CN103833743B - Thiazolyl pyrazolyl acrylonitrile compound and application thereof - Google Patents
Thiazolyl pyrazolyl acrylonitrile compound and application thereof Download PDFInfo
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- CN103833743B CN103833743B CN201210483661.5A CN201210483661A CN103833743B CN 103833743 B CN103833743 B CN 103833743B CN 201210483661 A CN201210483661 A CN 201210483661A CN 103833743 B CN103833743 B CN 103833743B
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- 0 Cc1c(C(CCCI)=O)[s]c(*)n1 Chemical compound Cc1c(C(CCCI)=O)[s]c(*)n1 0.000 description 4
- IJNRBGYVKVGQMR-UHFFFAOYSA-N N#CCc(cc1)n[n]1-c1ccccc1 Chemical compound N#CCc(cc1)n[n]1-c1ccccc1 IJNRBGYVKVGQMR-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Abstract
The invention discloses thiazolyl pyrazolyl acrylonitrile compound or its stereoisomer of a kind of novel structure, compound structure is as shown in formula I:In formula: R is selected from C1‑C6Alkyl, halo C1‑C6Alkyl, C3‑C8Cycloalkyl, C1‑C6Alkoxyl or phenyl, benzene ring hydrogen also can be replaced by following substituent group further: halogen, cyano group, nitro, methyl or halogenated methyl；X is selected from chlorine, bromine or iodine.Compound of Formula I has the parasite killing of excellence, acaricidal activity, can be used for pest control, evil demodicid mite.
Description
Technical field
The invention belongs to Insecticidal and acaricidal agent field.Be specifically related to a kind of thiazolyl pyrazolyl acrylonitrile compound and
Application.
Background technology
Due to Insecticidal and acaricidal agent in use for some time, insect, evil demodicid mite can produce resistance to it, accordingly, it would be desirable to constantly
Invent tool parasite killing that is novel and that improve, the compound of acaricidal activity and compositions.Meanwhile, along with people are to days such as agricultural and animal products
The needs that benefit increases and the pay attention to day by day to environmental conservation, also have always a demand for use cost new killing lower, environment amenable
Worm, acaricide.
Nissan Chemical Ind Ltd, in WO9740009 applies for, discloses and has parasite killing, mite killing or bactericidal activity
The preparation of ethene derivatives and insecticidal activity thereof, numbering II-63 in compound K C(patent therein) compound is 500ppm's
Under concentration to the preventive effect of black peach aphid more than 80%.
In the prior art, thiazolyl pyrazolyl acrylonitrile compound as representative of the present invention and parasite killing, mite killing work
Property is not disclosed.
Summary of the invention
It is an object of the invention to provide the thiazolyl pyrazolyl acrylonitrile compound of a kind of novel structure, it can be applied
Insect, the preventing and treating of evil demodicid mite in the health of agricultural, forestry or non-treatment purpose.
Technical scheme is as follows:
The invention provides a kind of thiazolyl pyrazolyl acrylonitrile compound, as shown in formula I:
In formula:
R is selected from C1-C6Alkyl, halo C1-C6Alkyl, C3-C8Cycloalkyl, C1-C6Alkoxyl or phenyl, benzene ring hydrogen is also
Can be replaced by following substituent group further: halogen, cyano group, nitro, methyl or halogenated methyl；
X is selected from chlorine, bromine or iodine；
Or its stereoisomer.
The further preferred compound of the present invention is, in formula I:
R is selected from C1-C6Alkyl, halo C1-C6Alkyl, C3-C8Cycloalkyl, C1-C6Alkoxyl or phenyl；
X is selected from chlorine, bromine or iodine；
Or its stereoisomer.
The present invention further preferably compound is, in formula I:
R is selected from C3-C6Alkyl, halo C3-C6Alkyl or C1-C4Alkoxyl；
X is selected from chlorine；
Or its stereoisomer.
