KR101350027B1 - 3-aminoxalylaminobenzamide derivatives, and insecticidal and miticidal agents containing same as active ingredient - Google Patents

Abstract

(식 중, R¹ 및 R²는, 예를 들면, C₁∼C₃ 알콕시기나, C₁∼C₃ 할로알콕시기, R³ 및 R⁴는, 예를 들면, C₁∼C₈ 알킬기나, C₁∼C₈ 할로알킬기, R⁵는, C₁∼C₅ 할로알킬기, R⁶ 및 R⁷는, 예를 들면, 수소 원자나, C₁∼C₅ 알킬기, Y는, 예를 들면, 수소 원자나, 할로겐 원자, Z는, 예를 들면, 수소 원자 등을 나타낸다. n은, 0∼4의 정수를 나타낸다. m은, 0∼2의 정수를 나타낸다.)Provided are 3-aminooxalylaminobenzamide derivatives for use in pesticides, acaricides.
The 3-aminooxalylaminobenzamide derivative is represented by the following formula.

(Wherein, R ¹ and R ² are, for example, C ₁ ~C ₃ alkoxyl group or, C ₁ ~C ₃ haloalkoxy group, R ³ and R ⁴ are, for example, C ₁ ~C ₈ alkyl group or , A C ₁ -C ₈ haloalkyl group, R ⁵ is a C ₁ -C ₅ haloalkyl group, R ⁶ and R ⁷ are, for example, a hydrogen atom, a C ₁ -C ₅ alkyl group, Y is, for example, A hydrogen atom, a halogen atom, Z represents, for example, a hydrogen atom, etc. n represents an integer of 0 to 4. m represents an integer of 0 to 2)

Description

3-aminooxalylaminobenzamide derivatives and pesticides and acaricides having the active ingredient {3-AMINOXALYLAMINOBENZAMIDE DERIVATIVES, AND INSECTICIDAL AND MITICIDAL AGENTS CONTAINING SAME AS ACTIVE INGREDIENT}

The present invention relates to novel 3-aminooxalylaminobenzamide derivatives and insecticides and acaricides containing these as active ingredients.

It is already known that 3-acylamino benzamides etc. are useful as a pesticide (for example, patent documents 1-24).

It is also known that 3-acylaminobenzamides represented by the following Compounds A and B are useful as insecticides (for example, Patent Document 25).

However, in the compound disclosed in Patent Document 25, the 3-acylamino moiety has an alkoxyoxarylamino structure, and the compound having an aminooxarylamino structure is not particularly disclosed.

WO2005-021488 publication WO2005-707165 Publication WO2006-137376 publication WO2006-137395 publication Japanese Patent Laid-Open No. 2006-225340 WO2007-013150 publication WO2007-013332 publication WO2007-017075 publication Japanese Patent Application Laid-Open No. 2007-099761 WO2007-128410 publication Japanese Unexamined Patent Publication No. 2007-119416 Japanese Patent Laid-Open No. 2007-302617 WO2008-000438 publication WO2008-012027 publication WO2008-074427 publication WO2008-075453 Publication WO2008-075454 publication WO2008-075459 publication WO2008-075465 publication WO2008-107091 publication WO2009-09844 publication WO2009-09845 publication WO2009-080203 Publication Japanese Unexamined Patent Publication No. 2009-209090 Japanese Unexamined Patent Publication No. 2006-306771

An object of the present invention is to provide a compound having an aminooxarylyl structure, which exhibits a high effect against various pests and ticks.

MEANS TO SOLVE THE PROBLEM As a result of earnest effort in order to solve the said subject, the present inventors discovered that the compound which has the aminooxarylyl structure represented by a following formula is a useful compound which has the said characteristic, and came to complete this invention. That is, this invention is the following formula [1],

(Wherein, R ¹ and R ² are each independently hydrogen atom, C ₁ ~C ₃ alkoxy group, C ₁ ~C ₃ haloalkoxy group, a halogen atom, C ₁ ~C ₅ alkyl group.

R ³ and R ⁴ are each independently a hydrogen atom, a C ₁ -C ₈ alkyl group, a C ₁ -C ₈ haloalkyl group, an allyl group, a C ₃ -C ₈ cycloalkyl group, a C ₃ -C ₆ cycloalkyl C ₁ -C ₄ represents an alkyl group. However, R ³ and R ⁴ may be bonded to each other to form a C ₃ to C ₆ alkylene bond, R ⁵ represents a C _{1 to} C ₅ haloalkyl group, and R ⁶ and R ⁷ are each independently hydrogen. atom, C ₁ ~C ₅ alkyl group, C ₃ ~C ₈ cycloalkyl group, C ₁ ~C ₅ haloalkyl group, C ₁ ~C ₃ alkoxy C ₁ ~C ₄ alkyl group, C ₂ ~C ₆ alkenyl, C ₂ ~C ₆ haloalkenyl group, C _{1 to} C ₄ alkylcarbonyl group, C _{1 to} C ₄ haloalkylcarbonyl group, C _{1 to} C ₄ alkylsulfonyl group, C _{1 to} C ₄ haloalkylsulfonyl group, C _{1 to} C ₃ alkoxycarbonyl group or C _{1-C 3} haloalkoxycarbonyl group is represented,

Y each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C ₁ -C ₅ alkyl group, a C ₁ -C ₅ haloalkyl group, a C ₁ -C ₃ alkylamino group, a diC ₁ -C ₃ alkylamino group, C ₁ -C ₃ alkoxy group or C ₁ -C ₃ haloalkoxy group,

Z is independently a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C ₁ -C ₅ alkyl group, a C ₁ -C ₅ haloalkyl group, a C ₁ -C ₃ alkoxy group or a C ₁ -C ₃ Represents a haloalkoxy group,

n represents the integer of 0-4, m represents the integer of 0-2.)

3-aminooxalylaminobenzamide derivatives (hereinafter, simply referred to as 'compounds of the present invention'), and insecticides and acaricides containing the derivatives as active ingredients (hereinafter, simply referred to as 'insecticides and acaricides of the present invention'). Is).

The compound of the present invention shows excellent effects against pests and ticks.

Hereinafter, the present invention will be described in detail.

In the formula ^[1], R 1 and R ² are each independently hydrogen atom, C ₁ ~C ₃ alkoxy group, C ₁ ~C ₃ haloalkoxy group, a halogen atom or a C ₁ ~C ₅ alkyl group. Here, C ₁ ~C ₃ alkoxy group, may optionally have a branch, C ₁ ~C ₃ alkoxy group is, for example, a methoxy group or an ethoxy group, isopropyl-oxy group and the like can be suitably enumerated. The C ₁ -C ₃ haloalkoxy group may have a branch, and as the C ₁ -C ₃ haloalkoxy group, for example, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, or the like is suitably used. Can be enumerated. As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom can be mentioned suitably, for example. As the C ₁ ~C ₅ alkyl group, may be straight-chain, and the alkyl group may have a branch, for example, a methyl group or an ethyl group, n- propyl, isopropyl, n- butyl, isobutyl, s- butyl Group, t-butyl group, n-pentyl group, isopentyl group, 2-pentyl group, 3-pentyl group, neopentyl group, t-pentyl group, etc. can be mentioned suitably. Especially as R <^1> , a methyl group, an ethyl group, isopropyl group, a methoxy group, and a trifluoro methoxy group are preferable. As R ² , a hydrogen atom, a methyl group, an ethyl group, a chlorine atom, a bromine atom, and an iodine atom are preferable.

R ³ and R ⁴ each independently represent a hydrogen atom, a C ₁ -C ₈ alkyl group, a C ₁ -C ₈ haloalkyl group, an allyl group, a C ₃ -C ₈ cycloalkyl group, or a C ₃ -C ₆ cycloalkyl C ₁ It represents a ~C ₄ alkyl group.

Here, as the C ₁ ~C ₈ alkyl group, may be straight-chain, and the alkyl group may have a branch, for example, a methyl group or an ethyl group, n- propyl group, isopropyl group, n- butyl group, isobutyl group, s -Butyl group, t-butyl group, n-pentyl group, isopentyl group, 2-pentyl group, 3-pentyl group, neopentyl group, t-pentyl group, n-hexyl group, t-octyl group, n-jade Tyl groups etc. can be enumerated suitably. As the C ₁ ~C ₈ alkyl group, preferably a C ₁ ~C ₆ alkyl group.

As the C ₁ ~C ₆ alkyl group, may be straight-chain, and the alkyl group may have a branch, for example, a methyl group or an ethyl group, n- propyl, isopropyl, n- butyl, isobutyl, s- butyl Group, t-butyl group, n-pentyl group, isopentyl group, 2-pentyl group, 3-pentyl group, neopentyl group, t-pentyl group, n-hexyl group, etc. can be mentioned suitably.

C ₁ ~C ₈ alkyl group is halo, may be straight chain, it may have a branch, and good haloalkyl group, e.g., a mono-fluoro or methyl, difluoro methyl, trifluoro methyl group, a mono-chloro group, dichloro-methyl, trichloro methyl group, Monobromomethyl group, dibromomethyl group, tribromomethyl group, 1-fluoroethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2 -Difluoroethyl group, 1-chloroethyl group, 2-chloroethyl group, 2,2-dichloroethyl group, 2,2,2-trichloroethyl group, 1-bromoethyl group, 2-bromoethyl group, 2,2-di Bromoethyl group, 2,2,2-tribromoethyl group, 2-iodethyl group, pentafluoroethyl group, 2-chloro-1,1,2,2-tetrafluoroethyl group, 2-bromo-1,1,2 , 2-tetrafluoroethyl group, 2-iodine-1,1,2,2-tetrafluoroethyl group, 3-fluoropropyl group, 3-chloropropyl group, 3-bromoprop Group, a 1,3-difluoro-2-propyl, 3,3-difluoro-propyl, 3,3,3-trifluoro propyl group,

3,3,3-trichloropropyl group, 1,3-dichloro-2-propyl group, 1,1,1-trifluoro-2-propyl group, 1-chloro-3-fluoro-2-propyl group, 1 , 1,1,3,3,3-hexafluoro-2-propyl group, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl group, 2-bromo-1, 1,1,3,3,3-hexafluoro-2-propyl group, 2,2,3,3,3-pentafluoropropyl group, heptafluoroisopropyl group, heptafluoro-n-propyl group, 1-chloro -1,1,2,3,3,3-hexafluoro-2-propyl group, 1-bromo-1,1,2,3,3,3-hexafluoro-2-propyl group, 2-chloro- 1,1,2,3,3,3-hexafluoro-n-propyl group, 2-bromo-1,1,2,3,3,3-hexafluoro-n-propyl group, 4-fluorobutyl group , 4,4,4-trifluorobutyl group, nonafluoro-n-butyl group, nonafluoro-2-butyl group, 4,4,5,5,5-pentafluoropentyl group, 3,3,4,4 , 5,5,5-heptafluoropentyl group, undecafluoro-2-pentyl group, undecafluoro-3-pentyl group, undecafluoro-n-pentyl group, 6,6,6-triflu Reuhek can be suitably enumerated a group, 1H, 1H- cyclopenta deca fluorine octyl group and the like. As the C ₁ ~C ₈ haloalkyl group, it may be fit in the C ₁ ~C ₆ haloalkyl group.

C _1- C ₆ The haloalkyl group is a linear or haloalkyl group which may have a branch, for example, a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, Dibromomethyl group, tribromomethyl group, 1-fluoroethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 1-chloroethyl group, 2-chloroethyl group, 2,2-dichloroethyl group, 2,2,2-trichloroethyl group, 1-bromoethyl group, 2-bromoethyl group, 2,2-dibromoethyl group, 2, 2,2-tribromoethyl group, 2-iodine ethyl group, pentafluoroethyl group, 2-chloro-1,1,2,2-tetrafluoroethyl group, 2-bromo-1,1,2,2-tetrafluoro Ethyl group, 2-iodine-1,1,2,2-tetrafluoroethyl group, 3-fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, 1,3-difluoro-2-propyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group,

3,3,3-trichloropropyl group, 1,3-dichloro-2-propyl group, 1,1,1-trifluoro-2-propyl group, 1-chloro-3-fluoro-2-propyl group, 1 , 1,1,3,3,3-hexafluoro-2-propyl group, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl group, 2-bromo-1, 1,1,3,3,3-hexafluoro-2-propyl group, 2,2,3,3,3-pentafluoropropyl group, heptafluoroisopropyl group, heptafluoro-n-propyl group, 1-chloro -1,1,2,3,3,3-hexafluoro-2-propyl group, 1-bromo-1,1,2,3,3,3-hexafluoro-2-propyl group, 2-chloro- 1,1,2,3,3,3-hexafluoro-n-propyl group, 2-bromo-1,1,2,3,3,3-hexafluoro-n-propyl group, 4-fluorobutyl group , 4,4,4-trifluorobutyl group, nonafluoro-n-butyl group, nonafluoro-2-butyl group, 4,4,5,5,5-pentafluoropentyl group, 3,3,4,4 , 5,5,5-heptafluoropentyl group, undecafluoro-2-pentyl group, undecafluoro-3-pentyl group, undecafluoro-n-pentyl group, 6,6,6-triflu Reuhek can be suitably enumerated a group or the like.

As the C ₃ ~C ₈ cycloalkyl, may optionally have a branch, for the example, a cyclopropyl group or 1-methylcyclopropyl group, a 2-methylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. It may enumerate suitably. As the C ₃ ~C ₈ cycloalkyl group, it may be fit in the C ₃ ~C ₆ cycloalkyl group.

As the C ₃ ~C ₆ cycloalkyl, C ₁ ~C ₄ alkyl group, may optionally have a branch, for example, a cyclopropyl group or a 1-cyclopropyl group, cyclobutyl group and the like can be suitably enumerated.

