ISOPHTHALAMINDE COMPOUND AND USE THEREOF

Abstract

This disclosure provides an isophthalamide compound and use thereof, wherein 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

1-24. (canceled)

25. An isophthalamide compound, wherein the isophthalamide compound has a structure shown by general formula I: ##STR00066## 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 cyano C.sub.1-C.sub.4 alkyl; R.sub.5 is selected from fluorine, difluoromethyl, and trifluoromethyl.

26. The compound according to claim 25, 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 CH.sub.2CN, CH.sub.2CH.sub.2CN, CH.sub.2CH.sub.2CH.sub.2CN, CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN, CH(CH.sub.3)CN, CH(CH.sub.2CH.sub.3)CN, CH(CH.sub.2CH.sub.2CH.sub.3)CN, C(CH.sub.3)(CH.sub.3)CN, and C(CH.sub.3)(CH.sub.2CH.sub.3)CN; R.sub.5 is selected from fluorine, difluoromethyl, and trifluoromethyl.

27. The isophthalamide compound according to claim 25, wherein the isophthalamide 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, R.sub.4, and R.sub.5 are as shown in Table 1: TABLE-US-00007 TABLE 1 Compound No. R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5  1 Br Br CF.sub.3 CH.sub.2CN F  2 Br Br CF.sub.3 CH.sub.2CH.sub.2CN F  3 Br Br CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN F  4 Br Br CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN F  5 Br I CF.sub.3 CH.sub.2CN F  6 Br I CF.sub.3 CH.sub.2CH.sub.2CN F  7 Br I CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN F  8 Br I CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN F  9 Br CF.sub.3 CF.sub.3 CH.sub.2CN F 10 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CN F 11 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN F 12 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN F 13 I CF.sub.3 CF.sub.3 CH.sub.2CN F 14 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CN F 15 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN F 16 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN F 17 Br Br CF.sub.3 CH.sub.2CN CF.sub.3 18 Br Br CF.sub.3 CH.sub.2CH.sub.2CN CF.sub.3 19 Br Br CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 20 Br Br CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 21 Br I CF.sub.3 CH.sub.2CN CF.sub.3 22 Br I CF.sub.3 CH.sub.2CH.sub.2CN CF.sub.3 23 Br I CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 24 Br I CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 25 Br CF.sub.3 CF.sub.3 CH.sub.2CN CF.sub.3 26 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CN CF.sub.3 27 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 28 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 29 I CF.sub.3 CF.sub.3 CH.sub.2CN CF.sub.3 30 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CN CF.sub.3 31 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 32 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 33 Br Br CF.sub.3 CH.sub.2CN CHF.sub.2 34 Br Br CF.sub.3 CH.sub.2CH.sub.2CN CHF.sub.2 35 Br Br CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 36 Br Br CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 37 Br I CF.sub.3 CH.sub.2CN CHF.sub.2 38 Br I CF.sub.3 CH.sub.2CH.sub.2CN CHF.sub.2 39 Br I CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 40 Br I CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 41 Br CF.sub.3 CF.sub.3 CH.sub.2CN CHF.sub.2 42 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CN CHF.sub.2 43 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 44 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 45 I CF.sub.3 CF.sub.3 CH.sub.2CN CHF.sub.2 46 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CN CHF.sub.2 47 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 48 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 49 Br Br CF.sub.2CF.sub.3 CH.sub.2CN F 50 Br Br CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN F 51 Br Br CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN F 52 Br Br CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN F 53 Br I CF.sub.2CF.sub.3 CH.sub.2CN F 54 Br I CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN F 55 Br I CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN F 56 Br I CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN F 57 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CN F 58 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN F 59 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN F 60 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN F 61 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CN F 62 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN F 63 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN F 64 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN F 65 Br Br CF.sub.2CF.sub.3 CH.sub.2CN CF.sub.3 66 Br Br CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN CF.sub.3 67 Br Br CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 68 Br Br CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 69 Br I CF.sub.2CF.sub.3 CH.sub.2CN CF.sub.3 70 Br I CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN CF.sub.3 71 Br I CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 72 Br I CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 73 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CN CF.sub.3 74 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN CF.sub.3 75 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 76 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 77 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CN CF.sub.3 78 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN CF.sub.3 79 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 80 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 81 Br Br CF.sub.2CF.sub.3 CH.sub.2CN CHF.sub.2 82 Br Br CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN CHF.sub.2 83 Br Br CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 84 Br Br CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 85 Br I CF.sub.2CF.sub.3 CH.sub.2CN CHF.sub.2 86 Br I CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN CHF.sub.2 87 Br I CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 88 Br I CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 89 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CN CHF.sub.2 90 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN CHF.sub.2 91 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 92 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 93 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CN CHF.sub.2 94 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN CHF.sub.2 95 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2 96 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CHF.sub.2

28. The isophthalamide compound according to claim 25, wherein the isophthalamide compound is selected from: compounds in Table 2, wherein the compounds in Table 2 have a structure shown by the general formula I and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as shown in Table 2: TABLE-US-00008 TABLE 2 Compound No. R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 1 Br Br CF.sub.3 CH.sub.2CN F 2 Br Br CF.sub.3 CH.sub.2CH.sub.2CN F 3 Br Br CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN F 4 Br Br CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN F 5 Br I CF.sub.3 CH.sub.2CN F 6 Br I CF.sub.3 CH.sub.2CH.sub.2CN F 7 Br I CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN F 8 Br I CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN F 9 Br CF.sub.3 CF.sub.3 CH.sub.2CN F 10 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CN F 11 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN F 12 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN F 13 I CF.sub.3 CF.sub.3 CH.sub.2CN F 14 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CN F 15 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN F 16 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN F 17 Br Br CF.sub.3 CH.sub.2CN CF.sub.3 18 Br Br CF.sub.3 CH.sub.2CH.sub.2CN CF.sub.3 19 Br Br CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 20 Br Br CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 21 Br I CF.sub.3 CH.sub.2CN CF.sub.3 22 Br I CF.sub.3 CH.sub.2CH.sub.2CN CF.sub.3 23 Br I CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 24 Br I CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 25 Br CF.sub.3 CF.sub.3 CH.sub.2CN CF.sub.3 26 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CN CF.sub.3 27 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 28 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 29 I CF.sub.3 CF.sub.3 CH.sub.2CN CF.sub.3 30 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CN CF.sub.3 31 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 32 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3

