CN109928928A - Bisamide analog derivative of one kind Phenylpyrazole containing N- and its preparation method and application - Google Patents
Bisamide analog derivative of one kind Phenylpyrazole containing N- and its preparation method and application Download PDFInfo
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Abstract
The bisamide analog derivative of the Phenylpyrazole containing N- the present invention relates to one kind shown in logical formula (I) with insecticidal activity and its preparation and application, by on the basis of existing bisamide class compound, different substituted phenyl ring are introduced 1 of pyrazole ring, wherein R1、R2、R3、R4、R5、R6、R7、R8、R9As defined in specification.The solution have the advantages that: original compound drug resistance is not only improved, insecticidal activity is improved, reduces production cost, it is especially largely effective to lepidoptera pests such as oriental armyworm, diamondback moths, it is a kind of insecticide with broad prospect of application.
Description
Technical field
The present invention relates to the synthetic technology of agricultural chemical insecticide, the bisamide of especially a kind of structure of Phenylpyrazole containing N-
Analog derivative and its preparation method and application.
Background technique
Currently, chemical insecticide is one of the effective means for preventing and treating agricultural pests, but as conventional pesticides are extensive
Unreasonable use causes the insect-resistant problem got worse and environmental problem, needs constantly to research and develop green high-efficient, low toxicity, low
Cost and the unique novel pesticide kind of the mechanism of action.
Adjacent formamido benzamide compound is effective insecticide of the lepidoptera pest of exploitation prevention and treatment in recent years.Japan
Pesticide company, DuPont Corporation, Bayer Bitterfeld GmbH agriculture section and domestic many colleges and universities and scientific research institution have successively applied largely
Patent, it was recently reported that a large amount of compound.
There is the noval chemical compound of insecticidal bioactivity for design synthesis, improve its drug resistance, and reduce production cost, design
The bisamide analog derivative for having no a kind of structure of Phenylpyrazole containing N- reported in the literature is synthesized, biological activity test shows this
Analog derivative insecticidal activity with higher.
Summary of the invention
It is an object of the invention to bisamide analog derivative of a kind of structure of Phenylpyrazole containing N- and preparation method thereof and answer
With the analog derivative can improve the drug resistance of original compound, and can be improved its insecticidal activity, the effect of this analog derivative
After insect, there is anorexia, dispirited, vomiting de- excrement, the immoderate contraction of muscle in polypide, eventually leads to the symptoms such as death.
The analog derivative can be used as insecticide and be used for the lepidoptera pests such as oriental armyworm and diamondback moth insecticidal activity with higher
The agriculturally prevention and treatment of pest.
The bisamide analog derivative of the structure of Phenylpyrazole containing N- provided by the invention has logical formula (I) as follows:
In formula:
R1For H, C1-C6Alkyl, halogenated C1-C6Alkyl, C2-C6Alkenyl, halogenated C2-C6Alkenyl, C2-C6Alkynyl, halogenated C2-C6
Alkynyl, C3-C6Naphthenic base or halogenated C3-C6Naphthenic base；
R2For H, halogen, cyano, nitro, C1-C6Alkyl or halogenated C1-C6Alkyl；
R3For C1-C6Alkyl, halogenated C1-C6Alkyl, methyl mercapto replace alkyl, C2-C6Alkenyl, halogenated C2-C6Alkenyl, C2-C6
Alkynyl, halogenated C2-C6Alkynyl, methyl mercapto replace unsaturated alkyl, C3-C6Naphthenic base or halogenated C3-C6Naphthenic base (do not include by
At least one C3-C4Naphthenic base replace alkyl), substituted sulphonyl, substituted-amino formoxyl, replace N- cyano sulfone (sulphur) imines
Or benzyl, wherein the H in benzyl rings can be by halogen, C1-C6Alkyl, halogenated C1-C6Alkyl is further substituted with；
R4For halogen, trifluoromethyl, cyano, SOCF3、OCF3、SOCHF2、SO2CHF2、C1-C6Alkylthio group, halogenated C1-C6Alkane
Sulfenyl, C1-C6Alkoxy, halogenated C1-C6Alkoxy, halogenated C2-C6Alkynyloxy group, C2-C6Alkanoyloxy, C2-C6It is alkenyloxy group, halogenated
C2-C6Alkenyloxy group, C2-C6Alkynyloxy group；
R5, R6, R7, R8, R9For halogen, nitro, cyano, trifluoromethyl, C1-C6Alkylamidoalkyl, C1-C6Alkyl amino acid
Ester group, C1-C6Alkyl sulfide urea groups, C1-C6Alkyl urea groups, C1-C6Alkyl N- cyano sulfoxide group, C1-C6Alkyl N- cyanoimino,
C1-C6Alkyl N-TFA base sulfoxide group, C1-C6Alkyl N-TFA base imido grpup；
In the definition of said derivative, no matter term used exclusive use is also used in compound word, representative takes as follows
Dai Ji:
Halogen is fluorine, chlorine, bromine or iodine；
Alkyl is linear or branched alkyl group；
Halogenated alkyl is linear or branched alkyl group, and the hydrogen atom on these alkyl can partly or entirely be taken by halogen atom
Generation；The definition of " halogenated alkenyl ", " halo alkynyl " and " halogenated cycloalkyl " is identical as term " halogenated alkyl "；
Alkenyl be have 2-6 carbon atom linear chain or branched chain and can in any position on there are double bonds；
Alkynyl be have 2-6 carbon atom linear chain or branched chain and can in any position on there are three keys.
