ISOXAZOLINE COMPOUNDS AND USE THEREOF

Abstract

Disclosed are an isoxazoline compound and an application thereof. The structure of the compound is as shown in general formula (I). The definitions of substituents in the formula are described in the description. The description also discloses use of the compound of general formula (I) as an insecticide, acaricide and animal parasite control agent.

##STR00001##

Claims

1. An isoxazoline compound as shown in Formula I: ##STR00025## In Formula I: R.sub.1 is selected from hydrogen, chlorine, or fluorine; R.sub.2 is selected from C.sub.1-C.sub.6 alkoxy C.sub.1-C.sub.6 alkyl, substituted or unsubstituted C.sub.3-C.sub.8 cycloalkyl; or a stereoisomer of the compound of Formula I; or a salt of the compound of Formula I.

2. The isoxazoline compound according to claim 1, wherein in Formula I: R.sub.1 is selected from hydrogen, chlorine, or fluorine; R.sub.2 is selected from C.sub.1-C.sub.4 alkoxy C.sub.1-C.sub.3 alkyl, substituted or unsubstituted C.sub.3-C.sub.6 cycloalkyl.

3. The isoxazoline compound according to claim 2, wherein in Formula I: R.sub.1 is selected from hydrogen or fluorine; R.sub.2 is selected from C.sub.1-C.sub.4 alkoxy C.sub.1-C.sub.2 alkyl, substituted or unsubstituted C.sub.3-C.sub.4cycloalkyl.

4. The isoxazoline compound according to claim 1, wherein when the cycloalkyl group is substituted, it is monosubstituted or polysubstituted, and the substituent(s) may be one or more selected from the group consisting of methyl, halogen, and cyano.

5. The isoxazoline compound according to claim 1, wherein the salt of the compound of Formula I includes a salt formed by the reaction of the compound of Formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid.

6. The isoxazoline compound according to claim 1, wherein the isoxazoline compound is selected from: the compounds in Table 1, which have the structure of Formula I with R.sub.1 and R.sub.2 being those listed in Table 1; TABLE-US-00006 TABLE 1 No. R.sub.1 R.sub.2 No. R.sub.1 R.sub.2 1 H cyclopropyl 2 F cyclopropyl 3 H 1-methylcyclopropyl 4 F 1-methylcyclopropyl 5 H 2,2-dimethylcyclopropyl 6 F 2,2-dimethylcyclopropyl 7 H 2,2,3,3- 8 F 2,2,3,3-tetramethylcyclopropyl tetramethylcyclopropyl 9 H 1-cyanocyclopropyl 10 F 1-cyanocyclopropyl 11 H cyclobutyl 12 F cyclobutyl 13 H 1-methylcyclobutyl 14 F 1-methylcyclobutyl 15 H cyclopentyl 16 F cyclopentyl 17 H cyclohexyl 18 F cyclohexyl 19 H CH.sub.3OCH.sub.2— 20 F CH.sub.3OCH.sub.2— 21 H CH.sub.3CH.sub.2OCH.sub.2— 22 F CH.sub.3CH.sub.2OCH.sub.2— 23 H CH.sub.3CH.sub.2CH.sub.2OCH.sub.2— 24 F CH.sub.3CH.sub.2CH.sub.2OCH.sub.2— 25 H (CH.sub.3).sub.2CHOCH.sub.2— 26 F (CH.sub.3).sub.2CHOCH.sub.2— 27 H CH.sub.3CH.sub.2CH.sub.2CH.sub.2OCH.sub.2— 28 F CH.sub.3CH.sub.2CH.sub.2CH.sub.2OCH.sub.2— 29 H (CH.sub.3).sub.3COCH.sub.2— 30 F (CH.sub.3).sub.3COCH.sub.2— 31 H CH.sub.3OCH.sub.2CH.sub.2— 32 F CH.sub.3OCH.sub.2CH.sub.2— 33 H CH.sub.3CH.sub.2OCH.sub.2CH.sub.2— 34 F CH.sub.3CH.sub.2OCH.sub.2CH.sub.2— 35 H CH.sub.3CH.sub.2CH.sub.2OCH.sub.2CH.sub.2— 36 F CH.sub.3CH.sub.2CH.sub.2OCH.sub.2CH.sub.2— 37 H CH.sub.3CH.sub.2CH.sub.2CH.sub.2OCH.sub.2CH.sub.2— 38 F CH.sub.3CH.sub.2CH.sub.2CH.sub.2OCH.sub.2CH.sub.2— or a stereoisomer of any one of the compounds from Table 1; or a salt formed by the reaction of any one of the compounds from Table 1 with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid.