29. An intermediate compound for preparing the isophthalamide compound according to claim 25, wherein the intermediate compound is represented by general formula II: ##STR00067## 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; R.sub.4 is selected from cyano C.sub.1-C.sub.4 alkyl.

30. The intermediate compound according to claim 29, 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; R.sub.4 is selected from CH.sub.2CN, CH.sub.2CH.sub.2CN, CH.sub.2CH.sub.2CH.sub.2CN, CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN, CH(CH.sub.3)CN, CH(CH.sub.2CH.sub.3)CN, CH(CH.sub.2CH.sub.2CH.sub.3)CN, C(CH.sub.3)(CH.sub.3)CN, and C(CH.sub.3)(CH.sub.2CH.sub.3)CN.

31. The intermediate compound according to claim 30, wherein, the intermediate compound is selected from: compounds in Table 3, wherein the compounds of Table 3 have a structure shown by the general formula II and R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as shown in Table 3: TABLE-US-00009 TABLE 3 No. R.sub.1 R.sub.2 R.sub.3 R.sub.4 II.1 Br Br CF.sub.3 CH.sub.2CN II.2 Br Br CF.sub.3 CH.sub.2CH.sub.2CN II.3 Br Br CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN II.4 Br Br CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN II.5 Br I CF.sub.3 CH.sub.2CN II.6 Br I CF.sub.3 CH.sub.2CH.sub.2CN II.7 Br I CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN II.8 Br I CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN II.9 Br CF.sub.3 CF.sub.3 CH.sub.2CN II.10 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CN II.11 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN II.12 Br CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN II.13 I CF.sub.3 CF.sub.3 CH.sub.2CN II.14 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CN II.15 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN II.16 I CF.sub.3 CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN II.17 Br Br CF.sub.2CF.sub.3 CH.sub.2CN II.18 Br Br CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN II.19 Br Br CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN II.20 Br Br CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN II.21 Br I CF.sub.2CF.sub.3 CH.sub.2CN II.22 Br I CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN II.23 Br I CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN II.24 Br I CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN II.25 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CN II.26 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN II.27 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN II.28 Br CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN II.29 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CN II.30 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CN II.31 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CN II.32 I CF.sub.3 CF.sub.2CF.sub.3 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN

32. An intermediate compound for preparing the isophthalamide compound according to claim 25, wherein the compound is represented by general formula III: ##STR00068## In the general formula III: R.sub.4 is selected from cyano C.sub.1-C.sub.4 alkyl; R.sub.5 is selected from fluorine, difluoromethyl, and trifluoromethyl; L is selected from halogen and hydroxyl.

33. The intermediate compound according to claim 32, wherein, in the general formula III, R.sub.4 is selected from CH.sub.2CN, CH.sub.2CH.sub.2CN, CH.sub.2CH.sub.2CH.sub.2CN, CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN, CH(CH.sub.3)CN, CH(CH.sub.2CH.sub.3)CN, CH(CH.sub.2CH.sub.2CH.sub.3)CN, C(CH.sub.3)(CH.sub.3)CN, and C(CH.sub.3)(CH.sub.2CH.sub.3)CN; R.sub.5 is selected from fluorine, difluoromethyl, and trifluoromethyl; L is selected from halogen and hydroxyl.

34. The intermediate compound according to claim 33, wherein, the intermediate compound is selected from: compounds in Table 4, wherein the compounds of Table 4 have a structure shown by the general formula III and R.sub.4, R.sub.5, and L are as shown in Table 4: TABLE-US-00010 TABLE 4 No. R.sub.4 R.sub.5 L III.1 CH.sub.2CN F Cl III.2 CH.sub.2CH.sub.2CN F Cl III.3 CH.sub.2CH.sub.2CH.sub.2CN F Cl III.4 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN F Cl III.5 CH.sub.2CN F OH III.6 CH.sub.2CH.sub.2CN F OH III.7 CH.sub.2CH.sub.2CH.sub.2CN F OH III.8 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN F OH III.9 CH.sub.2CN CF.sub.3 Cl III.10 CH.sub.2CH.sub.2CN CF.sub.3 Cl III.11 CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 Cl III.12 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 Cl III.13 CH.sub.2CN CF.sub.3 OH III.14 CH.sub.2CH.sub.2CN CF.sub.3 OH III.15 CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 OH III.16 CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN CF.sub.3 OH

35. Use of the isophthalamide compound according to claim 25 for preparing an insecticide.

36. The use according to claim 35, wherein the insecticide is used to control one or more of Leucania separata, Plutella xylostella, and Chilo suppressalis.

37. An insecticide formulation, wherein the insecticide formulation comprises the isophthalamide compound according to claim 25 as an active component, and also one or more adjuvants; and optionally, the amount of the isophthalamide compound according to claim 25 in the insecticide formulation is 0.1% to 99% by weight, further optionally, 0.5% to 90% by weight.

38. An insecticide composition, comprising a mixture of the isophthalamide compound according to claim 25 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.

39. 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 isophthalamide compound according to claim 25; the insecticide formulation; and the insecticide composition.

