CN103833743A - Thiazolyl pyrazolyl acrylonitrile compound and application thereof - Google Patents
Thiazolyl pyrazolyl acrylonitrile compound and application thereof Download PDFInfo
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- CN103833743A CN103833743A CN201210483661.5A CN201210483661A CN103833743A CN 103833743 A CN103833743 A CN 103833743A CN 201210483661 A CN201210483661 A CN 201210483661A CN 103833743 A CN103833743 A CN 103833743A
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- 0 C=C(C1=**C(Cc2ccccc2)CC1)[Zn] Chemical compound C=C(C1=**C(Cc2ccccc2)CC1)[Zn] 0.000 description 2
- BRUZQRBVNRKLJG-UHFFFAOYSA-N CC(C)COC(N)=O Chemical compound CC(C)COC(N)=O BRUZQRBVNRKLJG-UHFFFAOYSA-N 0.000 description 1
- MXVQBODJJWZCMM-VLGSPTGOSA-N CCC(C)(C)C(O/C(/c([s]1)c(C)nc1Cl)=C(\c(cc1)n[n]1-c1ccccc1)/C#N)=O Chemical compound CCC(C)(C)C(O/C(/c([s]1)c(C)nc1Cl)=C(\c(cc1)n[n]1-c1ccccc1)/C#N)=O MXVQBODJJWZCMM-VLGSPTGOSA-N 0.000 description 1
Classifications
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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
-
- 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
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a thiazolyl pyrazolyl acrylonitrile compound or a stereisomer thereof with a novel structure. The structure of the compound is shown as the general formal in the specification, wherein R is one of alkyl of C1-C6, halogenated alkyl of C1-C6, cycloalkyl of C3-C8, alkoxy of C1-C6 and phenyl; hydrogen on a benzene ring can be further substituted by the following groups: halogen, cyano groups, nitro, methyl or halogenated methyl; X is one of chlorine, bromine or iodine. The compound in the general formula I has excellent insect and mite killing activity, and can be used for preventing and controlling insects and mites.
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 thereof.
Background technology
Due to Insecticidal and acaricidal agent in use for some time, insect, evil mite can produce resistance to it, therefore, need constantly invention novel with compound and the composition of improved tool desinsection, acaricidal activity.Meanwhile, along with people are to the growing needs such as agricultural and animal products and the pay attention to day by day to environment protection, also need lower, the environment amenable new Insecticidal and acaricidal agent of use cost always.
Nissan Chemical Ind Ltd is in WO9740009 application, disclose the preparation and the insecticidal activity thereof that there is desinsection, kill the ethene derivatives of mite or fungicidal activity, in compound K C(patent wherein, numbered II-63) compound under the concentration of 500ppm to the preventive effect of black peach aphid more than 80%.
In the prior art, as thiazolyl pyrazolyl acrylonitrile compound shown in the present and desinsection thereof, acaricidal activity have no open.
Summary of the invention
The object of the present invention is to provide a kind of thiazolyl pyrazolyl acrylonitrile compound of novel structure, it can be applicable to the control of insect in the health of agricultural, forestry or non-therapeutic purpose, evil mite.
Technical scheme of the present invention is as follows:
The invention provides a kind of thiazolyl pyrazolyl acrylonitrile compound, as shown in general formula I:
In formula:
R is selected from C
1-C
6alkyl, halo C
1-C
6alkyl, C
3-C
8cycloalkyl, C
1-C
6alkoxyl group or phenyl, benzene ring hydrogen also can further be replaced by following substituting group: halogen, cyano group, nitro, methyl or halogenated methyl;
X is selected from chlorine, bromine or iodine;
Or its steric isomer.
The further preferred compound of the present invention is, in general formula I:
R is selected from C
1-C
6alkyl, halo C
1-C
6alkyl, C
3-C
8cycloalkyl, C
1-C
6alkoxyl group or phenyl;
X is selected from chlorine, bromine or iodine;
Or its steric isomer.
The present invention further preferred compound is, in general formula I:
R is selected from C
3-C
6alkyl, halo C
3-C
6alkyl or C
1-C
4alkoxyl group;
X is selected from chlorine;
Or its steric isomer.
