JP2019206478A - 3h-pyrrolopyridine compound and n-oxide, or salts thereof, and horticultural agent containing the compound and use method thereof - Google Patents

Abstract

To provide a novel horticultural agent to solve the problem of still heavy damage from insect pests etc. in crop production in agriculture, gardening etc. and the problem of appearance of insect pests resistant to existing chemicals etc.SOLUTION: There are provided a horticultural agent containing a 3H-pyrrolopyridine compound represented by the general formula (1), wherein A represents a nitrogen atom or a CH group, Rand Rrepresent halogen atom, Rrepresents haloalkyl, R, R, Rand Rrepresent hydrogen atom or haloalkyl group, m represents 1 or 2, and N-oxide, or salts thereof as an active component, and an application thereof.SELECTED DRAWING: None

Description

  The present invention relates to an agricultural and horticultural insecticide containing a certain 3H-pyrrolopyridine compound and N-oxide, or a salt thereof as an active ingredient, and a method of using the same.

  Various compounds have been studied as agricultural and horticultural insecticides, and it has been reported that certain condensed heterocyclic compounds are useful as insecticides (see, for example, Patent Documents 1 to 7). Such a document does not disclose a condensed heterocyclic compound composed of 3H-pyrrolopyridine ring.

JP 2009-280574 A JP 2010-275301 A JP 2011-79774 A JP 2012-131780 A International Publication No. 2012/086848 Pamphlet International Publication No. 2013/018928 Pamphlet International Publication No. 2014/157600 Pamphlet

In crop production such as agriculture and horticulture, damage caused by pests is still large, and the occurrence of pests resistant to existing drugs has become a problem. In addition, the preservation of the global environment is a global issue and is no exception in this field. Therefore, it is desired to develop an agricultural and horticultural insecticide that is novel and has a feature of light environmental burden.

  As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that the 3H-pyrrolopyridine compound represented by the general formula (1) and N-oxide, or salts thereof are excellent for agricultural and horticultural pests. The present application has been completed by finding that it has a control effect and has a light environmental impact (it has little effect on useful insects).

That is, the present invention
[1]
In the formula, R ¹ and R ² may be the same or different, and (a1) a halogen atom; (a2) a cyano group; (a3) (C ₁ -C ₆ ) alkyl group; (a4) (C ₁ -C ₆₎ alkylthio _{group; (a5) (C 1 -C} 6) alkylsulfonyl _{group; (a6) (C 1 -C} 6) alkoxycarbonyl group; or (a7) ^{R 1} and ^{R 2} are bonded to each other, 3 R ³ represents (b1) a hydrogen atom; (b2) a halogen atom; (b3) a (C ₃ -C ₆ ) cycloalkyl group; (b4) A halo (C ₁ -C ₆ ) alkyl group; (b5) a halo (C ₃ -C ₆ ) cycloalkyl group; (b6) a halo (C ₁ -C ₆ ) alkoxy group; (b7) a halo (C ₁ -C ₆₎ (B8) halo (C ₁ -C ₆ ) alkylsulfinyl group; (b9) halo (C ₁ -C ₆ ) alkylsulfonyl group; or (b10) (C ₃ -C ₆ And R ⁴ , R ⁵ , R ⁶ and R ⁷ may be the same or different, and are (c1) a hydrogen atom; (c2) a halogen atom; (c3) and (c3) a cycloalkyl (C ₁ -C ₆ ) alkoxy group; ) Hydroxyl group;
(c4) nitro group; (c5) formyl group; (c6) cyano group; (c7) (C ₁ -C ₆ ) alkyl group; (c8) (C ₂ -C ₆ ) alkenyl group; (c9) (C ₂ -C ₆₎ alkynyl _{group; (c10) (C 3 -C} 6) cycloalkyl group; (c11) _{(C 1} -C ₆₎ alkoxy group; (c12) halo _{(C 1} -C ₆₎ alkyl group; (c13 ) Halo (C ₃ -C ₆ ) cycloalkyl group; (c14) halo (C ₁ -C ₆ ) alkoxy group; (c15) (C ₁ -C ₆ ) alkylthio group; (c16) (C ₁ -C ₆ ) (C17) (C ₁ -C ₆ ) alkylsulfonyl group; (c18) halo (C ₁ -C ₆ ) alkylthio group; (c19) halo (C ₁ -C ₆ ) alkylsulfinyl group; (c20) halo _{(C 1} -C ₆₎ alkylsulfonyl _{group; (c21) (C 3 -C} 6) cycloalkyl _{(C 1} -C ₆₎ alkoxy ^{group; (c22) R 9 (R} 10) Group (wherein, ^{R 9} and ^{R 10} may be the same or different, a hydrogen atom, _{(C 1} -C ₆₎ alkyl group, _{(C 3} -C ₆₎ cycloalkyl _{(C 1} -C ₆₎ alkyl group, A halo (C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) alkylcarbonyl group, a (C ₁ -C ₆ ) alkoxycarbonyl group, or a phenylcarbonyl group);
(c23) R ⁹ (R ¹⁰ ) N carbonyl group; (wherein R ⁹ and R ¹⁰ are the same as above); (c24) carboxyl group; (c25) (C ₁ -C ₆ ) alkoxycarbonyl group; c26) (C ₁ -C ₆ ) alkylcarbonyl group; (c28) C (R ⁹ ) = NOR ¹⁰ group (wherein R ⁹ and R ¹⁰ are the same as above);
(c29) phenyl group; (c30) may be the same or different, and may be the same or different; (a) halogen atom, (b) (C ₁ -C ₆ ) alkyl group, (c) halo (C _1- C ₆ ) alkyl group, (d) (C ₁ -C ₆ ) alkoxy group, (e) halo (C ₁ -C ₆ ) alkoxy group, (f) (C ₁ -C ₆ ) alkylthio group, (g) halo (C ₁ -C ₆ ) alkylthio group, (h) (C ₁ -C ₆ ) alkylsulfinyl group, (i) halo (C ₁ -C ₆ ) alkylsulfinyl group, (j) (C ₁ -C ₆ ) alkyl A phenyl group having 1 to 5 substituents on the ring selected from a sulfonyl group and (k) a halo (C ₁ -C ₆ ) alkylsulfonyl group;
(c31) heterocyclic group; (c32) may be the same or different, and may be the same or different, (a) a halogen atom, (b) (C ₁ -C ₆ ) alkyl group, (c) halo (C ₁ -C ₆₎ alkyl group, (d) _{(C 1} -C ₆₎ alkoxy groups, (e) halo _{(C 1} -C ₆₎ alkoxy groups, (f) _{(C 1} -C ₆₎ alkylthio group, (g) Halo (C ₁ -C ₆ ) alkylthio group, (h) (C ₁ -C ₆ ) alkylsulfinyl group, (i) halo (C ₁ -C ₆ ) alkylsulfinyl group, (j) (C ₁ -C ₆ ) An alkylsulfonyl group, and (k) a heterocyclic group having 1 to 3 substituents selected from a halo (C ₁ -C ₆ ) alkylsulfonyl group on the ring; or A may be the same or different; Represents an atom, N-oxide, or C—R ⁸ group (where R ⁸ represents (d1) a hydrogen atom; or (d2) a halogen atom). m represents 0, 1 or 2. } 3H-pyrrolopyridine compound, N-oxide or a salt thereof,
[2] R ¹ and R ² represent (a1) a halogen atom; R ³ represents (b4) a halo (C ₁ -C ₆ ) alkyl group; and R ⁴ , R ⁵ , R ⁶ and R ⁷ may be the same or different and each represents (c1) a hydrogen atom; (c2) a halogen atom; or (c12) a halo (C ₁ -C ₆ ) alkyl group; and A ¹ and A ² are the same or different It may be a nitrogen atom or a C—R ⁸ group. m represents 1 or 2. } 3H-pyrrolopyridine compound according to [1], or a salt thereof,
Use of the 3H-pyrrolopyridine compound, N-oxide or a salt thereof according to any one of [3] to [2] as an agricultural and horticultural insecticide,
[4] A method for using an agricultural and horticultural insecticide characterized by treating the active ingredient of the agricultural and horticultural insecticide according to [3] to a plant or soil,
[5] A method for controlling agricultural and horticultural pests, which comprises treating an effective amount of the agricultural and horticultural insecticide according to [3] to a plant or soil,
[6] An ectoparasite control agent for animals comprising the 3H-pyrrolopyridine compound, N-oxide or a salt thereof according to any one of claims [1] to [2] as an active ingredient,
[7] A method for controlling ectoparasites, which comprises treating the ectoparasite with an effective amount of the animal ectoparasite control agent according to [6].

  The 3H-pyrrolopyridine compound and N-oxide of the present invention, or salts thereof, not only have an excellent effect as an agricultural and horticultural insecticide, but also parasitize pet animals such as dogs and cats, or domestic animals such as cows and sheep. Also effective against pests.

In the definition of the general formula (1) of the 3H-pyrrolopyridine compound and N-oxide of the present invention, or salts thereof, “halo” means “halogen atom”, and represents chlorine atom, bromine atom, iodine atom, or Indicates a fluorine atom.

“(C ₁ -C ₆ ) alkyl group” means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group Tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, A linear or branched alkyl group having 1 to 6 carbon atoms such as 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group, etc. , the _"(C 2 -C ₆₎ alkenyl group" include vinyl group, allyl group, isopropenyl group, 1-butenyl 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2-propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl A linear or branched alkenyl group having 2 to 6 carbon atoms such as a group, and the “(C ₂ -C ₆ ) alkynyl group” means, for example, an ethynyl group, a 1-propynyl group, a 2-propynyl group 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl-1-propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group , A linear or branched alkynyl group having 2 to 6 carbon atoms such as a 3,3-dimethyl-1-butynyl group.

The “(C ₃ -C ₆ ) cycloalkyl group” means a cyclic alkyl group having 3 to 6 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc., and “(C _1- Examples of the “C ₆ ) alkoxy group” include a methoxy group, an ethoxy group, a normal propoxy group, an isopropoxy group, a normal butoxy group, a secondary butoxy group, a tertiary butoxy group, a normal pentyloxy group, an isopentyloxy group, and a tertiary group. Pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group, 1,1,2-trimethylpropyl group Straight chain or branched chain such as oxy group having 1 to 6 carbon atoms Indicates Kokishi group, as "(C 2 _{-C 6)} alkenyloxy group", for example, propenyloxy group, butenyloxy group, pentenyloxy group, a linear or branched 2 carbon atoms such as a hexenyl group Represents 6 alkenyloxy groups, and examples of the “(C ₂ -C ₆ ) alkynyloxy group” include linear or branched carbon such as propynyloxy group, butynyloxy group, pentynyloxy group, hexynyloxy group, etc. An alkynyloxy group having 2 to 6 atoms is shown.

Examples of the “(C ₁ -C ₆ ) alkylthio group” include a methylthio group, an ethylthio group, a normal propylthio group, an isopropylthio group, a normal butylthio group, a secondary butylthio group, a tertiary butylthio group, and a normal pentylthio group. Group, isopentylthio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normal hexylthio group, isohexylthio group , 1,1,2-trimethylpropylthio group or the like, which is a linear or branched alkylthio group having 1 to 6 carbon atoms, and “(C ₁ -C ₆ ) alkylsulfinyl group” includes, for example, Methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropyl Rufinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1 1 to 6 carbon atoms having a straight or branched chain such as -ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, isohexylsulfinyl group, 1,1,2-trimethylpropylsulfinyl group, etc. an alkyl sulfinyl group, and the "(C 1 _{-C 6)} alkylsulfonyl group", for example, methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylsulfonyl Group, normal butylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1 1-methylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, isohexylsulfonyl group, 1,1,2-trimethylpropylsulfonyl group, etc. An alkylsulfonyl group is shown.

Examples of the “(C ₂ -C ₆ ) alkenylthio group” include straight chain or branched chain alkenylthio having 2 to 6 carbon atoms such as propenylthio group, butenylthio group, pentenylthio group, hexenylthio group and the like. A “(C ₂ -C ₆ ) alkynylthio group” is, for example, a linear or branched carbon atom having 2 to 6 carbon atoms such as propynylthio group, butynylthio group, pentynylthio group, hexynylthio group, etc. An alkynylthio group is shown.