In the definition of compound of Formula I given above, collect term used and be typically defined as follows:
Alkyl refers to straight or branched form, such as methyl, ethyl, n-pro-pyl, isopropyl etc..Cycloalkyl includes ring third
Base, cyclobutyl, Cvclopropvlmethvl, methylcyclopropyl groups etc..Haloalkyl refers to the base that alkyl is optionally substituted with one or more halogen atoms
Group, such as chloroethyl, trifluoromethyl etc..Alkoxyl refers to that alkyl end is connected with the group of oxygen atom, such as methoxyl group, ethyoxyl,
Positive propoxy, isopropoxy etc..Halogen refers to fluorine, chlorine, bromine, iodine.Stereoisomer refers in Formulas I, taking on carbon-carbon double bond B
For base CN and OCOR in the same side (Z configuration) of B key or both sides (E).
The compound of Formula I of the present invention can be prepared by the following method, and in reaction equation, each group definition is the same.
In formula: L represents suitable leaving group, such as chlorine, bromine or tolysulfonyl epoxide etc..
Compounds of formula II and compound of formula III in suitable solvent, temperature be-10 DEG C to reaction under reflux temperature
0.5-48 hour prepared target compound I.
Suitable solvent is selected from dichloromethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetonitrile, tetrahydrochysene
Furan, dioxane, N,N-dimethylformamide or dimethyl sulfoxide etc..
Add suitable alkaloids favourable to reaction.Suitable alkali can be selected from organic base, such as triethylamine, N, N-bis-
Monomethylaniline., pyridine, Feldalat NM, sodium tert-butoxide or potassium tert-butoxide etc.；Or inorganic base such as sodium hydroxide, potassium hydroxide, bicarbonate
Sodium, sodium carbonate or sodium hydride etc..
Difference according to reaction condition or the difference of initiation material, there is stereo-isomerism in compound of Formula I.Such as carbon
Substituent group CN in carbon double bond B and OCOR1The same side (Z configuration) or both sides (E) at B key.By selecting suitable rising
Beginning raw material or control reaction condition, can obtain product or the individual isomer of a kind of isomer excess.Can also be by slightly
Product carries out the separation of conventional means, such as, by the method such as column chromatography, recrystallization, obtain individual isomer.These isomers
Structure can pass through X-ray single crystal diffraction, the conventional method of analysis such as nuclear magnetic resonance, NMR determines.
Compound of formula III is commercially available.
The preparation method of Compounds of formula II is as follows:
In formula: L1Represent suitable leaving group, such as chlorine, bromine, pyrazolyl, imidazole radicals, ester group or tolysulfonyl epoxide
Deng.
Compound of Formula IV and compounds of formula V in suitable solvent, in the presence of base, temperature be-10 DEG C to boiling
The lower 0.5-48 hour prepared general formula compound II of reaction of point.
Suitable solvent is mainly selected from: dichloromethane, chloroform, carbon tetrachloride, benzene, toluene, methanol, ethanol, ethyl acetate,
Acetonitrile, oxolane, dioxane, N,N-dimethylformamide, dimethyl sulfoxide, 2-methylpentane, methyl cyclopentane, oneself
Alkane, hexamethylene, hexahydrotoluene, heptane, octane, nonane, butyl ether, ethylene glycol dimethyl ether, ethylene glycol bisthioglycolate ethylether, ethylene glycol
Dibutyl ethers, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether etc., or as above two or three not
Mixture with solvent.
Add suitable alkaloids favourable to reaction.Suitable alkali is selected from organic base such as triethylamine, N, N-dimethyl benzene
Amine, pyridine, 2-picoline, 3-picoline, 4-picoline, aldehydecollidine, 2,3 dimethyl pyridine, 2,
4-lutidines, 3,5-lutidines, 2,6-lutidines, 2,4,6-trimethylpyridine, quinoline, Feldalat NM, ethanol
Sodium, sodium tert-butoxide or potassium tert-butoxide etc., or inorganic base such as sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate etc..
The preparation of compound of Formula IV sees the operational approach described in DE2633992.
The concrete preparation of compounds of formula V sees Tetrahedron Lett., and 2005,46,2251, J.Med.Chem.,
1973,16,978, US 6096898.
Table 1 lists structure and the physical property of partial Formula I.
