WO2018105632A1 - Quinoline compound having carbamate group, salt of same, insecticide for agricultural and horticultural use containing said compound, and use of said insecticide - Google Patents

Abstract

The present invention addresses the problem of developing and providing a novel insecticide for agricultural and horticultural use since pests still cause extensive damage on the production of agricultural and horticultural crops and pests that are resistant to conventional chemicals have emerged. The present invention provides a quinoline compound having a carbamate group represented by general formula (1) (wherein R¹ represents an alkyl group; R² represents a hydrogen atom or an alkyl group; R³ represents a haloalkyl group; A¹ represents an oxygen atom or an N-Me group; A¹ represents a nitrogen atom; A² represents CH; m is 2; and n is 1) or a salt thereof; an insecticide for agricultural and horticultural use, which contains the compound or a salt thereof as an active ingredient; and a use of the insecticide for agricultural and horticultural use.

Description

Quinoline compounds having carbamate groups, or salts thereof, agricultural and horticultural insecticides containing the compounds, and methods of use thereof

The present invention relates to an agricultural and horticultural insecticide containing a quinoline compound having a carbamate group or a salt thereof as an active ingredient, and a method of using the same.

So far, various compounds have been studied as agricultural and horticultural insecticides, and certain condensed heterocyclic compounds have been reported to be useful as insecticides (see, for example, Patent Documents 1 to 8). Such documents do not disclose any quinoline compounds having a carbamate group.

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. 2015/121136 Pamphlet International Publication No. 2016/091731 Pamphlet

In crop production such as agriculture and horticulture, damage caused by pests is still large, and development of new agricultural and horticultural insecticides is desired due to factors such as the generation of resistant pests against existing drugs.

As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that the quinoline compound having a carbamate group represented by the general formula (1) or a salt thereof has an excellent control effect against agricultural and horticultural pests. At the same time, the present inventors have found that it is environmentally degradable and has little influence on environmental organisms such as bees.
That is, the present invention
[1] General formula (1)

{Wherein R ¹ is (a1) (C ₁ -C ₆ ) alkyl group; (a2) halo (C ₁ -C ₆ ) alkyl group; (a3) (C ₂ -C ₆ ) alkenyl group; (a4 ) _{(C 2} -C ₆₎ alkynyl group; _{and; (a5) (C 3 -C} 6) cycloalkyl group; or _{(a6) (C 3 -C 6} ) cycloalkyl _{(C 1} -C ₆₎ alkyl group .
R ² represents (b1) a hydrogen atom; (b2) a (C ₁ -C ₆ ) alkyl group; (b3) a halo (C ₁ -C ₆ ) alkyl group; (b4) (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆₎ alkyl group; (b5) cyano _{(C 1} -C ₆₎ alkyl _{group; (b6) (C 3 -C} 6) cycloalkyl group; or _{(b7) (C 3 -C 6} ) cycloalkyl ( C ₁ -C ₆ ) alkyl group;
R ³ is (c1) halogen atom; (c2) cyano group; (c3) nitro group; (c4) (C ₁ -C ₆ ) alkyl group; (c5) (C ₁ -C ₆ ) alkoxy group; ) (C ₂ -C ₆ ) alkenyloxy group; (c7) (C ₂ -C ₆ ) alkynyloxy group; (c8) halo (C ₁ -C ₆ ) alkyl group; (c9) halo (C ₁ -C ₆₎ (C10) halo (C ₂ -C ₆ ) alkenyloxy group; (c11) halo (C ₂ -C ₆ ) alkynyloxy group; (c12) (C ₁ -C ₆ ) alkylthio group; (c13) (C ₁ -C ₆ ) alkylsulfinyl group; (c14) (C ₁ -C ₆ ) alkylsulfonyl group; (c15) halo (C ₁ -C ₆ ) alkylthio group; (c16) halo (C ₁ -C ₆ ) An alkylsulfinyl group; or (d17) a halo (C ₁ -C ₆ ) alkylsulfonyl group.
A represents an oxygen atom or N—R ⁴ (wherein R ⁴ represents (e1) a hydrogen atom; or (e2) (C ₁ -C ₆ ) an alkyl group); and A ¹ and A ² may be the same or different and each represents CH or a nitrogen atom, m represents 0, 1, or 2, and n represents 0, 1, or 2. } A quinoline compound or a salt thereof,
[2] The quinoline compound or a salt thereof according to [1], wherein A is an oxygen atom,
[3] The quinoline compound or a salt thereof according to [1], wherein A is N-Me,
[4] An agricultural and horticultural insecticide comprising the quinoline compound or a salt thereof according to any one of [1] to [3] as an active ingredient,
[5] A method for using an agricultural and horticultural insecticide characterized by treating a plant or soil with an effective amount of the quinoline compound or salt thereof according to any one of [1] to [3],
[6] An ectoparasite control agent for animals comprising the quinoline compound or a salt thereof according to any one of [1] to [3] as an active ingredient.

The quinoline compound having a carbamate group of the present invention or a salt thereof not only has an excellent effect as an agricultural and horticultural insecticide, but also a pest parasitic on domestic animals such as dogs and cats other than humans and cattle and sheep. It also has an excellent effect.

In the definition of the general formula (1) of the quinoline compound having a carbamate group of the present invention or a salt thereof, “halo” means “halogen atom”, and represents a chlorine atom, a bromine atom, an iodine atom or 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” refers to a linear or branched alkenyl group having 2 to 6 carbon atoms such as a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, and the like. The “(C ₂ -C ₆ ) alkynyl group” refers to a linear or branched alkynyl group having 2 to 6 carbon atoms such as propynyl group, butynyl group, pentynyl group, hexynyl group and the like.

The "(C ₃ -C ₆₎ cycloalkyl group" include cyclopropyl group, a cyclobutyl group, a cyclopentyl group, an alkyl group having a carbon number of 3 to 6 ring such as a cyclohexyl group, "(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 Linear or branched C1-C6 alcohols such as oxy groups A “(C ₂ -C ₆ ) alkenyloxy group” is, for example, a straight chain or branched chain carbon atom number 2 to 2 such as propenyloxy group, butenyloxy group, pentenyloxy group, hexenyloxy group, etc. 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, isopropylsulfinyl group Finyl 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 chain 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 , Normal butylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethyl Linear or branched alkylsulfonyl having 1 to 6 carbon atoms such as propylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, isohexylsulfonyl group, 1,1,2-trimethylpropylsulfonyl group Indicates a group.

“(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 ₁ -C ₆ ) alkoxy”, “(C ₂ -C ₆ ) alkenyloxy”, “(C ₂ -C ₆ ) alkynyloxy”, “(C ₃ -C ₆ ) cycloalkyloxy” “(C ₁ -C ₆ ) alkylthio group”, “(C ₁ -C ₆ ) alkylsulfinyl group”, “(C ₁ -C ₆ ) alkylsulfonyl group”, “(C ₂ -C ₆ ) alkenylthio group” , “(C ₂ -C ₆ ) alkenylsulfinyl”, “(C ₂ -C ₆ ) alkenylsulfonyl”, “(C ₂ -C ₆ ) alkynylthio”, “(C ₂ -C ₆ ) alkynylsulfinyl” group "," _{(C 2} -C ₆₎ alkynyl-sulfonyl group "," (C -C ₆₎ cycloalkylthio group "," (C ₃ -C ₆₎ cycloalkyl sulfinyl group ", or" (C ₃ -C ₆₎ 1 or 2 or more halogen atoms substituted may position the cycloalkylsulfonyl group " May be substituted, and when two or more halogen atoms are substituted, the halogen atoms may be the same or different.

The ones substituted with the halogen atoms are “halo (C ₁ -C ₆ ) alkyl group”, “halo (C ₂ -C ₆ ) alkenyl group”, “halo (C ₂ -C ₆ ) alkynyl group”, respectively. "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₎ cycloalkyl group "," halo _{(C 1} -C ₆₎ alkylthio group "," halo _{(C 1} -C ₆₎ alkylsulfinyl group "," halo (C ₁ -C ₆ ) alkylsulfonyl ”,“ halo (C ₂ -C ₆ ) alkenylthio ”,“ halo (C ₂ -C ₆ ) alkenylsulfinyl ”,“ halo (C ₂ -C ₆ ) alkenyl sulfonyl group "," halo _{(C 2} -C ₆₎ alkyl Thio group "," halo _{(C 2} -C ₆₎ alkynylsulfinyl group "," halo _{(C 2} -C ₆₎ alkynyl-sulfonyl group "," halo _{(C 3} -C ₆₎ cycloalkyl-thio 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 shown for a group to which the above substituent is linked. For example, in the case of a “(C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group”, a linear or branched chain It indicates that an alkoxy group having 1 to 6 carbon atoms is bonded to a linear or branched alkyl group having 1 to 6 carbon atoms.