Examples of the “(C ₂ -C ₆ ) alkenylsulfinyl group” include straight chain or branched chain carbon atoms of 2 to 6 carbon atoms such as propenylsulfinyl group, butenylsulfinyl group, pentenylsulfinyl group, hexenylsulfinyl group and the like. Represents an alkenylsulfinyl group, and examples of the “(C ₂ -C ₆ ) alkynylsulfinyl group” include linear or branched chain such as propynylsulfinyl group, butynylsulfinyl group, pentynylsulfinyl group, hexynylsulfinyl group, etc. An alkynylsulfinyl group having 2 to 6 carbon atoms is shown.

As the “(C ₂ -C ₆ ) alkenylsulfonyl group”, for example, a linear or branched carbon atom having 2 to 6 carbon atoms such as a propenylsulfonyl group, a butenylsulfonyl group, a pentenylsulfonyl group, a hexenylsulfonyl group, etc. An alkenylsulfonyl group, and the “(C ₂ -C ₆ ) alkynylsulfonyl group” is, for example, a linear or branched chain such as a propynylsulfonyl group, a butynylsulfonyl group, a pentynylsulfonyl group, a hexynylsulfonyl group, etc. An alkynylsulfonyl group having 2 to 6 carbon atoms is shown.

“(C ₃ -C ₆ ) cycloalkoxy group” means, for example, a cyclic alkoxy group having 3 to 6 carbon atoms such as cyclopropoxy group, cyclobutoxy group, cyclopentyloxy group, cyclohexyloxy group, etc. “(C ₃ -C ₆ ) cycloalkylthio group” means, for example, a cyclic alkylthio group having 3 to 6 carbon atoms such as cyclopropylthio group, cyclobutylthio group, cyclopentylthio group, cyclohexylthio group and the like. , “(C ₃ -C ₆ ) cycloalkylsulfinyl group” means, for example, a cyclic alkylsulfinyl group having 3 to 6 carbon atoms such as cyclopropylsulfinyl group, cyclobutylsulfinyl group, cyclopentylsulfinyl group, cyclohexylsulfinyl group, etc. The group “(C ₃ -C ₆ ) cycloalkylsulfonyl” and Represents, for example, a cyclic alkylsulfonyl group having 3 to 6 carbon atoms such as cyclopropylsulfonyl group, cyclobutylsulfonyl group, cyclopentylsulfonyl group, cyclohexylsulfonyl group and the like.

The “(C ₁ -C ₆ ) alkyl group”, “(C ₂ -C ₆ ) alkenyl group”, “(C ₂ -C ₆ ) alkynyl group”, “(C ₃ -C ₆ ) cycloalkyl group”, “(C ₃ -C ₆ ) cycloalkyloxy group”, “(C ₁ -C ₆ ) alkoxy group”, “(C ₂ -C ₆ ) alkenyloxy group”, “(C ₂ -C ₆ ) alkynyloxy group ”,“ (C ₁ -C ₆ ) alkylthio ”,“ (C ₁ -C ₆ ) alkylsulfinyl ”,“ (C ₁ -C ₆ ) alkylsulfonyl ”,“ (C ₂ -C ₆ ) alkenylthio ” group "," _(C 2 -C ₆₎ alkynylthio group "," _(C 2 -C ₆₎ alkenylsulfinyl group "," _(C 2 -C ₆₎ alkynylsulfinyl group "," _(C 2 _-C 6) alkenylsulfonyl group "," _(C 2 -C ₆₎ A Kinirusuruhoniru group "," _(C 3 -C ₆₎ cycloalkyl group "," _(C 1 -C ₆₎ alkoxy group "," _(C 2 -C ₆₎ alkenyloxy group "," _(C 2 -C ₆ ) Alkynyloxy group ”,“ (C ₃ -C ₆ ) cycloalkylthio group ”,“ (C ₃ -C ₆ ) cycloalkylsulfinyl group ”or“ (C ₃ -C ₆ ) cycloalkylsulfonyl group ” One or two or more halogen atoms may be substituted at the position to be obtained. When two or more halogen atoms are substituted, the halogen atoms may be the same or different.

“Halo (C ₁ -C ₆ ) alkyl”, “Halo (C ₂ -C ₆ ) alkenyl”, “Halo (C ₂ -C ₆ ) alkynyl”, “Halo (C ₃ -C ₆ )” “Cycloalkyl group”, “halo (C ₃ -C ₆ ) cycloalkyloxy group”, “halo (C ₁ -C ₆ ) alkoxy group”, “halo (C ₂ -C ₆ ) alkenyloxy group”, “halo ( “C ₂ -C ₆ ) alkynyloxy group”, “halo (C ₁ -C ₆ ) alkylthio group”, “halo (C ₁ -C ₆ ) alkylsulfinyl group”, “halo (C ₁ -C ₆ ) alkylsulfonyl group” ”,“ Halo (C ₂ -C ₆ ) alkenylthio ”,“ halo (C ₂ -C ₆ ) alkynylthio ”,“ halo (C ₂ -C ₆ ) alkenylsulfinyl ”,“ halo (C _2- C ₆₎ alkynylsulfinyl group " Halo _(C 2 -C ₆₎ alkenyl-sulfonyl group "," halo _(C 2 -C ₆₎ alkynyl-sulfonyl group "," halo _(C 3 -C ₆₎ cycloalkyl group "," halo _(C 1 _-C 6) “Alkoxy group”, “halo (C ₂ -C ₆ ) alkenyloxy group”, “halo (C ₂ -C ₆ ) alkynyloxy group”, “halo (C ₃ -C ₆ ) cycloalkylthio group”, “halo (C ₃ -C ₆ ) cycloalkylsulfinyl group "or" halo (C ₃ -C ₆ ) cycloalkylsulfonyl group ".

Expressions such as “(C ₁ -C ₆ )”, “(C ₂ -C ₆ )”, “(C ₃ -C ₆ )” indicate the range of the number of carbon atoms of various substituents. Further, the above definition can be given for a group to which the above substituent is linked. For example, in the case of “(C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group”, a linear or branched chain It indicates that the alkoxy group having 1 to 6 carbon atoms is bonded to a linear or branched alkyl group having 1 to 6 carbon atoms.

“Heterocyclic group” and “heterocycle” are 5- or 6-membered monocyclic aromatics containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms in addition to carbon atoms as ring-constituting atoms. An aromatic heterocyclic group or a 4- to 6-membered monocyclic non-aromatic heterocyclic group.

  Examples of the “aromatic heterocyclic group” include furyl, thienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, 1,2,4-triazolyl, And monocyclic aromatic heterocyclic groups such as tetrazolyl and triazinyl.

As the “non-aromatic heterocyclic group”, for example,
Oxetanyl, thietanyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, hexamethyleneiminyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, oxazolinyl, thiazolinyl, isoxazolinyl, oxazolyl, oxodiyl-oxodiyl 1-yl, 2-oxo-1,3-oxazolidine-5-yl, 5-oxo-1,2,4-oxadiazoline-3-yl, 1,3-dioxolan-2-yl, 1,3- Dioxane-2-yl, 1,3-dioxepan-2-yl, pyranyl, tetrahydropyranyl, thiopyranyl, tetrahydrothiopyranyl, 1-oxidetetrahydrothiopyranyl, 1,1-dioxide And monocyclic non-aromatic heterocyclic groups such as trahydrothiopyranyl, tetrahydrofuranyl, dioxanyl, pyrazolidinyl, pyrazolinyl, tetrahydropyrimidinyl, dihydrotriazolyl and tetrahydrotriazolyl.

Examples of the 3H-pyrrolopyridine compound and N-oxide represented by the general formula (1) of the present invention or salts thereof include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate, acetate, and fumarate. Acid, maleate, oxalate, methanesulfonate, benzenesulfonate, paratoluenesulfonate and other organic acid salts, sodium ion, potassium ion, calcium ion, trimethylammonium and other inorganic or organic bases And salts thereof.

The 3H-pyrrolopyridine compound and N-oxide represented by the general formula (1) of the present invention and their salts may have one or more asymmetric centers in the structural formula, The above optical isomers and diastereomers may exist, and the present invention includes all the optical isomers and mixtures containing them in an arbitrary ratio. In addition, the compound represented by the general formula (1) of the present invention and N-oxide, or a salt thereof includes two kinds of geometric isomers derived from a carbon-carbon double bond in the structural formula. However, the present invention encompasses all geometric isomers and mixtures containing them in any proportion.

In the 3H-pyrrolopyridine compound and N-oxide represented by the general formula (1) of the present invention, or salts thereof,

The 3H-pyrrolopyridine compound, oxide or salts thereof of the present invention can be produced, for example, by the following production method, but the present invention is not limited to these.

Manufacturing method 1

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , A, and m are the same as described above. ]

Production method of [Step a] The compound represented by the general formula (1) is a 1H-pyrrolopyridine compound produced according to the following intermediate production method or the method described in International Publication No. 2014/157600 pamphlet. (2) can be prepared according to methods described in the literature (Organic Letters, 13 (17), 4498-4501, 2011).

Examples of fluorinating reagents that can be used include N-fluoro-N ′-(chloromethyl) triethylenediamine bis (tetrafluoroborate), Selectflour, (PhSO ₂ ) ₂ NF, and N-fluoropyridinium triflate. , Selectfloor is preferred. The usage-amount of a fluorination reagent is 1-10 molar equivalent normally with respect to 1 mol of compounds (2). If this amount is adjusted, a sulfoxide body can also be produced.

  Bases that can be used include inorganic bases such as sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, cesium carbonate, or triethylamine, pyridine. And amines such as piperidine. The usage-amount of a base is 1-10 molar equivalent normally with respect to 1 mol of compounds (2).

  The organic solvent that can be used in this reaction is not particularly limited as long as it is inert to the reaction. Examples thereof include nitrile solvents such as acetonitrile and benzonitrile, water, and a mixed solvent composed of two or more of these.

  The reaction temperature of this reaction is usually within the range of −20 ° C. to the boiling point of the solvent used. The reaction time is usually several minutes to several tens of hours. After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

The intermediate compound represented by the general formula (2) can be produced by the following method.

Intermediate production method

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁷ , and A are the same as above, X is a leaving group such as a halogen atom, R is 1-phenyl-2-methylpropyl-2- A tertiary alkyl group such as an yl group. ]

Production method of [Step b] represented by the general formula (3-3) produced by Claisen condensation reaction (Org. React. 1942, 1, 266) of 3-ethylthioquinoline-2-carboxylic acid ester and acetate ester The β-ketoester compound and the halogenated nitro compound represented by the general formula (4) are reacted in the presence of a base in an inert solvent to obtain the compound represented by the general formula (3-2). Can be obtained.

The organic solvent that can be used is not particularly limited as long as it is inert to the reaction. For example, ether solvents such as dioxane, 1,2-dimethoxyethane, tetrahydrofuran (THF); aromatic hydrocarbon solvents such as toluene, benzene, xylene; N, N-dimethylformamide, N, N-dimethylacetamide Amide solvents such as N-methylpyrrolidone and mixed solvents composed of two or more of these solvents.

Examples of bases that can be used include inorganic bases such as sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, cesium carbonate, and potassium phosphate. Examples thereof include alkoxides such as potassium t-butoxide, sodium methoxide and sodium ethoxide, alkali metal hydrides such as sodium hydride and potassium hydride, and amines such as triethylamine, pyridine and piperidine. The usage-amount of a base is 1-10 molar equivalent normally with respect to 1 mol of compounds (3-3).

Since this reaction is an equimolar reaction, the compound (3-3) and the compound (4) may be used in an equimolar amount, either of which may be used in excess.
The reaction temperature is usually within the range of room temperature to the boiling point of the solvent used. The reaction time is usually several minutes to several tens of hours. The reaction is preferably carried out in an inert gas atmosphere. After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

Production method of [Step c] A compound represented by general formula (3-1) can be produced by treating a compound represented by general formula (3-2) with an acid in the presence or absence of a solvent. Can do.

Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid, sulfuric acid and nitric acid, organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid and benzoic acid, sulfones such as methanesulfonic acid and trifluoromethanesulfonic acid. An acid etc. can be illustrated, The usage-amount may be suitably selected from the range of 1 time mole-10 times mole with respect to the ester compound represented by general formula (3-2). In some cases, the acids can be used as a solvent.