R ³ and R ⁴ may be bonded to each other to form a C ₃ to C ₈ alkylene bond, and as the C _{3 to} C ₈ alkylene bond, for example, (CH ₂ ) ₃ or (CH ₂ ) ₄ , (CH ₂ ) ₅ , (CH ₂ ) ₆ and the like can be enumerated as appropriate. As the C ₃ ~C ₈ alkylene bond, C ₃ ~C ₆ may be fit in the alkylene linkage.

Especially as R <^3> , a methyl group and an ethyl group are preferable. As R ⁴ , a methyl group, an ethyl group, n-propyl group, isopropyl group, cyclopropyl group, t-butyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group desirable.

R ⁵ is C _{1 to} C ₅ A haloalkyl group is shown.

Where C _{1 to} C ₅ The haloalkyl group is a linear or haloalkyl group which may have a branch, for example, a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, Dibromomethyl group, tribromomethyl group, 1-fluoroethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 1-chloroethyl group, 2-chloroethyl group, 2,2-dichloroethyl group, 2,2,2-trichloroethyl group, 1-bromoethyl group, 2-bromoethyl group, 2,2-dibromoethyl group, 2, 2,2-tribromoethyl group, 2-iodine ethyl group, pentafluoroethyl group, 2-chloro-1,1,2,2-tetrafluoroethyl group, 2-bromo-1,1,2,2-tetrafluoro Ethyl group, 2-iodine-1,1,2,2-tetrafluoroethyl group, 3-fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, 1,3-difluoro-2-propyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, 3,3,3-trichloropropyl group, 1,3-dichloro-2 -Propyl group, 1,1,1-trifluoro-2-propyl group, 1-chloro-3-fluoro-2-propyl group, 1,1,1,3,3,3-hexafluoro-2-propyl group , 1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl group,

2-bromo-1,1,1,3,3,3-hexafluoro-2-propyl group, 2,2,3,3,3-pentafluoropropyl group, heptafluoroisopropyl group, heptafluoro-n -Propyl group, 1-chloro-1,1,2,3,3,3-hexafluoro-2-propyl group, 1-bromo-1,1,2,3,3,3-hexafluoro-2- Propyl group, 2-chloro-1,1,2,3,3,3-hexafluoro-n-propyl group, 2-bromo-1,1,2,3,3,3-hexafluoro-n-propyl Group, 4-fluorobutyl group, 4,4,4-trifluorobutyl group, nonafluoro-n-butyl group, nonafluoro-2-butyl group, 4,4,5,5,5-pentafluoropentyl group, 3,3,4,4,5,5,5-heptafluoropentyl group, undecafluoro-2-pentyl group, undecafluoro-3-pentyl group, undecafluoro-n-pentyl group, etc. are listed suitably. can do.

R ⁶ and R ⁷ each independently represent a hydrogen atom, a C ₁ -C ₅ alkyl group, a C ₃ -C ₈ cycloalkyl group, a C ₁ -C ₅ haloalkyl group, a C ₁ -C ₃ alkoxy C ₁ -C ₄ alkyl group, C _2- C ₆ alkenyl group, C ₂ -C ₆ halo alkenyl group, C ₁ -C ₄ alkylcarbonyl group, C ₁ -C ₄ haloalkylcarbonyl group, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄ haloalkylsulfo group, C ₁ ~C ₃ represents the alkoxy group or a C ₁ ~C ₃ haloalkoxy group.

Here, C ₁ ~C ₅ alkyl group, C ₃ ~C ₈ cycloalkyl group and a C ₁ ~C ₅ The haloalkyl group is the same as the C _{1 to} C ₅ alkyl group, the C _{3 to} C ₈ cycloalkyl group, and the C _{1 to} C ₅ haloalkyl group described above.

As the C ₁ ~C ₃ alkoxy C ₁ ~C ₄ alkyl group, may be straight chain, a good alkyloxy group may have a branch, for example, methoxy adapted to ethoxymethyl group or ethoxymethyl group, 2-methoxyethyl group and the like in Can be enumerated. Examples of C ₂ ~C ₆ alkenyl group, may be a straight chain, branched, and have a good alkenyl group, e.g., vinyl group or allyl group, a 1-methyl-2-pro group, 2-methyl-2-pro group, 2-butenyl group, 3-butenyl group, etc. can be enumerated suitably.

C ₂ ~C ₆ haloalkenyl As a group, may be straight chain, a good halo-alkenyl group may have a branch, for example, 2-chloro-2-propenyl group, 3-chloro-2-propenyl group, 2-bromo -2-propenyl group, 3-bromo-2-propenyl group, 3,3-difluoro-2-propenyl group, 3,3-dichloro-2-propenyl group, 3,3-dibromo-2-prop A phenyl group, a 2, 3- dibromo-2- propenyl group, a 4, 4- difluoro-3- butenyl group, a 3, 4, 4- tribromo-3- butenyl group, etc. can be mentioned suitably.

As the C ₁ ~C ₄ alkyl group, may be straight chain, may be cyclic, branched and may have a good alkylcarbonyl group, e.g., an acetyl group or, a propionyl group, an isopropyl group, a cyclopropyl group, etc. can be suitably enumerated have.

As the C ₁ ~C ₄ haloalkyl group, it may be straight chain, branched and may have a good haloalkyl group, for example, trifluoromethyl group or an acetyl, penta fluoride propionyl group, an acetyl group trichloromethyl, chloroacetyl group, a bromo Acetyl group, 3-chloropropionyl group, etc. can be enumerated suitably.

As the C ₁ ~C ₄ alkylsulfonyl group, may be straight chain, may be cyclic, and good alkylsulfonyl group may have a branch, for example, a methylsulfonyl group or, ethyl sulfonyl group, n- propyl sulfonyl, isopropyl sulfonyl pireu And a nil group, cyclopropylsulfonyl group, n-butylsulfonyl group, isobutylsulfonyl group, s-butylsulfonyl group, t-butylsulfonyl group and the like.

C ₁ ~C ₄ haloalkyl As the alkylsulfonyl group, may be straight-chain, and even if good haloalkylsulfonyl group has a branch, for example, trifluoromethyl group or sulfonyl, penta-fluoro-ethyl sulfonyl group, 2,2,2- Fluoroethylsulfonyl group, heptafluoro-n-propylsulfonyl group, heptafluoroisopropylsulfonyl group, nonafluoro-nbutylsulfonyl group, nonafluoro-s-butylsulfonyl group and the like can be mentioned as appropriate.

As the C ₁ ~C ₃ alkoxycarbonyl group, it may be straight-chain, and the alkoxy group may have a branch, for example, a methoxycarbonyl group or an ethoxycarbonyl group, etc., isopropyloxy group can be suitably enumerated.

C ₁ ~C ₃ haloalkoxy group as the straight-chain may be, and good haloalkoxy group may have a branch, for example, chloromethoxy group, or a 2,2,2-trifluoro-ethoxy group, a 3, 3, 3-trifluoropropyloxycarbonyl group, 3,3,3-trichloropropyloxycarbonyl group, etc. can be mentioned suitably.

Especially as R <^6> , a hydrogen atom and a methyl group are preferable. As R <^7> , a hydrogen atom and a methyl group are preferable.

Y each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C ₁ -C ₅ alkyl group (preferably a C ₁ -C ₃ alkyl group), and a C ₁ -C ₅ haloalkyl group (preferably Advantageously, C ₁ ~C ₃ haloalkyl group), C ₁ ~C ₃ alkyl group, a di-C ₁ ~C ₃ alkyl group, C ₁ ~C ₃ alkoxyl group or a C ₁ ~C ₃ represents a haloalkoxy.

Here, as the C ₁ ~C ₃ alkyl group, it may be straight-chain, and the alkyl group may have a branch, for example, be a methyl group or an ethyl group, preferably an open n- propyl, isopropyl and the like.

As the C ₁ ~C ₃ haloalkyl group, it may be straight chain, a good haloalkyl group may have a branch, for example, a methyl group or the like-difluoro, trifluoro methyl group, an ethyl group penta fluoride can be suitably enumerated.

As the C ₁ ~C ₃ alkyl group, may be straight chain, may be cyclic, branched and may have a good alkylamino group, for example a methyl or amino group, ethylamino group, n- propyl group, isopropyl group, cyclopropyl group and the like It may enumerate suitably.

As the di-C ₁ ~C ₃ alkyl group, may be straight chain, may be cyclic, and good dialkylamino group may have a branch, for example, a dimethylamino group, a methyl ethylamino group, diethylamino group, di -n- propyl group, a di Isopropylamino group etc. can be enumerated suitably.

The definition of other groups is as defined above.

Especially as Y, a hydrogen atom and a halogen atom are preferable.

Z is independently a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C ₁ -C ₅ alkyl group (preferably a C ₁ -C ₃ alkyl group), a C ₁ -C ₅ haloalkyl group, C ₁ represents a ~C ₃ alkoxy group or a C ₁ ~C ₃ haloalkoxy.

The definition of the other group is as defined above.

Especially as Z, a hydrogen atom is preferable.

n represents the integer of 0-4.

m represents the integer of 0-2.

The compound of the present invention may contain a conformational isomer depending on the kind of the substituent, but the present invention includes a mixture containing the isomer in any proportion. In addition, although the optical isomer which exists in the compound of this invention resulting from the presence of an imbalanced carbon atom may exist, this invention includes the mixture containing all the optically active agents in arbitrary ratios.

The compound of this invention is a novel compound and can be manufactured according to the following synthetic schemes 1-3, for example.

Scheme 1

(In formula, R <^1> , R <^2> , R <^3> , R <^4> , R <^5> , R <^6> , R <^7> , n, m, Y, and Z are as defined by Formula [1], and R <^8> represents lower alkyl. The lower alkyl group is, for example, an alkyl group having about 1 to 5 carbon atoms.)

(1) Preparation of the compound of general formula [4]

Compound [4] can be obtained by making compound [2] react with compound [3]. This reaction can be performed in the presence or absence of a solvent and a base.

As a solvent, if it does not directly participate in this reaction, it will not specifically limit, For example, Aromatic hydrocarbons, such as benzene, toluene, xylene; Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; Halogenated hydrocarbons such as chloroform and methylene chloride; Esters such as methyl acetate and ethyl acetate; Ethers such as tetrahydrofuran, dioxane, diethyl ether and 1,2-dimethoxyethane; water; And polar solvents such as acetonitrile, N, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide or a mixed solvent of the above solvents.

Organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undeca-7-ene (DBU), and 4-dimethylaminopyridine; Alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; Alkaline earth metal hydroxides such as calcium hydroxide; Alkali metal carbonates such as sodium carbonate and potassium carbonate; Alkaline earth metal carbonates such as calcium carbonate; Alkali metal hydrogencarbonates such as sodium hydrogencarbonate; And metal alkoxides such as sodium methoxide and potassium ethoxide. The reaction temperature is, for example, -30 ° C to 150 ° C, preferably -5 ° C to 80 ° C. After the completion of the reaction, the target substance may be isolated from the reaction system by a conventional method, and the target substance can be produced by purifying with solvent, recrystallization, column chromatography, or the like as necessary. Moreover, it is also possible to provide to a next process, without isolating a target object from a reaction system.

Compound [2] is a well-known compound. The aniline derivative represented by the general formula [3], which is a raw material compound of the reaction, can be produced according to the production method disclosed in WO2005-021488 or WO2005-073165.

(2) Preparation of Compound of General Formula [1]

Compound [1] can be obtained by making compound [5] react with said compound [4]. This reaction can be performed in the presence or absence of a solvent and a base.

As a solvent, if it does not directly participate in this reaction, it will not specifically limit, For example, Aromatic hydrocarbons, such as benzene, toluene, xylene; Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; Halogenated hydrocarbons such as chloroform and methylene chloride; Esters such as methyl acetate and ethyl acetate; Ethers such as tetrahydrofuran, dioxane, diethyl ether and 1,2-dimethoxyethane; water; Polar solvents such as acetonitrile, N, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide; Alcohol, such as methanol, ethanol, isopropanol, or the mixed solvent of the said solvent is mentioned.

Examples of the base include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undeca-7-ene (DBU), and 4-dimethylaminopyridine; Alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; Alkaline earth metal hydroxides such as calcium hydroxide; Alkali metal carbonates such as sodium carbonate and potassium carbonate; alkaline earth metal carbonates such as calcium carbonate; Alkali metal hydrogencarbonates such as sodium hydrogencarbonate; And metal alkoxides such as sodium methoxide and potassium ethoxide. The reaction temperature is, for example, -30 ° C to 150 ° C, preferably -5 ° C to 80 ° C. After completion of the reaction, the target product may be isolated from the reaction system by a conventional method, and the target product can be produced by purifying with solvent, recrystallization, column chromatography, or the like as necessary.

Scheme 2

(In formula, R <^1> , R <^2> , R <^3> , R <^4> , R <^5> , R <^6> , R <^7> , n, m, Y, and Z are as having defined by Formula [1].)

The reaction of Scheme 2 can be carried out in the presence of a condensing agent, in the presence of a solvent and a base, or in the absence of. As a solvent, Aromatic hydrocarbons, such as benzene, toluene, and xylene; Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; Halogenated hydrocarbons such as chloroform and methylene chloride; water; Esters such as methyl acetate and ethyl acetate; Or ethers such as tetrahydrofuran, dioxane, diethyl ether and 1,2-dimethoxyethane; water; Polar solvents such as acetonitrile, N, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide; Alcohol, such as methanol, ethanol, isopropanol, or the mixed solvent of the said solvent is mentioned.

Examples of the base include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undeca-7-ene (DBU), and 4-dimethylaminopyridine; Alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; Alkaline earth metal hydroxides such as calcium hydroxide; Alkali metal carbonates such as sodium carbonate and potassium carbonate; Alkaline earth metal carbonates such as calcium carbonate; Alkali metal hydrogencarbonates such as sodium hydrogencarbonate; And metal alkoxides such as sodium methoxide and potassium ethoxide.