Examples of the salt of the quinoline compound having a carbamate group represented by the general formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate, acetate, fumarate and maleate. Illustrate organic acid salts such as oxalate, methanesulfonate, benzenesulfonate, paratoluenesulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium salt be able to.

The quinoline compound having a carbamate group represented by the general formula (1) and salts thereof of the present invention may have one or more asymmetric centers in the structural formula, and two or more optical isomers may be present. And diastereomers may exist, and the present invention includes all the optical isomers and a mixture in which they are contained in an arbitrary ratio. Further, the quinoline compound having a carbamate group represented by the general formula (1) of the present invention and salts thereof may have 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 quinoline compound having a carbamate group represented by the general formula (1) of the present invention or a salt thereof, preferably R ¹ is (a1) (C ₁ -C ₆ ) alkyl group; and R ² is (B1) hydrogen atom; (b2) (C ₁ -C ₆ ) alkyl group; (b3) halo (C ₁ -C ₆ ) alkyl group; (b4) (C ₁ -C ₆ ) alkoxy (C ₁ -C) ₆₎ alkyl group; or (b5) cyano _{(C 1} -C ₆₎ alkyl group; a, ^{R 3} is, (c8) halo _{(C 1} -C ₆₎ alkyl group; (c15) halo _{(C 1} -C ₆ ) an alkylthio group; or (d17) a halo (C ₁ -C ₆ ) alkylsulfonyl group.
A is an oxygen atom or N—R ⁴ (wherein R ⁴ is (e1) a hydrogen atom; or (e2) (C ₁ -C ₆ ) an alkyl group); and A ¹ and A ² may be the same or different and are CH or a nitrogen atom, m is 2, and n is 1.

The quinoline compound having a carbamate group or a salt thereof of the present invention can be produced by, for example, the following production method, but the present invention is not limited thereto.

Manufacturing method 1

In the formula, R ¹ , R ² , R ³ , A, A ¹ , A ² , and n are the same as described above, and X represents a leaving group such as a halogen atom.

Production method of step [A] The quinoline compound represented by the general formula (1-2) is a haloquinoline compound represented by the general formula (1-5) produced by the method described in International Publication No. 2016/091731 pamphlet. And a carbamate compound according to the method described in J. A. C. S., 2002, 124 (21), 6043-6048, in the presence of a metal catalyst and a base, in an inert solvent, a cross-coupling reaction Can be manufactured.

Production method of step [B] The quinoline compound represented by the general formula (1-1) comprises a quinoline compound represented by the general formula (1-2) and R ² X represented by the general formula (2). It can be produced by reacting in the presence of an inert solvent and a base.

Bases used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, and alkali metals such as sodium hydride and potassium hydride. Examples include hydrides, alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and tertiary butoxy potassium, and alkyl lithiums such as methyl lithium and normal butyl lithium. The amount used is usually in the range of 1.0 to 10 moles compared to the haloquinoline compound represented by the general formula (1-5) or the quinoline compound represented by the general formula (1-2). Is done.

The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction. Examples thereof include alcohols such as methanol, ethanol and isopropanol; diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran and the like. Examples of the inert solvent include linear or cyclic ethers; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and nitriles such as acetonitrile. Or a mixture of two or more. Since this reaction is an equimolar reaction, (a) a haloquinoline compound and a carbamate compound represented by the general formula (1-5) or (b) a quinoline compound represented by the general formula (1-2) R ² X represented by formula (2) may be used in an equimolar amount, but any of the reactants can be used in excess.
The reaction temperature of these reactions can be carried out from room temperature to the boiling point of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 48 hours.
After completion of the reaction, the carbamate compound represented by the general formula (1-1) may be isolated from the reaction system containing the target product by a conventional method, and if necessary, purified by recrystallization, column chromatography or the like. Can be manufactured.

Manufacturing method 2

In the formula, R ¹ , R ² , R ³ , A, A ¹ , A ² , and n are the same as described above, and X represents a leaving group such as a halogen atom.

Production method of step [A] The quinoline compound represented by the general formula (1-4) can be produced by the same method as the method of step A of production step 1.

Production Method of Step [C] The quinoline compound represented by the general formula (1-3) can be produced according to the method described in ORGANIC FUNCTIONAL GROUP PREPARATIONS III 2th edition ACADEMI PRESS, INC. 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] The quinoline compound represented by the general formula (1-2) is ORGANIC FUNCTIONAL GROUP PREPARATIONS III 2th edition ACADEMI PRESS, INC. It can be produced according to the method described in 1. 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 [B] The quinoline compound represented by the general formula (1-1) can be produced by the same method as the method of step B of production step 1.

Next, specific examples of the compound of the present invention are shown below. In the entire disclosure including the following table, Me represents a methyl group, Et represents an ethyl group, n-Pr represents a normal propyl group, and i-Pr represents an isopropyl group. The physical properties indicate melting point (° C.) or ¹ H-NMR. ¹ H-NMR data are shown in Table 13.

The agricultural and horticultural insecticide containing a quinoline compound having a carbamate group represented by the general formula (1) of the present invention or a salt thereof as an active ingredient is a variety of agricultural and forestry that harms paddy rice, fruit trees, vegetables, other crops and flowers. It is suitable for pest control such as horticulture, stored grain pests, hygiene pests or nematodes, and pests that parasitize inside and outside of animals.

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 empti (Spod) (Hyphantria cunea), Awanoiga (Ostrinia furnacalis), Ayayoto (Pseudaletia separata), iga (Tinea translucens), rush saint moth (Bactra furfurana), Ichinomosei (Parnara guttata), Inaitei inferens), Brachmia triannulella, Monema flavescens, Iraqusinu Waiba (Trichoplusia ni), Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Males flamingo (Helicoverpa armigera) Phararodonta manleyi, Eumeta japonica, Pieris brassicae, Malocasoma neustria testacea, Stathmopoda masinissa, sephoblast (Cuphodes diospyrosella) Tetramoera schistaceana, yellowtail (Papilio machaon hippocrates), yellow bat (Endoclyta sinensis), guinea winged moth (Lyonetia prunifoliella), golden horned moth (Phyllonorycter ringoneella), crimma (Cydia) Eucoenogenes aestuosa), Grapeberry moss (Lobesia botrana), Black-tailed green moth (Latoia sinica), Black-faced red-eye moth (Euzophera batangensis), Phalonidia mesotypa, Spilosoma imparides moth Japanese oyster (Olethreutes mori), Japanese moth (Tineola bisselliella), Japanese bat (Endoclyta excrescens), Japanese moth (Nemapogon granellus), Cosca shiba (Synanthedon hector), Kodlinga (Cydia pomonella), Japanese black moth (Plutella xylostella), Pink Borer (Sesamia calamistis), Sankameiga (Scirpophaga incertulas), Shibata toga (Pediasia teterrellus), Potato moth (Phthorimaea operculella), Orchard moth (Stauropus fagi persimilis), Eleuella tena pod Bat (Palpifer sexnotata), Spodoptera mauritia, Scirpophaga innotata, Xestia c-nigrum, Spodoptera depravata, Anella prunus (Ephestia ku) , Seguro Hachiko ( Clostera anastomosis), Soybean looper (Pseudoplusia includens), Soybean stag beetle (Matsumuraeses falcana), Tobacco moth (Helicoverpa assulta), Tamanaginuwawa (Autographa nigrisigna), Tamanayagaga (Agrotis ipsilon), Chadokuga sperm Chanohosuga (Caloptilia theivora), Chamonaki (Homona magnanima), Chamadarameiga (Ephestia elutella), Chaminoga (Eumeta minuscula), Clostera anachoreta, Clowna anachoreta, Heliothis maritima, Spiana this pill fusca, Euproctis subflava, Biston robustum, tomato fruit worm (Heliothis zea), Aedia leucomelas, Narosoideus flavidorsalis, Nuciferum (Viuc) Grapholita molesta, Spulerina astaurota, Ectomyelois pyrivorella, Chilo suppressalis, Acrolepiopsis sapporensis, Plodia interpunctella, Islamidae, Isla Sitotroga cerealella, Spodoptera litura, Eucosma aporema, Acleris comariana, Scopelodes contractus, Orgyia thyellina, fall army worm (Spodoptera frug) ), Naranga aenescens, Andraca bipunctata, Grape squirrel (Paranthrene regalis), Grape sparrow (Acosmeryx castanea), Grape spider (Phyllocnistis toparcha), Grape turf (Endopiza viteana) Eupoecillia ambiguella), velvet bean caterpillar (Anticarsia gemmatalis), mosquito (Cnephasia cinereipalpana), mussels (Lymantria dispar), matsukareha (Dendrolimus spectabilis), peas moth (Leguminivora glycinivorella), peas phaseoli, Caloptilia soyella, Phyllocnistis citrella, Omiodes indicata, Archips fuscocupreanus, Acanthoplusia agnata, Moa sink, B (Carposina niponensis), peach moth (Conogethes punctiferalis), peach beetle (Synanthedon sp.), Peach leaf moth (Lyonetia clerkella), yellow swallowtail (Papilio helenus), common yellow butterfly (Colias erate poliographus), black moth Pieris rapae crucivora), white butterflies such as Pieris rapae, Euproctis similis, Acropepiopsis suzukiella, European corn borer (Ostrinia nubilalis), Mamestra brassicatis, ogi Hotheamaki (Phtheochroides clandestina), Apple Tokamaki (Hoshinoa adumbratana), Apple Kaleha (Odonestis pruni japonensis), Apple Kenmon (Triaena intermedia), Apple Kokukakumon-maki (Adoxophyes orana fasciata), Apple Kosinkui (Grapholita inopinata) Japanese oyster (Spilonota ocellana), Apple oyster (Spilonota lechriaspis), Apple oyster (Illiberis pruni), Apple squirrel (Argyresthia conjugella), Apple squirrel (Caloptilia zachrysa), Apple squirrel (Archips breviplicanus) , Cotton akamim (Pectinophora gossypiella), Watanomeiga (Notarcha derogata), cotton helicopter Chrono moth (Diaphania indica), fake American tobacco budworm (Heliothis virescens), and Wataringa (Earias cupreoviridis), and the like.