40. Use of the isophthalamide compound according to claim 25 for preparing an animal parasite control agent.

41. The use according to claim 40, wherein the animal parasite control agent is used to control one or more of cat fleas and American dog ticks.

42. An animal parasite control agent, comprising the isophthalamide compound according to claim 25 as an active component, and also one or more adjuvants; and optionally, the amount of the isophthalamide compound according to claim 1 in the animal parasite control agent is 1% to 80% by weight.

43. An animal parasite control composition, comprising a mixture of the isophthalamide compound according to claim 25 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.

44. 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 isophthalamide according to claim 25; the animal parasite control agent; and the animal parasite control composition.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0125] 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.

[0126] 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.

[0127] 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.

[0128] Unless otherwise noted, all starting materials used are commercially available.

[0129] In this disclosure, the terms used have the following meanings:

[0130] Halogen: fluorine, chlorine, bromine or iodine.

[0131] 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.

[0132] 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.

[0133] Cyanoalkyl: straight or branched chain alkyl, and the hydrogen atoms on these alkyl groups may be partially or completely replaced by cyano groups. C.sub.1-C.sub.4 in the cyano C.sub.1-C.sub.4 alkyl group represent the chain length of the alkyl, for example CH.sub.2CN, CH.sub.2CH.sub.2CN, CH.sub.2CH.sub.2CH.sub.2CN, CH.sub.2CH.sub.2CH.sub.2CH.sub.2CN, CH(CH.sub.3)CN, CH(CH.sub.2CH.sub.3)CN, CH(CH.sub.2CH.sub.2CH.sub.3)CN, C(CH.sub.3)(CH.sub.3)CN or C(CH.sub.3)(CH.sub.2CH.sub.3)CN.

[0134] Insecticide: a substance that has insecticidal effect on pests.

[0135] 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

[0136] 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

[0137] ##STR00008##

[0138] 1.00 g (1.80 mmol) of N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (intermediate IV-1, prepared by referring to the method reported in WO2011093415 or WO2010018714), 0.37 g (2.68 mmol) of potassium carbonate, 0.27 g (1.80 mmol) of sodium iodide and 0.26 g (2.19 mmol) of bromoacetonitrile were added into 30 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 0.50 g of a white solid, which was the intermediate II.1. The NMR and MS data of the intermediate II.1 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.11 (d, 1H), 7.88 (s, 2H), 7.64-7.58 (m, 1H), 7.29 (t, 1H), 7.05 (td, 1H), 4.52-4.44(br, 1H), 4.24 (d, 2H). LC-MS(m/z, ESI): 594.01 (M+H).sup.+.

Example 2

Preparation of Intermediate Compound II.2

[0139] ##STR00009##

[0140] 1.50 g (2.70 mmol) of N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (intermediate IV-1), 0.56 g (4.05 mmol) of potassium carbonate, 0.41 g (2.74 mmol) of sodium iodide and 0.43 g (3.21 mmol) of bromopropionitrile were added to 50 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 0.25 g of a white solid, which was the intermediate II.2. The NMR and MS data of the intermediate II.2 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.16 (d, 1H), 7.87 (s, 2H), 7.52-7.46 (m, 1H), 7.20 (t, 1H), 6.90 (td, 1H), 4.46-4.40 (m, 1H), 3.66-3.60 (m, 2H), 2.72 (t, 2H). LC-MS (m/z, ESI): 608.01 (M+H).sup.+.

Example 3

Preparation of Intermediate Compound II.3

[0141] ##STR00010##

[0142] 1.00 g (1.80 mmol) of N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (intermediate IV-1), 0.37 g (2.68 mmol) of potassium carbonate, 0.27 g (1.80 mmol) of sodium iodide and 0.32 g (2.16 mmol) of bromobutyronitrile were added to 30 ml 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 0.12 g of a white solid, which was the intermediate II.3. The NMR and MS data of Intermediate II.3 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.16 (d, 1H), 7.87 (s, 2H), 7.46-7.42 (m, 1H), 7.18 (t, 1H), 6.94 (td, 1H), 4.17-4.10 (m, 1H), 3.43 (q, 2H), 2.54 (t, 2H), 2.08-2.02 (m, 2H). LC-MS (m/z, ESI): 622.03 (M+H).sup.+.

Example 4

Preparation of Intermediate Compound II.4

[0143] ##STR00011##

[0144] 1.00 g (1.80 mmol) of N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (intermediate IV-1), 0.37 g (2.68 mmol) of potassium carbonate, 0.27 g (1.80 mmol) of sodium iodide and 0.35 g (2.16 mmol) of bromovaleronitrile were added to 30 ml 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 0.11 g of a white solid, which was the intermediate II.4. The NMR and MS data of the intermediate II.4 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.19 (d, 1H), 7.87 (s, 2H), 7.40 (t, 1H), 7.16 (t, 1H), 6.90 (t, 1H), 4.07 (s, 1H), 3.31-3.23 (m, 2H), 2.44 (t, 2H), 1.91-1.78 (m, 4H). LC-MS (m/z, ESI): 636.10 (M+H).sup.+.

Example 5

Preparation of Intermediate Compound II.5

[0145] ##STR00012##

[0146] 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 60V 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 (intermediate IV-2).

[0147] 1.00 g (1.66 mmol) of N-(2-bromo-6-iodo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (intermediate IV-2), 0.34 g (2.46 mmol) of potassium carbonate, 0.25 g (1.67 mmol) of sodium iodide and 0.24 g (2.00 mmol) of bromoacetonitrile were added to 30 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 0.43 g of a white solid, which was the intermediate II.5. The NMR and MS data of the intermediate II.5 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.12 (d, 1H), 8.08 (d, 1H), 7.90 (d, 1H), 7.61 (t, 1H), 7.29 (t, 1H), 7.05 (td, 1H), 4.54-4.47 (br, 1H), 4.24 (d, 2H). LC-MS (m/z, ESI): 642.05 (M+H).sup.+.