7. The isoxazoline compound according to claim 6, wherein the isoxazoline compound is selected from: the compounds in Table 2, which have the structure of Formula I with R.sub.1 and R.sub.2 being those listed in Table 2; TABLE-US-00007 TABLE 2 No. R.sub.1 R.sub.2 No. R.sub.1 R.sub.2 1 H cyclopropyl 2 F cyclopropyl 19 H CH.sub.3OCH.sub.2— 20 F CH.sub.3OCH.sub.2— 21 H CH.sub.3CH.sub.2OCH.sub.2— 22 F CH.sub.3CH.sub.2OCH.sub.2— 23 H CH.sub.3CH.sub.2CH.sub.2OCH.sub.2— 24 F CH.sub.3CH.sub.2CH.sub.2OCH.sub.2— 27 H CH.sub.3CH.sub.2CH.sub.2CH.sub.2OCH.sub.2— 28 F CH.sub.3CH.sub.2CH.sub.2CH.sub.2OCH.sub.2— 31 H CH.sub.3OCH.sub.2CH.sub.2— 32 F CH.sub.3OCH.sub.2CH.sub.2— 33 H CH.sub.3CH.sub.2OCH.sub.2CH.sub.2— 34 F CH.sub.3CH.sub.2OCH.sub.2CH.sub.2— 35 H CH.sub.3CH.sub.2CH.sub.2OCH.sub.2CH.sub.2— 36 F CH.sub.3CH.sub.2CH.sub.2OCH.sub.2CH.sub.2— 37 H CH.sub.3CH.sub.2CH.sub.2CH.sub.2OCH.sub.2CH.sub.2— 38 F CH.sub.3CH.sub.2CH.sub.2CH.sub.2OCH.sub.2CH.sub.2— or a stereoisomer of any one of the compounds from Table 2; or a salt formed by the reaction of any one of the compounds from Table 2 with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid.

8. The isoxazoline compound according to claim 7, wherein the isoxazoline compound is selected from: the compounds in Table 3, which have the structure of Formula I with R.sub.1 and R.sub.2 being those listed in Table 3; TABLE-US-00008 TABLE 3 No. R.sub.1 R.sub.2 No. R.sub.1 R.sub.2 1 H cyclopropyl 2 F cyclopropyl 19 H CH.sub.3OCH.sub.2— 20 F CH.sub.3OCH.sub.2— 21 H CH.sub.3CH.sub.2OCH.sub.2— 22 F CH.sub.3CH.sub.2OCH.sub.2— 23 H CH.sub.3CH.sub.2CH.sub.2OCH.sub.2— 24 F CH.sub.3CH.sub.2CH.sub.2OCH.sub.2— or a stereoisomer of any one of the compounds in Table 3; or a salt formed by the reaction of any one of the compounds in Table 3 with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid.

9. A method for preparing the isoxazoline compound according to claim 1, wherein when the isoxazoline compound is the compound of Formula I, the method comprises the following steps: ##STR00026## the compound of Formula II and the compound of Formula III are allowed to react in a solvent at a temperature from −10° C. to the boiling point of the solvent for 0.5-48 hours.

