JPWO2016175017A1 - Novel 4-pyridinecarboxamide derivative and agricultural and horticultural agent containing this as an active ingredient - Google Patents

Abstract

The present invention provides an excellent compound as an active ingredient of an agricultural and horticultural medicine. Specifically, formula (1) [wherein R1 represents a C1-6 alkyl group or a C1-6 haloalkyl group, R2 represents a hydrogen atom, a C1-6 alkyl group or a C1-6 haloalkyl group, G1, G2, G3, G4 and G5 each independently represent a nitrogen atom or C-R3 (however, G1, G2, G3, G4 and G5 are not nitrogen atoms at the same time, but G1, G2, G3, G4 And at least one of G5 is C—R3), R3 may be the same or different and each represents a hydrogen atom, a halogen atom, a C1-12 alkyl group, a C1-12 haloalkyl group, a C3-8 cycloalkyl group, C1 -6 alkoxy group, C3-6 alkenyloxy group, C3-6 alkynyloxy group, C1-6 haloalkoxy group, C3-6 haloalkenyloxy group, C3-6 haloalkynyloxy group, C1-6 alkylthio group, C1- 6 alkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylthio group, C1-6 haloalkyls A finyl group, a C1-6 haloalkylsulfonyl group, a nitro group, a cyano group, SF5, a phenyl group which may be substituted with 1 to 4 R4s, or a phenoxy group which may be substituted with 1 to 4 R5s. Or when two R3 comprise a ring containing G1 to G5 and are bonded to each of two adjacent carbon atoms, the two R3 are bonded to each other; May form a saturated or unsaturated 5- or 6-membered ring together with the ring-constituting carbon atoms, and R4 and R5 each independently represent a halogen atom, a C1-6 alkyl group, or a C1-6 haloalkyl. Group, C3-8 cycloalkyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C1-6 alkylthio group, C1-6 alkylsulfinyl group, C1-4 alkylsulfonyl group, C1-6 haloalkylthio group, C1 -6 haloalkylsulfinyl group or C1-6 A haloalkylsulfonyl group, wherein X may be the same or different and each represents 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 nitro group or Represents a cyano group, n represents an integer of 0 to 2, and m represents an integer of 0 to 3. The 4-pyridinecarboxamide derivative represented by these, its N-oxide, or its salt are provided.

Description

  The present invention relates to a novel 4-pyridinecarboxamide derivative, and an agricultural and horticultural drug containing the derivative as an active ingredient, particularly an agricultural and horticultural insecticide.

  In the field of agriculture and horticulture, plant pest control agents aimed at controlling various pests have been developed and put to practical use.

  Patent Document 1 describes that compounds of the following formula are useful as agricultural and horticultural nematicides.

  Patent Document 2 discloses a 4-pyridinecarboxamide compound having the following formula.

  Patent Document 3 discloses a 4-pyridinecarboxamide compound represented by the following formula as an intermediate of a medicine.

  Patent Document 4 discloses a 4-pyridinecarboxamide compound represented by the following formula as a pharmaceutical intermediate.

  Patent Document 5 discloses a 3-pyridinecarboxamide compound of the following formula as an endoparasite control agent, but does not disclose a 4-pyridinecarboxamide compound.

  Patent Document 6 discloses a 2-pyridinecarboxamide compound represented by the following formula as an insecticide, but does not disclose a 4-pyridinecarboxamide compound.

  Non-Patent Document 1 discloses a 4-pyridinecarboxamide compound of the following formula as a reaction intermediate.

International Publication No.2013 / 064521 International Publication No. 2014/040969 International Publication No. 2005/004866 International Publication No. 2000/55153 JP-A-5-32631 International Publication No. 2014/021468

Tetrahydron Letters, Vol.34, No.18, pp.2875-2878 (1993)

  However, the occurrence of crops such as agriculture and horticulture is still great due to the generation of resistant pests against existing drugs, and the development of new drugs is eagerly desired.

[式中、
R¹は、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
R²は、水素原子、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
G¹、G²、G³、G⁴及びG⁵は、それぞれ独立して、窒素原子又はC-R³を示し（但し、G¹、G²、G³、G⁴及びG⁵は同時に窒素原子ではなく、G¹、G²、G³、G⁴及びG⁵の少なくとも１つはC-R³である）、
R³は、同一又は異なっても良く、水素原子、ハロゲン原子、Ｃ_1-12アルキル基、Ｃ_1-12ハロアルキル基、Ｃ_3-8シクロアルキル基、Ｃ_1-6アルコキシ基、Ｃ_3-6アルケニルオキシ基、Ｃ_3-6アルキニルオキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_3-6ハロアルケニルオキシ基、Ｃ_3-6ハロアルキニルオキシ基、Ｃ_1-6アルキルチオ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基、Ｃ_1-6ハロアルキルチオ基、Ｃ_1-6ハロアルキルスルフィニル基、Ｃ_1-6ハロアルキルスルホニル基、ニトロ基、シアノ基、SF5、１から４個のR⁴で置換されても良いフェニル基、又は、１から４個のR⁵で置換されても良いフェノキシ基を示すか、あるいは、
２つのＲ³が、Ｇ¹〜Ｇ⁵を含む環を構成し、かつ、隣接している２つの炭素原子のそれぞれに結合している場合、該２つのＲ³は互いに結合し、更に前記の環構成炭素原子と一緒になって飽和又は不飽和の５又は６員環を形成してもよく、
R⁴及びR⁵は、それぞれ独立して、ハロゲン原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-8シクロアルキル基、Ｃ_1-6アルコキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-4アルキルスルホニル基、Ｃ_1-6ハロアルキルチオ基、Ｃ_1-6ハロアルキルスルフィニル基又はＣ_1-6ハロアルキルスルホニル基を示し、
Xは、同一又は異なっても良く、水素原子、ハロゲン原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-8シクロアルキル基、Ｃ_1-6アルコキシ基、ニトロ基又はシアノ基を示し、
nは、0から2の整数を示し、
mは、0から3の整数を示す。]
で表される４−ピリジンカルボキサマイド誘導体、そのＮ−オキシド又はその塩。

２.Ｒ¹がＣ_1-6アルキル基を示す、前記１に記載の４−ピリジンカルボキサマイド誘導体、そのＮ−オキシド又はその塩。

３.Ｒ²が水素原子又はＣ_1-6アルキル基を示す、前記１又は２に記載の４−ピリジンカルボキサマイド誘導体、そのＮ−オキシド又はその塩。

４.mが0を示す、前記１〜３のいずれか１項に記載の４−ピリジンカルボキサマイド誘導体、そのＮ−オキシド又はその塩。

５.前記１〜４のいずれか１項に記載の４−ピリジンカルボキサマイド誘導体、そのＮ−オキシド又はその塩を含有する農園芸用薬剤。

６.農園芸用殺虫剤である、前記５に記載の農園芸用薬剤。As a result of intensive studies to solve the above problems, the present inventors have found that a 4-pyridinecarboxamide derivative represented by the following formula (I), which is a novel compound not described in the literature, is an agricultural and horticultural drug, It was found to be particularly useful as an agricultural and horticultural insecticide. The present invention has been made based on this finding. That is, the present invention relates to the following.

1. Formula (1)

[Where
R ¹ represents a C _1-6 alkyl group or a C _1-6 haloalkyl group,
R ² represents a hydrogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
G ¹ , G ² , G ³ , G ⁴ and G ⁵ each independently represent a nitrogen atom or CR ³ (provided that G ¹ , G ² , G ³ , G ⁴ and G ⁵ are simultaneously nitrogen atoms And at least one of G ¹ , G ² , G ³ , G ⁴ and G ⁵ is CR ³ ),
R ³ may be the same or different and is a hydrogen atom, a halogen atom, a C _1-12 alkyl group, a C _1-12 haloalkyl group, a C _3-8 cycloalkyl group, a C _1-6 alkoxy group, a C _3-6 Alkenyloxy group, C _3-6 alkynyloxy group, C _1-6 haloalkoxy group, C _3-6 haloalkenyloxy group, C _3-6 haloalkynyloxy group, C _1-6 alkylthio group, C _1-6 alkyl sulfinyl group, C _1-6 alkylsulfonyl group, C _1-6 haloalkylthio group, C _1-6 haloalkylsulfinyl group, C _1-6 haloalkylsulfonyl group, a nitro group, a cyano group, four R ⁴ from SF5,1 A phenyl group which may be substituted with, or a phenoxy group which may be substituted with 1 to 4 R ⁵ , or
When two R ³ constitute a ring containing G ^{1 to} G ⁵ and are bonded to each of two adjacent carbon atoms, the two R ³ are bonded to each other, and Together with the ring carbon atoms may form a saturated or unsaturated 5- or 6-membered ring,
R ⁴ and R ⁵ are each independently a halogen atom, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy show group, C _1-6 alkylthio group, C _1-6 alkylsulfinyl group, C _1-4 alkylsulfonyl group, C _1-6 haloalkylthio group, a C _1-6 haloalkylsulfinyl group or a C _1-6 haloalkylsulfonyl group ,
X may be the same or different, and may be 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. Indicate
n represents an integer from 0 to 2,
m represents an integer of 0 to 3. ]
A 4-pyridinecarboxamide derivative represented by the formula: N-oxide or a salt thereof.

2. The 4-pyridinecarboxamide derivative according to 1 above, wherein R ¹ represents a C _1-6 alkyl group, an N-oxide thereof or a salt thereof.

3. The 4-pyridinecarboxamide derivative, the N-oxide or a salt thereof according to the above 1 or 2, wherein R ² represents a hydrogen atom or a C _1-6 alkyl group.

4. The 4-pyridinecarboxamide derivative, N-oxide or salt thereof according to any one of 1 to 3, wherein m is 0.

5. An agricultural and horticultural agent containing the 4-pyridinecarboxamide derivative, its N-oxide or a salt thereof according to any one of 1 to 4 above.

6. The agricultural and horticultural agent according to 5 above, which is an agricultural and horticultural insecticide.

  As shown in Examples described later, the compound of the present invention exhibits excellent effects as agricultural and horticultural agents, particularly agricultural and horticultural insecticides. Furthermore, the compounds of the present invention are also effective against pests parasitic on pets such as dogs and cats or livestock such as cows and sheep.

[式中、
R¹は、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
R²は、水素原子、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
G¹、G²、G³、G⁴及びG⁵は、それぞれ独立して、窒素原子又はC-R³を示し（但し、G¹、G²、G³、G⁴及びG⁵は同時に窒素原子ではなく、G¹、G²、G³、G⁴及びG⁵の少なくとも１つはC-R³である）、
R³は、同一又は異なっても良く、水素原子、ハロゲン原子、Ｃ_1-12アルキル基、Ｃ_1-12ハロアルキル基、Ｃ_3-8シクロアルキル基、Ｃ_1-6アルコキシ基、Ｃ_3-6アルケニルオキシ基、Ｃ_3-6アルキニルオキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_3-6ハロアルケニルオキシ基、Ｃ_3-6ハロアルキニルオキシ基、Ｃ_1-6アルキルチオ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基、Ｃ_1-6ハロアルキルチオ基、Ｃ_1-6ハロアルキルスルフィニル基、Ｃ_1-6ハロアルキルスルホニル基、ニトロ基、シアノ基、SF5（ペンタフルオロスルファニル基）、１から４個のR⁴で置換されても良いフェニル基、又は、１から４個のR⁵で置換されても良いフェノキシ基を示すか、あるいは、
２つのＲ³が、Ｇ¹〜Ｇ⁵を含む環を構成し、かつ、隣接している２つの炭素原子のそれぞれに結合している場合、該２つのＲ³は互いに結合し、更に前記の環構成炭素原子と一緒になって飽和又は不飽和の５又は６員環を形成してもよく、
R⁴及びR⁵は、それぞれ独立して、ハロゲン原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-8シクロアルキル基、Ｃ_1-6アルコキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_1-6アルキルチオ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-4アルキルスルホニル基、Ｃ_1-6ハロアルキルチオ基、Ｃ_1-6ハロアルキルスルフィニル基又はＣ_1-6ハロアルキルスルホニル基を示し、
Xは、同一又は異なっても良く、水素原子、ハロゲン原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-8シクロアルキル基、Ｃ_1-6アルコキシ基、ニトロ基又はシアノ基を示し、
nは、0から2の整数を示し、
mは、0から3の整数を示す。]
で表される４−ピリジンカルボキサマイド誘導体である。Hereinafter, the present invention will be described in more detail.
The compounds of the present invention have the formula (1):

[Where
R ¹ represents a C _1-6 alkyl group or a C _1-6 haloalkyl group,
R ² represents a hydrogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
G ¹ , G ² , G ³ , G ⁴ and G ⁵ each independently represent a nitrogen atom or CR ³ (provided that G ¹ , G ² , G ³ , G ⁴ and G ⁵ are simultaneously nitrogen atoms And at least one of G ¹ , G ² , G ³ , G ⁴ and G ⁵ is CR ³ ),
R ³ may be the same or different and is a hydrogen atom, a halogen atom, a C _1-12 alkyl group, a C _1-12 haloalkyl group, a C _3-8 cycloalkyl group, a C _1-6 alkoxy group, a C _3-6 Alkenyloxy group, C _3-6 alkynyloxy group, C _1-6 haloalkoxy group, C _3-6 haloalkenyloxy group, C _3-6 haloalkynyloxy group, C _1-6 alkylthio group, C _1-6 alkyl sulfinyl group, C _1-6 alkylsulfonyl group, C _1-6 haloalkylthio group, C _1-6 haloalkylsulfinyl group, C _1-6 haloalkylsulfonyl group, a nitro group, a cyano group, SF5 (pentafluorosulfanyl group), 1 Represents a phenyl group which may be substituted with ⁴ to R ⁴ , or a phenoxy group which may be substituted with 1 to 4 R ⁵ , or
When two R ³ constitute a ring containing G ^{1 to} G ⁵ and are bonded to each of two adjacent carbon atoms, the two R ³ are bonded to each other, and Together with the ring carbon atoms may form a saturated or unsaturated 5- or 6-membered ring,
R ⁴ and R ⁵ are each independently a halogen atom, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy show group, C _1-6 alkylthio group, C _1-6 alkylsulfinyl group, C _1-4 alkylsulfonyl group, C _1-6 haloalkylthio group, a C _1-6 haloalkylsulfinyl group or a C _1-6 haloalkylsulfonyl group ,
X may be the same or different, and may be 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. Indicate
n represents an integer from 0 to 2,
m represents an integer of 0 to 3. ]
The 4-pyridinecarboxamide derivative represented by these.