Table 1
Part of compounds1H NMR(300MHz,CDCl3) data are as follows:
Compound 8:7.95 (d, 1H), 7.70 (m, 2H), 7.48 (m, 1H), 7.36 (m, 2H), 6.74 (d, 1H), 2.61
(s,3H),1.29(s,9H)。
Compound 9:7.96 (d, 1H), 7.69 (m, 2H), 7.47 (m, 1H), 7.35 (m, 2H), 6.77 (d, 1H), 2.63
(s,3H),1.65(q,2H),1.24(s,6H),0.79(t,3H)。
Compound 25:7.99 (d, 1H), 7.72 (m, 2H), 7.48 (m, 1H), 7.35 (m, 2H), 6.81 (d, 1H), 3.90
(s,3H),2.59(s,3H)。
The thiazolyl pyrazolyl acrylonitrile compound of the present invention has high parasite killing, acaricidal activity, can prevent and treat diamondback moth,
Beet armyworm, Prodenia litura, bollworm, meadow mythimna separata, cabbage looper, pea aphid, bean aphid, aphis fabae, cotten aphid, apple aphid, black peach aphid,
Corn leaf aphids, aleyrodid, leafhopper, plant hopper, planthopper, mealybug, web stinkbug, tomato bug, Nezara viridula smaragdula Fabricius., the smelly stinkbug of rice, cotton thrips, Herba Medicaginis Ji
The various pests such as horse, soybean thrip, colorado potato bug, click beetle, fly, mosquito, demodicid mite.Compared with known acrylonitrile compound, this
The thiazolyl pyrazolyl acrylonitrile compound of invention has beyond thought high parasite killing, acaricidal activity, especially has high killing
Aphid activity.Therefore, present invention additionally comprises compound of Formula I for controlling insect, the purposes of evil demodicid mite.
Present invention additionally comprises the insecticidal and acaricidal composition using compound of Formula I as active component.This parasite killing, mite killing group
In compound, the weight percentage of active component is between 1-99%.This insecticidal and acaricidal composition also includes agricultural, forestry or
Acceptable carrier in health.
The compositions of the present invention can be used with the form of preparation.Compound of Formula I is dissolved or dispersed in as active component
In carrier or be configured to preparation so that more readily dispersible when using as Insecticidal and acaricidal agent.Such as: these chemicals can be made
Become wettable powder or cream.In these compositionss, at least add a kind of liquid or solid carrier, and the most permissible
Add suitable surfactant.
Technical scheme also includes pest control, the method for evil demodicid mite: the insecticidal and acaricidal composition of the present invention executed
In needing on insect, evil demodicid mite or its somatomedin controlled.The more suitable effective amount being generally selected is that per hectare 10 grams arrives
1000 grams, preferably effective dose is per hectare 50 grams to 500 grams.
Some is applied, such as, agriculturally can add one or more in the insecticidal and acaricidal composition of the present invention
Other antibacterial, Insecticides (tech) & Herbicides (tech), plant growth regulator or fertilizer etc., thus can produce additional advantage and effect.
It should be appreciated that, in scope defined by the claims of the present invention, various conversion and change can be carried out.
Detailed description of the invention
Following synthesis example and raw result of the test of surveying can be used to further illustrate the present invention, but are not intended to limit this
Bright.
Synthetic example
Embodiment 1, the preparation of compound 8
(1) preparation of 3-methyl isophthalic acid-phenyl-1H-pyrazoles
Addition phenylhydrazine (5.00 grams, 0.046 mole) in reaction bulb, and 4,4-dimethoxy-2-butanones (7.30 grams, 0.055
Mole), ethanol 40 milliliters, it is warming up to backflow, refluxes 2 hours.In reactant liquor, drip concentrated hydrochloric acid (0.5 milliliter), continue backflow 2
Hour.Reaction is cooled to less than 30 DEG C after terminating, and reactant liquor is poured in 200 milliliters of water, extracts by 3 × 150 milliliters of ethyl acetate,
After gained organic facies is washed with saturated sodium-chloride water solution (150 milliliters), it is dried with anhydrous magnesium sulfate, after concentrating under reduced pressure, remaining
Thing obtains 5.00 grams of 3-methyl isophthalic acid-phenyl-1H-pyrazoles by pillar layer separation (leacheate: ethyl acetate: petroleum ether=1:10),
Yellow oil, yield 68%.
