CN1183409A - Insecticidal acaricidal pyrazoles compounds and preparation thereof - Google Patents

Insecticidal acaricidal pyrazoles compounds and preparation thereof Download PDF

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CN1183409A
CN1183409A CN 95115410 CN95115410A CN1183409A CN 1183409 A CN1183409 A CN 1183409A CN 95115410 CN95115410 CN 95115410 CN 95115410 A CN95115410 A CN 95115410A CN 1183409 A CN1183409 A CN 1183409A
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replacement
alkyl
phenyl
sulphur
cycloalkyl
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CN1055083C (en
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李宗成
刘长令
雷新
范登进
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Shenyang Research Institute of Chemical Industry Co Ltd
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Abstract

A pyrazoles compound is disclosed, which can be used as insecticide and acaricide to kill the pests and mite on animal body or plant.

Description

The pyrazole compound and the preparation thereof that are used for Insecticiding-miticiding
Belong to agricultural insecticide.Pyrazole compound general formula of the present invention is:
In the formula:
R 1Be alkyl, haloalkyl, cycloalkyl, (replacement) phenyl, (replacement) pyridine, (replacement) pyrimidine, (replacement) naphthyl.R 2, R 3Can be identical or different, can be hydrogen, halogen, alkyl, cyano group, nitro, haloalkyl, alkoxyl group, alkylthio, (replacement) benzene (oxygen or sulphur) base, (replacement) naphthalene (oxygen or sulphur) base, (replacement) pyridine (oxygen or sulphur) base, (replacement) pyrimidine (oxygen or sulphur) base.R 4Be hydrogen, alkyl, (replacement) aminocarboxyl, carbalkoxy, alkoxyalkyl, (replacement) allyl group, (replacement) propargyl.Q is Q 1Or Q 2
R 5Be hydrogen, alkyl, alkoxyalkyl, alkyl-carbonyl, alkoxy carbonyl, (replacement) aminocarboxyl, (replacement) allyl group, (replacement) propargyl, (replacement) cycloalkyl, (replacement) phenyl, alkoxyl group, (replacement) phenyl, (replacement) pyridyl, (replacement) pyrimidyl.
R 6Be alkyl, (replacement) cycloalkyl, (replacement) phenyl, (replacement) naphthyl, (replacement) pyridyl, (replacement) pyrimidyl, (replacement) thiazolyl, (replacement) amido and A 1～A 30Shown substituting group.
Figure A9511541000101
X is oxygen, sulphur, NNO 2, CHNO 2, NCN, NR 8
ZR 7Be SR 6Or R 9R 9Be (replacement) pyrazoles, (replacement) imidazoles, (replacement) triazole, (replacement) pyridine amido, (replacement) pyrimidine amido, (replacement) anilino, (replacement) naphthylamine base.
R 8Be alkyl, (replacement) phenyl, (replacement) pyridyl, (replacement) pyrimidyl.
When Q is Q 1The time, R 4And R 5Can form five yuan or six-ring, R 5And R 8Also can form five yuan or six-ring, as (replacement) pyrazoles, (replacement) imidazoles, (replacement) triazole, (replacement) pyridazine, (replacement) pyrroles.
R 2, R 3And In the position of pyrazoles ring, respectively can be in 3,4,5 any one position, but be preferably R 2At 3, R 3At 5, At 4.
More than said alkyl be often referred to the C of any replacement 1～8Straight or branched alkyl, substituted alkyl can be the alkyl of cyano group, nitro, halogen, alkoxyl group, carbonyl, phenyl, naphthyl substituted, and cycloalkyl refers to C 3～6Cycloalkyl.