The synthetic method of the bisamide analog derivative of one kind structure of Phenylpyrazole containing N-, as follows:
Preparation step is as follows:
1) there are two types of synthetic methods for compound of Formula IV:
Method one: Compounds of formula II, organic solvent and water mixing are added with stirring oxidant, are then 0 DEG C in temperature
It is reacted 0.5-48 hours under to solvent reflux temperature, after filtering, organic solvent is sloughed in decompression, and it is basified to after pH12 with alkali soluble,
Organic impurities is extracted with organic solvent, water phase is acidified to pH1.5, and target compound IV is made；
Method two: compound of formula III, organic solvent and water mixing are added alkali, are stirred at room temperature 0.5-48 hours, depressurize
Organic solvent is sloughed, extracts organic impurities with organic solvent to after pH12 with alkali soluble is basified, water phase is acidified to pH1.5, is made
Compound IV；
2) above-mentioned compound of Formula IV and compounds of formula V are dissolved in organic solvent according to 1: 1 molar ratio, at 0 DEG C
Pyridine is added, after 10-30 minutes, mesyl chloride is added dropwise, is warmed to room temperature, stir 0.5-48 hours, Formula VII compound is added,
0.5-48 hours obtained target compound I are reacted in the case where temperature is 0 DEG C to solvent reflux temperature.Each group institute as above in reaction equation
Show.
The organic solvent is methylene chloride, chloroform, carbon tetrachloride, benzene,toluene,xylene, hexamethylene, n-hexane, second
Acetoacetic ester, tetrahydrofuran, Isosorbide-5-Nitrae-dioxane, n,N-Dimethylformamide or dimethyl sulfoxide.
The oxidant is potassium permanganate, metachloroperbenzoic acid, sodium hypochlorite, NaIO4/RuO2, hydrogen peroxide or ozone
The alkali be triethylamine, pyridine, 1,8- diaza-bicyclic (5,4,0), 11 carbon -7- alkene, n,N-Dimethylaniline,
Sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, sodium tert-butoxide or potassium tert-butoxide.
The acid is methane sulfonic acid, benzene sulfonic acid, p-methyl benzenesulfonic acid, acetic acid, phosphate, hydrochloric acid, sulfuric acid or phosphoric acid.
The bisamide analog derivative of one kind structure of Phenylpyrazole containing N- of the present invention is used to prepare agrochemicals desinsection
Agent, especially for prevention and treatments of insects such as oriental armyworm, diamondback moths.
The bisamide analog derivative of the structure of Phenylpyrazole containing N- provided by the invention is equipped with agricultural as active constituent can be with
The composition pesticide of the auxiliary agent composition of receiving is used to prevent and treat the prevention and treatment of insect.
The solution have the advantages that: the drug resistance of original compound is not only improved, and improves insecticidal activity, it is raw
Produce at low cost, preparation method is simple, can be widely used for preparing agricultural chemical insecticide.
Specific embodiment
It further illustrates the present invention with reference to embodiments, the purpose is to be better understood on the contents of the present invention is body
Existing substantive distinguishing features of the invention, therefore the cited case is not construed as limiting the scope of the invention.
