Pyridyl alkoxy pyrimidine compound and use thereof

Abstract

The invention belongs to the technical field of pesticides, and particularly relates to a pyridyl alkoxy pyrimidine compound and a use thereof. The compound is as shown as formula I: wherein X and Y independently represent hydrogen, hydroxyl, alkyl, alkoxy, enoxy, alkynyloxy etc.; Z represents hydrogen, halogen, cyano, amino, nitro, formyl, cyanoalkyl, hydroxyalkyl, alkyl, alkenyl, alkynyl, etc. The compound or a salt thereof has an excellent effect as an insecticide for agricultural gardening.

Description

A pyridylalkoxypyrimidine compound and its application Technical Field

[0001] The present invention belongs to the technical field of pesticides, and in particular relates to a pyridylalkoxypyrimidine compound and application thereof. Background Art

[0002] In the agricultural and horticultural fields, crop damage caused by pests remains severe, and due to the emergence of pests resistant to existing agents, there is a growing demand for novel agricultural and horticultural insecticides and acaricides. The increasing number of elderly people employed in agriculture has led to a demand for labor-saving application methods, and there is also a need for agricultural and horticultural insecticides and acaricides with properties suitable for these application methods.

[0003] Summary of the Invention

[0004] In order to solve the above problems existing in the prior art, the present invention provides a pyridylalkoxypyrimidine compound or a salt thereof, which has excellent effects as an agricultural and horticultural insecticide.

[0005] The technical solution adopted in the present invention is as follows:

[0006] A pyridylalkoxypyrimidine compound or a salt thereof, as shown in Formula I:

[0007] wherein X and Y independently represent hydrogen, hydroxy, alkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, cycloalkylalkyloxy, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, cycloalkylalkylthio, or represents -CH=CH-R, -CH=NOR or cycloalkyl;

[0008] Z represents hydrogen, halogen, cyano, amino, nitro, formyl, cyanoalkyl, hydroxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkylthio, alkylamino, haloalkoxy, haloalkylthio, alkylcarbonyl, alkoxycarbonyl, alkoxyalkyl, haloalkoxyalkyl, alkylaminoalkyl, aryl, heterocyclyl, arylalkyl or heterocyclylalkyl, wherein the alkyl, alkenyl or alkynyl is optionally substituted with halogen, and the cycloalkyl, cycloalkenyl, heterocyclyl or aryl is optionally substituted with at least one group selected from alkyl, haloalkyl, alkylsulfonyl, alkylacyl, alkylacyloxy, alkoxyacyl, halogen, alkoxy, alkylthio, cyano, amino or alkylamino;

[0009] R each independently represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl or arylalkyl; wherein the cycloalkyl, cycloalkenyl, heterocyclyl or aryl group is optionally substituted by at least one group selected from alkyl, haloalkyl, alkylsulfonyl, alkylacyl, alkylacyloxy, alkoxyacyl, halogen, alkoxy, alkylthio, cyano, amino or alkylamino.

[0010] In a specific embodiment, X and Y independently represent hydrogen, hydroxy, C1-C8 alkyl, C1-C8 alkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C3-C8 cycloalkyloxy, C3-C8 cycloalkylC1-C8 alkyloxy, C1-C8 alkylthio, C2-C8 alkenylthio, C2-C8 alkynylthio, C3-C8 cycloalkylthio, C3-C8 cycloalkylC1-C8 alkylthio, or represents -CH=CH-R, -CH=NOR or C3-C8 cycloalkyl;

[0011] Z represents hydrogen, halogen, cyano, amino, nitro, formyl, cyano C1-C8 alkyl, hydroxy C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, halogenated C1-C8 alkoxy, halogenated C1-C8 alkylthio, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy C1-C8 alkyl, halogenated C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylamino C1-C8 Alkyl, aryl, heterocyclyl, arylC1-C8 alkyl or heterocyclylC1-C8 alkyl, wherein the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally substituted with halogen, and the C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl or aryl is optionally substituted with at least one group selected from C1-C8 alkyl, halo-substituted C1-C8 alkyl, C1-C8 alkylsulfonyl, C1-C8 alkylacyl, C1-C8 alkylacyloxy, C1-C8 alkoxyacyl, halogen, C1-C8 alkoxy, C1-C8 alkylthio, cyano, amino or C1-C8 alkylamino;

[0012] R each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl or arylC1-C8 alkyl; wherein the C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl or aryl is optionally substituted by at least one group selected from C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkylsulfonyl, C1-C8 alkylacyl, C1-C8 alkylacyloxy, C1-C8 alkoxyacyl, halogen, C1-C8 alkoxy, C1-C8 alkylthio, cyano, amino or C1-C8 alkylamino.