Hemiptera (Hemiptera) pests, for example, Nezara antennata, red beetle (Stenotus rubrovittatus), red beetle (Graphosoma rubrolineatum), red beetle (Trigonotylus coelestialium), Aeschynteles maculatus), red beetle (Creontiades pallidifer), red beetle bug (Dysdercus cingulatus), red beetle (Chrysomphalus ficus), red beetle (Aonidiella aurantii), red crab beetle (Graptops) Scale insects (Icerya purchasi), Japanese beetle (Piezodorus hybneri), Japanese beetle (Lagynotomus elongatus), Japanese white-winged beetle (Thaia subrufa), Japanese black beetle (Scotinophara luridaito) , Stariodes iwasakii, Aspidiotus destructor, Usylorilygus pallidulus, Myzusmumecola, Myzusmumepi, Pseudaulacaspis phonicr Spider helicopter (Anacanthocoris striicornis), giant black beetle (Ectometopterus micantulus), giant beetle bug (Eysarcoris lewisi), giant pest beetle (Molipteryx fuliginosa), giant beetle (Cicadella viridi) Anchovy (Saissetia oleae), Whitefly (Trialeurodes vaporariorum), Amelia moth (Aguriahana quercus), Anthracnose bug (Lygus spp.), Euperaphis puncti pennis), citrus scale insects (Andaspis kashicola), citrus scale insects (Coccus pseudomagnoliarum), king beetle bugs (Cavelerius saccharivorus), chrysanthemum beetle (Galeatus spinifrons), citrus beetle moth, (Halyomorpha mista), Stephanitis fasciicarina, Trio's camphorae, Leptocorisa chinensis, Trioza quercicola, Uhryitesthrone ッ パ ー, Grays Black-footed beetle (Paromius exiguus), Black-footed beetle (Duplaspidiotus claviger), Nephotettix nigropictus, Black-headed turtle (Halticiellus insularis), Black croaker Leafhopper (Perkinsiella saccharicida), black apple lice (Psylla malivorella), stag beetle (Anomomeura mori), stag beetle (Pseudococcus longispinis), stag beetle (Pseudaulacaspis pentagona), stag beetle ), Scarcharidus aphid (Togo hemipterus), Komikan Aphid (Toxoptera aurantii), Sugarcane scale insect (Saccharicoccus sacchari), Sugar beetle (Geoica lucifuga), Sugar ), Citrus snow scale (Unaspis citri), potato beetle aphid (Aulacorthum solani), white stink bug (Eysarcoris ventralis), silver leaf whitefly (Bemisia argentifolii), white leafhopper (Cicadella) spectra), white beetle (Aspidiotus hederae), red beetle bug (Liorhyssus hyalinus), white beetle (Calophya nigridorsalis), white-footed beetle (Sogatella furcifera), broad beetle aphid (Megoura コ ン crad) (Aphis glycines), Leptocorisa oratorius, Nephotettix virescens, Arophicon formosanum, Tobacco leaf (Cyrtopeltis tennuis), Tobacco tabaica , Chalcoleophyllum (Parlatoria theae), Chano marine scale (Pseudaonidia paeoniae), Empoasca onukii, Chalauen stink bug (Plautia stali), Chu Dipsa aphids (Dysaphis tulipae), Tulip beetle aphids (Macrosiphum euphorbiae), Azalea (Stephanitis pyrioides), horn beetle (Ceroplastes ceriferus), Camellia cris ), Glaucias subpunctatus, sugar beet turtle (Orthotylus flavosparsus), corn aphid (Rhopalosiphum maidis), corn planthopper (Peregrinus maidis), thornbill beetle (Eysarcoris parvus), cyper (Nilaparvata lugens), Psylla tobirae, Eurydema rugosum, Schizaphis piricola, Psylla pyricola, Nacyclohoshi Aphids (Parlatoreopsis pyri), Nasigunbai (Stephanitis nashi), Nasibonkai scales (Dysmicoccus wistariae), Neptune scales (Lepholeucaspis japonica), Nasimaru aphids (Sappaphis piri), Nisedai phi sera ), Rhopalosophum nymphaeae, Edwardianarosae, Pinnaspisaspidistrae, Pinspisaspidistrae, Psylla alni, Speusotettix ellafue panicicola), Adelphocoris lineolatus, Dysdercus poecilus, Parrotia ziziphi, Uhlerites debile, Lame lphax striatella), Eurydema pulchrum, Cletus trigonus, Clovia punctata, Empoasca sp., Copacus brilliant luridus), Japanese scale insect (Planococcus kraunhiae), stag beetle (Stenotus binotatus), sable beetle (Arboridia apicalis), scallop (Macrosteles fascifrons), spotted beetle (Dolycoris baccadel), triannulatus, grape aphid (Viteus vitifolii), beetle stink bug (Acanthocoris sordidus), black beetle stink bug (Leptocorisa acuta), stink bug (Macropes obnubilus), snail beetle (Cletus cl tus), potato pisilido (Paratrioza cockerelli), Maekiawafuki (Aphrophora costalis), yellow turtle (Lygus disponsi), spotted turtle (Lygus saundersi), pine beetle (Crisicoccus pinis), pine Emuco matsumotoi), bean aphid (Aphis craccivora), mare beetle (Megacopta punctatissimum), marsh beetle (Eysarcoris guttiger), citrus beetle (Lepidosaphes beckii), citrus beetle (Diaphorina citer) (Planococcus citri), citrus whitefly (Dialeurodes citri), mandarin white lice (Aleurocanthus spiniferus), mandarin orange scale (Pseudococcus citriculus), mandarin orange leafworm (Zyginella citriulus), mandarin orange hawk Aphids (Pulvinaria citricola), Citrus scale insects (Coccus discrepans), Citrus scale insects (Pseudaonidia duplex), Citrus scale insects (Pulvinaria aurantii), Mizuki beetle scales (Lecaniumicorni), Minamiokaimu te (N) calcaratum), wheat beetle aphid (Rhopalosiphum padi), wheat aphid (Sitobion akebiae), wheat aphid (Schizaphis graminum), wheat leaf (Sorhoanus tritici), wheat walleye moth purim, ichBrachycaud Aphids (Myzus persicae), peach beetle (Hyalopterus pruni), willow beetle (Aphis farinose yanagicola), willow beetle (Metasalis populi), wild beetle (Unaspis yanonensis), porcupine Sacral lice (Mesohomotoma camphorae), Snowy eagle aphids (Aphis spiraecola), Apple aphids (Aphis pomi), Apple oyster scales (Lepidosaphes ulmi), Apple killer whales (Psylla mali), Apple croaker worms (Heterocordylis tus flavus) , Aphidonuguis mali, Orientus ishidai, Ovatus malicolens, Eriosoma lanigerum, Ceroplastes rubens, and Aphis gossypii et al.

