CN103936674A - Benzamide or acylhydrazone derivative containing 5-trifluoromethyl-4-pyrazole amide structure, and application of derivative - Google Patents

Benzamide or acylhydrazone derivative containing 5-trifluoromethyl-4-pyrazole amide structure, and application of derivative Download PDF

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CN103936674A
CN103936674A CN201410187443.6A CN201410187443A CN103936674A CN 103936674 A CN103936674 A CN 103936674A CN 201410187443 A CN201410187443 A CN 201410187443A CN 103936674 A CN103936674 A CN 103936674A
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pyrazole
trifluoromethyl
phenyl
chloro
carboxamide
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吴志兵
吴世喜
张滕滕
叶意强
邝继清
杨松
胡德禹
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Guizhou University
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Guizhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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
    • 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
    • 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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Abstract

The invention discloses an application of a benzamide or acylhydrazone derivative containing a 5-trifluoromethyl-4-pyrazole amide structure in the aspect of insecticidal activity. The general structure formulas are as shown in A and B in the specification, wherein R1 refers to phenyl and 3-chloropyridyl; R2-R5 refer to hydrogen atom, alkyl, hetroatom-containing alkyl, phenyl, benzyl, heterocyclyl and substituted heterocyclyl. The benzamide or acylhydrazone derivative has broad-spectrum insecticidal activity and has excellent preventing and controlling effects on diamondback moth, heliothis armigera, ostrinia nubilalis, armyworm and sanitary pests such as culex pipiens.

Description

One class is containing benzamide or acyl hydrazone derivative and the application thereof of " 5-trifluoromethyl-4-pyrazole amide " structure
Technical field
The present invention relates to field of pesticides, disclose the benzamide or the application of acylhydrazone analog derivative aspect control Agricultural pests and sanitary insect pest that contain " 5-trifluoromethyl-4-pyrazole amide " structure.
Background technology
In recent years, reported that the Agricultural pests such as small cabbage moth, bollworm, beet armyworm, prodenia litura, citrus fruit fly, aphid cocoon honeybee, turnip aphid, striped rice borer have produced serious resistance to agricultural chemicals such as ethiprole, Avrmectin, fluorine pyridine urea, first dimension salt, pleocidin, indoxacarbs both at home and abroad, because current shortage high-efficiency low-toxicity and mechanism of action are unique, without the novel pesticide of crossed resistance mutually, cause the significantly underproduction of farm output, grain security is constituted a serious threat.The green novel pesticide of development of new is extremely urgent.In addition mosquito has the ability of diseases such as propagating singapore hemorrhagic fever, malaria, bancroftosis, filariasis malayi, encephalitis B, Japanese encephalitis, and the mankind's health in serious threat.According to the World Health Organization, approximately there are 5,000 ten thousand people in the annual whole world because singapore hemorrhagic fever is caught in the propagation of mosquito, millions of people is infected with malaria lethal or blind.Yet the long-term use to mosquito repellent, kill mosquito medicament along with people, makes the resistance of sanitary insect pest also more and more stronger, its control is also all the more difficult, and the green kill mosquito medicament of visible development of new is also imperative.
Summary of the invention
The object of the invention, in this traditional compounds, in " pyrazole amide " structure, the position of " amido linkage " is in " the 5-position " of pyrazoles, and pyrazoles " 3-position " introducing simultaneously " bromine " replaces; In the present invention, " amido linkage " in " pyrazole amide " structure is transferred to pyrazole ring " 4-position ", on pyrazole ring, " 5-position " introduces active group " trifluoromethyl " simultaneously, and benzamide or the acylhydrazone analog derivative containing 5-trifluoromethyl-4-pyrazole amide structure of a class novelty synthesized in design.Prove by experiment compound provided by the invention to Agricultural pests and sanitary insect pest with good insecticidal activity.One class is containing benzamide or the benzoyl hydrazone derivative of " 5-trifluoromethyl-4-pyrazole amide " structure, and compound structure is as shown in general formula A and B:
In formula:
R 1be selected from phenyl, 3-chloropyridine base;
R 2, R 3, R 4and R 5be selected from hydrogen atom, alkyl, heteroatom containing alkyl, phenyl, benzyl, heterocyclic radical, substituted heterocyclic radical.
Described alkyl is the alkyl of C1-C4, the branched-chain alkyl of C1-C8.
Described heterocyclic radical is pyridine cyclic group and furans cyclic group; The substituted heterocyclic radical of indication is pyridine methylene.