[0013] In another embodiment, X and Y each independently represent hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkyloxy, C3-C6 cycloalkylC1-C6 alkyloxy, C1-C6 alkylthio, C2-C6 alkenylthio, C2-C6 alkynylthio, C3-C6 cycloalkylthio, C3-C6 cycloalkylC1-C6 alkylthio, or represents -CH=CH-R, -CH=NOR or C3-C6 cycloalkyl;

[0014] Z represents hydrogen, halogen, cyano, amino, nitro, formyl, cyano C1-C6 alkyl, hydroxy C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, halogenated C1-C6 alkoxy, halogenated C1-C6 alkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy C1-C6 alkyl, halogenated C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylamino C1-C6 Alkyl, aryl, heterocyclyl, arylC1-C6 alkyl or heterocyclylC1-C6 alkyl, wherein the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally substituted with halogen, and the C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl or aryl is optionally substituted with at least one group selected from C1-C6 alkyl, halo-substituted C1-C6 alkyl, C1-C6 alkylsulfonyl, C1-C6 alkylacyl, C1-C6 alkylacyloxy, C1-C6 alkoxyacyl, halogen, C1-C6 alkoxy, C1-C6 alkylthio, cyano, amino or C1-C6 alkylamino;

[0015] R each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl or arylC1-C6 alkyl; wherein the C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl or aryl is optionally substituted by at least one group selected from C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkylsulfonyl, C1-C6 alkylacyl, C1-C6 alkylacyloxy, C1-C6 alkoxyacyl, halogen, C1-C6 alkoxy, C1-C6 alkylthio, cyano, amino or C1-C6 alkylamino.

[0016] In the definitions of compounds represented by the above general formula and in all the following structural formulas, the technical terms used, whether used alone or in compound terms, represent the following substituents: Alkyl groups having more than two carbon atoms may be straight-chain or branched. Examples of alkyl groups include, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl, such as n-propyl or isopropyl; C4 alkyl-butyl, such as n-butyl, isobutyl, tert-butyl, or 2-butyl; C5 alkyl-pentyl, such as n-pentyl; and C6 alkyl-hexyl, such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, examples of alkenyl groups include vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. Alkynyl is for example ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl.Multiple bonds can be in any position of each unsaturated group.Cycloalkyl is a carbocyclic saturated ring system with for example three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.Similarly, cycloalkenyl is a monocyclic alkenyl with for example three to six carbocyclic ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, wherein double bonds can be in any position.Halogen is fluorine, chlorine, bromine or iodine.

[0017] Unless otherwise specified, the "aryl" mentioned in the present invention includes but is not limited to phenyl, naphthyl, The "heterocyclic group" includes but is not limited to saturated or unsaturated non-aromatic cyclic groups etc., and also include but are not limited to heteroaryl, i.e. an aromatic cyclic group containing, for example, 3 to 6 ring atoms and optionally fused to a benzo ring, wherein 1 to 4 (e.g. 1, 2, 3 or 4) heteroatoms in the ring atoms are selected from oxygen, nitrogen and sulfur, for example

[0018] If a group is substituted by a group, this is understood to mean that the group is substituted by one or more identical or different groups selected from the groups mentioned. Furthermore, identical or different substituent characters contained in identical or different substituents are independently selected and may be identical or different. The same applies to ring systems formed from different atoms and units. At the same time, compounds known to those skilled in the art to be chemically unstable under standard conditions are excluded from the scope of the claims.

[0019] In addition, unless otherwise specified, the term "substituted by at least one group" as used herein refers to being substituted by 1, 2, 3, 4 or 5 groups; groups (including heterocyclic groups, aryl groups, etc.) without a specific connection position can be connected at any position, including the position connected to C or N; if it is substituted, the substituent can also be substituted at any position as long as it complies with the chemical bond connection rules. For example, a heteroaryl group substituted by 1 methyl group Can represent wait.

[0020] Examples of salts of the pyridylalkoxypyrimidine compounds represented by Formula I of the present invention include: inorganic acid salts such as hydrochlorides, sulfates, nitrates, phosphates, etc., organic acid salts such as acetates, trifluoroacetates, fumarates, maleates, oxalates, methanesulfonates, benzenesulfonates, p-toluenesulfonates, etc.; and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, trimethylammonium, etc.

[0021] The pyridylalkoxypyrimidine compound or its salt represented by Formula I of the present invention may contain one or more asymmetric centers in the structural formula, and in some cases, two or more optical isomers and diastereomers may exist. The present invention includes any of such optical isomers and mixtures thereof in any proportion. In addition, the pyridylalkoxypyrimidine compound or its salt represented by Formula I of the present invention may have two types of geometric isomers derived from carbon-carbon double bonds in the structural formula. The present invention includes all geometric isomers and mixtures thereof in any proportion.

[0022] The present invention also provides a method for preparing the pyridylalkoxypyrimidine compound or its salt, comprising the following steps:

[0023] (1) Compound II is subjected to hydrogenation reaction to obtain compound I. The chemical reaction equation is as follows:

[0024] Alternatively, (2) Compound III and Compound IV undergo a substitution reaction to obtain Compound I, and the chemical reaction equation is as follows:

[0025] Alternatively, (3) Compound V and Compound IV are first subjected to a substitution reaction to obtain Compound VI, and Compound VI is then reacted with VII to obtain Compound I. The chemical reaction equation is as follows:

[0026] wherein Hal independently represents a halogen, and the substituents X, Y and Z are as defined above.

[0027] In one embodiment, the step (1) is carried out in the presence of formic acid or hydrogen, a base, a catalyst and a solvent.

[0028] In one embodiment, the first step in step (2) and step (3) is carried out in the presence of a base and a solvent.

[0029] In one embodiment, the second step in step (3) is carried out in the presence of a catalyst, a base and a solvent.

[0030] In one embodiment, the catalyst in the second step of steps (1) and (3) is Pd(dppf)Cl2·CH2Cl2, Pd(dppf)Cl2, Pd(PPh3)4, PdCl2, Pd(OAc)2, tricyclohexylphosphine palladium acetate, Pd(PPh3)2Cl2 or NiCl2(dppf).

