60-2.71(m,1H), 2.03-2.20(m,2H), 1.93-1.99(m,1H).

[0139] Example 4

[0140] This example illustrates the preparation of compound 2.

[0141]

[0142] The preparation method of compound 2 is the same as that of compound 1, except that aniline is replaced with 4-trifluoromethoxyaniline.

[0143] Compound 2 1 The H NMR data are as follows:

[0144] 1H NMR (500MHz, CDCl3): δ9.50(s,1H), 8.83-8.84(d,1H), 8.73(s,1H), 7.58-7.59(d,1H), 7.44-7.46(d,2H), 7.00-7.02(d ,2H), 4.88-4.90(m,1H), 3.30-3.33(m,1H), 3.17-3.22(m,1H), 2.50-2.52(m,1H), 2.01-2.12(m,2H), 1.87-1.93(m,1H).

[0145] Example 5

[0146] This example illustrates the preparation of compound 3.

[0147]

[0148] The preparation method of compound 3 is the same as that of compound 1, except that aniline is replaced with 4-trifluoromethylaniline.

[0149] Compound 3 1 The H NMR data are as follows:

[0150] 1 H NMR (500MHz, CDCl3): δ9.77(s,1H), 8.92-8.93(d,1H), 8.85(s,1H), 7.66-7.67(d,1H), 7.55-7.56(d,2H), 7.41-7.42(d ,2H), 4.95-4.97(m,1H), 3.42-3.45(m,1H), 3.27-3.32(m,1H), 2.47-2.57(m,1H), 2.13-2.20(m,2H), 1.93-2.00(m,1H).

[0151] Example 6

[0152] This example illustrates the preparation of compound 4.

[0153]

[0154] Compound 4 was prepared by the same method as compound 1, except that aniline was replaced with 3-trifluoromethoxyaniline.

[0155] Compound 4 1 The H NMR data are as follows:

[0156] 1H NMR (500MHz, CDCl3): δ9.61(s,1H), 8.90-8.92(d,1H), 8.80(s,1H), 7.65-7.66(d,2H), 7.22-7.28(m,2H), 6.89-6.91(d ,1H), 4.96-4.98(m,1H), 3.36-3.40(m,1H), 3.24-3.29(m,1H), 2.61-2.67(m,1H), 2.05-2.19(m,2H), 1.95-2.00(m,1H).

[0157] Example 7

[0158] This example illustrates the preparation of compound 5.

[0159]

[0160] Compound 5 was prepared in the same way as compound 1, except that aniline was replaced with 2-bromo-4-trifluoromethoxyaniline.

[0161] Compound 5 1 The H NMR data are as follows:

[0162] 1 H NMR (500MHz, CDCl3): δ9.19(s,1H), 8.88-8.89(d,1H), 8.78(s,1H), 8.36-8.38(d,1H), 7.63-7.64(d,1H), 7.46(s,1H) ), 7.20-7.22(dd,1H), 5.01-5.04(m,1H), 3.35-3.39(m,1H), 3.21-3.26(m,1H), 2.63-2.67(m,1H), 1.97-2.19(m,3H).

[0163] Example 8

[0164] This example illustrates the preparation of compound 6.

[0165]

[0166] Compound 6 was prepared by the same method as compound 1, except that aniline was replaced with 2-trifluoromethoxy-4-bromoaniline.

[0167] Compound 6 1 The H NMR data are as follows:

[0168] 1H NMR (500MHz, CDCl3): δ9.58(s,1H), 8.88-8.89(d,1H), 8.72(s,1H), 8.33-8.35(d,1H), 7.62-7.63(d,1H), 7.4 1-7.43(m,2H), 5.00-5.02(m,1H), 3.29-3.34(m,1H), 3.19-3.24(m,1H), 2.66-2.70(m,1H), 1.96-2.15(m,3H).

[0169] Example 9

[0170] This example illustrates the preparation of compound 7.

[0171]

[0172] Compound 7 was prepared in the same way as compound 1, except that aniline was replaced with 4-trifluoromethoxy-3-bromoaniline.