10. Use of the isoxazoline compound according to claim 1, in the preparation of insecticides and/or acaricides.

11. The use according to claim 10, wherein the insecticide and/or acaricide is used to control one or more of Leucania separata, Plutella xylostella, Chilo suppres salis, and Tetranychus cinnabarinus.

12. An insecticide formulation or acaricide formulation, wherein the insecticide formulation or acaricide formulation contains the isoxazoline compound according to claim 1 as an active ingredient, and also contains one or more adjuvants; optionally, the amount of the isoxazoline compound in the insecticide formulation or acaricide formulation is 0.1 to 99% by weight, and further optionally 0.5 to 90% by weight.

13. An insecticide composition or acaricide composition, comprising a mixture of the isoxazoline compound according to claim 1 and an additional active compound, in which the additional active compound is one or more of an insecticide, a poison bait, a disinfectant, an acaricide, a nematicide, a fungicide, a growth regulator, and an herbicide.

14. A method for controlling agricultural or forestry pests and/or mites, comprising applying an effective dose of material to the pests and/or mites to be controlled, or to their growth media, in which the material is one or more selected from the group consisting of: the isoxazoline compound according to claim 1; the insecticide formulation or acaricide formulation; the insecticide composition or acaricide composition.

15. Use of the isoxazoline compound according to claim 1 in the preparation of an animal parasite control agent.

16. The use according to claim 15, wherein the animal parasite control agent is used for controlling one or more of cat fleas and American dog ticks.

17. An animal parasite control agent, comprising the isoxazoline compound according to claim 1 as an active component, and one or more adjuvants; optionally, the amount of the isoxazoline compound in the animal parasite control agent is 1 to 80 wt %.

18. An animal parasite control composition, comprising a mixture of the isoxazoline compound according to claim 1 and an additional animal parasite control active compound, wherein the additional animal parasite control active compound is one or more of acaricides, insecticides, parasiticides, and antiplasmodium agents.

19. A method for controlling animal parasites, comprising the following steps: applying an effective dose of material to the animal parasites to be controlled, or to their growth media, wherein the material is one or more selected from the group consisting of: the isoxazoline compound according to claim 1; the animal parasite control agent; the animal parasite control composition.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0079] In order to make the purpose, technical solutions and advantages of the embodiments of the invention clearer, the technical solutions in the embodiments of the invention will be described clearly and completely, obviously, the described embodiments are some of the embodiments of the present invention, but not all of them. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative work are within the scope of the present invention.

[0080] In addition, in order to better explain the present invention, a lot of specific details are given in the following embodiments. It will be understood by those skilled in the art that the present invention may be practiced without certain specific details. In some embodiments, materials, elements, methods, means, etc., well known to those skilled in the art, are not described in detail so as to highlight the spirit of the present invention.

[0081] Throughout the specification and claims, the term “comprising” or variations thereof, such as “including” or “containing” and the like, will be understood to include the stated components and not to exclude other elements or other components, unless expressly indicated otherwise.

[0082] Unless otherwise indicated, all raw materials used are commercially available.

[0083] In the present invention, the terms used have the following meanings:

[0084] Cycloalkyl: substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopentyl, or cyclohexyl; and the substituent can be, for example, methyl, halogen, cyano, etc.

[0085] Alkoxy alkyl: alkyl-O-alkyl-, for example, CH.sub.3OCH.sub.2—, CH.sub.3CH.sub.2OCH.sub.2—, CH.sub.3CH.sub.2CH.sub.2OCH.sub.2—, (CH.sub.3).sub.2CHOCH.sub.2—, CH.sub.3CH.sub.2CH.sub.2CH.sub.2OCH.sub.2—, (CH.sub.3).sub.3COCH.sub.2—, CH.sub.3OCH.sub.2CH.sub.2—, CH.sub.3CH.sub.2OCH.sub.2CH.sub.2—, CH.sub.3CH.sub.2CH.sub.2OCH.sub.2CH.sub.2—, or CH.sub.3CH.sub.2CH.sub.2CH.sub.2OCH.sub.2CH.sub.2—, etc.