  The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction. For example, aromatic hydrocarbons such as benzene, toluene and xylene, halogens such as methylene chloride, chloroform and carbon tetrachloride. Hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, amides such as dimethylformamide and dimethylacetamide, ketones such as acetone and methylethylketone, 1,3-dimethyl-2-imidazolidinone and the like An inert solvent such as a polar solvent can be exemplified, and these inert solvents can be used alone or in admixture of two or more. Moreover, when using the said acids as a solvent, it is not necessary to use a solvent.

The reaction temperature can be from room temperature to the boiling range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be carried out in the range of several minutes to 48 hours.
After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

Production Method of [Step d] This reaction can produce a 1H-pyrrolopyridine compound represented by the general formula (2) from the nitro compound represented by the general formula (3-1) by reduction / dehydration reaction. it can.

As the conditions for the reduction reaction, the conditions for the reduction reaction of the nitro group described in known literature (refer to the Chemical Society of Japan, “New Experimental Chemistry Course”, Volume 15, Oxidation and Reduction II, 1977, Maruzen Co., Ltd.). Can be used.

Examples of the inert solvent that can be used in this reaction include alcohols such as methanol and ethanol, ethers such as tetrahydrofuran and dioxane, organic acids such as formic acid and acetic acid, water, and the like. A solvent can be used individually or in mixture of 2 or more types. Further, an aqueous solution of an acid used as a reducing agent in this reaction can be used as an inert solvent as it is.

Examples of the reducing agent that can be used in this reaction include metal-acids, metal-salts, and the like. Examples of metals include iron, tin, and zinc, and examples of acids include hydrochloric acid and sulfuric acid. Examples of the salts of mineral acids such as acetic acid, organic acids such as acetic acid, etc. include tin chloride and ammonium chloride. Moreover, it is also possible to use these in combination. The amount of the reducing agent to be used is appropriately selected from the range of about 1 to 10 times mol of the metal and about 0.05 to 10 times mol of the acid and salt with respect to the nitro compound represented by the general formula (3-1). And use it. The reaction temperature may be selected from the range of about 0 to 150 ° C., and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to about 48 hours. The reduction reaction can also be performed by a catalytic hydrogenation method in the presence of a catalyst. Examples of the catalyst include palladium carbon. After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system containing the desired product by a conventional method, and purifying by a recrystallization method, a distillation method, a column chromatography method, or the like, if necessary.
Alternatively, [Step c] and [Step d] may be performed continuously.
The 1H-pyrrolopyridine compound represented by the general formula (2) produced by this production method can produce the 3H-pyrrolopyridine compound represented by the general formula (1) by the production method described in the production method 1. it can.

Next, specific examples of the compound of the present invention are shown below. In the following table, Me represents a methyl group, Et represents an ethyl group, c-Pr represents a cyclopropyl group, and Ac represents an acetyl group.
The physical properties indicate melting point (° C.) or ¹ H-NMR.

  The agricultural and horticultural insecticide containing the condensed heterocyclic compound represented by the general formula (1) of the present invention, oxide or a salt thereof as an active ingredient is various agricultural and forestry that harms paddy rice, fruit trees, vegetables, other crops, and flowering plants. Suitable for pest control such as horticulture, stored grain pests, hygiene pests or nematodes.

Examples of the pests or nematodes include the following.
Lepidoptera (Lepidoptera) pests such as Parasa consocia, Redwood (Anomis mesogona), Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, African exotic empties (Spod) (Hyphantria cunea), Awanoiga (Ostrinia furnacalis), Ayayotou (Pseudaletia separata), Iga (Tinea translucens), Igusashinmushiga (Bactra furfuryla), Ichinomoseisari (Parnara guttata), Ina Temui inferens), Brachimia triannulella, Monema flavescens, Iraqusinu Waiba (Trichoplusia ni), Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Males flamingo (Helicoverpa armigera) Phararodonta manleyi, Eumeta japonica, Greater white butterfly (Pieris brassicae), Okareha (Malacosoma neustria testacea), Persimmon stag beetle (Stathmopoda masinissa), Arboretum seum (Cuphodes diospyrosella) Tetramoera schistaceana, yellow swallowtail (Papilio machaon hippocrates), yellow-winged bat (Endoclyta sinensis), red-eared winged moth (Lyonetia prunifoliella), red-eared moth (Pyllonorycter ringoneella), crimma (Cydia) Eucoenogenes aestuosa), Grapeberry moss (Lobesia botrana), Black-backed green moth (Latoia sinica), Black-faced red-eye moth (Euzophera batangensis), Phalonidia mesotypa, Spilosoma imparides pi Moth (Olethreutes mori), webbing clothes moth (Tineola bisselliella), Koumoriga (Endoclyta excrescens), carvings (Nemapogon granellus), Kosukashiba (Synanthedon hector), codling moth (Cydia pomonella), diamondback moth (Plutella xylostella), leaf roller (Cnaphalocrocis medinalis),

Southern pink bowler (Sesamia calamistis), Sankaigaiga (Scirpophaga incertulas), Shibata toga (Pediasia teterrellus), Potato moth (Phthorimaea operculella), Shichihokogaga (Stauropus fagi persimilis), Sirochimoga pod (Etiella ken) , White bats (Palpifer sexnotata), white pods (Spodoptera mauritia), white-spotted green moth (Scirpophaga innotata), white moth (Xestia c-nigrum), white-spotted moth (Spodoptera depravata), niger ella estrus ger prunaria, Clostera anastomosis, Soybean looper (Pseudoplusia includens), Soybean salamander (Matsumuraeses falcana), Tobacco moth (Helicoverpa assulta), Tamanaginu waiba (Autographa nigrisigna), Tamanayaga sperm Adoxophyes orana, Caloptilia theivora, Chamonella (Homona magnanima), Ephestia elutella, Eminota (Eumeta minuscula), Clowna anachoreta, Heliotalia (Sparganothis pilleriana), corn moth (Busseola fusca), wolf moth (Euproctis subflava), tobimon ooedashiku (Biston robustum), tomato fruit worm (Heliothis zea), nakajirositaba (Aedia leucomelas), pear moth (Narosoideus) rumicis, Bucculatrix pyrivorella, Grapholita molesta, Pulerina astaurota, Ectomyelois pyrivorella, Chilo suppressalis, Acropepiopsis sapporenlo Squid (Hellula undalis), Sitotroga cerealella, Spodoptera litura, A kind of leaf moth (Eucosma aporema), Acleris comariana, Scopelodes contractus, Orgyia foal (Orgyia moth) Spodoptera frugiperda, Ostrinia zaguliaevi, Naranga aenescens, Andraca bipunctata, Paranthrene regalis, Grape sparrow (Acosmeryx castanea), Grape leaflet Endopiza viteana), grape hosohamaki (Eupoecillia ambiguella), velvet bean caterpillar (Anticarsia gemmatalis), Hosobahairomaki (Cnephasia cinereipalpana),

Japanese gypsy moth (Lymantria dispar), matsukareha (Dendrolimus spectabilis), pea sinking moth (Leguminivora glycinivorella), peanut moth (Maruca testulalis), peanut moth (Matsumuraeses phaseoli), peanut trout (Omiodes indicate), Midchips fuscocupreanus, Acanthoplusia agnata, Mamba (Bambalina sp.), Carposina niponensis, Conogethes punctiferalis sp. ), Papilio helenus, Monk butterfly (Colias erate poliographus), Monk butterfly (Phalera flavescens), Mons white butterfly (Pieris rapae crucivora), Mons white butterfly (Pieris rapae) ), Yamanoi Scarlet (Acrolepiopsis suzukiella), European corn borer (Ostrinia nubilalis), Mamestra brassicae, Ascotis selenaria, Phtheochroides clandestina, Principal adonis (principal) , Apple kenmon (Triaena intermedia), apple wolfberry (Adoxophyes orana fasciata), apple cocos snail (Grapholita inopinata), apple white-spotted spider (Spilonota ocellana), apple scallop (Spilonota lechriaspis), apple scallop (Illiberis pruni) Argyresthia conjugella, Caloptilia zachrysa, Archips breviplicanus, Anomis flava, Cottonworm (Pectinophora gossypiella), Notarcha deroiadicaia , Fake Tobacco budworm (Heliothis virescens), and Wataringa (Earias cupreoviridis), and the like.

  Examples of the Hemiptera (Hemiptera) pests include, for example, Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, and Trigonotylus coelestialium. Aeschynteles maculatus), red beetle (Creontiades pallidifer), red beetle (Dysdercus cingulatus), red beetle (Chrysomphalus ficus), red beetle (Aonidiella aurantii), arabetemi (Graptopsaltus) Scale insects (Icerya purchasi), green beetle (Piezodorus hybneri), blue beetle (Lagynotomus elongatus), blue beetle (Thaia subrufa), blue beetle (Scotinophara lurida), ibarah ibu aito bira Memushi (Stariodes iwasakii), Aspidiotus destructor, Usylorilygus turtle (Taylorilygus pallidulus), Myzusmumecola, Pseudaulacaspis prunicola, Pyuda sumi tho si phon Stink bugs (Anacanthocoris striicornis), giant beetle turtles (Ectometopterus micantulus), giant beetle bugs (Eysarcoris lewisi), giant pest beetle (Molipteryx fuliginosa), giant leaf beetle (Cicadella vihopis abalone moth) (Saissetia oleate), white fly (Trialeurodes vaporariorum),

Agriahana quercus, Amysia spp. (Lygus spp.), Euceraphis punctipennis, Anaspis kashicola, Coccus pseudomagnoliarum, rus C , Chestnut beetle (Galeatus spinifrons), Chrysanthemum beetle aphid (Macrosiphoniella sanborni), Spotted beetle (Aonidiella citrina), Kusagi beetle (Halyomorpha mista), Kusungbai (Stephanitis fasciicarina), Aeti rio L , Trichoza quercicola, Uhlerites latius, Grapeleaf hopper (Erythroneura comes), Paromius exiguus, Duplaspidiotus claviger Nephotettix nigropictus, Black-headed beetle (Halticiellus insularis), Black-headed beetle (Perkinsiella saccharicida), Black-headed whale (Psylla malivorella), Blue-headed whale (Anomomeura mori) oc Pseudaulacaspis pentagona), Pulvinaria kuwacola, Apolygus lucorum, Togo hemipterus, Toxoptera aurantii, Sac charcharcoc sac charc lucifuga), sugar leafhopper (Numata muiri), San Jose scale insect (Comstockaspis perniciosa), citrus snow scale (Unaspis citri), potato beetle aphid (Aulacorthum solani), white-headed bug (E ysarcoris ventralis), silver leaf whitefly (Bemisia argentifolii), white leafhopper (Cicadella spectra), white beetle (Aspidiotus hederae), red beetle (Liorhyssus hyalinus), calophya nigris, califya nigris Broad bean aphid (Megoura crassicauda),

Radish aphids (Brevicoryne brassicae), soybean aphids (Aphis glycines), beetle leaf beetle (Leptocorisa oratorius), beetle leaf beetle (Nephotettix virescens), beetle aphid (Uroeucon formosanum), tobacco beetle emi (Cyrtopel tis) ), Chacanata scales (Lecanium persicae), Chalocera scales (Parlatoria theae), Pseudaonidia paeoniae, Empoasca onukii, Platia stali, Tulipa aphid ), Tulip mustard aphid (Macrosiphum euphorbiae), Stephanitis pyrioides, horned beetle (Ceroplastes ceriferus), camellia beetle (Parlatoria camelliae), fritillaria Japanese turtle (Apolygus spinolai), Japanese leafhopper (Nephotettix cincticeps), Japanese green bug (Glaucias subpunctatus), sugar beeted turtle (Orthotylus flavosparsus), corn aphid (Rhopalosiphum maidis), corn planta (Peregrinus symbol) lectularius), Psylla abieti, green leafhopper (Nilaparvata lugens), Psylla tobirae,