Coleoptera (Coleoptera) pests include, for example, Xystrocera globosa, Aobaarie-hane-kakushi (Paederus fuscipes), Ahanamuri (Eucetonia roelofsi), Azuki beetle (Callosobruchus chinensis), Arimodosium (Hypera postica), rice weevil (Echinocnemus squameus), rice beetle (Oulema oryzae), rice weevil (Donacia provosti), rice weevil (Lissorhoptrus oryzophilus), Weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), weevil weevil (Involvulus cupreus), weevil (Aulacophora femoralis), pea weevil (Bruchus pisorum) Epilachna vigintioctomaculata, Carpophilus dimidiatus, Cassida nebulosa, Luperomorpha tunebrosa, Phyllotreta striolco ), Curculio sikkimensis, Carpophilus hemipterus, Oxycetonia jucunda, Cornroot worms (Diabrotica spp.), Mimela splendens, Ribo zeum castaneum), weevil (Sitophilus oryzae), red-footed beetle (Palorus subdepressus), black beetle (Melolontha japonica), long-horned beetle (Anoplophora malasiaca), red beetle (Neatus picipes), inotarsa decemlineata), Southern corn rootworm (Diabrotica undecimpunctata howardi), sword beetle weevil (Sphenophorus usvenatus), juvenile horned beetle (Crioceris quatuordecis puncture), weevil (Conotrachelus nenupor Phaedon brassicae), tobacco beetle (Lasioderma serricorne), chibi beetle weevil (Sitona japonicus), white-horned beetle (Adoretus tenuimaculatus), white-footed beetle (Tenebrio molitor), Common beetle (Chaetocnema concinna), Dolphin's buoy (Anomala cuprea), Nagachakogane (Heptophylla picea), Epilachna vigintioctopunctata, Northern corn root worm (Diabrotica longicornis), Hanam Guri (Eucetonia pilifera), bark beetles (Agriotes spp.), Horned beetle (Attagenus unicolor japonicus), Japanese horned beetle (Pagria signata), Japanese common squirrel (Anomala rufocuprea), himekoku nostomu (Pii) laevigatus), Anthrenus verbasci, Oyster beetle (Lyctus brunneus), Olymptera cricket (Tribolium confusum), Methithia nigrobilineata, Grapy tiger beetle (Xylotrechus Pinewood beetle (Tomicus piniperda), pinewood spotted beetle (Monochamus alternatus), bean squirrel (Popillia japonica), bean scorpion (Epicauta gorhami), maizewevil (Sitophilus zeamais), peach squirrel tess Cowpea weevil (Callosobruchus maculatus), apple 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, red flies fly (Pegomya hyoscyami), red spider fly (Liriomyza huidobrensis), house fly (Musca domestica), rice flies Flies Fruit flies (Rhacochlaena japonica), fruit flies (Muscina stabulans), fruit flies such as fruit flies (Megaselia spiracularis), giant butterflies (Clogmia albipunctata), mushroom moth (Tipula aino), hormone moth (Pipula) rhynchus), Anopheles sinensis, Japanese flies (Hylemya brassicae), Soybean fly (Asphondylia sp.), Panax fly (Delia platura), Onion fly (Delia antiqua) RRen ), Ceratitis capitata, Bradysia agrestis, sugar beetle fly (Pegomya cunicularia), tomato leaf fly (Liriomyza sativae), eggplant fly (Liriomyza ticy moth) ), Aedes aegypti, Aedes albopictus, Bumbleflies (Liriomyza trifolii), Tomato leafflies (Liriomyza sativae), Citrus dors (a) (Dacus tsuneonis), wheat red midge (Sitodiplosis mosellana), Mugikimoguribae (Meromuza nigriventris), Mexican fruit flies (Anastrepha ludens), and apple maggot (Rhagoletis pomonella), and the like.

For example, Hymenoptera (Pristomyrmex pungens), Arbatidae, Monomelium pharaonis, Pheidole noda, Athalia rosae, Cristoforma, Kuriphilus , Hornets, black bee (Athalia infumata infumata), horned bee (Arge g pagana), Japanese bee (Athalia ハ japonica), cricket (Acromyrmex spp.), Fire ant (Solenopsis spp.), Apple honey bee (Arlen ali) (Ochetellus glaber) and the like.

Examples of the insects of the order Diptera (Hortocoryphus lineosus), Kera (Gryllotalpa sp.), Coago (Oxya hyla intricata), Cobainago (Oxya yezoensis), Tosama locust (Locusta migrago), Oneya (Homorocoryphus jezoensis), and emma cricket (Teleogryllus emma).

Examples of thrips of the order Thrips (Selenothrips rubrocinctus), thrips (Stenchaetothrips biformis), Thrips thrips (Haplothrips , Lithrips floridensis, Thrips simplex, Thrips nigropilosus, Helothripes Leeuwenia pasanii), Shiritaku Thrips pasaniae, Citrus Srips citri, Hypothrips chinensis, Soybean Thrips (Mycterothrips glycines), Da Thrips setosus, Thripsrtsaw Thrips hawaiiensis, Haplothrips kurdjumovi, Thrips coloratus , Lilyripa vaneeckei, and the like.

For example, mite moths (Leptotrombidium akamushi), Ashinowa spider mite (Tetranychus ludeni), American dock ticks (Dermacentor variabilis), Ichinami spider mite (Tetranychus truncatus), house dust mite (Ornithonyssus bacoti), mite Tetranychus viennensis), ticks (Tetranychus kanzawai), ticks (Rhipicephalus sanguineus) and other ticks (Cheyletus acc malaccensis), stag beetle tick (Tyrophagus putrescent moth) Tick (Dermacentor taiwanicus), Chinese cabbage mite (Acaphylla theavagrans), Chinese dust mite (Polyphagotarsonemus latus), Tomato mite (Aculops lycopersici), Trichoid mite (Ornithonyssus sylvairum), Nami spider mite (Tetranychus) icae), red spider mite (Eriophyes chibaensis), hymenid mite (Sarcoptes scabiei), black tick (Haemaphysalis longicornis), black legged tick (Ixodes , Southern ticks (Cheyletus moorei), southern ticks (Brevipalpus phoenicis), earthworm ticks (Octodectes cynotis), salmon mites (Dermatophagoides ptrenyssnus), yamato tick (Haemaphysalis flava), yamades ticks Apple spider mites (Aculus schlechtendali), apple spider mites (Panonychus ulmi), Lone star ticks (Amblyomma americanum), duck spider (Dermanyssus gallinae), Robin ticks (Rhyzoglyphus robini), a kind of spider mite (Sancassania sp.) It is done.

As the termite pests, for example, Amite termites (Reticulitermes miyatakei), American termites (Incisitermes minor), Termites (Coptotermes formosanus), Termites (Hodotermopsis japonica), Common termites (Reticulitermes termm ants) , Glyptotermes , Nakajima termite (Glyptotermes nakajimai), Nitobe termite (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 lituriplanet (Periplaneta americana) and the like.

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

Nematodes, for example, strawberry nematode (Nothotylenchus acris), rice scallop nematode (Aphelenchoides besseyi), red-footed nematode (Pratylenchus penetrans), red-knot nematode (Meloidogyne hapla), sweet potato nematode (Meloidogyne rostochiensis), Javaloid nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), southern nematode nematode (Pratylenchus coffeae), and pterolenchus nematode (Pratylenchus neglectus)

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

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

In addition, animal parasite ticks (Boophilus microplus), black tick ticks (Rhipicephalus sanguineus), yellow tick ticks (Haemaphysalis longicornis), yellow ticks (Haemaphysalis flava), tsurigane tick ticks (Haemaphysata tick) , Tick (Haemaphysalis concinna), tick (Haemaphysalis japonica), tuna (Haemaphysalis kitaokai), tick (Haemaphysalis ias), tick (Ixodes ovatus), tick desmite Ticks, Dermanyssus, ticks such as Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis gallinae), avian mite (Ornithonyssus sylviarum), and avian mite such as Ornithonyssus bursa, Eutrombicula wichmanni, Leptotrombidium akamushi, Leptotrdium LLeptotrdium eptLeptotrdium eptLeptotrdium Tsutsumushi (Leptotrombidium tosa), European tick (Neotrombicula autumnalis), American tsutsugamushi (Eutrombicula alfreddugesi), and the tsutsugamushi tsutsumi (Helenicula miyagawai); And ticklets such as the catlet tick (Cheyletiella キ ュ blakei), rabbit cucumber mite (Psoroptes cuniculi), oxenid mite (Chorioptes bovis), and wolf mite mite (Otodectes cynotis) , Mites (Sarcoptes scabiei), and mites, such as a cat foraminous mites (Notoedres cati), as well as Demodex, etc. such as Inunikibidani (Demodex canis) can be mentioned.

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

Further, other ectoparasites to be controlled include, for example, cattle lice (Haematopinus eurysternus), horse lice (Haematopinus asini), sheep lice (Dalmalinia ovis), cattle lice (Linognathus vituli), pig lice (Haematopinus ラ suius ケ pubis), And lice such as head lice (Pediculus capitis), and lice such as dog lice (Trichodectes canis), buffalo (Tabanus trigonus), green hawks (Culicoides schultzei), and blood-sucking dipterans such as Simulium ornatum Examples include pests. In addition, examples of endoparasites include nematodes such as pneumoniae, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms, manson cleft worms, broad-headed crest worms, berries 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 parasites, intestinal granulocysts, toxoplasma And protozoa such as Cryptosporidium.