As a condensation agent used by reaction, 1, 3- dicyclohexyl carbodiimide (DCC), 2-chloro-1- methylpyridinium iodide, carbonyl diimidazole (CDI), anhydrous, for example. Trifluoroacetic acid, and the like. The reaction temperature is, for example, -30 ° C to 150 ° C, preferably -5 ° C to 80 ° C. After completion of the reaction, the target product may be isolated from the reaction system by a conventional method, and the target product can be produced by purifying with solvent, recrystallization, column chromatography, or the like as necessary.

Scheme 3

(In formula, R <^1> , R <^2> , R <^3> , R <^4> , R <^5> , R <^6> , R <^7> , n, m, Y, and Z are as defined by Formula [1], X represents a halogen atom. .)

Reaction of scheme 3 can be performed in the presence of a solvent and a base, or in absence of.

As a solvent, if it does not directly participate in this reaction, it will not specifically limit, For example, Aromatic hydrocarbons, such as benzene, toluene, xylene; Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; Halogenated hydrocarbons such as chloroform and methylene chloride; Esters such as methyl acetate and ethyl acetate; Or ethers such as tetrahydrofuran, dioxane, diethyl ether and 1,2-dimethoxyethane; water; And polar solvents such as acetonitrile, N, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide or a mixed solvent of the above solvents.

Examples of the base include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undeca-7-ene (DBU), and 4-dimethylaminopyridine; Alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; Alkaline earth metal hydroxides such as calcium hydroxide; Alkali metal carbonates such as sodium carbonate and potassium carbonate; Alkaline earth metal carbonates such as calcium carbonate; Alkali metal hydrogencarbonates such as sodium hydrogencarbonate; And metal alkoxides such as sodium methoxide and potassium ethoxide. The reaction temperature is, for example, -30 ° C to 150 ° C, preferably -5 ° C to 80 ° C. After completion | finish of reaction, a target object may be isolated from a reaction system by a conventional method, and the target object can be manufactured by refine | purifying by solvent washing, recrystallization, column chromatography, etc. as needed.

Insecticides and acaricides of the present invention containing the compound of the present invention represented by the formula [1] as an active ingredient can be used for the prevention and rescue of harmful organisms in scenes such as agriculture, indoors, forests, livestock and sanitation. Although the specific use scene, target marine organism, and usage method are shown below, the content of this invention is not limited to these.

The compounds of the present invention include crops such as edible crops (rice, barley, wheat, rye, oatmeal, wheat, corn, potatoes, sugar cane, taro, soybeans, soybeans, silkworm beans, peas, kidney beans, peanuts, etc.). Legumes), vegetables (cabbage, cabbage, radish, turnips, broccoli, cauliflower, rape crops such as Japanese mustard spinach (Brassica Rapa var. Pervidis), melons such as pumpkin, cucumber, watermelon, melon, melon, eggplant, Tomato, bell pepper, pepper, okura; Abelmoschus esculentus), spinach, lettuce, lotus root, carrot, burdock, garlic, onion, green onion, etc.), fruit and fruit (apple, citrus, pear, grape, peach, apricot, cherry, walnut, chestnut, almond, banana) , Strawberries, etc.), flavored crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), special crops (tobacco, tea, beets, sugar cane, hops, cotton, hemp, olives, rubber, coffee, etc.) , Grasses and fodder crops (timothy, clover, alfalfa, corn, sorghum, orchard grass, rice and grasses, legumes, etc.), grasses (gold grass, bentgrass, etc.), trees (firs) , Spruce, pine, hawthorn, cedar, cypress, etc. or arthropods that damage plants (such as chrysanthemums, roses, carnations, orchids, herbaceous plants, flowers, ginkgo, cherry trees, laurel, etc.) It can also be used to control marine organisms such as mollusks and nematodes.

As a specific marine species, the Lepidoptera of the arthropod moon insects, for example, Helicobpa armigera, Heliothis spp. ), Cabbage silver pattern moth (Trichoplusia ni), thief moth (Mamestra brassicae), moth (Spodoptera exigua), tobacco moth (Spodoptera litura), etc. Amoxophyes orana fasciata, Amoxophyes honmai, Amoxophyes honmai, Archips fuscocupreanus, Homona magnanima, Camellia moth, Caloptilia theivora Moths (Grapholita molesta), moths moths (Eumeta minuscula), oyster moths, apple oyster moths (Lyonetia prunifoliella malinella), oyster moths (Lyonetia clerkella) Gyulgul Citrus moth (Phyllocnistis citrella), such as apple moth oysters and fine moth (Phyllonorycter ringoniella), etc.

Pectinophora gossypiella, etc. , Moths such as Carposina niponensis, Codling moths, Yellow-winged moths (Monema flavecens), Parasa lepida, Black-tailed moths (Scopelodes contracus) Chilo suppressalis, Yellow Scirpophaga incertulas, Blackmoth moth (Cnaphalocrocis medinalis), Chinese cabbage moth (Hellulla undalis), Peach moth (Conogethes punctiferlis), Moth monk moth (Diaphania indica) (Parapediasia teterrella), the scorpion butterfly (Parnara guttata), the swallowtail butterfly (Papilio xuthus), the white-tailed butterfly (Pieris rapae crucivora), etc. Teas of poison moths such as Phalera flavescens, such as horned moths such as Lampides boeticus, Ascotis selenaria of moths, Agrius convolvuli, etc. Oriental tussock moth (Euproctis pseudoconspersa), hell Oriental tussock moth (Orygia recens approximans), etc., the number of the garden tiger moth black juljeom garden tiger moth (Spilosoma imparilis), American white garden tiger moth (Hyphantria cunea), such as cherries go ipmalyi moth (Endopiza viteana), kodeul ring moth Adults, larvae and eggs such as larvae (Laspeyresia pomonella):

Beetles (Coleoptera), for example, chafer beetles (Anomala cuprea), beetle beetles (Popillia japonica), grass beetle (Oxycetonia jucunda), Anomala geniculata, etc. Agrilus auriventris, etc., including the worm-like melannotus fortnumi, and the ladybug family, Epilachna vigintioctopunctata, etc., Anoplophora malasiaca, Xylotrechus pyrrhoderus, etc. Allium bugs (Aulacophora femoralis), corn leaf beetle (Diabrotica spp.), Flea leaf beetle (Phyllotreta striolata), tortoiseshell leaf beetle (Cassida nebulosa), pheadon brassicae, rice leaf beetle (Oulema oryzae), soybean beetle ), Colorado potato beetle (Leptinotarsa decemlineata), goose beetle (Rhynchites heros), and weed beetle (Cylas formicarius) Cucurio sikkimensis, Rice weevil (Lissorhoptrus oryzophilus), Cotton weevil (Anthonomus gradis grandis), Sphenophrus venatus vestitus, etc.Epuraea domina , Larvae and eggs ：

Heteroptera of Hemiptera, for example, Eurydema rugosum of the Hemiptera family, Eysarcoris lewisi, Eysarcoris parvus, Nezara viridula, Brown winged stinger (Plautia stali), Halymorpha mista, etc., such as ovary hemipterus (Urochela luteovoria), such as the mid-tolerance of Togo hemipterus, etc. Riptortus clavatus, Cryus punctiger, etc.Leptocorisa chinensis, etc., Lythocoptera, Dysdeercus cingulatus, etc. Rhododendron Pyramids (Stephanitis pyrioides), Blind stink bug, Apolygus spinolai, Red spot stink bug (Stenotus rubrovittalus), Red tentacles Norinjae's (Trigonotylus coelestialium), such as adults, such as shamans know pentatomidae know norinjae (Megacopta punctatissimum), larvae and eggs:

Homooptera of Hemiptera, for example, Platypleura kaempferi, Arboridia apicalis, Empoasca onukii, Nephew cicada (Nephotettix) cincticeps, Nephotettix virescens, Latodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, etc., Geisha distinctissima, etc.

Psylla pyrisuga, Diaphorina citri, and other biotypes of Aleurocanthus spiniferus, Bemisia argentifolii, Bemisia tabaci, Tangerine powder, etc. (Dialeurodes citri), Trialurodes vaporariorum,

Aphis citricola, Aphis craccivora, Aphis gossypii, Aphid gossypii, Aphid aphid, Aulacorthum solani, Cabbage aphids, such as the vine root beetle (Viteus vitifolii) (Brevicoryne brassicae), tangerine aphid (Toxoptera aurantii), tangerine aphid (Toxoptera citricidus), elderberry aphid (Aulacorthum magnoliae), pear tree aphid (Schizaphis piricola), pear tree aphid pith (Nippolachnus) (Lipaphis erysimi), Peach aphid (Hyalopterus pruni), Prickly aphid (Pleotrichophorus chrysanthemi), Chrysanthemum mustard aphid (Macrosiphoniella sanborni), Long-tailed block aphid (Megoura crassicauda), Brisket aphid ivy (Sitobion) Macrosiphum euphorbiae, black knot aphid (Myzus varians), peach aphid (Myzus persicae), red rim aphid (Rhopalosiphum rufiabdominalis), Border hop aphid (Rhopalosiphum padi), bodhisattva aphid (Sitobion akebiae), apple worm (Eriosoma lanigerum), Icerya purchasi, etc., Pseudococcus comstocki , Tangerine pods (Phenacoccus viburnae), cotton worms (Phenacoccus kraunhiae), etc., grasshopper beetle (Ceroplastes ceriferus), ruby locust (Ceroplastes rubens),

Adults, larvae and eggs such as Aonidiella aurantii, San Jose locust (Comstockaspis perniciosa), Pseudaulacaspis pentagoa, and Unnaspis yanonensis:

Thysanoptera, for example, Scirtothrips dorsalis, Thrips palmi, Thrips tabaci, Thrips setosus, Taiwan Frankliniella intonsa, Frankliniella occidentalis, Helicothrips haemorrhoidalis, etc.Ponticulothrips diospyrosi, Haplothrips aculeatus

Hymenoptera, for example, Athalia rosae ruficornis, Arge pagana, etc., Arge mali, etc., Leaves bee, etc., Arge mali, Druocsmus kuriphilus Adults, larvae and eggs such as forged ant (Formica japonica) such as Megachile nipponica nipponica, etc.

Diptera, for example, Asphondylia yushimai of the Humpback family, Rhacochlaena japonica, Bactrocera cucurbitae, etc. (Hydrellia griseola), Drosophila suzukii, etc., Liliomyza trifolii, Pea (Chromatomyia horticola), Rice leaf oyster (Agromyza oryzae), Cucumber leaf oyster (Liriomyza bryoniae), etc. Adults, larvae and eggs such as Delia platura and Delia antiqua in the family

Orthoptera, for example, Ruspolia lineosa of the larvae, Truljalia hibinonis of the cricket family, Gryllotalpa orientalis, etc., and the larva of the grasshopper (Oxya yezoensis, etc.) Larvae and eggs:

Adults, larvae and eggs such as the termites (Isoptera), for example, the termites Odontotermes formosanus:

Adults, larvae and eggs such as Dermaptera, for example, Labidura riparia

Arthropod Moon Colony of the Insect River, for example, Sminthurus viridis of the Round Tocaceae family, such as the Onychiurus matsumotoi Adults, larvae and eggs such as:

Adults, larvae and eggs such as the Isopada of the crustacean, for example, Armadillidium vulgare

Arthropods Acari of the arachnid, for example, Polyphagotarsonemus latus, Phytonemus pallidus, etc.Penthaleus major of the mite family, such as the mite family Nectar mite (Brevipalpus lewisi), Mne mite (Brevipalpus phoenicis), Methanaceae Tango mite (Panonychus citri), Apple mite (Panonychus ulmi), Spotted mite (Tetranychus urticae), Chine mite (Tetranychus kanzawai), Pear mite Oregonychus ununguis, Eotetranychus kankitus, Bryobia praetiosa, Aculops pelekassi, Eriophyes chibaensis, Aceria tulipae Adults, larvae such as Colomerus vitis, Aculus fockeui and Calacarus carinatus, Tyrophagus putrescentiae and Rhizoglyphus robini Al:

Mollusca (Architaenioglossa), for example, Pomacea canaliculata, Plumonata, for example, African snail (Achatina fulica), Slug (Meghimatium bilineatum) ), Niwa-koura slug (Milax gagates), Koura slug-like Czechura (Lehmannina valentiana), snail (Acusta despecta sieboldiana):

Root rot nematodes, such as Tylenchorhynchus claytoni, including the melon parasite Nematode Nematodes, such as Dylenchus destructor of the linear animal portal ventilation cavity, for example, Ditylenchus destructor Potato root nematode (Globodera rostochiensis) including black nematodes, such as Prattylenchus penetrans, Prattylenchus coffeae, and Helicocytosis nematodes (Helicotylenchus dihystera) Meloidogyne incognita, Criconema jaejuense, such as Criconema family, Nothotylenchus acris, etc., Aphelecchoides fragria, etc.

The nematode of the ulna river and the nematode of the Longidorinae family (Xiphinema sp.), And the trichodor nematode (Trichodorus sp.) Of the Trichoderus family are mentioned.