Embodiment 1:
N- [4- chloro-2-methyl -6- [(methylcarbamoyl) phenyl] -1- (52,6- bis- chloro-4 nitrophenyl) -3-
The synthesis of (trifluoromethyl) -1H- pyrazoles -5- formamide (derivative 08)
1) step A:N- [4- chloro-2-methyl -6- [(methylcarbamoyl) phenyl] -1- (2,6- bis- chloro- 4- nitrobenzenes
Base) -3- (trifluoromethyl) -1H- pyrazoles -5- formamide
By 11.76g (30mmol) 3- Trifluoromethyl-1-((2,6- bis- chloro- 4- nitro) phenyl)-5- (furans-2- base)-
1H- pyrazoles is dissolved in the mixed solution of 50mL acetone and water, and 9.48g (60mmol) potassium permanganate is added in batches and adds, is warming up to
Reflux, reacts 0.5h, and TLC detects fully reacting；Filtering, filtrate decompression sloughs acetone, abundant with 2mol/L potassium hydroxide solution
Then to pH12 organic impurities is extracted with ethyl acetate, water phase is that 2mol/L hydrochloric acid solution is acidified to pH1 with concentration, analysis in alkalization
Solid out filters drying, obtains 3- Trifluoromethyl-1-((2,6- bis- chloro- 4- nitro) phenyl)-1H- pyrazoles-5- formic acid, yellowish
Color solid, yield 76.6%, m.p.141-142 DEG C
2) step B: preparation N- [4- chloro-2-methyl -6- [(methylcarbamoyl) phenyl] -1- (2,6- bis- chloro- 4- nitre
Base phenyl) -3- (trifluoromethyl) -1H- pyrazoles -5- formamide
By 0.370g (1mmol) 3- Trifluoromethyl-1-((2,6- bis- chloro- 4- nitro) phenyl)-1H- pyrazoles-5- formic acid and
0.185g (1mmol) 2- amino -3- methyl-5-chloro benzoic acid is dissolved in 20mL methylene chloride, and 0.086g is added at 0 DEG C
(1.1mmol) pyridine is added dropwise 0.229g (2 mmol) mesyl chloride, is warmed to room temperature after ten minutes, stirs 8 hours, is added
The methylamine water solution of 1.5mmol after reaction 7 hours, removes solvent, and water, saturated sodium bicarbonate water are successively used in ethyl acetate extraction
Solution, dilute hydrochloric acid, saturated common salt water washing merge organic layer, and dry, precipitation is recrystallized to give with ethyl acetate and petroleum ether
N- [4- chloro-2-methyl -6- [(methylcarbamoyl) phenyl] -1- (2,6- bis- chloro-4 nitrophenyl) -3- (trifluoromethyl) -
1H- pyrazoles -5- formamide, faint yellow solid, yield 60.9%, m.p.155-156 DEG C.
Embodiment 2:
N- [4- chloro-2-methyl -6- [(methylcarbamoyl) phenyl] -1- (the chloro- 5- nitrobenzophenone of 2-) -3- (fluoroform
Base) -1H- pyrazoles -5- formamide (derivative 176) synthesis
1) step A: preparation 3- Trifluoromethyl-1-((the chloro- 5- nitro of 2-) phenyl)-1H- pyrazoles-5- formic acid
By 10.71g (30mmol) 3- Trifluoromethyl-1-((the chloro- 5- nitro of 2-) phenyl)-5- (furans-2- base)-1H- pyrrole
Azoles is dissolved in the mixed solution of 50mL acetone and water, and 9.48g (60mmol) potassium permanganate is added in batches and adds, is warming up to reflux,
0.5h is reacted, TLC detects fully reacting；Filtering, filtrate decompression sloughs acetone, with 2mol/L potassium hydroxide solution sufficiently alkalize to
Then organic impurities is extracted with ethyl acetate in pH12, water phase is that 2mol/L hydrochloric acid solution is acidified to pH1 with concentration, and solid is precipitated,
Drying is filtered, 3- Trifluoromethyl-1-((the chloro- 5- nitro of 2-) phenyl)-1H- pyrazoles-5- formic acid, faint yellow solid, yield are obtained
76.6%, m.p.121-122 DEG C
2) step B: preparation N- [4- chloro-2-methyl -6- [(methylcarbamoyl) phenyl] -1- (chloro- 5- nitrobenzene of 2-
Base) -3- (trifluoromethyl) -1H- pyrazoles -5- formamide
By 0.335g (1mmol) 3- Trifluoromethyl-1-((the chloro- 5- nitro of 2-) phenyl)-1H- pyrazoles-5- formic acid and
0.185g (1mmol) 2- amino -3- methyl-5-chloro benzoic acid is dissolved in 20mL methylene chloride, and 0.086g is added at 0 DEG C
(1.1mmol) pyridine is added dropwise 0.229g (2mmol) mesyl chloride, is warmed to room temperature after ten minutes, stirs 8 hours, is added
The methylamine water solution of 1.5mmol after reaction 7 hours, removes solvent, and water, saturated sodium bicarbonate water are successively used in ethyl acetate extraction
Solution, dilute hydrochloric acid, saturated common salt water washing merge organic layer, and dry, precipitation is recrystallized to give with ethyl acetate and petroleum ether
N- [4- chloro-2-methyl -6- [(methylcarbamoyl) phenyl] -1- (the chloro- 5- nitrobenzophenone of 2-) -3- (trifluoromethyl) -1H-
Pyrazoles -5- formamide, faint yellow solid, yield 66.1%, m.p.145-146 DEG C.