The definition of each substituent in the formula (I) is as follows.
The “C _1-6 alkyl group” of R ¹ is, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group. , N-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, isohexyl group and the like, which are linear or branched alkyl groups having 1 to 6 carbon atoms.

The “C _1-6 haloalkyl group” for R ¹ refers to a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
Examples of the “C _1-6 haloalkyl group” include a fluoromethyl group, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, and a 1-fluoroethyl group. 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-iodoethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 1- Fluoroisopropyl group, 3-fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, heptafluoropropyl group, 4-fluorobutyl group, 4-chlorobutyl, nonafluorobutyl group, 5,5,5-trifluoro Pentyl group, 5-chloropentyl group, undecafluoropentyl group, 6,6, A linear or branched chain having 1 to 6 carbon atoms substituted with 1 to 13, preferably 1 to 9, halogen atoms such as 6-trifluorohexyl group, 6-chlorohexyl group, tridecafluorohexyl group, etc. An alkyl group.
As the “C _1-6 haloalkyl group”, a “C _1-3 haloalkyl group” is preferable.

R ¹ is preferably a “C _1-6 alkyl group”, more preferably a “C _1-3 alkyl group”, particularly preferably a methyl group or an ethyl group.

The “C _1-6 alkyl group” for R ² is the same as defined for the “C _1-6 alkyl group” for R ¹ . As the “C _1-6 alkyl group” for R ² , a “C _1-3 alkyl group” is preferable, and a methyl group or an ethyl group is particularly preferable.

The “C _1-6 haloalkyl group” for R ² is the same as that defined for the “C _1-6 haloalkyl group” for R ¹ . The “C _1-6 haloalkyl group” for R ² is preferably a “C _1-3 haloalkyl group”.

The “halogen atom” for R ³ refers to a chlorine atom, bromine atom, iodine atom or fluorine atom.

The “C _1-12 alkyl group” of R ³ is, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group. Or a linear or branched alkyl group having 1 to 12 carbon atoms.

The “C _1-12 haloalkyl group” for R ³ refers to a linear or branched alkyl group having 1 to 12 carbon atoms substituted with one or more halogen atoms which may be the same or different.
Examples of the “C _1-6 haloalkyl group” include a trifluoromethyl group and a pentafluoroethyl group.

The “C _3-8 cycloalkyl group” for R ³ refers to a cyclic cycloalkyl group having 3 to 8 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like.

The “C _1-6 alkoxy group” of R ³ is, for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, cyclopropyloxy group, n-butoxy group, sec-butoxy group, tert-butoxy group. , An n-pentoxy group, an n-hexyloxy group and the like, and a straight or branched alkoxy group having 1 to 6 carbon atoms.

The “C _3-6 alkenyloxy group” for R ³ is, for example, allyloxy group, isopropenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-methyl-2-propenyloxy group, 2-pentenyloxy group. 3-pentenyloxy group, 4-pentenyloxy group, 1,1-dimethyl-2-propenyloxy group, 1-ethyl-2-propenyloxy group, 1-methyl-2-butenyloxy group, 1-methyl-3- Butenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 1,1-dimethyl-2-butenyloxy group, 1,1-dimethyl-3-butenyloxy group, etc. Or a straight or branched alkenyloxy group having 3 to 6 carbon atoms and having at least one double bond at any position.

The “C _3-6 alkynyloxy group” for R ³ is, for example, a 2-propynyloxy group, a 1-methyl-2-propynyloxy group, a 1,1-dimethyl-2-propynyloxy group, a 1-butynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 1-pentynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group, 1-methyl-2-butynyloxy group, 1-methyl -3-butynyloxy group, 1,1-dimethyl-2-butynyloxy group, 1,1-dimethyl-3-butynyloxy group, 1-methyl-3-pentynyloxy group, and 1-methyl-4-pentynyloxy group A linear or branched alkynyloxy group having 3 to 6 carbon atoms and having at least one triple bond at an arbitrary position.

The “C _1-6 haloalkoxy group” for R ³ is, for example, fluoromethoxy group, dichloromethoxy group, trichloromethoxy group, difluoromethoxy group, trifluoromethoxy group, chlorodifluoromethoxy group, bromodifluoromethoxy group, dichlorofluoro Methoxy group, 1-fluoroethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2-iodoethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2- Such as trichloroethoxy group, pentafluoroethoxy group, 1-fluoroisopropoxy group, 3-fluoropropoxy group, 3-chloropropoxy group, 3-bromopropoxy group, 4-fluorobutoxy group, 4-chlorobutoxy group, 1 to 9 carbon atoms substituted with 1 to 9 halogen atoms It includes branched chain alkoxy groups.

Examples of the “C _3-6 haloalkenyloxy group” for R ³ include a 3-chloro-2-propenyloxy group, a 3,3-difluoro-2-allyloxy group, a 3,3-dichloro-2-allyloxy group, 4,4,4-trifluoro-2-butenyloxy group, 4,4,4-trifluoro-3-butenyloxy group, 5-chloro-3-pentenyloxy group, 6-fluoro-2-hexenyloxy group, etc. A C3-C6 linear or branched alkenyloxy group having at least one double bond at an arbitrary position, which is substituted with 1 to 13, preferably 1 to 7 halogen atoms An alkenyloxy group.

The “C _3-6 haloalkynyloxy group” for R ³ is 4,4,4-trifluoro-2-butynyloxy group, 5,5,5-trifluoro-3-pentynyloxy group, 1-methyl- 3 carbon atoms having at least one triple bond at an arbitrary position such as 3,3,3-trifluoro-2-butynyloxy group, 1-methyl-5,5,5-trifluoro-2-pentynyloxy group, etc. -6 linear or branched alkynyloxy groups, which are alkynyloxy groups substituted with 1 to 9, preferably 1 to 6, halogen atoms.

The “C _1-6 alkylthio group” of R ³ is, for example, methylthio group, ethylthio group, n-propylthio group, isopropylthio group, cyclopropylthio group, n-butylthio group, sec-butylthio group, tert-butylthio group. , An n-pentylthio group, an n-hexylthio group, etc., and a C1-C6 linear or branched alkylthio group.

The “C _1-6 alkylsulfinyl group” for R ³ is, for example, methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, isopropylsulfinyl group, cyclopropylsulfinyl group, n-butylsulfinyl group, sec-butylsulfinyl group. A straight chain or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as a group, a tert-butylsulfinyl group, an n-pentylsulfinyl group, and an n-hexylsulfinyl group.

The “C _1-6 alkylsulfonyl group” of R ³ is, for example, methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isoprosulfonyl group, cyclopropylsulfonyl group, n-butylsulfonyl group, sec-butylsulfonyl. A linear or branched alkylsulfonyl group having 1 to 6 carbon atoms, such as a group, a tert-butylsulfonyl group, an n-pentylsulfonyl group, and an n-hexylsulfonyl group.

The “C _1-6 haloalkylthio group” for R ³ is, for example, a difluoromethylthio group, a trifluoromethylthio group, a monochloromethylthio group, a dichloromethylthio group, a trichloromethylthio group, a monobromomethylthio group, a dibromomethylthio group, a tribromomethylthio group. Group, 1-fluoroethylthio group, 2-fluoroethylthio group, 2,2-difluoroethylthio group, 2,2,2-trifluoroethylthio group, 2-chloro-2,2-difluoroethylthio group, 1-chloroethylthio group, 2-chloroethylthio group, 2,2, -dichloroethylthio group, 2,2,2-trichloroethylthio group, 2-bromoethylthio group, 2,2-dibromoethylthio group 2,2,2-tribromoethylthio group, pentafluoroethylthio group, 3-fluoropropylthio group, 3-chloropropylthio group, 3-bromopropylthio group, 1,3-difluoro-2-propyl Thio group, 3,3,3-trifluoropropylthio group, 1,3-dichloro-2-propylthio group, 1,1,1-trifluoro-2-propylthio group, 1-chloro-3-fluoro-2- Propylthio group, 1,1,1,3,3,3-hexafluoro-2-propylthio group, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propylthio group, 2,2 , 3,3,3-pentafluoropropylthio group, heptafluoroisopropylthio group, heptafluoro-n-propylthio group, 4-fluorobutylthio group, 4,4,4-trifluorobutylthio group, nonafluoro-n- A linear or branched alkylthio group having 1 to 6 carbon atoms and substituted with 1 to 13, preferably 1 to 9 halogen atoms, such as a butylthio group and a nonafluoro-2-butylthio group.

The “C _1-6 haloalkylsulfinyl group” of R ³ is difluoromethylsulfinyl group, trifluoromethylsulfinyl group, dichloromethylsulfinyl group, trichloromethylsulfinyl group, monobromomethylsulfinyl group, dibromomethylsulfinyl group, tribromomethyl Sulfinyl group, 1-fluoroethylsulfinyl group, 2-fluoroethylsulfinyl group, 2,2-difluoroethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 2-chloro-2,2-difluoroethylsulfinyl group 1-chloroethylsulfinyl group, 2-chloroethylsulfinyl group, 2,2-dichloroethylsulfinyl group, 2,2,2-trichloroethylsulfinyl group, 2-bromoethylsulfinyl group, 2,2-dibromoethylsulfinyl group 2,2,2-tribromoethylsulfini Group, pentafluoroethylsulfinyl group, 3-fluoropropylsulfinyl group, 3-chloropropylsulfinyl group, 3-bromopropylsulfinyl group, 1,3-difluoro-2-propylsulfinyl group, 3,3,3-trifluoropropyl Sulfinyl group, 1,3-dichloro-2-propylsulfinyl group, 1,1,1-trifluoro-2-propylsulfinyl group, 1-chloro-3-fluoro-2-propylsulfinyl group, 1,1,1, 3,3,3-hexafluoro-2-propylsulfinyl group, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propylsulfinyl group, 2,2,3,3,3- Pentafluoropropylsulfinyl group, heptafluoroisopropylsulfinyl group, heptafluoro-n-propylsulfinyl group, 4-fluorobutylsulfinyl group, 4,4,4-trifluorobutylsulfinyl group, nonafluoro-n-butylsulfinyl group Group, such as nonafluoro-2-butyl sulfinyl group, 1 to 13, preferably refers to 1-9 straight-chain or branched-chain alkylsulfinyl group of 1 to 6 carbons substituted with a halogen atom.

The “C _1-6 haloalkylsulfonyl group” of R ³ is a difluoromethylsulfonyl group, a trifluoromethylsulfonyl group, a dichloromethylsulfonyl group, a trichloromethylsulfsulfonyl group, a monobromomethylsulfonyl group, a dibromomethylsulfonyl group, Tribromomethylsulfonyl group, 1-fluoroethylsulfonyl group, 2-fluoroethylsulfonyl group, 2,2-difluoroethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 2-chloro-2,2-difluoro Ethylsulfonyl group, 1-chloroethylsulfonyl group, 2-chloroethylsulfonyl group, 2,2, -dichloroethylsulfonyl group, 2,2,2-trichloroethylsulfonyl group, 2-bromoethylsulfonyl group, 2,2- Dibromoethylsulfonyl group, 2,2,2-tribromoethylsulfonyl group, pentafluoroethylsulfonyl group Group, 3-fluoropropylsulfonyl group, 3-chloropropylsulfonyl group, 3-bromopropylsulfonyl group, 1,3-difluoro-2-propylsulfonyl group, 3,3,3-trifluoropropylsulfonyl group, 1,3 -Dichloro-2-propylsulfonyl group, 1,1,1-trifluoro-2-propylsulfonyl group, 1-chloro-3-fluoro-2-propylsulfonyl group, 1,1,1,3,3,3- Hexafluoro-2-propylsulfonyl group, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propylsulfonyl group, 2,2,3,3,3-pentafluoropropylsulfonyl group, Heptafluoroisopropylsulfonyl group, heptafluoro-n-propylsulfonyl group, 4-fluorobutylsulfonyl group, 4,4,4-trifluorobutylsulfonyl group, nonafluoro-n-butylsulfonyl group, nonafluoro-2-butylsulfonyl group, etc. 1-13 pieces are preferred Refers to 1-9 straight-chain or branched-chain alkylsulfonyl group having 1 to 6 carbon atoms substituted with a halogen atom.

The “halogen atom” for R ⁴ and R ⁵ is the same as that defined for the “halogen atom” for R ³ .

The “C _1-6 alkyl group” for R ⁴ and R ⁵ is the same as defined for the “C _1-6 alkyl group” for R ¹ .

The “C _1-6 haloalkyl group” for R ⁴ and R ⁵ is the same as defined for the “C _1-6 haloalkyl group” for R ¹ .

The “C _3-8 cycloalkyl group” for R ⁴ and R ⁵ is the same as that defined for the “C _3-8 cycloalkyl group” for R ³ .

The “C _1-6 alkoxy group” for R ⁴ and R ⁵ is the same as that defined for the “C _1-6 alkoxy group” for R ³ .

The “C _1-6 haloalkoxy group” for R ⁴ and R ⁵ is the same as that defined for the “C _1-6 haloalkoxy group” for R ³ .

The “C _1-6 alkylthio group” for R ⁴ and R ⁵ is the same as that defined for the “C _1-6 alkylthio group” for R ³ .

The “C _1-6 alkylsulfinyl group” for R ⁴ and R ⁵ is the same as that defined for the “C _1-6 alkylsulfinyl group” for R ³ .

The “C _1-4 alkylsulfonyl group” for R ⁴ and R ⁵ refers to a linear or branched alkylsulfonyl group having 1 to 4 carbon atoms such as a methanesulfonyl group or an ethanesulfonyl group.

The “C _1-6 haloalkylthio group” for R ⁴ and R ⁵ is the same as that defined for the “C _1-6 haloalkylthio group” for R ³ .