The compounds of the present invention can be used to act indoors of buildings, including ordinary houses, to add wood and processed products such as wooden furniture, stored food, clothing, books, etc., and to control pests that damage our lives. have. As a specific marine species, the termite of the arthropod gate, the termite of the Leptotermes domesticus of the Kalotermitidae family, such as the termites, such as the Yamato termites (Reticulitermes speratus) and the termites (Coptotermes formosanus), Larvae and eggs:

Coleoptera, for example, weevil weevil (Sitophilus zeamais) and rice weevil (Sitophilus zeamais), such as weevil weevil (Callosobruchus chinensis), pea weevil (Bruchus pisorum), and weeping weevil weevil (Bruchus rufis) , Black-headed worms, Tribolium castaneum, Tribolium confusum, etc., and black-headed beetles, Oryzaephilus surinamensis, Cryptolestes pusillus, etc. Insects (Lasioderma serricorne), Ginseng (Stegobium paniceum), Attagenus unicolor japonicus, Anthrenus verbasci, Dermestes maculatus, etc. Such as bamboo tree bark (Dinoderus minutus) and dogwood bark (Rhizopertha dominica), etc. Caterpillars, Larvae and Eggs ：

Lepidoptera, for example, Cadra cautella from the Great Moth, Ephestia kuehniella, Plodia interpunctella, etc., Sitotroga cerealella, etc. Adults, larvae and eggs such as Tinea translucens and Tineola bisselliella in grain moths:

Adults, larvae and eggs, such as Lepinotus reticulatus, such as Lepinotus reticulatus, such as Lepinotus reticulatus:

Adults, larvae and eggs such as wheel rims such as the Flattella germanica of the German rim family, the Periplaneta fuliginosa, the Periplaneta japonica, etc .:

Adults, larvae and eggs such as the moth, for example, the Yamato moth (Ctenolepisma villosa) and the western moth (Lepisma saccharina), etc .:

Adults, larvae and eggs such as the flyfly, for example, the Drosophila melangogaster, Drosophila melangogaster, and the Pyophila casei, etc.

Arthropods of the arachnids, for example, adults, larvae and eggs, such as Carpoglyphus lactis of the sugar mite family, such as Tyrophagus putrescentiae of the dust mite, Largoglyphus konoi, etc. have.

The compound of the present invention can also be used for controlling marine organisms that cause natural forests, artificial forests, trees of urban greenery or weaken the growth of trees. As specific marine organisms, arthropods of the arthropods, insects, for example, cedars moths (Calliteara argentata), moths (Euproctis pseudoconspersa), moths (Orygia recens approximans), moths (Euproctis subflava), nymphs (Lymantria dispar) Macromoth with night moths (Crytoblabes loxiella, etc.) Agrotis segetum, Ptycholoma lecheana circumclusana, Leafy moth, Cydia kurokoi, Cydia cryptomeriae, and Black-tailed moth (Spilosoma imparilis) Parasa lepida, black nettle, etc., with moths such as Hyphantria cunea, and Stigmella castanopsiella with the moth. (Scopelodes contracus), kid adult moths such as a wedge (Microleon longipalpis), larvae and eggs:

Coleoptera (Monochamus alternatus), such as the chafer, Anomala rufocuprea, Heptophylla picea, etc., Agrilus spinipennis, etc. , Bacillepta pallidula, leaf beetle, etc., Seaweed weevil (Scepticus griseus), White spotted weevil (Shirahoshizo insidiosus), and Siberinus gigas, etc. Adults, larvae and eggs such as powdered bark (Rhizopertha dominica) with the bark, etc., such as Indocryphalus aceris:

Cicada, for example, aphid aphids such as Cinara todocola, Adelges japonicus, etc., Apoddiotus cryptomeriae, etc. , Larvae and eggs such as (Ceroplastes ceriferus):

Lumber, larvae and eggs, such as the bee bee (Dryocosmus kuriohilus), including felling, for example, Larch bee (Pachynematus itoi), and the pine needle bee (Neodiprion sertifer)

Flies, for example, Tipula aino of the family Asteraceae, Strobilomyia laricicola of the family Asteraceae, Contarinia inouyei of the family Hominidaceae, Contarinia matsusintome, etc. Adults, larvae and eggs:

Arthropods of the arachnids, for example, adults, larvae and eggs such as cedar mite (Oligonichus hondoensis) and fir leaf mite (Oligonichus ununguis):

Examples of the linear animal portal ventilator cane include the nematode of the Parasitap helenchidae family (Bursaphelenchus xylophilus).

Compounds of the present invention are arthropods, nematodes, insects parasitic internally or externally to livestock or pets, such as cattle, sheep, goats, horses, pigs, poultry, dogs, cats, and fish, which are vertebrates, particularly warm-blooded vertebrates. It can also be used for the prevention, treatment or control of worms, insects and protozoa. In addition to the above, the target animal species include rodents such as mice, rats, hamsters, leases, carnivorous trees such as pellets, pets of animals such as ducks, pigeons, and experimental animals. As a specific marine organism, the arthropods of the arthropods, insects, etc., for example, Tabanus rufidens, Tunganus chrysurus, etc. calcitrans), horsefly family (Gasterophilus intestinalis), horsefly family (Hypoderma bovis), onion family family (Oestrus ovis), hair black family family (Aldrichina grahami), flea family Flea fly (Megaselia spiracularis),

Mosquitoes such as the Sepsis punctum, Royal Moths of the Moth (Telmatoscopus albipunctatus), Psychoda alternata, Culex pipiens molestus, Culex pipiens pallens, etc. , Chinese spotted mosquito (Anopheles sinensis), small red-billed mosquito (Culex pipiens triaeniorhynchus summorosus), white lined mosquito (Ades albopictus), Simulium iwatense, Prosimulium yezoense Adults, larvae and eggs such as Culicoides schulzei and Culcoides arakawae

Adults, larvae and eggs of fleas, for example, Pulex irritans and dog fleas (Ctenocephalides canis) with human fleas:

Oysters, for example, Haematopinidae suis, Haematopinidae eurysternus, Damalinia bovis, etc., and Linognathus vituli in the canine family, Adults, larvae and eggs such as Menopon gallinae):

Arthropods Arachnids, such as Vararoa jacobsoni, Haemaphysalis longicornis, Ixodes ovatus, Boophilus microplus Amplyomma testudinarium, Scissor-chopper mite (Ornithonyssus sylvialum), Chicken red marrow (Dermanyssus gallinae), Demodex phylloides, etc. Adults, larvae and eggs such as Sarcoptes scabiei bovis, Knemidocoptes mutans, Otodectes cynotis, and Psoroptes communis.

Protozoans of the linear animal portal twins, for example, locusts, swine worms, swine worms, shape nematodes, ileum worms:

Roundworms, such as pig roundworms and chicken roundworms:

Filamentous animal portal rodents, for example, Japanese schistosomiasis, hepatitis, green twin mouthworm, Westerman lungworm, Japanese eggworm:

Insects, for example, leaf insects, expansion insects, beneden insects, square insects, self-help insects, areola insects, etc .:

Root flagella of protozoa, flagella, etc., for example, Histomonas, etc., flagella, etc., Leishmania, Trypanosoma, etc., multiple flagella, eg Giardia, flagella, etc., Trichomonas, etc .:

Meat amoeba, for example, Entamoeba:

Pyroplasma steels of spores, for example, Theilaria, Babesia and the like, for example, spermatozoa, for example, Eimeria, Plasmodium, Toxoplasma and the like.

The compounds of the present invention can also be used to control harmful organisms that are directly harmful or unpleasant to the human body, or to maintain a sanitary state for marine organisms that carry or mediate pathogens. As specific marine organisms, the arthropods include the lepidoptera of the insect river, for example, Sphrageidus similis of the moths, and Kunugia undans of the moths, and the blue moths of the moss, Parasa consocia, etc. Bamboo nettle moth (Artona martini),

Coleoptera, for example, Xanthochroa waterhousei of the Astragalus family, and Epicauta gorhani, such as the Panax family, and fellings such as Paederus fuscipes of the half-wing family Yellow hornets of the family (Vespa simillima xanthoptera), antler family Brachyponera chinensis, such as the great warlords (Batozonellus annulatus),

Flycatcher, such as the Armigeres subalbatus, such as the mosquito (Culicoides nipponensis), and the Chinomus yoshimatsui of the midget family, etc. (Simulium nikkoense) Etc. Hirosia humilis of the back family, musca domestica of the housefly family, Fannia canicularis of the housefly family, Phormia regina of the black fly family, Sarcophaga of the family Flies adults, larvae and eggs such as peregrina):

Adults, larvae and eggs such as fleas, eg, Pulex irritans with human fleas:

Adults, larvae and eggs such as wheel rims such as Bratella germanica of the German rim, Periplaneta americana, Periplaneta fuliginosa, Periplaneta japonica, etc .:

Adults, larvae and eggs such as Orthoptera, for example, Diestrammena japonica, Diestrammena apicalis, etc .:

Adults, larvae and eggs such as Pediculus humanus humanus, Phthirius pubis, etc., larvae, and eggs: stinkwood, such as Cimex lectularius, acupuncture Adults, larvae and eggs of Isyndus obscurus: Adults, larvae and eggs of the colloidola of the tripods of the triangular anterior insects, for example, Hypogastrura communis of the Chambratotoaceae family:

Arthropods Mite of the arachnid, for example, Ixodes persulcatus of the True Mite family, Ornithonyssus bacoti of the Scissor Mite family, and the Minamitsume Mite of the Claw family Pseemotes ventricosus, Demodex folliculorum, etc., Deer mite, Dermotophagoides pteronyssinus, Sarcoptes scabiei, etc. Adults, larvae and eggs such as:

Spermophora senoculata, Phoecus spider, such as the Hermit Spider, Chiracanthium japonicum, etc., Heteropoda venatoria, etc. Adults, larvae and eggs, such as the Pteroppus paykulli and Plexippus adansoni, such as phalangioides, Uroctea compactilis, etc.

Adults, larvae and eggs such as scorpions, eg, Isometrus europaeus, from the Far Eastern scorpion:

Arthropods: Larvae, larvae and eggs such as the royal neck of the Centipede River, for example, the Scolopendra subspinipes mutilans and the Scolopendra subspinipes japonica of Japan.

Adults, larvae and eggs such as Grima, for example, Thereuronema hilgendofi.

Adults, larvae and eggs, such as the banded tree of the arthropod gate, for example, the Oxidus gracilis of the Anthracnose scavenger:

Adults, larvae and eggs such as the isopods of the arthropod crustacean, for example Porcellio scaber:

Circumferential animal door Leech wood, for example, the tiger leech (Haemadipsa zeylanica japonica) and the like.

The compounds of the present invention are particularly valuable for controlling marine organisms, such as arthropods, gastropods, and nematodes, which cause damage to crops, natural forests, artificial forests, trees and appreciation plants of urban green spaces. In such a scene, the compounds of the present invention, in their commercially useful preparations and in the form of use prepared by these preparations, may contain other active compounds, such as insecticides, acaricides, nematicides, fungicides, aerosols, plant modifiers. It may also be present as a poison or admixture with herbicides.

As a usage form, a flowable agent, a capsule, powder, a granule, a bait, an aerosol, etc. can be taken as a hydrating agent, a granulating hydrating agent, a water-soluble agent, an oil agent, a chemical | medical agent, an underwater suspension agent, and an oil-in-water emulsion. In these preparations, the compound of this invention is 0.001-95 mass% normally in total amount, Preferably, 0.1-60 mass% is contained.

In order to control arthropods, gastropods, and nematodes, it is usually sprayed on the foliage of plants for the place where damage by these marine organisms occurs, or the place where the damage may occur, and the soil whole layer mixing, the construction operation ( It can also be used by absorbing it from the roots by treating it with soil, such as soiling, soil blending, cell seedling treatment, hole planting treatment, main treatment, top dressing, boxing of rice, water treatment, etc. have. It is also possible to immerse the seed in a chemical agent, to treat the seed, such as KARUPA treatment, to apply the nutrient solution in nutrient solution (hydroponic) cultivation, smoke screen technique, or trunk injection technique.

In the case of use, although it depends on the kind of aquatic organisms, the quantity of generation | occurrence | production, and the kind, cultivation form, and growth state of the target crop, a tree, generally 0.1-1000 g is preferable for the amount of the compound of this invention per 10 are. Preferably, 1 to 100 g is used. In order to process this, in a hydrating agent, a granulating hydrating agent, a water-soluble agent, an emulsion, a chemical liquid, a floating agent such as an underwater suspension agent and an oil-in-water emulsion, a capsule, etc., it is diluted with water, and the kind of plant to which it is made, the cultivation form, and the growth state Although it depends on, in general, it is good to apply | coat to crops etc. at a trial dose of 10-1000 liters per 10 ar. Moreover, in powder or aerosol, you may process to a crop etc. in the sanction state.

As an application method in the case where the target marine organisms mainly add a plant in the soil, or when the chemical | medical agent is absorbed from the root part, and the target marine organism is controlled, for example, without diluting or diluting a preparation with water, Application to main plant or seedling seedlings of plants, spraying granules to seedlings for main plant or seedlings of plants, spraying powders, hydrating agents, granulating agents, granules, etc. And spraying powder, hydrating agent, granulating hydrating agent, granulating agent and the like before or after planting or planting plants.

In hydrating agents, granulating hydrating agents, water-soluble agents, emulsions, potions, flocculating agents, such as aquatic suspensions and emulsions in water, capsules and the like, they are diluted with water and are generally used at a dosage of 5 to 500 liters per 10 liters. It is good to spray on the surface of soil so that it may evenly spread, or to spray on the surface of soil so that it may be equalized to the whole process area in the state of sanction in irrigation, powder, granules, or bait. Spraying or irrigation may be done around seeds or crops and trees which are to be protected from damage. In addition, the active ingredient may be mechanically dispersed by lightening during or after spraying.

As a method of application to a seedling box of water supply, the dosage form may vary depending on the time of application such as application at the time of sowing, application at the time of planting, application at the time of transplantation, etc. What is necessary is just to apply it in formulations, such as a granulation agent. It can also be applied by mixing with clay, and can be mixed with clay, powder, granulating agent or granules, for example, soil mixing, soil mixing, mixing with the whole soil. In addition, you may apply and apply clay and various materials alternately in layers.