In the definition of the compound of Formula I providing, collect term General Definition used as follows above:
Alkyl refers to straight or branched form, such as methyl, ethyl, n-propyl, sec.-propyl etc.Cycloalkyl comprises cyclopropyl, cyclobutyl, cyclopropyl methyl, methyl cyclopropyl etc.Haloalkyl refers to the group that alkyl is replaced by one or more halogen atoms, as chloroethyl, trifluoromethyl etc.Alkoxyl group refers to that alkyl end is connected with the group of Sauerstoffatom, such as methoxyl group, oxyethyl group, positive propoxy, isopropoxy etc.Halogen refers to fluorine, chlorine, bromine, iodine.Steric isomer refers in formula I, and the substituting group CN on carbon-carbon double bond B and OCOR are in the same side of B key (Z configuration) or both sides (E configuration).
Compound of Formula I of the present invention can be prepared by the following method, and in reaction formula, each group definition is the same.
In formula: L represents suitable leavings group, as chlorine, bromine or tolysulfonyl oxygen base etc.
General formula I I compound with compound of formula III in suitable solvent, temperature makes target compound I for-10 DEG C for 0.5-48 hour to reacting under reflux temperature.
Suitable solvent is selected from methylene dichloride, chloroform, tetracol phenixin, hexane, benzene, toluene, ethyl acetate, acetonitrile, tetrahydrofuran (THF), dioxane, DMF or dimethyl sulfoxide (DMSO) etc.
Add suitable alkaloids to reacting favourable.Suitable alkali can be selected from organic bases, such as triethylamine, DMA, pyridine, sodium methylate, sodium tert-butoxide or potassium tert.-butoxide etc.; Or mineral alkali is as sodium hydroxide, potassium hydroxide, sodium bicarbonate, sodium carbonate or sodium hydride etc.
According to the difference of the difference of reaction conditions or starting raw material, there is steric isomerism in compound of Formula I.For example substituting group CN and the OCOR on carbon-carbon double bond B
1in the same side of B key (Z configuration) or both sides (E configuration).By selecting suitable starting raw material or controlling reaction conditions, can obtain the excessive product of a kind of isomer or individual isomer.Also can by crude product being carried out to the separation of conventional means, for example, by methods such as column chromatography, recrystallizations, obtain individual isomer.The structure of these isomer can be passed through X-ray single crystal diffraction, and the conventionals method of analysis such as nucleus magnetic resonance are determined.
Compound of formula III has commercially available.
The preparation method of general formula I I compound is as follows:
In formula: L
1represent suitable leavings group, as chlorine, bromine, pyrazolyl, imidazolyl, ester group or tolysulfonyl oxygen base etc.
General formula I V compound with general formula V compound in suitable solvent, under the existence of alkali, temperature makes general formula compound II for-10 DEG C for 0.5-48 hour to reacting under boiling point.
Suitable solvent is mainly selected from: methylene dichloride, chloroform, tetracol phenixin, benzene, toluene, methyl alcohol, ethanol, ethyl acetate, acetonitrile, tetrahydrofuran (THF), dioxane, N, dinethylformamide, dimethyl sulfoxide (DMSO), 2-methylpentane, methylcyclopentane, hexane, hexanaphthene, methylcyclohexane, heptane, octane, nonane, butyl ether, ethylene glycol dimethyl ether, ethylene glycol bisthioglycolate ethyl ether, ethylene glycol bisthioglycolate butyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether etc., or the as above mixture of two or three different solvents.
Add suitable alkaloids to reacting favourable.Suitable alkali is selected from organic bases as triethylamine, N, accelerine, pyridine, 2-picoline, 3-picoline, 4-picoline, aldehydecollidine, 2,3-lutidine, 2,4-lutidine, 3,5-lutidine, 2,6-lutidine, 2,4,6-trimethylpyridine, quinoline, sodium methylate, sodium ethylate, sodium tert-butoxide or potassium tert.-butoxide etc., or mineral alkali is as sodium hydroxide, potassium hydroxide, sodium carbonate or salt of wormwood etc.
