PYRAZOLAMIDE COMPOUND HAVING INSECTICIDAL ACTIVITY AND USE THEREOF

Abstract

The present invention discloses a pyrazolamide compound of General Formula I having an insecticidal activity and an intermediate of General Formula II used to preparing the compound of General Formula I, wherein R.sub.1 is selected from chloro or CN, R.sub.2 is selected from H, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl or C.sub.1-C.sub.5 alkoxyalkyl, R.sub.3 is selected from halo or C.sub.1-C.sub.3 haloalkyl, R.sub.4 is selected from halo, and R.sub.5 is selected from H or halo. Compared with the compounds in the prior art, the compound of General Formula I of the present invention has a higher activity at a low concentration. This reduces the amount of the compound used and the residue of the compound in farmland, and is thus environmentally friendly.

Claims

1. A pyrazolamide compound of General Formula I having an insecticidal activity: ##STR00020## wherein R.sub.1 is selected from chloro or CN; R.sub.2 is selected from H, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3 haloalkyl or C.sub.1-C.sub.5 alkoxyalkyl; R.sub.3 is selected from halo or C.sub.1-C.sub.3 haloalkyl; R.sub.4 is selected from halo; and R.sub.5 is selected from H or halo.

2. The pyrazolamide compound having an insecticidal activity according to claim 1, wherein: R.sub.1 is selected from chloro or CN; R.sub.2 is selected from H, C.sub.1-C.sub.3alkyl, CH.sub.2OCH.sub.3, CH.sub.2OCH.sub.2CH.sub.3, CH.sub.2CH.sub.2OCH.sub.3, CF.sub.3, CH.sub.2CH.sub.2F, CH.sub.2CHF.sub.2, CH.sub.2CF.sub.3, CF.sub.2CF.sub.3 or CF(CF.sub.3).sub.2; R.sub.3 is selected from chloro, bromo or trifluoromethyl; R.sub.4 is selected from chloro; and R.sub.5 is selected from H or chloro.

3. The pyrazolamide compound having an insecticidal activity according to claim 1, wherein: R.sub.1 is selected from chloro; R.sub.2 is selected from H or methyl; R.sub.3 is selected from chloro or bromo; R.sub.4 is selected from chloro; and R.sub.5 is selected from H.

4. An intermediate for preparing a pyrazolamide compound of General Formula I having an insecticidal activity according to claim 1, wherein the intermediate is represented by having a structure of General Formula II: ##STR00021## wherein R.sub.1 is selected from chloro or CN; and R.sub.2 is selected from H, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3 haloalkyl or C.sub.1-C.sub.5 alkoxyalkyl.

5. A method for preparing a compound of General Formula I according to claim 1, comprising: reacting a compound of General Formula II with a compound of General Formula III to obtain a compound of General Formula I, wherein a chemical formula of General Formula I, II, and III and the reaction scheme are shown below: ##STR00022## wherein R.sub.1 is selected from chloro or CN; R.sub.2 is selected from H, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl or C.sub.1-C.sub.5 alkoxyalkyl; R.sub.3 is selected from halo or C.sub.1-C.sub.3 haloalkyl; R.sub.4 is selected from halo; and R.sub.5 is selected from H or halo.

6. A process of preparing insecticides for controlling pests, comprising a step of using a pyrazolamide compound of General Formula I: ##STR00023## wherein R.sub.1 is selected from chloro or CN; R.sub.2 is selected from H, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3 haloalkyl or C.sub.1-C.sub.5 alkoxyalkyl; R.sub.3 is selected from halo or C.sub.1-C.sub.3 haloalkyl; R.sub.4 is selected from halo; and R.sub.5 is selected from H or halo.

7. An insecticidal composition, comprising a compound of General Formula I according to claim 1, and an agriculturally, forestrically, and hygienically acceptable carrier, wherein the content in percentage by weight of the active ingredient in the composition is 0.1-99.5%.

8. A method for controlling pests, comprising a step of applying an insecticidal composition according to claim 7 to the pests or their growth media in an effective amount of 10 g/hm.sup.2-1000 g/hm.sup.2.

