CN114716408A - Bisamide derivative containing aromatic amide and preparation method and application thereof - Google Patents
Bisamide derivative containing aromatic amide and preparation method and application thereof Download PDFInfo
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- CN114716408A CN114716408A CN202210293592.5A CN202210293592A CN114716408A CN 114716408 A CN114716408 A CN 114716408A CN 202210293592 A CN202210293592 A CN 202210293592A CN 114716408 A CN114716408 A CN 114716408A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
The invention relates to bisamide derivatives containing aromatic amide and having insecticidal activity, as shown in a general formula (I), and preparation and application thereof, wherein the definition of a substituent group is defined in the specification. On the basis of the structure of the prior bisamide insecticide, different substituted benzene rings are introduced into the position of fatty amide, so that the drug resistance of the prior compound is improved, the insecticidal activity is improved, and the bisamide insecticide is very effective on lepidoptera pests such as oriental armyworm, spodoptera exigua, diamond back moth and the likeIs an insecticide with wide application prospect.
Description
Technical Field
The invention relates to a synthesis technology of an agricultural chemical insecticide, in particular to a bisamide derivative containing aromatic amide and a preparation method and application thereof.
Background
With the needs of living environment for human beings to live and the increase of the drug resistance of insects to the existing insecticides, the development of novel insecticides with high efficiency, low toxicity, low cost and unique action mechanism is urgently needed.
The o-formamidobenzamide compounds are effective pesticides for preventing and controlling lepidoptera pests which are developed in recent years. Numerous patents were successively filed by pesticide Japan, DuPont, Bayer agriculture, Germany, and many colleges and scientific research institutions at home, and a large number of compounds were reported.
In order to design and synthesize a new compound with insecticidal bioactivity and improve the drug resistance of the compound, a class of bisamide derivatives containing aromatic amide which is not reported in documents is designed and synthesized, and a bioactivity test shows that the derivatives have higher insecticidal activity.
Disclosure of Invention
The invention aims to provide bisamide derivatives containing aromatic amide, a preparation method and application thereof, wherein the derivatives can improve the drug resistance of the original compounds and can improve the insecticidal activity of the derivatives, and after the derivatives act on insects, the insects have symptoms of anorexia, cachexia, vomiting and defecation and muscle-controlled contraction, and finally death and the like. The derivatives have higher insecticidal activity on lepidoptera pests such as oriental armyworm, plutella xylostella, spodoptera frugiperda and the like, and can be used as insecticides for preventing and controlling agricultural pests.
The bisamide derivative containing aromatic amide provided by the invention has the following general formula (I):
in the formula: r1Is halogen, CF3、CHF2、CF2CF3、CN、NO2、NH2、OCF3、OCH2CF3、SOCF3、SOCHF2、SO2CHF2、C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C3-C6Cycloalkoxy, halo C3-C6Cycloalkoxy, C1-C6Alkylthio, halo C1-C6Alkylthio radical, C2-C6Alkenyl, halo C2-C6Alkenyl radical, C2-C6Alkenyloxy, halogeno C2-C6Alkenyloxy radical, C2-C6Alkynyl, halo C2-C6Alkynyl, C2-C6An alkanoyloxy group;
R2is H, halogen, NO2、CN、CH3SO、CH3SO2、C1-C6Alkyl radical, C1-C6Alkoxy radical, C1-C6Alkylthio radical, C3-C6Cycloalkyl, benzene, halogen-substituted benzene;
R3is H, halogen, NO2、CN、CH3SO、CH3SO2、C1-C6Alkyl radical, C1-C6Alkoxy radical, C1-C6Alkylthio radical, C3-C6Cycloalkyl, benzene, halogen-substituted benzene;
R4、R5、R6、R7、R8is halogen, CN, NO2、CF3、OCF3Heptafluoroisopropyl group, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C1-C6Alkylthio, halo C1-C6Alkylthio group, CH3SO、CH3SO2；
The aromatic amide-containing bisamide derivative I according to claim 1, characterized in that:
halogen is fluorine, chlorine, bromine or iodine; alkyl is straight or branched chain alkyl;
haloalkyl is a straight or branched chain alkyl; the hydrogen atoms on these alkyl groups may be partially or wholly substituted with halogen atoms; "haloalkoxy", "halocycloalkyl", "halocycloalkoxy" and "haloalkenyl" are as defined under the term "haloalkyl";
alkenyl is straight-chain or branched having 2 to 6 carbon atoms and may have a double bond present in any position;
alkynyl is straight-chain or branched having 2 to 6 carbon atoms and may have a triple bond at any position.