Be selected from following particular compound:
Numbering Compound title Structure
A1 N-(4-chloro-2-methyl 6-(methylamino formyl) phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A2 N-(4-chloro-2-methyl-6-(methylamino formyl) phenyl)-1-(3-chloropyridine-2-yl))-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A3 N-(the chloro-2-of 4-(ethylamino formyl)-6-aminomethyl phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A4 N-(the chloro-2-of 4-(ethylamino formyl)-6-aminomethyl phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A5 N-(the chloro-2-of 4-(cyclopropylamino formyl)-6-aminomethyl phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A6 N-(the chloro-6-aminomethyl phenyl of 2-(butyl carbamyl)-4-)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A7 N-(the chloro-2-of 4-(dimethylamino formyl)-6-aminomethyl phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A8 N-(the chloro-2-of 4-(cyclopropylamino formyl)-6-aminomethyl phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A9 N-(the chloro-2-of 4-(isopropylamino formyl)-6-aminomethyl phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A10 N-(the chloro-2-of 4-(isopropylamino formyl)-6-aminomethyl phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A11 N-(the chloro-6-aminomethyl phenyl of 2-(butyl carbamyl)-4-)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A12 N-(the chloro-2-of 4-(dimethylamino formyl)-6-aminomethyl phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A13 N-(the chloro-6-aminomethyl phenyl of 2-(benzylamino formyl)-4-)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A14 N-(4-chloro-2-methyl-6-((6-methyl-2-heptane base) formamyl) phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A15 N-(4-chloro-2-methyl-6-((6-methyl-2-heptane base) formamyl) phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A16 N-(4-chloro-2-methyl--6-(carbanilino) phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A17 N-(4-chloro-2-methyl-6-((4-pyridine methylene) formamido-) phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A18 N-(the chloro-6-aminomethyl phenyl of 2-(phenylcarbamoyl)-4-)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
B1 N-(4-chloro-2-methyl 6-(2-propylidene acylhydrazone) phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
B2 N-(the chloro-2-of 4-(2-((dimethylamine) methylene radical) acylhydrazone)-6-aminomethyl phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
B3 N-(the chloro-2-of 4-(2-((dimethylamine) methylene radical) acylhydrazone)-6-aminomethyl phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
B4 N-(4-chloro-2-methyl 6-(2-propylidene acylhydrazone) phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
B5 N-(4-chloro-2-methyl 6-(2-(4-methyl-isobutyl) acylhydrazone) phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
B6 N-(4-chloro-2-methyl 6-(2-(4-methyl-isobutyl) acylhydrazone) phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
B7 N-(4-chloro-2-methyl-6-(2-(3-pyridine methylene) acylhydrazone) phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
B8 N-(the chloro-6-tolyl of 2-(2-benzyl acylhydrazone)-4-)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
B9 N-(the chloro-2-of 4-(2-(furfurylidene) acylhydrazone)-6-tolyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
A described class, containing " 5-trifluoromethyl-4-pyrazole amide " benzamide of structure or application of benzoyl hydrazone derivative, is characterized in that the application for the preparation of control Agricultural pests and sanitary insect pest aspect medicine and medicament aspect.
Described derivative is in the medicine aspect control small cabbage moth, bollworm, Pyrausta nubilalis (Hubern)., mythimna separata and sanitary insect pest northern house or the application of medicament.
In pesticide composition or in health deinsectization composition, derivative content 0.000l wt%-99.9wt%, the composition outside derivative is agricultural, the acceptable diluent or carrier in health aspect.
The compounds of this invention A and B can adopt following method to be prepared:
Adopt 1with the chloro-3-tolyl acid of 2-amino-5-in suitable solvent in 0 ~ 100 obetween C, react 1 ~ 24 hour, generate intermediate 2; Intermediate 2with various amine in suitable solvent in 20 ~ 120 obetween C, react 1 ~ 12 hour, make the compounds of this invention a.Intermediate 2with hydrazine hydrate in suitable solvent in 20 ~ 120 obetween C, react 1 ~ 24 hour, generate intermediate 3; Intermediate 3with corresponding aldehyde, ketone in suitable solvent in 20 ~ 120 obetween C, react 1 ~ 12 hour, make the compounds of this invention b.Solvent can be selected from methyl alcohol, ethanol, propyl alcohol, Virahol, butanols, DMF, pyridine, acetonitrile, chloroform, methylene dichloride, toluene, benzene, Isosorbide-5-Nitrae-dioxane, acetone, acetic acid, ethyl acetate etc.
In process of the present invention, compound 1method described in can referenced patent (CN 102993097 A) is prepared.
In process of the present invention, the intermediate adopting 2can be prepared in the following ways:
Adopt 1with the chloro-3-tolyl acid of 2-amino-5-in the system of alkali and Methanesulfonyl chloride, 0 ~ 60 ounder the condition of C, react 1 ~ 12 hour, obtain intermediate 2.Solvent can be selected from methyl alcohol, ethanol, propyl alcohol, Virahol, butanols, DMF, acetonitrile, chloroform, methylene dichloride, tetrahydrofuran (THF), toluene, benzene, Isosorbide-5-Nitrae-dioxane, acetone etc.; Alkali can be selected pyridine, triethylamine, diethylamine, DMAP, K 2cO 3, NaOH.
In process of the present invention, the intermediate adopting 3can be prepared in the following ways:
Adopt 2with hydrazine hydrate in suitable solvent, in 20 ~ 120 ounder the condition of C, react 1 ~ 24 hour, obtain intermediate 3.Solvent can be selected from methyl alcohol, ethanol, propyl alcohol, Virahol, butanols, DMF, acetonitrile, chloroform, methylene dichloride, tetrahydrofuran (THF), toluene, benzene, Isosorbide-5-Nitrae-dioxane, acetone etc.
beneficial effect
Compound provided by the invention has the insecticidal activity of broad-spectrum high efficacy, particularly the lepidopterous insects such as small cabbage moth, bollworm, Pyrausta nubilalis (Hubern)., mythimna separata are had to excellent prevention effect, in addition, the part of compounds providing also has excellent insecticidal activity to Diptera sanitary insect pest (as northern house).