Sea turtles (Eurydema rugosum), pears (Schizaphis piricola), psylla pyricola, psylla pyricola, Parlatoreopsis pyri, nasigunbai (Stephanitis nashi), pears (Dysmicoccus wistariae) ep , Nasimaru aphids (Sappaphis piri), Falcon radish (Lipaphis erysimi), Nephidella aphid (Neotoxoptera formosana), Huskvila aphid (Rhopalosophum nymphaeae), Barahi ameki (yldiana) alni, white-necked leafhopper (Speusotettix subfusculus), white-necked leafhopper (Alnetoidia alneti), yellow-necked grasshopper (Sogatella panicicola), Adelphocoris lineolatus, red-eared beetle (Dysdercus poecil) us), larvae (Parlatoria ziziphi), tiger beetle (Uhlerites debile), tiger beetle (Laodelphax striatella), tiger beetle (Eurydema pulchrum), tiger beetle (Cletus trigonus), corn wee beetle (Cletus trigonus) (Empoasca sp.), Octopus scales (Coccus hesperidum), scallops (Pachybrachius luridus), stag beetles (Planococcus kraunhiae), stag beetles (Stenotus binotatus), scallops (Macrosteles fascifrons), spotted beetle (Dolycoris baccarum), spotted beetle beetle (Adelphocoris triannulatus), grape aphid (Viteus vitifolii), beetle beetle (Acanthocoris sordidus), beetle octo beetle beetle (Macr opes obnubilus), Cletus punctiger, Riptortus clavatus, potato picilido (Paratrioza cockerelli),

Aphrophora costalis, Lyca disponsi, Lygus saundersi, Crisicoccus pini, Empoasca abietis, Acrotis phi , Markopram (Megacopta punctatissimum), Marsila Hoshi beetle (Eysarcoris guttiger), citrus scale insect (Lepidosaphes beckii), citrus leaf moth (Diaphorina citri), citrus black aphid (Toxoptera citricidus), citrus plank octo citri), citrus white beetle (Aleurocanthus spiniferus), citrus leafworm (Pseudococcus citriculus), citrus leafhopper (Zyginella citri), citrus leafworm (Pulvinaria citricola), citrus leaf moth (Coccus discrepans), Pseudaonidia duplex, Pulvinaria aurantii, Licanium corni, Nezara viridula, Stenodema calcarhops, humpadi ), Wheat aphid (Sitobion akebiae), wheat aphid (Schizaphis graminum), wheat leafhopper (Sorhoanus tritici), wheat wreak beetle aphid (Brachycaudus helichrysi), blue-eared beetle (Carpocoris purpureizu mom) (Hyalopterus pruni), Aphis farinose yanagicola, Metasalis populi, Unaspis yanonensis, Mesohomotoma camphorae, Aphis spirae la), Aphis pomi, Lepidosaphes ulmi, Psylla mali, Heterocordylus flavipes, Myzus malisuctus, Aphidonuguis mali, Apple Examples include the common leafhopper (Orientus ishidai), the apple aphid (Ovatus malicolens), the apple beetle (Eriosoma lanigerum), the ruby weevil (Ceroplastes rubens), and the cotton aphid (Aphis gossypii).

  Coleoptera (Coleoptera) pests include, for example, Xystrocera globosa, Aedes aegypti (Paederus fuscipes), Ahanamuri (Eucetonia roelofsi), Azuki weevil (Callosobruchus chinensis), Arimodokisamizo (Hypera postica), rice weevil (Echinocnemus squameus), rice beetle (Oulema oryzae), rice beetle (Oulema oryzae), rice beetle (Donacia provosti), rice weevil (Lissorhoptrus oryzophilus), mosos euglena (Epilachna varivestis), bean weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), beetle weevil (Involvulus cupreus), cucumber beetle (Aulacophora femoralis), pea weevil (Bruchus pisorum), Epilachna vigintioctomaculata, Carpophilus dimidiatus, Cassida nebulosa, Luperomorpha tunebrosa, Phylolreis larvae Spotted beetle (Aeolesthes chrysothrix), Curculio sikkimensis, Carpophilus hemipterus, Oxycetonia jucunda, Cornroot worms (Diabrotica spp.), Scarlet denim (s) , Tribolium castaneum, Sitophilus oryzae, Palorus subdepressus, Melonlontha japonica, Anoplophora malasiaca, Lep pic s tinotarsa decemlineata),

Southern corn rootworm (Diabrotica undecimpunctata howardi), Sphenophorus venatus, Crioceris quatuordecimpunctata, weevil (Conotrachelus nenuphar), Ceuthorbodonica Tobacco beetles (Lasioderma serricorne), Sitona japonicus, Adoretus tenuimaculatus, Tenebrio molitor, Basilepta balyi, Nigri tris (Chaetocnema concinna), Anomala cuprea, Heptophylla picea, Epilachna vigintioctopunctata, Northern corn root worm (Diabrotica longicornis), Eucetonia pilifera Agriotes spp., Attagenus unicolor japonicus, Japanese horned beetle (Pagria signata), Anomala rufocuprea, Palorus ratzeburgii, Aphitobren laga verbasci), Lyctus brunneus, Tribolium confusum, Medythia nigrobilineata, Xylotrechus pyrrhoderus, Potato-free beetle (Epitrix cucumeris) Pinus beetle (Monochamus alternatus), bean squirrel (Popillia japonica), bean scorpion (Epicauta gorhami), maize wivil (Sitophilus zeamais), peach weevil (Rhynchites heros), callous weevil (Listroderes costiro) ), Ngo pea leaf weevil (Phyllobius armatus), apple weevil (Anthonomus pomorum), Rurihamushi (Linaeidea aenea), and boll weevil (Anthonomus grandis), and the like.

  For example, Culex pipiens pallens, Pepomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae Flies (Hydrellia sasakii), Agromyza oryzae, Rice-spotted leaf flies (Hydrellia griseola), Rice-flies (Hydrellia griseola), Green-bellied fly (Ophiomyia phaseoli), Drosophila (Dacus cucurbitae) Fruit flies (Rhacochlaena japonica), fruit flies (Muscina stabulans), fruit flies such as the fruit fly (Megaselia spiracularis), the giant fly (Clogmia albipunctata), the sand fly moth (Tipula aino), the black fly flies (Phorm regina) , Sinaha Daraka (Anopheles sinensis), radish fly (Hylemya brassicae), soybean sand fly (Asphondylia sp.), Red fly (Delia platura), onion fly (Delia antiqua), European fruit fly (Rhagoletis cerasi), chikaieka cucumber (Culex piens) (Ceratitis capitata), Bradysia agrestis, sugar beetle (Pegomya cunicularia), tomato leaffly (Liriomyza sativae), eggplant leaffly (Liriomyza bryoniae), leaflet (Chromatomyia horticola) (Culex quinquefasciatus), Aedes aegypti, Aedes albopictus, bean leaf fly (Liriomyza trifolii), tomato leaf fly (Liriomyza sativae), citrus fruit fly (Dacus dorsalis), citrus moth D (Sitodiplosis mosellana), Mugikimoguribae (Meromuza nigriventris), Mexican fruit flies (Anastrepha ludens), and apple maggot (Rhagoletis pomonella), and the like.

  Hymenoptera (Hymenoptera) pests include, for example, red ants (Pristomyrmex pungens), antwing bees, Monomorium pharaohnis, Pheidole noda, Athalia rosae, cricket (Dryocosmus kuriphilus), ica , Hornets, sedge bee (Athalia infumata infumata), horned bee (Arge pagana), Japanese bee (Athalia japonica), hachiri (Acromyrmex spp.), Fire ant (Solenopsis spp.), Apple bee (Arge mali) (Ochetellus glaber) and the like.

  Examples of the insects of the order Diptera (Homoptera) include, for example, Homorocoryphus lineosus, Gryllotalpa sp. (Homorocoryphus jezoensis), and Teleogryllus emma.

  Examples of Thrips-like pests include, for example, Selenothrips rubrocinctus; Thrips nigropilosus Leeuwenia pasanii), Limetothrips pasaniae, Citruthrips citri, Haplothrips chinensis, Soybean Thrips (Mycterothrips glycines), Soybean Usiloa Thrips setosus, Scirtothrips dorsalis, Dendrothrips minowai, Thripsrips waii, Thrips tabaio, Thrips tabaio, Thrips tabaci ), Thrips coloratus, Thrips coloratus, Thrips coloratus, Thrips coloratus, Thalis thrips Examples include thrips (Frankliniella lilivora), and Liothrips vaneeckei.

  Examples of mite pests include Leptotrombidium akamushi, Tetranychus ludeni, American dock ticks (Dermacentor variabilis), Tetranychus truncatus, Mite (Ornithonyssus bacoti), Modeki mite Tetranychus viennensis), ticks such as Tetranychus kanzawai, Rickicephalus sanguineus, stag tick (Cheyletus malaccensis), genus terapha, moth D Tick (Dermacentor taiwanicus), Acaphylla theavagrans, Polyphagotarsonemus latus, Tomato mite (Aculops lycopersici), Ornithonyssus sylvairum, Nite spider mite (Tetranychusurticae) Mite (Eriophyes chibaensis), Mite (Sarcoptes scabiei), Mite (Haemaphysalis longicornis), Black-legged tick (Ixodes scapularis), Spinach mite (Tyrophagus similis), Mite (Cheyletus eruditu) moorei), southern spider mite (Brevipuspus tick) ), Apple spider mite (Panonychus ulmi), lone star tic (Amblyomma americanum), and duck spider (Dermanyssus gallinae), Robin mite (Rhyzoglyphus robini), a kind of mite mite (Sancassania sp.) And the like.

  Examples of termite pests include: Amphi Termites (Reticulitermes miyatakei), American termites (Incisitermes minor), Termites (Coptotermes formosanus), Termites (Hodotermopsis japonica), Common termites (Reticulitermes sp.), Epic termites us , Glyptotermes kushimensis, Coptotermes guangzhoensis, Neotermes koshunensis, Glyptotermes kodamai, Glyptotermes satsumen satsumen , Glyptotermes nakajimai, Pericapritermes nitobei, Yamato termite (Reticulitermes speratus) and the like.

  For example, cockroach (Periplaneta fuliginosa), German cockroach (Blattella germanica), Great cockroach (Blatta orientalis), Greater cockroach (Periplaneta brunnea), Greater cockroach (Blattella lituricollis), Nonica plane cockroach (P) (Periplaneta americana) and the like.

  Examples of fleas include human fleas (Pulex irritans), cat fleas (Ctenocephalides felis), and fleas (Ceratophyllus gallinae).

  As nematodes, for example, strawberry nematode (Nothotylenchus acris), rice scallop nematode (Aphelenchoides besseyi), red beetle nematode (Pratylenchus penetrans), red beetle nematode (Meloidogyne hapla), meloidodyne rostochiensis), Javaloid nematode (Meloidogyne javanica), Soybean cyst nematode (Heterodera glycines), Southern nematode nematode (Pratylenchus coffeae), Euglena nematode (Pratylenchus neglectus), and Tylenchus semip.

  Examples of mollusks include Pomacea canaliculata, Achatina fulica, slugs (Meghimatium bilineatum), Lehmannina valentiana, Limax flavus, and Acusta despecta sieb. Is mentioned.

  Moreover, the agricultural and horticultural insecticide of the present invention has a strong insecticidal effect against tomato kibaga (Tuta absoluta) as other pests.

  Examples of animal parasitic ticks that are subject to control include Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, and Temagane tick (Haemaphysali camari) , Tick (Haemaphysalis concinna), tick (Haemaphysalis japonica), tick (Haemaphysalis kitaokai), tick (Haemaphysalis ias), tick (Ixodes ovatus), tick tick (ponio tick) Tick such as Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis, Dermanyssus gallinae, Scarlet mites (Ornithonyssus sylviarum), avian mites, such as Ornithonyssus bursa, Eutrombicula wichmanni, red beetle (Leptotrombidium akamushi), Leptotrombidium fept, L (Leptotrombidium tosa), European tick (Neotrombicula autumnalis), American tsutsugamushi (Eutrombicula alfreddugesi), and Tsutsugamushi (Chelletiella yasguri), vor tsutsu mite (Cheyletiella yasguri), Ticks such as Cheyletiella blakei, Psoroptes cuniculi, Chorioptes bovis, Otodectes cynotis, Sarcoptes sca biei), mite mites such as the caterpillar mite (Notoedres cati), and mite mites such as the dog mite (Demodex canis).