The “C _1-6 haloalkylsulfinyl group” for R ⁴ and R ⁵ is the same as that defined for the “C _1-6 haloalkylsulfinyl group” for R ³ .

The “C _1-6 haloalkylsulfonyl group” for R ⁴ and R ⁵ is the same as that defined for the “C _1-6 haloalkylsulfonyl group” for R ³ .

Here, the two R ^3, form a ring including a G ¹ ~G ^5, and, when attached to each of the two carbon atoms that are adjacent, the two R ³ may bond to each other, Furthermore, a saturated or unsaturated 5- or 6-membered ring may be formed together with the above-mentioned ring carbon atoms. Examples of the ring to be formed include a naphthalene ring and a quinoline ring.

The “halogen atom” of X is the same as defined for the “halogen atom” of R ³ .

"C _1-6 alkyl group" of X is the same as defined in the "C _1-6 alkyl group" of R ^1.

The “C _1-6 haloalkyl group” for X is the same as that defined for the “C _1-6 haloalkyl group” for R ¹ .

"C _3-8 cycloalkyl group" of X is the same as those defined with "C _3-8 cycloalkyl group" of R ^3.

"C _1-6 alkoxy group" of X is the same as defined in the "C _1-6 alkoxy group" of R ^3.

  X is preferably a hydrogen atom.

  n shows the integer of 0-2.

  m represents an integer of 0 to 3, and is preferably 0.

  The compound of the present invention may be an N-oxide of a 4-pyridinecarboxamide derivative represented by the above formula (I) or a salt thereof.

  The N-oxide of the 4-pyridinecarboxamide derivative represented by the formula (I) may be pyridine N-oxide.

  Examples of the salt of the 4-pyridinecarboxamide derivative represented by the formula (I) include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate, acetate, fumarate, maleate, and sulfate. Examples thereof include organic acid salts such as acid salts, methanesulfonate, benzenesulfonate, and p-toluenesulfonate.

The 4-pyridinecarboxamide derivative represented by the formula (I) exists as two or more optical isomers and diastereomers derived from one or more asymmetric centers contained in the structure. However, the present invention includes each optical isomer. Furthermore, the present invention also includes a mixture containing the above-mentioned optical isomers in an arbitrary ratio.
Further, the 4-pyridinecarboxamide derivative represented by the formula (I) may exist as two geometric isomers derived from a carbon-carbon double bond contained in the structure, The present invention includes each geometric isomer. Furthermore, the present invention also includes a mixture containing the above-mentioned geometric isomer in an arbitrary ratio.

  Below, although the typical manufacturing method of the novel 4-pyridinecarboxamide derivative represented by the said Formula (1) of this invention is shown, this invention is not limited to these.

Reaction formula 1

[Wherein R ¹ , R ² , G ¹ , G ² , G ³ , G ⁴ , G ⁵ , X and m are as defined above]. ]

  In the method shown in Reaction Scheme 1, the compounds represented by Formulas (1-1) and (1-2) corresponding to the 4-pyridinecarboxamide derivative represented by Formula (1) are represented by Formula (1). -0) is produced by an oxidation reaction of a 4-pyridinecarboxamide derivative.

As the solvent used in the oxidation reaction of the compound represented by the formula (1-0), a solvent inert to the reaction can be widely used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, halogenation such as methylene chloride, 1,2-dichloroethane, chloroform, etc. Hydrocarbon solvents, alcohol solvents such as methanol and ethanol, ester solvents such as methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, amide solvents such as N, N-dimethylformamide, acetonitrile and propio Examples thereof include acetic acid such as nitrile solvents such as nitrile, aprotic polar solvents such as N-methylpyrrolidone and N, N′-dimethylimidazolinone. These solvents can be used alone or in combination of two or more as required.
Examples of the oxidizing agent used in the oxidation reaction of the compound represented by the formula (1-0) include m-chloroperbenzoic acid, sodium perelementate, and hydrogen peroxide.
Such an oxidizing agent can be used in an amount that is usually 1 to 3 equivalents, preferably 1 to 2.5 equivalents, relative to the 4-pyridinecarboxamide derivative represented by the formula (1-0). .
The reaction can usually be performed within a range from -78 ° C to the boiling point of the solvent used, and the reaction is preferably performed at 0 ° C to room temperature.
The reaction time varies depending on the reaction temperature and cannot be generally specified, but the reaction is usually completed in about 0.5 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by commonly used isolation means such as organic solvent extraction, chromatography, recrystallization, distillation, etc. Further, it can be purified by ordinary purification means.

Reaction formula 2-1

[Wherein R ¹ , G ¹ , G ² , G ³ , G ⁴ , G ⁵ , X and m are as defined above]. R ⁶ represents a C _1-6 alkyl group or a C _1-6 haloalkyl group, and Y represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group or a trifluoromethanesulfonyloxy group. ]
Incidentally, "C _1-6 alkyl group" and "C _1-6 haloalkyl group" of R ⁶ are the same as those defined "C _1-6 alkyl group" and "C _1-6 haloalkyl group" of R ² It is.

Reaction formula 2-2

[Wherein Z represents a halogen atom, and other symbols are as defined above. ]
The “halogen atom” of Z is the same as that defined for the “halogen atom” of R ³ .
In addition, the compound represented by Formula (2) is a precursor of the compound of this invention represented by Formula (1).

In the method shown in the reaction formula 2-1 and the reaction formula 2-2, according to the method described in Bioorganic Medicinal Chemistry Letters, 18 (20) 5537-5540 (2008), the above formula (1-3) or (2) By reacting the represented 4-pyridinecarboxamide derivative with an alkylating agent represented by R ⁶ -Y or (R ⁶ ) ₂ SO 4 in a solvent in the presence of a base, the above formula (3) Is produced.

As the solvent used in the reactions shown in Reaction Formulas 2-1 and 2-2, known solvents can be widely used as long as they are inert to the reaction. For example, ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, amide solvents such as N, N-dimethylformamide, solvents such as dimethyl sulfoxide, N-methylpyrrolidone, N, N′-dimethylimidazolinone Can be mentioned. These solvents can be used alone or in combination of two or more as required.
As the base used in the reaction, known inorganic bases and organic bases can be used. For example, alkali metal hydrides such as sodium hydride and potassium hydride, alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, potassium t- Alkali metal alkoxides such as butoxide, triethylamine, tributylamine, diisopropylethylamine, N-methylmorpholine, pyridine, 4- (N, N-dimethylamino) pyridine, N, N-dimethylaniline, N, N-diethylaniline, 1 , 5-diazabicyclo [4.3.0] non-5-ene, 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,8-diazabicyclo [5.4.0] -7-undecene And organic bases such as (DBU). Preferred are alkali metal hydrides, alkali metal carbonates or alkali metal hydroxides, and more preferred are sodium hydride and potassium carbonate.

The amount of the base used may be such that it is usually 1 to 3 equivalents, preferably 1 to 2.5 equivalents, per 1 mol of the compound represented by the formula (1-3) or (2).
The reaction is preferably performed at 0 ° C. to the boiling point of the solvent used, and more preferably at 0 ° C. to 80 ° C.
The reaction is usually completed in about 0.5 to 24 hours.
After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.

Reaction formula 3

[Wherein M represents an alkali metal or hydrogen, and other symbols are as defined above. ]

In the reaction formula 3, the compound represented by the formula (1-0) is represented by R ₁ SM and a 4-pyridinecarboxamide derivative represented by the formula (3) which is a raw material compound for the reaction. The thiol compound or thiol salt compound is produced according to the method described in Bioorganic Medicinal Chemistry Letters, 18 (9) 3307-3319 (2010), International Publication No. 2005/85216, or the like.
When M of R ₁ SM is hydrogen, a base is required for the reaction. As the base, known inorganic bases and organic bases can be used, for example, alkali metal hydrides such as sodium hydride and potassium hydride, alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate, or alkaline earth metal carbonates. Salts, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, alkali metal alkoxides such as potassium t-butoxide, triethylamine, tributylamine, diisopropylethylamine, N-methylmorpholine, pyridine, 4- ( N, N-dimethylamino) pyridine, N, N-dimethylaniline, N, N-diethylaniline, 1,5-diazabicyclo [4.3.0] non-5-ene, 1,4-diazabicyclo [2.2 .2] Octane (DABCO), 1,8-diazabicyclo [5. .0] such -7-undecene (DBU) organic bases such like. Preferred are alkali metal hydrides, alkali metal carbonates or alkali metal hydroxides, and more preferred are sodium hydride, potassium carbonate and cesium carbonate.
The amount of the base used may be an amount that is usually 1 to 3 equivalents, preferably 1 to 2.5 equivalents, relative to the compound represented by the formula R ₁ SH.
As long as the solvent is inert to the reaction, known solvents can be widely used. Examples thereof include amide solvents such as N, N-dimethylformamide, solvents such as dimethyl sulfoxide, N-methylpyrrolidone, and N, N′-dimethylimidazolinone. These solvents can be used alone or in combination of two or more as required.
The reaction is preferably performed at 0 ° C. to the boiling point of the solvent used, more preferably at 0 ° C. to 100 ° C.
The reaction is usually completed in about 0.5 to 24 hours.
In the reaction, Z is preferably a fluorine atom or a chlorine atom.

Reaction formula 4-1

[Wherein R ¹ , R ² , G ¹ , G ² , G ³ , G ⁴ , G ⁵ , X, m and Z are as defined above]. ]
In addition, the compound represented by Formula (3) is a precursor of the compound of this invention represented by Formula (1).

Reaction formula 4-2

[Wherein R ¹ , R ² , G ¹ , G ² , G ³ , G ⁴ , G ⁵ , X and m are as defined above]. ]

  The 4-pyridinecarboxamide derivative (3) or (1-0) represented by the above reaction formula 4-1 or reaction formula 4-2 is an aromatic amine compound represented by the above formula (4) and 4- It is produced from the pyridinecarboxylic acid derivative (5) or (6) according to the method described in Bioorganic Medicinal Chemistry Letters, 24 (3) 983-988 (2014), International Publication No. 2012/130780 or the like.

Examples of the condensing agent used in the reaction shown in Reaction Formula 4-1 or Reaction Formula 4-2 include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, N, N′-dicyclohexylcarbodiimide, N Carbodiimide condensing agents such as N'-diisopropylcarbodiimide, and triazine condensing agents such as 4- (4,6-dimethoxy-1,3,5-triazin-2-yl) -4-methylmorpholinium chloride. Can be used. The amount of the condensing agent to be used may be an amount that is usually 1 to 6 equivalents, preferably 1 to 2.5 equivalents, relative to the formula 4-pyridinecarboxylic acid derivative (5) or (6).
In the reaction, a catalyst can be used as necessary. As a catalyst, 1-hydroxybenzotriazole, N, N-dimethylaminopyridine, triethylamine and the like can be used. The amount of the catalyst used may be such that it is usually 0.01 to 1.0 equivalent, preferably 0.02 to 0.2 equivalent, relative to the formula 4-pyridinecarboxylic acid derivative (5) or (6).

As the solvent used in the reaction, known solvents can be widely used as long as they are inert to the reaction. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, halogenation such as methylene chloride, 1,2-dichloroethane, chloroform, etc. Hydrocarbon solvents, ether solvents such as diethyl ether, tetrahydrofuran and 1,4-dioxane, ester solvents such as methyl acetate and ethyl acetate, amide solvents such as N, N-dimethylformamide, N-methylpyrrolidone, N , N′-dimethylimidazolinone, dimethyl sulfoxide, pyridine and the like. These solvents can be used alone or in combination of two or more as required.
The reaction is preferably performed at 0 ° C. to the boiling point of the solvent used, and more preferably at 0 ° C. to 80 ° C.
The reaction is usually completed in about 0.5 to 24 hours.

Reaction Formula 5-1

[Wherein R ² , G ¹ , G ² , G ³ , G ⁴ , G ⁵ , X, m and Z are as defined above]. ]

Reaction formula 5-2

[Wherein R ¹ , R ² , G ¹ , G ² , G ³ , G ⁴ , G ⁵ , X and m are as defined above]. ]

The 4-pyridinecarboxamide derivative (3) or (1-0) represented by the above reaction formula 5-1 or reaction formula 5-2 is an aromatic represented by the above formula (4) in the presence of a base. From an amine compound and a pyridine-4-carbonyl chloride derivative (7) or (8), according to the method described in Bioorganic Medicinal Chemistry Letters, 24 (13) 6693-6702 (2005), International Publication No. 2003/90912, etc. Manufactured.
As the solvent used in the reaction, known solvents can be widely used as long as they are inert to the reaction. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, halogenation such as methylene chloride, 1,2-dichloroethane, chloroform, etc. Hydrocarbon solvents, ether solvents such as diethyl ether, tetrahydrofuran and 1,4-dioxane, ester solvents such as methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, amides such as N, N-dimethylformamide And aprotic polar solvents such as N-methylpyrrolidone, N, N′-dimethylimidazolinone, and pyridine. These solvents can be used alone or in combination of two or more as required.
As the base used in the reaction, known inorganic bases and organic bases can be used. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate and sodium bicarbonate, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal hydrogen such as sodium hydride and potassium hydride. And the like. Examples of the organic base include alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, and amines such as triethylamine, N, N-diisopropylethylamine, and pyridine. These bases may be used alone or in combination of two or more.
Such a base is usually used in an amount of 1 to 100 equivalents, preferably 1 to 2 equivalents, relative to the pyridine-4-carbonyl chloride derivative represented by the formula (7) or (8). obtain.
The reaction can be carried out usually within a range from -78 ° C to the boiling point temperature of the solvent used, and the reaction is preferably carried out at 0 ° C to 40 ° C.
The reaction time varies depending on the reaction temperature and cannot be generally specified, but the reaction is usually completed in about 0.5 to 24 hours.

Representative compounds of the 4-pyridinecarboxamide derivative represented by the formula (1) are shown in Tables 1-1 to 1-5, and the intermediate 3-halo-4- represented by the formula (2). Although the typical compound of a pyridine carboxamide derivative is illustrated in Table 2, this invention is not limited to these.
In the “Property, melting point (° C.)” column of each table, “oil” or “solid” indicates the property, and the numerical value indicates the melting point (° C.).
In each table, “n-” represents normal, “t-” represents tertiary, “i-” represents iso, “Me” represents a methyl group, “Et” represents an ethyl group, “ “Pr” represents a propyl group, and “Bu” represents a butyl group.