(2) preparation of 3-bromomethyl-1-phenyl-1H-pyrazoles
In reaction bulb, add 3-methyl isophthalic acid-phenyl-1H-pyrazoles (0.50 gram, 0.003 mole), toluene 5 milliliters, heat up
To 70 DEG C, add N-bromo-succinimide (0.40 gram, 0.003 mole), azodiisobutyronitrile (catalytic amount) to reactant liquor, add
Finishing, reactant liquor is warming up to backflow, back flow reaction 1 hour.Reaction is cooled to less than 30 DEG C after terminating, and reactant liquor is poured into 50 milliliters of water
In, with 3 × 50 milliliters of ethyl acetate extractions, gained organic facies saturated sodium bicarbonate aqueous solution (50 milliliters), saturated sodium-chloride
Aqueous solution (50 milliliters) washing after, be dried with anhydrous magnesium sulfate, after concentrating under reduced pressure, residue by pillar layer separation (leacheate:
Ethyl acetate: petroleum ether=1:100) obtain 0.40 gram of 3-bromomethyl-1-phenyl-1H-pyrazoles, yellow oil, yield 56%.
(3) preparation of 2-(1-phenyl-1H-pyrazole-3-yl) acetonitrile
3-bromomethyl-1-phenyl-1H-pyrazoles (0.55 gram, 0.003 mole), dimethyl sulfoxide 5 milli is added in reaction bulb
Rise, Cyanogran. (0.15 gram, 0.003 mole), room temperature reaction 6 hours.Reactant liquor is poured in 100 milliliters of water after terminating by reaction,
With 3 × 100 milliliters of ethyl acetate extractions, after gained organic facies is washed with saturated sodium-chloride water solution (100 milliliters), use anhydrous sulfur
Acid magnesium is dried, and after concentrating under reduced pressure, residue obtains 0.20 by pillar layer separation (leacheate: ethyl acetate: petroleum ether=1:20)
Gram 2-(1-phenyl-1H-pyrazole-3-yl) acetonitrile, yellow oil, yield 36%.
(4) system of 3-(2-chloro-4-methylthiazol-5-base)-3-hydroxyl-2-(1-phenyl-1H-pyrazole-3-yl) acrylonitrile
Standby
Under ice-water bath, (3.00 grams, 0.016 rubs acetonitrile to add 2-(1-phenyl-1H-pyrazole-3-yl) in reaction bulb
You), (2-chloro-4-methylthiazol-5-base) (1H-pyrazol-1-yl) ketone (4.33 grams, 0.019 mole), oxolane 40 milli
Rising, stir about 1 hour, be dividedly in some parts potassium tert-butoxide (3.59 grams, 0.032 mole), charging terminates, and reactant liquor is warming up to room temperature,
Room temperature reaction 6 hours.Reactant liquor is poured in 150 milliliters of water, and with 100 milliliters of ethyl acetate extractions, gained aqueous phase concentrated hydrochloric acid is adjusted
Acid to pH value is 2 ~ 3, with the extraction of 3 × 150 milliliters of ethyl acetate, organic facies through saturated sodium bicarbonate aqueous solution (150 milliliters), satisfy
After washing with sodium-chloride water solution (150 milliliters), it is dried with anhydrous magnesium sulfate, after concentration, obtains 2.70 grams of 3-(2-chloro-4-methyl thiazoliums
Azoles-5-base)-3-hydroxyl-2-(1-phenyl-1H-pyrazole-3-yl) acrylonitrile, yellow solid, yield 61%.