The intermediate synthetic method 74:99668 of pyrazole compound of the present invention, Ger (East), 74,030,1970.6.20 5PP, 60:1747f Bul1.chem.Soc.Japan, the existing report of 36 (9) 1214-20 (1963), compound of the present invention (I) adopt following method preparation:
Method 1:
Figure A9511541000111
Reaction be inert solvent as, ethylene dichloride, chloroform, methylene dichloride, tetracol phenixin, benzene, toluene, dimethylbenzene, chlorobenzene, dichlorobenzene, ether, isopropyl ether, methyl alcohol, ethanol, tetrahydrofuran (THF), acetone, dimethyl formamide, dimethyl sulfoxide (DMSO), dioxane, acetonitrile, one of in the water or in the two or more mixed solvents with triethylamine, pyridine, sodium hydroxide (potassium), anhydrous sodium carbonate (potassium), Tetrabutyl amonium bromide, triethylene diamine, the 4-Dimethylamino pyridine, 1,8-diazacyclo [5,4,0]-react under the existence such as hendecene-7 catalyzer, temperature of reaction is-10 a ℃～solvent boiling point temperature, reaction times is 0.1～48 hour, gets product (I):
Method 2:
Figure A9511541000112
Method 3:(works as R 4During=H)
(work as R 4=H Time)
Figure A9511541000121
Method 4:
Figure A9511541000122
Method 5:
Figure A9511541000131
Method 2-5 is identical with the preparation condition of method I.
Further illustrate the present invention for example below, but be not limited to the present invention.
Example I
The preparation of 1-(5-chloro-1,3-dimethyl-pyrazoles-4-formyl radical)-3-(naphthalene-1-yl) urea:
With 30 gram 5-chloro-1; 3-dimethyl-pyrazole-4-carboxamide is dissolved in 80 milliliters of ethylene dichloride; carry out back flow reaction with 32 gram oxalyl chlorides then; till no gas evolution (3～24 hours); slough unreacted oxalyl chloride; underpressure distillation divides 27.6 grams (colourless liquid), yield 80.0%, i.e. acyl isocyanate.
Acyl isocyanate 1.0 grams that make are splashed in 10 milliliters of ethylene dichloride that are dissolved with 0.8 gram naphthalidine, and stirring at room 30 minutes is filtered, and ether is washed, and is dry that white solid (being title compound) 1.6 restrains yield 93.2%, 193～194 ℃ of fusing points.Measure through nuclear-magnetism, 1HNMR (interior mark TMS, DMSO) 8 (PPM): 11.52 (bs, 1H), 10.53 (bs, 1H), 3.29～9.40 (m, 6H), 3.30 (5.3H), 2.39 (5.3H).
Example 2:
1,5-dimethyl-1-[(5-chloro-1,3-dimethyl-pyrazole-4-carboxamide base) carbonyl] preparation of pyrazoles
0.8 gram 3 is dissolved in 10 milliliters of methylene dichloride, splashes into the acyl isocyanate that 1.5 grams make by example 1 method then; exothermic heat of reaction, stirring at room reaction 30 minutes is filtered; dry that title compound (I) 2.1 restrains, yield 94.6%, fusing point are 171～173 °.
Example 3:
1-[3,5-two chloro-4-(4-nitrophenoxy) phenyl]-preparation of 3-(5-chloro-1,3-dimethyl-pyrazoles-4-formyl radical) thiocarbamide.
With 2 gram 5-chloro-1,3-dimethyl-pyrazoles-4-formyl chloride is dissolved in 10 milliliters of acetone, adds NH 4SCN 0.9 gram, back flow reaction 2 hours, filtration then, the solution that will contain the sulfo-isocyanide ester is with 3 of 3,0 grams, and 5-two chloro-4-(4-nitrophenoxy) aniline are put in the reaction flask, back flow reaction 2 hours, filter, drying gets title compound (I) 4.5 grams, two step yields 87.5%, 219～220 ℃ of fusing points.