Formula (1):

Formula (2):

The compound of the present invention (including 4-pyridinecarboxamide derivative represented by the formula (1) and its N-oxide or a salt thereof, hereinafter the same) is used in agriculture, indoors, forests, livestock, hygiene, etc. It can be used to prevent or control organisms that cause harm in the scene.
Therefore, the compound of the present invention can be used as an active ingredient of agricultural and horticultural agents, particularly agricultural and horticultural insecticides.
Specific usage scenes, target pests, and usage methods are shown below, but the present invention is not limited to these.

  The compound of the present invention can be used for agricultural crops such as food crops (rice, barley, wheat, rye, oats and other wheat, potatoes, sweet potatoes, potatoes, potatoes, potatoes, soybeans, red beans, broad beans, peas, etc. , Beans such as beans, peanuts, corn, persimmon, buckwheat, etc.), vegetables (cabbage, Chinese cabbage, radish, persimmon, broccoli, cauliflower, cruciferous crops such as komatsuna, pumpkin, cucumber, watermelon, mackerel, melon, Cucurbitaceae crops such as zucchini, yugao and garlic, eggplants such as eggplants, tomatoes, peppers, eggplants such as red pepper, shrimp, mushrooms such as ladle, red crustacean crops such as spinach and ducks, carrots, mitsuba and parsley Celery crops such as celery and udon, asteraceae crops such as lettuce and burdock, garlic, onion, leek, leek, leeks, etc. (Paragus, shiso, lotus root, etc.), mushrooms (shiitake, mushrooms, etc.), fruit trees / fruits (citrus fruits, apples, pears, peaches, plums, cherry peaches, Lee, apricots, persimmons, persimmons, persimmons, no fruit fruits, Akibi, blueberries, Raspberries, pineapples, mangoes, kiwi fruits, bananas, strawberries, olives, walnuts, chestnuts, almonds, etc.), fragrances and other crops (lavender, rosemary, thyme, sage, pepper, ginger etc.), special crops (cigarettes, Tea, sugar beet, sugar cane, igusa, sesame, konjac, hops, cotton, hemp, olives, rubber, coffee, rapeseed, sunflower, mulberry, etc., pasture and forage crops (timothy, clover, alfalfa, etc.) Corn, sorghum, grasses such as orchardgrass), turf (Korean turf, bentgrass, etc.), forest trees (Todomatsu) Spruce, pine, hiba, cedar, coral, etc. and ornamental plants (kiku, rose, carnation, lily, eustoma, perennial haze, herbs and orchids such as orchid, orchid, ginkgo, cherry, aoki, etc. It can also be used for pests such as arthropods, molluscs, nematodes, etc. that damage garden trees. Specific pests include:

  Lepidoptera from the arthropoda class (eg, Helicoverpa armigera, Heliothis spp., Agrotis segetum, Autographa nigrisigna, Trichoplusia ni) ), Mamestra brassicae, Spodoptera exigua, Spodoptera litura, etc., Plutella xylostella, etc. honmai), Midarekamonmonaki (Archips fuscocupreanus), Chamonaki (Homona magnanima), Chanohosoga (Caloptilia theivora), Nashihimeshinsukui (Grapholita molesta), etc. malinella), peach leaf moth (Lyonetia clerkella), etc. Rhynidae (Phyllocnistis citrella) etc., Hosogoda family (Phyllonorycter ringoniella), etc. , Pectinophora gossypiella, etc., Carposina niponensis, etc., Cossus jezoensis, etc., Nemapogon granella, etc. Hiloheria Oiraga (Parasa lepida), Himekuroiraga (Scopelodes contracus), etc. ethes punctiferlis), cotton moth (Diaphania indica), Parapediasia teterrella, etc., Locastra muscosalis, etc. Etc., Pieris rapae crucivora, etc., Lycaenidae (Lampides boeticus), etc., Ascotis selenaria, etc. Killer whale (Phalera flavescens), etc. The stag beetle Birds (Spilosoma imparilis), such as the United States white Arctiidae (Hyphantria cunea), Grape berry moth (Endopiza viteana), adult codling moth (Laspeyresia pomonella), etc.), larvae and eggs;

  Coleoptera (for example, Anomala cuprea, Popillia japonica, Oxycetonia jucunda, Anomala geniculata, Aventala lus, etc.) , Anchoplidae (Melanotus fortnumi), Ephiachachidae (Epilachna vigintioctopunctata), Anoplophora malasiaca, Pyramidae (Xylotrechus) Aulacophora femoralis, root worm species (Diabrotica spp.), Phyllotreta striolata, tortoise beetle (Cassida nebulosa), red beetle (Phaedon brassicae), rice beetle (Oulema oryzae), Mexican beetle (Epilachna) Leptinotarsa decemlineata), Rhynchites heros, etc., Cylas formicarius, Curculio sikkimensis, L Adults, larvae and eggs of Anthonomus gradis grandis), Sphenophrus venatus vestitus, etc., Epuraea domina, etc.

  Heteroptera from the order of the Hemiptera (eg, Eurydema rugosum, Eysarcoris lewisi, Eysarcoris parvus, Nezara virida, Nezara virida) Stink bugs (Plautia stali), Halymorpha mista, etc., Urochela luteovoria, etc. , Cletus punctiger, etc., Leptocorisa chinensis etc., Dysdeercus cingulatus etc., Stephanitis n pyritis , Apolygu (Apolygu) s spinolai), adult larvae and eggs such as Stenotus rubrovittalus, Trichonotylus coelestialium, etc. (Megacopta punctatissimum), etc .;

  Hemioptera Homoptera (eg Platypleura kaempferi, etc., Arboridia apicalis, Empoasca onukii, Nepeps c) , Nephotettix virescens, etc. Various biotypes of citrus whitefly (Diaphorina citri), Aleurocanthus spiniferus, Silverleaf whitefly (Bemisia argentifolii), tobacco whitefly (Bemisia tabaci), citrus whitefly (DialeurodesTrial), rodes vaporariorum, etc. Aphids (Brevicoryne brassicae), Komikan aphids (Toxoptera aurantii), Citrus aphids (Toxoptera citricidus), Elderly aphids (Aulacorthum magnoliae), Nasia aphids (Schizaphis piricola), Nasimidio aphids (Nippol, Nippol) Lipaphis erysimi), Hyalopterus pruni, Chrysanthemum aphid (Pleotrichophorus chrysanthemi), Macrosiphoniella sanborni, Broad bean aphid (Megoura crassicauda), Rose Nagato aphids (Sitobion ibarae), tulip beetle aphids (Macrosiphum euphorbiae), Chinese aphids (Myzus varians), peach aphids (Myzus persicae), okabano aphids (Rhopalosiphum rufiabdominalis), hum Rubi hops Aphids (Sitobion akebiae), Apple rotifer (Eriosoma lanigerum), etc., Icerya purchasi, etc. (Phenacoccus kraunhiae), etc., Anchovy (Ceroplastes ceriferus), Ruby Beetle (Ceroplastes rubens), etc., Aonidiella aurantii, Comstockaspis perniciosa , Adults, larvae and eggs of scale insects (Pseudaulacaspis pentagoa), scale insects (Unaspis yanonensis, etc.);

  Thysanoptera (for example, Thrips palma, Thripsella, Thripsella, Thripsella, Thripsella, Thripsella, Thripsella, Thripsella) Yellow thrips (Frankliniella occidentalis), Croton thrips (Heliothrips haemorrhoidalis), etc.

  Hymenoptera (for example, Athalia rosae ruficornis), Arge pagana, etc., Arge mali, etc. Barbet bees (Megachile nipponica nipponica) and other adults such as the black ants of the ant family (Formica japonica), Mikado-Oari (Camponotus kiusiuensis), Black-headed ants (Lasius fuliginosus), Fire ant (Solenopsis richteri, S. invicta, S. geminata, etc.) Larvae and eggs;

  Diptera (e.g., Asphondylia yushimai), etc., Rhacochlaena japonica, Bactrocera cucurbitae, etc., Hola rel Drosophila suzukii and other species of the genus Derophila, Liriomyza trifolii, tomatoes, Liriomyza sativae, Chromatomyia horticola, and Agromyza ormyza flies. Adults, larvae and eggs of the fly (Delia platura), the onion fly (Delia antiqua, etc.);

  Orthoptera (eg, Locusta migratoria, Grasshopper, Ruspolia lineosa), Teleogryllus emma, Truljalia hibinonis, etc. ), Etc., adults, larvae and eggs of grasshoppers (Oxya yezoensis, etc.);

  Adults, larvae and eggs from the order of the Isoptera (eg, Odontotermes formosanus).

  Adults, larvae and eggs of the order Dermaptera (for example, Labidura riparia).

  Adults, larvae and eggs of Arthropoda elegans, Collembola (eg, Sminthurus viridis, etc., Onychiurus matsumotoi, etc.);

  Adults, larvae and eggs of Arthropoda molluscidae Isopada (eg Armadillidium vulgare, etc.)

  Acari (for example, Polyphagotarsonemus latus), Phytonemus pallidus, etc., such as Penthaleus major, and Brevipalpus lewisi), southern spider mite (Brevipalpus phoenicis), etc. Oligonychus ununguis), Chrysanthemum spider mite (Bryobia eharai), Scarlet spider mite (Eotetranychus kankitus), Clover spider mite (Bryobia praetiosa), etc. ), Nisena Scarlet mite (Eriophyes chibaensis), Tulip spider mite (Aceria tulipae), Grape spider mite (Colomerus vitis), Scarlet mite (Aculus fockeui), Scarlet mite (Calacarus carinatus), etc. Adult larvae, eggs and eggs;

  Archaenioglossa (eg, Pomacea canaliculata), for example, Plumonata (eg, Achatina fulica), slugs in the amphiidae family (Meghimatium bilineatum), Merax gagates of the family Nymphalidae, Lehmannina valentiana, Acusta despecta sieboldiana, etc .;

  Tylenchida (eg, Anguinaceae, Ditylenchus destructor), Tylenchorhynchus claytoni, etc., Platylenx (Pratylenchus) ), Minoregusarusenchu (Pratylenchus coffeae), etc. Nematodes (Criconema jaejuense), Anguinaceae strawberry nematodes (Nothotylenchus acris), Aferenchoides strawberry nematodes (Aphelecchoides fragarriae, etc.);

  Coleoptera (Dipridae, for example, Xiphinema sp., Trichodols Trichodorus sp.), Etc .;

Examples include fungi and bacteria such as Eumycota, Myxomycota, Bacteriomycota, Actinomycota, and the like.

  The compound of the present invention works indoors in buildings including ordinary houses, and harms or corrupts wood and its processed wooden furniture, stored food, clothing, books, etc. It can also be used to control paw animals and fungi. Specific pests include:

  Termites of the Arthropoda class of insects (eg, Coptotermes formosanus, Reticulitermes speratus), other termites of the genus Reticulitermes (Reticulitermes hesperus, R. tibialis, R. flavipes, R. lucifugus, R. santonensis, etc.), American termite minor (Incisitermes minor), termite family termite (Odontotermes formosanus), termite family Hodotermopsis jzponica, lepidoptera termite adult larvae (Cryptotermes domesticus) And eggs;

  Coleoptera (for example, Sitophilus zeamais), Sitophilus zeamais, etc., weevil (Callosobruchus chinensis), pea weevil (Bruchus pisorum), brilliant worm (us) Thornium beetle (Tribolium castaneum), Tribolium confusum, etc. (Stegobium paniceum), etc., Attagenus unicolor japonicus, Anthrenus verbasci, Dermestes maculatus, etc. Gibium aequinnoctiale, etc., adults such as Dinoderus minutus, Rhizopertha dominica, etc.

  Lepidoptera (eg, Cadra cautella, Ephestia kuehniella), Plodia interpunctella, etc., Sitotroga cerealella, Tinea, etc. adults, larvae and eggs of translucens), Koiga (Tineola bisselliella, etc.);

  Adults, larvae, and eggs of the order scallop (for example, Lepinotus reticulatus, Liposcelis bostrychophilus, etc.):

  Adults, larvae and eggs of cockroach (eg, Blattella germanica), cockroach (Periplaneta fuliginosa), cockroach (Periplaneta japonica, etc.);

  Adults, larvae and eggs of wasps (eg, Monomorium pharaoni, Monomorium nipponense, etc.);

  Adults, larvae and eggs of the order (for example, Ctenolepisma villosa, Lepisma saccharina);

  Adults, larvae and eggs of flies (for example, Drosophila melangogaster, Piophila casei, etc.);

Examples include adults, larvae and eggs of arthropod spider mites (for example, Tyrophagus putrescentiae, Lardoglyphus konoi, Carpoglyphus lactis, etc.).

  The compounds of the present invention can also be used to control pests that harm or weaken trees in natural forests, artificial forests and urban green spaces. Specific pests include:

  Lepidoptera of the arthropod gland (for example, Calliteara argentata, Euproctis pseudoconspersa, Orygia recens approximans, Euproctis subflava, Lymantria dispar, etc.) Obikareha (Malacosoma neustria testacea), Matsukareha (Dendrolimus spectabilis), Tsukakareha (Dendrolimus superans), etc. (Ptycholoma lecheana circumclusana), Cydia kurokoi, Cydia cryptomeriae, etc., Sprigosoma imparilis, Hyphantria cunea, etc. Hiro Helicopter Oiraga (Parasa lepida), Himekuroiraga (Scopelodes contracus), adult Tenguiraga (Microleon longipalpis), etc.), larvae and eggs;

  Coleoptera (for example, Anomala rufocuprea, Heptophylla picea), Agrilus spinipennis, and the like, Basilepta pallidula, etc., Weevil weevil (Scepticus griseus), Shirahoshizo insidiosus, etc., Weevil weevil (Sipalinus gigas), etc. aceris), etc., adults, larvae and eggs of the genus Rhizopertha dominica)

  Stink bugs (for example, Cinara todocola of the aphid family, Adelges japonicus, etc. of the aphid family, Aspidiotus cryptomeriae, etc. ceriferus) etc) adults, larvae and eggs;

  Adults, larvae and eggs of bees (for example, Pachynematus itoi), Nebeepris sertifer, such as Dr. Bee, Dryocosmus kuriohilus, etc .;

  Flies (for example, Tipula aino in the family Ganbo, etc., Strobilomyia laricicola, etc., Contarinia inouyei, adults of the Contarinia matsusintome, etc.) And eggs;

  Adults, larvae and eggs of arthropod spider mites (eg, Oligonichus hondoensis, Oligonichus ununguis, etc.);

Linear animal genus genus Tylenoptera (for example, Bursaphelenchus xylophilus)
Is mentioned.

