BISAMIDE COMPOUND AND APPLICATION THEREOF

Abstract

This disclosure provides a bisamide compound and an application thereof, where the compound has a structure as shown by general formula I:

##STR00001##

the definition of each substituent in the formula is shown in the specification. The specification also discloses use thereof as an insecticide and an animal parasite control agent.

Claims

1-22. (canceled)

23. A bisamide compound, wherein the bisamide compound has a structure shown by general formula I: ##STR00033## In the general formula I: R.sub.1 is selected from halogen; R.sub.2 is selected from halogen, C.sub.1-C.sub.4 halogenoalkyl, and C.sub.1-C.sub.4 halogenoalkoxy; R.sub.3 is CF.sub.3 or CF.sub.2CF.sub.3; R.sub.4 is selected from fluorine, difluoromethyl, trifluoromethyl, and cyano.

24. The compound according to claim 23, wherein, in the formula I R.sub.1 is selected from halogen; R.sub.2 is selected from halogen, C.sub.1-C.sub.2 halogenoalkyl, and C.sub.1-C.sub.2 halogenoalkoxy; R.sub.3 is CF.sub.3 or CF.sub.2CF.sub.3; R.sub.4 is selected from fluorine, difluoromethyl, trifluoromethyl, and cyano.

25. The compound according to claim 24, wherein, in the formula I R.sub.1 is bromine or iodine; R.sub.2 is selected from bromine, iodine, trifluoromethyl, and difluoromethoxy; R.sub.3 is CF.sub.3 or CF.sub.2CF.sub.3; R.sub.4 is selected from fluorine, difluoromethyl, trifluoromethyl, and cyano.

26. The bisamide compound according to claim 23, wherein the bisamide compound is selected from: compounds in Table 1, wherein the compounds in Table 1 have a structure shown by the general formula I and R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as shown in Table 1: TABLE-US-00006 TABLE 1 Compound No. R.sub.1 R.sub.2 R.sub.3 R.sub.4 1 Br Br CF.sub.3 F 2 Br I CF.sub.3 F 3 Br CF.sub.3 CF.sub.3 F 4 I CF.sub.3 CF.sub.3 F 5 Br Br CF.sub.3 CF.sub.3 6 Br I CF.sub.3 CF.sub.3 7 Br CF.sub.3 CF.sub.3 CF.sub.3 8 I CF.sub.3 CF.sub.3 CF.sub.3 9 Br Br CF.sub.3 CN 10 Br I CF.sub.3 CN 11 Br CF.sub.3 CF.sub.3 CN 12 I CF.sub.3 CF.sub.3 CN 13 Br Br CF.sub.2CF.sub.3 F 14 Br I CF.sub.2CF.sub.3 F 15 Br CF.sub.3 CF.sub.2CF.sub.3 F 16 I CF.sub.3 CF.sub.2CF.sub.3 F 17 Br Br CF.sub.2CF.sub.3 CF.sub.3 18 Br I CF.sub.2CF.sub.3 CF.sub.3 19 Br CF.sub.3 CF.sub.2CF.sub.3 CF.sub.3 20 I CF.sub.3 CF.sub.2CF.sub.3 CF.sub.3 21 Br Br CF.sub.2CF.sub.3 CN 22 Br I CF.sub.2CF.sub.3 CN 23 Br CF.sub.3 CF.sub.2CF.sub.3 CN 24 I CF.sub.3 CF.sub.2CF.sub.3 CN

27. An intermediate compound for preparing the bisamide compound according to claim 23, wherein the intermediate compound is represented by general formula II: ##STR00034## Formula II In the general formula II: R.sub.1 is selected from halogen; R.sub.2 is selected from halogen, C.sub.1-C.sub.4 halogenoalkyl, and C.sub.1-C.sub.4 halogenoalkoxy; R.sub.3 is CF.sub.3 or CF.sub.2CF.sub.3.

28. The intermediate compound according to claim 27, wherein, in the general formula II, R.sub.1 is selected from halogen; R.sub.2 is selected from halogen, C.sub.1-C.sub.2 halogenoalkyl, and C.sub.1-C.sub.2 halogenoalkoxy; R.sub.3 is CF.sub.3 or CF.sub.2CF.sub.3.