Example 6

Preparation of Intermediate Compound II.6

[0148] ##STR00013##

[0149] 2.00 g (3.32 mmol) of N-(2-bromo-6-iodo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (intermediate IV-2), 0.69 g (4.99 mmol) of potassium carbonate, 0.50 g (3.34 mmol) of sodium iodide and 0.53 g (3.96 mmol) of bromopropionitrile 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 0.26 g of a white solid, which was the intermediate II.6. The NMR and MS data of Intermediate II.6 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.17 (d, 1H), 8.08 (d, 1H), 7.90 (d, 1H), 7.50 (t, 1H), 7.20 (t, 1H), 6.91 (td, 1H), 4.48-4.40 (m, 1H), 3.63 (q, 2H), 2.72 (t, 2H). LC-MS (m/z, ESI): 656.07 (M+H).sup.+.

Example 7

Preparation of Intermediate Compound II.9

[0150] ##STR00014##

[0151] 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 method reported in WO2011093415 or WO2010018714), 0.76 g (5.50 mmol) of potassium carbonate, 0.56 g (3.74 mmol) of sodium iodide and 0.53 g (4.42 mmol) of bromoacetonitrile 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 0.78 g of a white solid, which was the intermediate II.9. The NMR and MS data of Intermediate II.9 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.18 (d, 1H), 8.16-8.13 (m, 1H), 7.94-7.90 (m, 1H), 7.63-7.55 (m, 1H), 7.29 (t, 1H), 7.05 (td, 1H), 4.52-4.45 (m, 1H), 4.24 (d, 2H). LC-MS (m/z, ESI): 584.04 (M+H).sup.+.

Example 8

Preparation of Intermediate Compound II.10

[0152] ##STR00015##

[0153] 2.00 (3.67 mmol) of N-(2-bromo-6-trifluoromethyl-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (intermediate IV-3), 0.76 g (5.50 mmol) of potassium carbonate, 0.55 g (3.67 mmol) of sodium iodide and 0.59 g (4.40 mmol) of bromopropionitrile 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 0.22 g of a white solid, which was the intermediate II.10. The NMR and MS data of Intermediate II.10 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.22 (d, 1H), 8.16-8.13 (m, 1H), 7.93-7.90 (m, 1H), 7.50-7.45 (m, 1H), 7.20 (t, 1H), 6.91 (td, 1H), 4.46-4.38 (m, 1H), 3.63 (q, 2H), 2.72 (t, 2H). LC-MS (m/z, ESI): 598.05 (M+H).sup.+.

Example 9

Preparation of Intermediate Compound II.11

[0154] ##STR00016##

[0155] 1.30 (2.39 mmol) of N-(2-bromo-6-trifluoromethyl-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (intermediate IV-3), 0.49 g (3.55 mmol) of potassium carbonate, 0.36 g (2.40 mmol) of sodium iodide and 0.46 g (3.13 mmol) of bromobutyronitrile were added to 40 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 0.19 g of a white solid, which was the intermediate II.11. The NMR and MS data of Intermediate II.11 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.22 (d, 1H), 8.15-8.13 (m, 1H), 7.92-7.90 (m, 1H), 7.46-7.40 (m, 1H), 7.18 (t, 1H), 6.94 (td, 1H), 4.17-4.09 (m, 1H), 3.43 (q, 2H), 2.54 (t, 2H), 2.08-2.02 (m, 2H). LC-MS (m/z, ESI): 612.06 (M+H).sup.+.

Example 10

Preparation of Intermediate Compound II.12

[0156] ##STR00017##

[0157] 1.65 (3.03 mmol) of N-(2-bromo-6-trifluoromethyl-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (intermediate IV-3), 0.62 g (4.50 mmol) of potassium carbonate, 0.46 g (3.07 mmol) of sodium iodide, and 0.61 g (3.79 mmol) of bromovaleronitrile were added to 50 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 0.21 g of a white solid, which was the intermediate II.12. The NMR and MS data of Intermediate II.12 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.23 (d, 1H), 8.14 (d, 1H), 7.91 (d, 1H), 7.42-7.37 (m, 1H), 7.17 (t, 1H), 6.91 (td, 1H), 4.13-3.98 (m, 1H), 3.28 (t, 2H), 2.45 (t, 2H), 1.93-1.80 (m, 4H). LC-MS (m/z, ESI): 626.05 (M+H).sup.+.

Example 11

Preparation of Intermediate Compound II.13

[0158] ##STR00018##

[0159] According to the method described in Example 7, the intermediate compound IV-4 (prepared by referring to the method reported in WO2011093415 or WO2010018714) was reacted with bromoacetonitrile to prepare the intermediate compound II.13 (white solid). The NMR and MS data of the intermediate compound II.13 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.37-8.34 (m, 1H), 8.22 (d, 1H), 7.96-7.93 (m, 1H), 7.64-7.57 (m, 1H), 7.29 (t, 1H), 7.05 (td, 1H), 4.52-4.45 (m, 1H), 4.25 (d, 2H). LC-MS (m/z, ESI): 631.99 (M+H).sup.+.

Example 12

Preparation of Intermediate Compound II.14

[0160] ##STR00019##

[0161] According to the method described in Example 8, the intermediate compound IV-4 was reacted with bromopropionitrile to prepare the intermediate compound II.14 (white solid). The NMR and MS data of the intermediate compound II.14 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.36 (d, 1H), 8.26 (d, 1H), 7.94 (d, 1H), 7.51-7.46 (m, 1H), 7.21 (t, 1H), 6.92 (td, 1H), 4.47-4.39 (m, 1H), 3.64 (q, 2H), 2.72 (t, 2H). LC-MS (m/z, ESI): 646.02 (M+H).sup.+.