9. The process of preparing insecticides for controlling pests according to claim 6, comprising a step of using the pyrazolamide compound of General Formula I, wherein, R.sub.1 is selected from chloro or CN; R.sub.2 is selected from H, C.sub.1-C.sub.3alkyl, CH.sub.2OCH.sub.3, CH.sub.2OCH.sub.2CH.sub.3, CH.sub.2CH.sub.2OCH.sub.3, CF.sub.3, CH.sub.2CH.sub.2F, CH.sub.2CHF.sub.2, CH.sub.2CF.sub.3, CF.sub.2CF.sub.3 or CF(CF.sub.3).sub.2; R.sub.3 is selected from chloro, bromo or trifluoromethyl; R.sub.4 is selected from chloro; and R.sub.5 is selected from H or chloro.

10. The process of preparing insecticides for controlling pests according to claim 6, comprising a step of using the pyrazolamide compound of General Formula I, wherein, R.sub.1 is selected from chloro; R.sub.2 is selected from H or methyl; R.sub.3 is selected from chloro or bromo; R.sub.4 is selected from chloro; and R.sub.5 is selected from H.

Description

DETAILED DESCRIPTION OF THE EMBODIMENTS

[0037] The present invention is further described in detail below with reference to specific embodiments, but the embodiments are not intended to limit the present invention.

[0038] Unless otherwise stated, the following terms used in the specification and claims have the meanings discussed below. Alkyl means a saturated aliphatic hydrocarbon group, including linear and branched forms, such as methyl, ethyl, propyl, isopropyl, and the like. Haloalkyl means a group in which an alkyl group is substituted with one or more halogen atoms, such as chloroethyl, trifluoromethyl, and the like. Alkoxyalkyl means a group with an oxygen atom attached to the end of an alkyl group, such as methoxymethyl, methoxyethyl, ethoxymethyl and the like.

Example 1

Synthesis of Compound 1.1: N-(2-N-((1-amino-2-methyl-1-acylpropan-2-yl)-formyl)-4-chloro-6-methylphenyl)-1-(3-chloropyridin-2-yl)-3-bromo-1H-pyrazol-5-carboxamide

(1) Synthesis of 2-nitro-3-methylbenzoyl chloride

[0039] ##STR00007##

[0040] 2-nitro-3-methylbenzoic acid (10.0 g, 0.055 mol), dichloroethane (200 ml), chlorosulfoxide (23.8 g, 0.2 mol), and DMF (1 drop) were sequentially added to a 250 ml single-necked flask, heated to reflux and reacted for 3 h. Then, the solvent was removed under elevated pressure to obtain a brown liquid (11.0 g, yield 100%). The product was directly used in next step without further post-treatment.

(2) Synthesis of N-(1-cyanoisopropyl)-3-methyl-2-nitrobenzamide

[0041] ##STR00008##

[0042] 2-methyl-2-(methylamino)propionitrile hydrochloride (6.0 g, 0.05 mol), tetrahydrofuran (20 ml), water (20 ml), and NaHCO.sub.3 (8.4 g, 0.1 mol) were sequentially added to a 250 ml four-necked flask. 2-nitro-3-methylbenzoyl chloride (10 g, 0.05 mol) in tetrahydrofuran (20 ml) was added dropwise at 10 C., and then continuously reacted for 2 h with stirring at 10 C. The reaction solution was added with water (50 ml), and extracted with ethyl acetate (20 ml3). The organic phases were combined, washed with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a brown solid (6.0 g, yield 48.2%).

(3) Synthesis of N-(1-cyanoisopropyl)-3-methyl-2-aminobenzamide

[0043] ##STR00009##

[0044] Water (20 ml), reduced Fe powder (2.2 g, 0.04 mol), and 30% hydrochloric acid (1 ml) were sequentially added to a 100 ml four-necked flask, slowly heated to 80 C. and stirred for 30 min at 80 C. Then, N-(1-cyanoisopropyl)-3-methyl-2-nitrobenzamide (2.5 g, 0.01 mol) was added batchwise, while the temperature was maintained at no more than 80 C. After that, the reaction was continuously stirred at 80 C., until the reaction was completed as indicated by HPLC. The reaction solution was cooled to room temperature, added with sodium hydroxide (1.6 g), and filtered with suction. The filter cake was washed with hot water, and the collected filtrate was extracted with ethyl acetate (2100 ml). The organic phase was washed with water, saturated sodium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a brown solid (1.4 g, yield 63.1%).

