CN-122010767-A - Haloalkyl bisamide compound and application thereof

Abstract

The invention relates to the technical field of pesticide chemicals, in particular to a halogenated alkyl bisamide compound and application thereof. The structural formula of the synthesized halogenated alkyl bisamide compound is shown as follows. According to the invention, the m-diamide structure is taken as a parent body, and the trifluoroethyl is introduced on the amide group to increase the fat solubility of the diamide compound, so that the diamide compound can enter the insect body more easily through a biomembrane, and the trifluoroethyl enhances the binding force of the diamide molecule and target protein, so that better insecticidal activity is shown.

Inventors

• JIAO PEIFU
• CHEN JIAHUI
• TANG YUANKUN
• LIU YUNTING
• LIU JIANXIN
• XU LIN

Assignees

• 山东熙霖生物科技有限公司

Dates

Publication Date

20260512

Application Date

20260203

Claims (8)

1. 1. A haloalkyl bisamide compound is characterized in that, the chemical structural formula of the halogenated alkyl bisamide compound is as follows: ; wherein X is selected from the group consisting of a ketone group or a sulfonyl group; R 1 is selected from substituted phenyl, substituted pyridinyl or substituted C 5 heteroaryl; R 2 is selected from trifluoromethyl, difluoromethyl or monofluoromethyl; R 3 is selected from halogen or methyl.
2. 2. The haloalkylbisamide compound according to claim 1, wherein the substituent in R 1 is at least one selected from halogen, nitro, cyano, methylsulfonyl, methoxy, C 1 ～C 4 alkyl and C 1 ～C 4 haloalkyl.
3. 3. The haloalkylbisamide compound according to claim 1, wherein the heteroatom of the C 5 heteroaryl is selected from at least one of N, O and S.
4. 4. The haloalkylbisamide compound according to claim 1, wherein the haloalkylbisamide compound is selected from one of the following compounds: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 。
5. 5. an application of a haloalkyl bisamide compound in preparing pesticides for controlling pests, wherein the haloalkyl bisamide compound is the haloalkyl bisamide compound according to any one of claims 1 to 4.
6. 6. The application of the haloalkyl bisamide compound in preparing pesticides for controlling pests according to claim 5, wherein the concentration of the haloalkyl bisamide compound in the pesticides for controlling pests is 10 ppm-100 ppm when the haloalkyl bisamide compound is used.
7. 7. The use of a haloalkylbisamide compound according to claim 5, wherein the pest is an insect containing a gamma-aminobutyric acid receptor.
8. 8. The use of a haloalkylbisamide compound according to claim 7, wherein the insect containing gamma-aminobutyric acid receptor is spodoptera exigua or chilo suppressalis.

Description

Haloalkyl bisamide compound and application thereof Technical Field The invention relates to the technical field of pesticide chemicals, in particular to a halogenated alkyl bisamide compound and application thereof. Background The English of the gamma-aminobutyric acid is called gamma-aminobutyric acid, which is called GABA for short. In normal physiological processes, GABA is released from synaptic cells and then binds to the GABA receptor of the insect, activating chloride channels, allowing chloride to flow in, thus inhibiting neural activity of the insect. The metadiamide pesticide is used as an allosteric inhibitor of a GABA-gated chloride ion channel, can be combined with an allosteric site of the channel, so that the channel conformation is changed and cannot be normally opened, and the inflow of chloride ions is blocked. Disruption of this inhibition will result in sustained hyperexcitation of the pest nervous system, ultimately leading to spasticity and death. Bromofluorobenzene bisamide is a representative commercial product in this mechanism of action, which was co-developed by Mitsui chemistry and Basoff and categorized in 2017 by the International Commission on pesticide resistance action as a completely new class, group 30. The product has good control effect on lepidoptera pests (such as asparagus caterpillar and plutella xylostella), coleopteran pests (such as flea beetle) and the like. Wherein, the structural formula of the bromofluorobenzene bisamide is as follows: 。 However, in actual use, the existing m-diamide compound generally needs to increase the dosage of the medicament to achieve enough field prevention effect, so that the medicament cost is increased, and the phytotoxicity and resistance of the plant are easily induced. Disclosure of Invention Aiming at the technical problems that the prior m-diamide compound needs to increase the dosage of the medicament to achieve enough field prevention effect, the medicament cost is increased, and the phytotoxicity and resistance are easy to induce, the invention provides a halogenated alkyl diamide compound and application thereof. According to the invention, the fluorine-containing ethyl is introduced into the amide group to increase the fat solubility of the bisamide compound, so that the bisamide compound can enter the insect body through a biological membrane more easily, the fluorine-containing ethyl enhances the binding force of bisamide molecules and target proteins, and the fluorine-containing ethyl is used as an allosteric inhibitor of GABA gate chloride ion channels to trigger death of pests, so that better insecticidal activity is shown. At equal or lower applied doses, better insecticidal rates can be achieved. The first object of the present invention is to provide a haloalkyl bisamide compound, wherein the chemical structural formula of the haloalkyl bisamide compound is as follows: ; wherein X is selected from a ketone group or a sulfonyl group, R 1 is selected from a substituted phenyl group, a substituted pyridine ring or a substituted C 5 heteroaryl group, R 2 is selected from a trifluoromethyl group, a difluoromethyl group or a monofluoromethyl group, and R 3 is selected from a halogen or a methyl group. Preferably, the substituents in R 1 are selected from at least one of halogen, nitro, cyano, methylsulfonyl, methoxy and C 1～C4 alkyl and C 1～C4 haloalkyl. Preferably, the heteroatom of the C 5 heteroaryl is selected from at least one of N, O and S. Preferably, the haloalkyl bisamide compound is selected from one of the following compounds: 、、、、、、、、、、、、、、、、、、 、、。 Preferably, the haloalkyl bisamide compound is selected from one of the following compounds: 、、、、、、、、、、、、。 The second object of the invention is to provide an application of the halogenated alkyl bisamide compound in preparing pesticides for preventing and controlling pests. Preferably, the haloalkyl bisamide compound is applied to preparing pesticides for controlling pests, and other combined small-molecule pesticides or biopesticides are used before, after or simultaneously with the haloalkyl bisamide compound. Preferably, when the compound is used, the concentration of the halogenated alkyl bisamide compound in the pesticide for preventing and controlling pests is 10 ppm-100 ppm. Preferably, the pest is an insect containing gamma-aminobutyric acid receptors. Preferably, the insects containing the gamma-aminobutyric acid receptor include at least one of plutella xylostella, spodoptera exigua, spodoptera frugiperda, cabbage looper, kapok, cutworm, spodoptera litura, spodoptera exigua, cabbage looper, peach leaf roller, beet armyworm, schwann, coffee looper, tomato moth, apple looper, peach leaf roller, wax moth, plum diamond back moth, pear looper, corn borer, tobacco leaf roller, corn earworm, apple leaf roller, fall webworm, citrus looper, potato moth, soybean looper, plutella xylostella, wheat moth, grape leaf roller, jasmine flower bud roller, sea ash, flour