The synthesis method of the bisamide derivative containing the aromatic amide comprises the following steps:
the preparation steps are as follows:
step (1): and mixing the compound shown in the general formula II with acyl chloride and an organic solvent, adding a drop of N, N-dimethylformamide, reacting at room temperature for 3 hours, and concentrating under reduced pressure to obtain a compound III.
Step (2): mixing the compound shown in the general formula IV with an organic solvent and alkali, dropwise adding the compound shown in the general formula III at 0 ℃, heating to room temperature, and reacting to obtain the target compound I, wherein the molar ratio of the compound shown in the general formula III to the compound shown in the general formula IV is 1: 1. The groups in the reaction formula are as described above.
The organic solvent is dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane, tetrahydrofuran or 1, 4-dioxane.
The acyl chloride is oxalyl chloride or thionyl chloride.
The base is triethylamine, pyridine, N-dimethylaniline, diisopropylethylamine or N-methylmorpholine.
The invention relates to an application of bisamide derivatives containing aromatic amide, which is characterized in that: the insecticidal composition is used for preparing agricultural insecticides, and is particularly used for controlling lepidoptera insects such as oriental armyworm, plutella xylostella and spodoptera frugiperda; the pesticide composition can also be used as an active ingredient and matched with agriculturally acceptable auxiliaries to be used for controlling insects.
The bisamide derivatives containing aromatic amide can also be used as an active ingredient and matched with an agriculturally acceptable auxiliary agent to form a pesticide composition for controlling insects.
The bisamide derivative containing aromatic amide of the invention can be used for preparing agricultural insecticidal compositions, which contain the bisamide derivative I containing aromatic amide of claim 1 as an active ingredient, wherein the content of the active ingredient is 0.1 to 99.9 percent by weight, 99.9 to 0.1 percent by weight of solid or liquid auxiliary agent, and optionally 0 to 25 percent by weight of surfactant.
The bisamide derivative I containing aromatic amide is compounded with other commercial insecticides to serve as an active ingredient, wherein the mass percentage of the bisamide derivative I containing aromatic amide to the other commercial insecticides is 1 to 99 to 1 percent, the content of the active ingredient is 1 to 99 percent, and the weight of the active ingredient is 99 to 1 percent.
The bisamide derivative I containing the aromatic amide is compounded with other commercial bactericidal and miticidal agents to serve as an active ingredient, the ratio of the bisamide derivative I containing the aromatic amide to the other commercial bactericidal and miticidal agents is 1 to 99 to 1 percent, the content of the active ingredient is 1 to 99 percent, and the solid or liquid auxiliary agent accounts for 99 to 1 percent.
The bisamide derivative I containing aromatic amide is compounded with other commercial plant virus resisting agents to serve as active ingredients, the ratio of the bisamide derivative I containing aromatic amide to the other commercial plant virus resisting agents is 1 to 99 to 1 percent, the content of the active ingredients is 1 to 99 percent, and the solid or liquid auxiliary agent accounts for 99 to 1 percent.
The invention has the technical effects that: not only improves the drug resistance of the original compound, but also improves the insecticidal activity, has simple preparation method, and can be widely used for preparing agricultural insecticides.
Detailed Description
The present invention will be further described with reference to the following examples, which are provided for better understanding of the present invention and the essential features thereof, and therefore, the examples should not be construed as limiting the scope of the present invention.
Example 1
Synthesis of N- (4-chloro-2- ((2, 4-difluorophenyl) carbamoyl) -6-methylphenyl) -1- (3-chloropyridin-2-yl) -3- (2, 2, 2-trifluoroethoxy) -1H-pyrazole-5-carboxamide (derivative 295)
Step A: synthesis of 1- (3-chloropyridin-2-yl) -3- (2, 2, 2-trifluoroethoxy) -1H-pyrazole-5-carbonyl chloride
1- (3-Chloropyridin-2-yl) -3- (2, 2, 2-trifluoroethoxy) -1H-pyrazole-5-carboxylic acid (4.00 g, 12.5 mmol) was dissolved in 60 ml of ultra-dry dichloromethane, oxalyl chloride (1.4 ml, 16.2 mmol) and one drop of N, N-dimethylformamide were added and reacted at room temperature for 3 hours, and the solvent was removed under reduced pressure to obtain the acid chloride, which was used directly in the next reaction.