(4) Synthesis of N-(1-cyanoisopropyl)-2-amino-3-methyl-5-chlorobenzamide

[0045] ##STR00010##

[0046] N-(1-cyanoisopropyl)-3-methyl-2-aminobenzamide (1.5 g, 6.9 mmol), N-chlorosuccinimide (1.4 g, 10.3 mmol) and DMF (20 ml) were sequentially added to a 100 ml four-necked flask, and reacted with stirring at room temperature until the reaction was completed as indicated by HPLC. The reaction solution was poured into water (100 ml), and extracted with ethyl acetate (20 ml3). The organic phases were combined, washed sequentially with saturated aqueous sodium chloride solution and water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The resulting crude product was purified by column chromatography (petroleum ether:ethyl acetate=5:1) to obtain a white solid (1.4 g, yield 80.1%).

(5) Synthesis of N-(1-amino-2-methyl-1-acylpropan-2-yl)-2-amino-3-methyl-5-chlorobenzamide

[0047] ##STR00011##

[0048] In an ice bath, N-(1-cyanoisopropyl)-2-amino-3-methyl-5-chlorobenzamide (1 g, 4.0 mmol), tetrahydrofuran (10 ml), sodium hydroxide (0.24 g, 6.0 mmol) in water (5 ml), and 30% hydrogen peroxide solution (2 g, 18 mmol) were sequentially added to a 100 ml single-necked flask, naturally warmed to room temperature, and reacted with stirring, until the reaction was completed as indicated by HPLC. The solvent was removed from the reaction solution under reduced pressure to obtain a brownish-yellow solid. The solid was washed with tetrahydrofuran (10 ml2), and filtered. The filtrate was collected, and removed of the solvent under reduced pressure. The crude product was purified column chromatography (petroleum ether: ethyl acetate=1:1) to obtain a white solid (0.39 g, yield 40.1%).

(6) Synthesis of Compound 1.1: N-(2-N-((1-amino-2-methyl-1-acylpropan-2-yl)-formyl)-4-chloro-6-methylphenyl)-1-(3-chloropyridin-2-yl)-3-bromo-1H-pyrazol-5-carboxamide

[0049] ##STR00012##

[0050] N-(1-amino-2-methyl-1-acylpropan-2-yl)-N-methyl-2-amino-3-methyl-5-chlorobenzamide (0.27 g, 1 mmol), acetonitrile (10 ml), pyridine (0.1 g, 1 mmol), and 2-(3-chloro-pyridin-2-yl)-5-bromo-2H-pyrazol-3-carbonyl chloride (0.32 g, 1 mmol) (prepared according to a method as described in WO 02/070483) were sequentially added to a 50 ml single-necked flask, and stirred at room temperature, until the reaction was completed as indicated by HPLC. The reaction solution was poured into water (50 ml), and extracted with dichloromethane (320 ml). The organic phase was washed sequentially with saturated sodium carbonate solution, saturated aqueous sodium chloride solution and water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the resulting crude product was purified by column chromatography (eluent: ethyl acetate:petroleum ether=3:1), to obtain a white solid (0.23 g, yield 41.2%).

Example 2

Synthesis of Compound 1.3: N-methyl-N-(2-N-((1-amino-2-methyl-1-acylpropan-2-yl)-formyl)-4-chloro-6-methylphenyl)-1-(3-chloropyridin-2-yl)-3-bromo-1H-pyrazol-5-carboxamide

(1) Synthesis of 2-methyl-2-(methylamino)propionitrile

[0051] ##STR00013##

[0052] Acetone cyanohydrin (8.5 g, 0.1 mol) was added to a 50 ml four-necked flask, and then methylamine gas (3.1 g, 0.1 mol) was slowly introduced at room temperature. After that, the reaction was continuously stirred at room temperature for 5 h, and extracted with dichloromethane (10 ml3). The organic phase were combined and dried over anhydrous sodium sulfate. Then, the solvent was removed under reduced pressure to obtain a colorless transparent liquid (6.18 g, yield 63.0%).