The preparation of general formula I V compound is referring to the working method of describing in DE2633992.
The concrete preparation of general formula V compound is referring to Tetrahedron Lett., 2005,46,2251, J.Med.Chem., 1973,16,978, US 6096898.
Table 1 has been listed structure and the physical properties of part compound of Formula I.
Table 1
Part of compounds
1h NMR (300MHz, CDCl
3) 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).
Thiazolyl pyrazolyl acrylonitrile compound of the present invention has high desinsection, acaricidal activity, can prevent and treat the various pests such as small cabbage 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 fleahopper, Nezara viridula smaragdula Fabricius., the smelly stinkbug of rice, cotton thrips, alfalfa thrips, soya bean thrips, colorado potato bug, click beetle, fly, mosquito, mite.Compare with known acrylonitrile compound, thiazolyl pyrazolyl acrylonitrile compound of the present invention has beyond thought high desinsection, acaricidal activity, especially has high killing aphis activity.Therefore, the present invention also comprises the purposes of compound of Formula I for Control pests, evil mite.
The present invention also comprises desinsection, the miticide composition using compound of Formula I as active ingredient.In this desinsection, miticide composition, the weight percentage of active ingredient is between 1-99%.In this desinsection, miticide composition, also comprise acceptable carrier in agricultural, forestry or health.
Composition of the present invention can preparation form use.Compound of Formula I is easier to as solubilization of active ingredient or when being scattered in carrier or being mixed with preparation to using as Insecticidal and acaricidal agent disperse.For example: these chemicals can be made into wettable powder or missible oil.In these compositions, at least add a kind of liquid or solid carrier, and can add when needed suitable tensio-active agent.
Technical scheme of the present invention also comprises the method for pest control, evil mite: desinsection of the present invention, miticide composition are imposed on insect, evil mite or its growth medium of needs control.Conventionally the comparatively suitable significant quantity of selecting is 10 grams to 1000 grams of per hectares, and preferably significant quantity is 50 grams to 500 grams of per hectares.
For some application, for example in agricultural, can in desinsection of the present invention, miticide composition, add one or more other sterilant, Insecticides (tech) & Herbicides (tech), plant-growth regulator or fertilizer etc., can produce thus additional advantage and effect.
Should be clear and definite, in claim limited range of the present invention, can carry out various conversion and change.
Embodiment
Following synthetic example and the raw test-results of surveying can be used to further illustrate the present invention, but do not mean that restriction the present invention.
Synthetic example
The preparation of embodiment 1, compound 8
(1) preparation of 3-methyl isophthalic acid-phenyl-1H-pyrazoles
In reaction flask, add phenylhydrazine (5.00 grams, 0.046 mole), 4,4-dimethoxy-2-butanone (7.30 grams, 0.055 mole), 40 milliliters of ethanol, are warming up to backflow, reflux 2 hours.In reaction solution, drip concentrated hydrochloric acid (0.5 milliliter), continue to reflux 2 hours.After finishing, reaction is cooled to below 30 DEG C, in reaction solution impouring 200 ml waters, with 3 × 150 milliliters of ethyl acetate extractions, gained is for organic phase after saturated sodium-chloride water solution (150 milliliters) washing, with anhydrous magnesium sulfate drying, after concentrating under reduced pressure, resistates separates (leacheate: ethyl acetate: sherwood oil=1:10) by column chromatography and obtains 5.00 grams of 3-methyl isophthalic acid-phenyl-1H-pyrazoles, yellow oil, yield 68%.
(2) preparation of 3-brooethyl-1-phenyl-1H-pyrazoles
In reaction flask, add (0.50 gram of 3-methyl isophthalic acid-phenyl-1H-pyrazoles, 0.003 mole), 5 milliliters of toluene, be warming up to 70 DEG C, add N-bromo-succinimide (0.40 gram, 0.003 mole) to reaction solution, Diisopropyl azodicarboxylate (catalytic amount), finish, reaction solution is warming up to backflow, back flow reaction 1 hour.After finishing, reaction is cooled to below 30 DEG C, in reaction solution impouring 50 ml waters, with 3 × 50 milliliters of ethyl acetate extractions, after gained saturated sodium bicarbonate aqueous solution (50 milliliters) for organic phase, saturated sodium-chloride water solution (50 milliliters) washing, with anhydrous magnesium sulfate drying, after concentrating under reduced pressure, resistates separates (leacheate: ethyl acetate: sherwood oil=1:100) by column chromatography and obtains 0.40 gram of 3-brooethyl-1-phenyl-1H-pyrazoles, yellow oil, yield 56%.