[0173] Compound 7 1 The H NMR data are as follows:

[0174] 1 H NMR (500MHz, CDCl3): δ9.76(s,1H), 8.92-8.93(d,1H), 8.86(s,1H), 7.90-7.91(d,1H), 7.66-7.67(d,1H), 7.34-7.36(dd,1H), 7.0 8-7.10(dd,1H), 4.90-4.92(m,1H), 3.44-3.48(m,1H), 3.27-3.32(m,1H), 2.43-2.48(m,1H), 2.14-2.22(m,2H), 1.93-2.00(m,1H).

[0175] Example 10

[0176] This example illustrates the preparation of compound 8.

[0177]

[0178] Compound 8 was prepared in the same way as compound 1, except that aniline was replaced with 4-trifluoromethoxy-3-chloroaniline.

[0179] Compound 8 1 The H NMR data are as follows:

[0180] 1H NMR (500MHz, CDCl3): δ9.75(s,1H), 8.82-8.93(d,1H), 8.85(s,1H), 7.77(s,1H), 7.66-7.67(d,1H), 7.28-7.30(dd,1H), 7.10-7 .12(dd,1H), 4.90-4.92(m,1H), 3.43-3.47(m,1H), 3.27-3.32(m,1H), 2.45-2.50(m,1H), 2.13-2.20(m,2H), 1.93-2.00(m,1H).

[0181] Example 11

[0182] This example illustrates the preparation of compound 9.

[0183]

[0184] Compound 9 was prepared by the same method as compound 1, except that aniline was replaced with 2,3-difluoroaniline.

[0185] Compound 9 1 The H NMR data are as follows:

[0186] 1 H NMR (500MHz, CDCl3): δ9.42(s,1H), 8.89-8.90(d,1H), 8.75(s,1H), 8.03-8.07(t,1H), 7.63-7.64(d,1H), 7.03-7.08(m ,1H), 6.89-6.94(m,1H), 5.00-5.03(m,1H), 3.32-3.37(m,1H), 3.21-3.26(m,1H), 2.65-2.70(m,1H), 1.96-2.17(m,3H).

[0187] Example 12

[0188] This example illustrates the preparation of compound 10.

[0189]

[0190] Compound 10 was prepared in the same way as compound 1, except that aniline was replaced with 2,4-difluoroaniline.

[0191] Compound 10 1 The H NMR data are as follows:

[0192] 1H NMR (500MHz, CDCl3): δ9.26(s,1H), 8.88-8.89(d,1H), 8.75(s,1H), 8.19-8.24(m,1H), 7.62-7.63(d,1H), 6.84-6.89(m ,2H), 4.99-5.01(m,1H), 3.32-3.37(m,1H), 3.21-3.26(m,1H), 2.64-2.68(m,1H), 2.04-2.17(m,2H), 1.95-2.01(m,1H).

[0193] Example 13

[0194] This example illustrates the preparation of compound 11.

[0195]

[0196] Compound 11 was prepared in the same way as compound 1, except that aniline was replaced with 2,5-difluoroaniline.

[0197] Compound 11 1 The H NMR data are as follows:

[0198] 1 H NMR (500MHz, CDCl3): δ9.48(s,1H), 8.88-8.89(d,1H), 8.76(s,1H), 8.13-8.17(m,1H), 7.62-7.63(d,1), 6.99-7.04(m,1H), 6.70 -6.74(m,1H), 5.01-5.03(m,1H), 3.33-3.38(m,1H), 3.21-3.26(m,1H), 2.62-2.68(m,1H), 2.05-2.17(m,2H), 1.95-2.01(m,1H).

[0199] Example 14

[0200] This example illustrates the preparation of compound 12.

[0201]

[0202] Compound 12 was prepared in the same way as compound 1, except that aniline was replaced with 2,6-difluoroaniline.

[0203] Compound 12 1 The H NMR data are as follows:

[0204] 1H NMR (500MHz, CDCl3): δ8.88-8.89(d,1H), 8.75-8.79(d,2H), 7.63-7.64(d,1H), 7.18-7.24(m,1H), 6.93-6 .98(m,2H), 5.06-5.09(m,1H), 3.33-3.38(m,1H), 3.20-3.25(m,1H), 2.69-2.74(m,1H), 1.93-2.18(m,3H).

[0205] Example 15

[0206] This example illustrates the preparation of compound 13.

[0207]

[0208] Compound 13 was prepared by the same method as compound 1, except that aniline was replaced with 3,4-difluoroaniline.