As a method of application to rice paddy, solid preparations such as jumbo, packs, granules, and granular wetting agents, and liquid preparations such as floorables and emulsions are usually sprayed onto freshwater rice fields. In addition, at the time of planting, a suitable material can be mixed as it is or mixed with fertilizer etc., and can be sprayed and inject | poured into soil. Moreover, by using chemical liquids, such as an oil agent and a floor, based on the inflow of water to rice fields, such as a water port and an irrigation apparatus, it can also apply | generate dynamically according to supply of water. As a method of seed treatment, for example, a method of diluting or diluting a liquid or solid agent to immerse the seed in a liquid state to attach and penetrate the drug, and mixing the solid or liquid agent with the seed and treating the seed And a method of adhering to the surface of the seed, mixed with an adhesive carrier such as a resin and a polymer, coating the seed, and spraying the seed at the same time as the seeding. The "seed" which performs the said seed treatment means the plant of the beginning of cultivation used for propagation of a plant, For example, in addition to a seed, it is bulb, tuber, seed potato, shoot, parenting, agar Or a vegetative propagation plant for folding cultivation. In addition, the "soil" or "cultivation carrier" of a plant at the time of application shows the support for growing a crop, especially the support which makes a root, and if a material is not specifically limited, If it is a material which a plant can grow, The so-called soil, seedling mat, water, or the like may be used, and specific materials include sand, pumice, vermiculite, diatomaceous earth, agar, gelled material, polymer material, rock wool, glass fiber, wood chips, bark, and the like. Can be mentioned.

As the seeding of the cultivated plant to be transplanted and the treatment of the seedling period, in addition to the direct treatment to the seed, the irrigation treatment of the medicinal agent in the liquid phase or the spraying treatment of the granules on the seedling seedlings are preferable. In addition, it is also a preferable process to process a lip agent by planting at the time of planting, or to mix with a cultivation carrier near a transplant site.

The compounds of the present invention are also valuable for protecting wood (timber, lumber, processed wood, storage wood or structural wood) from harm such as termites or beetles. In such a scene, it is possible to control the wood or the soil around it by the method of spraying, injecting, irrigation, coating, powdering, granulating, etc. of the emulsion, emulsion, hydrating agent, and sol. In addition, emulsions, emulsions, wetting agents, powders, etc. used in the present scene may be present as a mixture with other active compounds, for example, insecticides, acaricides, nematicides, fungicides, repellents or aerosols. In the compound, the total amount of the compound of the present invention is 0.0001 to 95% by mass, preferably 0.005 to 10% by mass in an oil agent, a powder or a granule, and 0.01 to 50% by mass in an oil agent, a wetting agent and a sol. When controlling termites or beetles, 0.01 to 100 g is sprayed onto the soil or wood surface as the amount of the active ingredient compound per 1 m ² .

The compound of the present invention is protected from the addition of butterflies, beetles, and ticks when storing products such as cereals, fruits, fruits, spices, and tobacco in the state of being intact, powdered, or mixed in the product. It is available to do. It also protects against attacks from butterflies, beetles, zombies and wheels, even when storing animal products (leather, hair, wool and feathers, etc.) or plant products (cotton, paper, etc.) in natural or telephony state. In addition, it can protect from attack by butterfly trees, beetles, flies, and ticks when storing food such as meat and fish. In such scenes, it is possible to control by emulsions, emulsions, hydrating agents, powders, spraying resins, evaporators, treatment of smokers and fumigants, granules, tablets and poisons, spraying of aerosols and the like. Can be. In addition, these preparations may be present as a mixed agent with other active compounds, for example, insecticides, acaricides, nematicides, fungicides, repellents or aerosols, and in these preparations, the compounds of the present invention in a total amount of 0.0001 to It may contain 95 mass%.

Compounds of the present invention include arthropods that paralyze human and livestock body surfaces and cause direct harm, such as feeding or vampering of skin, arthropods, nematodes, reptiles, which prevail or mediate diseases of humans and livestock, It is valuable for the control or prevention of insects, protozoa, and arthropods that are offensive to humans. In such a scene, the compound of the present invention may be incorporated into a small amount, meal or feed, or an appropriate oral ingestable pharmaceutical composition, for example, a pharmaceutically acceptable carrier or tablets, pills, capsules containing a coating material, Pastes, gels, beverages, medicinal feeds, medicinal beverages, medicinal trends, embankment alleles, and other embankment devices that are held in the gastrointestinal tract, orally, or sprayed, powdered, grease, cream, ointment, emulsion It may be transdermally administered as a lotion, spot-on, pour-on, shampoo or the like. In order to achieve such an effect, generally, 0.0001-0.1 mass%, Preferably, 0.001-0.01 mass% can be contained with the compound of this invention. On the other hand, as a method of transdermal administration or topical administration, a device (for example, a necklace, a medallion, an ear tag, etc.) attached to the animal may be used to control arthropods locally or systemically.

Although the specific oral administration method and transdermal administration method at the time of using the compound of this invention as an insect repellent for animals or humans, such as a livestock, a pet, etc., are not necessarily limited to these.

When administered orally as a medicinal beverage, the beverage is usually a solution, suspension or dispersion in a suitable nontoxic solvent or water with a suspending or wetting agent such as bentonite, or other excipients. Generally beverages also contain antifoams. Beverage formulations may generally contain from 0.01 to 1.0 mass%, preferably from 0.01 to 0.1 mass% of the compound of the present invention.

When oral administration is desired in the unit use form of a dry individual, capsules, pills or tablets containing a predetermined amount of the active ingredient are usually used. These forms of use are prepared by homogeneously blending the active ingredient with appropriately finely divided diluents, fillers, disintegrants and / or binders such as starch, lactose, talc, magnesium stearate, vegetable rubber and the like. Such unit dosage regimens can vary widely the mass and content of the repellent by the type of host animal being treated, the extent of infection and the type of parasite and the weight of the host.

When administered with animal feed, it can be dispersed homogeneously in the feed, used as a top dressing or in the form of pellets. Usually, in order to achieve the desired antiparasitic effect, the compound of the present invention may be contained in the final feed, for example, 0.0001 to 0.05% by mass, preferably 0.0005 to 0.01% by mass.

Dissolved or dispersed in a liquid carrier excipient can be administered to an animal parenterally by intrapotent, intramuscular, intratracheal or subcutaneous injection. For parenteral administration, the active compound is preferably mixed with a suitable vegetable oil such as peanut oil, cottonseed oil. Such prescription can generally contain 0.05-50 mass% of compound of this invention, Preferably, 0.1-5.0 mass%. Moreover, it can administer locally by mixing with a suitable carrier like dimethyl sulfoxide and a hydrocarbon solvent. This material is applied directly to the animal's outer surface by spraying or direct stock price.

In addition, the compound of the present invention is an insect repellent such as an arthropod or an arthropod of a disease that directly inflicts harm, and sprays, injects, or sprays an emulsion, an emulsion, a hydrating agent, or the like to the surrounding environment in which such a marine organism can be latent. Spraying of irrigation, coating, powder, etc., fumigating agent, mosquito incense, self-burning fumigating agent, heating misting agent such as chemical reaction fuming agent, fuming agent such as fogging, treatment of ULV agent, granule, tablet and poison installation Or water, such as floating powder, granules, dropping into wells, reservoirs, reservoirs, and other flowing or rectified water. In addition, it is possible to control poisonous moths, which are also agricultural and forest pests, in the same manner as described above, or for flies, etc., to be mixed in animal feed and mixed with feces, and to mosquitoes. Mosquito-repellent devices, etc., are also useful for volatilizing the air. On the other hand, the preparations in the form of use thereof may be present as a mixture with other active compounds, for example, insecticides, acaricides, nematicides, fungicides, repellents or aerosols, these preparations in a total amount of the compound of the present invention, For example, it is suitable to contain 0.0001-95 mass%.

The compound of this invention may exist as a mixing agent with another active compound. In particular, by mixing with a compound (insecticide) having insecticidal activity, acaricide activity or nematicidal activity, it is possible to expand the pests to be controlled against pests, such as arthropods, gastropods and nematodes, which cause damage to plants. A synergistic effect such as a reduction of the dosage can be expected. Specific examples of the active compound include organophosphates such as azinephosmethyl, acephate, chloropyrifos, daizinon, dichlorvos and dimethone. Dimethyl-S-methyl, dimethoate, dimethylvinphos, disulfoton, ethion, fenitrothion, fenthion, Isoxathion, malathion, methamidophos, methidathion, monocrotophos, naled, oxydepropos, parathion parathion, phenthoate, phosalone, pirimiphos-methyl, pyridafenthion, profenofos, prothiofos, propaphos (propaphos), pyraclofos, salition, sulprofos, thiome (Thiometon), tetrachloride robin Force (tetrachlorvinfos), trichloroacetic phone (trichlorphon), bar shown thione (vamidothion), such as:

Carbamate agents such as alanikab, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, ethiophencarb ( ethiofencarb, fenobucarb, furathiocarb, isoprocarb, mesoyl, methomyl, metolcarb, pirimicarb, propoxur, thio Thiodicarb etc .:

Organic chlorine agents such as aldrin, chlordane, DDT (p, p'-DDT), endosulfan, lindane, and the like:

Pyrethroids, for example, acrinathrin, alletrin, bifenthrin, cycloprothrin cyfluthrin, cyhalothrin, cy Phenothrin, cypermethrin, deltamethrin, ethofenprox, fenpropathrin, fenvalerate, flucitrinate, flucythrinate, Flufenprox, fluvalinate, furamethrin, halfenprox, imiprothrin permethrin, phenothrin, prallethrin ), Pyrethrins, resmethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, etc .:

Neonicotinoid type, for example, acetamiprid, crotianidin, dinotefran, imidacloprid, nitenpyram, tiacloram Thiacloprid, thiamethoxam, etc .:

Insect growth regulators such as phenylbenzoylurease, for example, chlorofluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron Novaluron, tuflubenzuron, triflumuron, buprofezin, chromafenozide halopefenozide, methoxyphenozide (methoxyfenozide), terbufenozide, cyromazine, etc .:

Glaze hormones such as diofenolan, fenoxycarb, hydroprene, mesoprene, pyriproxyfen and the like:

Insecticides produced by microorganisms, such as abamectin, emamectin-benzoate, ivermectin, lepimectin, milbemectin, nema Necdenctin, Nikkomycin, Spinnetram, Spinosad, BT, etc .:

Insecticides derived from natural products, such as anabasine, azaadiractin, deguelin, fatty acid glycerides, hydroxypropylstarch, soy lecithin ), Lepimectin, nicotine, nornicotine, oroleic acid sodium salt, petroleum oil, propyleneglycol monolaurate, rapeseed oil rape oil, rotenone, etc .：

As other insecticides, for example, acetprole, bensultap, cartap, chiocyclam, chlorantraniliprore, chlorfenapyr, diafenci Diafenthiuron, ethylprole, fipronil, fipronil, flonicamid, flubenziamid, hydramethylnon, indoxaacarb, metaflumizone metaflumizone, metaaldehyde, nicotin sulfate, pymetrozine, pyridalyl, pyrifluquinqzon, spirotetramat, tolfenpyrad , Triazamate, etc .:

Acaricides such as acequinocyl, amitraz, azocyclotin, benzoximate, bifenazate, binapacryl, pheniso Bromopropylate, chinomethionat, clofentezine, cyenopyrafen, cyflumetofen, tricyclohexyl tin hydroxide, dicopol (dicofol), dienochlor, ethoxazole, penazaflor, penazaquin, fenbutatin oxide, fenbutatin oxide, fenothiocarb, fenpyoxymate ( fenpyroximate, fluacrypyrim, hexythiazox, pyrimidifen, polynactins, propargyl, pyridaben, pyridaben, spirodiclofen (spirodiclofen), spiromesifen, tebufenpyrad, tet Diphone (tetradifon), including:

Nematicides such as aluminum phosphide, benclothiaz, cadusafos, ethoprophos, fosthiazate, imicyafos ), Levamisol hydrochloride, mesulfenfos, metam-ammonium, methyl isothiocyanate, moranteltartarate, oxamyl, etc .:

Poison, for example,

Chlorphacinone, coumatetralyl, diphacinone, sodium fluoracetate, warfarin, and the like.

The compound of the present invention may be present as a mixture with other active compounds other than the compound having insecticidal activity, acaricide activity or nematicidal activity. In order to control diseases and / or weeds occurring simultaneously at the time of use, the mixture is used in combination with a compound having a bactericidal activity, a herbicidal activity or a plant growth regulation activity, and thus a synergistic effect such as a reduction in the amount of the drug is expected along with the reduction of the control effort. Can be. In addition, by using the mixture as a repellent or aerodynamic agent, a more effective control effect such as a synergistic effect can be expected.