[0031] In another specific embodiment, the solvent in steps (1), (2) and (3) is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, toluene, water, dichloromethane or ethyl acetate.

[0032] In another specific embodiment, the base in steps (1), (2) and (3) is selected from at least one of an inorganic base (such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KF, CsF, KOAc, AcONa, K3PO4, t-BuONa, EtONa, NaOH, KOH, NaOMe, NaH, KH, etc.) or an organic base (such as DMAP, pyrazole, triethylamine, DIEA, etc.).

[0033] The preparation method of the compound of the present invention can also be obtained by referring to WO2013 / 115391.

[0034] The present invention also provides the aforementioned intermediate compound II, III, IV, V or VI.

[0035] The agricultural and horticultural insecticide containing the pyridylalkoxypyrimidine compound represented by formula I of the present invention or a salt thereof as an active ingredient is suitable for controlling various pests, such as agricultural and horticultural pests, stored grain pests, sanitary pests, nematodes, etc., which are harmful to rice, fruit trees, vegetables, other crops, flowers and ornamental plants.

[0036] Examples of the above-mentioned harmful insects, nematodes and the like include the following.

[0037] Examples of pests of the order Lepidoptera include: Parasa consocia, Anomis mesogona, Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, Spodoptera exempta, Hyphantria cunea, Ostrinia furnacalis, Pseudaletia separata, Tinea translucens, Bactra furfurana, Parnara guttata, Marasmia exigua, Parnara guttata, Sesamia inferens, Brachmia tricolor triannulella), Monema flavescens, Trichoplusia ni, Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Cephonodes hylas, Helicoverpa armigera, Phalerodonta manleyi, Eumeta japonica, Pieris brassicae, Malacosoma neustria testacea, Stathmopoda masinissa, Cuphodes diospyrosella, Archips xylosteanus, Agrotis segetum, Tetramoera schistaceana, Papilio serrata machaonhippocrates), yellow-spotted bat moth (Endoclyta sinensis), silver-striped miner (Lyonetia prunifoliella), golden-striped miner (Phyllonorycterringoneella), chestnut-white tortoise moth (Cydia kurokoi), chestnut-green tortoise moth (Eucenogenesaestuosa), Lobesia botrana (Grape Flower-winged Moth), Latoia sinica (Chinese Green Moth), Euzophera batangensis (Dark-spotted Bark Moth), Phalonidia mesotypa (Sagittaria sagittifolia), Spilosoma imparilis (Mulberry Spotted Moth), Glyphodes pyloalis (Mulberry Silkworm), Olethreutes mori (Mulberry Leaf Roller), Tineola bisselliella (Curtain Moth), Endoclyta excrescens (Bat Moth), Nemapogon granellus (Grain Moth), Synanthedon hector (Apple Clearwing Moth), Cydia pomonella (Apple Codling Moth), Plutella xylostella (Diamondback Moth), Cnaphalocrocis medinalis (Rice Leaf Roller), Sesamia calamistis (Stalk Borer), Scirpophaga incertulas (Yellow Stem Borer), Pediasia teterrellus), Potato Tuber Moth (Phthorimaea operculella), Apple Ant Boat Moth (Stauropus fagipersimilis), Bean Pod Borer (Etiella zinckenella), Beet Armyworm (Spodoptera exigua), White-spotted Bat Moth (Palpifers exnotata), Gray-winged Armyworm (Spodoptera mauritia), Rice White Borer (Scirpophaga innotata), Eight-character Cutworm (Xestia c-nigrum), Pale Sword-striped Gray-winged Armyworm (Spodoptera depravata), Mediterranean Stem Borer (Ephestia kuehniella), Plum Wireworm (Angerona prunaria), Moon Fan Boat Moth (Clostera anastomosis), Soybean Armyworm (Pseudoplusia includens), Matsumuraeses falcana, Tobacco Armyworm (Helicoverpa assulta), Black-spotted Spodoptera (Autographa nigrisigna), Agrotis ipsilon, Euproctis pseudoconspersa, Adoxophyes orana, Caloptilia theivora, Homonamagnanima), Ephestia elutella (Tobacco), Eumeta minuscula (Tea), Clostera anachoreta (Poplar), Heliothis maritima (Alfalfa), Sparganothis pilleriana (Grape), Busseola fusca (Maize), Euproctis subflava (Folded Banded), Biston robustum (Brown), Heliothis zea (American Cotton), Aedi aleucomelas (Sweet Potato), Narosoideus flavidorsalis (Pear), Viminia rumicis (Pear), Bucculatrix pyrivorella (Bucculatrix pyrivorella), Grapholita molesta (Pear), Spulerina astaurota (Pear), Ectomyelois pyrivorella (Pear), Chilo suppressalis (Chilo suppressalis), Onion Diamondback Moth (Acrolepiopsis sapporensis), Indian Meal Borer (Plodia interpunctella), Cabbage Heart Borer (Hellula undalis), Wheat Moth (Sitotroga cerealella), Spodoptera litura, Eucosma aporema, Strawberry Long-winged Moth (Acleris comariana), Scopelodes contractus, Orgyia thyellina, Spodoptera frugiperda, Ostrinia zaguliaevi, Naranga aenescens, Andraca bipunctata, Grape Clearwing Moth (Paranthrene regalis), Acosmeryx castanea, Grape Leaf Miner (Phyllocnistis toparcha), Grape Berry Moth (Endopiza viteana), and Eupoecillia ambiguella), soybean armyworm (Anticarsia gemmatalis), tobacco moth (Cnephasia cinereipalpana), gypsy moth (Lymantriadispar), Dendrolimus spectabilis, Leguminivora glycinivorella, Maruca testulalis, Matsumuraeses phaseoli, Caloptilia soyella, Phyllocnistis citrella, Omiodes indicate, Archips fuscocupreanus, Acanthoplusia agnata, Bambalina sp., Carposina niponensis, Conogethes punctiferalis, Synanthedon sp., Lyonetia clerkella, Papilio helenus, Colias erate poliographus, Phalera flavescens), Pieridae such as Pieris rapae crucivora and Pieris rapae, Euproctis similis, Acrolepiopsis suzukiella, Ostrinia nubilalis, Mamestra brassicae, Ascotis selenaria, Phtheochroides clandestina, Hoshinoa adumbratana, Odonestis prunijaponensis, Triaena intermedia, Adoxophyes orana fasciata, Grapholita inopinata, Spilonota ocellana, Spilonota scapularis, and many other insects. lechriaspis), pear star moth (Illiberispruni), apple silver moth (Argyresthia conjugella), fierce flower moth (Caloptilia zachrysa), pear yellow moth (Archipsbreviplicanus), small bridge borer (Anomis flava), pink bollworm (Pectinophora gossypiella), cotton leaf roller (Notarcha derogata), melon silk borer (Diaphania indica), tobacco budworm (Heliothis virescens), and golden spot borer (Earia scupreoviridis).