Embodiment
embodiment 1: n-(4-chloro-2-methyl-6-(methylamino formyl) phenyl)-1-(3-chloropyridine-2-yl)) preparation of-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide (A2)
1) the chloro-2-of 6-(1-(3-chloro-2-pyridyl)-5-Trifluoromethyl-1 H-4-pyrazolyl)-8-methyl-4H-benzo [d] [preparation (2) of 1,3] oxazine-4-ketone
In the there-necked flask of 100 mL with prolong and thermometer, add pyridine (34.3 mmol), compound 1 (17.2 mmol) and Methanesulfonyl chloride (51.4 mmol), in the backward system of stirring at normal temperature 5 min, add the chloro-3-tolyl acid of 2-amino-5-(68.6 mmol), normal-temperature reaction adds 30 mL water for 4 hours in backward system, a large amount of solids are separated out, suction filtration, filter cake washes with water, after dry, obtain intermediate 2, yellow solid, yield 89.6%, fusing point 179 ~ 181 oc. 1H NMR (DMSO-d 6): δ 8.68 (d, J = 5.2, 1H, pyridine H), 8.66 (s, 1H, pyrzole H), 8.41 (d, J = 8.0 Hz, 1H, pyridine H), 7.96 (s, 1H, pyridine H), 7.92 (s, 1H, pyridine H), 7.85-7.82 (m, 1H, pyridine H), 2.25 (s, 3H, PhCH 3); MS (ESI) : m/z 441 [M+H] +, 463 [M+Na] +.
2) n-(4-chloro-2-methyl-6-(methylamino formyl) phenyl)-1-(3-chloropyridine-2-yl)) preparation (A2) of-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
In 25 mL there-necked flasks, add respectively 2 (0.68 mmol) and acetonitrile (5 mL), methylamine (1.36 mmol) drops in reaction solution slowly, normal-temperature reaction 1 hour, has a large amount of solids to separate out, suction filtration, filter cake washs with anhydrous acetonitrile, dry, obtains target compound I2.White solid, productive rate 73.8%, fusing point 228 ~ 231 oc; 1h NMR (DMSO-d 6): δ 10.23 (s, 1H, NH), 8.65 (d, j=4.6 Hz, 1H, pyridine H), 8.41 (s, 1H, pyrazole H), 8.39-8.36 (m, 2H, pyridine H and benzene), 7.80 (m, 1H, pyridine H), 7.53 (s, 1H, benzene H), 7.39 (s, 1H, NH), 2.70 (d j=4.1 Hz, 3H, NCH 3), 2.27 (s, 3H, PhCH 3); MS (ESI): m/z 472 [M+H] +, 494 [M+Na] +; Anal. Calcd (C 19h 14c l2f 3n 5o 2): C, 48.32; H, 2.99; N, 14.83. Found:C, 48.06; H, 2.83; N, 14.77.
embodiment 2: nthe preparation of-(the chloro-2-of 4-(2-((dimethylamine) methylene radical) acylhydrazone)-6-tolyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide (B2)
1) nthe preparation of-(the chloro-2-of 4-(hydrazide group)-6-tolyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide (3)
In 50 mL there-necked flasks, add 80% hydrazine hydrate solution (13.6 mmol), 2 (6.8 mmol) and THF (15 mL), room temperature reaction 1 hour, separates out a large amount of solids in system, suction filtration, filter cake absolute ethanol washing, obtains intermediate 3, white solid after being dried, yield 93.0%, fusing point 158 ~ 160 oc. 1H NMR (DMSO-d 6): δ 10.22 (s, 1H, NH), 9.64 (s, 1H, NH), 8.66 (d, J = 4.6 Hz, 1H, pyridine H), 8.44 (s, 1H, pyrazole H), 8.39 (d, J = 8.0 Hz, 1H, pyridine H), 7.82-7.79 (m, 1H, pyridine H), 7.52 (s, 1H, benzene H), 7.54 (s, 1H, benzene H), 7.36 (s, 1H, benzne H), 4.47 (s, 2H, NH 2), 2.26 (s, 3H, PhCH 3); MS (ESI) : m/z 495 [M+Na] +.
2) nthe preparation of-(the chloro-2-of 4-(2-((dimethylamine) methylene radical) acylhydrazone)-6-tolyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide (B2)
In 25 mL there-necked flasks, add respectively 3 (1 mmol), N, N-dimethylacetal (1.5 mol) and dehydrated alcohol (10 mL), reflux 1 hour, cooling dehydrated alcohol-DMF recrystallization for solid of separating out, obtains target compound II2.White solid, productive rate 85.7%, fusing point 163 ~ 164 oc; 1h NMR (DMSO-d 6): δ 10.59 (s, 1H, NH), 10.23 (s, 1H, NH), 8.65 (d, j=4.6 Hz, 1H, pyridine H), 8.44 (s, 1H, pyrazole H), 8.39 (d, j=8.0 Hz, 1H, pyridine H), 7.81-7.77 (m, 2H, pyridine H and benzene H), 7.52 (s, 1H, benzene H), 7.40 (s, 1H, N=CH), 2. 70 (s, 6H, N (CH 3) 2), 2.25 (s, 3H, PhCH 3); MS (ESI): m/z 528 [M+H] +, 550 [M+Na] +; Anal. Calcd (C 21h 18c l2f 3n 7o 2): C, 47.74; H, 3.43; N, 18.56. Found:C, 47.63; H, 3.25; N, 18.44.