The agricultural and horticultural insecticides containing the quinoline compound having a carbamate group represented by the general formula (1) of the present invention or a salt thereof as an active ingredient are paddy field crops, field crops, fruit trees, vegetables, other crops, flower buds, etc. It has a remarkable control effect against the pests that cause damage to the pests, so that it matches the time when the occurrence of the pests is predicted, before the occurrence of the pests or at the time when the occurrence is confirmed, paddy field, field, fruit tree, The desired effects of the agricultural and horticultural insecticide of the present invention can be achieved by treating the seeds such as vegetables, other crops, flower buds, paddy water, stalks and leaves, or soil and other cultivation carriers. Among them, it is treated with seedling soil such as crops, 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, Tomatoes, spinach, broccoli, lettuce, onions, green onions (satsuki, parsley), peppers, eggplants, strawberries, peppers, ladle, leek, etc. , Garlic, raccoon, etc.), crops for processing (crab, hemp, beet, hop, sugar cane, sugar beet, olive, rubber, coffee, tobacco, tea, etc.) Cucumbers (pumpkin, cucumber, watermelon, mushroom, melon, etc.), pastures (orchard grass, sorghum, timothy, clover, alfalfa, etc.), turf (Korean turf, bentgrass, etc.), fragrances, etc. , Rosemary, thyme, parsley, pepper, ginger, etc.), flowers (flowers, roses, carnations, orchids, tulips, lilies, etc.), garden trees (ginkgo, sakura, aoki, etc.), forest trees (Todomatsu, spruce, 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. Also included are plants that have been rendered resistant by classical breeding methods or genetic recombination techniques to resistance to herbicides such as acetyl CoA carboxylase inhibitors, bromoxynil, dicamba, 2,4-D.

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 of 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 trion 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). Introducing a plant resistant to an acetyl-CoA carboxylase inhibitor by introducing a mutation associated with imparting resistance into 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.), A nucleic acid introduced with a base substitution mutation is introduced into a plant cell. By introducing site-specific amino acid substitution mutations into the chill 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 transgenic plants, insecticidal proteins derived from Bacillus cereus and Bacillus popirie; δ- such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C Endotoxins, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; nematicidal insecticidal proteins; 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. Bosome 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 inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase and the like.

Further, as toxins expressed in such genetically modified plants, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab and 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.

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

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 as application to house building materials, smoke, bait 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 coating the seed by mixing with an adhesive carrier such as resin and polymer, and a method of spraying around the seed simultaneously with planting.
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 a method of application to paddy fields, solid preparations such as jumbo agents, packs, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields. In addition, at the time of rice planting, an appropriate 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 emulsion or flowable as a source of water flowing into a paddy field such as a water mouth or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.

In field crops, it can be treated to seeds or a cultivation carrier close to the 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 the plant source of the 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 granule spraying treatment to the seedling nursery is preferred. 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 quinoline compound having a carbamate group represented by the general formula (1) or a salt thereof of the present invention is blended in an appropriate inert carrier or, if necessary, with an auxiliary agent in an appropriate ratio. Dissolve, separate, suspend, mix, impregnate, adsorb or adhere to appropriate dosage forms such as suspensions, emulsions, solutions, wettable powders, wettable powders, granules, powders, tablets, packs, etc. It can be used by formulating.

The composition of the present invention (agricultural and horticultural insecticide or animal parasite control agent) 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 support 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. Synthetic silica, synthetic silicate, starch, cellulose, organic solid carriers such as plant powder (eg sawdust, coconut cob, tobacco stalk, etc.), plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, urea, Examples thereof include inorganic hollow bodies, plastic hollow bodies, fumed silica (fumed white silica) and the like. 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 paraffins, naphthenes, isoparaffins, kerosene, mineral oils and other aliphatic hydrocarbons 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, polyoxye Lenalkylamine, 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, alkylbenzene sulfonate, alkylaryl sulfonate, lignin sulfonate, alkyls 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 boundaries such as amino acid type or betaine type Active agents. These surfactants may be used alone or in combination of two or more.

Examples of binders and tackifiers include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, 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, phospholipids (eg, cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, crosslinked polyvinylpyrrolidone, maleic acid and styrene Polymers, (meth) acrylic acid copolymers, half-esters of polycarboxylic alcohols and dicarboxylic acid anhydrides, water-soluble salts of polystyrene sulfonic acid, Fins, 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.

Adjuvants for preventing caking and promoting disintegration include, for example, polysaccharides such as starch, alginic acid, mannose, galactose, polyvinylpyrrolidone, fumed silica (fumed silica), 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 blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the 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 suitably selected from the range of 0.001 g to 10 kg per 10 ares, preferably 0.01 g to 1 kg depending on 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 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.

Other agricultural and horticultural insecticides, acaricides, and nematicides used for such purposes include, for example, 3,5-xylyl methylcarbamate (XMC), Bacillus thuringiensis aizawai, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis kurstaki, Thuringiensis tenebrionis, crystal protein toxin produced by Bacillus thuringiensis, BPMC, Bt toxin insecticidal compound, CPCBS (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, acequinosyl (acequinocyl), acetamiprid (acetamiprid), acetoprole (acetoprole), acephate, abamectin, averme Avermectin-B, amidoflumet, amitraz, alanycarb, aldicarb, aldoxycarb, aldrin, alpha-endosulfan, alpha Permethrin (alpha-cypermethrin), albendazole, allethrin, isazofos, isamidofos, isamidofos, isoxathion, isofenphos, isoprocarb: PC Ivermectin, imicafos, imidacloprid (imidac1oprid), imiprotrin, indoxacarb, esfenvalerate, ethiofencarb, ethion, ethiproe (etoxazole), et Ethofenprox, etoprophos, etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin, oxamyl, oxydimeton-methyl methyl), oxydeprofos (ESP), oxibendazole, oxfendazole, potassium oleate (sodium oleate), sodium oleate, cadusafos, cartap ), Carbaryl (carbary1), carbosulfan, carbofuran, gamma-cyhalothrin, xylylcarb, quinalphos, quinoprene, chinomethionat, cloetocarb (cloethocarb), clothianidin (clothianid in), clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos, chlorethoxymeform, chlordane, chlorpyrifos, chlorpyrifos-methyl (chlorpyrifos) chlorpyrifos-methyl, chlorphenapyr, chlorfenson, ch1orfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate, kelbenzo (dicophol): dicofol, salithion, cyanophos (CYAP), diafenthiuron, diamidafos, cyantraniliprole, theta-cypermethrin, dienochlor Cyenopyrafen (cyeno pyrafen), dioxabenzofos, diofenolan, sigma-cypermethrin, dichlofenthion (ECP), cycloprothrin, dichlorvos (DDVP), disulfone (sulfon) , Dinotefuran, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, cyflumetofen, diflovidazin, cyhexatin, cyhexatin, cyhexatin, cyhexatin, cyhexatin Dimethylvinphos, dimethoate, dimefluthrin, silafluofen, cyromazine, spinetoram, spinosad, spirodiclofen, spirotetramat, spirotetramat Spiromesifen, sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin, diazinon, tau-fluvalinate, dazomet , Thiacloprid, thiamethoxam, thiodicarb, thiocyclam, thiosultap, thiosultap-sodium, thiosultap-sodium, thionazin, thiometon, deet , Dieldrin, tetrach1orvinphos, tetradifon, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tebufenpyrad ), Tef Teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, tralopyril, tralomethrin, transfluthrin, Triazamate, triazuron, trihlamide, trichlorphon (DEP), triflumuron, tolfenpyrad, nared (nithiazine), nitenpyram (nitenpyram), nitenpyram (nitenpyram) (novaluron), noviflumuron, hydroprene, vaniliprole, bamidothion, parathion, parathion-methyl, halfenprox, halofenozide , Bistrifluron, bisluta Bisultap, hydramethylnon, hydroxypropyl starch (binapacryl), biapacryl, bifenazate, bifenthrin, pymetrozine, pyraclorfos, pyrafluprolol pyrafluprole, pyridafenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pyrimicarb, pyrimidipheny ), Pyrethrin (pyrethrins), fipronil (fiproni1), fenazaquin (fenazaquin), fenamiphos (fenamiphos), phenisothion (bromoMEP), phenoxycarb (fenoxycarb), fenothiocarb (fenothiocarb), fenothiocarb Phenothrin, fenobucarb, fensulfothion, fenthion (MPP), phenthoate (PAP), fenvalerate, fenpyroximate, fenpropathrin, fenpropathrin Fenbendazole, fosthiazate, formetanate, butathiofos, buprofezin, furathiocarb, prallethrin, fluacrypyrim, fluaziryn, fluazinam, fluazinam fluazuron, fluensulfone, flucycloxuron, flucythrinate, fluvalinate, flupyrazofos, flufenerim, flufenoxuron, flufendi (flufenzine), flufenprox, fluproxyfen, flubrocythrinate, flubendiamide, flumethrin, flurimfen, prothiofos, prothiofos Protrifenbute, flonicamid, propaphos, propargite: BPPS, profenfos, profluthrin, propoxur: PHC, bromopropylate, beta- Cyfluthrin, hexaflumuron, hexythiazox, heptenophos, permethrin, benclothiaz, bendiocarb, bensu1tapmate, benzoximate (benzo) , Benfuracarb, Hoxy Phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet (PMP), polynactins, formetanate, formotenate (formothion), phorate, machine oil, malathion, milbemycin, milbemycin-A, milbemectin, mecarbam, mesulfenfos, mesomil (methomyl), metaldehyde, metaflumizone, metamidophos, metam-ammonium, metam-sodium, methiocarb, methidathion (DMTP), Methylisothiocyanate, methyl neodecanamide (m ethylneodecanamide, methylparathion, methoxadiazone, methoxychlor, methoxyfenozide, methopenflurin, methoprene, metolcarb, melfluthrin, phos, monophos, monophos (monocrotophos), monosultap, lambda-cyhalothrin, ryanodine, lufenuron, resmethrin, repimectin, rotenone, levamisol hydrochloride, levamisol hydrochloride Fenbutatin oxide, morantel tartarate, methyl bromide, tricyclohexyl tin hydroxide, calcium nitrogen, calcium sulfur, sulfur ) And disulfate It can be exemplified Chin (nicotine-sulfate) and the like.