[0038] Examples of harmful insect pests of the order Hemiptera include: Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, Aeschynteles maculatus, Creontiades pallidifer, Dysdercus cingulatus, Chrysomphalus ficus, Aonidiella aurantii, Graptopsaltria nigrofuscata, Blissus leucopterus, Icerya purchasi, Piezodorus hybneri, Lagynotomus spp. elongatus), white-winged leafhopper (Thaia subrufa), black rice stink bug (Scotinophara lurida), rose aphid (Sitobion ibarae), rock stink bug (Stariodes iwasakii), coconut round shield scale (Aspidiotus destructor), pale Thai blind bug (Taylorilygus pallidulus), apricot gall aphid (Myzusmumecola), plum white scale (Pseudaulacaspis prunicola), pea aphid (Acyrthosiphon pisum), stink bug (Anacanthocoris striicornis), jumping blind bug (Ectometopterus micantulus), Japanese two-starred bug (Eysarcoris lewisi), giant leaf-footed bug (Molipteryx fuliginosa), large green leafhopper (Cicadella viridis), red-bellied constrictor aphid (Rhopalosophum rufiabdominalis), black wax scale (Saissetia oleate), greenhouse whitefly (Trialeurodes vaporariorum), oak leafhopper (Aguriahana quercus), grass bugs (Lygus spp.), birch aphid (Euceraphis punctipennis), citrus scale (Andaspis kashicola), orange wax scale (Coccuspseudomagnoliarum), Cavelerius saccharivorus, Galeatus spinifrons, Macrosiphoniella sanborni, Aonidiella citrina, Halyomorpha mista, Stephanitis fasciicarina, Trioza camphorae, Leptocorisa chinensis, Trioza quercicola, Uhlerites latius, Erythroneura comes, Paromius exiguus, Duplaspidiotus claviger, Nephotettix nigropictus, Halticiellus spp. insularis), Perkinsiella saccharicida (Sugarcane Flat-horned Planthopper), Psylla malivorella (Apple Psylla), Anomomeura mori (Mulberry Psylla), Pseudococcus longispinis (Long-tailed Mealybug), Pseudaulacaspis pentagona (Mulberry White Shield Scale), Pulvinaria kuwacola (Mulberry Wax Scale), Apolygus lucorum (Green Migration Bug), Togo hemipterus (Cucurbit Long-tailed Bug), Toxoptera aurantii (Citrus Aphid), Saccharicoccus sacchari (Sugar Meal Scale), Geoica lucifuga (Sugarcane Root Aphid), Numata muiri (Bottlehead Planthopper), Comstockaspis perniciosa (Pear Round Scale), Unaspis citri (Citrus Arrow Shield Scale), Aulacorthum solani (Tomato Groove Netless Aphid), Eysarcoris ventralis), silverleaf whitefly (Bemisia argentifolii), large white leafhopper (Cicadella spectra), spring ivy round shield scale (Aspidiotus hederae), millet-margined stink bug (Liorhyssus hyalinus), black-backed psyllid (Calophya nigridorsalis), white-backed rice hopper (Sogatellafurcifera), Megoura crassicauda, ​​Brevicoryne brassicae, Aphis glycines, Leptocorisa oratorius, Nephotettix virescens, Uroeucon formosanum, Cyrtopeltis tennuis, Bemisia tabaci, Lecanium persicae, Parlatoria theae, Pseudaonidia paeoniae, Empoasca onukii, Plautia stali, Dysaphis tulipae, Macrosiphum euphorbiae), Stephanitis pyrioides, Ceroplastes ceriferus, Parlatoria camelliae, Apolygus spinolai, Nephotettix cincticeps, Glaucias subpunctatus, Orthotylus flavosparsus, Rhopalosiphum maidis, Peregrinus maidis, Eysarcoris parvus, Cimex lectularius, Psylla abieti, Nilaparvata lugens, Psylla tobirae, Eurydema rugosum, Schizaphis piricola), Psylla pyricola, Parlatoreopsis pyri, Stephanitis nashi, Dysmicoccus wistariae, Lepholeucaspis japonica, Sappaphispiri, Lipaphis erysimi, Neotoxopteraformosana), Rhopalosophum nymphaeae, Edwardsianarosae, Pinnaspisaspidistrae, Psylla alni, Speusotettix subfusculus, Alnetoidia alneti, Sogatella panicicola, Adelphocoris lineolatus, Dysdercus poecilus, Parlatoria ziziphi, Uhlerites debile, Laodelphax striatellus, Eurydema pulchrum, Cletus trigonus, Clovia punctata, Empoasca sp.), Coccus hesperidum, Pachybrachius luridus, Planococcus kraunhiae, Stenotus binotatus, Arboridia apicalis, Macrosteles fascifrons, Dolycoris baccarum, Adelphocoris triannulatus, Viteus vitifolii, Acanthocoris sordidus, Leptocorisa acuta, Macropes obnubilus, Cletus punctiger, Riptortus clavatus, Paratrioza cockerelli), Aphrophora costalis, Lygus disponsi, Lygus saundersi, Crisicoccus pini, Empoasca abietis, Crisicoccus matsumotoi, Aphis craccivora, Megacoptapunctatissimum), Eysarcoris guttiger, Lepidosaphes beckii, Diaphorina citri, Toxoptera citricidus, Planococcus citri, Dialeurodes citri, Aleurocanthus spiniferus, Pseudococcus citriculus, Zyginella citri, Pulvinaria citricola, Coccus discrepans, Pseudaonidia duplex, Pulvinaria aurantii, Lecanium corni, Nezara viridula, Stenodema calcaratum), Rhopalosiphum padi, Sitobion akebiae, Schizaphis graminum, Sorhoanus tritici, Brachycaudus helichrysi, Carpocoris purpureipennis, Myzus persicae, Hyalopterus pruni, Aphis farinose yanagicola, Metasalis populi, Unaspis yanonensis, Mesohomotoma camphorae, Aphis spiraecola, Aphis pomi, Lepidosaphes ulmi, Psylla mali), Heterocordylus flavipes, Myzus malisuctus, Aphidonuguis mali, Orientus ishidai, Ovatus malicolens, Eriosoma lanigerum, Ceroplastes rubens, Aphisgossypii) etc.