Specific examples of such active compounds include fungicides, for example, DD (1,3-dichloropropene), acibenzolar-S-methyl, amissulbrom, anazine, and triazine. Azoxystrobin, basic copper sulfate, benomyl, benthiavalicarb-isopropyl, benthiazole, bitertanol, blastidine S ( blasticidin S, boscalid, bromuconazole, calcium carbonate, calcium polysulfide, captan, carbendazim, carpropamid , Chinomethionate (chinomethionat), chloroneb chloropicrin, chlorothalonil, complex of bis (ethylenediamine) copper-bis- (dodecylbenzenesulfonic acid), and cupric hydroxide hydroxide), copper nonylphenol sulfonate, salt St. copper chloride (copper oxychloride), a cyano Sowing imide (cyazofamid), when flu Pena imide (cyflufenamid), simok sanil (cymoxanil),

Cyproconazole, cyprodinil, dazomet, dichlofluanid, dichloymet, diclomezine, dilomezine, diethofencarb ), Difenoconazole, diflumetorim, dimethomorph, dithane-stainless, dithianon, dodine, echlomezole , Edifenphos, shiitake mycelium extract (extract from mushroom), fenamidone, fenarimol, fenbuconazole, fenhexamid, fenhexamid, fenoxanol ), Ferimzone, fluazinam, flumetover, fluopicolide,

Fluoroimide, fluquinconazole, flusulfamide, flutolanil, fosetyl-AL, fthalide, fludioxonil , Furametpyr, fuconazole, hexaconazole, hydroxyioxazole, hymexazol, imibenconazole, iminoctadine acetate , Iminoctadine-arbesylate (iminoctadine-DBS), ifconazole (ipconazole), IBP (iprobenfos), iprodione, iprovalicarb, isoprothiolane, isoprothiolane Mycine (kasugamycin), kresoxim-methyl, mancozeb, maneb, manzeb, mepanipyrim,

Mepronil, metalaxyl, metam-ammonium, metam-sodium, metconazole, metasulfocarb, methyl bromide, Methylisothiocyanate, metominostrobin, mildiomycin, myclobutanil, nickel dimethyldithiocarbamate, orissastrobin, oxadisil (oxadixyl), oxine-copper, oxolinic acid, oxpoconazole fumarate, oxycarboxin, oxytetracycline, pebulate, pepuulate Lazoate, pecicuron, penthiopyrad, polycarbamate, polyoxin B, polyoxin-B,

Polyoxins, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb, propiconazole ), Propineb, pyraclostrobin, pyrazophos, pyrifenox, pyrimethanil, pyrimethanil, pyroquilon, quintozene, Silver, simeconazole, sodium hydrogen carbonate, sodium hypochlorite, spiroxamine, streptomycin, sulfur, tebconazole (tebuconazole), tecloftalam, tetraconazole, thiabendazole, thiadiazin, thifluzamide, thiophanate, thiophanate Thiophanate-methyl, thiram, tiadinil, and tolk Tolsclofos-methyl, tolyfluanid, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triflumisol ( triflumizole, triforine, triticonazole, validamycin (-A), vinclozolin, zinc sulfate, zineb ziram, etc. Can be illustrated.

Examples of the compound having herbicidal activity include aclonifen, acifluofen-sodium, alachlor, alloxydim, amicarbazone and amidsulfuron amidosulfuron, anilofos, asulam, atrazine, azimsulfuron, benfuresate, bensulfuron-methyl, bentazone, Benthiocarb, benzobicyclon, benzofenap, bialaphos, bifenox, bromobutide, bromoxynil, bromoxy Butamifos, cafenstrole, calcium peroxide, carbetamide, cinosulfuron, clomeprop, cyclosulfamuron, cyclohalfamuron, sihal Cyhalofop-butyl, dimuron, desmedipham, diclofop-meth yl),

Diflufenican, dimefuron, dimethametryn, dinoterb, diquat, diuron, esprocarb, ethiozin ( ethiozin, ethofumesate, ethoxysulfuron, etobenzanid, phenoxaprop-P-ethyl, pentrazamide, flucarbazone , Flufenacet, flurtamone, fluthiacet-methyl, foramsulfuron, glufosinate-ammonium, glyphosate isopropylamine salt (glyphosate) -isopropyl amine), glyphosate-trimesium, imazapyr, imazosulfuron,

Indanopan, iodosufluron, ioxynil-octanoate, isoproturon, isoxadifen, isoxaflutole, isoxaflutole, lactofen, Linuron, mefenacet, mesosulfuron, metastrontron, metabenzthiazuron, metosulam, metosulam, metribuzin, napro Napropamide, neburon, oxadiargyl, oxadiazon, oxaziclomefone, paraquat, pendimethalin, pendimethalin, pentoxazone ( pentoxazone, phenmedipham, pretilachlor, propoxycarbazone, prosulfocarb, pyraclonil, pyraflufen-ethyl, Pyrazolate, pyrazosulfuron-ethyl, pyributicarb, pyriphthalide (pyriftalid), pyriminobac-methyl, quizalofop-ethyl, sethoxydim, simazine, simazine, sulfotrion, sulfentrazone ), Tenylchlor, triaziflam, tribufos and the like can be exemplified.

In addition, as a compound having a plant growth regulator action, for example, 1-naphthylacetic acid, 4-CPA (4-CPA), benzylaminopurine, butralin , Calcium chloride, calcium formate, calcium peroxide, calcium sulfate, chlormequat chloride, choline, cyanamide, cyclanyl Cyclanilide, daminozide, decyl alcohol, dichjoprop, ethephon, ethychlozate, flupriprimidol, pochloro Forclorfenuron, gibberellic acid, indolebutyric acid, maleic hydrazide potassium salt, mefenpyr, mepiquat chloride, auxin sulfate oxine sulfate, 8-hydroxyquinoline sulfate, paclobutrazol ), Paraffin, prohexadione-calcium, prohydrojasmon, thidiazuron, trinexapac, uniconazole-P, It may be used by mixing with a wax or the like.

Repellents such as capsaicin, carane-3,4-diol, citronellal, deet, dimethyl phthalate, hinokithiol ( hinokitiol, limonene, linalool, menthol, menthol, menthone, naphthalene, thiram, etc .: Aerosols, for example methylenedioxynaphthalene, Naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentynyl phthalimide, phenyl salioxone (phenyl salioxon) piperonil butoxide, saprole, sesamex, sesamin, sulfoxide, triphenyl phosphate, verbutin ), And the like.

The present invention is a biological pesticide, for example, cytoplasmic polyhedrosis virus (CPV), insect pox virus (Entomopox virus, EPV), granulosis virus (gV), nuclear polyhedral virus (Nuclear) Virus preparations such as polyhedrosis virus (NPV), Boberia bassiana, Boberia brongniartii, Monoclosporium phymatophagum, Pasilomyses and Pumosolos Paecilomyces fumosoroseus Pasteur penetrans, Steinerema carpocapsae, Steinernemaglaseri, Steinerema kushidai, Steinerema kushidai Microbial pesticides used as insecticides or nematicides such as Verticillium lecanii, Agrobacterium radiobactor,

Bacillus subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02, Pseudomonas fluor Sons Mai to (Pseudomonas fluorescens), Tara process, Plastic bus (Talaromyces), tricot der e & art to irregularities having (Trichoderma atroviride), tricot der town League noreom microorganism is used as the sterilizing agent, such as (Trichoderma lignorum) pesticides, greater The same effect can be anticipated by using in mixture with biological pesticides used as a herbicide, such as Santomonas campestris.

In addition, as biopesticides, for example, Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidzalet aphid ), Flycatcher dragonfly (Chrysoperia carnea), Dflynula sibirica, Dylyphus isaea, Encarsia formosa, Eretmocerus eremicus, Franklinoprips vespiformis vespiformisrips ), 18-spotted ladybug (Harmonia axyridis), yellow-tailed beetle (Hemiptarsenus varicornis), oyster fly blue zombie (Neochrysocharis formosa), yellowtail (Orius sauteri), yellowtail (Orius strigicollis), Chilean mediterranean (Phymiliosulus) Natural creatures, such as Black-headed Plaid (Pilophorus typicus) and Big Coccinus (Piocoris varius), codlelure, cuelure, geraniol, and gyptol tol, liblure, looplure, methyl eugenol, orfralure, peachflure, phycilure, pyrimalure, tur It is also possible to use together with pheromone agents, such as pentine oil (turpentine).

Example

Although an Example, a preparation example, and a test example demonstrate this invention further in detail below, the scope of the present invention is not limited to these Examples, a preparation example, and a test example.

Reference Example 1 (Preparation of Compound Corresponding to Compound [4] in Scheme 1)

Synthesis of 3-methoxyoxalylamino-N- (2-ethyl-4-heptafluoroisopropyl-6-methyl) phenylbenzamide

8.45 g of 3-amino-N (2-ethyl-4-heptafluoroisopropyl-6-methyl) phenylbenzamide was dissolved in 80 ml of tetrahydrofuran, 3.4 ml of triethylamine and 0.3 g of 4-dimethylaminopyridine were added, followed by ice cooling. What diluted 2.45 g of methoxychlorooxarate with 10 ml of tetrahydrofuran was dripped at 10 degrees C or less below. Thereafter, the reaction solution was poured into dilute hydrochloric acid, and the precipitated crystals were filtered, washed with water and dried to obtain a crude product. Furthermore, the mixture was washed with a mixed solvent of hexane and ethanol (5: 1) to obtain 8.53 g of an intermediate of the compound of the present invention. Melting Point 160 ~ 163 ℃

Example 1 (Preparation of a compound corresponding to compound [1] of Scheme 1)

Synthesis of 3- (N, N-dimethylaminooxalylamino) -N- (2-ethyl-4-heptafluoroisopropyl-6-methyl) phenylbenzamide (Compound No.1-37)

0.76 g of 3-methoxyoxalylamino-N (2-ethyl-4-heptafluoroisopropyl-6-methyl) phenylbenzamide and 0.25 g of dimethylamine hydrochloride are suspended in 7 ml of methanol and a 28% sodium methoxymethanol solution Was added dropwise, the mixture was stirred overnight at room temperature, water was added to the reaction solution, and the precipitate precipitated was filtered, washed with water and dried to obtain 0.78 g (amorphous) of the compound (No.1-37) shown in Table 1.

¹ H-NMR (CDCl ₃ ), δ ppm: 1.23 (3H, t), 2.36 (3H, s), 2.70 (2H, q), 3.12 (3H, s), 3.53 (3H, s), 7.37 (2H, s), 7.48-7.55 (2H, m), 7.70-7.79 (2H, m), 8.28 (1H, s), 9.49 (1H, s)

Example 2 (Scheme 1)

Synthesis of 3- (N-cyclopropylaminooxalylamino) -N- (2,6-dimethyl-4-heptafluoroisopropyl) phenylbenzamide (Compound No. 1-6)

0.99 g of 3-methoxyoxalylamino-N- (2,6-dimethyl-4-heptafluoroisopropyl) phenylbenzamide was suspended in 6 ml of methanol, and 0.25 g of cyclopropylamine diluted with 2 ml of methanol was added dropwise. After stirring overnight at room temperature, water was added to the reaction solution, and the precipitated precipitate was filtered, washed with water and dried to obtain 1.01 g of the compound (No. 1-6) shown in Table 1. Melting Point 204 ~ 206 ℃

Example 3 (Scheme 2)

Synthesis of 3- (N, N-diethylaminooxalylamino) -N- (2-ethyl-4-heptafluoroisopropyl-6-methyl) phenylbenzamide (Compound No.1-49)

0.63 g of 3-amino-N- (2-ethyl-4-heptafluoroisopropyl-6-methyl) phenylbenzamide and 0.22 g of N, N-diethylaminooxamic acid and 2-chloro-1-methylpyridinium 0.38 g of iodide was suspended in 7 ml of tetrahydrofuran, 0.63 ml of triethylamine was added thereto, and the mixture was heated to reflux for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate, followed by washing with water and an aqueous sodium chloride solution, followed by magnesium sulfate. After drying with water, the solvent was distilled off by an evaporator under reduced pressure to obtain 0.81 g (amorphous) of the compound (No. 1-49) shown in Table 1.

¹ H-NMR (CDCl ₃ ), δ ppm: 1.18-1.26 (6H, m), 1.31 (3H, t), 2.33 (3H, s), 2.69 (2H, q), 3.47 (2H, q), 3.83 ( 2H, q), 7.36 (2H, s), 7.46 (1H, t), 7.68-7.79 (3H, m), 8.23 (1H, s), 9.63 (1H, s)

Example 4 (Scheme 1)

Synthesis of 3- (N-ethylaminooxalylamino) -N- (2-ethyl-4-heptafluoroisopropyl-6-methyl) phenylbenzamide (Compound No.1-35)

0.76 g of 3-methoxyoxalylamino-N- (2-ethyl-4-heptafluoroisopropyl-6-methyl) phenylbenzamide was suspended in 7 ml of methanol, and 0.16 g of ethylamine 70% aqueous solution was added dropwise, and overnight at room temperature. After stirring, water was added to the reaction solution, and the precipitated precipitate was filtered, washed with water and dried to obtain 0.78 g of the compound (No.1-35) shown in Table 1. Melting Point 220 ~ 222 ℃

Example 5 (Scheme 3)

Synthesis of 3- (N-methyl-N-cyclohexylaminooxalylamino) -N- (2-ethyl-4-heptafluoroisopropyl-6-methyl) phenylbenzamide (Compound No.1-48)

0.63 g of 3-amino-N- (2-ethyl-4-heptafluoroisopropyl-6-methyl) phenylbenzamide and 0.24 g of pyridine are suspended in 7 ml of tetrahydrofuran and N-methyl-N-cyclohexylamino under ice cooling After diluting 0.35 g of oxaryl chloride with 2 ml of tetrahydrofuran, the mixture was stirred overnight at room temperature, then diluted hydrochloric acid was added to the reaction solution, extracted with ethyl acetate, washed with water, aqueous sodium chloride solution, and dried over magnesium sulfate. Thereafter, the solvent was distilled off under a reduced pressure with an evaporator to obtain 0.87 g (amorphous) of the compound (No.1-48) shown in Table 1.

