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KR-102962498-B1 - A horticultural agent containing a novel imidazopyridine-2-carboxamide derivative as an active ingredient

KR102962498B1KR 102962498 B1KR102962498 B1KR 102962498B1KR-102962498-B1

Abstract

This invention provides a compound useful as an active ingredient for horticultural agents, particularly horticultural pest control agents, for example, horticultural insecticides or horticultural mite control agents. The compound is an imidazopyridine-2-carboxamide derivative represented by the formula (1) below, its N-oxide, or its salt. In the formula, R1 and R2 are, for example, C1-3 alkyl groups, X is, for example, an oxygen atom or a sulfur atom, A1 , A2 , A3 , A4 , and A5 are each independently a nitrogen atom or CR3 , R3 is, for example, a hydrogen atom or a C1-3 haloalkyl group, and R4 is, for example, a C1-3 alkyl group or a C1-3 haloalkyl group.

Inventors

  • 오야마 가쯔아키
  • 오지마 코헤이
  • 아라키 코이찌
  • 모리시타 사키
  • 후쿠치 토시키

Assignees

  • 아구로카네쇼 가부시키가이샤

Dates

Publication Date
20260508
Application Date
20200612
Priority Date
20190613

Claims (13)

  1. Equation (1) below [During the meal, R1 represents a C1-6 alkyl group or a C1-6 haloalkyl group, and R₂ represents a hydrogen atom, a C1-6 alkyl group, or a C1-6 haloalkyl group, and X represents an oxygen atom, a sulfur atom, or ―SO₂― , A1 , A2 , A3 , A4 , and A5 each independently represent a nitrogen atom or CR3 , where two of A1 , A2 , A3 , A4 , and A5 are not simultaneously nitrogen atoms, and also at least one of A1 , A2 , A3 , A4 , and A5 is CR3 , and R3 may be the same or different, and is a hydrogen atom, a halogen atom, a C1-6 alkyl group, a C1-6 haloalkyl group, a C3-8 cycloalkyl group, a C1-6 alkoxy group, a C3-6 alkenyloxy group, a C3-6 alkynyloxy group, a C1-6 haloalkoxy group, a C3-6 haloalkenyloxy group, a C3-6 haloalkynoyloxy group, a C1-6 alkylthio group, a C1-6 alkylsulfinyl group, a C1-6 alkylsulfonyl group, a C1-6 haloalkylthio group, a C1-6 haloalkylsulfinyl group, a C1-6 haloalkylsulfonyl group, a nitro group, a cyano group, a phenyl group that may be substituted with 1 to 4 R5s , a phenoxy group that may be substituted with 1 to 4 R6s , and 1 to 2 R7s It represents a triazoryl group substituted with, or, in the case where two R3s are substituted with two adjacent carbon atoms, said two R3s may each be combined with the carbon atom to which they are bonded to form a saturated or unsaturated 5 or 6-membered ring, and R5 , R6 , and R7 each independently represent a halogen atom, a C1-6 alkyl group, a C1-6 haloalkyl group, a C3-8 cycloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylthio group, a C1-6 alkylsulfinyl group, a C1-6 alkylsulfonyl group, a C1-6 haloalkylthio group, a C1-6 haloalkylsulfinyl group, or a C1-6 haloalkylsulfonyl group, and R 4 may be the same or different and represents a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 3-8 cycloalkyl group, a C 1-6 alkoxy group, a nitro group, or a cyano group, and n represents an integer from 0 to 2, and m represents an integer from 0 to 4. An imidazopyridine-2-carboxamide derivative represented by, its N-oxide or its salt.
  2. In paragraph 1, R 1 is an imidazopyridine-2-carboxamide derivative representing a C 1-6 alkyl group, its N-oxide or its salt.
  3. In paragraph 1, R 2 is an imidazopyridine-2-carboxamide derivative representing a C 1-6 alkyl group, its N-oxide or its salt.
  4. In paragraph 1, An imidazopyridine-2-carboxamide derivative in which X represents an oxygen atom, the N-oxide or the salt thereof.
  5. In paragraph 1, An imidazopyridine-2-carboxamide derivative in which X represents a sulfur atom, its N-oxide or its salt.
  6. A method for preparing an imidazopyridine-2-carboxamide derivative represented by the following formula (1-1) or (1-2), A method for manufacturing a derivative of imidazopyridine-2-carboxamide represented by formula (1-0), comprising oxidizing it.
  7. A horticultural agent containing an imidazopyridine-2-carboxamide derivative described in any one of paragraphs 1 to 5, the N-oxide, or the salt thereof.
  8. A mite control agent for agricultural horticulture containing an imidazopyridin-2-carboxamide derivative described in any one of claims 1 to 5, the N-oxide thereof, or the salt thereof.
  9. A pest control agent for agricultural horticulture containing an imidazopyridin-2-carboxamide derivative described in any one of claims 1 to 5, the N-oxide, or the salt thereof.
  10. A disease prevention agent for agricultural horticulture containing an imidazopyridine-2-carboxamide derivative described in any one of claims 1 to 5, the N-oxide, or the salt thereof.
  11. A method for controlling harmful organisms on plants, comprising a process of treating harmful organisms and/or their reproductive environment and/or seeds and/or plant breeding material that are targets of attack by harmful organisms with a horticultural agent described in claim 7.
  12. A method for controlling harmful organisms on plants, comprising a process of treating a place where a useful crop is to be grown, a place where it is being grown, or a crop that is being grown with a horticultural agent described in claim 7.
  13. A method for preparing a pesticide composition, comprising the process of mixing an extender and/or a surfactant with a horticultural agent described in claim 7.