[0039] Examples of pests of the order Coleoptera include: Xystrocera globosa, Paederus fuscipes, Eucetonia roelofsi, Callosobruchus chinensis, Cylas formicarius, Hypera postica, Echinocnemus squameus, Oulema oryzae, Donacia provosti, Lissorhoptrus oryzophilus, Colasposoma dauricum, Euscepeps postfasciatus, Epilachna varivestis, Acanthoscelides obtectus, Diabrotica virgifera virgifera), Involvulus cupreus, Aulacophora femoralis, Bruchus pisorum, Epilachna vigintioctomaculata, Carpophilus dimidiatus, Cassida nebulosa, Luperomorpha tunebrosa, Phyllotreta striolata, Psacothea hilaris, Aeolesthes chrysothrix, Curculio sikkimensis, Carpophilus hemipterus, Oxycetonia jucunda, Diabrotica spp.), Mimela splendens, Sitophilus zeamais, Tribolium castaneum, Sitophilus oryzae, Palorus subdepressus, Melolonthajaponica, Anoplophora malasiaca, Neatus picipes, Leptinotarsa ​​decemlineata, Diabrotica undecimpunctata howardi, Sphenophorus venatus, Crioceris quatuordecimpunctata, Conotrachelus nenuphar, Ceuthorhynchidius albosuturalis, Phaedon brassicae, Lasioderma serricorne), Japanese root beetle (Sitonajaponicus), spotted beaked scarab beetle (Adoretus tenuimaculatus), flour beetle (Tenebrio molitor), mealworm monkey beetle (Basilepta balyi), small clover leaf weevil (Hypera nigrirostris), beet flea beetle (Chaetocnema concinna), green scarab beetle (Anomala cuprea), black seven-gill scarab beetle (Heptophylla picea), twenty-eight-spotted ladybug (Epilachna vigintioctopunctata), long-horned leaf beetle (Diabrotica longicornis), flower beetle (Eucetonia pilifera), Agriotes spp.), Attagenus unicolor japonicus, Pagria signata, Anomala rufocuprea, Palorus ratzeburgii, Alphitobius laevigatus, Anthrenus verbasci, Lyctus brunneus, Tribolium confusum, Medythia nigrobilineata, Xylotrechus pyrrhoderus, Epitrix cucumeris, Tomicus piniperda, Monochamus alternatus, Popillia japonica, Epicauta gorhami, Sitophilus zeamais, Rhynchites zeamais heros), vegetable leaf weevil (Listroderes costirostris), four-striped bean weevil (Callosobruchus maculatus), apple frost leaf weevil (Phyllobius armatus), apple blossom weevil (Anthonomus pomorum), copper leaf beetle (Linaeidea aenea), Mexican boll weevil (Anthonomus grandis), etc.