  The compounds of the present invention are arthropods that parasitize internally or externally to vertebrates, particularly domestic animals and pets such as cattle, sheep, goats, horses, pigs, poultry, dogs, cats and fish, which are warm-blooded vertebrates. It can also be used to prevent, treat or control animals, nematodes, flukes, tapeworms, and protozoa. In addition to the above, target animal species include rodents such as mice, rats, hamsters and squirrels, carnivores such as ferrets, avian pets such as ducks and pigeons, experimental animals, and the like. Specific pests include:

  Arthropoda insects (eg, Tabanus rufidens, Tabanus chrysurus, etc., Musca bezzii, Musca domestica, Stomoxys calcitrans, etc.) Gasterophilus intestinalis, etc., Hypoderma bovis, etc., Oestrus ovis, etc., Aldrichina grahami, etc. Etc., Cyprus pipiens molestus, Culex pipiens molestus, Culex pipiens molestus, Psychoda alternata, etc. , Anopheles sinensis, Culex pipiens tria eniorhynchus summorosus), Ades albopictus, etc., Simulium iwatense, Prosimulium yezoense, etc. ;

  Adults, larvae and eggs of fleas (eg, Pulex irritans, Ctenocephalides canis);

  Lice (for example, Haematopinidae suis, Haematopinidae eurysternus), Damalinia bovis, etc., Linognathus vituli, (Menopon gallinae etc.) adults, larvae and eggs;

  Arthropod arachnid mites (eg, Varroa jacobsoni), tick-spotted ticks (Haemaphysalis longicornis), Yamato tick (Ixodes ovatus), tick (Amphidia) such as testudinarium), oriental mite (Ornithonyssus sylvialum), etc., Dermanyssus gallinae, etc. (Knemidocoptes mutans, etc.) adults, larvae and eggs of the family Mite, Otodectes cynotis, Psoroptes communis, etc .;

Coleoptera of linear animal gates (eg, caterpillars, swine nematodes, swine lungworms, ciliate nematodes, bovine intestinal nodules, etc .;
Roundworms (for example, swine roundworm, chicken roundworm, etc.);
Phlegm reticulata (eg, Schistosoma japonicum, liver tetsu, deer buccal fluke, Westermann lung fluke, Japanese chicken egg fluke)
Cestiidae (for example, foliate, expanded, Beneden, square, striate, and ringworm);
Root flagellate (eg, Histomonas), Protoflagellate (eg, Leishmania, Trypanosoma, etc.), Polyflagellate (eg, Giardia, etc.), Trichomonas (eg, Trichomonas) ;
Meat quality amoeba (for example, Entamoeba);
Piroplasma subclasses of sporeworms (eg Theilaria, Babesia, etc.), subspores of late spores (eg, Eimeria, Plasmodium, Toxoplasma, etc.)
Is mentioned.

  The compounds of the present invention can also be used to combat pests that are directly harmful or uncomfortable to the human body, or to maintain public health for pests that carry or carry pathogens. Specific pests include:

  Lepidoptera of Arthropoda (eg, Sphrageidus similis), Kunugia undans, etc., Parasa consocia, etc., Artona martini Etc.) adults, larvae and eggs;

  Coleoptera (for example, adults such as Xanthochroa waterhousei), larvae of the scorpion family (Epicauta gorhani), larvae (Paederus fuscipes), larvae, etc .;

  Adults, larvae and eggs of bees (for example, Vespa simillima xanthoptera, etc., Brachyponera chinensis, etc., Batozonellus annulatus, etc.);

  Flies (for example, Armygeres subalbatus), Cypicoides nipponensis, etc., Chironomus yoshimatsui, etc., Simulium nikkoense, etc. Hirosia humilis, etc., Musca domestica, etc., Fannia canicularis, etc., Phormia regina, etc., Sarcophaga peregrina, etc. Adult larvae, eggs and eggs;

  Adults, larvae and eggs of fleas (eg, Pulex irritans)

  Adults, larvae and eggs of cockroach (eg, Blattella germanica), cockroach (Periplaneta americana), black cockroach (Periplaneta fuliginosa), cockroach (Periplaneta japonica, etc.);

  Adults, larvae and eggs of the Orthoptera (eg, Diestrammena japonica, Diestrammena apicalis, etc.)

  Adults, larvae and eggs of lice (for example, Pediculus humanus humanus, Phthhirius pubis, etc.);

  Adults, larvae and eggs of stink bugs (eg, Isyndus obscurus, such as Cimex lectularius);

  Adults, larvae and eggs of the order Arthropoda (Collembola) (eg Hypogastrura communis, etc.)

  Phyemotes ventricosus), Acridaceae, Demodex folliculorum, etc., Dermotophagoides pteronyssinus, etc., Sarcoptes scabiei, etc. egg;

  Genuine spiders (for example, Chiracanthium japonicum), Heteropoda venatoria, etc., Spermophora senoculata, Pilicus angio ), Etc., adults, larvae and eggs of the family Spider family Plexippus paykulli, Plexippus adansoni, etc .;

  Adults, larvae and eggs of the order of scorpions (for example, Isometrus europaeus);

  Adults, larvae and eggs of arthropods of the order Coleoptera (eg, Scolopendra subspinipes mutilans, Scolopendra subspinipes japonica);

  Adults, larvae and eggs of the genus (for example, Thereuronema hilgendofi);

  Adults, larvae and eggs from the order of the arthropod gallopidae (for example, Oxidus gracilis).

  Adults, larvae and eggs of arthropod crustaceans (eg, Porcellio scaber)

Anemone of annelids (for example, Haemadipsa zeylanica japonica)
Is mentioned.

  The compounds of the present invention are particularly valuable for controlling pests that damage crops, natural forests, artificial forests, urban greenery trees and ornamental plants, such as arthropods, gastropods, nematodes. In such situations, the compounds of the present invention may be used in other commercially active formulations, such as insecticides, acaricides, nematicides, fungicides, in their commercially useful formulations and use forms prepared by these formulations. It can also be present as a mixture with agents, synergists, plant regulators, baits or herbicides.

The compound of the present invention can be used as it is or in a form generally usable as an agrochemical, such as wettable powder, granular wettable powder, dry flowable powder, water solvent, emulsion, liquid agent, oil agent, aqueous suspension and aqueous emulsion It can be used in dosage forms such as flowables, capsules, powders, granules, fine granules, baits, tablets, sprays, fumes, aerosols and the like.
In these preparations, the active ingredient compound is generally contained in a total amount of 0 to 99.9% by mass, preferably 0.2 to 90% by mass.
In order to obtain these dosage forms, various agricultural chemical adjuvants conventionally used in the technical field of agricultural and horticultural medicine can be appropriately used. Such agrochemical adjuvants can be used for the purpose of, for example, improving the effects, stabilizing, and improving dispersibility of agricultural and horticultural chemicals.
Examples of the agricultural chemical adjuvant include a carrier (diluent), a spreading agent, an emulsifier, a wetting agent, a dispersing agent, a disintegrating agent, and the like.
Liquid carriers include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, methyl Mention may be made of naphthalene, cyclohexane, animal and vegetable oils, fatty acids and the like. As the solid carrier, clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic and the like can be used.
As the emulsifier and dispersant, ordinary surfactants can be used, for example, higher alcohol sodium sulfate, stearyl trimethyl ammonium chloride, polyoxyethylene alkyl phenyl ether, anionic surfactants such as lauryl betaine, Cationic surfactants, nonionic surfactants, amphoteric surfactants and the like can be used.
Further, spreading agents; wetting agents such as dialkyl sulfosuccinate; fixing agents such as carboxymethyl cellulose and polyvinyl alcohol; disintegrating agents such as sodium lignin sulfonate and sodium lauryl sulfate can be used.
Of course, the compound of this invention can also be mix | blended as an active ingredient by combining 1 type (s) or 2 or more types. In these preparations, the content of the compound of the present invention as an active ingredient is, for example, 0.01 to 99.9% by mass, and preferably selected from the range of 0.2 to 90% by mass. It may be appropriately determined according to various conditions. For example, about 0.5 to 20% by weight, preferably 1 to 10% by weight for powders, about 1 to 90% by weight for wettable powders, preferably about 10 to 10% by weight. In the case of an emulsion, it can be produced so as to contain an active ingredient in an amount of about 1 to 90% by weight, preferably 10 to 40% by weight.

  In order to control arthropods, gastropods, nematodes, and fungi, the foliage of the plant against the place where damage by these pests or where damage is likely to occur In addition to spraying on the soil, it can be applied to the soil, etc., by mixing it with the soil, etc., soil mixing, crop application, floor soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dress, rice box treatment, water surface application It can also be used after being absorbed. It can also be used by soaking seeds in chemicals, seed dressing, seed treatment such as calper treatment, application to nutrient solution in nutrient solution (hydroponic) cultivation, smoke, or trunk injection. When used, it varies depending on the type and amount of pests and the target crop / tree type and cultivation form / growth state, but generally 0.1 to 1000 g, preferably 1 to 100 g, in terms of active ingredient per 10 ares. Apply. To treat this, dilute with water in wettable powder, granule wettable powder, dry flowable powder, water solvent, emulsion, liquid, flowable liquid such as suspension in water, emulsion in water, capsules, etc. Although it differs depending on the type of plant and the cultivation form / growth state, it is generally applied to crops and the like at an application rate of 10 to 1000 liters per 10 ares. Moreover, what is necessary is just to process to a crop etc. in the state of the formulation in a powder agent, a spray agent, or an aerosol agent.

  When the target pest primarily harms plants in the soil or when the drug is absorbed from the roots to control the target pest, for example, the preparation is not diluted or diluted in water. Method of applying to plant stock or seedling nursery, etc., spraying granules to plant stock or nursery for seedling, powder, wettable powder, granular water before sowing or transplanting A method of spraying Japanese sweets, granules, etc. and mixing with the whole soil, before sowing or planting plants, planting holes, crops etc., powder, wettable powder, granule wettable powder, granules, fine granules, The method of spraying etc. is mentioned. For wettable powders, granular wettable powders, aqueous solvents, emulsions, liquids, flowables such as suspensions in water and emulsions in water, capsules, etc., dilute with water, generally 5 to 500 liters per 10 ares In the case of powder, granule, fine granule or bait, etc., it should be spread evenly over the entire area to be treated. What is necessary is just to spread on the soil surface. Spraying or irrigation may be around the seeds, crops or trees that you want to protect from harm. Further, the active ingredient can be mechanically dispersed by tilling during or after spraying.

  As a method for applying paddy rice to a seedling box, the dosage form may differ depending on the time of application such as application at seeding, greening period, application at transplanting, etc., for example, powder, granule wettable powder, granule, fine powder What is necessary is just to apply in dosage forms, such as a granule. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder, granules or fine granules, for example, mixed with floor soil, mixed with soil, mixed into the entire soil, etc. it can. Alternatively, the culture medium and various preparations may be applied alternately in layers.

  As a method of application to paddy fields, solid preparations such as jumbo agents, packs, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields. In addition, at the time of rice planting, an appropriate preparation can be sprayed and injected into the soil as it is or mixed with fertilizer. In addition, by using a chemical solution such as emulsion or flowable as a source of water flowing into a paddy field such as a water mouth or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.

  Seed treatment methods include, for example, a method in which a liquid or solid preparation is diluted or undiluted to immerse the seed in a liquid state to attach and permeate the drug, and a solid preparation or liquid preparation is mixed with the seed. Examples thereof include a method of dressing and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as a resin and a polymer, and a method of spraying around the seed simultaneously with planting. The “seed” for performing the seed treatment means a plant body at an early stage of cultivation used for plant propagation. For example, in addition to seeds, nutrition for bulbs, tubers, seed buds, buds, baskets, bulbs or cuttings cultivation Mention may be made of plants for breeding. In addition, the “soil” or “cultivation carrier” of a plant when applied refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. Any material can be used as long as it can grow, so-called soil, seedling mat, water, etc. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel material, polymer material, rock Examples include wool, glass wool, wood chips, and bark.

  As the treatment of the cultivated plant to be transplanted and the treatment of the seedling raising period, in addition to the direct treatment to the seed, the irrigation treatment of the liquefied drug or the granule spraying treatment to the seedling nursery is preferred. In addition, it is also preferable to treat the granule in the planting hole at the time of planting or to mix it with the cultivation carrier in the vicinity of the transplantation site.

The compounds of the present invention are also valuable for protecting wood (standing trees, fallen trees, processed wood, storage wood or structural wood) from insulting insects such as termites or cucumbers and fungi. In such a situation, it is possible to control oil, emulsion, wettable powder, sol, spraying, pouring, irrigation, application, dusting, granulation, etc. on wood or surrounding soil. it can. Also, oils, emulsions, wettable powders, powders, etc. used in this scene are mixed with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists. In these preparations, the total amount of the active ingredient compounds is 0.0001 to 95% by mass, preferably 0.005 to 10% by mass for oils, powders and granules, emulsions, wettable powders and sols. Then, it may be contained in an amount of 0.01 to 50% by mass. When controlling arthropods or fungi, apply 0.01 to 100 g of active ingredient compound per 1 m ² to the soil or wood surface.