Example 13

Preparation of Intermediate Compound II.15

[0162] ##STR00020##

[0163] According to the method described in Example 9, the intermediate compound IV-4 was reacted with bromobutyronitrile to prepare the intermediate compound II.15 (white solid). The NMR and MS data of the intermediate compound II.15 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.36-8.34 (m, 1H), 8.27 (d, 1H), 7.95-7.92 (m, 1H), 7.45-7.40 (m, 1H), 7.18 (td, 1H), 6.94 (td, 1H), 4.18-4.11 (br s, 1H), 3.43 (q, 2H), 2.54 (t, 2H), 2.08-2.02 (m, 2H). LC-MS (m/z, ESI): 682.24 (M+Na).sup.+.

Example 14

Preparation of Intermediate Compound II.16

[0164] ##STR00021##

[0165] According to the method described in Example 10, the intermediate compound IV-4 was reacted with bromovaleronitrile to prepare the intermediate compound II.16 (white solid). The NMR and MS data of the intermediate compound II.16 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.35 (d, 1H), 8.28 (d, 1H), 7.93 (d, 1H), 7.43-7.38 (m, 1H), 7.17 (t, 1H), 6.91 (td, 1H), 4.22-3.90 (br s, 1H), 3.28 (t, 2H), 2.45 (t, 2H), 1.92-1.81 (m, 4H). LC-MS (m/z, ESI): 696.26 (M+Na).sup.+.

Example 15

Preparation of Compound 1

[0166] ##STR00022##

[0167] 0.30 g (0.51 mmol) of the intermediate II.1 and 0.12 g (0.76 mmol) of the intermediate V-1 were added to 20 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 0.26 g of a white solid, which was the compound 1. The NMR and MS data of the compound 1 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.24 (d, 1H), 8.16 (t, 1H), 7.98 (d, 1H), 7.91-7.85(m, 3H), 7.54 (td, 1H), 7.39 (t, 1H), 6.87 (dd, 1H), 4.95 (br s, 1H), 4.64 (br s, 1H). LC-MS (m/z, ESI): 717.04 (M+H).sup.+.

Example 16

Preparation of Compound 2

[0168] ##STR00023##

[0169] 0.30 g (0.49 mmol) of the intermediate II.2 and 0.12 g (0.75 mmol) of the intermediate V-1 were added to 20 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 0.24 g of a yellow solid, which was the compound 2. The NMR and MS data of the compound 2 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.23 (d, 1H), 8.06 (t, 1H), 7.93 (d, 1H), 7.88-7.80 (m, 3H), 7.64 (td, 1H), 7.39 (t, 1H), 6.83 (dd, 1H), 4.24-4.10 (m, 2H), 2.99 (br, 1H), 2.88 (br, 1H). LC-MS (m/z, ESI): 731.07 (M+H).sup.+.

Example 17

Preparation of Compound 3

[0170] ##STR00024##

[0171] 0.30 g (0.48 mmol) of the intermediate II.3 and 0.12 g (0.76 mmol) of the intermediate V-1 were added to 20 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 0.27 g of a yellow solid, which was the compound 3. The NMR and MS data of the compound 3 are as follows: .sup.1H NMR (600 MHz, Chloroform-d) δ 8.19 (d, 1H), 8.08 (t, 1H), 7.94 (d, 1H), 7.86 (s, 2H), 7.81 (td, 1H), 7.51 (td, 1H), 7.36 (t, 1H), 6.81 (dd, 1H), 4.16-3.98 (m, 2H), 2.54 (t, 2H), 2.16-2.01 (m, 2H). LC-MS (m/z, ESI): 745.11 (M+H).sup.+.

Example 18

Preparation of Compound 4

[0172] ##STR00025##

[0173] 0.30 g (0.47 mmol) of the intermediate II.4 and 0.11 g (0.69 mmol) of the intermediate V-1 were added to 20 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 0.25 g of a yellow solid, which was the compound 4. The NMR and MS data of the compound 4 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.18 (s, 1H), 8.10-8.00 (m, 2H), 7.85 (s, 2H), 7.78 (t, 1H), 7.49 (t, 1H), 7.36 (t, 1H), 6.80 (d, 1H), 4.25-4.10 (br, 1H), 3.91-3.80 (br, 1H), 2.54-2.36 (m, 2H), 1.90-1.76 (m, 4H). LC-MS (m/z, ESI): 759.13 (M+H).sup.+.

Example 19

Preparation of Compound 5

[0174] ##STR00026##

[0175] 0.30 g (0.47 mmol) of the intermediate II.5 and 0.11 g (0.69 mmol) of the intermediate V-1 were added to 20 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 0.23 g of a white solid, which was the compound 5. The NMR and MS data of the compound 5 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.25 (d, 1H), 8.17 (t, 1H), 8.07 (d, 1H), 7.97 (d, 1H), 7.91-7.85 (m, 2H), 7.56 (td, 1H), 7.41 (t, 1H), 6.86 (dd, 1H), 4.94 (br s, 1H), 4.65 (br s, 1H). LC-MS (m/z, ESI): 765.05 (M+H).sup.+.

Example 20

Preparation of Compound 6

[0176] ##STR00027##

[0177] 0.50 g (0.76 mmol) of the intermediate II.6 and 0.18 g (1.13 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 0.41 g of a white solid, which was the compound 6. The NMR and MS data of the compound 6 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.25 (d, 1H), 8.09 (t, 1H), 8.06 (d, 1H), 7.91 (d, 1H), 7.88 (d, 1H), 7.83 (td, 1H), 7.67 (td, 1H), 7.41 (t, 1H), 6.83 (dd, 1H), 4.22-4.13 (m, 2H), 3.08-2.96 (br, 1H), 2.94-2.81 (br, 1H). LC-MS (m/z, ESI): 778.96 (M+H).sup.+.