[0040] Examples of pests of the order Diptera include Culexpipienspallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, Hydrellia sasakii, Agromyza oryzae, Hydrellia griseola, Ophiomyia phaseoli, Dacus cucurbitae, Drosophila suzukii, Rhacochlaena japonica, Muscina stabulans, Phoridae such as Megaselia spiracularis, Clogmia albipunctata, Tipula aino), Phormia regina, Culex tritaeniorhynchus, Anopheles sinensis, Hylemya brassicae, Asphondylia sp.), Delia platura, Delia antiqua, Rhagoletis cerasi, Culexpipiens molestus Forskal, Ceratitis capitata, Bradysia agrestis, Pegomya cunicularia, Liriomyza sativae, Liriomyza bryoniae, Chromatomyia horticola, Liriomyza chinensis, Culex quinquefasciatus, Aedes aegypti, Aedes albopictus, Liriomyza trifolii, Liriomyza sativae, Dacus dorsalis, Dacus citrus fruit fly, tsuneonis), red wheat midge (Sitodiplosis mosellana), black-bellied wheat straw fly (Meromuza nigriventris), Mexican fruit fly (Anastrepha ludens), apple fruit fly (Rhagoletis pomonella), etc.

[0041] Examples of pests of the order Hymenoptera include Pristomyrmexpungens, Bethylidae, Monomorium pharaohnis, Pheidole noda, Athalia rosae, Dryocosmus kuriphilus, Formica fuscajaponica, Vespoidea, Athalia infumata, Arge pagana, Athalia japonica, Acromyrmex spp., Solenopsis spp., Arge mali, Ochetellus glaber, and the like.

[0042] Examples of pests of the order Orthoptera include: southern rice grasshopper (Homorocoryphus lineosus), mole cricket (Gryllotalpa sp.), small rice grasshopper (Oxya hyla intricata), small-winged rice grasshopper (Oxya yezoensis), migratory locust (Locusta migratoria), Japanese rice grasshopper (Oxya japonica), northern rice grasshopper (Homorocoryphus jezoensis), yellow-faced oil gourd (Teleogryllus emma), etc.

[0043] Examples of pests of the Thripidae family include: Selenothrips rubrocinctus, Stenchaetothrips biformis, Haplothrips aculeatus, Ponticulothrips diospyrosi, Thrips flavus, Anaphothrips obscurus, Liothrips floridensis, Thrips simplex, Thrips nigropilosus, Heliothrips haemorrhoidalis, Pseudodendrothrips mori, Microcephalothrips abdominalis, Leeuwenia pasanii, Litotetothrips pasaniae, Scirtothrips citri, Haplothrips chinensis, Mycterothrips glycines, Thrips setosus, Scirtothrips dorsalis, Dendrothrips minowai, Haplothrips niger, Thrips tabaci, Thrips alliorum, Thrips hawaiiensis, Haplothrips kurdjumovi, Chirothrips manicatus, Fankliniella intonsa, Thrips coloratus, Franklinella occidentalis, Thrips palmi, Frankliniella lilivora), Lily slipper thrips (Liothrips vaneeckei), etc.

[0044] Examples of pests of the subclass Acari include: Leptotrombidium akamushi, Tetranychus ludeni, Dermacentor variabilis, Tetranychus truncatus, Ornithonyssus bacoti, Demodex canis, Tetranychus viennensis, Tetranychus kanzawai, Ixodes such as Rhipicephalus sanguineus, Cheyletus malaccensis, Tyrophagus putrescentiae, Dermatophagoides farinae, Latrodectus hasseltii, Dermacentor truncatus, and taiwanicus), Acaphylla theavagrans, Polyphagotarsonemus latus, Aculops lycopersici, Ornithonyssus sylvairum, Tetranychus urticae, Eriophyes chibaensis, Sarcoptes scabiei, Haemaphysalis longicornis, Ixodes scapularis, Tyrophagus similis, Cheyletus eruditus, Panonychus citri, Cheyletus moorei, Brevipalpus phoenicis, Octodectes spp. cynotis), European house dust mite (Dermatophagoides ptrenyssnus), brown and yellow blood tick (Haemaphysalis flava), egg-shaped hard tick (Ixodes ovatus), Ryukyu citrus rust mite (Phyllocoptruta citri), apple gall mite (Aculus schlechtendali), apple panonychusulmi), American flower tick (Amblyomma americanum), Dermanyssus gallinae, Robin root mite (Rhyzoglyphus robini), Sancassania sp., etc.

[0045] Examples of termite enoxious pests include: Reticulitermes miyatakei, Incisitermes minor, Coptotermes formosanus, Hodotermopsis japonica, Reticulitermes spp., Reticulitermes flaviceps amamianus, Glyptotermes kushimensis, Coptotermes guangzhoensis, Neotermes koshunensis, Glyptotermes kodamai, Glyptotermes satsumensis, Cryptotermes domesticus, Odontotermes formosanus, Glyptotermes nakaiensis, and Glyptotermes tsutsumensis. nakajimai), Pericapritermes nitobei, Reticulitermess peratus, etc.

[0046] Examples of pests of the order Blattaria include Periplaneta fuliginosa, Blattella germanica, Blattella orientalis, Periplaneta brunnea, Blattella lituricollis, Periplaneta japonica, and Periplaneta Americana.

[0047] Examples of the order Aphaniptera include Pulex irritans, Ctenocephalides felis, and Ceratophyllus gallinae, among others.