[0086] Animal parasite control agent: refers to an active compound that can effectively reduce the incidence of various parasites in animals infected by the parasites. Control: means that active compounds can effectively kill parasites and inhibit their growth or reproduction. Insecticide: a substance that has insecticidal efficacy on pests.

[0087] Acaricide: an agent used to control phytophagous mites.

SYNTHESIS EXAMPLES

[0088] According to the above-mentioned synthetic route, the compounds shown in Formula I of the present invention can be prepared by using different raw materials, respectively, regarding which further detailed description is as follows.

Example 1

Preparation of Compound 1

[0089] ##STR00006##

[0090] 0.50 g (0.90 mmol) of 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methyl-N-(2-oxo-2-(2,2,2-trifluoroethyeamino)ethylbenzamide, 25 mL of toluene, 0.18 g (1.80 mmol) of triethylamine, and finally 0.14 g (1.35 mmol) of cyclopropanecarbonyl chloride were added to a single-necked bottle, followed by heating to reflux and reacting for 3 h. Water was added to the reaction solution, which was then extracted with ethyl acetate, and the organic phase was dried over anhydrous magnesium sulfate, then filtered, concentrated, and purified by column chromatography to obtain 0.30 g of white solid.

[0091] The NMR and MS data of Compound 1 were as follows:

[0092] .sup.1H NMR (600 MHz, DMSO-d.sub.6) δ 8.82 (t, 1H), 7.81 (t, 1H), 7.69-7.60 (m, 4H), 7.54 (d, 1H), 4.47 (s, 2H), 4.39 (d, 1H), 4.30 (d, 1H), 3.99-3.88 (m, 2H), 2.38 (s, 3H), 1.77-1.68 (m, 1H), 0.84-0.64 (m, 4H). ESI-MS, m/Z: 646.24 [M+Na].sup.+.

Example 2

Preparation of Compound 2

[0093] ##STR00007##

[0094] Compound 2 (yellow solid) was prepared according to the synthesis method of Example 1. The NMR and MS data of Compound 2 were as follows:

[0095] .sup.1H NMR (600 MHz, DMSO-d.sub.6) δ 8.86 (t, 1H), 7.85 (d, 2H), 7.71-7.63 (m, 2H), 7.58 (d, 1H), 4.51 (s, 2H), 4.42 (d, 1H), 4.35 (d, 1H), 4.04-3.93 (m, 2H), 2.42 (s, 3H), 1.83-1.74 (m, 1H), 0.88-0.70 (m, 4H). ESI-MS, m/Z: 664.15 [M+Na].sup.+.

Example 3

Preparation of Compound 19

[0096] ##STR00008##

[0097] 0.50 g (0.90 mmol) of 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methyl-N-(2-oxo-2-(2,2,2-trifluoroethyeamino)ethylbenzamide, 20 mL of toluene, 0.18 g (1.80 mmol) of triethylamine, and finally 0.15 g (1.35 mmol) of methoxyacetyl chloride were added to a single-necked bottle, followed by heating to reflux and reacting for 3 h. Water was added to the reaction solution, which was then extracted with ethyl acetate, and the organic phase was dried over anhydrous magnesium sulfate, then filtered, concentrated, and purified by column chromatography to obtain 0.27 g of brown oily matter.

[0098] The NMR and MS data of Compound 19 were as follows: .sup.1H NMR (600 MHz, DMSO-d.sub.6) δ 8.75 (t, 1H), 7.82 (t, 1H), 7.68 (s, 1H), 7.66-7.60 (m, 3H), 7.50 (d, 1H), 4.38 (d, 1H), 4.32 (s, 2H), 4.31 (d, 1H),4.25 (s, 2H), 3.96-3.84 (m, 2H), 3.26 (s, 3H), 2.34 (s, 3H). ESI-MS, m/Z: 626.22 [M−H].sup.−.

