CN-121974852-A - N-phenylpyrazole derivative and preparation method and application thereof

CN121974852ACN 121974852 ACN121974852 ACN 121974852ACN-121974852-A

Abstract

The invention relates to the technical field of compound synthesis technology and pesticides, in particular to an N-phenylpyrazole derivative, a preparation method and application thereof, wherein the N-phenylpyrazole derivative has a 100% prevention and removal effect on broadleaf weeds at a dosage of 37.5-150 g a.i./ha, partial compounds have good prevention and removal effects on grassy weeds, the compounds can obtain good weeding effects at low dosage, and the compounds can be used as potential PPO inhibitors and developed and used as broadleaf weed post-emergence herbicides.

Inventors

GAN XIUHAI
ZHANG JIAHUI
ZHANG WEI
TANG XIANYING

Assignees

贵州大学

Dates

Publication Date: 20260505
Application Date: 20260126

Claims (7)

1. The N-phenylpyrazole derivative is characterized by having a structural general formula as shown in formula (I): in formula (I): x is independently selected from H, CH 2 、CH 3 ; y is independently selected from O, S, NR 7 、 ONCR 8 ; r 1 、R 2 is independently selected from CH 3 、CF 3 、Ph、4-CH 3 -Ph; R 3 、R 4 is independently selected from hydrogen, halogen, -CN, C 1 -C 6 alkyl, (C 1 -C 6 haloalkyl) -O-, or (C 1 -C 6 alkyl) -SO 2 -; R 5 is independently selected from hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy; R 6 is independently selected from hydrogen, halogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 cyano, C 3 -C 6 cycloalkyl, C 5 -C 6 aryl, C 2 -C 6 heterocyclyl, R 9 -O-R 10 、(CH 2 ) n COX 2 R 11 ; n is selected from 0,1, 2, 3,4,5, 6; x 2 is independently selected from O, S, NR 12 、NCR 13 ; r 7 、R 8 is independently selected from hydrogen, halogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy; r 9 、R 10 、R 11 is independently selected from hydrogen, halogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy; R 12 、R 13 is each independently selected from H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 1 -C 4 alkoxyC 1 -C 6 -alkyl, C 1 -C 4 haloalkoxy C 1 -C 6 alkyl.
2. The N-phenylpyrazole derivative according to claim 1, comprising the following compounds: compound A1 (E) -methyl 2- (((2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) benzylidene) amino) oxy) propanoate; compound A2 (E) -ethyl 2- (((2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) benzylidene) amino) oxy) propionate; compound A3 (E) -propyl 2- (((2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) benzylidene) amino) oxy) propionate; Compound A4 (E) -2- (((2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) benzylidene) amino) oxy) propanoic acid butyl ester; Compound A5 (E) -2- (((2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) benzylidene) amino) oxy) pentanoic acid pentyl ester; Compound A6 (E) -methyl 2- (((2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) benzylidene) amino) oxy) acetate; compound A7 (E) -ethyl 2- (((2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) benzylidene) amino) oxy) acetate; compound A8 (E) -propyl 2- (((2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) benzylidene) amino) oxy) acetate; Compound A9 (E) -2- (((2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) benzylidene) amino) oxy) butyl acetate; Compound a10, 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid methyl ester; 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid ethyl ester; 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid isopropyl ester; 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid tert-butyl ester; compound a14, 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid propyl ester; 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid allyl ester; 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid sec-butyl ester; 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid butyl ester; compound a18, 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid 2-methoxyethyl ester; 2, 3-tetrafluoropropyl 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylate; compound a20, 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid cyclohexyl ester; compound a21, phenyl 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylate; Compound a22, 3- (2, 4-difluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid methyl ester; 3- (2, 4-difluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid ethyl ester; Compound a24, 3- (2, 4-difluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid propyl ester; compound a25, allyl 3- (2, 4-difluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylate; compound a26, 3- (4-chloro-2-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid methyl ester; Compound a27, 3- (4-chloro-2-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid ethyl ester; 3- (4-chloro-2-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid propyl ester; Compound a29, allyl 3- (4-chloro-2-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylate; Compound a30, 3- (2, 4-dichloro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid methyl ester; 3- (2, 4-dichloro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid ethyl ester; 3- (2, 4-dichloro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid propyl ester; 3- (2, 4-dichloro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid allyl ester; Compound a34, 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-thiocarboxylic acid methyl ester; compound a35, 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-thiocarboxylic acid ethyl ester; 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-thiocarboxylic acid propyl ester; Compound a37, 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -N, 5-dimethyl-4, 5-dihydroisoxazole-5-carboxamide; Compound a38, 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -N, 5-trimethyl-4, 5-dihydroisoxazole-5-carboxamide; Compound a39 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -N-ethyl-5-methyl-4, 5-dihydroisoxazole-5-carboxamide; compound a40, 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -N-isopropyl-5-methyl-4, 5-dihydroisoxazole-5-carboxamide; Compound a41, 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-N-propyl-4, 5-dihydroisoxazole-5-carboxamide; Compound a42, N-butyl-3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxamide; Compound a43, 2-methoxy-2-oxoethyl 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylate; compound a44, 2-ethoxy-2-oxoethyl 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylate; 2-oxo-2-propoxyethyl 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylate; compound a46, 1-methoxy-1-oxopropan-2-yl 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylate; compound a47, 1-ethoxy-1-oxoprop-2-yl 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylate; Compound a48, 1-oxo-1-propoxyprop-2-yl 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylate; Compound a49 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid alkylene oxide-2-ylmethyl ester; Compound A50-methyl 3- (2-chloro-4-fluoro-5- (5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl) phenyl) -5-methyl-4, 5-dihydroisoxazole-5-carboxylic acid (tetrahydrofuran-2-yl) ester.
3. Process for the preparation of an N-phenylpyrazole derivative according to any of claims 1 to 2, comprising the steps of: (1) Preparation of intermediate 2: Dissolving the intermediate 1 in 98% concentrated sulfuric acid to form a solution, placing the solution in an ice bath for cooling, then dropwise adding 65% concentrated nitric acid, stirring the reaction mixture for 30 minutes under ice bath conditions, pouring the reaction mixture into ice, vigorously stirring for 30 minutes, collecting a precipitate by filtration, washing with water, and then drying in vacuo to obtain an intermediate 2; (2) Preparation of intermediate 3: Mixing intermediate 2, ammonium chloride and 90% ethanol solution, stirring, heating to 80 ℃, slowly adding iron powder, reacting the reaction system at 80 ℃ for 4 hours, filtering the hot reaction mixture through a diatomite pad, and sequentially extracting, drying and carrying out column chromatography to obtain intermediate 3; (3) Preparation of intermediate 4: dissolving the intermediate 3 in 80% ethanol, adding hydroxylamine hydrochloride, heating to 80 ℃ for reaction for 4 hours, extracting, merging