[0209] Compound 13 1 The H NMR data are as follows:

[0210] 1 H NMR (500MHz, CDCl3): δ9.61(s,1H), 8.91-8.92(d,1H), 8.84(s,1H), 7.65-7.66(d,1H), 7.56-7.60(m,1H), 6.92-7.01(m ,2H), 4.89-4.91(m,1H), 3.41-3.46(m,1H), 3.26-3.31(m,1H), 2.46-2.49(m,1H), 2.12-2.21(m,2H), 1.92-1.99(m,1H).

[0211] Example 16

[0212] This example illustrates the preparation of compound 14.

[0213]

[0214] Compound 14 was prepared by the same method as compound 1, except that aniline was replaced with 2,3,4-trifluoroaniline.

[0215] Compound 14 1 The H NMR data are as follows:

[0216] 1H NMR (500MHz, CDCl3): δ9.42(s,1H), 8.89-8.90(d,1H), 8.77(s,1H), 7.93-7.98(m,1H), 7.64-7.65(d,1H), 6.90-6.96(m ,1H), 5.01-5.03(m,1H), 3.34-3.38(m,1H), 3.22-3.27(m,1H), 2.61-2.64(m,1H), 2.07-2.17(m,2H), 1.95-2.01(m,1H).

[0217] Example 17

[0218] This example illustrates the preparation of compound 15.

[0219]

[0220] Compound 15 was prepared in the same way as compound 1, except that aniline was replaced with 2-trifluoromethoxyaniline.

[0221] Compound 15 1 The H NMR data are as follows:

[0222] 1 H NMR (500MHz, CDCl3): δ9.42(s,1H), 8.88-8.89(d,1H), 8.73(s,1H), 8.38-8.40(d,1H), 7.62-7.63(d,1H), 7.27-7.31(m ,2H), 7.11-7.14(t,1H), 5.01-5.03(m,1H), 3.31-3.35(m,1H), 3.19-3.24(m,1H), 2.65-2.70(m,1H), 1.95-2.16(m,3H).

[0223] Example 18

[0224] This example illustrates the preparation of compound 16.

[0225]

[0226] Compound 16 was prepared by the same method as compound 1, except that aniline was replaced with 3-fluoroaniline.

[0227] Compound 16 1 The H NMR data are as follows:

[0228] 1H NMR (500MHz, CDCl3): δ9.54(s,1H), 8.90-8.91(d,1H), 8.81(s,1H), 7.64-7.65(d,1H), 7.49-7.51(d,1H), 7.14-7.19(m,1H), 7.07-7.09(d ,1H), 6.71-6.74(t,1H), 4.94-4.96(m,1H), 3.37-3.42(m,1H), 3.23- 3.28(m,1H), 2.57-2.60(m,1H), 2.07-2.19(m,2H), 1.93-1.99(m,1H).

[0229] Example 19

[0230] This example illustrates the preparation of compound 17.

[0231]

[0232] Compound 17 was prepared in the same way as compound 1, except that aniline was replaced with 2-fluoro-4-chloroaniline.

[0233] Compound 17 1 The H NMR data are as follows:

[0234] 1 H NMR (500MHz, CDCl3): δ9.39(s,1H), 8.88-8.89(d,1H), 8.76(s,1H), 8.24-8.27(t,1H), 7.62-7.63(d,1H), 7.10-7.13(m ,2H), 5.00-5.02(m,1H), 3.33-3.37(m,1H), 3.21-3.26(m,1H), 2.62-2.66(m,1H), 2.05-2.17(m,2H), 1.95-2.01(m,1H).

[0235] Example 20

[0236] This example illustrates the preparation of compound 18.

[0237]

[0238] Compound 18 was prepared in the same way as compound 1, except that aniline was replaced with 2,4-dichloroaniline.

[0239] Compound 18 1 The H NMR data are as follows:

[0240] 1H NMR (500MHz, CDCl3): δ9.33(s,1H), 8.88-8.89(d,1H), 8.76(s,1H), 8.32-8.34(d,1H), 7.62-7.63(d,1), 7.40(s,1) , 7.24-7.27(d,1H), 5.01-5.03(m,1H), 3.33-3.38(m,1H), 3.20-3.25(m,1H), 2.64-2.68(m,1H), 1.96-2.18(m,3H).