1HNMR (interior mark TMS, DMSO)
δ(PPM)：
10、81(bs，1H)，10.50(bs，1H)
8.28(d，2H)??8.00(s，2H)
7.10(d，2H)3.69(s，3H)
2.33(s，3H)
Institute's synthetic compound I that sees attached list
Title compound of the present invention (I) can be used alone as sterilant also can be made into binary or the mixture more than the binary with known insecticides or sterilant.The known insecticidal/acaricidal agent that can be mixed has: Chlorpyrifos 94, thiophos, Volaton, methomyl, carbofuran, Cypermethrin, fenvalerate, Provado, CGA106630, RI15992, Ni-25, Fipronil, triaxamate, azoles mite ester, pyrrole leech amine, 8801, pyridaben, four mite piperazines, Y1-5361, S21 121 and benzoyl area kind, the pyroles insecticidal/acaricidal agent, as AC30363, the sterilant that can be mixed has: metaxanin, dislike acid amides, M 9834, dimethomorph, fenpiclonil, mepanipyrim, nitrile bacterium azoles, BAS480F, BAS490F, ICIA5504, Mon24000, XRD-563, Pyrimothanil, CGA219417, ferimzone.Title compound of the present invention (I) can be made into emulsion, pulvis, wettable powder, granule, suspension concentrate application, and the content of compound (I) in preparation is 1%～99%.
Used solvent has aliphatic hydrocarbon and aromatic hydrocarbon in the emulsion, as benzene,toluene,xylene, pimelinketone, isophorone, methyl-sulphoxide, dimethyl formamide, mineral oil, vegetables oil.
Powder system, wettable powder, used carrier and the tensio-active agent of granule have: silica gel, talcum powder, kaolin, silicon oxide, silicon bentonite, calcium lignin sulphonate, polyoxyethylene alkyl phenyl ether, naphthene sulfonic acid and salt thereof, formaldehyde condensation products, fatty alcohol sulfate, substituted benzenesulfonic acid and salt thereof.
Example 4
In the title compound (I) any one 10 parts, polyoxyethylene vinylbenzene ether 14,6 parts of calcium dodecylbenzene sulphonates, 35 parts of dimethylbenzene, 35 parts of dimethyl formamides (weight percentage), thorough mixing makes emulsion.
Example 5
In the title compound (I) any one 10 parts, 80 parts of kaolin, 10 parts of talcum powder (weight percentage), thorough mixing makes pulvis.
Example 6
In the title compound (I) any one 10 parts, 5 parts of calcium lignin sulphonates, 7 parts of sodium lauryl sulfates, synthetic oxidizing aqueous silicon 78 parts (weight percentage) are fully pulverized mixed wettable powder.
Example 7
In the title compound (I) any one 5 parts, 1 part of synthetic oxidizing aqueous silicon, 2 parts of calcium lignin sulphonates, 30 parts of bentonite, 62 parts of kaolin (weight percentage) are fully pulverized and are mixed, and add water and stir, and granulation, drying make granule.
Example 8
In the title compound (I) any one 5 parts, 5 parts of the formaldehyde condensation products of sodium naphthalene sulfonate, 85 parts in water (weight percentage) behind the thorough mixing, adds 5 parts of tackiness agent methylcellulose gum, make suspension concentrate,
Title compound of the present invention (I) has desinsection and acaricidal activity, be used to prevent and treat insect and mite class on domestic animal and the plant materials, to small cabbage moth, mythimna separata, Heliothis virescens, bollworm, housefly, wild cabbage root flowerfly, aphid, leafhopper, Groton bug, two-spotted spider mite, carmine spider mite have special efficacy.
It is as follows to give birth to test proved recipe method:
1, to the test of black bean aphid
With title compound (I), be 250PPM with concentration, be 3 day age for the examination black bean aphid, the each processing tried 50～100 of worms, and with the clear water contrast, triplicate is placed on after the processing in 20～23 ℃ of observation ward, and 24 hours " Invest, Then Investigate " mortality ratio the results are shown in Table 2.
2, to the test of mythimna separata
The employing leaf of Semen Maydis is fed, title compound (I) be 500PPM with concentration.