Example 21

Preparation of Compound 9

[0178] ##STR00028##

[0179] 0.50 g (0.86 mmol) of the intermediate II.9 and 0.21 g (1.32 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 0.47 g of a white solid, which was the compound 9. The NMR and MS data of the compound 9 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.21 (d, 1H), 8.17-8.12 (m, 2H), 8.01 (d, 1H), 7.92-7.85 (m, 2H), 7.57 (td, 1H), 7.41 (t, 1H), 6.88 (dd, 1H), 4.95 (br s, 1H), 4.63 (br s, 1H). LC-MS (m/z, ESI): 707.08 (M+H).sup.+.

Example 22

Preparation of Compound 10

[0180] ##STR00029##

[0181] 0.50 g (0.84 mmol) of the intermediate II.10 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 white solid, which was the compound 10. The NMR and MS data of the compound 10 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.24-8.19 (m, 1H), 8.14-8.11 (m, 1H), 8.05 (t, 1H), 7.94 (d, 1H), 7.90 (d, 1H), 7.87-7.81 (m, 1H), 7.68 (td, 1H), 7.41 (t, 1H), 6.85 (dd, 1H), 4.17 (t, 2H), 3.08-2.95 (br, 1H), 2.94-2.84 (br, 1H). LC-MS (m/z, ESI): 721.08 (M+H).sup.+.

Example 23

Preparation of Compound 11

[0182] ##STR00030##

[0183] According to the method described in Example 21, the intermediate compound II.11 was reacted with the intermediate compound V-1 to prepare the compound 11 (yellow solid). The NMR and MS data of the compound 11 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.16 (s, 1H), 8.14-8.12 (m, 1H), 8.09-8.04 (m, 1H), 7.98 (d, 1H), 7.92-7.89 (m, 1H), 7.82 (td, 1H), 7.54 (td, 1H), 7.37 (t, 1H), 6.83 (dd, 1H), 4.19-3.96 (m, 2H), 2.54 (t, 2H), 2.17-2.02 (m, 2H). LC-MS (m/z, ESI): 735.21 (M+H).sup.+.

Example 24

Preparation of Compound 12

[0184] ##STR00031##

[0185] According to the method described in Example 21, the intermediate compound II.12 was reacted with the intermediate V-1 to prepare the compound 12 (yellow solid). The NMR and MS data of the compound 12 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.19-8.09 (m, 3H), 8.04-7.99 (m, 1H), 7.91-7.88 (m, 1H), 7.82-7.77 (m, 1H), 7.51 (td, 1H), 7.37 (t, 1H), 6.82 (dd, 1H), 4.21 (br s, 1H), 3.84 (br s, 1H), 2.55-2.36 (m, 2H), 1.91-1.75 (m, 4H). LC-MS (m/z, ESI): 747.37 (M−H).sup.−.

Example 25

Preparation of Compound 13

[0186] ##STR00032##

[0187] According to the method described in Example 21, the intermediate compound II.13 was reacted with the intermediate V-1 to prepare the compound 13 (white solid). The NMR and MS data of the compound 13 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.34 (d, 1H), 8.22 (d, 1H), 8.19-8.13 (m, 1H), 8.03 (d, 1H), 7.93 (d, 1H), 7.91-7.85 (m, 1H), 7.59 (td, 1H), 7.42 (t, 1H), 6.87 (dd, 1H), 4.97 (br s, 1H), 4.64 (br s, 1H). LC-MS (m/z, ESI): 755.01 (M+H).sup.+.

Example 26

Preparation of Compound 14

[0188] ##STR00033##

[0189] According to the method described in Example 21, the intermediate compound II.14 was reacted with the intermediate V-1 to prepare the compound 14 (white solid). The NMR and MS data of the compound 14 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.33 (d, 1H), 8.21 (d, 1H), 8.06 (td, 1H), 8.00 (d, 1H), 7.93-7.90 (m, 1H), 7.86-7.81 (m, 1H), 7.69 (td, 1H), 7.42 (t, 1H), 6.84 (dd, 1H), 4.16 (t, 2H), 3.08-2.96 (br, 1H), 2.94-2.82 (br, 1H). LC-MS (m/z, ESI): 767.36 (M−H).sup.−.

Example 27

Preparation of Compound 15

[0190] ##STR00034##

[0191] According to the method described in Example 21, the intermediate compound II.15 was reacted with the intermediate V-1 to prepare the compound 15 (yellow solid). The NMR and MS data of the compound 15 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.34 (d, 1H), 8.17 (d, 1H), 8.10-7.98 (m, 2H), 7.93-7.91 (m, 1H), 7.82 (td, 1H), 7.55 (td, 1H), 7.41-7.36 (m, 1H), 6.82 (dd, 1H), 4.19-3.96 (m, 2H), 2.55 (t, 2H), 2.19-2.02 (m, 2H). LC-MS (m/z, ESI): 805.30 (M+Na).sup.+.

Example 28

Preparation of Compound 16

[0192] ##STR00035##

[0193] According to the method described in Example 21, the intermediate compound II.16 was reacted with the intermediate V-1 to prepare the compound 16 (yellow oily matter). The NMR and MS data of the compound 16 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.33 (d, 1H), 8.24-8.11 (m, 2H), 8.05-7.99 (m, 1H), 7.94-7.90 (m, 1H), 7.83-7.75 (m, 1H), 7.53 (td, 1H), 7.38 (t, 1H), 6.81 (d, 1H), 4.23 (br s, 1H), 3.84 (br s, 1H), 2.56-2.36 (m, 2H), 1.94-1.75 (m, 4H). LC-MS (m/z, ESI): 819.33 (M+Na).sup.+.