Embodiment 3:
N- [4- chloro-2-methyl -6- [(methylcarbamoyl) phenyl] -1- (chloro- 4, the 5- difluorophenyl of 2-) -3- (trifluoro
Methyl) -1H- pyrazoles -5- formamide (derivative 624) synthesis
1) step A: preparation 3- Trifluoromethyl-1-((chloro- 4, the 5- difluoro of 2-) phenyl)-1H- pyrazoles-5- formic acid
By 10.44g (30mmol) 3- Trifluoromethyl-1-((chloro- 4, the 5- difluoro of 2-) phenyl)-5- (furans-2- base)-1H-
Pyrazoles is dissolved in the mixed solution of 50mL acetone and water, and 9.48g (60mmol) potassium permanganate is added in batches and adds, is warming up to back
Stream reacts 0.5h；TLC detects fully reacting；Filtering, filtrate decompression sloughs acetone, with the abundant alkali of 2mol/L potassium hydroxide solution
Change to pH12, organic impurities is then extracted with ethyl acetate, water phase is that 2mol/L hydrochloric acid solution is acidified to pH1, acetic acid with concentration
Ethyl ester extraction, saturated common salt water washing merge organic layer, dry, precipitation rear pillar chromatograph 3- Trifluoromethyl-1-((2- chloro- 4,
5- difluoro) phenyl) -1H- pyrazoles -5- formic acid, white solid, yield 62.3%, m.p.147-148 DEG C.
2) step B: preparation N- [4- chloro-2-methyl -6- [(methylcarbamoyl) phenyl] -1- (chloro- 4,5- difluoro of 2-
Phenyl) -3- (trifluoromethyl) -1H- pyrazoles -5- formamide
By 0.325g (1mmol) 3- Trifluoromethyl-1-((chloro- 4, the 5- difluoro of 2-) phenyl)-1H- pyrazoles-5- formic acid and
0.185g (1mmol) 2- amino -3- methyl-5-chloro benzoic acid is dissolved in 20mL methylene chloride, and 0.086g is added at 0 DEG C
(1.1mmol) pyridine is added dropwise 0.229g (2 mmol) mesyl chloride, is warmed to room temperature after ten minutes, stirs 8 hours, is added
The methylamine water solution of 1.5mmol after reaction 7 hours, removes solvent, and water, saturated sodium bicarbonate water are successively used in ethyl acetate extraction
Solution, dilute hydrochloric acid, saturated common salt water washing merge organic layer, and dry, precipitation rear pillar chromatographs to obtain N- [4- chloro-2-methyl -6-
[(methylcarbamoyl) phenyl] -1- (chloro- 4, the 5- difluorophenyl of 2-) -3- (trifluoromethyl) -1H- pyrazoles -5- formamide is white
Color solid, yield 64.7%, m.p.260-261 DEG C.
Now according to the preparation method of embodiment 1-3 but using the analog derivative 01-868 of different raw material preparations, column
Enter table 1, partial derivatives1H NMR(Bruker AV400 spectrometer using tetramethylsilane as
The internal standard) data are included in table 2.
Table 1
Table 2
Embodiment 4:
It is tested, is verified to pest biological evaluation using derivative provided by the invention (01~868):
Any derivative (01~868) provided by the invention is dissolved in solvent, water and surfactant, is mixed into
One water phase, when use, are diluted with water to any desired concentration, and test object and test method are as follows:
1) to the biological evaluation of oriental armyworm: being oriental armyworm (Mythimna separata for examination insect
Walker), the normal population of indoor maize leaves raising；Using leaf dipping method, Maize Seedling leaf is impregnated in configured good solution
In；It is put into after drying in diameter 7cm culture dish, accesses 4 instar larvaes, each concentration is repeated 3 times；Control acetone soln impregnates beautiful
Rice leaf breeding grub, observes test result after 24 hours, 48 hours, 72 hours.