(2) Synthesis of 2-nitro-3-methylbenzoyl chloride

[0053] ##STR00014##

[0054] 2-nitro-3-methylbenzoic acid (5.4 g, 0.03 mol), dichloroethane (100 ml), chlorosulfoxide (23.8 g, 0.2 mol), and DMF (1 drop) were sequentially added to a 250 ml single-necked flask, heated to reflux and reacted for 3 h. Then, the solvent was removed under elevated pressure to obtain a brown liquid (5.7 g, yield 95.2%). The product was directly used in next step without further post-treatment.

(3) Synthesis of N-(1-cyanoisopropyl)-N-methyl-3-methyl-2-nitrobenzamide

[0055] ##STR00015##

[0056] 2-methyl-2-(methylamino)propionitrile hydrochloride (4.0 g, 0.03 mol), tetrahydrofuran (10 ml), water (10 ml), and NaHCO.sub.3 (5.1 g, 0.06 mol) were sequentially added to a 250 ml four-necked flask. 2-nitro-3-methylbenzoyl chloride (5.7 g) in tetrahydrofuran (20 ml) was added dropwise at 10 C., and then continuously reacted for 2 h with stirring at 10 C. The reaction solution was added with water (50 ml), and extracted with ethyl acetate (20 ml3). The organic phases were combined, washed with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a brown solid (4.4 g, yield 56.5%).

(4) Synthesis of N-(1-cyanoisopropyl)-N-methyl-3-methyl-2-aminobenzamide

[0057] ##STR00016##

[0058] Water (20 ml), reduced Fe powder (2.2 g, 0.04 mol), and 30% hydrochloric acid (1 ml) were sequentially added to a 100 ml four-necked flask, slowly heated to 80 C. and stirred for 30 min at 80 C. Then, N-(1-cyanoisopropyl)-N-methyl-3-methyl-2-nitrobenzamide (2.6 g, 0.01 mol) was added batchwise, while the temperature was maintained at no more than 80 C. After that, the reaction was continuously stirred at 80 C., until the reaction was completed as indicated by HPLC. The reaction solution was cooled to room temperature, added with sodium hydroxide (1.6 g), and filtered with suction. The filter cake was washed with hot water, and the collected filtrate was extracted with ethyl acetate (2100 ml). The organic phase was washed with water, saturated sodium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a brown solid (1.68 g, yield 71.3%).

(5) Synthesis of N-(1-cyanoisopropyl)-N-methyl-2-amino-3-methyl-5-chlorobenzamide

[0059] ##STR00017##

[0060] N-(1-cyanoisopropyl)-N-methyl-3-methyl-2-aminobenzamide (1.6 g, 6.9 mmol), N-chlorosuccinimide (1.4 g, 10.3 mmol) and DMF (20 ml) were sequentially added to a 100 ml four-necked flask, and reacted with stirring at room temperature until the reaction was completed as indicated by HPLC. The reaction solution was poured into water (100 ml), and extracted with ethyl acetate (20 ml3). The organic phases were combined, washed sequentially with saturated aqueous sodium chloride solution and water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a light yellow solid (1.52 g, yield 83.1%).

(6) Synthesis of N-(1-amino-2-methyl-1-acylpropan-2-yl)-N-methyl-2-amino-3-methyl-5-chlorobenzamide

[0061] ##STR00018##

[0062] In an ice bath, N-(1-cyanoisopropyl)-N-methyl-2-amino-3-methyl-5-chlorobenzamide (0.80 g, 3.0 mmol), tetrahydrofuran (10 ml), potassium hydroxide (0.35 g, 6.0 mmol) in water (5 ml), and 30% hydrogen peroxide solution (2 g, 18 mmol) were sequentially added to a 100 ml single-necked flask, naturally warmed to room temperature, and reacted with stirring, until the reaction was completed as indicated by HPLC. The solvent was removed from the reaction solution under reduced pressure to obtain a brownish-yellow solid. The solid was washed with tetrahydrofuran (10 ml2), and filtered. The filtrate was collected, and removed of the solvent under reduced pressure. The crude product was purified column chromatography (petroleum ether: ethyl acetate=1:1) to obtain a white solid (0.31 g, yield 36.7%).