Example 4

Preparation of Compound 20

[0099] ##STR00009##

[0100] Compound 20 (yellow solid) was prepared according to the synthesis method of Example 3. The NMR and MS data of Compound 20 were as follows:

[0101] .sup.1H NMR (600 MHz, DMSO-d.sub.6) δ 8.74 (t, 1H), 7.80 (d, 2H), 7.68-7.65 (m, 1H), 7.63-7.59 (m, 1H), 7.49 (d, 1H), 4.39-4.28 (m, 4H), 4.24 (s, 2H), 3.94-3.85 (m, 2H), 3.26 (s, 3H), 2.33 (s, 3H). ESI-MS, m/Z: 668.11 [M+Na].sup.+.

Example 5

Preparation of Compound 21

[0102] ##STR00010##

[0103] Compound 21 (brown oily matter) was prepared according to the synthesis method of Example 3. The NMR and MS data of Compound 21 were as follows:

[0104] .sup.1H NMR (600 MHz, DMSO-d.sub.6) δ 8.75 (t, 1H), 7.81 (t, 1H), 7.68-7.59 (m, 4H), 7.48 (d, 1H), 4.38 (d, 1H), 4.35 (s, 2H), 4.29 (d, 1H), 4.24 (s, 2H), 3.94-3.84 (m, 2H), 3.45 (q, 2H), 2.33 (s, 3H), 1.09 (t, 3H). ESI-MS, m/Z: 664.36 [M+Na].sup.+.

Example 6

Preparation of Compound 22

[0105] ##STR00011##

[0106] Compound 22 (brown oily matter) was prepared according to the synthesis method of Example 3. The NMR data of Compound 22 was as follows:

[0107] .sup.1H NMR (600 MHz, DMSO-d.sub.6) δ 8.75 (t, 1H), 7.80 (d, 2H), 7.66 (d, 1H), 7.61 (dd, 1H), 7.49 (d, 1H), 4.41-4.28 (m, 4H), 4.25 (s, 2H), 3.95-3.85 (m, 2H), 3.45 (q, 2H), 2.33 (s, 3H), 1.09 (t, 3H).

Example 7

Preparation of Compound 27

[0108] ##STR00012##

[0109] Compound 27 (brown oily matter) was prepared according to the synthesis method of Example 3. The NMR and MS data of Compound 27 were as follows:

[0110] .sup.1H NMR (600 MHz, DMSO-d.sub.6) δ 8.75 (t, 1H), 7.82 (t, 1H), 7.68 (d, 1H), 7.66-7.59 (m, 3H), 7.49 (d, 1H), 4.41-4.35 (m, 3H), 4.31 (d, 1H), 4.25 (s, 2H), 3.95-3.84 (m, 2H), 3.41 (t, 2H), 2.34 (s, 3H), 1.52-1.43 (m, 2H), 1.36-1.27 (m, 2H), 0.87 (t, 3H). ESI-MS, m/Z: 692.34 [M+Na].sup.+.

Example 8

Preparation of Compound 31

[0111] ##STR00013##

[0112] Compound 31 (brown oily matter) was prepared according to the synthesis method of Example 3. The NMR data of Compound 31 was as follows:

[0113] .sup.1H NMR (600 MHz, DMSO-d.sub.6) δ 8.80 (t, 1H), 7.81 (t, 1H), 7.68-7.59 (m, 4H), 7.45 (d, 1H), 4.42-4.26 (m, 4H), 3.97-3.87 (m, 2H), 3.50 (t, 2H), 3.18 (s, 3H), 2.79 (t, 2H), 2.33 (s, 3H).