2) to the biological evaluation of diamondback moth: being 2 instar larvae of diamondback moth (Plutella xylostella for examination insect
It (L.)) is, the indoor normal population normally raised；Using leaf dipping method, with tweezers dipping cabbage leaves in configured good solution
In, time 2-3 second, get rid of extraction raffinate；1 tablet once, and totally 3, each sample；After medical fluid is dry, it is put into the straight type test tube of 10cm long
It is interior, 2 age diamondback moth larvaes are accessed, cover nozzle with gauze；Test process is placed in standard process chamber, 24 hours, 48 hours,
Test result is observed after 72 hours.
The test result of above-mentioned test is as shown in table 3.
Table 3
| No. | Oriental armyworm (100ppm) | Diamondback moth (100ppm) |
| 08 | A | A |
| 09 | A | A |
| 11 | A | A |
| 14 | A | A |
| 64 | A | A |
| 65 | A | A |
| 67 | A | A |
| 70 | A | A |
| 92 | A | A |
| 95 | A | A |
| 98 | A | A |
| 120 | A | A |
| 176 | A | A |
| 179 | A | A |
| 182 | A | A |
| 316 | A | A |
| 319 | A | A |
| 322 | A | A |
| 596 | A | A |
| 624 | A | A |
| Chlorantraniliprole | A | A |
Mortality levels in table: A grades are 100%-90%.
Part of compounds insecticidal activity is lifted quite or more than comparison medicine chlorine worm benzamide (Chlorantraniliprole)
Such as the following table 4 and table 5:
Table 4
Table 5
Claims (7)
1. the bisamide analog derivative of a kind of Phenylpyrazole containing N-, it is characterised in that have logical formula (I) as follows:
In formula:
R1For H, C1-C6Alkyl, halogenated C1-C6Alkyl, C2-C6Alkenyl, halogenated C2-C6Alkenyl, C2-C6Alkynyl, halogenated C2-C6Alkynyl,
C3-C6Naphthenic base or halogenated C3-C6Naphthenic base；
R2For H, halogen, cyano, nitro, C1-C6Alkyl or halogenated C1-C6Alkyl；
R3For C1-C6Alkyl, halogenated C1-C6Alkyl, methyl mercapto replace alkyl, C2-C6Alkenyl, halogenated C2-C6Alkenyl, C2-C6Alkynyl,
Halogenated C2-C6Alkynyl, methyl mercapto replace unsaturated alkyl, C3-C6Naphthenic base or halogenated C3-C6Naphthenic base (does not include by least one
A C3-C4The alkyl that naphthenic base replaces), substituted sulphonyl, substituted-amino formoxyl, replace N- cyano sulfone (sulphur) imines or benzyl,
Wherein the H in benzyl rings can be by halogen, C1-C6Alkyl, halogenated C1-C6Alkyl is further substituted with；
R4For halogen, trifluoromethyl, cyano, SOCF3、OCF3、SOCHF2、SO2CHF2、C1-C6Alkylthio group, halogenated C1-C6Alkylthio group,
C1-C6Alkoxy, halogenated C1-C6Alkoxy, halogenated C2-C6Alkynyloxy group, C2-C6Alkanoyloxy, C2-C6Alkenyloxy group, halogenated C2-C6Alkene
Oxygroup, C2-C6Alkynyloxy group；
R5, R6, R7, R8, R9For halogen, nitro, cyano, trifluoromethyl, C1-C6Alkylamidoalkyl, C1-C6Alkyl amino perester radical,
C1-C6Alkyl sulfide urea groups, C1-C6Alkyl urea groups, C1-C6Alkyl N- cyano sulfoxide group, C1-C6Alkyl N- cyanoimino, C1-C6
Alkyl N-TFA base sulfoxide group, C1-C6Alkyl N-TFA base imido grpup；
In the definition of said derivative, no matter term used exclusive use is also used in compound word, following substituent group is represented:
Halogen is fluorine, chlorine, bromine or iodine；
Alkyl is linear or branched alkyl group；
Halogenated alkyl is linear or branched alkyl group, and the hydrogen atom on these alkyl can partly or entirely be replaced by halogen atom；
The definition of " halogenated alkenyl ", " halo alkynyl " and " halogenated cycloalkyl " is identical as term " halogenated alkyl "；
Alkenyl be have 2-6 carbon atom linear chain or branched chain and can in any position on there are double bonds；
Alkynyl be have 2-6 carbon atom linear chain or branched chain and can in any position on there are three keys.