[0241] Example 21

[0242] This example illustrates the preparation of compound 19.

[0243]

[0244] Compound 19 was prepared in the same way as compound 1, except that aniline was replaced with 2,6-dimethylaniline.

[0245] Compound 19 1 The H NMR data are as follows:

[0246] 1 H NMR (500MHz, CDCl3): δ8.88-8.89(d,1H), 8.74(s,1H), 8.18(s,1H), 7.63-7.64(d,1H), 7.07-7.12(m,3H), 4.98-5.00 (m,1H), 3.38-3.42(m,1H), 3.21-3.26(m,1H), 2.60-2.64(m,1H), 2.26(s,6H), 2.13-2.18(m,2H), 1.95-2.00(m,1H).

[0247] Example 22

[0248] This example illustrates the preparation of compound 20.

[0249]

[0250] Compound 20 was prepared by the same method as compound 1, except that aniline was replaced with 4-fluoroaniline.

[0251] Compound 20 1 The H NMR data are as follows:

[0252] 1H NMR (500MHz, CDCl3): δ9.45(s,1H), 8.90-8.91(d,1H), 8.82(s,1H), 7.64-7.65(d,1H), 7.43-7.45(t,2H), 6.88-6.91(t ,2H), 4.92-4.95(m,1H), 3.39-3.44(m,1H), 3.24-3.29(m,1H), 2.51-2.55(m,1H), 2.10-2.19(m,2H), 1.92-1.98(m,1H).

[0253] Example 23

[0254] This example illustrates the preparation of compound 21.

[0255]

[0256] Compound 21 was prepared by the same method as compound 1, except that aniline was replaced with 3,5-difluorobenzene.

[0257] Compound 21 1 The H NMR data are as follows:

[0258] 1 H NMR (500MHz, CDCl3): δ9.71(s,1H), 8.92-8.93(d,1H), 8.84(s,1H), 7.65-7.66(d,1H), 7.07-7.09(m,2H), 6.43-6.46(t ,1H), 4.89-4.91(m,1H), 3.41-3.45(m,1H), 3.25-3.30(m,1H), 2.46-2.52(m,1H), 2.11-2.21(m,2H), 1.92-1.99(m,1H).

[0259] Example 24

[0260] This example illustrates the preparation of compound 22.

[0261]

[0262] Compound 22 was prepared in the same way as compound 1, except that aniline was replaced with 3,5-dichloroaniline.

[0263] Compound 22 1 The H NMR data are as follows:

[0264] 1H NMR (500MHz, CDCl3): δ9.68(s,1H), 8.92-8.93(d,1H), 8.85(s,1H), 7.66-7.67(d,1H), 7.43(s,2H), 6.99(s,1H), 4.89-4.91(m,1H), 3.41-3.46(m,1H), 3.26-3.31(m,1H), 2.45-2.49(m,1H), 2.11-2.20(m,2H), 1.92-1.99(m,1H).

[0265] Example 25

[0266] This example illustrates the preparation of compound 23.

[0267]

[0268] Compound 23 was prepared by the same method as compound 1, except that aniline was replaced with aminoacetonitrile.

[0269] Compound 23 1 The H NMR data are as follows:

[0270] 1 H NMR (500MHz, CDCl3): δ8.90-8.91(d,1H), 8.75(s,1H), 7.84-7.86(t,1H), 7.64-7.65(d,1H), 4.78-4.80(m,1H), 4 .14-4.25(m,2H), 3.30-3.35(m,1H), 3.19-3.24(m,1H), 2.53-2.57(m,1H), 2.02-2.14(m,2H), 1.92-1.97(m,1H).

[0271] Bioactivity assay:

[0272] Preparation of test reagents: 10% pyridine amide derivative, 5% calcium dodecylbenzenesulfonate, 10% alkylphenol formaldehyde resin polyoxyethylene ether, 10% nonylphenol polyoxyethylene ether, 10% polyoxyethylene sorbitan stearate, 25% N-methylpyrrolidone, and 30% cyclohexanone.

[0273] Test basis: NY / T2061.2—2011 Guidelines for Indoor Bioassay Testing of Pesticides - Plant Growth Regulators Part 2: Foliar Spray Method for Promoting / Inhibiting Plant Growth

[0274] Experimental setup: Each group of experiments consisted of 24 treatments, with 5 plants per treatment and 2 replicates per treatment. The average value was taken.