29. The intermediate compound according to claim 28, wherein, in the general formula II, R.sub.1 is bromine or iodine; R.sub.2 is selected from bromine, iodine, trifluoromethyl, and difluoromethoxy; R.sub.3 is CF.sub.3 or CF.sub.2CF.sub.3.

30. The intermediate compound according to claim 29, wherein, the intermediate compound is selected from: compounds in Table 3, wherein the compounds in Table 3 have a structure shown by the general formula II and R.sub.1, R.sub.2, and R.sub.3 are as shown in Table 3: TABLE-US-00007 TABLE 3 Compound No. R.sub.1 R.sub.2 R.sub.3 II.1 Br Br CF.sub.3 II.2 Br I CF.sub.3 II.3 Br CF.sub.3 CF.sub.3 II.4 I CF.sub.3 CF.sub.3 II.5 Br Br CF.sub.2CF.sub.3 II.6 Br I CF.sub.2CF.sub.3 II.7 Br CF.sub.3 CF.sub.2CF.sub.3 II.8 I CF.sub.3 CF.sub.2CF.sub.3

31. An intermediate compound for preparing the bisamide compound according to claim 23, wherein the compound is shown by general formula III: ##STR00035## In the general formula III: R.sub.4 is selected from fluorine, difluoromethyl, trifluoromethyl, and cyano; L is selected from halogen and hydroxyl.

32. The intermediate compound according to claim 31, wherein, the intermediate compound is selected from: compounds in Table 4, wherein the compounds in Table 4 have a structure shown by the general formula III and R.sub.4 and L are as shown in Table 4: TABLE-US-00008 TABLE 4 Compound No. R.sub.4 L III.1 F F III.2 F Cl III.3 F Br III.4 F I III.5 F OH III.6 CF.sub.3 F III.7 CF.sub.3 Cl III.8 CF.sub.3 Br III.9 CF.sub.3 I III.10 CF.sub.3 OH III.11 CN F III.12 CN Cl III.13 CN Br III.14 CN I III.15 CN OH

33. Use of the bisamide compound according to claim 23 for preparing an insecticide.

34. The use according to claim 33, wherein the insecticide is used to control one or more of Leucania separata, Plutella xylostella, and Chilo suppressalis.

35. An insecticide formulation, wherein the insecticide formulation comprises the bisamide compound according to claim 23 as an active component, and also one or more adjuvants; and optionally, the amount of the bisamide compound according to claim 23 in the insecticide formulation is 0.1% to 99% by weight, further optionally, 0.5% to 90% by weight.

36. An insecticide composition, comprising a mixture of the bisamide compound according to claim 23 and another active compound, wherein the another active compound is one or more selected from an insecticide, a poison bait, a disinfectant, an acaricide, a nematicide, a fungicide, a growth regulator, and a herbicide.

37. A method for controlling an agricultural or forestry pest, comprising applying an effective dose of a material to the pest to be controlled or a growth medium thereof, wherein the material is one or more selected from the following group: the bisamide compound according to claim 23; the insecticide formulation; and the insecticide composition.

38. Use of the bisamide compound according to claim 23 for preparing an animal parasite control agent.

39. The use according to claim 38, wherein the animal parasite control agent is used to control one or more of cat fleas and American dog ticks.

40. An animal parasite control agent, comprising the bisamide compound according to claim 23 as an active component, and also one or more adjuvants; and optionally, the amount of the bisamide compound according to claim 1 in the animal parasite control agent is 1% to 80% by weight.

41. An animal parasite control composition, comprising a mixture of the bisamide compound according to claim 23 and another active animal parasite control compound, wherein the another active animal parasite control compound is one or more selected from an acaricide, an insecticide, a parasiticide, and antimalarial agent.

42. A method for controlling an animal parasite, comprising the step of applying an effective dose of a material to the animal parasite to be controlled or a growth medium thereof, wherein the material is one or more selected from the following group: the bisamide compound according to claim 23; the animal parasite control agent; and the animal parasite control composition.

Description

DETAILED DESCRIPTION

[0106] In order to make the objects, technical solutions, and advantages of the embodiments of this disclosure clearer, the technical solutions in the embodiments of this disclosure will be described clearly and completely below. It is apparent that the described embodiments are part of the embodiments of this disclosure, but not exhaustive. Based on the embodiments of this disclosure, all other embodiments obtained by those of ordinary skill in the art without creative work shall fall within the protection scope of this disclosure.