Utilize similar synthetic method, synthesized other compound of the present invention, the proton nmr spectra of part of compounds ( 1h NMR) data, physico-chemical property and ultimate analysis data are as table 1shown in:
Table 1part of compounds fusing point, proton nmr spectra and results of elemental analyses
Numbering m. p. ( oC) 1H NMR ( 500 Hz, DMSO- d 6)/MS/ ultimate analysis
A1 239~240 δ 10.15 (s, 1H, NH), 8.35 (s, 1H, pyrazole H), 8.24 (s, 1H, benzene H),7.60-7.53 (m, 6H, benzene H), 7.39 (s, 1H, NH), 2.70 (s, 3H, NCH 3), 2.25 (s, 3H, PhCH 3); MS (ESI): m/z 437 [M+H] +, 459 [M+Na] +; Anal. Calcd (C 20H 16ClF 3N 4O 2): C, 54.99; H, 3.69; N, 12.83. Found: C, 54.85; H, 3.557; N, 12.64.
A3 247~249 δ 10.11 (s, 1H, NH), 8.40 (s, 1H, pyrazole H), 8.25 (s, 1H, benzene H),7.62-7.52 (m, 6H, benzene H), 7.37 (s, 1H, NH), 3.20 (q, J = 6.6 Hz, 2H, CH 2), 2.25 (s, 3H, PhCH 3), 1.06 (t, J = 7.2 Hz, 3H, CH 2CH 3); MS (ESI): m/z 451 [M+H] +, 473 [M+Na] +; Anal. Calcd (C 21H 18ClF 3N 4O 2): C, 55.95; H, 4.02; N, 12.43. Found: C, 55.57; H, 3.74; N, 12.06.
A4 232~234 δ 10.19 (s, 1H, NH), 8.66 (d, J = 4.6 Hz, 1H, pyridine H), 8.43 (s, 1H, pyrazole H), 8.40-8.39 (m, 2H, pyridine H and benzene CONH), 7.80 (m, 1H, pyridine H), 7.52 (s, 1H, benzene H), 7.38 (s, 1H, benzene H), 3.27-3.17 (m, 2H, CH 2), 2.27 (s, 3H, PhCH 3), 1.04 (t, J = 6.9 Hz, 3H, CH 3); MS (ESI): m/z 486 [M+H] +, 508 [M+Na] +; Anal. Calcd (C 20H 16C l2F 3N 5O 2): C, 49.40; H, 3.32; N, 14.40. Found: C, 49.29; H, 3.10; N, 14.24.
A5 >250 δ 10.11 (s, 1H, NH), 8.45 (s, 1H, pyrazole H), 8.26 (s, 1H, benzene H),7.61-7.51 (m, 6H, benzene H), 7.34 (s, 1H, NH), 2.73 (s, 1H, CH), 2.24 (s, 3H, PhCH 3), 0.63 (d, J = 5.2 Hz, 3H, CH 2), 0.51 (s, 2H, CH 2); MS (ESI): m/z 463 [M+H] +, 485 [M+Na] +; Anal. Calcd (C 22H 18ClF 3N 4O 2): C, 57.09; H, 3.92; N, 12.10. Found: C, 57.83; H, 3.79; N, 11.92.
A6 211~213 δ 10.14 (s, 1H, NH), 8.65 (d, J = 4.6 Hz, 1H, pyridine H), 8.44 (s, 1H, pyrazole H), 8.40-8.39 (m, 2H, pyridine H and benzene), 7.80 (m, 1H, pyridine H), 7.53 (s, 1H, benzene H), 7.36 (s, 1H, NH), 3.18-3.14 (m, 2H, CH 2), 2.26 (s, 3H, PhCH 3), 1.44-1.38 (m, 2H, CH 2), 1.29-1.22 (m, 2H, CH 2), 0.81 (t, J = 7.5 Hz, 3H, CH 3); MS (ESI): m/z 514 [M+H] +, 536 [M+Na] +; Anal. Calcd (C 22H 20C l2F 3N 5O 2): C, 51.37; H, 3.92; N, 13.62. Found: C, 51.18; H, 3.73; N, 13.55.
A7 203~205 δ 10.22 (s, 1H, NH), 8.17 (s, 1H, pyrazole H), 7.62-7.49 (m, 6H, benzene H), 7.29 (s, 1H, benzene H), 2. 92 (s, 1H, NCH 3), 2.81 (s, 3H, NCH 3), 2.25 (s, 3H, PhCH 3); MS (ESI): m/z 451 [M+H] +, 473 [M+Na] +; Anal. Calcd (C 21H 18ClF 3N 4O 2): C, 55.95; H, 4.02; N, 12.43. Found: C, 55.67; H, 3.74; N, 12.13.