And B: synthesis of N- (4-chloro-2- ((2, 4-difluorophenyl) carbamoyl) -6-methylphenyl) -1- (3-chloropyridin-2-yl) -3- (2, 2, 2-trifluoroethoxy) -1H-pyrazole-5-carboxamide
The acid chloride prepared above was dissolved in 40 ml of tetrahydrofuran, slowly added dropwise at 0 ℃ to tetrahydrofuran containing 2-amino-5-chloro-N- (2, 4-difluorophenyl) -3-methylbenzamide (3.7 g, 12.5 mmol) and diisopropylethylamine (2.7 ml, 16.2 mmol), transferred to room temperature for 0.5 h and the reaction was complete by TLC. Adding 80 ml of dichloromethane for dilution, washing by using a 1mol/L hydrochloric acid solution, a saturated sodium bicarbonate solution and a saturated sodium chloride solution in sequence, drying an organic phase, desolventizing, recrystallizing by using dichloromethane and normal hexane to obtain N- (4-chloro-2- ((2, 4-difluorophenyl) carbamoyl) -6-methylphenyl) -1- (3-chloropyridin-2-yl) -3- (2, 2, 2-trifluoroethoxy) -1H-pyrazole-5-formamide which is a white solid, has the yield of 50 percent and the melting point of 207 ℃ and 208 ℃.
Example 2
Synthesis of 3-bromo-N- (4-chloro-2- ((2-chloro-4, 6-difluorophenyl) carbamoyl) -6-methylphenyl) -1- (3-chloropyridin-2-yl) -1H-pyrazole-5-carboxamide (derivative 52)
Step A: synthesis of 3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazole-5-carbonyl chloride
3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazole-5-carboxylic acid (4.00 g, 13.3 mmol) was dissolved in 60 ml of ultra-dry dichloromethane, oxalyl chloride (1.5 ml, 17.3 mmol) and one drop of N, N-dimethylformamide were added, reacted at room temperature for 3 hours, and the solvent was removed under reduced pressure to give the acid chloride, which was used directly in the next reaction.
And B: synthesis of 3-bromo-N- (4-chloro-2- ((2-chloro-4, 6-difluorophenyl) carbamoyl) -6-methylphenyl) -1- (3-chloropyridin-2-yl) -1H-pyrazole-5-carboxamide
The acid chloride prepared above was dissolved in 40 ml of tetrahydrofuran, slowly added dropwise at 0 ℃ to tetrahydrofuran containing 2-amino-5-chloro-N- (2-chloro-4, 6-difluorophenyl) -3-methylbenzamide (4.4 g, 13.3 mmol) and diisopropylethylamine (2.9 ml, 17.3 mmol), transferred to room temperature for 0.5 h and checked by TLC for completion of the reaction. Diluting with 80 ml of dichloromethane, washing with 1mol/l hydrochloric acid solution, saturated sodium bicarbonate solution and saturated sodium chloride solution in sequence, drying the organic phase, desolventizing, and recrystallizing with dichloromethane and N-hexane to obtain 3-bromo-N- (4-chloro-2- ((2-chloro-4, 6-difluorophenyl) carbamoyl) -6-methylphenyl) -1- (3-chloropyridin-2-yl) -1H-pyrazole-5-carboxamide as a white solid with a yield of 52% and a melting point of 242 ℃ and 243 ℃.
Derivatives I (details: 01-522) prepared according to the preparation methods of examples 1-2 but using different starting materials are shown in Table 1, and some derivatives1H NMR (Bruker AV400 spectrometer, tetramethylsilane as internal standard) data are shown in Table 2.
TABLE 1 chemical structures of bisamide-based derivatives containing aromatic amide according to the present invention
TABLE 2 NMR data for some of the compounds of the invention
Example 4:
the derivatives (01-522) provided by the invention are used for testing, and the evaluation on the biological activity of pests is verified:
any of the derivatives (01-522) provided by the present invention was dissolved in a solvent, water and surfactant, mixed to a homogeneous aqueous phase, and diluted with water to any desired concentration for use, and the test subjects and test methods were as follows:
1) evaluation of biological activity of oriental armyworm: the test insects were oriental armyworm (Mythimna separate Walker), a normal population raised indoors with corn leaves; dipping the corn leaves in the seedling stage into the prepared solution by adopting a leaf dipping method; air-drying, placing into a culture dish with diameter of 7 cm, inoculating 4-instar larvae, and repeating for 3 times at each concentration; the control was fed with larvae by dipping corn leaves in acetone solution and the results were observed after 24 hours, 48 hours, and 72 hours.