[0107] In addition, in order to better illustrate this disclosure, numerous specific details are given in the following specific embodiments. Those skilled in the art should understand that this disclosure may also be implemented without certain specific details. In some embodiments, the raw materials, elements, methods, means, or the like that are well known to those skilled in the art are not described in detail in order to highlight the gist of this disclosure.

[0108] Unless otherwise expressly stated, throughout the specification and claims, the term “comprise (comprising)” or a variation thereof such as “include (including)” or “contain (containing)” is construed as including the stated element or component, without excluding other elements or other components.

[0109] Unless otherwise noted, all starting materials used are commercially available.

[0110] In this disclosure, the terms used have the following meanings:

[0111] Halogen: fluorine, chlorine, bromine or iodine.

[0112] Halogenoalkyl: straight or branched chain alkyl, and the hydrogen atoms on these alkyl groups may be partially or completely replaced by halogens, such as difluoromethyl (CHF.sub.2), trifluoromethyl (CF.sub.3), or the like.

[0113] Halogenoalkoxy: The hydrogen atoms on the alkoxy group may be partially or completely replaced by halogen, such as difluoromethoxy (OCHF.sub.2), trifluoromethoxy (OCF.sub.3) or the like.

[0114] Cyano: CN.

[0115] Insecticide: a substance that has insecticidal effect on pests.

[0116] Animal parasite control agent: refers to an active compound that may effectively reduce the incidence of various parasites in animals infected by parasites. The “control” means that the active compound may effectively kill parasites, inhibit their growth or reproduction.

Synthesis Examples

[0117] According to the synthetic route described above, by using different starting material compounds, the compounds represented by the general formula I, general formula II and general formula III of this disclosure may be prepared separately, which are further specifically described as follows.

Example 1: Preparation of Intermediate Compound II.1

[0118] ##STR00007##

2.00 g (3.60 mmol) N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (the intermediate IV-1, prepared by referring to the method reported in WO2011093415 or WO2010018714), 0.74 g (5.35 mmol) of potassium carbonate and 0.58 g (4.30 mmol) of bromomethylcyclopropane were added into 60 ml of DMF, which was then heated to 100° C. for reaction. After the reaction was completed under monitoring by TLC, water and ethyl acetate were added for extraction, where the solvent in the organic phase was removed under reduced pressure, and the residue was purified by column chromatography to obtain 0.90 g of a white solid, which was the intermediate II.1.

[0119] The NMR and MS data of the intermediate II.1 are as follows:

[0120] .sup.1H NMR (600 MHz, Chloroform-d) δ 8.21 (d, 1H), 7.87 (s, 2H), 7.42-7.36 (m, 1H), 7.14 (t, 1H), 6.89 (td, 1H), 4.24-4.17 (br, 1H), 3.07-3.02 (m, 2H), 1.19-1.11 (m, 1H), 0.65-0.59 (m, 2H), 0.33-0.27 (m, 2H). LC-MS(m/z, ESI): 609.08[M+H].sup.+.

Example 2: Preparation of Intermediate Compound II.2

[0121] ##STR00008##

10 g of N-(2-bromo-6-iodo-4-heptafluoroisopropylphenyl)-2-fluoro-3-nitrobenzamide (prepared by referring to the method reported in CN109206335A), 15 g of anhydrous stannous chloride, 200 ml of 1,4-dioxane and 8 ml of concentrated hydrochloric acid were added, and then heated to 60° C. while being stirred for reaction. After the reaction was completed under monitoring by TLC, the organic solvent was distilled off under reduced pressure. 500 ml of ethyl acetate were added, and then an appropriate amount of saturated sodium hydroxide aqueous solution was added to adjust the pH=10. After thorough stirring, celite was used to filter out the precipitated insoluble matter. After the filtrate was extracted with ethyl acetate and water, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain a beige solid. The crude product was purified by column chromatography to obtain 7.91 g of N-(2-bromo-6-iodo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide, that is, intermediate IV-2.

[0122] 2.00 g (3.32 mmol) of N-(2-bromo-6-iodo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (the intermediate IV-2), 0.69 g (4.99 mmol) of potassium carbonate, and 0.54 g (4.00 mmol) of bromomethylcyclopropane were added to 60 ml of DMF, which was then heated to 100° C. for reaction. After the reaction was completed under monitoring by TLC, water and ethyl acetate were added for extraction, where the solvent in the organic phase was removed under reduced pressure, and the residue was purified by column chromatography to obtain 0.83 g of a white solid, which was the intermediate II.2.