Examples of agricultural and horticultural fungicides used for similar purposes 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 Oxpoconazole-fumarate, oxolinic acid, octhilinone, ofurace, orysastrobin, metam-sodium, kasugamycin, carbamorph, carpropamide ( carpropamid, carbendazim, carboxin, carboxin, carvone, quinazamid, quinazatol, quinacetol, quinoxyfen, quinomethionate, captafol, captan ), Kiraraxyl, quinconazole, quintozene, guazatine, cufraneb, cuprobam, glyodin, griseofulvin, crimazol le), cresol, cresoxim-methyl, clozolinate, clotrimazole, clobenthiazone, chloraniformethan, chloranil, chlorquinox (Chlorquinox), chloropicrin, chlorfenazole, chlorodinitronaphthalene, chlorothalonil, chloroneb, zarilamid, salicylanilide, cyazofamid, cyazofamid Dilo pyrocarbonate, diethofencarb, cyclafuramid, diclocymet, dichlozoline, diclobutrazol, di Chlofluanid, cycloheximide, diclomezine, dicloran, dichlorophen, dichlorophen, dichlone, disulfiram, ditalimfos, dithianon, dithianon, dithianon, dithianon , Diniconazole-M, diniconazole-zineb, dinocap, dinocton, dinosulfon, dinoterbon, dinobuton, dinopenton, dipyrithione, amine (Diphenylamine), difenoconazole, cyflufenamid, diflumetorim, cyproconazole, cyprodinil, cyprofuram, Cypendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, methyl bromide, ziram, silthiofam , Streptomycin, spiroxamine, sultropen, sedaxane, zoxamide, dazomet, thiadiazin, thiadinil, thiadifluor, thiabendole , Thioxymid, thiochlorfenphim, thiophanate, thiophanate-methyl, thicyofen, thioquinox, quinome Thionate, thiofluzamide, thiram, decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid (Dehydroacetic acid), tebuconazole, tebufloquin, tebufloquin, dodicin, dodine, dodecylbenzenesulfonic acid bisethylenediamine copper complex (II) (DBEDC), dodemorph, dorazoxolon, Triadimenol, triadimefon, triazbutil, triazoxide, triamiphos, triarimol, trihlamide, trichlamide, tricyclazole, tricyclone Ticonazole, tridemorph, tributyltin oxide, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos- methyl, natamycin, nabam, nitrothal-isopropyl, nitrostyrene, nuarimol, copper nonylphenol sulfonate, halacrinate, validamycin (Validamycin), valifenalate, harpin protein, bixafen, picoxystrobin, picobenzamide, bithionol, viteltanor (Bitertanol), hydroxyisoxazole, hydroxyisoxazole-potassium, binapacryl, biphenyl, piperalin, hymexazol, pyraoxystrobin , Pyracarbolid, pyraclostrobin, pyrazophos, pyrametostrobin, pyriophenone, pyridinitril, pyrifenox, pyribencarb, pyrimethilpy ), Pyroxychlor, pyroxyfur, pyroquilon, vinclozolin, famoxadone, fenapanil, fenamidone Fenaminosulf, fenarimol, fenitropan, phenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpyrazamine, fenburazazole (fenpyrazamine) fenbuconazole), fenfuram, fenpropidin, fenpropimorph, fenhexamid, phthalide, buthiobate, butylamine, bupirimate, fuberidazole (Fuberidazole), blasticidin-S, furametpyr, furalaxyl, fluacrypyrim, fluazinam, fluoxastrob in), fluotrimazole, fluopicolide, fluopyram, fluoroimide, furcarbanil, fluxapyroxad, fluquinconazole, fluconazole , Fluconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, furfural, flumeciclox (Furmecyclox), flumetover, flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole nazole), propamocarb, propiconazole, propineb, propineb, furophanate, probenazole, bromuconazole, hexachlorobutadiene, hexaconazole, Hexylthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl, pefazoate, benquinox, penconazole, penconazole, penconazole (Benzamorf), pencicuron, benzohydroxamic acid, bentaluron, benthiazole, benchthiavalicarb-isopropyl, pen Opiado (penthiopyrad), penflufen, boscalid, phosdiphen, fosetyl, fosetyl aluminum (fosetyl-Al), polyoxins, polyoxorim, polycarbamate, Folpet, formaldehyde, machine oil, maneb, mancozeb, mandipropamid, microzoline, myclobutanil, mildiomycin, milneb (Milneb), mecarbinzid, metasulfocarb, metazoxolon, metam, metam-sodium, metalaxyl, metalaxyl-M, methylamyl (Metiram , Methyl isothiocyanate, mepthyldinocap, metconazole, metsulfovax, metsulfoxax, methfuroxam, metinominostrobin, metrafenone, mepanypyrim rim , Mefenoxam, meptyldinocap, mepronil, mebenil,
Inorganic sterilization, such as methyl iodide (iodomethane), rabenzazole, benzalkonium chloride, basic copper chloride, basic copper sulfate, silver metal Agent, sodium hypochlorote, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, carbonic acid Copper-based compounds such as sodium hydrogen carbonate, inorganic sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, 8-hydroxyquinoline copper, sulfuric acid Examples thereof include zinc sulfate and copper sulfate pentahydrate.