[0048] Examples of Nematoda include: Nothotylenchus acris, Aphelenchoides besseyi, Pratylenchus penetrans, Meloidogyne hapla, Meloidogyne incognita, Globodera rostochiensis, Meloidogyne javanica, Heterodera glycines, Pratylenchus coffeae, Pratylenchus neglectus, Tylenchus semipenetrans, etc.

[0049] Examples of Malacozoa include the golden apple snail (Pomacea canaliculata), the giant African land snail (Achatina fulica), the two-lined slug (Meghimatium bilineatum), the Valencia slug (Lehmannina valentiana), the yellow slug (Limax flavus), the snail (Acustadespecta sieboldiana), etc.

[0050] The agricultural and horticultural insecticide of the present invention also has a strong control effect on tomato leaf miner (Tuta absoluta) which is another pest.

[0051] In addition, as the genus Acari that parasitizes animals, which is one of the targets of control, for example, Ixodes such as Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis campanulata, Haemaphysalis concinna, Haemaphysalis japonica, Haemaphysalis kitaokai, Haemaphysalis ias, Ixodes ovatus, Ixodes nipponensis, Ixodes persulcatus, Amblyomma testudinarium, Haemaphysalis spp. megaspinosa), Dermacentor reticulatus and Dermacentor taiwanesis, Ornithonyssus species such as Dermanyssus gallinae, Ornithonyssus sylviarum and Ornithonyssus bursa, Trombicula species such as Eutrombicula wichmanni, Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, Neotrombicula autumnalis, Eutrombicula alfreddugesi and Helenicula miyagawai, carnivorous mites (Cheyletidae) such as Cheyletiella yasguri, Cheyletiella parasitivorax and Cheyletiella blakei,Sarcoptes such as Psoroptes cuniculi, Chorioptes bovis, Otodectescynotis, Sarcoptes scabiei, and Notoedres cati; and Demodicidae such as Demodex canis.

[0052] As fleas, which are another target of control, there can be mentioned, for example, ectoparasitic wingless insects belonging to the order Siphonaptera, more specifically, fleas belonging to the family Pulicidae and the family Ceratephyllus, etc. Examples of fleas belonging to the family Pulicidae include Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaga gallinacea, Xenopsylla cheopis, Leptopsylla segnis, Nosopsyllus fasciatus, Monopsyllus anisus, etc.

[0053] Examples of external parasites, which are another target of control, include: Anoplura such as short-snouted cattle lice (Haematopinus eurysternus), horse sucking lice (Haematopinus asini), sheep lice (Dalmalinia ovis), long-snouted cattle lice (Linognathus vituli), pig lice (Haematopinus suis), pubic lice (Phthirus pubis), and head lice (Pediculus humanus capitis); gnawing lice such as dog gnawing lice (Trichodectes canis); and blood-sucking dipteran insects such as horseflies (Tabanus trigonus), biting midges (Culicoides schultzei), and gnats (Simulium ornatum). In addition, examples of internal parasites include: nematodes such as lungworms, whipworms, tuberculous nematodes, gastric parasites, roundworms and filarial worms; multisegmented tapeworms such as Spirometra erinacei, Diphyllobothrium latum, Dipylidium caninum, Taenia multiceps, Echinococcus granulosus and Echinococcus multilocularis; trematodes such as Schistosoma japonicum and Fasciola hepatica; and protozoa such as coccidia, Plasmodium, Sarcocystis, Toxoplasma and Cryptosporidium.

[0054] The agricultural and horticultural insecticide containing the pyridylalkoxypyrimidine compound represented by Formula I of the present invention or its salt as an active ingredient has a significant control effect on the pests exemplified above, which are harmful to paddy crops, dryland crops, fruit trees, vegetables and other crops, flowers and ornamental plants, etc. Therefore, by applying the agent to cultivation carriers such as breeding facilities, paddy fields, fields, fruit trees, vegetables, other crops or seeds, paddy water, stems and leaves, or soil of flowers and ornamental plants at a time when the pests are expected to appear, before they appear, or when their appearance has been confirmed, the desired effect of the agricultural and horticultural insecticide of the present invention can be exhibited. Specifically, the preferred form of use is the following application utilizing what is called osmotic transfer: the soil for raising seedlings of crops, flowers and ornamental plants, the soil for planting holes during transplantation, the roots of crops, irrigation water, cultivation water in hydroponic cultivation, etc. are treated, and the compound of the present invention is absorbed from the roots through the soil or without passing through the soil.

[0055] The economic plants to which the agricultural and horticultural insecticide of the present invention can be applied are not particularly limited, and for example, plants such as cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.); legumes (soybeans, adzuki beans, broad beans, peas, kidney beans, peanuts, etc.); fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, etc.); vegetables (cabbage, tomatoes, spinach, broccoli, lettuce, onions, green onions (chives, scallions), green peppers, eggplants, strawberries, peppers, okra, leeks, etc.); root vegetables (carrots, potatoes, sweet potatoes, taro, radish, turnips, The following are crops for agricultural use: (1) lotus root, burdock, garlic, Japanese leek, etc.); (2) processing crops (cotton, hemp, sugar beet, hops, sugar cane, beet, olives, rubber, coffee, tobacco, tea, etc.); (3) melons (pumpkin, cucumber, watermelon, cantaloupe, muskmelon, etc.); (4) forage crops (grass, sorghum, timothy, clover, alfalfa, etc.); (5) lawn plants (korean grass, chaff grass, etc.); (6) spice crops (lavender, rosemary, thyme, coriander, pepper, ginger, etc.); (7) flowers (chrysanthemum, rose, carnation, orchid, tulip, lily, etc.); (8) garden trees (gingko, Japanese mountain cherry, peach, etc.); (9) forest trees (Abies sachalinensis, Picea jezoensis, pine, Thujopsis dolabrata, Japanese cedar, Japanese cypress, eucalyptus, etc.);

[0056] The above-mentioned “plants” also include plants that are resistant to herbicides through classical breeding methods or genetic recombination technology, such as: HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr, thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, acetyl-CoA carboxylase inhibitors such as sethoxydim, bromoxynil, dicamba, 2,4-D, etc.