Example 9

Preparation of Compound 33

[0114] ##STR00014##

[0115] Compound 33 (brown oily matter) was prepared according to the synthesis method of Example 3. The NMR and MS data of Compound 33 were as follows:

[0116] .sup.1H NMR (600 MHz, DMSO-d.sub.6) δ 8.81 (t, 1H), 7.82 (t, 1H), 7.70-7.58 (m, 4H), 7.46 (d, 1H), 4.42-4.35 (m, 3H), 4.31 (d, 1H), 3.98-3.89 (m, 2H), 3.54 (t, 2H), 3.36 (q, 2H), 2.79 (t, 2H), 2.34 (s, 3H), 1.06 (t, 3H). ESI-MS, m/Z: 678.30 [M+Na].sup.+.

Example 10

Preparation of Compound 34

[0117] ##STR00015##

[0118] Compound 34 (brown oily matter) was prepared according to the synthesis method of Example 3. The NMR and MS data of Compound 34 were as follows:

[0119] .sup.1H NMR (600 MHz, DMSO-d.sub.6) δ 8.81 (t, 1H), 7.82 (d, 2H), 7.67-7.58 (m, 2H), 7.46 (d, 1H), 4.41-4.28 (m, 4H), 3.98-3.89 (m, 2H), 3.54 (t, 2H), 3.36 (q, 2H), 2.79 (t, 2H), 2.34 (s, 3H), 1.06 (t, 3H). ESI-MS, m/Z: 696.38 [M+Na].sup.+.

[0120] Other compounds as shown in Formula I of the present invention can be prepared according to the above examples.

Determination of Biological Activity

Example 11

Determination of Biological Activities Against Leucania Separata, Plutella Xylostella, and Chilo Suppressalis

[0121] The compounds of the invention were determined for the insecticidal activities against several insects. The determination method was as follows:

[0122] The compound to be determined was dissolved in a mixed solvent of acetone/methanol (1:1), followed by dilution with water containing 0.1% (wt) Tween 80 to a desired concentration.

[0123] The activities of the respective compounds against Leucania separata, Plutella xylostella, and Chilo suppressalis were determined by Airbrush spraying method.

(1) Determination of the Insecticidal Activity Against Leucania Separata

[0124] The determination method was as follows: Corn leaves were cut into 2 cm long segments; the pressure of Airbrush spraying was 10 psi (about 0.7 kg/cm.sup.2); both sides of each leaf segment were sprayed with 0.5 mL of the compound solution to be tested. After drying in the shade, ten 3.sup.nd instar larvae were inoculated for each treatment, and each treatment was replicated 3 times. After treatment, they were cultured in an observation room at a temperature of 25° C. and a relative humidity of 60-70%, and the number of surviving insects was examined and the mortality was calculated three days after administration.

[0125] Some test results against Leucania separata were as follows:

[0126] At the dose of 0.05 mg/L, the lethality rates of Compounds 1, 2, 19, 20, 21, 22, 27, 31, 33, and 34 to Leucania separata were all above 90% three days after administration.

(2) Determination of the Insecticidal Activity Against Plutella Xylostella

[0127] The determination method was as follows: Cabbage leaves were made into leaf discs with a diameter of 2 cm by using a hole puncher; the pressure of Airbrush spraying was 10 psi (about 0.7 kg/cm.sup.2); both sides of each leaf disc were sprayed with 0.5 mL of the compound solution to be tested. After drying in the shade, ten 3.sup.rd instar larvae were inoculated for each treatment, and each treatment was replicated 3 times. After treatment, they were cultured in an observation room at a temperature of 25° C. and a relative humidity of 60-70%, and the number of surviving insects was examined and the mortality was calculated three days after administration.

[0128] Some test results against Plutella xylostella were as follows:

[0129] At the dose of 0.313 mg/L, the lethality rates of Compounds 1, 2, 19, 20, 21, 22, 27, 31, 33, and 34 to Plutella xylostella were all above 90% three days after administration.

