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Preparation of N-phenyl-5-substituted aminopyrazole compounds and application thereof

A technology of aminopyrazoles and compounds, applied in applications, animal repellents, plant growth regulators, etc., can solve the problems of application restrictions in pest control, high toxicity of aquatic organisms, etc.

Active Publication Date: 2013-05-15
HUNAN HAILI HIGH TECH IND GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Fipranil not only has a good control effect on lepidopteran pests such as diamondback moth and Spodoptera litura, and homopteran pests such as aphids, but also has high sensitivity to coleopteran insects, especially coleopteran flea beetles. Coleopteran insects, especially Coleopteran flea beetle pest control agents, have played an important role in the process of realizing efficient agriculture, but because fipronil is highly toxic to aquatic organisms such as bees, silkworms, shrimps, and crabs, it has caused it to become a pest in paddy fields. The application of control is greatly limited, and it has been restricted and banned in many countries. my country has banned it on July 1, 2009. At present, there is an urgent need for agents that can replace fipronil to effectively control flea beetle pests.

Method used

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  • Preparation of N-phenyl-5-substituted aminopyrazole compounds and application thereof
  • Preparation of N-phenyl-5-substituted aminopyrazole compounds and application thereof
  • Preparation of N-phenyl-5-substituted aminopyrazole compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] (E)-5-(3-chloroallyl)amino 1-(2,6-dichloro-4-trifluoromethyl)phenyl-4-trifluoromethylsulfinylpyrazole-3-carbonitrile (I-01) 5% wettable powder (weight):

[0068] Component Weight percentage (%)

[0069] (E)-5-(3-chloroallyl)amino 1-(2,-dichloro-4-trifluoromethyl)phenyl-4-trifluoromethyl

[0070] 5

[0071] Sulfinylpyrazole-3-carbonitrile (I-01)

[0072] Wetting agent (lignosulfonate) 10

[0073] Dispersant (alkyl sulfonate) 3

[0074] Spreading agent (potassium cocoate) 3

[0075] Stabilizer (magnesium aluminum silicate) 1

[0076] Synergist (naphthyl propargyl ether) 3.7

[0077] Penetrant (Laurocaprazine) 5

[0078] PH value regulator (sodium hydroxide and citric acid) 0.3

[0079] Filler (kaolin) 69

[0080] The sum of each component is 100%

[0081] Weigh 95% of the compound of formula (I) according to the above ratio: (E)-5-(3-chloroallyl)amino-1-(2,6-dichloro-4-trifluoromethyl)phenyl- 4-trif...

Embodiment 2

[0083] (E)-5-(3-chloroallyl)amino 1-(2,6-dichloro-4-trifluoromethyl)phenyl-4-trifluoromethylsulfinylpyrazole-3-carbonitrile (I-01) 10% emulsifiable concentrate (weight):

[0084] Component Weight percentage (%)

[0085] (E)-5-(3-chloroallyl)amino 1-(2,6-dichloro-4-trifluoromethyl)phenyl-4-trifluoro

[0086] 10

[0087] Methylsulfinylpyrazole-3-carbonitrile (I-01)

[0088] Emulsifier (alkylphenol polyoxyethylene ether) 10

[0089] Cosolvent (ethyl acetate) 3

[0090] Stabilizer (epoxidized linseed oil) 3

[0091] Synergist (naphthyl propargyl ether) 2

[0092] Organic solvent (ethanol) 69

[0093] Penetrant (sodium di-sec-octyl maleate sulfonate) 2

[0094] Defoamer (S-29) 0.5

[0095] PH value regulator (acetic acid) 0.5

[0096] The sum of each component is 100%

[0097] Weigh 95% of the compound of formula (I) according to the above ratio: (E)-5-(3-chloroallyl)amino-1-(2,6-dichloro-4-trifluoromethyl)phenyl...

Embodiment 3

[0099] (E)-5-(3-chloroallyl)amino 1-(2,6-dichloro-4-trifluoromethyl)phenyl-4-trifluoromethylsulfinylpyrazole-3-carbonitrile (I-01) 10% suspending agent (weight):

[0100] Component Weight percentage (%)

[0101] (E)-5-(3-chloroallyl)amino 1-(2,6-dichloro-4-trifluoromethyl)phenyl-4-trifluoromethyl

[0102] 10

[0103] Sulfinylpyrazole-3-carbonitrile (I-01)

[0104] Wetting agent (lignosulfonate) 5

[0105] Dispersant (naphthalene sulfonate) 5

[0106] Spreading agent (polyvinyl alcohol) 6

[0107] Stabilizer (magnesium aluminum silicate) 1

[0108] Synergist (synergist amine) 2

[0109] Penetrant (JFC series) 2

[0110] Thickener (alkanolamide) 3

[0111] Antifreeze (glycerol) 0.5

[0112] Defoamer (SAF) 0.5

[0113] water 66.5

[0114] The sum of each component is 100%

[0115] Weigh 95% of the compound of formula (I) according to the above ratio: (E)-5-(3-chloroallyl)amino-1-(2,6-dichloro-4-trifluoromethy...

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Abstract

N-phenyl-5-substituted aminopyrazole preparations and application thereof for controlling coleoptera pests. The title compound is as shown by formula (I), wherein X represents SO or S; R represents C1-C4 alkyl or C1-C4 halogenated alkyl; R1 and R2 are the same or different, and represent H, C3-C6 halogenated alkenyl, C3-C6 alkynyl, C3-C6 halogenated alkynyl, cyclopropylmethyl; with the proviso that R1 and R2 do not represent H at the same time, and when X is S and R is CF3, R1 and R2 do not represent propargyl at the same time. The insecticidal compounds have insecticidal rate of 65-100% on flea beetle at the concentration of 10-1,000 ppm. The insecticidal compounds can be prepared into wettable powder, emulsifiable concentrate, suspension, microemulsion, water emulsion and water-dispersible granule in the presence of corresponding adjuvants.

Description

technical field [0001] The present invention relates to the preparation of N-phenyl-5-substituted aminopyrazole compound and its application in controlling Coleoptera insects. Background technique [0002] Coleoptera (Coleoptera) is the largest order in the insect class, including various beetles, belonging to the winged subclass and the holometabolism class. At present, there are about 182 families and 350,000 species of beetles in the world, and there are about 7,000 species in China. More than the sum of all other purposes in the animal kingdom. Beetles can be found in any environment except in the oceans and polar regions. Most species belong to the worldwide distribution, such as carapace, leaf beetle, scarab and some species of weevil family; a few species are mainly distributed in tropical areas, and species in temperate areas are gradually decreasing, such as tiger beetle, chitin beetle, longhorn beetle and beetle. Some species of stag beetles; the distribution of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A01N47/02A01N43/56A01P7/04A01N25/14A01N25/04
CPCA01N43/56A01N47/02
Inventor 柳爱平聂思桥裴晖王晓光黄明智刘兴平余淑英刘卫东欧晓明成四喜
Owner HUNAN HAILI HIGH TECH IND GRP