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, allychlor (allidochlor), alloxydim, alorac, isouron , Isocarbamid, isoxachlortole, isoxapyrifop, isoxaflutole, isoxafluto, isoxaben, isocil, isonoruron, isoproturon , Isopropalin, isopolinate, isomethiozin, inabenfide, ipazine, ipfencarbazone, iprymidam, imazaquin, imazapic, imazapic I 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, carfentra Carfentrazone, carfentrazone-ethyl, carbutilate, carbetamide, carboxazole, quizalofop, quizalofop-P (Quizalofop-P), quizalofop-ethyl, xylachlor, quinoclamine, quinonamid, quinclorac, quinmerrac, quinmerac, cumyluron, cryogenate ( cliodinate), glyphosate, glufosinate, glufosinate-P, glufosinate-P, credazine, clethodim, cloxyfonac, clodinafop, clodinafop, clodinaf propargyl), chlorotoluron, clopyralid, cloproxydim, cloprop, chlorbromuron, clofop, clomazone, clomethoxyni1 and clomethoxyphen ( chlome thoxyfen, clomeprop, chlorazifop, chlorazine, chloransulam, chloranocryl, chloramben, chloransulam-methyl, chloridazon, chlorimuron ), Chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamid, chlortoluron, chlornitrofen, chlorfenac, chlorfenprop ), Chlorbufam, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, Chloreturon, chloroxynil, chloroxuron, chloropon, saflufenacil, cyanazine, cyanatryn, di-allate, diuron, diethamquat ), Dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron, dichlorprop, dichlorprop-P , Dichlobenil, diclofop, diclofop-methyl, dichlormate, dichloralurea, diquat, cisanilide, disul, siduron , Jichi Dithiopyr, dinitramine, cinidon-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop, haloprop Butyl (cyhalofop-butyl), diphenamid, difenoxuron, difenopenten, difenzoquat, cybutryne, cyprazine, cyprazole, diflufenican, diflufen Diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine, dimexano, dimethachlor, dimedazon, dimidazon , Dimethametryn, dimethenamid, dimethenamid, simetryn, simeton, dimepiperate, dimefuron, cinmethylin, swep, sulglycapin, sulglycone ), Sulfallate, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl, secbumeton, sethoxydim, cebuthylazine ), Terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr, thiencarbazone, thiencarbazon e-methyl), thiocarbazil, tioclorim, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedifam (Desmedipham), desmetryn, tetrafluron, tenenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tefuryltrione, tefuryltrione tembotrione, delachlor, terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralcoxy Tralkoxydim, triaziflam, triasulfuron, tri-allate, trietazine, tricamba, triclopyr, tridiphane, tritac, tri Tosulfuron, triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, tribenuron -methyl), tribenuron, trifop, trifopsime, trimeturon, naptalam, naproanilide, napropamide, nicosulfuron, nitralin, nitralin D Nitrofen, 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, pydanon, pinoxaden, bifenox, Piperojo Piperophos, hymexazol, pyraclonil, pyrasulfotole, pyrazoxifene, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazolate bilanafos ), Pyraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate, pyrifalid, pyributicarb ), Pyribenzoxim, pyrimisulfan, pyrimisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxsulam, phenuslam asulam), phenisopham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, phenoxathiol (phenothio1), fenoprop, fenobenzuron, fenthiaprop,
Fenteracol, fentrazamide, fenmedipham, phenmedipham-ethyl, butachlor, butafenacil, butamifos, buthiuron, butydazole buthidazole, butyrate, butylate, buturon, butenachlor, butroxydim, butralin, flazasulfuron, flamprop, furyloxyfen, plinachlor (Prynachlor), primisulfuron-methyl, fluazifop, fluazifop-P, fluazifop-butyl, fluazolate, fluroxypyr, fluroxypyr Fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone Flucarbazone-sodium, fluchloralin, flucetosulfuron, fluthiacet, fluthiacet-methyl, flupyrsulfuron, flufenacet, flufenican (Flufenican), flufenpyr, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac, flumicrolorac Flumiclorac-pentyl, flumipropyn, flumezin, fluometuron, flumetsulam, fluridone, flurtamone, fluroxypyr, prochlorxan, prechloraxol ), Proglinazine, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propaquizafop, propachlor , Propazine, propanil, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron, propham, proflua Profluazol, profluralin, prohexadione-calcium, propoxycarbazone, propoxycarbazone-sodium, propoxydim, bromacil, brompyrazon ), Promethrin, prometon, bromoxynil, bromofenoxim, bromobutide, bromobonil, florasulam, hexachloroacetone, hexaazinone, Petoxamide, benazolin, penoxsulam, pebulate, beflubutamid, vernolate, perfluidone, ben Bencarbazone, benzadox, benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulide, bensulfuron-methyl, Benzoylprop, benzobicyclon, benzofenap, benzofluor, benzofluor, bentazone, pentanochlor, benthiocarb, pendimethalin , Pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron, forchlorfenuron, maleic hydrazide (maleic hydrazide), mecoprop (mecoprop), mecoprop-P (mecoprop-P), mezinoterb (medinoterb), mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprone (mesoprazine) methoprotryne, metazachlor, methazole, metazosulfuron, metabenzthiazuron, metamitron, metamifop, metam, metalpropalin, Methiuron, methiozolin, methiobencarb, methyldymron, metoxuron, metosuram, metsulfuron, metsulfuron, metsulfuron-methy1 Metflurazon, metobromuron, metobenzuron, metometon, metolachlor, metribuzin, mepiquat-chloride, mefenacet, mefluidet, mefluide , Monalide, monisouron, monuron, monochloroacetic acid, monolinuron, molinate, morfamquat, iodosulfuron, iodosulfuron Methyl sodium (iodosulfuron-methyl-sodium), iodobonil, iodomethane, lactofen, linuron, rimsulfuron, lenacil, rhodethanil, potassium peroxide Siumu (calcium peroxide), can be exemplified methyl bromide (methyl bromide) and the like.

Examples of biological pesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect pox virus (Entomopoxivirus, EPV) ) Virus preparations, Monocrosporium ポ リ phymatophagum, Steinernema ナ carpocapsae, Steinernema kushidai, Pasturia ペ pene insecticides, and Pasturia pene insecticides Sterilization of microbial pesticides, Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc. As microbial pesticide to be used, by using mixed such as biological pesticides utilized as herbicides, such as Xanthomonas campestris (Xanthomonas campestris), the same effect can be expected.

Furthermore, examples of biological pesticides include Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusahysrica persimilis), natural enemies 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 -May also be used in combination with pheromone agents such as octadecene It is a function.

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
Process for producing 6-acetylamino-3- (ethylsulfonyl) -2- (5- (trifluoromethylthio) benzoxazol-2-yl) quinoline

6-Bromo-3- (ethylsulfonyl) -2- (5- (trifluoromethylthio) benzoxazol-2-yl) quinoline (390 mg, 0.75 mmol) prepared by the method described in WO2016 / 091731 8 mL), acetamide (89 mg, 1.5 mmol), tris (dibenzylideneacetone) dipalladium (69 mg, 0.075 mmol), Xantphos (99 mg, 0.18 mmol), diisopropylethylamine (490 mg, 1.5 mmol) And stirred at 90 ° C. for 3 hours under an argon atmosphere. The reaction mixture was subjected to silica gel column chromatography to obtain the desired product (250 mg, 72%).
Melting point: 280-282 ° C

Reference Example 2
Process for producing 6-amino-3- (ethylsulfonyl) -2- (5- (trifluoromethylthio) benzoxazol-2-yl) quinoline

6-acetylamino-3- (ethylsulfonyl) -2- (5- (trifluoromethylthio) benzoxazol-2-yl) quinoline (200 mg, 0.40 mmol) prepared in the previous step was dissolved in methanol (20 mL). Then, 2N HCl aqueous solution (2 mL) was added, and the mixture was stirred with heating under reflux for 2 hours. After the reaction, the reaction solution was neutralized by adding ethyl acetate and saturated aqueous sodium hydrogen carbonate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain the desired product (130 mg, 66%).
Melting point: 184-185 ° C

Example 1.
Process for producing 6-ethoxycarbonylamino-3- (ethylsulfonyl) -2- (5- (trifluoromethylthio) benzoxazol-2-yl) quinoline (Compound No. 3-6)

6-Amino-3- (ethylsulfonyl) -2- (5- (trifluoromethylthio) benzoxazol-2-yl) quinoline (30 mg, 0.07 mmol) prepared in the previous step was added to THF (tetrahydrofuran) (2.0 mL). ), Sodium hydrogen carbonate aqueous solution (2.0 mL) and ethyl chloroformate (36 mg, 0.33 mmol) were added, and the mixture was stirred at room temperature for 2 hours. After the reaction, ethyl acetate was added. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain the desired product (30 mg, 94%).
Melting point: 261-262 ° C

Example 2
Process for producing 7-ethoxycarbonylamino-3- (ethylsulfonyl) -2- (5- (trifluoromethylthio) benzoxazol-2-yl) quinoline (Compound No. 4-6)

7-Bromo-3- (ethylsulfonyl) -2- (5- (trifluoromethylthio) benzoxazol-2-yl) quinoline (20 mg, 0.04 mmol) prepared by the method described in WO2016 / 091731 was dissolved in toluene. (0.4 mL), ethyl carbamate (7.0 mg, 0.08 mmol), cesium carbonate (26 mg, 0.08 mmol), tris (dibenzylideneacetone) dipalladium (4.0 mg, 0.004 mmol), Xantphos (5.0 mg, 0.010 mmol) was added, and the mixture was stirred at 90 ° C. for 2 hours under an argon atmosphere. The reaction mixture was subjected to silica gel column chromatography to obtain the desired product (18 mg, 84%).
Melting point: 109-110 ° C

Example 3 FIG.
3-Ethylsulfonyl-7-ethoxycarbonylamino-2- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl) quinoline (Compound No. 2-6) Manufacturing method

7-Bromo-3- (ethylsulfonyl) -2- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine-2 prepared by the method described in WO2016 / 091731 -Yl) quinoline (50 mg, 0.10 mmol) dissolved in toluene (1.0 mL), ethyl carbamate (18 mg, 0.20 mmol), cesium carbonate (65 mg, 0.20 mmol), tris (dibenzylideneacetone) di Palladium (9.2 mg, 0.010 mmol) and Xantphos (13 mg, 0.024 mmol) were added, and the mixture was stirred at 90 ° C. for 2 hours under an argon atmosphere. The reaction mixture was subjected to silica gel column chromatography to obtain the desired product (42 mg, 83%).
Melting point: 223-224 ° C

Reference Example 3.
Process for producing 7-bromo-3-ethylsulfonyl-2- (5- (trifluoromethylsulfonyl) benzoxazol-2-yl) quinoline

7-Bromo-3- (ethylsulfonyl) -2- (5- (trifluoromethylthio) benzoxazol-2-yl) quinoline (320 mg, 0.58 mmol) of ethyl acetate prepared by the method described in WO2016 / 091731 (6 mL) In a solution, m-chloroperbenzoic acid (390 mg, 1.28 mmol) was added under ice cooling, and the mixture was warmed to room temperature and stirred for 2 hours. Saturated sodium thiosulfate solution was poured into the reaction mixture, extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain the desired product (214 mg, 67%).
Melting point: 245-246 ° C