organic phases, drying, concentrating and purifying by column chromatography after the reaction is finished, thus obtaining an intermediate 4; (4) Preparation of intermediate 5: Intermediate 4 was dissolved in DMF, 1-trifluoro-2, 4-pentanedione and O- (diphenylphosphino) hydroxylamine were added, heated to 85 ℃, and after completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The combined organic phases were dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the residue was purified by column chromatography to give intermediate 5; (5) Preparation of the target Compounds A1-A9: Dissolving the intermediate 5 in DMF, adding potassium carbonate and substituted 2-chlorocarboxylic acid derivatives, stirring at room temperature, and sequentially extracting, separating an organic layer, drying, concentrating under reduced pressure and performing column chromatography after the reaction is finished to obtain N-phenylpyrazole derivatives A1-A9; (6) Preparation of the target Compounds A10-A50: Intermediate 5 was dissolved in DMF, heated to 35 ℃, N-chlorosuccinimide was added to the solution with stirring, after continuing stirring for 1 hour, the reaction solution was cooled to room temperature, followed by extraction with dichloromethane, the organic phase was washed twice with 1mol/L hydrochloric acid and saturated brine each, dried over anhydrous sodium sulfate and filtered, the filtrate was cooled to 0-5 ℃, and the substituted enoate derivative and triethylamine were slowly added dropwise thereto. After the reaction is finished, the N-phenylpyrazole derivative A10-A50 is obtained after the organic layer is extracted, separated, dried and subjected to column chromatography in sequence.
4. A process for the preparation of an N-phenylpyrazole derivative according to claim 3, wherein the substituted intermediate 1 is 2-chloro-4-fluorobenzaldehyde, 2, 4-difluorobenzaldehyde, 2, 4-dichlorobenzaldehyde, 4-chloro-2-fluorobenzaldehyde.
5. A process for the preparation of an N-phenylpyrazole derivative according to claim 3, wherein the substituted 2-chlorocarboxylic acid derivative is selected from the group consisting of methyl 2-chloroacetate, ethyl 2-chloroacetate, propyl 2-chloroacetate, butyl 2-chloroacetate, amyl 2-chloroacetate, benzyl 2-chloroacetate, methyl 2-chloropropionate, ethyl 2-chloropropionate, propyl 2-chloropropionate, butyl 2-chloropropionate, pentyl 2-chloropropionate, tert-butyl 2-chloropropionate, 2-methoxy-2-oxoethyl 2-chloropropionate, 1-methoxy-1-oxopropan-2-yl 2-chloropropionate, 3-methoxy-3-oxopropyl 2- ((2-chloropropionyl) thio) ethyl acetate, ethyl 2- ((2-chloropropionyl) thio) propionate, methyl 3- (2-chloropropionamide) propionate, methyl 2-chloro-2-methylpropionate, methyl 2-chlorobutanoate, ethyl 2-chlorobutanoate, methyl 2-chlorobutanoate; the substituted olefine acid derivative is methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, tert-butyl methacrylate, propyl methacrylate, allyl methacrylate, sec-butyl methacrylate, methoxyethyl methacrylate, 2, 3-tetrafluoropropyl methacrylate, cyclohexyl methacrylate, phenyl methacrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, N-methyl methacrylamide, N-dimethyl methacrylamide, N-ethyl methacrylamide, N-isopropyl methacrylamide, N-propyl methacrylamide, 2-methoxy-2-oxyethyl methacrylate, 2-ethoxy-2-oxyethyl methacrylate, 2-propoxy-2-oxyethyl methacrylate, 1-methoxy-1-oxoprop-2-yl methacrylate, 1-ethoxy-1-oxoprop-2-yl methacrylate, glycidyl methacrylate, 2-epoxypentyl methacrylate.
6. Use of an N-phenylpyrazole derivative according to claim 1 or 2 for the preparation of a herbicidal agent, a weed growth enzyme inhibitor.
7. The use of N-phenylpyrazole according to claim 6 for the preparation of a herbicide or weed growth enzyme inhibitor, wherein the weeds are barnyard grass, green bristlegrass, goosefoot, purslane, amaranth, abutilon, calabash, amaranth, milk vetch, black broom corn millet, ryegrass, schizonepeta macrophylla, oat, vetch seed, marigold, morning glory, zinnia, alfalfa, arrow pea, cassia seed, chicory, silybum marianum, licorice, field phthalocyanine, jersey, suaeda salsa, broom cypress, gray, dandelion.