(3) preparation of 2-(1-phenyl-1H-pyrazole-3-yl) acetonitrile
In reaction flask, add 3-brooethyl-1-phenyl-1H-pyrazoles (0.55 gram, 0.003 mole), 5 milliliters of dimethyl sulfoxide (DMSO), sodium cyanide (0.15 gram, 0.003 mole), room temperature reaction 6 hours.Reaction finish after by reaction solution impouring 100 ml waters, with 3 × 100 milliliters of ethyl acetate extractions, gained is for organic phase after saturated sodium-chloride water solution (100 milliliters) washing, with anhydrous magnesium sulfate drying, after concentrating under reduced pressure, resistates separates (leacheate: ethyl acetate: sherwood oil=1:20) by column chromatography and obtains 0.20 gram of 2-(1-phenyl-1H-pyrazole-3-yl) acetonitrile, yellow oil, yield 36%.
(4) preparation of 3-(the chloro-4-methylthiazol-5-of 2-yl)-3-hydroxyl-2-(1-phenyl-1H-pyrazole-3-yl) vinyl cyanide
Under ice-water bath, in reaction flask, add 2-(1-phenyl-1H-pyrazole-3-yl) acetonitrile (3.00 grams, 0.016 mole), (4.33 grams of (the chloro-4-methylthiazol-5-of 2-yl) (1H-pyrazol-1-yl) ketones, 0.019 mole), 40 milliliters of tetrahydrofuran (THF)s, stir about 1 hour adds (3.59 grams of potassium tert.-butoxides in batches, 0.032 mole), reinforced end, reaction solution is warming up to room temperature, room temperature reaction 6 hours.In reaction solution impouring 150 ml waters, with 100 milliliters of ethyl acetate extractions, gained water is 2 ~ 3 by concentrated hydrochloric acid acid adjustment to pH value, with 3 × 150 milliliters of ethyl acetate extractions, organic phase is after saturated sodium bicarbonate aqueous solution (150 milliliters), saturated sodium-chloride water solution (150 milliliters) washing, with anhydrous magnesium sulfate drying, after concentrated, obtain 2.70 grams of 3-(the chloro-4-methylthiazol-5-of 2-yl)-3-hydroxyl-2-(1-phenyl-1H-pyrazole-3-yl) vinyl cyanide, yellow solid, yield 61%.
(5) preparation of compound 8
Under ice-water bath, in reaction flask, add (0.34 gram of 3-(the chloro-4-methylthiazol-5-of 2-yl)-3-hydroxyl-2-(1-phenyl-1H-pyrazole-3-yl) vinyl cyanide, 0.001 mole), 5 milliliters of acetonitriles, (0.10 gram of triethylamine, 0.001 mole), again by (0.12 gram of pivalyl chloride, 0.001 mole) be added drop-wise in reaction flask, drip and finish, be warming up to stirring at room temperature reaction 2 hours, in reaction solution impouring 50 ml waters, with 100 milliliters of extractions of ethyl acetate, gained is saturated sodium bicarbonate aqueous solution (100 milliliters) for organic phase, after saturated sodium-chloride water solution washing (100 milliliters), with anhydrous magnesium sulfate drying, after concentrating under reduced pressure, resistates separates (leacheate: ethyl acetate: sherwood oil=1:15) by column chromatography, obtain 0.15 and digest compound 8, white solid, yield 38%.