(5) preparation of compound 8
Under ice-water bath, in reaction bulb add 3-(2-chloro-4-methylthiazol-5-base)-3-hydroxyl-2-(1-phenyl-
1H-pyrazole-3-yl) acrylonitrile (0.34 gram, 0.001 mole), acetonitrile 5 milliliters, triethylamine (0.10 gram, 0.001 mole), then will
Pivalyl chloride (0.12 gram, 0.001 mole) is added drop-wise in reaction bulb, completion of dropwise addition, is warming up to be stirred at room temperature reaction 2 hours, instead
Liquid is answered to be poured in 50 milliliters of water, with ethyl acetate 100 milliliters extraction, gained organic facies saturated sodium bicarbonate aqueous solution (100 millis
Rise), saturated sodium-chloride water solution washing after (100 milliliters), be dried with anhydrous magnesium sulfate, after concentrating under reduced pressure, residue passes through post
Chromatographic isolation (leacheate: ethyl acetate: petroleum ether=1:15), obtains 0.15 g of compound 8, white solid, yield 38%.
Embodiment 2, the preparation of compound 9
Under ice-water bath, in reaction bulb add 3-(2-chloro-4-methylthiazol-5-base)-3-hydroxyl-2-(1-phenyl-
1H-pyrazole-3-yl) acrylonitrile (0.34 gram, 0.001 mole), acetonitrile 5 milliliters, triethylamine (0.10 gram, 0.001 mole), then will
2,2-dimethyl-butyrylchlorines (0.13 gram, 0.001 mole) are added drop-wise in reaction bulb, completion of dropwise addition, are warming up to reaction 2 is stirred at room temperature
Hour, reactant liquor is poured in 50 milliliters of water, and with ethyl acetate 100 milliliters extraction, gained organic facies saturated sodium bicarbonate water is molten
After the washing of liquid (100 milliliters), saturated sodium-chloride water solution (100 milliliters), it is dried with anhydrous magnesium sulfate, after concentrating under reduced pressure, remaining
Thing passes through pillar layer separation (leacheate: ethyl acetate: petroleum ether=1:15), obtains 0.20 g of compound 9, yellow solid, receives
Rate 45%.
Embodiment 3, the preparation of compound 29
Under ice-water bath, in reaction bulb add 3-(2-chloro-4-methylthiazol-5-base)-3-hydroxyl-2-(1-phenyl-
1H-pyrazole-3-yl) acrylonitrile (0.34 gram, 0.001 mole), acetonitrile 5 milliliters, triethylamine (0.10 gram, 0.001 mole), then will
Isobutyl chlorocarbonate (0.14 gram, 0.001 mole) is added drop-wise in reaction bulb, completion of dropwise addition, is warming up to that reaction 2 is stirred at room temperature little
Time, reactant liquor is poured in 50 milliliters of water, with ethyl acetate 100 milliliters extraction, gained organic facies saturated sodium bicarbonate aqueous solution
After the washing of (100 milliliters), saturated sodium-chloride water solution (100 milliliters), it is dried with anhydrous magnesium sulfate, after concentrating under reduced pressure, residue
By pillar layer separation (leacheate: ethyl acetate: petroleum ether=1:20), obtaining 0.20 g of compound 29 is one group of stereoisomerism
Body mixture (E:Z=3:2), yellow oil, yield 45%.
Biological activity determination
According to the dissolubility of testing compound, former medicinal acetone or dimethyl sulfoxide dissolve, then with 1 ‰ Tween 80 solution
Being configured to the liquid to be measured 50 milliliters of desired concn, acetone or dimethyl sulfoxide content in the solution is less than 10%.Parasite killing, mite killing
Mortality rate activity classification is as follows: A:100%；B:99%-80%；C:79%-60%；D:59%-0.
Embodiment 4, the mensuration of insecticidal activity
4.1 mensuration killing black peach aphid activity
Cut-off footpath 6 cm dishes, covers a metafiltration paper, and drips appropriate tap water moisturizing at the bottom of ware.From cultivating the sweet of black peach aphid
On blue plant, clip suitable size (diameter about 3 centimetres) and the long cabbage leaves having 15～30 aphids, remove alatae and leaf
The aphid in sheet front, after investigation radix, blade back is upwards placed in culture dish, carries out at spraying with hand-held Airbrush aerosol apparatus
Reason, pressure is that 10psi (is roughly equal to 0.7kg/cm2), spouting liquid is 0.5mL, often processes 3 times and repeats, processes and be placed on standard sight
Indoor, 48 hours " Invest, Then Investigate " survival borer populations, calculate mortality rate classification.