Description

N-phenylpyrazole derivative and preparation method and application thereof Technical Field The invention belongs to the field of compound pesticides, and particularly relates to an N-phenylpyrazole derivative, a preparation method and application thereof. Background Herbicides play a critical role in modern agriculture, which can effectively control weeds and increase crop yield. The development and application of herbicides has changed tremendously over the last several decades due to the need to address the challenges that continue to arise, such as weed resistance, environmental friendliness issues, and the need for sustainable agriculture. The development of efficient, green herbicides is therefore a great need in current agricultural production. Protoporphyrinogen Oxidase (PPO) catalyzes the oxidation of protoporphyrinogen IX to protoporphyrin IX, one of the most important targets found by herbicides. Protoporphyrinogen oxidase is the penultimate enzyme of chlorophyll and heme biosynthesis, belonging to the large family of enzymes containing the Flavonoid Adenine Dinucleotide (FAD), catalyzing the conversion of protoporphyrinogen IX to protoporphyrin IX, and plant inhibition of PPO can lead to toxic accumulation of protoporphyrin IX in the cytoplasm. Under light, protoporphyrin IX reacts with oxygen to produce a number of reactive oxygen species, which destroy cell membranes and cause rapid burn symptoms in plants. On the other hand, the PPO inhibitor has the advantages of broad herbicide controlling spectrum, strong drug resistance, environmental protection, low toxicity, low use ratio and the like. The small molecules containing pyrazole rings are widely applied to the fields of medicines, pesticides, materials and the like, and herbicides such as pyriproxyfen, pyraclonil and the like which are developed based on pyrazole and are marketed in the pesticide field. In addition, in recent years, researches on herbicides containing pyrazoles have been advanced, for example, application numbers WO9602515A1, CN1151159A, WO0116112A1, CN1402979A, CN107518008A and US20190069512A1 disclose the preparation and herbicidal activity of the pyrazoles herbicides. The compounds have the characteristics of high efficiency, broad spectrum, low residue and the like, are particularly effective on broadleaf weeds, but meanwhile, the compounds have serious damage to broadleaf crops, the safety aspect still needs to be improved, and the problems of high production cost, lower overall yield and the like exist. The N-phenylpyrazole is a PPO inhibitor structure with a newer framework, has a new action mechanism, and the design of the synthetic herbicide small molecule based on the N-phenylpyrazole unit is quite in line with the current trend of new pesticide creation. Most of the existing herbicides have high herbicidal activity on weeds and also have strong damage on crops, so that the herbicides cannot be applied to the growing process of the crops. However, with the occurrence of problems such as environmental pollution and weed resistance, and in actual production, crop growth has high demands for weed control. Therefore, development of novel, efficient, low-toxicity, environmentally friendly green herbicides is urgent. Disclosure of Invention Aiming at the defects of the prior art, the invention provides an N-phenylpyrazole derivative, and a preparation method and application thereof. In order to achieve the above purpose, the technical scheme adopted by the invention is as follows: The invention aims to provide an N-phenylpyrazole derivative, which has a structural general formula shown in a formula (I): in formula (I): x is independently selected from H, CH 2、CH3; y is independently selected from O, S, NR 7、 ONCR8; r 1、R2 is independently selected from CH 3、CF3、Ph、4-CH3 -Ph; R 3、R4 is independently selected from hydrogen, halogen, -CN, C 1-C6 alkyl, (C 1-C6 haloalkyl) -O-, or (C 1-C6 alkyl) -SO 2 -; R 5 is independently selected from hydrogen, halogen, C 1-C6 alkyl, C 1-C6 haloalkyl, C 1-C6 alkoxy; R 6 is independently selected from hydrogen, halogen, C 1-C6 alkyl, C 3-C6 alkenyl, C 3-C6 haloalkenyl, C 3-C6 alkynyl, C 1-C6 haloalkyl, C 1-C6 alkoxy, C 1-C6 cyano, C 3-C6 cycloalkyl, C 5-C6 aryl, C 2-C6 heterocyclyl, R 9-O-R10、(CH2)nCOX2R11; n is selected from 0,1, 2, 3,4,5, 6; x 2 is independently selected from O, S, NR 12、NCR13; r 7、R8 is independently selected from hydrogen, halogen, C 1-C6 alkyl, C 3-C6 alkenyl, C 3-C6 haloalkenyl, C 3-C6 alkynyl, C 1-C6 haloalkyl, C 1-C6 alkoxy; r 9、R10、R11 is independently selected from hydrogen, halogen, C 1-C6 alkyl, C 3-C6 alkenyl, C 3-C6 haloalkenyl, C 3-C6 alkynyl, C 1-C6 haloalkyl, C 1-C6 alkoxy; R 12、R13 is each independently selected from H, C 1-C6 alkyl, C 1-C6 haloalkyl, C 3-C6 alkenyl, C 3-C6 haloalkenyl, C 3-C6 alkynyl, C 1-C4 alkoxyC 1-C6 -alkyl, C 1-C4 haloalkoxy C 1-C6 alkyl. The N-phenylpyrazole derivative comprises compounds A1 to A50. The second object of the present