The preparation of embodiment 2, compound 9
Under ice-water bath, in reaction flask, add (0.34 gram of 3-(the chloro-4-methylthiazol-5-of 2-yl)-3-hydroxyl-2-(1-phenyl-1H-pyrazole-3-yl) vinyl cyanide, 0.001 mole), 5 milliliters of acetonitriles, (0.10 gram of triethylamine, 0.001 mole), again by 2, (0.13 gram of 2-dimethyl-butyrylchlorine, 0.001 mole) be added drop-wise in reaction flask, drip and finish, be warming up to stirring at room temperature reaction 2 hours, in reaction solution impouring 50 ml waters, with 100 milliliters of extractions of ethyl acetate, gained is saturated sodium bicarbonate aqueous solution (100 milliliters) for organic phase, after saturated sodium-chloride water solution washing (100 milliliters), with anhydrous magnesium sulfate drying, after concentrating under reduced pressure, resistates separates (leacheate: ethyl acetate: sherwood oil=1:15) by column chromatography, obtain 0.20 and digest compound 9, yellow solid, yield 45%.
The preparation of embodiment 3, compound 29
Under ice-water bath, in reaction flask, add (0.34 gram of 3-(the chloro-4-methylthiazol-5-of 2-yl)-3-hydroxyl-2-(1-phenyl-1H-pyrazole-3-yl) vinyl cyanide, 0.001 mole), 5 milliliters of acetonitriles, (0.10 gram of triethylamine, 0.001 mole), again by (0.14 gram of isobutyl chlorocarbonate, 0.001 mole) be added drop-wise in reaction flask, drip and finish, be warming up to stirring at room temperature reaction 2 hours, in reaction solution impouring 50 ml waters, with 100 milliliters of extractions of ethyl acetate, gained is saturated sodium bicarbonate aqueous solution (100 milliliters) for organic phase, after saturated sodium-chloride water solution washing (100 milliliters), with anhydrous magnesium sulfate drying, after concentrating under reduced pressure, resistates separates (leacheate: ethyl acetate: sherwood oil=1:20) by column chromatography, obtaining 0.20, to digest compound 29 be one group of stereoisomer mixture (E:Z=3:2), yellow oil, yield 45%.
Biological activity determination
According to the solvability of testing compound, former medicinal acetone or methyl-sulphoxide dissolve, and then become 50 milliliters of the liquid to be measured of desired concn with 1 ‰ tween 80 solution preparation, and acetone or the methyl-sulphoxide content in solution is no more than 10%.Desinsection, to kill the active classification of mite mortality ratio as follows: A:100%; B:99%-80%; C:79%-60%; D:59%-0.
The mensuration of embodiment 4, insecticidal activity
4.1 kill the mensuration of black peach aphid activity
6 centimetres, cut-off footpath culture dish, covers one deck filter paper at the bottom of ware, and drips appropriate tap water moisturizing.Clip suitable size (3 centimetres of diameters) and the long cabbage leaves that has 15～30 aphids from the cabbage plant of cultivation black peach aphid, remove the aphid of alatae and face of blade, after investigation radix, blade back is upwards placed in culture dish, with the processing of spraying of hand-held Airbrush atomizer, pressure is that 10psi (is roughly equal to 0.7kg/cm
2), spouting liquid is 0.5mL, and every processing repeats for 3 times, processes and is placed in standard observation ward, and 48 hours " Invest, Then Investigate " survival borer populations, calculate mortality ratio classification.
According to above method, the II-63 compound in partial test compound and known compound KC(WO9740009) carry out killing the replicate(determination) of black peach aphid activity.Test-results is in table 2.
Table 2: thiazolyl pyrazolyl acrylonitrile and known compound KC kill the parallel comparison of black peach aphid activity
4.2 kill the mensuration of small cabbage moth activity
Cabbage leaves is broken into the leaf dish of 2 centimetres of diameters with punch tool, process with Airbrush spraying, pressure is that 10psi (is roughly equal to 0.7kg/cm
2), every leaf dish pros and cons spraying, spouting liquid is 0.5mL.After drying in the shade, every processing access tries worm 10 2 ages, and every processing repeats for 3 times.After processing, put into 25 DEG C, relative humidity 60～70% observation indoor cultivation, 72 hours " Invest, Then Investigate " survival borer populations, calculate mortality ratio classification.
In the compound of part for examination, following compounds prevention effect to small cabbage moth in the time that concentration is 600ppm is better, more than mortality ratio reaches B level: 9.