(7) Synthesis of N-methyl-N-(2-N-((1-amino-2-methyl-1-acylpropan-2-yl)-formyl)-4-chloro-6-methylphenyl)-1-(3-chloropyridin-2-yl)-3-bromo-1H-pyrazol-5-carboxamide

[0063] ##STR00019##

[0064] N-(1-amino-2-methyl-1-acylpropan-2-yl)-N-methyl-2-amino-3-methyl-5-chlorobenzamide (0.30 g, 1 mmol), acetonitrile (10 ml), pyridine (0.079 g, 1 mmol), and 2-(3-chloro-pyridin-2-yl)-5-bromo-2H-pyrazol-3-carbonyl chloride (0.32 g, 1 mmol) (prepared according to a method as described in WO 02/070483) were sequentially added to a 50 ml single-necked flask, and stirred at room temperature until the reaction was completed as indicated by HPLC. The reaction solution was poured into water (50 ml), and extracted with dichloromethane (320 ml). The organic phase was washed sequentially with saturated sodium carbonate solution, saturated aqueous sodium chloride solution and water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the resulting crude product was purified by column chromatography (eluent: ethyl acetate:petroleum ether=3:1), to obtain a white solid (0.24 g, yield 42.8%).

[0065] The other compounds could be synthesized by the above method.

[0066] Biological Activity Test

[0067] The test reagents were all individually dissolved in a mixed solvent of acetone:NN-dimethylcarboxamide (1:1) to give a 1000 mg/L solution. 1% Tween-80 was added as an emulsifier to each solution. These solutions were then diluted with 1% Tween-20 solution in water to give desired concentrations of test solutions. An aqueous solution containing 1% Tween-20 was used as a control.

Example 3: Insecticidal Effect on Spodoptera litura

[0068] Third instar larvae of Spodoptera litura were used, and the insecticidal effect test was carried out by feeding with leaves immersed with various compounds. The cabbage leaves that had not been exposed to insecticides were cut into leaf discs of about 40 square-mm with scissors. The leaf discs were immersed in each compound solution for 30 s. Then the leaf discs were placed on absorbent paper and air-dried until there were no obvious water stains on the leaf discs. The leaf discs soaked with the reagents were placed in a petri dish (7 cm), each petri dish having 3 leaf discs. The 3rd instar larvae of Spodoptera litura raised on the indoor cabbage plants were gently picked up with a pen brush and placed on the leaf discs in the petri dish, each petri dish having 10-15 insects. After the insects were inoculated, the petri dish was covered, and placed in an insect-cultivating chamber at 25 C. with a 16-h-light/8-h-dark photoperiod. The number of deaths in 5 days was investigated, and the mortality was calculated.

[0069] When the concentration of the reagent solution is 40 ppm, some compounds such as 1.1 have a better control effect on Spodoptera litura, reaching more than 80%.

Example 4: Insecticidal Effect on Jacobiasca formosana

[0070] The leaves (with petioles) on peach tree were cut, and more than 10 2nd-to-4th-instar nymphs (old nymphs were removed with sharp needles) of Jacobiasca formosana were present on the leaves. The leaves with the nymphs were immersed in the test solutions of each reagent for 20 s, and then taken out. The petiole was wrapped with absorbent cotton. The leaves were laterally placed in a Petri dish with filter paper, and the water on the surface of the leaves was absorbed by the filter paper. Then the Petri dish was covered. 3 replicates were set for each treatment. After the treatment, the petri dish was placed in an insect cultivating incubator at 25 C. light with a 16-h-light/8-h-dark photoperiod. 72 hrs after the insects were inoculated, the deaths of Jacobiasca formosana were investigated to calculate the mortality.

[0071] When the concentration of the reagent solution is 40 ppm, some compounds such as 1.1 and 1.3 have a better control effect on Jacobiasca formosana, reaching more than 80%.