2. the synthetic method of the bisamide analog derivative of a kind of Phenylpyrazole containing N-, as follows:
Preparation step is as follows:
Step (1): there are two types of synthetic methods for compound of Formula IV:
Method one: Compounds of formula II, organic solvent and water mixing are added with stirring oxidant, are then 0 DEG C extremely molten in temperature
It is reacted 0.5-48 hours under agent reflux temperature, after filtering, organic solvent is sloughed in decompression, basified to after pH 12 with alkali soluble, with having
Solvent extracts organic impurities, and water phase is acidified to pH 1.5, and target compound IV is made；
Method two: compound of formula III, organic solvent and water mixing are added alkali, are stirred at room temperature 0.5-48 hours, decompression is sloughed
Organic solvent, it is basified to after pH 12 with alkali soluble, organic impurities is extracted with organic solvent, water phase is acidified to pH 1.5, obtainedization
Close object IV；
Step (2): above-mentioned compound of Formula IV and compounds of formula V are dissolved in organic solvent according to 1: 1 molar ratio, 0 DEG C
Lower addition pyridine after 10-30 minutes, is added dropwise mesyl chloride, is warmed to room temperature, stir 0.5-48 hours, general formula VII chemical combination is added
Object reacts 0.5-48 hours obtained target compound I in the case where temperature is 0 DEG C to solvent reflux temperature.Each group is such as in reaction equation
Shown on.
3. the preparation method of the bisamide analog derivative of the structure of Phenylpyrazole containing N- according to claim 2, it is characterised in that:
The organic solvent is methylene chloride, chloroform, carbon tetrachloride, benzene,toluene,xylene, hexamethylene, n-hexane, ethyl acetate, four
Hydrogen furans, Isosorbide-5-Nitrae-dioxane, n,N-Dimethylformamide or dimethyl sulfoxide.
4. the preparation method of the bisamide analog derivative of the Phenylpyrazole containing N- according to claim 2, it is characterised in that: described
Oxidant is potassium permanganate, metachloroperbenzoic acid, sodium hypochlorite, NaIO4/RuO2, hydrogen peroxide or ozone.
5. the preparation method of the bisamide analog derivative of the Phenylpyrazole containing N- according to claim 2, it is characterised in that: described
Alkali is triethylamine, pyridine, 1,8- diaza-bicyclic (5,4,0), 11 carbon -7- alkene, n,N-Dimethylaniline, sodium hydroxide, hydrogen
Potassium oxide, sodium carbonate, potassium carbonate, sodium methoxide, sodium tert-butoxide or potassium tert-butoxide.
6. the preparation method of the bisamide analog derivative of the Phenylpyrazole containing N- according to claim 2, it is characterised in that: described
Acid is methane sulfonic acid, benzene sulfonic acid, p-methyl benzenesulfonic acid, acetic acid, phosphate, hydrochloric acid, sulfuric acid or phosphoric acid.
7. the application of a kind of bisamide analog derivative of the Phenylpyrazole containing N- according to claim 1, it is characterised in that: be used for
Agricultural chemical insecticide is prepared, especially for prevention and treatments of insects such as oriental armyworm, diamondback moths；Active constituent is alternatively arranged as to match
The composition pesticide formed with agriculture acceptable auxiliary agent is used to prevent and treat the prevention and treatment of insect.
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| CN114621144A (en) * | 2022-03-23 | 2022-06-14 | 南开大学 | Cyano-substituted phenyl pyrazole amide derivative and preparation method and application thereof |
| CN114716409A (en) * | 2021-01-05 | 2022-07-08 | 西北农林科技大学 | Diphenyl pyrazole compound and preparation method and application thereof |
| CN114716408A (en) * | 2022-03-23 | 2022-07-08 | 南开大学 | Bisamide derivative containing aromatic amide and preparation method and application thereof |
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| CN114716408A (en) * | 2022-03-23 | 2022-07-08 | 南开大学 | Bisamide derivative containing aromatic amide and preparation method and application thereof |
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