  Other fleas to be controlled include, for example, ectoparasite worms belonging to the order Flea (Siphonaptera), and more specifically, fleas belonging to the family Flea (Pulicidae) and the family Flea (Ceratephyllus). . Examples of fleas belonging to the family flea family include, for example, dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis), human fleas (Pulex irritans), elephant flea (Echidnophaga gallinacea), keops rat flea (Xenopsylla cheopis), Leptopsylla segnis), European mouse minnow (Nosopsyllus fasciatus), and Yamato mouse minnow (Monopsyllus anisus).

  Other ectoparasites to be controlled include bovine lice (Haematopinus eurysternus), foal lice (Haematopinus asini), sheep lice (Dalmalinia ovis), bovine lice (Linognathus vituli), pig lice (Haematopinus suis), hirkeus lice, And lice like head lice (Pediculus capitis), and lice like dog lice (Trichodectes canis), blood-absorbing diptera like Trichodectes canis, Tabanus trigonus, Culicoides schultzei, and Simulium ornatum Examples include pests. In addition, examples of endoparasites include nematodes such as lungworm, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms; Tapeworms such as tapeworms, multi-headed tapeworms, single-banded tapeworms, and multi-banded tapeworms, flukes such as Schistosoma japonicum, and liver fluke, and coccidium, malaria parasite, intestinal granulocyst, toxoplasma And protozoa such as Cryptosporidium.

Useful insects refer to bees such as bees and bumblebees, and aquatic organisms such as daphnia and medaka, and the compound of the present invention is characterized by little influence on the organisms.

  The agricultural and horticultural insecticide containing the condensed heterocyclic compound represented by the general formula (I) or a salt thereof of the present invention as an active ingredient damages paddy field crops, field crops, fruit trees, vegetables, other crops, and florets. It has a remarkable control effect on the pests that it gives, so that it is possible to raise seedlings, paddy fields, fields, fruit trees, vegetables, etc. The desired effects of the agricultural and horticultural insecticide of the present invention can be achieved by treating the seeds such as crops, seeds such as flower buds, paddy water, foliage or soil and other cultivation carriers. Among them, it is treated with seedling soil such as crops and flower buds, planting hole soil at the time of transplantation, plant origin, irrigation water, cultivated water in hydroponics, etc., and the present compound is absorbed from the root through or without soil. Application utilizing the so-called osmotic transfer property by making it a preferable form of use.

  Useful plants to which the agricultural and horticultural insecticide of the present invention can be used are not particularly limited, and examples thereof include cereals (eg, rice, barley, wheat, rye, oats, corn, etc.), beans (soybean, Red beans, broad beans, green beans, green beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, peaches, peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, etc.), leaves and fruit vegetables (cabbage, Tomato, spinach, broccoli, lettuce, onion, green onion (satsuki, parrot), green pepper, eggplant, strawberry, pepper, ladle, leek, etc. , Garlic, sea bream, etc.), crops for processing (crab, hemp, beet, hop, sugar cane, sugar beet, olive, rubber, coffee, tobacco, tea, etc.), Lily (pumpkin, cucumber, watermelon, mushroom, melon, etc.), pasture (orchardgrass, sorghum, timothy, clover, alfalfa, etc.), turf (Korean turf, bentgrass, etc.), fragrance and other crops for viewing (lavender) , Rosemary, thyme, parsley, pepper, ginger, etc.), flower buds (flower, rose, carnation, orchid, tulip, lily, etc.), garden trees (ginkgo, sakura, aoki, etc.) Pine, hiba, cedar, camellia, eucalyptus, etc.).

The “plant” includes HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, cetoxydim and the like. Plants to which resistance to herbicides such as acetyl-CoA carboxylase inhibitors, bromoxynil, dicamba, 2,4-D, etc. are imparted by classical breeding methods or genetic recombination techniques are also included.

  Examples of “plants” that have been given resistance by classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapil. Already on sale. Similarly, there are soybeans that are resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron methyl by classical breeding methods, and are already sold under the trade name STS soybeans. Similarly, SR corn and the like are examples of plants to which tolerance has been imparted to acetyl CoA carboxylase inhibitors such as trione oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods.

Plants to which tolerance to an acetyl CoA carboxylase inhibitor has been imparted are Procedures of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci). USA) 87, 7175-7179 (1990). A mutant acetyl CoA carboxylase resistant to an acetyl CoA carboxylase inhibitor has been reported in Weed Science 53, 728-746 (2005), and the like. Introducing a plant resistant to an acetyl-CoA carboxylase inhibitor by introducing a mutation associated with imparting resistance to a plant or introducing a mutation associated with imparting resistance into a plant acetyl-CoA carboxylase, and further, chimeric plastic technology (Gura T. et al. 1999. Replacing the Genome's Spelling Mistakes. Science 285: 316-318. By introducing site-specific amino acid substitution mutations into the cetyl CoA carboxylase gene, ALS gene, etc., plants resistant to acetyl CoA carboxylase inhibitors, ALS inhibitors, etc. can be created. The agricultural and horticultural insecticides of the invention can be used.

  Furthermore, as toxins expressed in genetically modified plants, insecticidal proteins derived from Bacillus cereus and Bacillus popirie; Insecticidal proteins such as endotoxin, VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Agglutinin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; lysine, corn-RIP, abrin, ruffin, saporin, bryodin, etc. Zome inactivating protein (RIP); Steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitor; HMG-CoA reductase; sodium channel, calcium channel inhibitor, etc. Ion channel inhibitors; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase;

Further, as toxins expressed in such a genetically modified plant, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab or other δ-endotoxin proteins, VIP1, VIP2, VIP3 or VIP3A, etc. Also included are insecticidal protein hybrid toxins, partially defective toxins, and modified toxins. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. In the modified toxin, one or more amino acids of the natural toxin are substituted.
Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878. , WO 03/052073, and the like.

  The toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Hemiptera pests, Diptera pests, Lepidoptera pests, nematodes. The agricultural and horticultural insecticides of the present invention can be used in combination with these techniques or systematized.

The insecticide for agricultural and horticultural use according to the present invention is used as it is to control various pests, or appropriately diluted with water or the like, or suspended in an amount effective for controlling the pests or nematodes. For pests and nematodes occurring in fruit trees, cereals, vegetables, etc., in addition to spraying on the foliage, seed immersion in seeds, seed dressing, calper treatment Etc. Seed treatment, soil all layer mixing, crop application, floor soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dress, rice box treatment, water surface application, etc. It can also be absorbed and used. In addition, it can be used for nutrient solution in nutrient solution (hydroponics) cultivation, smoke, or trunk injection.
Furthermore, the agricultural and horticultural insecticide of the present invention may be used as it is, appropriately diluted with water or the like or suspended in an amount effective for pest control in a place where the occurrence of the pest is predicted. For example, in addition to spraying on stored grain pests, house pests, sanitary pests, forest pests, etc., they can also be used for application to house building materials, smoke, baits, and the like.

Seed treatment methods include, for example, a method in which a liquid or solid preparation is diluted or undiluted and the seed is immersed in a liquid state to infiltrate the drug, a solid preparation or liquid preparation is mixed with the seed, Examples thereof include a method of treating and adhering to the surface of the seed, a method of mixing with an adhesive carrier such as a resin and a polymer and coating the seed, a method of spraying around the seed simultaneously with planting, and the like.
The “seed” for performing the seed treatment means a plant body at the initial stage of cultivation used for the propagation of plants, for example, for seeds, bulbs, tubers, seed buds, stock buds, baskets, bulbs, or cuttings. Mention may be made of plants for vegetative propagation.
The “soil” or “cultivation carrier” of the plant when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. However, any material that can grow plants may be used, and so-called soil, seedling mats, water, etc. may be used. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, high It may be a molecular substance, rock wool, glass wool, wood chip, bark or the like.

As a spraying method for crop foliage, stored grain pests, house pests, hygiene pests, forest pests, etc., dilute liquid preparations such as emulsions and flowables or solid preparations such as wettable powders or granular wettable powders with water as appropriate. , A method of spraying, a method of spraying powder, smoke or the like.
Examples of the application method to the soil include, for example, a method in which a liquid preparation is diluted or not diluted with water and applied to a plant stock or a seedling nursery, etc. A method of spraying to a nursery, etc., a method of spraying powder, wettable powder, granule wettable powder, granule, etc. before sowing or transplanting and mixing with the whole soil, a planting hole, making before planting or planting a plant body Examples thereof include a method of spraying powder, wettable powder, wettable powder, granule, etc. on the strip.

As a method for applying rice to a seedling box, the dosage form may vary depending on the time of application such as application during sowing, greening period, application during transplantation, etc., but agents such as powder, granule wettable powder, granules, etc. Apply by mold. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder or granules, for example, mixed with ground soil, mixed with soil covering, mixed with the entire soil. Simply, the soil and the various preparations may be applied alternately in layers.
As an application method to paddy fields, solid preparations such as jumbo agents, packs, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields. In addition, at the time of rice planting, an appropriate formulation can be sprayed and injected into the soil as it is or mixed with fertilizer. In addition, by using a chemical solution such as an emulsion or flowable as a source of water flowing into a paddy field such as a water inlet or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.

In a field crop, it can be processed to a seed or a cultivation carrier close to a plant body from sowing to raising seedling. In plants that are sown directly in a field, in addition to direct treatment on seeds, treatment on a plant source of a plant being cultivated is suitable. For example, a spray treatment using a granule or a irrigation treatment in a liquid of a drug diluted or not diluted with water can be performed. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow.
As the seeding of the cultivated plant to be transplanted and the treatment of the seedling raising period, in addition to the direct treatment to the seed, the irrigation treatment of the liquid drug or the spraying treatment of the granule to the seedling nursery is preferable. In addition, it is also a preferable treatment that a granule is treated in a planting hole at the time of planting or is mixed with a cultivation carrier in the vicinity of the transplantation site.
The agricultural and horticultural insecticide of the present invention is generally used in a form convenient for use according to a conventional method for agricultural chemical preparations.
That is, the condensed heterocyclic compound represented by the general formula (1) of the present invention or a salt thereof is dissolved in an appropriate inert carrier or, if necessary, together with an auxiliary agent in an appropriate ratio. Separated, suspended, mixed, impregnated, adsorbed or adhered, and formulated into appropriate dosage forms such as suspensions, emulsions, solutions, wettable powders, wettable granules, granules, powders, tablets, packs, etc. And use it.

  The composition (agricultural and horticultural insecticide or animal parasite control agent) of the present invention can contain, in addition to the active ingredient, additive components usually used in agricultural chemical formulations or animal parasite control agents as required. Examples of the additive component include a carrier such as a solid carrier and a liquid carrier, a surfactant, a dispersant, a wetting agent, a binder, a tackifier, a thickener, a colorant, a spreading agent, a spreading agent, and an antifreezing agent. , Anti-caking agents, disintegrants, decomposition inhibitors and the like. In addition, you may use a preservative, a plant piece, etc. for an additional component as needed. These additive components may be used alone or in combination of two or more.

  Examples of the solid carrier include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. , Organic solid carriers such as synthetic silicic acid, synthetic silicate, starch, cellulose, plant powder (eg sawdust, coconut cob, corn cob, tobacco stalk, etc.), plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, urea, An inorganic hollow body, a plastic hollow body, fumed silica (white carbon), etc. are mentioned. These may be used alone or in combination of two or more.

  Examples of the liquid carrier include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin. Alcohols, polyhydric alcohol compounds such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc. Ethers, normal hydrocarbons such as normal paraffin, naphthene, isoparaffin, kerosene, mineral oil, Aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, etc. Esters, lactones such as γ-butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, soybean oil, rapeseed oil, Examples thereof include vegetable oils such as cottonseed oil and castor oil, and water. These may be used alone or in combination of two or more.