[0123] The NMR and MS data of the intermediate II.2 are as follows:

[0124] .sup.1H NMR (600 MHz, Chloroform-d) δ 8.21 (d, 1H), 8.08 (d, 1H), 7.89 (d, 1H), 7.43-7.37 (m, 1H), 7.15 (t, 1H), 6.89 (td, 1H), 4.22 (br s, 1H), 3.07-3.02 (m, 2H), 1.20-1.12 (m, 1H), 0.66-0.59 (m, 2H), 0.33-0.28 (m, 2H). LC-MS(m/z, ESI): 657.07[M+H].sup.+.

Example 3: Preparation of Intermediate Compound II.3

[0125] ##STR00009##

[0126] 2.00 g (3.67 mmol) of N-(2-bromo-6-trifluoromethyl-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (intermediate IV-3, prepared by referring to the methods reported in WO2011093415, WO20110201687, WO2010013567, or WO2010018714), 0.76 g (5.50 mmol) of potassium carbonate, and 0.60 g (4.44 mmol) of bromomethylcyclopropane were added into 60 ml of DMF, which was then heated to 100° C. for reaction. After the reaction was completed under monitoring by TLC, water and ethyl acetate were added for extraction, where the solvent in the organic phase was removed under reduced pressure, and the residue was purified by column chromatography to obtain 0.73 g of a white solid, which was the intermediate II.3.

[0127] The NMR and MS data of the intermediate II.3 are as follows:

[0128] .sup.1H NMR (600 MHz, Chloroform-d) δ 8.27 (d, 1H), 8.14 (d, 1H), 7.91 (d, 1H), 7.41-7.35 (m, 1H), 7.14 (t, 1H), 6.89 (td, 1H), 4.25-4.17 (br, 1H), 3.07-3.02 (m, 2H), 1.20-1.11 (m, 1H), 0.66-0.58 (m, 2H), 0.33-0.27 (m, 2H). LC-MS(m/z, ESI): 599.07[M+H].sup.+.

Example 4: Preparation of Intermediate Compound II.4

[0129] ##STR00010##

[0130] According to the method described in Example 1, Example 2, or Example 3, the intermediate compound IV-4 (prepared by referring to the method reported in WO2011093415 or WO2010018714) was reacted with bromomethylcyclopropane to prepare the intermediate compound II.4 (white solid).

[0131] The NMR and MS data of the intermediate compound II.4 are as follows:

[0132] .sup.1H NMR (600 MHz, Chloroform-d) δ 8.38-8.27 (m, 2H), 7.96-7.91 (m, 1H), 7.41-7.35 (m, 1H), 7.15 (t, 1H), 6.92-6.86 (m, 1H), 4.22 (br s, 1H), 3.05 (d, 2H), 1.20-1.11 (m, 1H), 0.67-0.58 (m, 2H), 0.34-0.27 (m, 2H). LC-MS(m/z, ESI): 669.24[M+Na].sup.+.

Example 5: Preparation of Compound 1

[0133] ##STR00011##

[0134] 0.50 g (0.82 mmol) of the intermediate II.1 and 0.20 g (1.25 mmol) of the intermediate V-1 were added to 30 mL of toluene, which was then heated to reflux. After the reaction was completed under monitoring by TLC, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain 0.42 g of a yellow solid, which was the compound 1.

[0135] The NMR and MS data of the compound 1 are as follows:

[0136] .sup.1H NMR (600 MHz, Chloroform-d) δ 8.21 (s, 1H), 8.08 (t, 1H), 8.03-7.92 (br, 1H), 7.91-7.76 (m, 3H), 7.54 (t, 1H), 7.33 (t, 1H), 6.81 (s, 1H), 3.90 (s, 1H), 3.74 (s, 1H), 1.17-1.05 (br, 1H), 0.59-0.43 (m, 2H), 0.19 (d, 2H). LC-MS(m/z, ESI): 732.11[M+H].sup.+.

Example 6: Preparation of Compound 2

[0137] ##STR00012##

[0138] 0.60 g (0.91 mmol) of the intermediate II.2 and 0.22 g (1.38 mmol) of the intermediate V-1 were added to 40 mL of toluene, which was then heated to reflux. After the reaction was completed under monitoring by TLC, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain 0.46 g of a white solid, which was the compound 2.