¹ H-NMR (CDCl ₃ ), δ ppm: 1.02-1.90 (13H, m), 2.36 (3H, s), 2.70 (2H, q), (2.95 + 3.28) (3H, s), ((4.31- 4.43) + (4.64-4.76)) (1H, m), 7.37 (2H.s), 7.49 (1H, t), 7.62 (1H, s), 7.69-7.79 (2H, m), 8.24 (1H, s ), (9.44 + 9.51) (1H, s)

Example 6 (Scheme 1)

Synthesis of 3- (pyrrolidin-1-yl-oxalylamino) -N- (2,6-dimethyl-4-heptafluoroisopropyl) phenylbenzamide (Compound No.1-33)

0.99 g of 3-methoxyoxalylamino-N- (2,6-dimethyl-4-heptafluoroisopropyl) phenylbenzamide is suspended in 8 ml of methanol, 0.21 g of pyrrolidine is added dropwise, and stirred overnight at room temperature, and the reaction is carried out. Water was added to the solution, and the precipitated precipitate was filtered, washed with water and dried to obtain 1.04 g (amorphous) of the compound (No.1-33) shown in Table 1.

¹ H-NMR (CDCl ₃ ), δ ppm: 1.85-2.07 (4H, m), 2.36 (6H, s), 3.36 (2H, t), 4.07 (2H, t), 7.36 (2H, s), 7.51 ( 1H, t), 7.65 (1H, s), 7.71-7.78 (2H, m), 8.32 (1H, s), 9.68 (1H, s)

Example 7

3- (N- (t-butyl) -N-methylaminooxalylamino) -N- (2-chloro-4-heptafluoroisopropyl-6-methyl) phenylbenzamide (Compound No.1-61) synthesis

Example 7-1 (1)

Synthesis of N- (t-butyl) -N-methylethoxyoxarylamide

15.08 g of t-butyl methyl amine was diluted with 200 ml of t-butyl methyl ether, 27.4 ml of triethylamine was added thereto, and 24.85 g of ethyl oxarylyl chloride was added dropwise to 40 ml of t-butyl methyl ether under ice cooling, followed by completion of the dropwise addition. Dilute hydrochloric acid to the solution, separate the organic layer, and the organic layer is washed with sodium bicarbonate and saturated brine, dried over magnesium sulfate, and t-butyl methyl ether is distilled off to obtain N- (t-butyl) -N-methyl as a target compound. 30.25 g (yield 93.4%, oil phase) of ethoxyoxarylamide was obtained.

¹ H-NMR (CDCl ₃ ), δ ppm: 1.36 (3H, t), 1.46 (9H, s), 2.88 (3H, s), 4.31 (2H, q)

Example 7- (2)

Synthesis of N- (t-butyl) -N-methylaminooxamic acid

20.0 g of N- (t-butyl) -N-methylethoxyoxarylamide was suspended in 30 ml of methanol and 50 ml of water, and 9.42 g of a 50% aqueous sodium hydroxide solution was added dropwise under ice cooling, followed by stirring for 1 hour. Concentrated hydrochloric acid is added to make acidic, t-butyl methyl ether is added thereto, the organic layer is washed with water, dried over magnesium sulfate, t-butyl methyl ether is distilled off and the target compound is N- (t-butyl) -N-methylamino. 12.37 g (yield 73%, solid) of oxamic acid was obtained.

¹ H-NMR (CDCl ₃ ), δ ppm: 1.47 (9H, s), 3.13- (3H, s), 7.23- (1H, bs)

Example 7- (3) (Scheme 2)

3- (N- (t-butyl) -N-methylaminooxalylamino) -N- (2-chloro-4-heptafluoroisopropyl-6-methyl) phenylbenzamide (Compound No.1-61) synthesis

0.43 g of 3-amino-N- (2-chloro-4-heptafluoroisopropyl-6-methyl) phenylbenzamide and 0.18 g of N- (t-butyl) -N-methyloxamic acid and 2-chloro-1 0.28 g of methylpyridinium iodide was suspended in 6 ml of tetrahydrofuran, 0.46 ml of triethylamine was added, the mixture was stirred overnight at room temperature, and the solvent was removed from the reaction mixture under reduced pressure, and then the residue was purified by silica gel column chromatography. Purification with (hexane: ethyl acetate = 1.5: 1) gave 0.53 g (amorphous) of the compound (No.1-61) shown in Table 1.

¹ H-NMR (CDCl ₃ ), δ ppm: 1.49 (9H, s), 2.42 (3H, s), 3.24 (3H, s), 7.44 (1H, s), 7.51 (1H, t), 7.57 (1H, s), 7.71-7.79 (2H, m), 7.85 (1H, s), 8.26 (1H, s), 9.22 (1H, s)

Example 8

3- (N- (2fluoroethyl) -N-methylaminooxalylamino) -N- (2-ethyl-4-heptafluoroisopropyl-6-methyl) phenylbenzamide (Compound No.1-103) synthesis

Example 8- (1)

Synthesis of N- (2-fluoroethyl) methoxyoxarylamide

14.17 g of dimethyl oxalate and 10.00 g of 2-fluoroethylamine hydrochloride were dissolved in 130 ml of methanol, and 19.30 g of a methanol solution of 28% sodium methoxide was diluted with 30 ml of methanol under ice cooling. After completion of the dropwise addition, the reaction solution was brought to room temperature, and crystals precipitated in the reaction solution were filtered. The filtrate was concentrated under reduced pressure, diethyl ether was added to the residue, and the precipitated crystals were filtered again. Diethyl ether was collected from the filtrate to obtain N- (2-fluoroethyl) -methoxyoxarylamide 10.63 as a target compound. g (yield 79.3%, oily matter) was obtained.

¹ H-NMR (CDCl ₃ ), δ ppm: 3.62-3.74 (2H, m), 3.93- (3H, s), 4.54 (1H, t), 4.61 (1H, t), 7.47 (1H, br)

Example 8- (2)

Synthesis of N- (2-fluoroethyl) -N-methylmethoxyoxarylamide

To 3.00 g of N- (2-fluoroethyl) -methoxyoxarylamide, 25 ml of N, N-dimethylformamide, 5 ml of dimethoxyethane, and 4 ml of methyl iodide were added. Under ice cooling, 0.96 g of sodium hydride (60% in oil) was added. The reaction solution was allowed to stand at room temperature, diluted with hydrochloric acid and ethyl acetate, the organic layer was washed with water, dried over magnesium sulfate, ethyl acetate was distilled off, and the resulting product was washed with hexane to give N- (2-fluoroethyl)-as a target compound. 1.66 g (yield 50.9%, oil) of N-methylmethoxyoxarylamide was obtained.

¹ H-NMR (CDCl ₃ ), δ ppm: (3.09 + 3.14) (3H, s), (3.61-3.77) (2H, m), 3.87 + 3.90 (3H, s), 4.52-4.71 (2H, m)

Example 8- (3)

Synthesis of N- (2-fluoroethyl) -N-methyloxamic acid

1.56 g of N- (2-fluoroethyl) -N-methylmethoxyoxarylamide was suspended in 6 ml of methanol and 5 ml of water, and under ice-cooling, 3.2 g of an aqueous 15% sodium hydroxide solution was added dropwise and stirred for 1 hour to add concentrated hydrochloric acid, and acetic acid. Ethyl was added and the mixture was washed with water, the organic layer was washed with water, dried over magnesium sulfate, ethyl acetate was added thereto, and 0.94 g (yield 66%, solid) of the target compound, N- (2-fluoroethyl) -N-methylaminooxamic acid, was added. Got it.

¹ H-NMR (CDCl ₃ ), δ ppm: (3.19 + 3.48) (3H, s), ((3.72-3.82) + (4.08-4.18)) (2H, m), 4.48-4.76 (2H, m)

Example 8- (4) (Scheme 2)

3- (N- (2-fluoroethyl) -N-methylaminooxalylamino) -N- (2-ethyl-4-heptafluoroisopropyl-6-methyl) phenylbenzamide (Compound No.1-103) Synthesis of

0.42 g of 3-amino-N- (2-ethyl-4-heptafluoroisopropyl-6-methyl) phenylbenzamide and 0.18 g of N- (2-fluoroethyl) -N-methyloxamic acid and 2-chloro- 0.31 g of 1-methylpyridinium iodide was suspended in 7 ml of tetrahydrofuran, 0.51 ml of triethylamine was added thereto, stirred at room temperature for 5 hours, and then the solvent and the like were distilled off from the reaction solution, and then the residue was purified by silica gel column chromatography. Purification with (hexane: ethyl acetate = 1: 1) gave 0.47 g (amorphous) of the compound (No.1-103) shown in Table 1.

¹ H-NMR (CDCl ₃ ), δ ppm: 1.24 (3H, t), 2.36 (3H, s), 2.71 (2H, q), (3.20 + 3.61) (3H, s), (3.77 + 3.84 + 4.22 + 4.28) (2H, t), (4.63 + 4.69 + 4.74 + 4.81) (2H, t), 7.38 (2H, s), 7.49-7.58 (2H, m), 7.71-7.79 (2H, m), (8.26 +8.28) (1H, s), (9.42 + 9.49) (1H, s)

Example 9

3- (N- (2,2,2-trifluoroethyl) -N-methylaminooxalylamino) -N- (2-bromo-4-heptafluoroisopropyl-6-methyl) phenylbenzamide (compound No.1-90) Synthesis

Example 9- (1)

Synthesis of N- (2,2,2-trifluoroethyl) ethoxyoxarylamide

25 g of 2,2,2-trifluoroethylamine was diluted with 150 ml of t-butyl methyl ether, 200 ml of water and 33.6 g of sodium hydrogen carbonate were added thereto, and 24.85 g of ethyl oxyl chloride was stirred under ice-cooling. It diluted with 40 ml and dripped. After completion of the dropwise addition, the reaction solution was separated, the organic layer was washed with dilute hydrochloric acid and saturated brine, dried over magnesium sulfate, t-butyl methyl ether was removed, and N- (2,2,2-trifluoroethyl as the target compound was removed. 40.28 g (yield 80%, crystal) of ethoxyoxarylamide were obtained.

¹ H-NMR (CDCl ₃ ), δ ppm: 1.41 (3H, t), 3.95-4.05 (2H, m), 4.40 (2H, q), 7.42 (1H, br)

Example 9- (2)

Synthesis of N- (2,2,2-trifluoroethyl) -N-methylethoxyoxarylamide

4.48 g of 60% sodium hydride was washed with hexane, suspended in 80 ml of N, N-dimethylformamide, and 20.26 g of N- (2,2,2-trifluoroethyl) ethoxyoxarylamide was added under ice cooling. After completion of foaming, 17.0 g of methyl iodide was diluted with 20 ml of N, N-dimethylformamide and added. After stirring at 50 ° C. for about 2 hours, dilute hydrochloric acid and t-butyl methyl ether were added to the reaction solution, the organic layer was washed with water and brine, dried over magnesium sulfate, and t-butyl methyl ether was distilled off to obtain the target compound. Phosphorus N- (2,2,2-trifluoroethyl) -N-methylethoxyoxarylamide 16.9 g (yield 78%, oily substance) was obtained.

¹ H-NMR (CDCl ₃ ), δ ppm: 1.35-1.42 (3H, m), (3.13 + 3.16) (3H, s), (4.05 + 4.13) (2H, q), 4.33-4.41 (2H, m)

Example 9- (3)

Synthesis of N- (2,2,2-trifluoroethyl) -N-methylaminooxamic acid

16.92 g of N- (2,2,2-trifluoroethyl) -N-methylethoxyoxalylamide was suspended in 20 ml of methanol and 30 ml of water, and 7.00 g of a 50% aqueous sodium hydroxide solution was added dropwise under ice cooling, followed by stirring for 1 hour. . Concentrated hydrochloric acid was added to make the reaction solution acidic, t-butyl methyl ether was added thereto, the mixture was washed with water, the organic layer was washed with water, dried over magnesium sulfate, t-butyl methyl ether was removed, and N- (2,2,2- as the target compound was removed. 11.16 g (yield 80%, solid) of trifluoroethyl) -N-methylaminooxamic acid were obtained.

¹ H-NMR (CDCl ₃ ), δ ppm: (3.22 + 3.50) (3H, s), (4.11 + 4.68) (2H, q)

Example 9- (4) (Scheme 2)

3- (N- (2,2,2-trifluoroethyl) -N-methylaminooxalylamino) -N- (2-bromo-4-heptafluoroisopropyl-6-methyl) phenylbenzamide (compound No.1-90) Synthesis

0.57 g of 3-amino-N- (2-bromo-4-heptafluoroisopropyl-6-methyl) phenylbenzamide and N- (2,2,2-trifluoroethyl) -N-methyloxamic acid 0.26 g and 0.34 g of 2-chloro-1-methylpyridinium iodide were suspended in 6 ml of tetrahydrofuran, 0.55 ml of triethylamine was added and stirred at room temperature overnight, and then the solvent and the like were distilled off from the reaction solution under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to obtain 0.61 g (amorphous) of the compound (No. 1 -90) shown in Table 1.

¹ H-NMR (CDCl ₃ ), δ ppm: 2.43- (3H, s), (3.21 + 3.63) (3H, s), (4.14 + 4.87) (2H, q), 7.49 (1H, s), 7.53- (1H, t), 7.71-7.84 (4H, m), (8.26 + 8.29) (1H, s), (9.38 + 9.49) (1H, s)

Example 10

In the same manner as in Examples 1 to 9, the compound of the present invention was prepared. Although the typical compound of the compound of this invention manufactured by the Example in Table 1 below is described, this invention is not limited to these.

In the table, Me is methyl, Et is ethyl, Pr is propyl, Bu is butyl, "n-" is normal, "t-" is tertiary, "S-" represents a secondary, "i-" represents iso, and "c-" represents cyclo.

In Table 4 below, physical properties obtained by ¹ H-NMR of compounds having amorphous physical properties with the compounds shown in Tables 1 to 3 are shown.

Next, a sanction example is shown. In addition, a part represents a mass part.

Sanction Example 1 Emulsion

Compound of the present invention (10 parts), xylene (60 parts), N-methyl-2-pyrrolidone (20 parts) and sorbol (SORPOL) 3005X (a mixture of nonionic and anionic surfactants, Toho Chemical Industrial Corporation, brand name) (10 parts) was mixed and dissolved uniformly, and the oil agent was obtained.