[0130] At the dose of 0.156 mg/L, the lethality rates of Compounds 19, 20, 21, 22, 27, 31, 33, and 34 to Plutella xylostella were all above 90% three days after administration.

[0131] Using KC1 as the control compound, Compounds 19 and 31 of the invention were selected for a parallel comparison test of the insecticidal activity against Plutella xylostella (3 days after administration). The determination method was the same as described above; the results were shown in Table 4:

TABLE-US-00004 TABLE 4 Parallel comparative test of insecticidal activities of Compounds 19, 31, and KC1 against Plutella xylostella Com- Mortality (%, 3 days after administration) pound 1.25 0.625 0.313 0.156 No. Formula mg/L mg/L mg/L mg/L 19 [00016] 100 100 100 100 31 [00017] 100 100 100 100 KC1 [00018] 100 70 36.67 20

[0132] As seen from Table 4, Compounds 19 and 31 of the present invention had higher and better insecticidal activity, when compared with the control compound KC1.

(3) Determination of the Insecticidal Activity Against Chilo Suppressalis

[0133] The determination method was as follows: 1) Preparation of rice seedlings: rice plants were cultivated in a plastic cup with a diameter of 4.5 cm and a height of 4 cm in a thermostatic chamber (temperature 26-28° C., relative humidity 60-80%, illumination 16 hL: 8 hD), and when the rice plants were developed to have 4-5 leaves, strong seedlings with identical growth vigour were selected for chemical treatment, and each treatment was replicated 3 times. 2) Preparation of insects to be tested: Chilo suppressalis, 3rd instar larvae, continuous lab rearing. 3) Inoculation of insects by spraying rice plant stems: The whole rice seedlings were sprayed evenly by using the spraying method, with 15 mL of the compound solution for each treatment. Firstly, the blank control was treated, and then the above procedure was replicated according to the order of test concentration from low to high. After rice seedlings were spray-treated, they were placed in the shade to dry, and the stems about 5 cm from the stem bases were cut off to feed the insects to be tested. Glass culture dishes with a diameter of 90 mm were prepared; each dish was padded with a filter paper at the bottom and added with water to keep moisture; about 5 rice stems were put into each dish and inoculated with 10 larvae, and each culture dish was then sealed with a non-woven and cultured in a thermostatic chamber. The number of residual live insects was examined 3 days after administration.

[0134] Some test results against Chilo suppressalis were as follows:

[0135] At the dose of 1 mg/L, the lethality rates of Compounds 1, 2, 19, 20, 21, 22, 27, 31, 33, and 34 to Chilo suppressalis were all above 90%.

[0136] At the dose of 0.5 mg/L, the lethality rates of Compounds 19, 21, 27, 31, and 33 to Chilo suppressalis were all above 90%.

[0137] Using KC1, KC2, KC3 as the control compounds, Compounds 1, 19, and 31 of the present invention were selected for a parallel comparison test of the insecticidal activity against Chilo suppressalis (3 days after administration), the determination method was the same as described above; the results were shown in Table 5:

TABLE-US-00005 TABLE 5 Parallel comparative test of insecticidal activities of Compounds 1, 19, 31, and KC1, KC2, and KC3 against Chilo suppressalis Com- Mortality (%, 3 days after administration) pound 5 1 0.5 0.25 No. Formula mg/L mg/L mg/L mg/L  1 [00019] 100 100 83.33 73.33 KC2 [00020] 100 100 53.33 0 KC3 [00021] 100 100 30 0 19 [00022] 100 100 100 86.67 31 [00023] 100 100 96.67 80 KC1 [00024] 10 0 0 0

[0138] As seen from Table 5, Compounds 1, 19, and 31 of the present invention had higher and better insecticidal activity, when compared with the control compounds KC1, KC2, and KC3. KC2 and KC3, in which R.sub.2 was methyl and ethyl, respectively, showed lower insecticidal activity, and KC1 in which R.sub.1 was methoxy showed almost no insecticidal activity, and however when R.sub.2 was alkoxyalkyl, KC1 showed significantly improved insecticidal activity.