A8 > 250 δ 10.19 (s, 1H, NH), 8.66 (d, J = 4.6 Hz, 1H, pyridine H), 8.45-8.41 (m, 2H, pyridine H and benzene),8.39 (s, 1H, pyrazole H), 7.82-7.80 (m, 1H, pyridine H), 7.53 (s, 1H, benzene H), 7.34 (s, 1H, NH), 2.73-2.70 (m, 1H, CH), 2.26 (s, 3H, PhCH 3), 0.64-0.59 (m, 2H, CH 2), 0.50-0.48 (m, 2H, CH 2); MS (ESI): m/z 498 [M+H] +, 520 [M+Na] +; Anal. Calcd (C 21H 16C l2F 3N 5O 2): C, 50.62; H, 3.24; N, 14.05. Found: C, 50.55; H, 3.01; N, 13.82.
A9 232~233 δ 10.07 (s, 1H, NH), 8.26 (s, 1H, pyrazole H), 7.68-7.52 (m, 6H, benzene H and PhCONH), 7.35 (s, 1H, benzene H), 2. 92 (s, 1H, NCH 3), 2.81 (s, 3H, NCH 3), 3.97 (m, 1H, CH), 2.25 (s, 3H, PhCH 3), 1.10 (s, 3H, CH 3), 1.08 (s, 3H, CH 3); MS (ESI): m/z 465 [M+H] +, 487 [M+Na] +; Anal. Calcd (C22H20ClF3N4O2): C, 56.84; H, 4.34; N, 12.05. Found: C, 56.51; H, 4.15; N, 11.82.
A10 234~235 δ 10.17 (s, 1H, NH), 8.66 (d, J = 4.6 Hz, 1H, pyridine H), 8.46 (s, 1H, pyrazole H), 8.39 (d, J = 8.0 Hz, 1H, benzene H), 8.23 (d, J = 7.5 Hz, 1H, pyridine H), 7.82-7.79 (m, 1H, pyridine H), 7.53 (s, 1H, benzene H), 7.35 (s, 1H, NH), 3.99-3.93 (m, 1H, CH), 2.27 (s, 3H, PhCH 3), 1.08 (s, 3H, CH 3), 1.07 (s, 3H, CH 3); MS (ESI): m/z 500 [M+H] +, 522 [M+Na] +; Anal. Calcd (C 21H 18C l2F 3N 5O 2): C, 50.41; H, 3.63; N, 14.00. Found: C, 50.25; H, 3.52; N, 13.87.
A11 237~238 δ 10.09 (s, 1H, NH), 8.39 (s, 1H, pyrazole H), 8.26 (s, 1H, NH),7.62-7.49 (m, 6H, benzene H), 7.36 (s, 1H, benzene H), 3.16 (d, 2H, J = 6.3, CH 2), 2.25 (s, 3H, PhCH 3), 1.43 (m , 2H, CH 2), 1.27 (m , 2H, CH 2), 0.81 (t, 3H, J = 7.2, CH 3); MS (ESI): m/z 479 [M+H] +, 501 [M+Na] +; Anal. Calcd (C 23H 22ClF 3N 4O 2): C, 57.68; H, 4.63; N, 11.70. Found: C, 57.52; H, 4.57; N, 11.55.
A12 190~192 δ 10.32 (s, 1H, NH), 8.66 (d, J = 4.6 Hz, 1H, pyridine H), 8.39 (m, 1H, pyridine H), 8.35 (s, 1H, pyrazole H), 7.82-7.80 (m, 1H, pyridine H), 7.49 (s, 1H, benzene H), 7.29 (s, 1H, NH), 2.91 (s, 3H, NCH 3), 2.81 (s, 3H, NCH 3), 2.27 (s, 3H, PhCH 3); MS (ESI): m/z 486 [M+H] +, 508 [M+Na] +; Anal. Calcd (C 20H 16C l2F 3N 5O 2): C, 49.40; H, 3.32; N, 14.40. Found: C, 49.33; H, 3.17; N, 14.36.
A13 241~242 δ 10.11 (s, 1H, NH), 8.5 (s, 1H, NH), 8.15 (s, 1H, pyrazole H), 7.62-7.55 (m, 6H, benzene H), 7.45 (s, 1H, benzene H), 7.31-7.20 (m, 5H, benzene H), 4.40 (s, 2H, CH 2), 2.25 (s, 3H, PhCH 3); MS (ESI): m/z 513 [M+H] +, 535 [M+Na] +; Anal. Calcd (C 26H 20ClF 3N 4O 2): C, 60.88; H, 3.93; N, 10.92. Found: C, 60.71; H, 3.86; N, 10.66.