Description

A horticultural agent containing a novel imidazopyridine-2-carboxamide derivative as an active ingredient The present invention relates to a novel imidazopyridine-2-carboxamide compound and a horticultural agent having the compound as an active ingredient, particularly a method of use as an insecticide for horticultural purposes. In the field of agrohorticulture, plant pest control agents aimed at controlling various diseases and pests have been developed and commercialized. However, conventional insecticides used in agrohorticulture are not necessarily satisfactory in terms of insecticidal efficacy or residual effect. Furthermore, they could not be said to satisfy requirements such as increased application frequency or reduced dosage. In addition, the emergence of various types of mites that have acquired resistance to conventional general-purpose mite killers is also becoming a problem. There is an urgent need for the development of new insecticides that provide sufficient control effects with low dosages against various pests and diseases that have acquired resistance to conventional general-purpose agricultural and horticultural insecticides, and furthermore, have minimal adverse effects on the environment. Various new tick-killing agents are being proposed to meet these demands, but they do not necessarily meet the aforementioned requirements. The following compounds A and B are disclosed as imidazopyridine-2-carboxamide derivatives similar to the present invention. Patent Document 1 discloses a compound comprising the following compound A. However, Patent Document 1 does not disclose at all the N-alkyloxy group and N-alkylthio group having the compound of the present invention. In addition, Patent Document 2 discloses a compound comprising the following compound B, but its acid portion is limited to the pyridine ring, and the imidazopyridine ring is not disclosed at all in Patent Document 2. The inventors have discovered, through careful examination, that the present invention possesses significantly higher insecticidal activity compared to Compound A and Compound B. Such an improvement in activity was entirely unexpected and was revealed for the first time through the inventors' experiments. Meanwhile, a patent document is disclosed that includes the following compounds as carboxyamide derivatives having an N-alkyl group, wherein the acid portion is an aromatic ring or an aromatic hetero ring. However, these compounds are not compounds having an N-alkoxy group or an N-alkylthio group. Also, the acid portion does not have an imidazopyridine ring. In the definition of the compound of the present invention represented by the above formula (1), "halogen atom" refers to a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom; " C1-6 alkyl group" refers to a straight-chain or branched-chain type alkyl group having 1 to 6 carbon atoms, preferably 1 to 3, such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, a t-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, an n-hexyl group, or an isohexyl group; and " C1-6 haloalkyl" refers to one or more, which may be the same or different, preferably, It represents a straight-chain or branched-chain type alkyl group having 1 to 6 carbon atoms specified above, substituted by 1 to 3 halogen atoms, and “C 3-8 cycloalkyl” represents a cyclic cycloalkyl group having 3 to 8 carbon atoms, preferably 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl. Specific examples of the “C 1-6 haloalkyl group” include, for example, a fluoromethyl group, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2-iodoethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a pentafluoroethyl group, a 1-fluoroisopropyl group, a 3-fluoropropyl group, a 3-chloropropyl group, a 3-bromopropyl group, a heptafluoropropyl group, a 4-fluorobutyl group, a 4-chlorobutyl group, a nonafluorobutyl group, a 5,5,5-trifluoropentyl group, a 5-chloropentyl group, a undecafluoropentyl group, and a 6, Examples include straight-chain or branched-chain alkyl groups having 1 to 6 carbon atoms as defined above, which are substituted with 1 to 13, preferably 1 to 9, halogen atoms such as 6,6-trifluorohexyl groups, 6-chlorohexyl groups, and tridecafluorohexyl groups. As for the “C 1-6 alkoxy group,” examples include straight-chain or branched-chain alkoxy groups having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms, such as methoxy groups, ethoxy groups, n-propoxy groups, isopropoxy groups, n-butoxy groups, sec-butoxy groups, tert-butoxy groups, n-pentoxy groups, and n-hexyloxy groups. As the "C 1-6 haloalkoxy group," for example,