[0275] Experimental Example 1: Measurement of Chinese Cabbage Growth

[0276] 1. Location of the test site

[0277] Potted plant area in greenhouse No. 1 of Pangjia Base. Chinese cabbage was sown in seedling trays on May 1, 2023.

[0278] 2. Application method

[0279] 2.1 Application timing and method

[0280] The pesticide should be applied starting from the seedling stage of Chinese cabbage, and the application method is foliar spraying.

[0281] 2.2 Application time and frequency

[0282] The drug was administered twice in this experiment. The first administration was on May 18, 2023, and the second administration was on May 25, 2023.

[0283] 3. Application equipment

[0284] 1L glass beaker, 2L electric spray bottle, 1L measuring cylinder, etc.

[0285] 4. Survey methods, timing, and frequency

[0286] 4.1 Survey time and number of times

[0287] A total of four surveys were conducted:

[0288] First survey: May 18, 2023 (before pesticide application); plant height and chlorophyll index were investigated.

[0289] Second survey: May 25, 2023 (7 days after the first application of pesticide, before the second application); plant height and chlorophyll content were surveyed.

[0290] Third survey: June 1, 2023 (7 days after application): plant height and chlorophyll index were investigated.

[0291] Fourth survey: June 6, 2023 (12 days after application): Fresh weight was measured.

[0292] 4.2 Survey Methods

[0293] 4.2.1 Drug Efficacy Survey

[0294] All plants in each treatment were investigated. Chlorophyll content, fresh weight, and plant height of the Chinese cabbage were also investigated.

[0295] 4.2.2 Method for calculating drug efficacy

[0296] Method for calculating the promotion rate / inhibition rate:

[0297] R(%) = (X0 - X1) / X0 × 100%

[0298] In the formula:

[0299] R – Growth promotion rate or inhibition rate;

[0300] X1 — Plant height (or aboveground fresh weight or chlorophyll content) of the treated plant;

[0301] X0 – Control plant height (or aboveground fresh weight or chlorophyll content).

[0302] 4.2.3 Direct impact on crops

[0303] Observe whether the pesticide causes phytotoxicity to the crop. If phytotoxicity occurs, record the type and extent of the damage. In addition, record any beneficial effects on the crop (such as accelerated ripening, increased vigor, etc.).

[0304] Record pesticide damage in the following manner:

[0305] If pesticide damage can be measured or calculated, it should be expressed in absolute values, such as plant height.

[0306] In other cases, the severity and frequency of pesticide damage can be estimated using the following two methods. It is important to accurately describe the pesticide damage symptoms of the crop (stunting, chlorosis, deformity) and provide photos, videos, etc. of the test specimens.

[0307] According to the pesticide damage classification method, the pesticide damage situation of each plot is recorded and represented by -, +, ++, +++, ++++.

[0308] Methods for classifying phytotoxicity:

[0309] - No pesticide damage;

[0310] +: Mild pesticide damage, does not affect normal crop growth;

[0311] ++: Significant pesticide damage, recoverable, and will not cause crop yield reduction;

[0312] +++: Severe pesticide damage, affecting normal crop growth and causing a certain degree of loss in crop yield and quality;

[0313] ++++: Severe pesticide damage, hindering crop growth and resulting in significant losses in crop yield and quality.

[0314] The percentage of phytotoxicity was evaluated by comparing the treated area with the blank control area.

[0315] 5. Survey Results and Analysis

[0316] The raw data was statistically analyzed using Excel. Statistical data are shown in Tables 2-4.

[0317] Table 2. Indoor efficacy test results of each treatment on the regulation of Chinese cabbage growth: plant height promotion rate

[0318]

[0319]

[0320] Table 3. Indoor efficacy test results of each treatment on the regulation of Chinese cabbage growth: chlorophyll growth promotion rate

[0321]

[0322]

[0323] Table 4. Indoor efficacy test results of each treatment on the regulation of Chinese cabbage growth and the rate of fresh weight promotion.

[0324]

[0325] In the regulation experiments of various compounds on Chinese cabbage, a dosage of 0.5 g / L showed a certain promoting effect on plant height, chlorophyll content, and fresh weight relative to water after two applications. Furthermore, no safety issues were observed when using this dosage range on Chinese cabbage.