According to above method, partial test compound and the II-63 compound in known compound KC(WO9740009)
Carry out killing the parallel assay of black peach aphid activity.Result of the test is shown in Table 2.
Table 2: thiazolyl pyrazolyl acrylonitrile kills the parallel comparison of black peach aphid activity with known compound KC
4.2 kill the mensuration of diamondback moth activity
Cabbage leaves card punch breaking into the leaf dish of diameter 2 centimetres, uses Airbrush spraying treatment, pressure is 10psi
(it is roughly equal to 0.7kg/cm2), every leaf dish positive and negative is sprayed, and spouting liquid is 0.5mL.Often process to access after drying in the shade and try worm, often 10 2 ages
Process 3 repetitions.Put into 25 DEG C, relative humidity 60～70% after process and observe indoor cultivation, 72 hours " Invest, Then Investigate " survival borer populations,
Calculate mortality rate classification.
In the part compound for examination, following compounds is preferable to the prevention effect of diamondback moth when concentration is 600ppm,
Mortality rate reaches more than B level: 9.
The mensuration of 4.3 mythimna separates
Maize leaf being cut into the leaf section of long 2 centimetres, uses Airbrush spraying treatment, pressure is that 10psi (is roughly equal to 0.7kg/
cm2), every leaf section positive and negative is sprayed, and spouting liquid is 0.5mL.Often process to access after drying in the shade and try worm 10 2 ages, often process 3 weights
Multiple.Put into 25 DEG C, relative humidity 60～70% observation indoor cultivation, 72 hours " Invest, Then Investigate " survival borer populations after process, calculate mortality rate
And classification.
In the part compound for examination, following compounds is preferable, extremely to the prevention effect of mythimna separata when concentration is 600ppm
The rate of dying reaches more than B level: 8,25,28.
Embodiment 5, the mensuration of acaricidal activity
Tetranychus cinnabarinus is become the mensuration of demodicid mite activity
Assay method: take two panels true leaf Kidney bean Seedling, connects after Tetranychus cinnabarinus becomes demodicid mite and investigate radix, sprays with Airbrush
Device carries out whole strain spraying treatment, and pressure is that 10psi (is roughly equal to 0.7kg/cm2), spouting liquid is 0.5mL.Often process 3 times and repeat, place
Reason is placed on standard sight room, 72 hours " Invest, Then Investigate " survival demodicid mite numbers, calculates mortality rate classification.
In the part compound for examination, following compounds is preferable to the prevention effect of demodicid mite when concentration is 100ppm, dead
Rate reaches more than B level: 8,9,25,28,29.
In the part compound for examination, following compounds is preferable to the prevention effect of demodicid mite when concentration is 10ppm, mortality rate
Reach more than B level: 28.
Claims (5)
1. a thiazolyl pyrazolyl acrylonitrile compound, as shown in formula I:
In formula:
R is selected from the tert-butyl group, 2-methyl-2-butyl, methoxyl group, isopropoxy or isobutoxy；
X is selected from chlorine.
2. according to the compound described in claim 1, it is characterised in that in formula I:
R is selected from the tert-butyl group or 2-methyl-2-butyl；
X is selected from chlorine.
3. the purposes controlling aphid according to the compound of Formula I described in claim 1.
4. a killing aphids compositions, containing compound shown in formula I as claimed in claim 1 be active component and agricultural,
Acceptable carrier in forestry or health, in compositions, the weight percentage of active component is 1-99%.
5. the method controlling aphid, it is characterised in that: by the compositions described in claim 4 with per hectare 10 grams to 1000
Gram effective dose impose on need control aphid or its growth medium on.
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| CN1216530A (en) * | 1996-04-25 | 1999-05-12 | 日产化学工业株式会社 | Ethylene derivatives and pest controlling agents |
| CN101817784A (en) * | 1996-04-25 | 2010-09-01 | 日产化学工业株式会社 | Ethene derivatives and the pesticides that contains this derivative |
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