  The compounds of the present invention can be used when storing products such as cereals, fruits, nuts, spices and tobacco as they are, in a powdered state, or mixed in the product. It can be used to protect against fungal damage. In addition, when storing animal products (skin, hair, wool, feathers, etc.) and plant products (cotton, paper, etc.) in a natural or converted state, attacks from Lepidoptera, Coleoptera, Spots and Cockroaches It can be protected, and can be protected from attacks by Lepidoptera, Coleoptera, flies and ticks when storing food such as meat and fish. In such situations, spraying oils, emulsions, wettable powders, powders, etc., installing resin transpiration agents, treating smoke and fumes, installing granules, tablets and poison baits, spraying aerosols, etc. Can be controlled with. These formulations can also be present as a mixture with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists, in these formulations. May contain 0.0001 to 95% by mass of the active ingredient compounds in a total amount.

  The compounds of the present invention prevail or mediate diseases of arthropods, humans and livestock that parasitize the body surface of humans and livestock, causing direct harm such as eating or sucking skin. It is valuable for the control or prevention of arthropods, nematodes, flukes, tapeworms, protozoa, and arthropods that cause discomfort to humans. In such a situation, the compound of the present invention is mixed in a small meal or feed, or a suitable pharmaceutical composition that can be taken orally, such as tablets, pills containing pharmaceutically acceptable carriers and coating substances, Capsules, pastes, gels, beverages, medicinal feeds, medicinal drinking water, medicinal supplements, sustained-release large pills, other sustained-release devices designed to be retained in the gastrointestinal tract, sprays, powders, It can be administered transdermally as grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo and the like. In order to achieve the effect in such an application, generally 0.0001 to 0.1% by mass, preferably 0.001 to 0.01% by mass of the active ingredient compound is contained in the preparation. In addition, as a method for transdermal administration or local administration, a device (for example, a collar, a medallion, an ear tag, or the like) attached to an animal so as to control the arthropod locally or systemically can be used.

  Specific oral administration methods and transdermal administration methods in the case where the compound of the present invention is used as an anthelmintic agent for animals such as livestock and pets or humans are shown below, but are not necessarily limited thereto.

  When administered orally as a medicinal beverage, the beverage is usually a suspension, humectant or other excipient such as bentonite, a suitable non-toxic solvent or water solution, suspension or dispersion. . In general, beverages also contain an antifoam agent. The beverage formulation generally contains 0.01 to 1.0% by weight, preferably 0.01 to 0.1% by weight, of the active ingredient compound.

  When it is desired to administer orally in a dry solid unit dosage form, capsules, pills or tablets containing a predetermined amount of the active ingredient are usually used. These forms of use are obtained by intimately mixing the active ingredient with suitably finely divided diluents, fillers, disintegrants and / or binders such as starch, lactose, talc, magnesium stearate, vegetable gums and the like. Manufactured. Such unit use formulations can vary widely in the weight and content of the anthelmintic depending on the type of host animal to be treated, the degree of infection and the type of parasite and the body weight of the host.

  When administered by animal feed, the active ingredient compound can be homogeneously dispersed in the feed, used as a top dressing or in the form of pellets. In order to achieve a normally desirable antiparasitic effect, the active ingredient compound is contained in the final feed in an amount of 0.0001 to 0.05% by mass, preferably 0.0005 to 0.01% by mass.

  Those dissolved or dispersed in a liquid carrier vehicle can be administered parenterally to the animal by intragastric, intramuscular, intratracheal or subcutaneous injection. For parenteral administration, the active compounds are preferably mixed with suitable vegetable oils, such as peanut oil, cottonseed oil. Such a formulation generally contains 0.05 to 50 mass%, preferably 0.1 to 5.0 mass%, of the active ingredient compound.

  Alternatively, the active ingredient compound may be administered locally by mixing with a suitable carrier such as dimethyl sulfoxide or a hydrocarbon solvent. This formulation is applied directly to the external surface of the animal by spraying or direct injection.

  In addition, the compound of the present invention can be used as an anthelmintic agent for arthropods that cause direct harm, or as an anthelmintic agent for arthropods that are mediators of diseases, as an oil agent against the surrounding environment in which these pests can potentially , Spraying, injecting, irrigating and coating of emulsions, wettable powders, spraying of powders, fumigants, mosquito coils, self-combustion smoke chemicals, chemical reaction type aerosols, fogging, etc. By methods such as treatment of smoke, ULV, etc., installation of granules, tablets and poisonous bait, or addition of floating powder, granules, etc. to waterways, wells, reservoirs, water tanks and other running water or water It can also be used. Furthermore, it can be controlled in the same way as the above-mentioned methods for farming, forest pests, etc., and for flies, etc., it is mixed in the feed of livestock. For example, a method of volatilizing the mosquitoes into the air with an electric mosquito trap is also effective. The preparations in these use forms can exist as a mixture with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists. In this preparation, the active ingredient compounds are contained in a total amount of 0.0001 to 95% by mass.

  The compounds according to the invention can also be present as admixtures with other active compounds. Especially for the control of pests such as arthropods, gastropods and nematodes that damage plants by using them in combination with compounds (insecticides) that have insecticidal, acaricidal or nematicidal activity Therefore, it is possible to expand the number of pests to be controlled, and a synergistic effect such as a reduction in dosage can be expected. Specific active compounds thereof include the following:

  Organophosphorus agents (eg, acephate, azinphos-methyl, chlorpyrifos, diazinon, dichlorvos, dimeton-S-methyl, dimethoate, Dimethylvinphos, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, monocrotophos (methidathion) monocrotophos, naled, oxydeprophos, oxideprofos, parathion, phenthoate, phosalone, pirimiphos-methyl, pyridafenthion, profenofos nofos, prothiofos, propaphos, pyraclofos, salithion, sulprofos, thiometon, tetrachlorvinfos, trichlorphon, vamidothion etc);

  Carbamate agents (eg, alanycarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbofuran, carbosulfan, ethiofencarb, fenobucarb, furothiocarb) (Furathiocarb, isoprocarb, metomyl, metolcarb, pirimicarb, propoxur, thiodicarb, etc.);

  Organochlorine agents (eg, aldrin, chlordane, DDT (p, p'-DDT), endosulfan, lindane, etc.);

  Pyrethroids (eg, acrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, deltamethrin, deltamethrin) deltamethrin), etofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenprox, fluvalinate, furamethrin, halofen Proxrin (halfenprox), imiprothrin permethrin, phenothrin, prallethrin, pyrethrin, resmethrin, silaful off Down (silafluofen), tefluthrin (tefluthrin), tralomethrin (tralomethrin), transfluthrin (Transfluthrin), etc.);

  Neonicotinoid agents (eg, acetamiprid, clothianidin, dinotefran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam);

  Diamide agents (eg, chlorantraniliprore, cyantraniliprore, cyclaniliprore, tetraniliprole, flubenziamid, etc.);

  Insect growth control agents such as benzoyl urea (eg, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron) ), Lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, cyromazine, etc.);

  Phenylpyrazole agents (eg, ethiprole, fipronil, acetoprole, pyrafluoprole, pyriplore, etc.);

  Nereistoxin agents (eg, bensultap, cartap, thiocyclam, thiosultap, etc.);

  Diacylhydrazones (eg, chromafenozide, halofenozide, methoxyfenozide, tebufenozide),

  Juvenile hormone agents (eg, diofenolan, fenoxycarb, hydroprene, methoprene, pyriproxyfen, etc.);

  Insecticidal substances produced by microorganisms (for example, abamectin, emamectin-benzoate, ivermectin, lepimectin, milbemectin, nemadectin, nikkomycin) , Polyoxin complex (polioxin), spinetram, spinosad, BT agent (Bacillus thuringiensis and insecticidal protein product)), etc .;

Insecticides derived from natural products (for example, anabasine, azadiractin, deguelin, fatty acid glycerides (decanolyoctanoylglycerol), hydroxypropyl starch, soy lecithin, nicotine) ), Nornicotine, oreic acid sodium salt, machine oil (petroleum oil), propylene glycol monolaurate, rape oil, rotenone, sorbitan fatty acid ester ( Sorbitan fatty acid ester), starch, etc .;
Other insecticides include, for example, afidopyropen, broflanilide, chlorfenapyr, diafenthiuron, dicfenomezotiaz, dicloromezotiaz, DBEDC (dodecylbenzenesulphonic acidbisethylenediamine copper [II] salt (Flonicamid), flometoquin, flufenerim, fluhexafon, flupyradifurone, hydramethylnon, indoxacarb, metaflumizone, metaaldehyde , Nicotin sulfate, pymetrozine, pyridalyl, pyrifluquinqzon, spirotetramat, sulfuramid, sulfluramid (Sulfoxaflor), triflupromazine meso pyridinium beam (triflumezopyrim), tolfenpyrad (tolfenpyrad), triazamate (Triazamate), etc.);

  Acaricides (for example, acequinocyl, amidoflumet, amitraz, azocyclotin, benzoximate, bifenazate, binapacryl, phenisobromolate, bromopropylate, Quinomethionat, clofentezine, cyenopyrafen, cyflumetofen, tricyclohexyltin hydroxide, dicofol, dienochlor, diflovidazin, oxa , Fenazaflor, fenazaquin, fenbutatin oxide, phenothiocarb, fenpyroximate, fluacrypy rim), hexythiazox, pirimidifen, polynactins, propargite, pyflubumide, pyridaben, spirodiclofen, spiromesifen, tebol (Tebufenpyrad, tetradifon, etc.);

  Nematicides (eg, aluminum phosphide, benclothiaz, cadusafos, etoprophos, fluensulfone, fluopyram, fosthiazate, furfural) , Imiciafos, levamisol hydrochloride, mesulfenfos, metam-ammonium, methyl isothiocyanate, moranteltartarate, oxamyl, thifluzamide, thixaphene thioxazafen) etc);

Poisonous baits (eg, chlorphacinone, coumatetralyl, diphacinone, sodium fluoracetate, warfarin, etc.)
Can be mentioned.

  The compounds of the present invention can also be present as a mixture with other active compounds other than compounds having insecticidal, acaricidal or nematicidal activity. In order to control diseases and / or weeds that occur at the same time of use, it can be used in combination with a compound having fungicidal activity, herbicidal activity, or plant growth regulating activity, thereby reducing the control effort and reducing the dosage. Synergistic effects can be expected. Moreover, more effective control effects, such as a synergistic effect, can be expected by using a mixture with a repellent or a synergist.

  Specific active compounds thereof include, for example, the following fungicides:

  Bactericides that inhibit nucleic acid synthesis (eg, benalaxyl, benalaxyl m, furalaxyl, metalaxyl, metalaxyl m, oxadixyl, ofurace, buprimate) (Bupirimate), dimethirimol, dimethirimol, ethirimol, hydroxyioxazole, hymexazol, octirinone, oxolinic acid, etc.);

  Agents that inhibit mitosis and cell division (eg, benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, dietofencarb) , Zoxamide, zarilamid, ethaboxam, penencycuron, fluopicolide, etc.);

  Bactericides that inhibit respiration (eg, diflumetorim, tolfenpyrad, tebufenpyrad, fenazaquin, pyridaben, fenpyroximate, pyrimidifone, rotenidone) benodanil), flutolanil, mepronil, isofetamid, fluopyram, fenfuram, carboxin, oxycarboxin, thiofluzamide, benzobindiflupyr (Benzovindiflupyr), bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane (s edaxane, boscalid, pyraziflumid, azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin ), Pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, kresoxim-methyl, trifloxystrobin, dimoxystrobin (Dimoxystrobin), phenaminestrobin, metominostrobin, orizastrobin, famoxadone, fluoxastrobin, fenamidone, pyribencarb, cyazofamid, amis Bromine (amisulbrom), binapacryl (binapacryl), meptyldinocap (meptyldinocap), dinocap (dinocap), fluazinam (fluazinam), silthiofam (silthiopham), Ametokutorajin (ametoctradin), Tebufurokin (Tebfloquin), etc.);

  Bactericides that inhibit amino acid and protein synthesis (eg, andoprim, cyprodinil, mepanipyrim, pyrimethanil, blasticidin s, kasugamycin, streptomycin) ), Oxytetracycline, mildiomycin, etc.);

  Bactericides that inhibit signal transduction (eg quinoxyfen, proquinazid, fenpiclonil, fludioxonil, fludioxonil, chlozolinate, iprodione, procymidone, clocloolin, etc.) );

  Bactericides that inhibit lipid and cell membrane synthesis (eg, edifenphos, iprobenfos, pyrazophos, isoprothiolane, biphenyl, chloroneb, quintozene, technazen, torquelophos Methyl (tolclofos-methyl), echlomezole, iodocarb, propamocarb, prothiocarb, etc.);

  Bactericides that inhibit cell membrane sterol biosynthesis (eg, triforine, pyrifenox, pyrisoxazole, fenarimol, nuarimol, imazalil, oxpoconazole, Pefurazoate, prochloraz, triflumizole, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole , Epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, fluotrimazole, fluco Furazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanil, penconazole, propiconazole propiconazole), simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, uniconazole p ( uniconazole-p), buthiobate, diclobutrazol, aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidine Fenpropidin), Piperarin (Piperalin), spiroxamine (Spiroxamine), fenhexamid (Fenhexamid), Fenpirazamin (Fenpyrazamine), naftifine, terbinafine (terbinafine), etc.);

Bactericides that inhibit cell wall biosynthesis (eg, validamycin, polyoxin, dimetomorph, flumorph, pyrimorph, benchthiavalicarb, iprovalicarb, valenarate (Valifenalate), mandipropamid, etc. As bactericides that inhibit cell wall melanin synthesis, for example, fthalide, pyroquilon, tricyclazole, carpropamid, diclocymet, phenoxanil etc);

  Fungicides that induce host plant resistance (eg, probenazole, thiadinil, isothianil, laminarin, extract from giant knotweed, acibenzolar-smethyl) -methyl) etc.];

  Bactericides that inhibit multiple action points (eg, copper, dbedc (complex of bis (ethylenediamine) copper-bis- (dodecylbenzenesulfonic acid)), cupric hydroxide, copper nonylphenol sulfonate (copper) nonylphenol sulfonate, basic copper oxychloride, basic copper sulfate, organic copper (oxine-copper), sulfur, lime-sulfur compound (calcium polysulfide), silver (silver), dd (1,3-dichloropropene), dazomet, methyl bromide, methylisothiocyanate, metam-ammonium, mancozeb, maneb, metiram , Propineb, thiram, zinc sulfate, zineb, ziram, captan, captafol, folpet, chloro Talonil, dichlofluanid, tolylfluanid, guazatine, iminoctadine acetate, iminoctadine-dbs, triil (anilazine), dithianon ( dithianon), chinomethionat, fluoroimide, dithane-stainless, etc.);

Other fungicides (eg, cymoxanil, fosetyl, phosphoric acid, phosphite, tecloftalam, triazoxid, flusulfamide, dichromedin ( diclomezine, metasulfocarb, cyflufenamid, metrafenone, pyriofenone, dodine, flutianil, ferimzone, oxathiapiprolin, oxathiapiprolin, oxathiapiprolin tolprocarb), picarbutrazox, wo2005081174, wo2011811742, machine oil (petroleum oil), organic oil (organic oil), potassium hydrogen carbonate (potassium hydrogen carbonate), sodium hydrogen carbonate (sodium hydrogen carbonate), hypochlorous acid Sodium salt (sodi um hypochlorite, calcium carbonate, benthiazole, diclobutrazol, flumetover, thiadiazin, dichlone, organotin (organo-tin), Shiitake mycelium extract (extract from mushroom, etc.)
Is mentioned.