[0139] The NMR and MS data of the compound 2 are as follows:

[0140] .sup.1H NMR (600 MHz, Chloroform-d) δ 8.22 (s, 1H), 8.13-8.04 (m, 2H), 7.96 (d, 1H), 7.88 (d, 1H), 7.85-7.77 (br, 1H), 7.60-7.51 (m, 1H), 7.35 (t, 1H), 6.80 (s, 1H), 3.94 (s, 1H), 3.72 (s, 1H), 1.17-1.05 (br, 1H), 0.58-0.46 (m, 2H), 0.19 (d, 2H). LC-MS(m/z, ESI): 780.11[M+H].sup.+.

Example 7: Preparation of Compound 3

[0141] ##STR00013##

[0142] 0.50 g (0.83 mmol) of the intermediate II.3 and 0.20 g (1.25 mmol) of the intermediate V-1 were added to 30 mL of toluene, which was then heated to reflux. After the reaction was completed under monitoring by TLC, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain 0.45 g of a white solid, which was the compound 3.

[0143] The NMR and MS data of the compound 3 are as follows:

[0144] .sup.1H NMR (600 MHz, Chloroform-d) δ 8.18 (s, 1H), 8.13 (d, 1H), 8.07 (t, 1H), 8.00 (d, 1H), 7.90 (d, 1H), 7.87-7.79 (br, 1H), 7.62-7.53 (m, 1H), 7.35 (t, 1H), 6.82 (s, 1H), 3.96 (s, 1H), 3.70 (s, 1H), 1.17-1.05 (br, 1H), 0.58-0.46 (m, 2H), 0.18 (d, 2H). LC-MS(m/z, ESI): 722.10[M+H].sup.+.

Example 8: Preparation of Compound 4

[0145] ##STR00014##

[0146] According to the method described in Example 5, Example 6, or Example 7, the intermediate compound II.4 was reacted with the intermediate V-1 to prepare the compound 4 (yellow solid). The NMR and MS data of the compound 4 are as follows:

[0147] .sup.1H NMR (600 MHz, Chloroform-d) δ 8.35-8.31 (m, 1H), 8.18 (s, 1H), 8.11-8.00 (m, 2H), 7.95-7.90 (m, 1H), 7.89-7.78 (br, 1H), 7.58 (td, 1H), 7.36 (t, 1H), 6.82 (s, 1H), 4.05-3.89 (m, 1H), 3.75-3.60 (m, 1H), 1.17-1.05 (br, 1H), 0.60-0.44 (m, 2H), 0.18 (d, 2H). LC-MS(m/z, ESI): 770.18[M+H].sup.+.

Example 9: Preparation of Compound 7

[0148] ##STR00015##

[0149] According to the method described in Example 5, Example 6, or Example 7, the intermediate compound II.3 was reacted with the intermediate V-2 to prepare the compound 7 (yellow solid).

[0150] The NMR data of the compound 7 is as follows:

[0151] .sup.1H NMR (600 MHz, Chloroform-d) δ 8.64 (s, 1H), 8.13 (d, 1H), 8.08 (t, 1H), 7.98 (d, 1H), 7.92-7.84 (m, 1H), 7.65-7.53 (m, 2H), 7.37 (t, 1H), 4.08-3.95 (m, 1H), 3.77-3.65 (m, 1H), 1.18-1.07 (br, 1H), 0.61-0.47 (m, 2H), 0.21 (d, 2H).

Example 10: Preparation of Compound 8

[0152] ##STR00016##

[0153] According to the method described in Example 5, Example 6, or Example 7, the intermediate compound II.4 was reacted with the intermediate V-2 to prepare the compound 8 (yellow solid).

[0154] The NMR data of the compound 8 is as follows:

[0155] .sup.1H NMR (600 MHz, Chloroform-d) δ 8.65 (s, 1H), 8.32 (d, 1H), 8.08 (t, 1H), 8.02 (d, 1H), 7.94-7.90 (m, 1H), 7.88 (d, 1H), 7.61 (t, 1H), 7.56 (d, 1H), 7.37 (t, 1H), 4.10-3.96 (m, 1H), 3.75-3.63 (m, 1H), 1.19-1.08 (br, 1H), 0.61-0.46 (m, 2H), 0.21 (d, 2H).