Example 12

Determination of Biological Activity Against Tetranychus Cinnabarinus

[0139] The compounds of the invention were determined for the acaricidal activity in greenhouse. The determination method was as follows:

[0140] The compound to be determined was dissolved in acetone or dimethyl sulfoxide according to its solubility, and 0.1% Tween 80 solution was used to formulate 50 mL of the solution to be tested at a desired concentration, and the content of acetone or dimethyl sulfoxide in the solution did not exceed 10%.

[0141] A bean seedling with two true leaves was taken for inoculating 30-40 adult mites of Tetranychus cinnabarinus. After examining the cardinal number, the whole seedling was treated by spraying with a hand-held sprayer, each treatment being replicated 3 times, and then placed in a standard observation room. The number of surviving mites was examined after 72 hours, and the mortality was calculated.

[0142] The test results were as follows:

[0143] At the concentration of the solution of 5 mg/L, the lethality rates of Compounds 1, 2, 19, 20, 21, 22, 27, 31, 33, and 34 to Tetranychus cinnabarinus were all not less than 90%.

[0144] At the concentration of the solution of 5 mg/L, the control compound KC1 had no acaricidal activity (the mortality rate is 0) at the test dose, and the compound of the invention had unexpectedly high acaricidal activity.

Example 13

Insecticidal Test Against Cat Fleas

[0145] 4 mg of the compound to be tested was dissolved into 40 mL of acetone to obtain an acetone solution with a concentration of 100 ppm. 400 μL of the resultant solution was applied onto the bottom and side of a culture dish with an inner diameter of 5.3 cm, followed by standing until acetone was volatilized. A film of the compound of the invention was made on the inner wall of the culture dish. The inner wall of the used culture dish was 40 cm.sup.2 and was treated with a dose of 1 mg/cm.sup.2; and ten adult cat fleas (male and female mixed) were put into the culture dish, which then was covered and stored in a thermostatic chamber at 25° C. The number of dead insects was examined after 72 hours, and the mortality was calculated. The test was replicated 3 times. Test results: Compounds 1, 2, 19, 20, 21, 22, 27, 31, 33, 34 showed more than 90% mortality of insects.

Example 14

Insecticidal Test Against American Dog Ticks

[0146] 4 mg of the compound to be tested was dissolved into 40 mL of acetone to obtain an acetone solution with a concentration of 100 ppm. 400 μL of the resultant solution was applied onto the bottom and side of each of two culture dishes with an inner diameter of 5.3 cm, followed by standing until acetone was volatilized. A film of the compound of the invention was made on the inner wall of each culture dish. The inner wall of the used culture dish was 40 cm.sup.2 and was treated with a dose of 1 .sub.lag/cm.sup.2. Ten level 1 nymph (male and female mixed) of American dog ticks were put into each of the two culture dishes, and then the two culture dishes were combined and sealed at the joint with a tape to prevent escape, and then stored in a thermostatic chamber at 25° C. The number of dead insects was examined after 24 hours, and the mortality was calculated. The test was replicated 3 times. Test results: Compounds 1, 2, 19, 20, 21, 22, 27, 31, 33, 34 showed more than 90% mortality of insects.

INDUSTRIAL APPLICABILITY

[0147] The invention has disclosed an isoxazoline compound and the application thereof. The isoxazoline compound has unexpectedly excellent insecticidal and acaricidal efficacy, and also exhibits appropriate control efficacy on poisonous pests without phytotoxicity to cultivated crops and plants. In addition, the compounds of the present invention may be used to control, disinfect, and kill various pests, such as harmful piercing-sucking insects, chewing insects, and other plant parasitic pests, stored grain pests, sanitary pests, and the like.