  Examples of surfactants used as dispersants and wetting agents include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxyethylene Alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxyalkylene-added acetylene diol, polyoxyethylene ether type silicone, ester type Nonionic surfactants such as silicone, fluorosurfactant, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, alkyl sulfate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl phenyl ether sulfate, polyoxy Ethylene styryl phenyl ether sulfate, alkyl benzene sulfonate, alkyl aryl sulfonate, lignin sulfonate, alkyl sulfate Succinate, naphthalenesulfonate, alkylnaphthalenesulfonate, salt of formalin condensate of naphthalenesulfonic acid, salt of formalin condensate of alkylnaphthalenesulfonic acid, fatty acid salt, polycarboxylate, polyacrylate, N -Anionic surfactants such as methyl-fatty acid sarcosinate, resinate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkylphenyl ether phosphate, laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, Cationic surfactants such as stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, alkylamine salts such as alkyldimethylbenzalkonium chloride, amphoteric interfaces such as amino acid type or betaine type Gender, and the like. These surfactants may be used alone or in combination of two or more.

  Examples of binders and tackifiers include carboxymethylcellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6000 to 20000. Polyethylene glycol, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipid (eg, cephalin, lecithin, etc.) cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, cross-linked polyvinyl pyrrolidone, maleic acid and styrenes A polymer, a (meth) acrylic acid copolymer, a half ester of a polymer comprising a polyhydric alcohol and a dicarboxylic acid anhydride, a water soluble salt of polystyrene sulfonic acid, Emissions, terpene, polyamide resins, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, synthetic resin emulsions, and the like.

  Examples of the thickener include xanthan gum, guar gum, diyutane gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compound, water-soluble polymer such as polysaccharide, high-purity bentonite, fumed silica (fumed Inorganic fine powders such as silica and white carbon.

  Examples of the colorant include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.

  Examples of the antifreezing agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

  Examples of adjuvants for preventing caking and promoting disintegration include polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride copolymer, starch / polyacrylonitrile graft copolymer A polymer etc. are mentioned.

  Examples of the decomposition inhibitor include desiccants such as zeolite, quicklime and magnesium oxide, antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.

Examples of the preservative include potassium sorbate, 1,2-benzothiazolin-3-one, and the like.
Furthermore, functional aids, activity enhancers such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, UV absorbers and other supplements as necessary Agents can also be used.

  The compounding ratio of the active ingredient compound can be adjusted as necessary, and may be used by appropriately selecting from a range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural insecticide of the present invention. In the case of powder, granule, emulsion or wettable powder, 0.01 to 50 parts by weight (0.01 to 50% by weight based on the total weight of the agricultural and horticultural insecticide) is appropriate.

The amount of the agricultural and horticultural insecticide of the present invention depends on various factors such as purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application location, application time, etc. Although it varies, the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 are according to the purpose.
Agricultural and horticultural insecticides of the present invention are pests to be controlled, other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, for the purpose of expanding the appropriate period of control or for reducing the dose. It can also be used by mixing with biological pesticides, etc., and can also be used by mixing with herbicides, plant growth regulators, fertilizers, etc., depending on the usage situation.

Examples of other agricultural and horticultural insecticides, acaricides, and nematicides used for such purposes include:
3,5-xylyl methylcarbamate (XMC), Bacillus thuringienses aizawai, Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses kurstaki, Bacillus thuringienses tenebrionis, Bacillus thuringienses produced crystal protein toxin, BPMC, Bt toxin CPC chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1, 3-dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, actin ), Avermectin-B, amidoflumet, amitraz, alanycarb, aanycarb Aldicarb, aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, Isamidofos, isamidofos, isoxathion, isofenphos, isoprocarb (MIPC), ivermectin, imidaclops, imidacloprid, imidaprolin, imiprotoline (indoxacarb), esfenvalerate, ethiofencarb, ethion, ethiprole, etoxazole, etofenprox, ethoprophos, etrimfos, etrimfos, emamectin ema mectin), emamectin-benzoate, endosulfan, empenthrin,

Oxamyl, oxydemeton-methyl, oxydeprofos (ESP), oxibendazole, oxfendazole, potassium oleate, sodium oleate ( sodium oleate), cadusafos, cartap (cartap), carbaryl (carbary1), carbosulfan, carbofuryl, carbofuryl, gamma-cyhalothrin, xylylcarb, quinalphos , Kinoprene, chinomethionat, cloethocarb, clothianidin, clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfolim, chlorethoxyfos (Chlordimeform), chlordane, black Chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, chlorfenson, ch1orfenvinphos, chlorfluazuron, chlorbenzilate, chlorobenzilate Benzobenzoate, kelsen (dicofol), salithion, cyanophos (CYAP), diafenthiuron, diamidafos, cyantraniliprole, theta-cypermethrin ( theta-cypermethrin, dienochlor, cyenopyrafen, dioxabenzofos, diphenenolan, sigma-cypermethrin, dichlofenthion (ECP), cyclothrin , Dichlorvos (DDVP) Disulfoton, dinotefuryl, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, cyflumetofen, diflovidazinmethrin, cyhexine ), Dimethylvinphos, dimethoate, dimefluthrin, silafluofen, cyromazine, spinetoram, spinosad, spirodiclofen, spirodiclofen (spirodiclofen) spirotetramat), spiromesifen, sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin,

Diazinon, tau-fluvalinate, dazomet, thiacloprid, thiamethoxam, thiamethoxam, thiodicarb, thiocyclam, thiosultap, sodium thiosultap -sodium), thionazin, thiometon, deet, dieldrin, tetrach1orvinphos, tetradifon, tetramethylfluthrin, tetramethrin, Tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, teflubenzuron, demeton-S-methyl, temephos, deltamethrin (delta), deltamethrin (delta) terbufos), tralopyril (tralo pyril), tralomethrin, transfluthrin, triazamate, triazaron, triazuron, trichlamide, trichlorphon: DEP, triflumuron, tolfenpyrad, nared : BRP), nithiazine, nitenpyram, novaluron, noviflumuron, hydroprene, vaniliprole, bamidothion, parathion, parathion-parathion -methyl), halfenprox, halofenozide,

Bistrifluron, bisultap, hydramethylnon, hydroxy propyl starch, binapacryl, bifenazate, bifenthrin, pymetrozine, pyracrofos ( pyraclorfos), pyrafluprole, pyridafenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pyrimifenpy, pirimicarbpy ), Pirimiphos-methy1, pyrethrins, fiproni1, fenazaquin, fenamiphos, fenamiphos, bromopropylate, fenitrothion: MEP, phenoxycarb Fenothiocarb, phenothrin, fenobucarb, fensulfothion, fenthion: MPP, phenthoate: PAP, fenvalerate, fenpyroximate, fenpropatrin (fenpropathrin), fenbendazole, fosthiazate, formetanate, butathiofos, buprofezin, furathiocarb, prallethrin, fluacrypyrim, fluacrypyrim fluazinam, fluazuron, fluensulfone, flucycloxuron, flucythrinate, fluvalinate, flupyrazofos, flufenerim, flufeno Flufenoxuron, flufenzine, flufenprox, fluproxyfen, flubrocythrinate, flubendiamide, flumethrin, flurimfen, Prothiofos, protrifenbute, flonicamid, propaphos, propargite: BPPS, profenofos, profluthrin, propoxur: PHC, bromopropyrate (bromopropylate),

Beta-cyfluthrin, hexaflumuron, hexythiazox, heptenophos, permethrin, benclothiaz, bendiocarb, bensu1tap, benzoxymate benzoximate, benfuracarb, phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet (PMP), polynactins ), Formetanate, formothion, phorate,

Machine oil, malathion, milbemycin, milbemycin-A, milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde , Metaflumizone, methamidophos, metam-ammonium, metam-sodium, methiocarb, methidathion (DMTP), methylisothiocyanate, methylneothiocyanate Decaneamide (methylneodecanamide), methylparathion (methylparathion), methoxadiazone (metoxadiazone), methoxychlor (methoxychlor), methoxyfenozide (methoforuide) (metofluthrin), methoprene (methoprene), metolcarb (metolcarb), melfluthrin (meperfluthrin) hos), monocrotophos, monosultap, lambda-cyhalothrin, ryanodine, lufenuron, resmethrin, lepimectin, rotenone, levamisole hydrochloride (levamisol hydrochloride), fenbutatin oxide, morantel tartarate, methyl bromide, tricyclohexyl tin hydroxide, cyhexatin, calcium cyanamide, calcium polysulfide ), Sulfur, nicotine-sulfate, and the like.

  Examples of agricultural and horticultural fungicides used for the same purpose include aureofungin, azaconazole, azithiram, acipetacs, acibenzolar, acibenzolar-S-methyl. ), Azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam, isothianyl (Isotianil), isovaledione, isopyrazam, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprobenfos, imazalil Iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, uniconazole, uniconazole-P, eclomeole, echlomez Edifenphos, etaconazole, ethaboxam, etirimol, etem, ethoxyquin, etridiazole, enestroburin, epoxiconazole, oxazixyl (Oxadixyl), oxycarboxin, copper-8-quinolinolate, oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole Rufumaru salt (oxpoconazole-fumarate), oxolinic acid (oxolinic acid), octhilinone (octhilinone), Ofurase (ofurace), orysastrobin (orysastrobin),

Metam-sodium, kasugamycin, carbamorph, carpropamid, carbendazim, carboxin, carvone, carvone, quinazamid, quinacetol, quinoxifene (Quinoxyfen), quinomethionate, captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine, cufraneb, cuprobam ), Glyodin, griseofulvin, climbazole, cresol, kresoxim-methyl, clozolinate, clotrimazole, clotrimazole, chl obenthiazone, chloraniformethan, chloranil, chlorquinox, chloropicrin, chlorfenazole, chlorodinitronaphthalene, chlorothalonil, chloroneb ), Zalilamide, salicylanilide, cyazofamid, diethyl pyrocarbonate, dietofencarb, cyclafuramid, diclocymet, diclozoline, dichlozoline Tolazole (diclobutrazol), dichlofluanid, cycloheximide, diclomezine, dichloran, dichlorophen, di Dichlone, disulfiram, ditalimfos, dithianon, diniconazole, diniconazole-M, diniconazole-M, zineb, dinocap, dinocton, dinosulfone dinosulfon, dinoterbon, dinobuton, diopenton, dipyrithione, diphenylamine, difenoconazole, cyflufenamid, diflumetorimole, proflucotorizole Cyprodinil, cyprofuram, cypendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimo Kishisutorobin (dimoxystrobin), methyl bromide (methyl bromide), ziram (ziram), silthiofam (silthiofam),

Streptomycin, spiroxamine, sultropen, sedaxane, zoxamide, dazomet, thiadiazin, thiadinil, thiadifluor, thiabendazole Thioxymid, thiochlorfenphim, thiophanate, thiophanate-methyl, thiophanate, thicyofen, thioquinox, chinomethionat, thiofluzamide, thiram, thiram Decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid (dehydro) acetic acid, tebuconazole, tebufloquin, dodicin, dodine, bisethylenediamine copper complex salt (II) (DBEDC), dodemorph, drazoxolon, tri Azimenol, triadimefon, triazbutil, triazoxide, triamiphos, triarimol, triarimol, trichlamide, tricyclazole, triticonazole, Tridemorph, tributyltin oxide, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolulofluanid (t olclofos-methyl, natamycin, nabam, nitrothal-isopropyl, nitrostyrene, nuarimol, copper nonylphenol sulfonate, halacrinate , Validamycin, valifenalate, harpin protein,

Bixafen, picoxystrobin, picobenzamide, bithionol, bitertanol, hydroxyisoxazole, hydroxyisoxazole-potassium, binapacryl ), Biphenyl, piperalin, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin, pyrazophos, pyrametostrobin, pyriophenone (Pyriofenone), pyridinitrile (pyridinitril), pyrifenox, pyribencarb, pyrimethanil, pyroxychlor, pyroxyfur, pyro Ron (pyroquilon), vinclozolin (vinclozolin),

Famoxadone, fenapanil, fenamidone, fenaminosulf, fenarimol, fenitropan, phenoxanil, ferimzone, ferbam, fentin , Fenpiclonil, fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, phthalide, butiobate (Buthiobate), butylamine, bupirimate, fuberidazole, blasticidin-S, furametpyr, furalaxyl, fluraxyl Pyrim (fluacrypyrim), fluazinam, fluoxastrobin, fluotrimazole, fluopicolide, fluopyram, fluoroimide, furcarbanil, floxapyroxide (Fluxapyroxad), fluquinconazole, fluconazole, furconazole, fluconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianamide, flutolanil, flutolanil, Flutriafol, furfural, furmecyclox, flumetover, flumorph, proquinazid, prochloraz, pro Simidone, prothiocarb, prothioconazole, propamocarb, propiconazole, propineb, furophanate, probenazole, bromuconazole ,

Hexachlorobutadiene, hexaconazole, hexylthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate , Benquinox, penconazole, benzamorf, pencicuron, benzohydroxamic acid, bentaluron, benthiazole, benthiavalicarb- isopropyl), penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl, fosetyl aluminum (fosetyl-Al), polyoxins, Polyoxorim, polycarbamate, folpet, formaldehyde, machine oil, maneb, mancozeb, mandipropamid, microzoline, microbutanyl ( myclobutanil, mildiomycin, milneb, mecarbinzid, metasulfocarb, metazoxolon, metam, metam-sodium, metalaxyl ), Metalaxyl-M, metiram, methyl isothiocyanate, mepthyldinocap, metconazole, metsulfovax, metfuroxam, metmino Strobin, metrafenone, mepanipyrim, mefenoxam, meptyldinocap, mepronil, mebenil, methyl iodide (iodomethane), benzazole, benz Inorganic bactericides such as benzalkonium chloride, basic copper chloride, basic copper sulfate, metallic silver, sodium hypochlorote, Cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate, inorganic sulfur ), Copper sulfate anhydride, nickel dimethyldithiocarbamate, 8- Examples thereof include copper compounds such as hydroxy quinoline copper, zinc sulfate, copper sulfate pentahydrate and the like.