Example 11: Preparation of Compound 9

[0156] ##STR00017##

[0157] According to the method described in Example 5, Example 6, or Example 7, the intermediate compound II.1 was reacted with the intermediate V-3 to prepare the compound 9 (white solid).

[0158] The NMR and MS data of the compound 9 are as follows:

[0159] .sup.1H NMR (600 MHz, Chloroform-d) δ 8.65 (s, 1H), 8.17-8.05 (br, 1H), 7.98-7.74 (m, 4H), 7.63-7.47 (m, 2H), 7.36 (t, 1H), 4.00-3.86 (m, 1H), 3.84-3.70 (m, 1H), 1.17-1.05 (br, 1H), 0.60-0.46 (m, 2H), 0.22 (d, 2H). LC-MS(m/z, ESI): 739.14[M+H].sup.+.

Example 12: Preparation of Compound 10

[0160] ##STR00018##

[0161] According to the method described in Example 5, Example 6, or Example 7, the intermediate compound II.2 was reacted with the intermediate V-3 to prepare the compound 10 (yellow oily matter).

[0162] The NMR and MS data of the compound 10 are as follows:

[0163] .sup.1H NMR (600 MHz, Chloroform-d) δ 8.66 (s, 1H), 8.16-8.08 (br, 1H), 8.07 (d, 1H), 7.94-7.86 (m, 2H), 7.83-7.77 (m, 1H), 7.61-7.51 (br, 2H), 7.37 (t, 1H), 4.02-3.89 (m, 1H), 3.81-3.68 (m, 1H), 1.17-1.06 (br, 1H), 0.60-0.48 (m, 2H), 0.22 (d, 2H). LC-MS(m/z, ESI): 787.20[M+H].sup.+.

Example 13: Preparation of Compound 11

[0164] ##STR00019##

[0165] According to the method described in Example 5, Example 6, or Example 7, the intermediate compound II.3 was reacted with the intermediate V-3 to prepare the compound 11 (yellow solid).

[0166] The NMR and MS data of the compound 11 are as follows:

[0167] .sup.1H NMR (600 MHz, Chloroform-d) δ 8.62 (s, 1H), 8.16-8.12 (m, 1H), 8.09 (t, 1H), 8.00-7.89 (m, 2H), 7.82 (d, 1H), 7.63-7.52 (m, 2H), 7.37 (t, 1H), 4.02-3.92 (m, 1H), 3.78-3.67 (m, 1H), 1.17-1.05 (br, 1H), 0.60-0.47 (m, 2H), 0.21 (d, 2H). LC-MS(m/z, ESI): 729.11[M+H].sup.+.

Example 14: Preparation of Compound 12

[0168] ##STR00020##

[0169] According to the method described in Example 5, Example 6, or Example 7, the intermediate compound II.4 was reacted with the intermediate V-3 to prepare the compound 12 (yellow solid).

[0170] The NMR and MS data of the compound 12 are as follows:

[0171] .sup.1H NMR (600 MHz, Chloroform-d) δ 8.62 (s, 1H), 8.37-8.31 (m, 1H), 8.09 (t, 1H), 8.00 (d, 1H), 7.93 (d, 1H), 7.81 (d, 1H), 7.63-7.53 (m, 2H), 7.37 (t, 1H), 4.05-3.94 (m, 1H), 3.77-3.64 (m, 1H), 1.17-1.05 (br, 1H), 0.61-0.47 (m, 2H), 0.21 (d, 2H). LC-MS(m/z, ESI): 777.21[M+H].sup.+.

[0172] With reference to the above examples, other compounds of the general formula I of the present invention can be prepared.

[0173] Determination of Biological Activity

Example 15: Determination of Biological Activities Against Leucania separata, Plutella xylostella, and Chilo suppressalis

[0174] The compounds of the invention were determined for the insecticidal activities against several insects. The determination method was as follows:

[0175] After being dissolved in a mixed solvent of acetone/methanol (1:1), the test compound was diluted with water containing 0.1% (wt) Tween 80 to the desired concentration.

[0176] With Leucania separata, Plutella xylostella, and Chilo suppressalis as targets, airbrush spray method was used for the determination of activity.