Leaf of Semen Maydis is immersed soup, take out behind 5 seconds bracelets, dry, put 30 of 3 instar larvaes, other has clear water soaking corn leaf to do contrast, and triplicate is placed on after the processing in 25 ± 1 ° of thermostat containers, observes after 24 hours, the results are shown in Table 3.
3, to the test of carmine spider mite
Adopt immersion method, title compound (I) be 500PPM with concentration, will move 2 Kidney bean seedling true leaves that are connected into mite 50-70 head, after putting into the soup that has prepared and soaking for 5 seconds, being positioned in 20～25 ℃ of testing laboratories, is contrast with the clear water, triplicate was observed after 24 hours, the results are shown in Table 4.
4, to the test of housefly
Spray method adopts title compound (I), is 500PPM with concentration, is contrast with the clear water, each 10～20 of back 4 days female adult worm of emergence of handling, and triplicate is handled the back and is placed in 25 ± 1 ℃ the thermostat container, and " Invest, Then Investigate " the results are shown in Table 5 in 24 hours:
Subordinate list 1
Figure A9511541000162
Figure A9511541000171
Figure A9511541000181
Figure A9511541000191
Figure A9511541000201
Figure A9511541000221
Figure A9511541000241
Table 2, to black bean aphid
Compound Mortality ratio (%)
????1 ????28 ????37 ????41 ????50 ????54 ????53 ????71 ????83 More than 70～89 70～89 90 more than 90 more than 90 more than 90 more than 70～89 90 more than 90
Table 3. pair mythimna separata
Compound Mortality ratio (%)
????4 ????12 ????48 More than 90% more than 90% more than 90%
Table 4. pair carmine spider mite
Compound Mortality ratio (%)
????9 ????14 ????44 More than 90% 70～89 70～89
Table 5. pair housefly
Compound Mortality ratio (%)
????62 ????60 ????61 ????87 More than 90 70～89 70～89 70～89

Claims (4)

1, the pyrazole compound that is used for Insecticiding-miticiding, the general formula of pyrazole compound of the present invention (I) is:
In the formula:
R 1Be alkyl, haloalkyl, cycloalkyl, (replacement) phenyl, (replacement) pyridine, (replacement) pyrimidine, (replacement) naphthyl.R 2, R 3Can be identical or different, can be hydrogen, halogen, alkyl, cyano group, nitro, haloalkyl, alkoxyl group, alkylthio, (replacement) benzene (oxygen or sulphur) base, (replacement) naphthalene (oxygen or sulphur) base, (replacement) pyridine (oxygen or sulphur) base, (replacement) pyrimidine (oxygen or sulphur) base.R 4Be hydrogen, alkyl, (replacement) aminocarboxyl, carbalkoxy, alkoxyalkyl, (replacement) allyl group, (replacement) propargyl, Q is Q 1Or Q 2
Figure A9511541000022
R 5Be hydrogen, alkyl, alkoxyalkyl, alkyl-carbonyl, alkoxy carbonyl, (replacement) aminocarboxyl, (replacement) allyl group, (replacement) propargyl, (replacement) cycloalkyl, (replacement) phenyl, alkoxyl group, (replacement) phenyl, (replacement) pyridyl, (replacement) pyrimidyl.R 6Be alkyl, (replacement) cycloalkyl, (replacement) phenyl, (replacement) naphthyl, (replacement) pyridyl, (replacement) pyrimidyl, (replacement) thiazolyl, (replacement) amido and A 1～A 30Shown substituting group.
Figure A9511541000041
X is oxygen, sulphur, NNO 2, CHNO 2, CCN, NR 8
ZR 7Be SR 6Or R 9, R 9Be (replacement) pyrazoles, (replacement) imidazoles, (replacement) triazole, (replacement) pyridine amido, (replacement) pyrimidine amido, (replacement) anilino, (replacement) naphthylamine base.
R 3Be alkyl, (replacement) phenyl, (replacement) pyridyl, (replacement) pyrimidyl.