  Similarly, as herbicides, for example, 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2, 4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, aclonifen, azafenidin, acifluorfen, aziprotryne, azimsulfuron, aslam, acetochlor, Atrazine, atraton, anisuron, anilofos, abiglycine, abscisic acid, amicarbazone, amidosulfuron, amitrole, amino Cyclopyrachlor (aminocyclopyrachlor), aminopyralid (aminopyralid), Amibu Gin (amibuzin), Amiprophos-methyl, Ametridione, Ametryn, Alachlor, Allidochlor, Alloxydim, Alorac, Isouron , Isocarbamid, isoxachlortole, isoxapyrifop, isoxaflutole, isoxaben, isoxaben, isocil, isonoruron, isoproturon , Isopropalin, isopolinate, isomethiozin, inabenfide, ipazine, ipfencarbazone, iprymidam, imazaquin, imazapic, imazapic B Imazapyr, imazamethapyr, imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indofura, indofura , Indolebutyric acid, uniconazole-P (uniconazole-P), eglinazine, esprocarb, ethametsulfuron, ethametsulfuron-methyl, ethalluralin , Etiolate, ethichlozate ethyl, ethidimuron, etinofen, ethephon, ethoxysulfuron, ethoxyfen, etnipromide mid, etofumesate, etobenzanid, epronaz, erbon, endothal, oxadiazon, oxadiargyl, oxaziclomefone, oxasulfuron (sulf) , Oxapyrazon, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb,

Cafenstrole, cambendichlor, carbasulam, carfentrazone, carfentrazone-ethyl, carbutilate, carbetamide, carboxazole (Carboxazole), quizalofop, quizalofop-P, quizalofop-ethyl, xylachlor, quinoclamine, quinonamid, quinclorac, quinclorac Quinmerac, cumyluron, cliodinate, glyphosate, glufosinate, glufosinate-P, credazine, clethodim, cloxyfonac , Krodinaho (Clodinafop), clodinafop-propargyl, clotoluron, clopyralid, cloproxydim, cloprop, clobromuron, clofop, clomazone , Chlomethoxyni, Chlomethoxyfen, Clomeprop, Chlorazifop, Chlorazine, Chlorazine, Cloransulam, Chloranocryl, Chloramben, Cloransulam-methyl ), Chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamid, chlortoluron (chlo) rtoluron), chlornitrofen, chlorfenac, chlorfenprop, chlorbufam, chlorflurazole, chlorflurenol, chlorprocarb, chlorprocarb Fam (chlorpropham), chlormequat, chloreturon, chloroxynil, chloroxuron, chloropon,

Saflufenacil, cyanazine, cyanatryn, di-allate, diuron, diethamquat, dicamba, cycluron, cycloate, cycloxydim ), Dicloslam, cyclosulfamuron, dichlorprop, dichlorprop-P, dichlorpenil, diclofop, diclofop-methyl, Dichlormate, dichloralurea, diquat, cisanilide, disul, siduron, dithiopyr, dinitramine, cinidon-ethyl, dinosum dinosam), sinosul Cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl, diphenamid, difenoxuron, diphentenpentene (fen) ), Difenzoquat, cybutryne, cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromid, quat cypermid Gibberellin, simazine, dimexano, dimethachlor, dimethazon, dimethametryn, dimethenamid, simethn, simeton, Mepiperate, dimefuron, cinmethylin, swep, sulglycapin, sulcotrione, sulfallate, sulfentrazone, sulfosulfuron , Sulfometuron, sulfometuron-methyl, secbumeton, sethoxydim, cebuthylazine,

Terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr, thiencarbazone, thiencarbazone-methyl, thiocarbazil, tiocarbazil Thiochlorim, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmethrin, tetrafluron (Tetrafluron), tenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione ), Delelachlor, terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralkoxydim, trialflam, triaziflam (Triasulfuron), tri-allate, trietazine, tricamba, triclopyr, tridiphane, tritac, tritosulfuron, triflusulfuron , Triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, tribenuron-methyl, tribenuron, triben Trifop, trifopsime, trimeturon, naptalam, naproanilide, napropamide, nicosulfuron, nitralin, nitrofen, nitrofluorfen (Nitrofluorfen), nipyraclofen, neburon, norflurazon, noruron,

Barban, paclobutrazol, paraquat, parafluron, haloxydine, haloxyfop, haloxyfop-P, haloxyfop-methyl ), Halosafen, halosulfuron, halosulfuron-methyl, picloram, picolinafen, bicyclopyrone, bispyribac, bispyribac- sodium), pyranon, pinoxaden, bifenox, piperophos, hymexazol, pyraclonil, pyrasulfotole, pyrazoloxyfen, pyrazosulfuron n), pyrazosulfuron-ethyl, pyrazolate, pyranafos, pyraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithio Sodium (pyrithiobac-sodium), pyridate, pyrifalid (pyriftalid), pyributicarb, pyribenzoxim, pyrimisulfan, pyrimisulfuron, pyriminobac-methyl ), Pyroxasulfone, pyroxsulam,

Fenasulam, phenisopham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, Phenothiol, fenoprop, phenobenzuron, fenthiaprop, fenteracol, fentrazamide, phenmedipham, phenmedipham -ethyl), butachlor, butafenacil, butamifos, buthiuron, buthidazole, butate, butylate, buturon, butenachlor, butroxydim, butroxydim, Butralin, flazasulfuron, framprop, furyloxyfen, prynachlor, primisulfuron-methyl, fluazifop, fluazifop-P ( fluazifop-P, fluazifop-butyl, fluazolate, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluoro Fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone-sodium, fluchloralin, flucetosulfuron, fluthiace Fluthiacet, fluthiacet-methyl, flupyrsulfuron, flufenacet, flufenican, flufenpyr, flupropacil, flupropanate , Flupoxam, flumioxazin, full microlac, flumiclorac-pentyl, flumipropyn, flumezin, fluometuron, flumetsulam, flumetsulam, flumetsulam (Fluridone), flurtamone, fluroxypyr,

Pretilachlor, proxan, proglinazine, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propoxahop ( propaquizafop), propachlor, propazine, propanil, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron, propham, Profluazol, profluralin, prohexadione-calcium, propoxycarbazone, propoxycarbazone sodium, propoxydim Bromacil (bromacil), Buromupirazon (brompyrazon), prometryn (prometryn), prometon (prometon), bromoxynil (bromoxynil), bromophenoxy shims (bromofenoxim), bromobutide (bromobutide), Buromoboniru (bromobonil), florasulam (florasulam),

Hexachloroacetone, hexazinone, petoxoxamid, benazolin, penoxsulam, pebulate, beflubutamid, vernolate, perfluidone, bencarbazone, bencarbazone ), Benzadox, benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulide, bensulfuron-methyl, benzoylprop ( benzoylprop), benzobicyclon, benzofenap, benzofluor, benzofluor, bentazone, pentanochlor, benthiocarb, Pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomeamine, foramsulfuron, forchlorfenuron, hydrazide maleate (maleic hydrazide), mecoprop (mecoprop), mecoprop-P (mecoprop-P), mezinoterb (medinoterb), mesosulfuron, mesosulfuron-methyl, mesotrione (mesotrione), mesoprazine (mesoprazine) methoprotryne, metazachlor, methazole, metazosulfuron, metabenzthiazuron, metamitron, metamifop, metam, metal prop Methalpropalin, Methiuron, Methiozolin, Methiobencarb, Methyldymron, Metoxuron, Metosulam, Metosulfuron, Metosulfuron methyl , Metflurazon, metobromuron, metobenzuron, metometon, metolachlor, metribuzin, mepiquat-chloride, mefenacet, mefenacet, mefenacet, mefenacet, mefenacet, mefenacet, mefenacet ), Monalide, monisouron, monuron, monochloroacetic acid, monolinuron, molinate, morfamquat, iodosulfur (Iodosulfuron), iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, linuron, rimsulfuron, lenacil, rhodetanyl (iodosulfuron) rhodethanil), calcium peroxide, methyl bromide and the like.

  Examples of biological pesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect poxvirus (Entomopoxi virus, EPV) ) Virus preparations, Monocrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasturia penetrans, etc. As a microbial pesticide, Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc. use Microbial pesticides, by using mixed such as biological pesticides utilized as herbicides, such as Xanthomonas campestris (Xanthomonas campestris), the same effect can be expected.

  In addition, examples of biological pesticides include Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa seibi tick (Dacnusa seibi tick) persimilis), natural enemy organisms such as Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z) -10-tetradecenyl acetate, (E, Z) ) -4,10-tetradecadinyl acetate, (Z) -8-dodecenyl acetate, (Z) -11-tetradecenyl acetate, (Z) -13-icosen-10-one, 14-methyl-1 -Can be used in combination with pheromone agents such as octadecene .

Hereinafter, the representative compounds of the present invention and production examples of production intermediates will be described in more detail, but the present invention is not limited to these examples.

REFERENCE EXAMPLE 1.3 Preparation of 1,1-dimethyl-2-phenylethyl ester of 6- (6-chloro-3-ethylthio-quinolin-2-yl) -3-oxy-propionic acid
1,1-dimethyl-2-phenylethyl ester of acetic acid (461 mg) was dissolved in THF (10 mL), cooled in a dry-acetone bath under argon, and then lithium diisopropylamide (2.6 m THF solution, 2.2 mL). ) Was added. The mixture was stirred for 15 minutes, and 6-chloro-3-ethylthio-quinoline-2-carboxylic acid ethyl ester (594 mg) synthesized by the method described in the pamphlet of WO2016 / 091731 was added. After stirring for 1 hour, 3N-hydrochloric acid was added and the temperature was raised to room temperature. Water and ethyl acetate are added to the reaction solution, and after extraction, the organic layer is concentrated, the residue is subjected to column chromatography, and the desired 3- (6-chloro-3-ethylthio-quinolin-2-yl) -3 There was obtained 1,1-dimethyl-2-phenylethyl ester (849 mg) of -oxy-propionic acid.
Yield: 96%
Physical properties: ¹ H-NMR (CDCl ₃ ): 7.88 (s, 1H), 7.85 (d, 1H), 7.73 (d, 1H), 7.55 (dd, 1H), 7.21 -7.16 (m, 3H), 7.10-7.08 (m, 2H), 4.17 (s, 2H), 3.02 (dd, 2H), 2.93 (d, 2H), 1.45 (t, 3H), 1.39 (s, 6H)