Example 4
Process for producing 7-ethoxycarbonylamino-3- (ethylsulfonyl) -2- (5- (trifluoromethylsulfonyl) benzoxazol-2-yl) quinoline (Compound No. 4-26)

7-Bromo-3-ethylsulfonyl-2- (5- (trifluoromethylsulfonyl) benzoxazol-2-yl) quinoline (100 mg, 0.18 mmol) was dissolved in toluene (2 mL) and ethyl carbamate (32 mg, 0.36 mmol), tris (dibenzylideneacetone) dipalladium (18 mg, 0.020 mmol), Xantphos (24 mg, 0.043 mmol), cesium carbonate (120 mg, 0.36 mmol) were added, and the mixture was added at 90 ° C. under an argon atmosphere. Stir for hours. The reaction mixture was subjected to silica gel column chromatography to obtain the desired product (39 mg, 39%).
Melting point: 107-108 ° C

Example 5 FIG.
Preparation of 7-Ethoxycarbonylamino-3-ethylsulfonyl-2- (6-pentafluoroethyl-3-methyl-3H-imidazo [4,5-C] pyridazin-2-yl) quinoline (Compound No. 6-6) Method

7-Bromo-3-ethylsulfonyl-2- (6-pentafluoroethyl-3-methyl-3H-imidazo [4,5-C] pyridazin-2-yl) quinoline (50 mg, 0.09 mmol) in toluene (1 0.0 mL), ethyl carbamate (16 mg, 0.18 mmol), cesium carbonate (59 mg, 0.18 mmol), tris (dibenzylideneacetone) dipalladium (8.2 mg, 0.009 mmol), Xantphos (12 mg, 0.022 mmol) was added, and the mixture was stirred at 90 ° C. for 2 hours under an argon atmosphere. The reaction mixture was subjected to silica gel column chromatography to obtain the desired product (40 mg, 78%).
Melting point: 227-228 ° C

Example 6
7-((N-ethoxycarbonyl) -N- (2,2,2-trifluoroethyl) amino) -3- (ethylsulfonyl) -2- (6-trifluoromethyl-3-methyl-3H-imidazo [ 4,5-b] pyridin-2-yl) quinoline (Compound No. 2-10)

7- (N-ethoxycarbonylamino) -3- (ethylsulfonyl) -2- (6-trifluoromethyl-3-methyl-3H-imidazo [4,5-b] pyridin-2-yl) quinoline (20 mg, 0.04 mmol) in DMF (dimethylformamide) (0.1 mL) was added sodium hydride (3 mg, 0.06 mmol), stirred for 10 minutes, and then 2,2,2-trifluorotrifluoromethanesulfonic acid. Ethyl (14 mg, 0.06 mmol) was added, the temperature was raised to 60 ° C., and the mixture was stirred for 5 hours. After the reaction, water was added, extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain the desired product (13 mg, 56%).
Melting point: 81-82 ° C

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 Mixture 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, test examples of the present invention will be shown, but the present invention is not limited thereto.

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 quinoline compound having a carbamate group represented by the general formula (1) 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 potted Chinese cabbage and air-dried. Was stored in a greenhouse, and the number of parasites of the peach aphid parasitic on each Chinese cabbage on the 6th day after the spraying of the drug was investigated, 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 area T: Number of parasites after spraying in the treated area Ca: Number of parasites before spraying in the untreated area C: Number of parasites after spraying in the untreated area

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

As a result, the compounds of the present invention 1-6, 2-1, 2-6, 2-7, 2-10, 2-11, 2-16, 2-21, 3-1, 3-6, 3-7 3-16, 4-6, 4-7, 4-26, 4-27, 4-46, 6-6, 6-7, 6-26, 6-27, 7-1, 7-2, and 7-3 showed the activity of A. , A activity was shown.

Test Example 2 Insecticidal test for Laodelphax striatella The quinoline compound having a carbamate group represented by the general formula (1) 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: Nihonbare) was soaked for 30 seconds, air-dried, put into a glass test tube, inoculated with 10 each of the 3 Japanese beetles, and then plugged with cotton. After 8 days of inoculation, the number of live and dead insects was investigated, and the corrected death rate was as follows: And was determined according to the following criteria.

Judgment criteria A ... 100% corrected death rate
B ... Corrected death rate 99% to 90%
C: Corrected death rate 89% -80%
D: Corrected death rate 79% -50%

As a result, the compounds of the present invention 1-6, 2-1, 2-6, 2-7, 2-10, 2-11, 2-16, 2-21, 3-1, 3-6, 3-7 3-16, 4-6, 4-7, 4-26, 4-27, 4-46, 6-6, 6-7, 6-26, 6-27, 7-1, 7-2, and 7-3 showed the activity of A. Showed the activity of A.

Test Example 3 Insecticidal test against Plutella xylostella Sponge seedlings are allowed to lay eggs and lay eggs, and carpate seedlings with spawning eggs two days after the release are expressed by the carbamate group represented by the general formula (1) of the present invention. A quinoline compound having a quinoline compound as an active ingredient was immersed in a chemical solution diluted to 500 ppm for about 30 seconds, air-dried, and left 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 by the following formula, and the determination was made according to the criteria of Test Example 2. 1 ward, 10 heads, 3 systems.

As a result, the compounds of the present invention 1-6, 2-1, 2-6, 2-7, 2-10, 2-11, 2-16, 2-21, 3-1, 3-6, 3-7 3-16, 4-6, 4-7, 4-26, 4-27, 4-46, 6-6, 6-7, 6-26, 6-27, 7-1, 7-2, and 7-3 showed the activity of A.

The compound according to the present invention has an excellent control effect against a wide range of agricultural and horticultural pests and is useful.

Claims (6)

1. General formula (1)
   

   

   {Wherein R ¹ is (a1) (C ₁ -C ₆ ) alkyl group; (a2) halo (C ₁ -C ₆ ) alkyl group; (a3) (C ₂ -C ₆ ) alkenyl group; (a4 ) _{(C 2} -C ₆₎ alkynyl group; _{and; (a5) (C 3 -C} 6) cycloalkyl group; or _{(a6) (C 3 -C 6} ) cycloalkyl _{(C 1} -C ₆₎ alkyl group .
   R ² represents (b1) a hydrogen atom; (b2) a (C ₁ -C ₆ ) alkyl group; (b3) a halo (C ₁ -C ₆ ) alkyl group; (b4) (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆₎ alkyl group; (b5) cyano _{(C 1} -C ₆₎ alkyl _{group; (b6) (C 3 -C} 6) cycloalkyl group; or _{(b7) (C 3 -C 6} ) cycloalkyl ( C ₁ -C ₆ ) alkyl group;
   R ³ is (c1) halogen atom; (c2) cyano group; (c3) nitro group; (c4) (C ₁ -C ₆ ) alkyl group; (c5) (C ₁ -C ₆ ) alkoxy group; ) (C ₂ -C ₆ ) alkenyloxy group; (c7) (C ₂ -C ₆ ) alkynyloxy group; (c8) halo (C ₁ -C ₆ ) alkyl group; (c9) halo (C ₁ -C ₆₎ (C10) halo (C ₂ -C ₆ ) alkenyloxy group; (c11) halo (C ₂ -C ₆ ) alkynyloxy group; (c12) (C ₁ -C ₆ ) alkylthio group; (c13) (C ₁ -C ₆ ) alkylsulfinyl group; (c14) (C ₁ -C ₆ ) alkylsulfonyl group; (c15) halo (C ₁ -C ₆ ) alkylthio group; (c16) halo (C ₁ -C ₆ ) An alkylsulfinyl group; or (d17) a halo (C ₁ -C ₆ ) alkylsulfonyl group.
   A represents an oxygen atom or N—R ⁴ (wherein R ⁴ represents (e1) a hydrogen atom; or (e2) (C ₁ -C ₆ ) an alkyl group); and A ¹ and A ² may be the same or different and each represents CH or a nitrogen atom, m represents 0, 1, or 2, and n represents 0, 1, or 2. } A quinoline compound or a salt thereof.
2. The quinoline compound or a salt thereof according to claim 1, wherein A is an oxygen atom.
3. The quinoline compound or a salt thereof according to claim 1, wherein A is N-Me.
4. An agricultural and horticultural insecticide comprising the quinoline compound or a salt thereof according to any one of claims 1 to 3 as an active ingredient.
5. A method for using an agricultural and horticultural insecticide, which comprises treating a plant or soil with an effective amount of the quinoline compound or a salt thereof according to any one of claims 1 to 3.
6. An animal ectoparasite control agent comprising the quinoline compound according to any one of claims 1 to 3 or a salt thereof as an active ingredient.