  Examples of the compound having herbicidal activity include aclonifen, acifluofen-sodium, alachlor, alloxydim, amicarbazone, amidosulfuron, anilophos ( anilofos, asuram, atrazine, azimsulfuron, benfuresate, bensulfuron-methyl, bentazone, benthiocarb, benzobicyclon, Benzofenap, bialaphos, bifenox, bromobutide, bromoxynil, butamifos, cafenstrole, calcium peroxide, carbe Carbetamide, cinosulfuron, clomeprop, cyclosulfamuron, cyhalofop-butyl, daimuron, desmedipham, diclofopop -methyl), diflufenican, dimefuron, dimethametryn, dinoterb, diquat, diuron, esprocarb, ethiozin, ethofsate, ethofsate Ethoxysulfuron, etobenzanid, fenoxaprop-P-ethyl, fentrazamide, flucarbazone, flufenacet, flurtamone, fluthiase Fluthiacet-methyl, foramsulfuron, glufosinate-ammonium, glyphosate-isopropyl amine, glyphosate-trimesium, imazapyr, imazosulfuron (imazosulfuron) ), Indanofan, iodosufluron, ioxynil-octanoate, isoproturon, isoxadifen, isoxaflutole, lactofen, linuron, mefenacet (Mefenacet), mesosulfuron, metamitron, methabenzthiazuron, metosulam, metribuzin, napropamide, nebur on), oxadiargyl, oxadiazon, oxaziclomefone, paraquat, pendimethalin, pentoxazone, phenmedipham, pretilachlor, propoxycarbazone (Propoxycarbazone), prosulfocarb, pyraclonil, pyraflufen n-ethyl, pyrazolate, pyrazosulfuro n-ethyl, pyributicarb, pyriphthalide ( pyriftalid, pyriminobac-methyl, quizalofop-ethyl, sethoxydim, simazine, sulcotrion, sulfentrazone, tenylchlor (Thenylchlor), triaziflam, tribufos (tribufos) and the like can be exemplified.

  The compound of the present invention is a compound having a plant growth regulating action (for example, 1-naphthylacetic acid, 4-CPA (4-CPA), benzylaminopurine, butralin, Calcium chloride, calcium formate, calcium peroxide, calcium sulfate, chlormequat chloride, choline, cyanamide, cyclanilide, Daminozide, decyl alcohol, dichlorjop, ethephon, etychlozate, flurprimidol, forclorfenuron, gibberellic acid , Indolebutyric acid, maleic acid Radium potassium (maleic hydrazide potassium salt), mefenpyr (mefenpyr), mepiquat chloride (mepiquat chloride), oxine sulfate (oxine sulfate, 8-hydroxyquinoline sulfate), paclobutrazol (paclobutrazol), paraffin (paraffin), prohexa Mix with dihexon calcium salt (prohexadione-calcium), prohydrojasmon (prohydrojasmon), thidiazuron (thidiazuron), trinexapac ethyl (trinexapac), uniconazole P (uniconazole-P), wax (wax)) You can also.

  The compounds of the present invention are:

Repellents (eg capsaicin, carane-3,4-diol, citronellal, deet, dimethyl phthalate, hinokitiol, limonene) ), Linalool, menthol, menthone, naphthalene, thiram, etc.);
Synergists (eg, methylenedioxynaphthalene, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentynyl) phthalimide), phenyl salioxon, piperonyl butoxide, safrole, sesamex, sesamin, sulfoxide, triphenyl phosphate, valbutin etc)
It can also be used as a mixture.

  The compound of the present invention is used as a biopesticide, for example, cytoplasmic polyhedrosis virus (CPV), insect pox virus (Entomopox virus, EPV), granule disease virus (Granulosis virus, GV), nuclear polyhedrosis virus (Nuclear). virus preparations such as polyhedrosis virus (NPV), Beauveria bassiana, Beauveria brongniartii, Monocrosporium phymatophagum, Paecilomyces fumosorose peneuri , Steinernema carpocapsae, Steinernema glaseri, Steinernema kushidai, Verticillium lecanii, etc. Microbial pesticides used as chews, Agrobacterium radiobactor, Bacillus subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02 (Pseudomonas CAB-02), Pseudomonas fluorescens, Talaromyces, Trichoderma atroviride, Trichoderma lignorum, etc. The same effect can be expected when used in combination with agrochemicals, biopesticides used as herbicides such as Xanthomonas campestris.

  Furthermore, as biopesticides, for example, Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidoletes aphidimyza, Aphidoletes aphidimyza, Chrysoperia carnea, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Haripi ris rid Crested bee (Hemiptarsenus varicornis), Scarlet (Neochrysocharis formosa), Scarlet beetle (Orius sauteri), Scarlet beetle (Orius strigicollis), Phytoseiulus persimilis Natural enemies such as black leopard turtle (Pilophorus typicus), Piocoris varius, codlelure, cuelure, geraniol, gyptol, liblure, looplure, looplure It can also be used in combination with pheromone agents such as eugenol, methyl eugenol, orfralure, peachflure, phycilure, pyrimalure, turpentine.

  Hereinafter, although an Example, a formulation example, and a test example are further described and demonstrated in detail about this invention, the range of this invention is not limited at all by these Examples, a formulation example, and a test example.

Example 1-1
Synthesis of 3-fluoro-N- (5-trifluoromethylpyridin-2-yl) -4-pyridinecarboxamide (Compound No. B-1) 3-Fluoro-pyridine-4-carboxylic acid (0.50 g), 2- A solution of amino-5-trifluoromethylpyridine (0.60 g) and 1-hydroxybenzotriazole monohydrate (54 mg) in pyridine (8 ml) was added to 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride ( 0.95 g) was added at room temperature, and the mixture was stirred at room temperature for 3 hours. Ethyl acetate and water were added to the reaction solution, the organic layer was separated, and the organic layer was further washed with water. The organic layer was dried over anhydrous magnesium sulfate, and then the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and 0.89 g (mp119-123 ^° C.) of 3-fluoro-N- (5-trifluoromethylpyridin-2-yl) -4-pyridinecarboxamide (Compound No. B-1) was obtained. ).

Example 1-2
Synthesis of 3-ethylsulfanyl-N- (5-trifluoromethylpyridin-2-yl) -4-pyridinecarboxamide (Compound No .: A-3)
To a solution of 3-fluoro-N- (5-trifluoromethylpyridin-2-yl) -4-pyridinecarboxamide (0.57 g) in N, N-dimethylformamide (4 ml) was added sodium ethanethiolate (0.26 g) at room temperature. The mixture was further stirred at room temperature for 2 hours. Ethyl acetate and water were added to the reaction solution, the organic layer was separated, and the organic layer was further washed with water. The organic layer was dried over anhydrous magnesium sulfate, and then the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and 0.60 g (mp60-69 ^° ) of 3-ethylsulfanyl-N- (5-trifluoromethylpyridin-2-yl) -4-pyridinecarboxamide (Compound No .: A-3) was obtained. C).

Example 2
Synthesis of 3-ethylsulfanyl-N-methyl-N- (5-trifluoromethylpyridin-2-yl) -4-pyridinecarboxamide (Compound No .: A-6)
3-ethylsulfanyl-N- (5-trifluoromethylpyridin-2-yl) -4-pyridinecarboxamide (0.49 g) in N, N-dimethylformamide (5 ml) in 60% sodium hydride (oil) (71 mg ) And stirred at room temperature for 20 minutes. Methyl iodide (0.13 ml) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hours. Ethyl acetate and water were added to the reaction solution, the organic layer was separated, and the organic layer was further washed with water. The organic layer was dried over anhydrous magnesium sulfate. After the reaction solution was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and 3-ethylsulfanyl-N-methyl-N- (5-trifluoromethylpyridin-2-yl) -4-pyridinecarboxamide (Compound No .: A-6) was obtained in an amount of 0.32 g (oil).

Example 3
Synthesis of 3-ethylsulfonyl-N-methyl-N- (5-trifluoromethylpyridin-2-yl) -4-pyridinecarboxamide (Compound No .: A-8)
To a solution of 3-ethylsulfanyl-N-methyl-N- (5-trifluoromethylpyridin-2-yl) -4-pyridinecarboxamide (0.22 g) in methylene chloride (3 ml) was added m-chloroperbenzoic acid (purity of about 70 %: 0.35 g) was added at room temperature. The reaction was stirred at room temperature for 30 minutes. Water, sodium sulfite and potassium carbonate were added to the reaction solution and stirred. After separating the organic layer, the organic layer was further washed with water. The organic layer was dried over anhydrous magnesium sulfate, and then the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and 0.24 g of 3-ethylsulfonyl-N-methyl-N- (5-trifluoromethylpyridin-2-yl) -4-pyridinecarboxamide (Compound No .: A-8) ( oil)).
Example 4
3-ethylsulfonyl-N-ethyl-N- (5-trifluoromethanesulfonylpyridin-2-yl) -4-pyridinecarboxamide (compound number: A-155) and 3-ethylsulfonyl-N-ethyl-N- (5 -Trifluoromethanesulfinylpyridin-2-yl) -4-pyridinecarboxamide (Compound No .: A-156)
To a solution of 3-ethylsulfonyl-N-ethyl-N- (5-trifluoromethylthiopyridin-2-yl) -4-pyridinecarboxamide (0.70 g) in acetonitrile (7 ml) was added sodium tungsten (IV) dihydrate ( 30 mg) was added at room temperature. 35% aqueous hydrogen peroxide (14 ml) was added to the reaction mixture at room temperature, and the mixture was stirred at 65 ° C. for 3 hr. Ethyl acetate, water and sodium sulfite were added to the reaction mixture and stirred. After separating the organic layer, the organic layer was further washed with water. The organic layer was dried over anhydrous magnesium sulfate, and then the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and 0.47 g of 3-ethylsulfonyl-N-ethyl-N- (5-trifluoromethanesulfonylpyridin-2-yl) -4-pyridinecarboxamide (Compound No .: A-155) ( oil) and 3-ethylsulfonyl-N-ethyl-N- (5-trifluoromethanesulfinylpyridin-2-yl) -4-pyridinecarboxamide (Compound No .: A-156) in an amount of 45 mg (oil).

The ¹ H-NMR data of the compounds produced in the same manner as in the above Examples are shown in Tables 3-1 to 3-5 and 4 below.

Table 3-1.

Table 3-2

Table 3-3

Table 3-4

Table 3-5

Table 4

  The formulation containing the compound of the present invention will be specifically described below by giving some formulation examples. Of course, the compound of the present invention, auxiliary components and the amount of addition thereof are limited to the following formulation examples. is not. In the formulation examples, “part” means all parts by mass.

Formulation Example 1 : Emulsion Compound of the present invention (10 parts), xylene (60 parts), N-methyl-2-pyrrolidone (20 parts) and Solpol 3005X (mixture of nonionic surfactant and anionic surfactant, Toho Chemical Industry Co., Ltd. (trade name) (10 parts) was uniformly mixed and dissolved to obtain an emulsion.

Formulation example 2 : wettable powder-1
Compound of the present invention (20 parts), Nipseal NS-K (white carbon, Tosoh Silica Co., Ltd., trade name) (10 parts), Kaolin clay (Kaolinite, Takehara Chemical Co., Ltd., trade name) (60 parts) Sun extract P-252 (sodium lignin sulfonate, Nippon Paper Chemicals Co., Ltd., trade name) (5 parts) and Lunox P-65L (alkyl allyl sulfonate, Toho Chemical Co., Ltd., trade name) (5 parts) Was uniformly mixed and ground with an air mill to obtain a wettable powder.

Formulation Example 3 : wettable powder-2
Compound of the present invention (20 parts), Nipsil NS-K (white carbon, Tosoh Silica Co., Ltd., trade name) (20 parts), Kaolin clay (50 parts), LUNOX 1000C (naphthalene sulfonate condensate, Toho Chemical) Kogyo Co., Ltd. (trade name) (5 parts) and Solpol 5276 (nonionic surfactant, Toho Chemical Co., Ltd., trade name) (5 parts) were uniformly mixed and pulverized in an air mill to obtain a wettable powder. Obtained.

Formulation Example 4 : Aqueous Solvent-1
Compound (20 parts) of the present invention, Lunox P-65L (alkyl allyl sulfonate, Toho Chemical Industry Co., Ltd., trade name) (3 parts), water-soluble carrier (potassium chloride) (77 parts) are uniformly mixed and pulverized Thus, an aqueous solvent was obtained.

Formulation Example 5 : Aqueous solvent-2
Uniformly mix the compound of the present invention (50 parts), New Carden BX-C (Na alkylene phthalene sulfonate, Takemoto Yushi, trade name) (5 parts), silicon dioxide (2 parts) and water-soluble carrier (43 parts) The mixture was pulverized to obtain an aqueous solvent.