[0326] Experimental Example 2: Measurement of Maize Growth

[0327] 1. Location of the test site

[0328] In the experimental field planting area of ​​Pangjia Base, corn was sown and mulched on April 15, 2023, using an integrated sowing and mulching machine.

[0329] 2. Application method

[0330] 2.1 Application timing and method

[0331] Apply the pesticide when the corn has 3-5 leaves, using a foliar spray method.

[0332] 2.2 Application time and frequency

[0333] The drug was administered twice in this experiment. The first administration was on May 10, 2023, and the second administration was on May 20, 2023.

[0334] 3. Application equipment

[0335] 1L glass beaker, 2L electric spray bottle, 1L measuring cylinder, etc.

[0336] 4. Survey methods, timing, and frequency

[0337] 4.1 Survey time and number of times

[0338] A total of four surveys were conducted:

[0339] First survey: May 10, 2023 (before pesticide application); plant height and leaf width were surveyed.

[0340] Second survey: May 20, 2023 (10 days after the first application of pesticide, before the second application); plant height and leaf width were surveyed.

[0341] Third survey: June 15, 2023 (26 days after application): plant height and leaf width were surveyed.

[0342] 4.2 Survey Methods

[0343] 4.2.1 Drug Efficacy Survey

[0344] All plants in each treatment were surveyed. The plant height and leaf width of the maize were also investigated.

[0345] 4.2.2 Method for calculating drug efficacy

[0346] Method for calculating the promotion rate / inhibition rate:

[0347] R(%) = (X0 - X1) / X0 × 100%

[0348] In the formula:

[0349] R – Growth promotion rate or inhibition rate;

[0350] X1 — Plant height (or leaf width) of the treated plant;

[0351] X0 – Control plant height (or leaf width).

[0352] 4.2.3 Direct impact on crops

[0353] Observe whether the pesticide causes phytotoxicity to the crop. If phytotoxicity occurs, record the type and extent of the damage. In addition, record any beneficial effects on the crop (such as accelerated ripening, increased vigor, etc.).

[0354] Record pesticide damage in the following manner:

[0355] If pesticide damage can be measured or calculated, it should be expressed in absolute values, such as plant height.

[0356] In other cases, the severity and frequency of pesticide damage can be estimated using the following two methods. It is important to accurately describe the pesticide damage symptoms of the crop (stunting, chlorosis, deformity) and provide photos, videos, etc. of the test specimens.

[0357] According to the pesticide damage classification method, the pesticide damage situation of each plot is recorded and represented by -, +, ++, +++, ++++.

[0358] Methods for classifying phytotoxicity:

[0359] - No pesticide damage;

[0360] +: Mild pesticide damage, does not affect normal crop growth;

[0361] ++: Significant pesticide damage, recoverable, and will not cause crop yield reduction;

[0362] +++: Severe pesticide damage, affecting normal crop growth and causing a certain degree of loss in crop yield and quality;

[0363] ++++: Severe pesticide damage, hindering crop growth and resulting in significant losses in crop yield and quality.

[0364] The percentage of phytotoxicity was evaluated by comparing the treated area with the blank control area.

[0365] Results and Analysis

[0366] The raw data was statistically analyzed using Excel. The statistical data are shown in Tables 5 and 6.

[0367] Table 5. Efficacy of each treatment in regulating maize growth: plant height promotion rate

[0368]

[0369]

[0370] Table 6. Efficacy test of each treatment in regulating maize growth: Leaf width growth promotion rate

[0371]

[0372] In maize regulation experiments using various compounds, a dosage of 0.5 g / L showed that after two applications, plant height and leaf width were both promoted relative to water. Furthermore, no safety issues were observed when used on maize within this dosage range.

[0373] The above examples demonstrate that the use of the pyridine diamide derivatives provided by this invention can regulate and control plant growth and development, increase crop yield, improve the quality of agricultural products, and enable the expression of crop agronomic traits to develop in the direction required by people, which is in line with the development direction of the green, efficient, and low-pollution pesticide industry.