2) Evaluation of biological Activity of Plutella xylostella: the tested insects were diamondback moth 2-instar larvae (Plutella xylostella (L.)), a normal population normally raised indoors; soaking cabbage leaves in the prepared solution for 2-3 seconds by using deterrent seeds by adopting a leaf soaking method, and throwing off residual liquid; 1 tablet at a time, 3 tablets per sample; after the liquid medicine is dried, putting the liquid medicine into a straight test tube with the length of 10 cm, inoculating 2-year-old plutella xylostella larvae, and covering the tube opening with gauze; the test treatments were placed in a standard chamber and the test results were observed after 24 hours, 48 hours, 72 hours.
The test results of the above test are shown in table 3.
The insecticidal activity of part of compounds is equivalent to that of Chlorantraniliprole (English common name: Chlorantraniliprole) serving as a positive control drug, even exceeds that of a positive control medicament, the insecticidal activity of part of compounds to diamond back moths is equivalent to that of a compound ZXL-10 reported in patent document CN109928928A, the insecticidal activity of ZXL-10 to oriental armyworms is obviously lower than that of the positive control Chlorantraniliprole and all compounds of the invention, the insecticidal activity to the diamond back moths is superior to that of the positive control Chlorantraniliprole, and the activity of the high-activity compound 295 of the invention is equivalent to that of ZXL-10. The insecticidal activity of ZXL-10 to Spodoptera frugiperda is inferior to that of positive control chlorantraniliprole, and the insecticidal activities of the high-activity compounds 34 and 51 are both higher than that of ZXL-10 and are basically equivalent to that of the positive control chlorantraniliprole.
Therefore, the insecticidal spectrum of the high-activity compound is wider than that of a compound ZXL-10 reported in patent document CN109928928A, and specific test results are shown in the following tables 4, 5 and 6. The chemical structure of ZXL-10 is as follows:
compound ZXL-10
TABLE 3 insecticidal Activity test results of some of the compounds of the present invention against Lepidoptera pests
| NO. | Oriental armyworm (10 mg/L) | Diamondback moth (0.5 mg/L) | Vegetable field spodoptera littoralis (25 mg/L) |
| 01 | A | A | A |
| 02 | A | A | A |
| 03 | A | A | A |
| 04 | A | A | A |
| 05 | A | A | A |
| 06 | A | A | A |
| 07 | A | A | A |
| 08 | A | A | A |
| 09 | A | A | A |
| 19 | A | A | A |
| 20 | A | A | A |
| 21 | A | A | A |
| 34 | A | A | A |
| 35 | A | A | A |
| 47 | A | A | A |
| 48 | A | A | A |
| 49 | A | A | A |
| 51 | A | A | A |
| 52 | A | A | A |
| 53 | A | A | A |
| 175 | A | A | A |
| 177 | A | A | A |
| 208 | A | A | A |
| 223 | A | A | A |
| 225 | A | A | A |
| 262 | A | A | A |
| 263 | A | A | A |
| 264 | A | A | A |
| 295 | A | A | A |
| 296 | A | A | A |
| 308 | A | A | A |
| 309 | A | A | A |
| 310 | A | A | A |
| 312 | A | A | A |
| 313 | A | A | A |
| 436 | A | A | A |
| 438 | A | A | A |
| 469 | A | A | A |
| Chlorantraniliprole | A | A | A |
Mortality rating in table: the grade A is 100-90%.
Table 4 insecticidal Activity of highly active Compounds and Positive controls on Oriental armyworm (%)
Table 5 shows the insecticidal activity (%)
TABLE 6 insecticidal Activity of highly active Compounds and Positive controls against Spodoptera frugiperda (%)
ND: not tested.
Claims (7)
1. A bisamide derivative containing aromatic amide has the following general formula (I):
in the formula: r1Is halogen, CF3、CHF2、CF2CF3、CN、NO2、NH2、OCF3、OCH2CF3、SOCF3、SOCHF2、SO2CHF2、C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C3-C6Cycloalkoxy, halo C3-C6Cycloalkoxy, C1-C6Alkylthio, halo C1-C6Alkylthio radical, C2-C6Alkenyl, halo C2-C6Alkenyl radical, C2-C6Alkenyloxy, halogeno C2-C6Alkenyloxy radical, C2-C6Alkynyl, halo C2-C6Alkynyl, C2-C6An alkanoyloxy group;
R2is H, halogen, NO2、CN、CH3SO、CH3SO2、C1-C6Alkyl radical, C1-C6Alkoxy radical, C1-C6Alkylthio radical, C3-C6Cycloalkyl, benzene, halo-substituted benzene;
R3is H, halogen, NO2、CN、CH3SO、CH3SO2、C1-C6Alkyl radical, C1-C6Alkoxy radical, C1-C6Alkylthio radical, C3-C6Cycloalkyl, benzene, halogen-substituted benzene;
R4、R5、R6、R7、R8is halogen, CN, NO2、CF3、OCF3Heptafluoroisopropyl group, C1-C6Alkyl, halo C1-C6Alkyl radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C1-C6Alkylthio, halo C1-C6Alkylthio radical, CH3SO、CH3SO2；
The aromatic amide-containing bisamide derivative I according to claim 1, characterized in that:
halogen is fluorine, chlorine, bromine or iodine; alkyl is straight or branched chain alkyl;
haloalkyl is a straight or branched chain alkyl; the hydrogen atoms on these alkyl groups may be partially or wholly substituted with halogen atoms; "haloalkoxy", "halocycloalkyl", "halocycloalkoxy" and "haloalkenyl" are as defined under the term "haloalkyl";
alkenyl is a straight-chain or branched-chain having 2 to 6 carbon atoms and may have a double bond in any position;
alkynyl is straight-chain or branched having 2 to 6 carbon atoms and may have a triple bond at any position.