A18 235~236 δ 10.22 (s, 1H, NH), 8.97 (d, J = 5.6 Hz, 1H, benzene H), 8.67 (d, J = 4.6 Hz, 1H, pyridine H), 8.39 (d, J = 8.0 Hz, 1H, benzene H), 8.34 (s, 1H, pyrazole H), 7.82-7.80 (m, 1H, pyridine H), 7.56 (s, 1H, NH), 7.45 (s, 1H, benzene H), 7.30-7.18 (m, 5H, benzne H), 4.39 (d, J = 6.3 Hz, 2H, NCH 2) 2.27 (s, 3H, PhCH 3); MS (ESI): m/z 548 [M+H] +, 570 [M+Na] +; Anal. Calcd (C 25H 18C l2F 3N 5O 2): C, 54.76; H, 3.31; N, 12.77. Found: C, 54.68; H, 3.25; N, 12.62.s
B1 234~236 δ 11.46 (s, 1H, NH), 10.15 (s, 1H, =CH), 8.22 (s, 1H, pyrazole H), 7.61-7.55 (m, 7H, benzene H), 7.44 (s, 1H, NH), 2.26-2.23 (m, 5H, CH 3 and CH 2), 1.02 (t, J = 7.5 Hz, 3H, CH 2CH 3); MS (ESI): m/z 478 [M+H] +, 500 [M+Na] +; Anal. Calcd (C 22H 19ClF 3N 5O 2): C, 55.29; H, 4.01; N, 14.66. Found: C, 54.86; H, 3.95; N, 14.23.
B3 223~225 δ 10.61 (s, 1H, NH), 10.14 (s, 1H, N=CH), 8.28 (s, 1H, pyrazole H), 7.77 (s, 1H, benzene H), 7.61-7.55 (m, 6H, benzene H), 7.39 (s, 1H, NH), 2.80 (s, 6H, N(CH 3) 2), 2.24 (s, 3H, PhCH 3); MS (ESI): m/z 493 [M+H] +, 515 [M+Na] +; Anal. Calcd (C 22H 20ClF 3N 6O 2): C, 53.61; H, 4.09 N, 17.05. Found: C, C, 53.43; H, 4.01 N, 16.88.
B4 131~132 δ 11.46 (s, 1H, NH), 10.26 (s, 1H, NH), 8.65 (d, J = 4.6 Hz, 1H, pyridine H), 8.40 (s, 1H, pyrazole H), 8.39 (s, 1H, benzene H), 7.82-7.79 (m, 1H, pyridine), 7.62-7.58 (m, 2H, benzene H and pyridine), 7.44 (d, J = 2.3 Hz, 1H, N=CH), 2.27- 2.23 (m, 5H, PhCH 3 and CH 2), 1.02 (t, J = 7.6 Hz, 3H, CH 3); MS (ESI): m/z 513 [M+H] +, 535 [M+Na] +; Anal. Calcd (C 21H 17Cl 2F 3N 6O 2): C, 49.14; H, 3.34; N, 16.37. Found: C, 48.86; H, 3.05; N, 16.21.
B5 199~200 δ 10.37 (s, 1H, NH), 10.16 (s, 1H, NH), 8.22 (s, 1H, pyrazole H), 7.62-7.45 (m, 7H, benzene H), 2.54 (s, 1H, CH), 2.26 (s, 3H, PhCH 3), 2.11 (d, J = 6.9 Hz, 2H, CH 2), 1.85(s, 3H, N=CCH 3), 0.86 (s, 3H, CH 3), 0.86 (s, 3H, CH 3); MS (ESI): m/z 520 [M+H] +, 542 [M+Na] +; Anal. Calcd (C 25H 25ClF 3N 5O 2): C, 57.75; H, 4.85; N, 13.47. Found: C, 57.53; H, 4.61; N, 13.29.
B6 105~107 δ 10.36 (s, 1H, NH), 8.65 (d, J = 4.6 Hz, 2H, pyridine H), 8.40 (s, 1H, pyrazole H), 7.83-7.79 (m, 2H, pyridine H and benzene), 7.57 (s, 1H, benzene H), 7.46 (s, 1H, NH), 2.27 (s, 3H, PhCH 3), 2.10 (d, J = 7.5 Hz, 2H, CH 2), 1.93 (s, 1H, CH), 1.82 (s, 3H, N=CCH 3), 0.89 (s, 3H, CH 3), 0.85 (s, 3H, CH 3); MS (ESI): m/z 555 [M+H] +, 577 [M+Na] +; Anal. Calcd (C 24H 23C l2F 3N 6O 2): C, 51.90; H, 4.17; N, 15.13. Found: C, 51.67; H, 4.02; N, 14.98.
biological activity test example
embodiment 3:biological activity test to small cabbage moth
With soak leaf feeding method measure [ agricultural chemicals, 1996, 35 (6): 37-39], fresh cabbage leaves is flooded to 10 s aftertreatment examination worms in liquid, examination worm is wanted hungry 5-6 hour before processing.Every concentration is processed 3 times and is repeated, and 10 examination worms of every repetition, take immersion solvent as contrast, and the examination worm after processing is put into the sincere moisturizing culture dish that has filter paper, and is placed in constant temperature raising in insectary, checks dead borer population in 72 h, and calculates insect population mortality ratio.As shown in table 2.
Calculate mortality ratio and corrected mortality:
(1)
In formula: P1-mortality ratio; K-dead borer population; The total borer population of N-process.
(2)
In formula: P2-corrected mortality; Pt-processing mortality ratio; P0-blank mortality ratio.If contrast mortality ratio < 5%, without correction; Contrast mortality ratio, between 5-20%, should be proofreaied and correct by formula (2); Contrast mortality ratio > 20%, test need be reformed.