[0374] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. A pyridinebisamide derivative, characterized in that, The derivative has the structure shown in Formula ⅠI: Where R1 is H; R2 is selected from phenyl, halogen-substituted phenyl, C1-C6 alkoxy-substituted phenyl, C1-C6 alkyl-substituted phenyl, trifluoromethyl-substituted phenyl, trifluoromethoxy-substituted phenyl, or C1-C6 cyanoalkyl.

2. The derivative according to claim 1, wherein, The derivative has any of the following structures:

3. The derivative according to claim 2, wherein, The derivative has any of the following structures:

4. The derivative according to claim 2, wherein, The derivative has any of the following structures:

5. An intermediate compound, said intermediate compound being intermediate I for preparing the derivative according to any one of claims 1-4, characterized in that, The structure of the intermediate compound is as follows:

6. An intermediate compound, said intermediate compound being intermediate II for preparing the derivative according to any one of claims 1-4, characterized in that, The structure of the intermediate compound is as follows:

7. A method for preparing a derivative according to any one of claims 1-4, characterized in that, The method includes the following steps: S1) In the presence of a catalyst, trifluoromethylnicotinic acid is reacted with thionyl chloride or phosgene in a first solvent to obtain acyl chloride; S2) Add L-proline methyl ester or methyl ester derivative hydrochloride to the acyl chloride obtained in step S1) to carry out a second reaction, and then add the first acid-binding agent to obtain intermediate I; S3) Intermediate I is hydrolyzed in a second solvent by an alkaline compound to obtain intermediate II; S4) The intermediate II is subjected to an amidation reaction in a third solvent and a second acid-binding agent to obtain the pyridine diamide derivative; The structure of intermediate I is as follows: The structure of intermediate II is as follows:

8. The preparation method according to claim 7, wherein, The catalyst is DMF; And / or, the trifluoromethylnicotinic acid is 4-trifluoromethylnicotinic acid; And / or, the first solvent and the third solvent are each independently selected from at least one of toluene, xylene, dichloromethane, dichloroethane, methyl tert-butyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, acetone, ethyl acetate and acetonitrile; And / or, the second solvent is selected from at least one of methanol, ethanol, tetrahydrofuran and 1,4-dioxane; And / or, the first acid-binding agent and the second acid-binding agent are each independently selected from basic compounds; And / or, the alkaline compound in step S3) is selected from at least one of sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate; And / or, in step S1), the thionyl chloride is added by dropping; And / or, the temperature of the first reaction is 5-110°C; And / or, the temperature of the second reaction is 0-45°C; And / or, the hydrolysis reaction is carried out at a temperature of -5 to 40°C; And / or, the temperature of the amidation reaction is from -5 to 110°C.

9. The preparation method according to claim 8, wherein, The first and third solvents are dichloromethane; And / or, the second solvent is tetrahydrofuran; And / or, the basic compound used as the first and second acid-binding agent is selected from at least one of potassium carbonate, sodium carbonate, potassium bicarbonate, sodium bicarbonate, triethylamine, and pyridine; And / or, the alkaline compound mentioned in step S3) is sodium hydroxide; And / or, the temperature for adding thionyl chloride is -5 to 30°C; And / or, the temperature of the first reaction is 40-60°C; And / or, the temperature of the second reaction is 25-30°C; And / or, the hydrolysis reaction is carried out at a temperature of 20-25°C; And / or, the temperature of the amidation reaction is 15-30°C.

10. The preparation method according to claim 9, wherein, The basic compound used as both the first and second acid-binding agents is triethylamine; And / or, the temperature for adding thionyl chloride is 5-10℃.

11. The use of the pyridine diamide derivative according to any one of claims 1-4 or the pyridine diamide derivative prepared by the preparation method according to any one of claims 7-10 in promoting crop growth.

12. The application according to claim 11, wherein, The crop in question is a grass belonging to the Poaceae family.

13. A pesticide composition, characterized in that, The composition comprises, as an active ingredient and an agriculturally acceptable carrier, a pyridine diamide derivative of any one of claims 1-4 or a pyridine diamide derivative prepared by any one of claims 7-10.

14. The pesticide composition according to claim 13, wherein, The pyridine diamide derivative in the composition has a weight percentage of 0.1-90%.

15. A method for promoting crop growth, characterized in that, Apply an effective amount of the composition of claim 13 or 14 to the crop.

16. The method according to claim 15, wherein, The crop in question is a grass belonging to the Poaceae family.

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