[0177] (1) Determination of the Insecticidal Activity Against Leucania separata

[0178] Determination method: Corn leaves were cut into 2 cm leaf sections, and Airbrush spray treatment was carried out at a pressure of 10 psi (approximately 0.7 kg/cm.sup.2) on the front and back sides of each leaf section, with a spray volume of the compound to be tested of 0.5 ml. After drying in the shade, 10 of 3rd instar larvae were introduced for each treatment, and each treatment was repeated 3 times. After the treatment, it was placed in an observation room at 25° C. and a relative humidity of 60-70%, and 3 days after the treatment, the number of surviving insects was investigated, and the mortality rate was calculated.

[0179] Some of the determination results against Leucania separata were as follows:

[0180] At a dose of 0.05 mg/L, 3 days after the treatment, the lethality rates of compounds 1, 2, 3, 4, 7, 8, 9, 10, 11,12 against Leucania separata were all 90% or more.

[0181] (2) Determination of the Insecticidal Activity Against Plutella xylostella

[0182] Determination method: Cabbage leaves were punched into leaf discs with a diameter of 2 cm with a puncher, and Airbrush spray treatment was carried out at a pressure of 10 psi (approximately 0.7 kg/cm.sup.2) on the front and back sides of each leaf disc, with a spray volume of the compound to be tested of 0.5 ml. After drying in the shade, 10 of 3rd instar larvae were introduced for each treatment, and each treatment was repeated 3 times. After the treatment, it was placed in an observation room at 25° C. and a relative humidity of 60-70%, and 3 days after the treatment, the number of surviving insects was investigated, and the mortality rate was calculated.

[0183] Some of the determination results against Plutella xylostella were as follows:

[0184] At a dose of 0.5 mg/L, 3 days after the treatment, the lethality rates of compounds 1, 2, 3, 4, 7, 8, 9, 10, 11, 12 against Plutella xylostella were all 90% or more.

[0185] At a dose of 0.05 mg/L, 3 days after the treatment, the lethality rates of compounds 3, 4, 7, 8, 11, 12 against Plutella xylostella were all 90% or more.

[0186] (3) Determination of the Insecticidal Activity Against Chilo suppressalis

[0187] Determination method: 1) Preparation of Oryza sativa seedlings: Oryza sativa was cultivated in a constant temperature room (a temperature of 26-28V, a relative humidity of about 60-80%, and a light illumination of 16hL:8hD) in a small plastic cup with a diameter of 4.5 cm and a height of 4 cm, and when the Oryza sativa grew up to the 4-5 leaf stage, robust and consistent Oryza sativa seedlings were selected for chemical treatment, and 3 repetitions were performed for each treatment. 2) Preparation for test insects: Chilo suppressalis at 3rd instar larvae were raised continuously indoors. 3) The Oryza sativa stems were sprayed and insects were introduced. Spraying was performed uniformly on the whole plant of the Oryza sativa seedlings, with 15 ml of compound solution for each treatment. The blank control was treated first, and then the above operations were repeated in the order of the test concentration from low to high. After the Oryza sativa seedlings were sprayed, they were placed in a cool place to dry the liquid, and about 5 cm of stalks at the base of the stems were cut and fed to the test insects. A glass petri dish with a diameter of 90 mm was placed with filter paper at the bottom of the dish, and then was moisturized by adding water. After that, about 5 rice stalks and 10 larvae were placed in each dish, and the petri dish was sealed with a non-woven fabric and placed in a constant temperature room for cultivation. The number of remaining live insects was investigated 3 days after the treatment.

[0188] Some of the determination results on the Chilo suppressalis were as follows:

[0189] At a dose of 1 mg/L, the lethality rates of compounds 1, 2, 3, 4, 7, 8, 9, 10, 11, 12 against Chilo suppressalis were 90% or more.

[0190] At a dose of 0.5 mg/L, the lethality rates of compounds 3, 4, 7, 8, 11, 12 against Chilo suppressalis were 90% or more.

[0191] At a dose of 0.25 mg/L, the lethality rates of compounds 3, 4, 11, 12 against Chilo suppressalis were 90% or more.