Example 5: Insecticidal Effect on Frankliniella intonsa

[0072] On the bottom of a glass petri dish with a diameter of 6 cm, a piece of filter paper with the same diameter was laid. 1 mL of the reagent solution was drawn by a pipette and uniformly dripped on the filter paper. After the acetone was volatilized, Nymphs of Frankliniella intonsa were transferred from Bombax ceiba with a brush pen to the filter paper in the petri dish. After 0.5-1 h when the insect body was fully covered with the reagent, 3 cm-long petals of Bombax ceiba were placed and the Petri dish were covered. 3 replicates were set for each treatment. After the insects were inoculated, the petri dish was placed in an insect-cultivating chamber at 25 C. with a 16-h-light/8-h-dark photoperiod. 72 hrs after the insects were inoculated, the deaths of Frankliniella intonsa were investigated to calculate the mortality.

[0073] When the concentration of the reagent solution is 60 ppm, some compounds such as 1.1 have a better control effect on Frankliniella intonsa, reaching more than 80%.

Example 6: Insecticidal Effect on Nilaparvata lugens

[0074] Soil was washed off from the root of 60-day-old seedlings and the leaves were cut off. After air drying, the remaining portion was immersed for 30 s in the test solution of each reagent, then taken out, placed on absorbent paper and air-dried. The root crown was wrapped with absorbent cotton, and the root was immersed in clear water through the bottle cap. The above-ground portion was housed in a plastic insect cultivating bottle (with 32 cm square holes on both sides and sealed with a fine mesh); and placed in a plastic cup. 3 replicates were set for each treatment. 3rd to 4th instar nymphs of Nilaparvata lugens raised on indoor rice seedlings were gently picked up with a brush pen and placed on seedlings in plastic cups, and 10 insects per cup were inoculated. After the insects were inoculated, the plastic cup was placed in an insect-cultivating chamber at 25 C. with a 16-h-light/8-h-dark photoperiod. 120 hrs after the insects were inoculated, the deaths of Nilaparvata lugens were investigated to calculate the mortality.

[0075] When the concentration of the reagent solution is 40 ppm, some compounds such as 1.1 and 1.2 have a better control effect on Nilaparvata lugens, reaching more than 80%.

Example 7: Insecticidal Effect on Helicoverpa armigera

[0076] Third instar larvae of Helicoverpa armigera were used, and the insecticidal effect test was carried out by feeding with leaves immersed with various compounds. The cabbage leaves that had not been exposed to insecticides were punched into leaf discs having a diameter of 1.5 mm. The leaf discs were immersed in each compound solution for 30 s. Then the leaf discs were placed on absorbent paper and air-dried until there were no obvious water stains on the leaf discs. A washed 24-well plate was prepared, and about 1 ml of water agar medium was fed to each well. After solidification, the treated leaf discs were placed on the medium in the 24-well plate, and then 1 3rd-instar larva of Helicoverpa armigera was inoculated into each well. The 24-well plate was covered after inoculation, placed in an insect cultivating chamber at 25 C. with a 16-h-light/8-h-dark photoperiod. The number of deaths in 3 days was investigated, and the mortality was calculated.

[0077] Some test results are as follows:

[0078] When the concentration of the reagent solution is 40 ppm, the mortality of 3rd instar larvae of Helicoverpa armigera caused by some compounds such as 1.1, 1.2, and 1.3 is 80% or higher.

[0079] According to the above method, Comparative Compounds KCl (Compound 1.3 in CN 104447688) and KC2 (Compound 1.4 in CN 104447688) in the prior art which are closest in structure to the compound of the present invention were tested for the insecticidal activity on Helicoverpa armigera. The experimental results are shown in Table 4 below.

TABLE-US-00004 TABLE 4 Parallel comparison of the insecticidal activity of Compounds 1.1 and 1.2 of the present invention with known Compound KC1 and KC2 on Helicoverpa armigera (mortality %) Concentration (ppm) 15 5 Compound Insecticidal activity (%) 1.1 87.5 75.0 1.2 90.0 75.9 KC1 46.7 10.0 KC2 37.5 16.7

[0080] It can be seen from the above table that when used in the killing of Helicoverpa armigera, compared with Compound KCl and Compound KC2 disclosed in the prior art, the killing rate of the compound of the present invention for Helicoverpa armigera can still reach 70% at a concentration of less than 20 ppm, even at a concentration of 5 ppm. Therefore, compared with Compound KCl and KC2 in the prior art, the activity of the compound of the present invention is much higher.