The mensuration of 4.3 mythimna separates
Maize leaf is cut into the leaf section of long 2 centimetres, processes with Airbrush spraying, pressure is that 10psi (is roughly equal to 0.7kg/cm
2), every leaf section pros and cons spraying, spouting liquid is 0.5mL.After drying in the shade, every processing access tries worm 10 2 ages, and every processing repeats for 3 times.After processing, put into 25 DEG C, relative humidity 60～70% observation indoor cultivation, 72 hours " Invest, Then Investigate " survival borer populations, calculate mortality ratio classification.
In the compound of part for examination, following compounds prevention effect to mythimna separata in the time that concentration is 600ppm is better, more than mortality ratio reaches B level: 8,25,28.
The mensuration of embodiment 5, acaricidal activity
Carmine spider mite is become to the mensuration of mite activity
Measuring method: get two true leaf Kidney bean seedlings, connect carmine spider mite and become mite and investigate after radix, carry out whole strain spraying process with Airbrush atomizer, pressure is that 10psi (is roughly equal to 0.7kg/cm
2), spouting liquid is 0.5mL.Every processing repeats for 3 times, processes and is placed on standard observation ward, and 72 hours " Invest, Then Investigate " survival mite numbers, calculate mortality ratio classification.
In the compound of part for examination, following compounds prevention effect to mite in the time that concentration is 100ppm is better, more than mortality ratio reaches B level: 8,9,25,28,29.
In the compound of part for examination, following compounds prevention effect to mite in the time that concentration is 10ppm is better, more than mortality ratio reaches B level: 28.
Claims (6)
1. a thiazolyl pyrazolyl acrylonitrile compound, as shown in general formula I:
In formula:
R is selected from C
1-C
6alkyl, halo C
1-C
6alkyl, C
3-C
8cycloalkyl, C
1-C
6alkoxyl group or phenyl, benzene ring hydrogen also can further be replaced by following substituting group: halogen, cyano group, nitro, methyl or halogenated methyl;
X is selected from chlorine, bromine or iodine;
Or its steric isomer.
2. according to compound claimed in claim 1, it is characterized in that, in general formula I:
R is selected from C
1-C
6alkyl, halo C
1-C
6alkyl, C
3-C
8cycloalkyl, C
1-C
6alkoxyl group or phenyl;
X is selected from chlorine, bromine or iodine;
Or its steric isomer.
3. according to compound claimed in claim 2, it is characterized in that, in general formula I:
R
1be selected from C
3-C
6alkyl, halo C
3-C
6alkyl or C
1-C
4alkoxyl group;
X is selected from chlorine;
Or its steric isomer.
One kind according to compound of Formula I Control pests claimed in claim 1, evil mite purposes.
5. desinsection, a miticide composition, containing compound shown in general formula I as claimed in claim 1 is acceptable carrier in active ingredient and agricultural, forestry or health, in composition, the weight percentage of active ingredient is 1-99%.
6. a method for Control pests, evil mite, is characterized in that: composition claimed in claim 5 is imposed on the medium of insect, evil mite or its growth of needs control with the effective dose of 10 grams to 1000 grams of per hectares.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106187936A (en) * | 2015-05-07 | 2016-12-07 | 湖南化工研究院有限公司 | Acrylonitrile compound and application thereof |
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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 |
| WO2007100160A1 (en) * | 2006-03-03 | 2007-09-07 | Nissan Chemical Industries, Ltd. | Acrylonitrile compounds |
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2012
- 2012-11-23 CN CN201210483661.5A patent/CN103833743B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2007100160A1 (en) * | 2006-03-03 | 2007-09-07 | Nissan Chemical Industries, Ltd. | Acrylonitrile compounds |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106187936A (en) * | 2015-05-07 | 2016-12-07 | 湖南化工研究院有限公司 | Acrylonitrile compound and application thereof |
| CN106187936B (en) * | 2015-05-07 | 2018-08-03 | 湖南化工研究院有限公司 | Acrylonitrile compound and application thereof |
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| CN103833743B (en) | 2016-12-21 |
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