Example 29

Preparation of Compound 17

[0194] ##STR00036##

[0195] According to the method described in Example 15, the intermediate compound II.1 was reacted with the intermediate V-2 to prepare the compound 17 (white solid). The NMR and MS data of the compound 17 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.70 (s, 1H), 8.18 (t, 1H), 7.98-7.90(m, 2H), 7.87 (s, 2H), 7.63 (d, 1H), 7.57 (td, 1H), 7.41 (t, 1H), 4.99 (d, 1H), 4.66 (d, 1H). LC-MS (m/z, ESI): 767.06 (M+H).sup.+.

Example 30

Preparation of Compound 25

[0196] ##STR00037##

[0197] According to the method described in Example 21, the intermediate compound II.9 was reacted with the intermediate V-2 to prepare the compound 25 (yellow solid). The NMR and MS data of the compound 25 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.67 (s, 1H), 8.20-8.15 (m, 1H), 8.14 (d, 1H), 7.99-7.93 (m, 2H), 7.92-7.89 (m, 1H), 7.67-7.59(m, 2H), 7.44 (t, 1H), 4.99 (d, 1H), 4.68 (d, 1H). LC-MS (m/z, ESI): 779.28 (M+Na).sup.+.

Example 31

Preparation of Compound 26

[0198] ##STR00038##

[0199] According to the method described in Example 21, the intermediate compound II.10 was reacted with the intermediate V-2 to prepare the compound 26 (yellow solid). The NMR and MS data of the compound 26 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.67 (s, 1H), 8.13-8.11 (m, 1H), 8.07 (t, 1H), 7.96-7.87 (m, 3H), 7.71 (td, 1H), 7.60 (d, 1H), 7.43 (t, 1H), 4.25-4.15 (m, 1H), 3.08-2.98 (m, 1H), 2.94-2.84 (m, 1H). LC-MS (m/z, ESI): 793.33 (M+Na).sup.+.

Example 32

Preparation of Compound 27

[0200] ##STR00039##

[0201] According to the method described in Example 21, the intermediate compound II.11 was reacted with the intermediate compound V-2 to prepare the compound 27 (yellow solid). The NMR data of the compound 27 is as follows:

.SUP.1.H NMR (600 MHz, Chloroform-d) δ 8.62 (s, 1H), 8.13 (d, 1H), 8.07 (t, 1H), 7.99-7.93 (m, 1H), 7.91-7.85 (m, 2H), 7.61-7.55 (m, 2H), 7.39 (t, 1H), 4.20-4.11 (m, 1H), 4.09-4.00 (m, 1H), 2.56 (t, 2H), 2.19-2.03 (m, 2H).

Example 33

Preparation of Compound 28

[0202] ##STR00040##

[0203] According to the method described in Example 21, the intermediate compound II.12 was reacted with the intermediate V-2 to prepare the compound 28 (yellow solid). The NMR and MS data of the compound 28 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.62 (s, 1H), 8.15-8.06 (m, 2H), 8.03 (t, 1H), 7.91-7.87 (m, 1H), 7.85 (d, 1H), 7.62-7.50 (m, 2H), 7.39 (t, 1H), 4.33-4.21 (br, 1H), 3.90-3.78 (br, 1H), 2.56-2.37 (m, 2H), 1.92-1.76 (m, 4H). LC-MS (m/z, ESI): 821.36 (M+Na).sup.+.

Example 34

Preparation of Compound 29

[0204] ##STR00041##

[0205] According to the method described in Example 21, the intermediate compound II.13 was reacted with the intermediate V-2 to prepare the compound 29 (white solid). The NMR and MS data of the compound 29 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.68 (d, 1H), 8.34 (d, 1H), 8.20-8.14 (m, 1H), 8.02 (d, 1H), 7.97-7.91 (m, 2H), 7.67-7.61 (m, 2H), 7.45 (t, 1H), 4.98 (br s, 1H), 4.70 (br s, 1H). LC-MS (m/z, ESI): 827.31 (M+Na).sup.+.

Example 35

Preparation of Compound 32

[0206] ##STR00042##

[0207] According to the method described in Example 21, the intermediate compound II.16 was reacted with the intermediate V-2 to prepare the compound 32 (yellow solid). The NMR and MS data of the compound 32 are as follows:

.sup.1H NMR (600 MHz, Chloroform-d) δ 8.63 (s, 1H), 8.34-8.30 (m, 1H), 8.18-8.08 (br, 1H), 8.04 (t, 1H), 7.94-7.88 (m, 1H), 7.84 (d, 1H), 7.61-7.52 (m, 2H), 7.40 (t, 1H), 4.35-4.23 (m, 1H), 3.89-3.78 (m, 1H), 2.56-2.37 (m, 1H), 1.93-1.76 (m, 4H). LC-MS (m/z, ESI): 869.39 (M+Na).sup.+.

[0208] With reference to the above examples, other compounds of the general formula I of the present invention can be prepared.

Determination of Biological Activity

Example 36

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

[0209] The compounds of the invention were determined for the insecticidal activities against several insects. The determination method was as follows:

[0210] 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.

[0211] With Leucania separata, Plutella xylostella, and Chilo suppressalis as targets, airbrush spray method was used for the determination of the insecticidal activity.

[0212] (1) Determination of the Insecticidal Activity Against Leucania separata

[0213] 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 3.sup.rd 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.

[0214] Some of the determination results against Leucania separata were as follows:

[0215] At a dose of 0.05 mg/L, 3 days after the treatment, the lethality rates of compounds 1, 2, 3, 4, 5, 6, 9, 10, 11, 12, 13, 14, 15, 16, 17, 25, 26, 27, 28, 29, and 32 against Leucania separata were all 90% or more.