Preparation Example 2 Hydration-1

Compound (20 parts) of this invention, NIPSIL NS-K (white carbon, Toso Silica Corporation, brand name) (20 parts), kaolin clay (kaolinite, Takehara Chemical Co., Ltd., brand name) (20 parts) , SUNEKIS P-252 (sodium lignin sulfonate, Nippon Paper Chemical Co., Ltd., brand name) (5 parts) and RUNOX P-65L (alkylallyl sulfonate, Toho Chemical Co., Ltd., brand name) (5 Part) was uniformly mixed and ground with an air mill to obtain a hydrating agent.

Sanction Example 3 Hydration-2

Compound of the present invention (20 parts), Nipsil NS-K (20 parts), kaolin clay (50 parts), Renox 1000C (naphthalene sulfonate condensate, Toho Chemical Co., Ltd.) (5 parts) and sorbol 5276 (nonionic surfactant, Toho Chemical Co., Ltd., brand name) (5 parts) was uniformly mixed and ground with an air mill to obtain a hydrating agent.

Sanction Example 4 Solvent (Floor) -1

Disperse the compound of the present invention (20 parts) in propylene glycol (5 parts), sorbol 7933- (Anionic surfactant, Toho Chemical Co., Ltd., brand name) (5 parts) and water (50 parts) mixed in advance The slurry mixture was wet-pulverized with Dinomil (Synmar Enterprises Co., Ltd.), and then xanthan gum (0.2 parts) was mixed and dispersed well in water (19.8 parts) in advance. Was added to obtain a sol (floable).

Sanction Example 5 Solvent (Floor) -2

Compound (20 parts) of the present invention, NEWKALGEN FS-26 (mixture of dioctylsulfo succinate and polyoxyethylene tristyryl phenyl ether, Takemoto fat and oil company, brand name) (5 parts), propylene glycol ( 8 parts) and water (50 parts) were mixed in advance, and this slurry-like mixture was wet-pulverized with dynomil (Shinmar Enterprise Co., Ltd.). Next, xanthan gum (0.2 parts) was mixed and dispersed well in water (16.8 parts) to prepare a gelled product, and the mixture was sufficiently mixed with the pulverized slurry to obtain a sol (floable).

Next, the effect and usefulness of the compound of this invention are demonstrated to an Example concretely.

Test Example 1 Insecticidal Effects on the Larvae of Plutella xylostella

Seeds of Chinese cabbage were sown in Ghipot for three weeks. To the leaves of the plants planted in this pot, water dilution liquid of the emulsion prepared according to Preparation Example 1 was sufficiently sprayed on the foliage to the foliage using an airbrush (one concentration, one repetition). After the chemical liquid was air dried, it was kept in a constant temperature room at 25 ° C., and 5 days after the insect repellent, the death and death of the larvae were examined, and the insecticidal rate (%) was determined using the worms with pain. In addition, the compound A and B of Unexamined-Japanese-Patent No. 2006-306771 (patent document 25) were used as a comparative compound.

As a result of the test, Compound No. 1-1, 1-3-3, 1-9-19, 1-21-57, 1-59-60, 1-62, 1-64-67, 1 of this invention -69 to 71, 1 to 73 to 78, 1 to 80, 1 to 83 to 105, 1 to 109, 1 to 111 to 116, 2 to 3, 2 to 13 to 18 and 3 to 4 to 5 compounds Showed a pesticide rate of 100% at a concentration of 500 ppm. On the other hand, Comparative Compounds A and B did not all exhibit pesticidal activity.

In addition, when the low concentration test was conducted, the compounds No. 1 to 4 to 7, 1 to 9 to 13, 1 to 19, 1 to 21 to 28, 1 to 30, 1 to 32 to 33, and 1 to 35 of the present invention 45, 1-47, 1-49-51, 1-53, 1-56-57, 1-59-60, 1-62, 1-64-67, 1-69-71, 1-73-78, The compounds of 1-83, 1-85-97, 1-99-105, 1-109, 1-112, 1-114-116, 2-1-3, 2-13-18, and 3-4-5 At a concentration of 50 ppm, the insecticidal rate was 100%.

Moreover, when the low concentration test was done at 12.5 ppm or 5 ppm, the compound No.1-45, 1-62, 1-64-65, 1-69-71, 1-88-94, 1-96, of this invention 1-99 to 101, 1 to 103 to 105, 1 to 109, 1 to 112, 1 to 114 to 116, 2 to 3, 2 to 13 to 18, and 3 to 4 compounds of 100% at a concentration of 12.5 ppm Pesticide rate was shown. Compounds of the present invention Nos. 1-22 to 25, 1-28, 1-37 to 38, 1-44, 1-57, 1-59 to 60, 1-75, and 1 to 86 to 87 are compounds of 5 ppm. Insect rate of 100% was shown at the concentration.

Test Example 2: Killing insect test for spotted mite (Tetranychus urticae)

A 430 ml polyethylene cup filled with water was used as a lid with a hole (about 5 mm in diameter) in the center. A rectangular piece of cutout having a width of about 5 mm was placed in a circular filter paper having a diameter of 6.5 cm, and the bottom portion was placed so as to be submerged in water in the cup from the hole of the lid, and a cotton wool was placed on the filter paper. In this way, two leaf disks (2 cm x 5 cm) made from kidney beans herbaceous leaves were placed on cotton wool in which the water in the cup was always supplied, and the adult females were spotted on the leaf disks. Marie was inoculated. The cup was placed in an acrylic cylinder having a height of 50 cm and a diameter of 10 cm, and the water dilution liquid of the emulsion prepared according to Preparation Example 1 was sprayed with 1.35 ml per cup using an airbrush (1 concentration, 1 repetition). After spraying, the mixture was kept in a constant temperature chamber at 25 ° C. Four days after the treatment, the mortality and pain of the adult were examined under a binocular, and the percentage of fertilization (%) was determined using the worms with pain. In addition, the compound A and B of Unexamined-Japanese-Patent No. 2006-306771 were used as a comparative compound.

As a result of the said test, the compound No.1-21-23, 1-26-28, 1-37-47, 1-49-50, 1-56-57, 1-59-60, 1-64 of this invention -65, 1-69-71, 1-74, 1-78, 1-86-97, 1-100-101, 1-103-105, 1-109, 1-112, 1-114-116, 2 Compounds of -1 to 3 and 2 to 13 to 18 exhibited 100% killing rate at a concentration of 50 ppm. On the other hand, Comparative Compounds A and B did not show pesticidal activity.

Moreover, when the low concentration test was done at 12.5 ppm or 5 ppm, the compound No.1-46, 1-50, 1-64-65, 1-69-71, 1-88-94, 1-96, of this invention The compounds of 1-100, 1-103, 1-109, 1-115-116, 2-1-3, and 2-13-18 showed a killing rate of 100% at a concentration of 12.5 ppm. Compounds No. 1-28, 1-40, 1-44, and 1-86 to 87 of the present invention showed 100% killing rate at a concentration of 5 ppm.

Test example 3: Insecticidal effect on larvae of peach black aphid

Three peach black aphid adults were inoculated on the leaves of Chinese cabbage cut to 3 cm × 4 cm and incubated for 48 hours in a constant temperature room at 25 ° C. After the adult was removed, the leaves were immersed in a water dilution liquid of an emulsion prepared according to Preparation Example 1 for 5 seconds, and kept in a constant temperature chamber at 25 ° C. On the 7th day after the treatment, the death and death of the nymphs were examined, and the insecticidal rate (%) was determined using the worms with pain. In addition, the compound A and B of Unexamined-Japanese-Patent No. 2006-306771 were used as a comparative compound.

As a result of the said test, the compound No.1-21, 1-24, 1-28, 1-33, 1-37-42, 1-44, 1-47, 1-56-57, 1-64 of this invention 50 ppm of the compound of -65, 1-69-71, 1-87, 1-89-96, 1-103-104, 1-109, 1-115-116, 2-2-3, 2-13-18 A pesticide rate of 100% was shown at the concentration of. On the other hand, Comparative Compounds A and B did not show pesticidal activity.

Further, when a low concentration test was conducted at 12.5 ppm or 5 ppm, Compound Nos. 1-65, 1-69-71, 1-89-94, 1-97, 1-103, 104, 1-109, The compounds of 1-115, 2-2, 2-15, and 1-17 to 18 exhibited a pesticide rate of 100% at a concentration of 12.5 ppm. Compounds Nos. 1 to 38 to 39 and 1 to 87 of the present invention exhibited a pesticide rate of 100% at a concentration of 5 ppm.

Claims (8)

Formula [1],

(Wherein, R ¹ and R ² are, each independently, a hydrogen atom, C ₁ ~C ₃ alkoxy group, C ₁ ~C ₃ haloalkoxy group, a halogen atom or a C ₁ ~C ₅ represents an alkyl group,
R ³ and R ⁴ are each independently a hydrogen atom, a C ₁ -C ₈ alkyl group, a C ₁ -C ₈ haloalkyl group, an allyl group, a C ₃ -C ₈ cycloalkyl group or a C ₃ -C ₆ cycloalkyl C _1- Or a C ₄ alkyl group, or R ³ and R ⁴ may be bonded to each other to form a C ₃ to C ₈ alkylene bond,
R ⁵ represents a C _{1 to} C ₅ haloalkyl group,
R ⁶ and R ⁷ each independently represent a hydrogen atom, a C ₁ -C ₅ alkyl group, a C ₃ -C ₈ cycloalkyl group, a C ₁ -C ₅ haloalkyl group, a C ₁ -C ₃ alkoxy C ₁ -C ₄ alkyl group, C ₂ ~C ₆ alkenyl, C ₂ ~C ₆ haloalkenyl group, C ₁ ~C ₄ alkyl group, C ₁ ~C ₄ haloalkyl group, C ₁ ~C ₄ alkylsulfonyl group, C ₁ ~C ₄ haloalkylsulfonyl A silyl group, a C _{1 to} C ₃ alkoxycarbonyl group or a C _{1 to} C ₃ haloalkoxycarbonyl group,
Y each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C ₁ -C ₅ alkyl group, a C ₁ -C ₅ haloalkyl group, a C ₁ -C ₃ alkylamino group, a diC ₁ -C _{A 3} alkylamino group, a C _{1 to} C ₃ alkoxy group or a C _{1 to} C ₃ haloalkoxy group,
Z is independently a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a C ₁ -C ₅ alkyl group, a C ₁ -C ₅ haloalkyl group, a C ₁ -C ₃ alkoxy group or a C ₁ -C ₃ Represents a haloalkoxy group,
n represents an integer of 0 to 4, and m represents an integer of 0 to 2). The 3-aminooxalylaminobenzamide derivative characterized by the above-mentioned. The method according to claim 1, wherein in the formula [1],
R ¹ and R ² each independently represent a C ₁ -C ₃ alkoxy group, a C ₁ -C ₃ haloalkoxy group, a halogen atom or a C ₁ -C ₅ alkyl group,
R ³ and R ⁴ are each independently a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, an allyl group, a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ cycloalkyl C _1- Or a C ₄ alkyl group, or R ³ and R ⁴ may be bonded to each other to form a C ₃ to C ₆ alkylene bond,
R ⁵ represents a C _{1 to} C ₅ haloalkyl group,
R ⁶ and R ⁷ each independently represent a hydrogen atom and a C _{1 to} C ₅ alkyl group,
Each independently represents a hydrogen atom, a halogen atom, a cyano group, a C ₁ -C ₃ alkyl group or a C ₁ -C ₃ haloalkyl group,
Z each independently represents a hydrogen atom, a halogen atom or a C _{1 to} C ₃ alkyl group,
n represents the integer of 0-4, m represents the integer of 0-2, The 3-aminooxarylyl benzamide derivative | guide_body. A compound according to claim 2, wherein in formula [1], R ¹ is a methoxy group, a trifluoromethoxy group, a methyl group, an ethyl group or an isopropyl group, and R ² is a chlorine atom, a bromine atom, an iodine atom, a methyl group or 3-aminooxalylaminobenzamide derivative which is an ethyl group. The compound according to claim 2, wherein in Formula [1], R ³ is a methyl group or an ethyl group, R ⁴ is a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, an allyl group, or C ₃ -C ₆ cycloalkyl group or a C ₃ ~C ₆ cycloalkyl, C ₁ ~C ₄ alkyl group, or represent, R ³ and R ⁴ are interconnected to form a C ₃ ~C ₆ alkylene bond good 3-amino-oxalyl-amino-benzamide derivative . As a method for producing the compound of claim 1,
Equation [4],

(Wherein R ¹ , R ² , R ⁵ , R ⁶ , R ⁷ , n, m, Y and Z are as defined in claim 1, and R ⁸ is alkyl having 1 to 5 carbons.)
Compound represented by,
Equation [5],

(Wherein R ³ and R ⁴ are as defined in claim 1). As a method for producing the compound of claim 1,
Equation [3],

(Wherein R ¹ , R ² , R ⁵ , R ⁶ , R ⁷ , n, m, Y and Z are as defined in claim 1).
Compound represented by,
Equation [6],

(Wherein R ³ and R ⁴ are as defined in claim 1).
Reacting with a compound represented by. As a method for producing the compound of claim 1,
Equation [3],

(Wherein R ¹ , R ² , R ⁵ , R ⁶ , R ⁷ , n, m, Y and Z are as defined in claim 1).
Compound represented by,
Equation [7],

(Wherein R ³ and R ⁴ are as defined in claim 1, and X is a halogen atom.)
Reacting with a compound represented by. An insecticide and acaricide comprising the 3-aminooxalylaminobenzamide derivative according to any one of claims 1 to 4 as an active ingredient.