Table 2the insecticidal activity (500 of part of compounds to small cabbage moth μg/mL)
Numbering Mortality ratio (%) Numbering Mortality ratio (%)
A1 100 A12 100
A2 93.8 A13 90.0
A3 100 A18 45.5
A4 100 B1 100
A5 78.6 B2 100
A6 85.7 B4 82.4
A7 100 B5 56.3
A10 100 B6 53.3
CK 0 Avrmectin 100
2can find out, this compounds is 500 μg/mL all shows good insecticidal activity to small cabbage moth, and benzamide compound shows good biological activity than benzoyl hydrazone compounds.If compd A 1, A3, A4, A7, A10, A12, B1 and B2 are 500 μunder the concentration of g/mL, the insecticidal activity of small cabbage moth is all reached to 100%.
embodiment 4:biological activity test to bollworm
Adopt the mixed medicine method of feed, from the solution configuring, pipette in the feed just having configured that 3 mL add approximately 27 grams, thereby obtain diluting the desired concn of ten times.After medicament mixes, pour into equably in 24 clean orifice plates, 24 bollworms of cool rear access of drying in the air, observe check result after 3-4 days.The calculation formula of mortality ratio is identical with formula described in embodiment 3.As shown in table 3.
Table 3the insecticidal activity (600 of part of compounds to bollworm μg/mL)
Mortality ratio (%) Numbering Mortality ratio (%)
A1 30 A10 85
A3 20 A11 30
A4 60 A18 60
A5 40 B1 40
A6 80 B3 20
A7 35 B4 50
A8 70 B5 40
A9 30 B6 35
CK 0 Poison slave girl with poison 100
From table 3can find out, this compounds is active to the certain inhibition of having of bollworm, and wherein compd A 6, A8 and A10 are 600 μunder the concentration of g/mL to the insecticidal activity of bollworm higher than 70%.
embodiment 5:biological activity test to Pyrausta nubilalis (Hubern).
Employing leaf dipping method ( j. Agric. Food Chem., 2004, 52 (22): 6737-6741), configure after desired concn, the blade of about 5-6 cm is soaked to into the liquid 5-6 second, take out, be placed on thieving paper and dry, be placed in the culture dish of appointment, access 10 3 instar larvaes, put into the insectary of 27 ± 1 ℃ and observe check result after 3-4 days.The calculation formula of mortality ratio is identical with formula described in embodiment 3.As shown in table 4.
Table 4the insecticidal activity (600 of part of compounds to Pyrausta nubilalis (Hubern). μg/mL)
Numbering Mortality ratio (%) Numbering Mortality ratio (%)
A2 60 A10 65
A4 100 A11 65
A6 40 A12 55
A7 80 A18 75
A8 45 B3 55
A9 60 B6 60
CK 0 Avrmectin 100
From table 4can find out, this compounds is 600 μunder the concentration of g/mL, Pyrausta nubilalis (Hubern). is shown to certain insecticidal activity, wherein the insecticidal activity of 4 pairs of Pyrausta nubilalis (Hubern).s of compd A reaches 100%.
embodiment 6:biological activity test to mythimna separata
Employing leaf dipping method ( j. Agric. Food Chem., 2004, 52 (22): 6737-6741), configure after desired concn, the blade of about 5-6 cm is soaked to into the liquid 5-6 second, take out, be placed on thieving paper and dry, be placed in the culture dish of appointment, access 10 3 instar larvaes, put into the insectary of 27 ± 1 ℃ and observe check result after 3-4 days.The calculation formula of mortality ratio is identical with formula described in embodiment 3.As shown in table 5.
The insecticidal activity (600 of table 5 part of compounds to mythimna separata μg/mL)
Numbering Mortality ratio (%) Numbering Mortality ratio (%)
A1 100 A8 100
A2 100 A9 80
A3 80 A10 100
A4 100 A12 60
A5 60 B3 50
A6 70 B4 60
A7 60 CK 0
From table 5can find out, this compounds shows good activity to mythimna separata.Wherein benzamide compound A1, A2, A4, A8 and A10 are 600 μinsecticidal activity to mythimna separata under the concentration of g/mL reaches 100%.
embodiment 7:biological activity test to northern house
Culex pipiens pallens, the normal population of indoor feeding.Experimental technique ( j. Agric. Food Chem.; 2007, 55 (7): 2659-2663): take test compound approximately 5 mg, add 5 mL acetone (or suitable solvent), vibration is dissolved, and is 1000 μ g/ mL mother liquor.Pipette 0.5 mL mother liquor, add in the 100 mL beakers that fill 89.9 ml waters, choose larvae at the beginning of 10 4 ages, together with 10 mL feeding liquids, pour in the lump in beaker, the concentration of its liquid is 5 μ g/mL.Processing is put into standard treatment chamber, 24 h check results.The aqueous solution that contains 0.5 mL test solvent of take is blank.The calculation formula of mortality ratio is identical with formula described in embodiment 3.As shown in table 6.
The insecticidal activity (10 of table 6 part of compounds to northern house μg/mL)
Numbering Mortality ratio (%) Numbering Mortality ratio (%)
A1 100 A11 100
A2 100 A12 100
A3 100 A13 100
A4 100 A18 100
A5 100 B1 100
A6 100 B3 100
A7 100 B4 100
A8 100 B5 100
A9 100 B6 100
A10 100 CK 0
From table 6can find out, this compounds shows good insecticidal activity to northern house, 10 μunder the concentration of g/mL, benzamide compound and benzoyl hydrazone compounds all show good insecticidal activity, and 14 benzamide compounds and 5 the benzoyl hydrazone compounds wherein tested are 100% to the insecticidal activity of northern house.