[0216] (2) Determination of the Insecticidal Activity Against Plutella xylostella

[0217] 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 for. 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.

[0218] Some of the determination results against Plutella xylostella were as follows:

[0219] At a dose of 1 mg/L, the lethality rates of compounds 1, 2, 3, 4, 5, 6, 9, 10, 11, 12, 13, 14, 15, 16, 17, 25, 26, 27, 28, 29, and 32 against Plutella xylostella were all 90% or more.

[0220] At a dose of 0.5 mg/L, the lethality rates of compounds 9, 10, 11, 12, 13, 14, 15, 16, 25, 26, 27, 28, 29, and 32 against Plutella xylostella were all 90% or more.

[0221] At a dose of 0.05 mg/L, the lethality rates of compounds 9, 10, 11, 12, 13, 14, 15, 16 against Plutella xylostella were all 90% or more.

[0222] The compounds 2, 10, 26 of this disclosure and the comparative compounds were selected for a parallel comparison test of the insecticidal activity against Plutella xylostella (3 days after the treatment), through the same test 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 2, 10, 26 vs. the comparative compounds against Plutella xylostella Lethality rate (%, 3 days after the treatment) Compound 5 1 0.5 0.05 No. Structural Formula mg/L mg/L mg/L mg/L  2 [00043] 100 100 86.67 43.33 1-1 [00044] 93.33 50 6.67 — 1-2 [00045] 90 30 0 — 1-3 [00046] 100 76.67 13.33 0 1-4 [00047] 60 10 — — 1-5 [00048] 83.33 60 33.33 0 CK1 [00049] 66.67 0 — — 1-6 [00050] 100 60 16.67 0 1-7 [00051] 100 73.33 20 0 10 [00052] 100 100 100 100 26 [00053] 100 100 96.67 73.33 2-1 [00054] 100 60 20 0 2-2 [00055] 100 93.33 30 0 2-3 [00056] 100 40 10 0 2-4 [00057] 100 90 63.33 33.33 2-5 [00058] 100 50 23.33 0 2-6 [00059] 100 90 60 20 2-7 [00060] 100 96.67 53.33 0 Note: ″—″ in the table means untested, which applies also to the followings. In the table, 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, and CKI were all comparative compounds provided in this application. These comparative compounds may be obtained by referring to the methods of Examples 15-35 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.

[0223] In the embodiments of this disclosure, by selecting the groups R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 in the compound of formula I and combinations thereof, compounds with better insecticidal effects may be obtained. As shown in Table 5, by comparing the compound 2 with the comparative compounds 1-1, 1-2, 1-3, 1-4, 1-5, CK1, 1-6, 1-7, and by comparing the compounds 10 , 26 with the comparative compounds 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, it may be seen that: only when R.sub.5 is F or CF.sub.3, if and only when the ring connected to R.sub.5 is the ring in this application, the corresponding compound (that is, the compound of general formula I) may exhibit a remarkably excellent insecticidal effect.

[0224] (3) Determination of the Insecticidal Activity Against Chilo suppressalis

[0225] 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 16 hL:8 hD) 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.

[0226] Some of the determination results on the Chilo suppressalis were as follows:

[0227] At a dose of 1 mg/L, the lethality rates of compounds 1, 2, 3, 4, 5, 6, 9, 10, 11, 12, 13, 14, 15, 16, 17, 25, 26, 27, 28, 29, and 32 against Chilo suppressalis were 90% or more.

[0228] At a dose of 0.5 mg/L, the lethality rates of compounds 9, 10, 11, 12, 13, 14, 15, 16, 25, 26, 27, 28, 29, and 32 against Chilo suppressalis were 90% or more.

[0229] At a dose of 0.25 mg/L, the lethality rates of compounds 9, 10, 11, 12, 13, 14, 15, 16, 25, 26, 29 against Chilo suppressalis were 90% or more.

[0230] The compounds 2, 10 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 6:

TABLE-US-00006 TABLE 6 Parallel comparison test of the insecticidal activity of the compounds 2, 10 vs. the comparative compounds against Chilo suppressalis Lethality rate (%, 3 days after the treatment) Compound 10 1 0.5 No. Structural Formula mg/L mg/L mg/L 2 [00061] 100 100 86.67 1-2 [00062] 0 0 — CK1 [00063] 13.33 0 — 10 [00064] 100 100 100 2-5 [00065] 70 23.33 0

[0231] In the embodiments of this disclosure, by selecting the groups R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 in the compound of formula I, compounds with better insecticidal effects may be obtained. As shown in Table 6, by comparing the compound 2 with the comparative compounds 1-2, CK1, and by comparing the compound 10 with the comparative compound 2-5, it may be seen that: only when R.sub.5 is F or CF.sub.3, if and only when the ring connected to R.sub.5 is the ring in this application, the corresponding compound (that is, the compound of general formula I) may exhibit a remarkably excellent insecticidal effect. Furthermore, the compound of this disclosure also has very good insecticidal activity at a lower dosage.

Example 37

Insecticidal Test on Cat Fleas

[0232] 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, 5, 6, 9, 10, 11, 12, 13, 14, 15, 16, 17, 25, 26, 27, 28, 29, 32 showed over 90% of mortality rate of the insects.

Example 38

Insecticidal Test on American Dog Ticks

[0233] 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, 5, 6, 9, 10, 11, 12, 13, 14, 15, 16, 17, 25, 26, 27, 28, 29, 32 showed over 90% of mortality rate of the insects.

INDUSTRIAL APPLICABILITY

[0234] This disclosure provides an isophthalamide compound with an excellent 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.