Formulation Example 6 : Flowable Agent-1
Premixed propylene glycol (5 parts), Solpol 7933 (anionic surfactant, Toho Chemical Co., Ltd., trade name) (5 parts) and water (50 parts) to the compound of the present invention (20 parts) ) Was dispersed into a slurry mixture, and this slurry mixture was wet pulverized with Dynomill (Shinmaru Enterprises Co., Ltd.), and then xanthan gum (0.2 parts) was mixed and dispersed well in water (19.8 parts) in advance. Things were added to obtain a flowable agent.

Formulation Example 7 : Flowable agent-2
Compound of the present invention (20 parts), Newkalgen FS-26 (mixture of dioctyl sulfosuccinate and polyoxyethylene tristyryl phenyl ether, Takemoto Yushi Co., Ltd., trade name) (5 parts), propylene glycol (8 parts) and Water (50 parts) was mixed in advance, and this slurry-like mixture was wet-pulverized with a Dynomill (Shinmaru Enterprises). Next, xanthan gum (0.2 parts) was thoroughly mixed and dispersed in water (16.8 parts) to prepare a gel-like material, which was thoroughly mixed with the pulverized slurry to obtain a flowable agent.

Formulation Example 8 : Emulsion formulation-1
Mixing and homogenizing the compound of the present invention (20 parts) with Solpol CA-42 (nonionic activator, Toho Chemical Co., Ltd., trade name) (15 parts) and preservative Proxel GX-L (0.1 parts) Then, water (59.6 parts) was gradually added with stirring to obtain a dispersion. Anti-foaming agent Antihome E-20 (emulsion-type modified silicone, Kao Corporation, trade name) (0.1 part) was added to the resulting dispersion, and xanthan gum dispersed in propylene glycol (5.0 parts) (0.2 parts) was added to obtain an emulsion formulation (phase inversion emulsification method).

Formulation Example 9 : Emulsion formulation-2
The compound of the present invention (10 parts) was dissolved in xylene (10 parts) and mixed with the surfactant Rheidol 430V (polyoxyethylene sorbite tetraoleate, Kao Corporation, trade name) (24 parts). In water (50.6 parts), the resulting liquid, antifoam anti-home E-20 (emulsion-type modified silicone, Kao Corporation, trade name) (0.1 part) and preservative Proxel GX-L ( 0.1 part) was added and dispersed using a homogenizer, and xanthan gum (0.2 part) dispersed in propylene glycol (5.0 parts) was added to obtain an emulsion formulation (mechanical emulsification method) .

Formulation Example 10 Microemulsion Agent-1
The compound of the present invention (0.01 part) and Solpol CA-42 (nonionic activator, Toho Chemical Co., Ltd., trade name) (0.1 part) were mixed and homogenized, and then gradually mixed with stirring. (99.79 parts) was added. Preservative Proxel GX-L (0.1 part) was added to the dispersion to obtain a microemulsion.

Formulation Example 11 : ME agent-2
The compound of the present invention (10 parts) and New Calgen D-945 (polyoxyethylene (20 mol) sorbitan monooleate, Takemoto Yushi Co., Ltd., trade name) (20 parts) were mixed and homogenized, and then stirred. Gradually water (69.9 parts) was added. Preservative Proxel GX-L (0.1 part) was added to the dispersion to obtain a microemulsion.

Formulation Example 12 : ME agent-3
The compound of the present invention (0.01 part) was mixed with solvent Solvesso 200 (0.08 part), Neukalgen ST-30 (polyoxyethylene arylphenyl ether formaldehyde condensate, polyoxyalkylene arylphenyl ether, alkylbenzene sulfonate, and xylene. In the mixture, Takemoto Yushi Co., Ltd., trade name) (0.12 parts), the mixture was mixed with a surfactant, homogenized, and water (99.69 parts) was gradually added while stirring. Preservative Proxel GX-L (0.1 part) was added to the dispersion to obtain a microemulsion.

Formulation Example 13 : Granule-1
The compound of the present invention (5 parts), bentonite (30 parts), clay (60 parts) and sodium lignin sulfonate (5 parts) were uniformly pulverized and mixed, mixed well with water, extruded and granulated, Granules were obtained by dry sizing.

Formulation Example 14 : Granule-2
After putting silica sand (90 parts) in a rolling granulator and containing water, the compound of the present invention (5 parts), sodium lignin sulfonate (4 parts), polyvinyl alcohol (PVA) (PVA) ( 0.5 parts) and white carbon (0.5 parts) were added and coated, and then dried and sized to obtain granules.

Formulation Example 15 : Granule-3
Ishikawa Light (89 parts) was placed in a rolling granulator and water-containing, and then the compound of the present invention (5 parts), sodium lignin sulfonate (3 parts), and dioctyl sulfosuccinate sodium previously pulverized and mixed. (0.5 parts), POE styryl phenyl ether (2 parts) and polyvinyl alcohol (PVA) (0.5 parts) were added, coated, and then dried to obtain granules.

Formulation Example 16 : Fine granule-1
The compound of the present invention (2 parts) was diluted with a solvent, and mixed with pumice (98 parts) as an extender while spraying the diluent. The obtained granular composition was dried and sieved to obtain a fine granule.

Formulation Example 17 : Fine granule-2
The compound of the present invention (5 parts) was subjected to air mill grinding or mechanochemical grinding as required. The powdery base and silica sand (85 parts) as an extender were uniformly mixed, and then mixed with spraying the binder Toxanone GR-31A (10 parts) diluted with a solvent, and the resulting granular composition was dried. Thereafter, it was sieved to obtain a fine granule.

Formulation Example 18 : Powder A compound of the present invention (5 parts), white carbon (5 parts), and clay (trade name, Nippon Talc Co., Ltd.) (90 parts) were uniformly mixed and ground to obtain a powder.

Formulation Example 19 : DL powder A compound (5 parts) of the present invention, propylene glycol (0.5 part) and DL clay (94.5 parts) were uniformly mixed and ground to obtain a powder.

Formulation Example 20 : Seed coating powder Compound (10 parts) of the present invention, sodium lignin sulfonate (6 parts), polyvinyl alcohol (PVA) (1 part) and clay (Nippon Talc Co., Ltd. trade name) (83 parts) A powder prepared by uniformly mixing and pulverizing was mixed with seeds previously wetted, and air-dried to obtain coated seeds.

Example 4
Next, the action effect and usefulness of the compound of the present invention will be described with specific test results. The compound used for comparison (Comparative Example A) was described in Example 17 of JP-A-5-32631 and was a compound having the following structure.

Test Example 1: Insecticidal effect test by spraying treatment on cucumber cotton aphid (Aphis gosiipii Glover) A leaf piece infested with 50 to 80 aphid adult larvae was inoculated into the leaves of pot-planted cucumber seedlings grown for 2 weeks after sowing. . On the day after the inoculation, the chemical solution adjusted to 500 ppm was sprayed onto the leaf stems of cucumber seedlings infested with aphids using an air brush. Seven days after the treatment, the number of parasitic aphids was examined, and the control rate was calculated according to the following formula. The test was conducted using 1 seedling in each group.

Control rate (%) = (1−A / B × D / C) × 100
A: Number of aphid adult larvae before spraying in the untreated area per seedling B: Number of adult aphids before spraying in the treated area per seedling C: Number of adult aphids 7 days after spraying in the untreated area per seedling D: Per seedling Aphid adult larvae 7 days after spraying in the treatment area

  As a result, compound numbers A-2, A-5, A-6, A-8, A-9, A-11, A-13, A14, A-20, A-23, A- 26, A-27, A-28, A-34, A-36, A-37, A-39, A-40, A-44, A-45, A-46, A-47, A-48, A-49, A-52, A-53, A-54, A-56, A-57, A-65, A-68, A-69, A-70, A-71, A-72, A- 74, A-75, A-76, A-77, A-120, A-136, A-137, A-138, A-139, A-140, A-141, A-143, A-148, A-151, A-152, A-153, A-154, A-155, A-156, A-157, A-158, A-159, A-171, A-172, A-173, A- Each of 174, A175, A-176, A-184, A-185 and A-186 compounds showed a control rate of 90% or more. On the other hand, the control rate of the compound of Comparative Agent A was 0%.

Test Example 2: Insecticidal effect test by irrigation treatment on cucumber cotton aphid (Aphis gosiipii Glover) Inoculated 50 to 80 leaves of aphid adult larvae onto the leaves of potted cucumber seedlings grown for 2 weeks after sowing . On the day after the inoculation, the chemical solution prepared to 500 ppm was irrigated to the stock of the cucumber seedlings infested with aphids. Seven days after the treatment, the number of parasitic aphids was examined, and the control rate was calculated according to the following formula. The test was conducted using 1 seedling in each group.

Control rate (%) = (1−A / B × D / C) × 100
A: Number of aphid adult larvae before spraying in the untreated area per seedling B: Number of adult aphids before spraying in the treated area per seedling C: Number of adult aphids 7 days after spraying in the untreated area per seedling D: Per seedling Aphid adult larvae 7 days after spraying in the treatment area

  As a result, the compound numbers A-1, A-2, A-4, A-5, A-6, A-8, A-9, A-11, A-12, A-13, corresponding to the present invention, A-14, A-17, A-18, A-20, A-23, A-26, A-27, A-28, A-30, A-32, A-35, A-36, A- 37, A-39, A-40, A-44, A-45, A-46, A-47, A-48, A-49, A-52, A-53, A-54, A-55, A-56, A-57, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-75, A-76, A- 77, A-92, A-93, A-136, A-137, A-138, A-139, A-140, A-141, A-143, A-147, A-148, A-149, A-151, A-152, A-153, A-154, A-155, A-156, A-157, A-158, A-159, A-160, A-161, A-162, A- 164, A-165, A-166, A-167, A-168, A-169, A-171, A-172, A-173, A-174, A-175, A-176, A-178, Each of the compounds A-179, A-180, A-181, A-184, A-185 and A-186 showed a control rate of 90% or more. On the other hand, the control rate of the compound of Comparative Agent A was 0%.

Test Example 3: Test of egg-killing effect on beetle tobacco whitefly (Bemisia tabaci Gennadius) The seedling seedlings in the initial leaf stage of seedlings grown for about one month after sowing were placed in a greenhouse where tobacco whitefly was generated, Spawned. A leaf disk was made from the spawned primary bean leaves and placed on a damp cotton wool so that the leaf back (spawning surface) was on top. The chemical solution prepared to a predetermined concentration was sprayed on the leaf disk using an air brush. After spraying, it is kept in a constant temperature room at 25 ° C., and on the 7th to 12th day after the treatment, the state of hatched larvae is classified into 4 grades, that is, 100 (larvae mortality: 100%), 80 (same: 99-80%) ), 50 (same: 79-50%), 0 (same: less than 50%). Based on the evaluation, the larva control value was calculated by the following formula. The test was conducted using 3 discs in each section.

Larval control value (%) = (A × 100 + B × 80 + C × 50) / (A + B + C + D)
A: Number of grade 100 disks B: Number of grade 80 disks C: Number of grade 50 disks D: Number of grade 0 disks

  As a result, the compound numbers A-3, A-26, A-27, A-28, A-36, A-37, A-39, A-40, A-46, A-52, corresponding to the present invention, A-53, A-54, A-56, A-57, A-71, A-72, A-75, A-76, A-77, A-79, A-81, A-149, A- Each of the 152, A-153, A-154, A-155, A-156, A-175, A-178, A-180 and A-185 compounds showed a control rate of 90% or more. On the other hand, the control rate of the compound of Comparative Agent A was 0%.

  The present invention can be used in the field of agriculture and horticulture.

Claims (6)

Formula (1)

[Where
R ¹ represents a C _1-6 alkyl group or a C _1-6 haloalkyl group,
R ² represents a hydrogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
G ¹ , G ² , G ³ , G ⁴ and G ⁵ each independently represent a nitrogen atom or CR ³ (provided that G ¹ , G ² , G ³ , G ⁴ and G ⁵ are simultaneously nitrogen atoms And at least one of G ¹ , G ² , G ³ , G ⁴ and G ⁵ is CR ³ ),
R ³ may be the same or different and is a hydrogen atom, a halogen atom, a C _1-12 alkyl group, a C _1-12 haloalkyl group, a C _3-8 cycloalkyl group, a C _1-6 alkoxy group, a C _3-6 Alkenyloxy group, C _3-6 alkynyloxy group, C _1-6 haloalkoxy group, C _3-6 haloalkenyloxy group, C _3-6 haloalkynyloxy group, C _1-6 alkylthio group, C _1-6 alkyl sulfinyl group, C _1-6 alkylsulfonyl group, C _1-6 haloalkylthio group, C _1-6 haloalkylsulfinyl group, C _1-6 haloalkylsulfonyl group, a nitro group, a cyano group, four R ⁴ from SF5,1 A phenyl group which may be substituted with, or a phenoxy group which may be substituted with 1 to 4 R ⁵ , or
When two R ³ constitute a ring containing G ^{1 to} G ⁵ and are bonded to each of two adjacent carbon atoms, the two R ³ are bonded to each other, and Together with the ring carbon atoms may form a saturated or unsaturated 5- or 6-membered ring,
R ⁴ and R ⁵ are each independently a halogen atom, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy show group, C _1-6 alkylthio group, C _1-6 alkylsulfinyl group, C _1-4 alkylsulfonyl group, C _1-6 haloalkylthio group, a C _1-6 haloalkylsulfinyl group or a C _1-6 haloalkylsulfonyl group ,
X may be the same or different, and may be 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. Indicate
n represents an integer from 0 to 2,
m represents an integer of 0 to 3. ]
A 4-pyridinecarboxamide derivative represented by the formula: N-oxide or a salt thereof. The 4-pyridinecarboxamide derivative, its N-oxide or a salt thereof according to claim 1, wherein R ¹ represents a C _1-6 alkyl group. The 4-pyridinecarboxamide derivative, its N-oxide or a salt thereof according to claim 1 or 2, wherein R ² represents a hydrogen atom or a C _1-6 alkyl group.   The 4-pyridinecarboxamide derivative, its N-oxide or a salt thereof according to any one of claims 1 to 3, wherein m represents 0.   An agricultural and horticultural agent containing the 4-pyridinecarboxamide derivative according to any one of claims 1 to 4, its N-oxide or a salt thereof.   The agricultural and horticultural agent according to claim 5, which is an agricultural and horticultural insecticide.