Claims (7)

1. a class is containing benzamide or the benzoyl hydrazone derivative of " 5-trifluoromethyl-4-pyrazole amide " structure, and compound structure is as shown in general formula A and B:
In formula:
R 1be selected from phenyl, 3-chloropyridine base;
R 2, R 3, R 4and R 5be selected from hydrogen atom, alkyl, heteroatom containing alkyl, phenyl, benzyl, heterocyclic radical, substituted heterocyclic radical.
2. compound according to claim 1, is characterized in that, the alkyl that described alkyl is C1-C4, the branched-chain alkyl of C1-C8.
3. compound according to claim 1, is characterized in that, described heterocyclic radical is pyridine cyclic group and furans cyclic group; The substituted heterocyclic radical of indication is pyridine methylene.
4. compound according to claim 1, is characterized by and be selected from following particular compound:
Numbering Compound title Structure A1 N-(4-chloro-2-methyl 6-(methylamino formyl) phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A2 N-(4-chloro-2-methyl-6-(methylamino formyl) phenyl)-1-(3-chloropyridine-2-yl))-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A3 N-(the chloro-2-of 4-(ethylamino formyl)-6-aminomethyl phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A4 N-(the chloro-2-of 4-(ethylamino formyl)-6-aminomethyl phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A5 N-(the chloro-2-of 4-(cyclopropylamino formyl)-6-aminomethyl phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A6 N-(the chloro-6-aminomethyl phenyl of 2-(butyl carbamyl)-4-)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A7 N-(the chloro-2-of 4-(dimethylamino formyl)-6-aminomethyl phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A8 N-(the chloro-2-of 4-(cyclopropylamino formyl)-6-aminomethyl phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A9 N-(the chloro-2-of 4-(isopropylamino formyl)-6-aminomethyl phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A10 N-(the chloro-2-of 4-(isopropylamino formyl)-6-aminomethyl phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A11 N-(the chloro-6-aminomethyl phenyl of 2-(butyl carbamyl)-4-)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A12 N-(the chloro-2-of 4-(dimethylamino formyl)-6-aminomethyl phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A13 N-(the chloro-6-aminomethyl phenyl of 2-(benzylamino formyl)-4-)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A14 N-(4-chloro-2-methyl-6-((6-methyl-2-heptane base) formamyl) phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A15 N-(4-chloro-2-methyl-6-((6-methyl-2-heptane base) formamyl) phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A16 N-(4-chloro-2-methyl--6-(carbanilino) phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A17 N-(4-chloro-2-methyl-6-((4-pyridine methylene) formamido-) phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide A18 N-(the chloro-6-aminomethyl phenyl of 2-(phenylcarbamoyl)-4-)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide B1 N-(4-chloro-2-methyl 6-(2-propylidene acylhydrazone) phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide B2 N-(the chloro-2-of 4-(2-((dimethylamine) methylene radical) acylhydrazone)-6-aminomethyl phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide B3 N-(the chloro-2-of 4-(2-((dimethylamine) methylene radical) acylhydrazone)-6-aminomethyl phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide B4 N-(4-chloro-2-methyl 6-(2-propylidene acylhydrazone) phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide B5 N-(4-chloro-2-methyl 6-(2-(4-methyl-isobutyl) acylhydrazone) phenyl)-1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide B6 N-(4-chloro-2-methyl 6-(2-(4-methyl-isobutyl) acylhydrazone) phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide B7 N-(4-chloro-2-methyl-6-(2-(3-pyridine methylene) acylhydrazone) phenyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide B8 N-(the chloro-6-tolyl of 2-(2-benzyl acylhydrazone)-4-)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide B9 N-(the chloro-2-of 4-(2-(furfurylidene) acylhydrazone)-6-tolyl)-1-(3-chloropyridine-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide
5. the class as described in claim 1 ~ 4 any one, containing " 5-trifluoromethyl-4-pyrazole amide " benzamide of structure or application of benzoyl hydrazone derivative, is characterized in that the application for the preparation of control Agricultural pests and sanitary insect pest aspect medicine and medicament aspect.
6. derivative according to claim 5 is in the medicine aspect control small cabbage moth, bollworm, Pyrausta nubilalis (Hubern)., mythimna separata and sanitary insect pest northern house or the application of medicament.
7. derivative according to claim 5, is characterized in that, in pesticide composition or in health deinsectization composition, and derivative content 0.000l wt%-99.9wt%, the composition outside derivative is agricultural, the acceptable diluent or carrier in health aspect.
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CN105198801A (en) * 2015-10-30 2015-12-30 武汉工程大学 N-(4-chloro-3-picolyl)-2-(3-methylbenzamide) benzamide as well as preparation method and application thereof
CN111848441A (en) * 2020-07-28 2020-10-30 朱翠萍 N-substituted benzoyl hydrazone compound and preparation method and application thereof
CN111848441B (en) * 2020-07-28 2023-02-17 山东中新科农生物科技有限公司 N-substituted benzoyl hydrazone compound and preparation method and application thereof

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