When Q is Q 1The time, R 4And R 5Can form five yuan or six-ring, R 5And R 6Also can form five yuan or six-ring, slightly as (replacement) pyrazoles, (replacement) imidazoles, (replacement) triazole, (replacement) pyridazine, (replacement) pyrrole.
R 2, R 3And In the position of pyrazoles ring, respectively can be in 3,4,5 any one position, but be preferably R 2At 3, R 3At 5, At 4.
More than said alkyl be often referred to the C of any replacement 1～6Straight or branched alkyl, substituted alkyl can be the alkyl of cyano group, nitro, halogen, alkoxyl group, carbonyl, phenyl, naphthyl substituted.Cycloalkyl refers to C 3～6Cycloalkyl, general formula (1) can be made by following method:
Method 1:
Figure A9511541000044
Method 2
Figure A9511541000051
Method 3 (is worked as R 4During=H):
Figure A9511541000052
Method 4
Figure A9511541000061
Method 5
Reaction is to carry out in inert solvent, and with triethylamine, pyridine, sodium hydroxide (potassium), anhydrous sodium carbonate (potassium), Tetrabutyl amonium bromide, triethylene diamine, 4,4-Dimethylamino pyridine, 1,8-diazacyclo, [5,4,6]-hendecene-7 is a catalyzer, temperature of reaction makes product (I) for-10 °～solvent boiling point temperature, (I) can use separately, also can be made into binary or the application of the mixed preparation more than the binary with known sterilant, miticide or sterilant, (I) shared ratio is 1%～99% in mixture.
2, according to the described pyrazole compound of claim I (I), it is characterized in that can with known sterilant, miticide, as: Chlorpyrifos 94, thiophos, Volaton, methomyl, carbofuran, Cypermethrin, the hydrogen valerate, Provado, CGA106630, RH5992, N1-25, Fipronil, triaxamate, azoles mite ester, tebufenpyrad, su8801, pyridaben, four mite piperazines, Y1-5361, szl 121 and benzoyl area kind, the pyroles insecticidal/acaricidal agent, as Ac30363, known sterilant: metaxanin, mouth is disliked acid amides, M 9834, dimethomorph, fenpiclonil, seed dressing is strong, mepanipyrim, nitrile bacterium azoles, BAS480F, BAS490F, ICIA5504, Mon24000, XRD-563, Pyrimethanil, CGA219417, ferimzone is mixed into binary or the above mixed preparation of binary.
3, mixed preparation according to claim 2 has emulsion, pulvis, wettable powder, granule, suspension concentrate.
4, title compound of the present invention (I), have desinsection, acaricidal activity, be used to prevent and treat insect and mite class on domestic animal and the plant materials, small cabbage moth, mythimna separata, Heliothis virescens, bollworm, housefly, wild cabbage root flowerfly, aphid, leafhopper, Groton bug, two-spotted spider mite, carmine spider mite are had special efficacy.
CN95115410A 1995-09-08 1995-09-08 Insecticidal acaricidal pyrazoles compounds and preparation thereof Expired - Fee Related CN1055083C (en)

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CN1321983C (en) * 2005-01-19 2007-06-20 浙江工业大学 Pyrazole-containing semicarbazide compound and its preparation method and use
US7365068B2 (en) 2004-05-18 2008-04-29 Achillion Pharmaceuticals, Inc. Substituted aryl acylthioureas and related compounds; inhibitors of viral replication
US7476686B2 (en) 2002-11-19 2009-01-13 Achillion Pharmaceuticals, Inc. Substituted aryl thioureas and related compounds; inhibitors of viral replication
US7923465B2 (en) 2005-06-02 2011-04-12 Glenmark Pharmaceuticals S.A. Cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation
AU2005326813B2 (en) * 2002-11-19 2011-08-04 Achillion Pharmaceuticals, Inc. Substituted aryl acylthioureas and related compounds; inhibitors of viral replication
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AU2005326813B2 (en) * 2002-11-19 2011-08-04 Achillion Pharmaceuticals, Inc. Substituted aryl acylthioureas and related compounds; inhibitors of viral replication
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