[0192] The compounds 1, 3, 7, 11 of this disclosure and the comparative compounds were selected for a parallel comparison test of the insecticidal activity against Chilo suppressalis (3 days after the treatment), through a same determination method as that described above. The results were shown in Table 5:

TABLE-US-00005 TABLE 5 Parallel comparison test of the insecticidal activity of the compounds 1, 3, 7, 11 vs. the comparative compounds against Chilo suppressalis Com- Lethality rate (%, 3 days after the treatment) pound 10 1 0.5 0.25 No. Structural Formula mg/L mg/L mg/L mg/L 1 [00021] 100 100 73.33 46.67 1-1 [00022] 100 50 13.33 0 1-2 [00023] 0 0 — — 3 [00024] 100 100 100 100 2-1 [00025] 100 96.67 66.67 23.33 7 [00026] 100 100 93.33 70 3-1 [00027] 100 56.67 26.67 0 11 [00028] 100 100 100 100 4-1 [00029] 100 93.33 53.33 16.67 5-1 [00030] 16.67 0 — — 5-2 [00031] 70 33.33 0 — Note: ″—″ in the table means untested. In the table, 1-1, 1-2, 2-1, 3-1, 4-1, 5-1, 5-2 were all comparative compounds provided in this application. These comparative compounds may be obtained by referring to the methods of Examples 5-14 of this disclosure, and the starting materials may be prepared according to examples herein, or may be commercial available, or may be prepared according to conventional methods. [00032]

[0193] In the examples of this disclosure, by selecting the R.sub.1, R.sub.2, R.sub.3, R.sub.4 groups in the compound of formula I and combinations thereof, compounds with better insecticidal effects are obtained. As shown in Table 5, it may be seen by comparing the compound 1 with the comparative compounds 1-1 and 1-2, by comparing the compound 3 with the comparative compound 2-1, by comparing the compound 7 with the comparative compound 3-1, and by comparing the compound 11 with the comparative compound 4-1 that: R.sub.4 and its adjacent nitrogen atom are very important, and both of them cooperate with each other and are indispensable. When R.sub.4 is F, CF.sub.3, CN, and when the adjacent atom is a carbon atom, the compound has a significantly reduced, or even lost, effect on Chilo suppressalis. It may be seen by comparing compounds 3, 7, 11 with 5-1, 5-2 that when the atom adjacent to R.sub.4 is a nitrogen atom, and when R.sub.4 is hydrogen or chlorine, the compound also has a significantly reduced or even lost activity against Chilo suppressalis.

Example 16: Insecticidal Test on Cat Fleas

[0194] 4 mg of the test compound was dissolved in 40 ml of acetone to obtain an acetone solution with a concentration of 100 ppm. 400 μl of the compound solution was applied on the bottom and sides of a petri dish with an inner diameter of 5.3 cm, and then after the acetone was volatilized, a film of the compound of this disclosure was prepared on the inner wall of the petri dish. The petri dish used had an inner wall with an area of 40 cm.sup.2, and a treatment dose of 1 μg/cm.sup.2. It was then placed with 10 adult cat fleas (mixed male and female) therein, and after covered by the lid, it was stored in a constant temperature room at 25° C. The number of dead insects was checked after 72 h and the dead insect rate was calculated. The test was repeated 3 times. Test results: The compounds 1, 2, 3, 4, 7, 8, 9, 10, 11, 12 showed over 90% of mortality rate of the insects.

Example 17: Insecticidal Test on American Dog Ticks

[0195] 4 mg of the test compound was dissolved in 40 ml of acetone to obtain an acetone solution with a concentration of 100 ppm. 400 μl of the compound solution was applied on the bottom and sides of 2 petri dishes with an inner diameter of 5.3 cm, and then after the acetone was volatilized, a film of the compound of this disclosure was prepared on the inner wall of the petri dish. The petri dish used had an inner wall with an area of 40 cm.sup.2, and a treatment dose of 1 μg/cm.sup.2. It was then placed with 10 first nymphs of American dog ticks (mixed male and female) therein. After that, the 2 dishes were combined with an adhesive tape applied at the joint to prevent escaping of the insects, which was then stored in a constant temperature room at 25° C. The number of dead insects was checked after 24 h and the dead insect rate was calculated. The test was repeated 3 times. Test results: The compounds 1, 2, 3, 4, 7, 8, 9, 10, 11, 12 showed over 90% of mortality rate of the insects.

INDUSTRIAL APPLICABILITY

[0196] This disclosure provides a bisamide compound with an even better insecticidal activity. It may be used to prepare drugs for preventing and controlling pests in agriculture and other fields, and for preparing drugs for controlling animal parasites in the field of veterinary medicine.