2. A synthetic method of bisamide derivative I containing aromatic amide is shown as follows:
the preparation steps are as follows:
step (1): mixing the compound of the general formula II with acyl chloride and an organic solvent, adding a drop of N, N-dimethylformamide, reacting for 3 hours at room temperature, and concentrating under reduced pressure to obtain a compound III;
step (2): mixing the compound shown in the general formula IV with an organic solvent and alkali, dropwise adding the compound shown in the general formula III at 0 ℃ (the molar ratio of the compound shown in the general formula III to the compound shown in the general formula IV is 1: 1), and heating to room temperature to react to obtain a target compound I; the groups in the reaction formula are as described above; the organic solvent is dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane, tetrahydrofuran or 1, 4-dioxane; the acyl chloride is oxalyl chloride and thionyl chloride; the base is triethylamine, pyridine, N-dimethylaniline, diisopropylethylamine or N-methylmorpholine.
3. The use of the bisamide-based derivative containing an aromatic amide according to claim 1, wherein: the insecticidal composition is used for preparing agricultural insecticides, and is particularly used for controlling lepidoptera insects such as oriental armyworm, plutella xylostella and spodoptera frugiperda; the pesticide composition can also be used as an active ingredient and matched with agriculturally acceptable auxiliaries to be used for controlling insects.
4. The bisamide derivative containing an aromatic amide as claimed in claim 1, which is used for preparing an agricultural pesticidal composition comprising the bisamide derivative of an aromatic amide as an active ingredient in an amount of 0.1 to 99.9% by weight, 99.9 to 0.1% by weight of a solid or liquid adjuvant, and optionally 0 to 25% by weight of a surfactant.
5. An agricultural insecticidal compound composition, which contains the bisamide derivative I containing aromatic amide in claim 1 and other commercial insecticides as active ingredients, wherein the ratio of the bisamide derivative I containing aromatic amide to the other commercial insecticides is 1% to 99% to 1% by mass, the content of the active ingredients is 1 to 99% by weight, and the content of the solid or liquid auxiliary agent is 99 to 1% by weight.
6. An agricultural sterilization and acaricidal compound composition, which contains the bisamide derivative I containing aromatic amide in claim 1 and other commercial sterilization and acaricidal agents as active ingredients, wherein the ratio of the bisamide derivative I containing aromatic amide to the other commercial sterilization and acaricidal agents is 1% to 99% to 1% by mass, the content of the active ingredients is 1 to 99% by weight, and the content of the solid or liquid auxiliary agents is 99 to 1% by weight.
7. A compound composition of an anti-plant virus agent comprises the aromatic amide-containing bisamide derivative I and other commercial anti-plant virus agents which are compounded to serve as active ingredients, wherein the mass percentage of the aromatic amide-containing bisamide derivative I to the other commercial anti-plant virus agents is 1% to 99% to 1%, the content of the active ingredients is 1 to 99% by weight, and the weight of the active ingredients is 99 to 1% by weight of solid or liquid auxiliary agents.
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| CN117105908A (en) * | 2023-10-23 | 2023-11-24 | 帕潘纳(北京)科技有限公司 | Bisamide pesticide and application thereof |
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| CN112939866A (en) * | 2019-12-10 | 2021-06-11 | 南开大学 | Fluorine-substituted phenyl pyrazole amide derivative and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117105908A (en) * | 2023-10-23 | 2023-11-24 | 帕潘纳(北京)科技有限公司 | Bisamide pesticide and application thereof |
| CN117105908B (en) * | 2023-10-23 | 2023-12-22 | 帕潘纳(北京)科技有限公司 | Bisamide pesticide and application thereof |
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