Reference Example 2.2 Preparation of 2- (6-chloro-3-ethylthio-quinolin-2-yl) -6-trifluoromethyl-pyrrolo [3,2-b] pyridine
3- (6-Chloro-3-ethylthio-quinolin-2-yl) -3-oxy-propionic acid 1,1-dimethyl-2-phenylethyl ester (750 mg) was dissolved in DMF (5 mL) and ice-cooled. Underneath, sodium hydride (136 mg) was added. After stirring for 30 minutes, 2-chloro-3-nitro-5-trifluoromethylpyridine (462 mg) was added and stirred for 2 hours. Water, 3N-hydrochloric acid, and ethyl acetate were sequentially added to the reaction solution. After extraction, the organic layer was concentrated, trifluoroacetic acid (5 mL) was added to the residue, and the mixture was stirred at 50 ° C. for 1 hour. Iron powder (500 mg) was added to the reaction solution, and the mixture was stirred at 80 ° C. for 2 hours. Water and ethyl acetate were added to the reaction solution, and the mixture was filtered through celite. The aqueous layer was extracted with ethyl acetate, the organic layer was concentrated, the residue was subjected to column chromatography, and the desired 2- (6-chloro-3-ethylthio-quinolin-2-yl) -6-trifluoromethyl was obtained. -Pyrrolo [3,2-b] pyridine (446 mg) was obtained.
Physical properties: ¹ H-NMR (CDCl ₃ ): 10.81 (brs, 1H), 8.89 (s, 1H), 8.32 (s, 1H), 8.21 (s, 1H), 8.03 (S, 1H), 8.01 (s, 1H), 7.79 (s, 1H), 7.66 (dd, 1H), 3.14 (dd, 2H), 1.45 (t, 3H)
Yield: 64%

Example 1.2-of (2-ethylthio-4-trifluoromethylphenyl) -3,3-difluoro-6-trifluoromethyl-3H-pyrrolo [3,2-b] pyridine (Compound No. 1-3) Manufacturing method
2- (6-Chloro-3-ethylthio-quinolin-2-yl) -6-trifluoromethyl-pyrrolo [3,2-b] pyridine (173 mg) prepared in Reference Example 2 was dissolved in acetonitrile (10 ml). Water (78 mg) and sodium bicarbonate (181 mg) were sequentially added, and Selectfloor (764 mg) was added under ice cooling, followed by stirring for 2 hours. Water and ethyl acetate were added to the reaction solution, and the organic layer was concentrated and subjected to column chromatography to give 2- (6-chloro-3-ethylsulfonyl-quinolin-2-yl) -3,3-difluoro-6- Trifluoromethyl-pyrrolo [3,2-b] pyridine (47 mg) was obtained.
Physical property: 164-166
Yield: 24%

  Examples of preparations are shown below, but are not limited thereto. In the formulation examples, “parts” means “parts by weight”.

Formulation Example 1
Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixing of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above is uniformly mixed and dissolved to prepare an emulsion.

Formulation Example 2
Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above is mixed and ground uniformly to form a powder.

Formulation Example 3
Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts lignin sulfonate 5 parts The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to give granules.

Formulation Example 4
Compound of the present invention 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts The above is uniformly mixed and ground to obtain a wettable powder.

Next, although the test example of this invention is shown, it is not limited to these. .
Test Example 1
Control value test against peach aphid (Myzus persicae) Chinese cabbage was planted in a plastic pot having a diameter of 8 cm and a height of 8 cm to breed a peach aphid, and the number of parasites in each pot was investigated. The condensed heterocyclic compound represented by the general formula (I) of the present invention or a salt thereof is dispersed in water and diluted to 500 ppm of a chemical solution. The chemical solution is sprayed on the stems and leaves of a potted Chinese cabbage and air-dried. The number of parasites of the peach aphid parasitizing each Chinese cabbage on the 6th day after drug spraying was calculated, the control value was calculated from the following formula, and the determination was made according to the following criteria.

Ta: Number of parasites before spraying in the treated zone T: Number of parasites after spraying in the treated zone Ca: Number of parasites before spraying in the untreated zone C: Number of parasites after spraying in the untreated zone

Judgment criteria A ... 100% control value
B ... Control value 99% ~ 90%
C ... Control value 89% -80%
D ... Control value 79% -50%

As a result, 1-3, 1-6, 1-7, 1-11, 1-44, 1-124, and 1-125 of the compounds of the present invention showed A activity.

Test Example 2 Insecticidal test against Japanese brown planthopper (Laodelphax striatella) The condensed heterocyclic compound represented by the general formula (I) of the present invention or a salt thereof is dispersed in water and diluted to a chemical solution of 500 ppm, and rice seedlings (variety: Nipponbare) are added to the chemical solution. Was soaked for 30 seconds, air-dried, put into a glass test tube, inoculated with 10 each of the 3 Japanese beetles, inoculated with cotton plugs, and after 8 days of inoculation, the number of live and dead insects was investigated. And the determination was made according to the determination criteria of Test Example 1.

As a result, 1-3, 1-6, 1-7, 1-11, 1-44, 1-124, and 1-125 of the compounds of the present invention showed A activity.

Test Example 3 Insecticidal test against Plutella xylostella Sponge seedlings are allowed to lay eggs and lay eggs, and two days after the release, cypress seedlings with spawning eggs are condensed complex represented by the general formula (I) of the present invention The drug containing a ring compound as an active ingredient was immersed in a chemical solution diluted to 500 ppm for about 30 seconds, air-dried, and then allowed to stand in a thermostatic chamber at 25 ° C. Six days after immersion in the chemical solution, the number of hatching insects was investigated, the death rate was calculated according to the following formula, and the determination was made according to the criterion of Test Example 1. 1 ward, 10 heads, 3 systems.

As a result, 1-3, 1-6, 1-7, 1-11, 1-44, 1-124, and 1-125 of the compounds of the present invention showed A activity.

The compound group according to the present invention is a useful agricultural material that has an excellent control effect against a wide range of agricultural and horticultural pests and has little influence on useful organisms.

Claims (7)

{Wherein R ¹ and R ² may be the same or different, (a1) halogen atom; (a2) cyano group; (a3) (C ₁ -C ₆ ) alkyl group; (a4) (C _1- C ₆₎ alkylthio _{group; (a5) (C 1 -C} 6) alkylsulfonyl _{group; (a6) (C 1 -C} 6) alkoxycarbonyl group; or (a7) ^{R 1} and ^{R 2} are bonded to each other, Can also form 3-6 membered aliphatic rings,
R ³ is (b1) a hydrogen atom; (b2) a halogen atom; (b3) a (C ₃ -C ₆ ) cycloalkyl group; (b4) a halo (C ₁ -C ₆ ) alkyl group; (b5) a halo (C ₃ -C ₆₎ cycloalkyl; (b6) halo _{(C 1} -C ₆₎ alkoxy group; (b7) halo _(C 1 -C ₆₎ alkylthio group; (b8) halo _(C 1 -C ₆₎ alkylsulfinyl A group; (b9) a halo (C ₁ -C ₆ ) alkylsulfonyl group; or (b10) (C ₃ -C ₆ ) cycloalkyl (C ₁ -C ₆ ) alkoxy group; and R ⁴ , R ⁵ , R ⁶ and R ⁷ may be the same or different, and (c1) a hydrogen atom; (c2) a halogen atom; (c3) a hydroxyl group;
(c4) nitro group; (c5) formyl group; (c6) cyano group; (c7) (C ₁ -C ₆ ) alkyl group; (c8) (C ₂ -C ₆ ) alkenyl group; (c9) (C ₂ -C ₆₎ alkynyl _{group; (c10) (C 3 -C} 6) cycloalkyl group; (c11) _{(C 1} -C ₆₎ alkoxy group; (c12) halo _{(C 1} -C ₆₎ alkyl group; (c13 ) Halo (C ₃ -C ₆ ) cycloalkyl group; (c14) halo (C ₁ -C ₆ ) alkoxy group; (c15) (C ₁ -C ₆ ) alkylthio group; (c16) (C ₁ -C ₆ ) (C17) (C ₁ -C ₆ ) alkylsulfonyl group; (c18) halo (C ₁ -C ₆ ) alkylthio group; (c19) halo (C ₁ -C ₆ ) alkylsulfinyl group; (c20) halo _{(C 1} -C ₆₎ alkylsulfonyl _{group; (c21) (C 3 -C} 6) cycloalkyl _{(C 1} -C ₆₎ alkoxy ^{group; (c22) R 9 (R} 10) Group (wherein, ^{R 9} and ^{R 10} may be the same or different, a hydrogen atom, _{(C 1} -C ₆₎ alkyl group, _{(C 3} -C ₆₎ cycloalkyl _{(C 1} -C ₆₎ alkyl group, A halo (C ₁ -C ₆ ) alkyl group, a (C ₁ -C ₆ ) alkylcarbonyl group, a (C ₁ -C ₆ ) alkoxycarbonyl group, or a phenylcarbonyl group);
(c23) R ⁹ (R ¹⁰ ) N carbonyl group; (wherein R ⁹ and R ¹⁰ are the same as above); (c24) carboxyl group; (c25) (C ₁ -C ₆ ) alkoxycarbonyl group; c26) (C ₁ -C ₆ ) alkylcarbonyl group; (c28) C (R ⁹ ) = NOR ¹⁰ group (wherein R ⁹ and R ¹⁰ are the same as above);
(c29) phenyl group; (c30) may be the same or different, and may be the same or different; (a) halogen atom, (b) (C ₁ -C ₆ ) alkyl group, (c) halo (C _1- C ₆ ) alkyl group, (d) (C ₁ -C ₆ ) alkoxy group, (e) halo (C ₁ -C ₆ ) alkoxy group, (f) (C ₁ -C ₆ ) alkylthio group, (g) halo (C ₁ -C ₆ ) alkylthio group, (h) (C ₁ -C ₆ ) alkylsulfinyl group, (i) halo (C ₁ -C ₆ ) alkylsulfinyl group, (j) (C ₁ -C ₆ ) alkyl A phenyl group having 1 to 5 substituents on the ring selected from a sulfonyl group and (k) a halo (C ₁ -C ₆ ) alkylsulfonyl group;
(c31) heterocyclic group; (c32) may be the same or different, and may be the same or different, (a) a halogen atom, (b) (C ₁ -C ₆ ) alkyl group, (c) halo (C ₁ -C ₆₎ alkyl group, (d) _{(C 1} -C ₆₎ alkoxy groups, (e) halo _{(C 1} -C ₆₎ alkoxy groups, (f) _{(C 1} -C ₆₎ alkylthio group, (g) Halo (C ₁ -C ₆ ) alkylthio group, (h) (C ₁ -C ₆ ) alkylsulfinyl group, (i) halo (C ₁ -C ₆ ) alkylsulfinyl group, (j) (C ₁ -C ₆ ) An alkylsulfonyl group, and (k) a heterocyclic group having 1 to 3 substituents selected from a halo (C ₁ -C ₆ ) alkylsulfonyl group on the ring; or A may be the same or different; Represents an atom, N-oxide, or C—R ⁸ group (where R ⁸ represents (d1) a hydrogen atom; or (d2) a halogen atom). m represents 0, 1 or 2. } 3H-pyrrolopyridine compound, N-oxide or a salt thereof represented by: R ¹ and R ² represent (a1) a halogen atom; R ³ represents (b4) a halo (C ₁ -C ₆ ) alkyl group; and R ⁴ , R ⁵ , R ⁶ and R ⁷ are which may be identical or different, (c1) a hydrogen atom; (c2) a halogen atom; or (c12) halo (C ₁ -C ₆₎ alkyl group; indicates, a ¹ and a ^2, which may be the same or different , A nitrogen atom, or a C—R ⁸ group. m represents 1 or 2. } The 3H-pyrrolopyridine compound of Claim 1 represented by these, or its salt.   Use of the 3H-pyrrolopyridine compound, N-oxide or a salt thereof according to any one of claims 1 to 2 as an agricultural and horticultural insecticide.   A method for using an agricultural and horticultural insecticide, which comprises treating an active ingredient of the agricultural and horticultural insecticide according to claim 3 to a plant or soil.   A method for controlling agricultural and horticultural pests, which comprises treating an effective amount of the agricultural and horticultural insecticide according to claim 3 with plants or soil.   An animal ectoparasite control agent comprising the 3H-pyrrolopyridine compound, N-oxide or a salt thereof according to any one of claims 1 to 2 as an active ingredient.   A method for controlling ectoparasites, comprising treating the ectoparasites with an effective amount of the animal ectoparasite control agent according to claim 6.