[0057] Examples of "plants" that have been rendered resistant by classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone ALS-inhibiting herbicides such as imazethapyr, which is commercially available under the trade name Clearfield (registered trademark). Similarly, soybeans that have been rendered resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron-methyl by classical breeding methods are commercially available under the trade name STS soybeans. Similarly, examples of plants that have been rendered resistant to acetyl-CoA carboxylase inhibitors such as triketoximes and aryloxyphenoxypropionic acid herbicides by classical breeding methods include SR corn, etc.

[0058] Plants resistant to acetyl-CoA carboxylase inhibitors are described in Proc. Natl. Acad. Sci. USA, Vol. 87, pp. 7175-7179 (1990), etc. In addition, mutant acetyl-CoA carboxylases resistant to acetyl-CoA carboxylase inhibitors are reported in Weed Science, Vol. 53, pp. 728-746 (2005), etc., and plants resistant to acetyl-CoA carboxylase inhibitors can be constructed by introducing such mutant acetyl-CoA carboxylase genes into plants using genetic recombination techniques, or by introducing a mutation that contributes to resistance into the acetyl-CoA carboxylase of a plant. Furthermore, plants resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, and the like can be created by introducing base substitution mutant nucleic acids into plant cells using techniques such as chimeric repair technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318). Site-specific amino acid substitution mutations can be introduced into the plant's acetyl-CoA carboxylase, ALS, and the like. The agricultural and horticultural pesticides of the present invention can also be used in these plants.

[0059] In addition, examples of toxins produced in such genetically modified plants include: insecticidal proteins derived from Bacillus cereus or Bacillus popilliae; insecticidal proteins derived from Bacillus thuringiensis such as delta-endotoxins (e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bbl and Cry9C), VIP1, VIP2, VIP3 and VIP3A; toxins derived from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins and insect-specific neurotoxins; filamentous fungal toxins; plant lectins; lectins; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, potato tuber specific protein (

[0014] The present invention also includes but is not limited to: ribosome inactivating proteins (RIPs) such as ricin, maize-RIP, abrin, rufin, sapolin, and priodin; steroid metabolizing enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, and cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel inhibitors and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase, etc.

[0060] The toxin that produces in such genetically modified plants also comprises: the hybrid toxin of insecticidal protein, the toxin of partial deletion and modified toxin, such as delta-endotoxin protein (for example CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab and Cry35Ab), VIP1, VIP2, VIP3 and VIP3A.Through adopting recombinant technology, the different structural domains of such protein are carried out novel combination, produce hybrid toxin.The toxin of known partial deletion is CrylAb, has wherein deleted the part of aminoacid sequence.In modified toxin, one or more aminoacids of natural toxin are replaced.

[0061] Examples of such toxins and genetically modified plants which are able to synthesize such toxins are described in EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878, WO 03 / 052073 and others.

[0062] The toxins contained in such genetically modified plants can confer resistance to coleopteran pests, hemipteran pests, dipteran pests, lepidopteran pests, and nematodes. The agricultural and horticultural pesticides of the present invention can also be used in combination with these technologies or in a systemic manner.

[0063] To control various pests, the agricultural and horticultural pesticide of the present invention can be applied directly, or after being appropriately diluted or suspended in water, to plants where pests and nematodes are expected to appear, in an amount effective for controlling the pests or nematodes. For example, for pests and nematodes that appear in fruit trees, cereals, vegetables, etc., the pesticide can be sprayed on the stems and leaves, or absorbed by the roots through seed treatments such as soaking seeds in the pesticide, dressing seeds, and Calper treatment; soil treatments such as full soil incorporation, furrow application, bed soil incorporation, cell seedling treatment, planting hole treatment, plant root treatment, top dressing, rice box treatment, and surface application. In addition, the agricultural and horticultural pesticide can also be used by applying it to the culture medium of culture medium (hydroponics), fumigation, or trunk injection.

[0064] The agricultural and horticultural insecticide of the present invention can be applied directly, or after being appropriately diluted or suspended in water, to areas where pests are expected to occur in an amount effective for pest control. For example, it can be applied by spraying on stored grain pests, residential pests, sanitary pests, and forest pests, or by coating, fumigating, or applying poison bait to residential buildings and building materials.

[0065] As methods for seed treatment, conventional methods may be mentioned, for example: a method comprising immersing seeds in a liquid agent obtained by diluting or undiluted a liquid agent or a solid agent to allow the agent to penetrate the seeds, a method comprising adhering a solid agent or a liquid agent to the surface of the seeds by mixing the seeds with the agent or dressing the seeds, a method comprising mixing a sticky carrier (e.g., a resin, a polymer, etc.) with the agent and forming a coating on the seeds, and a method comprising applying the agent near the seeds at the time of planting.

[0066] The "seeds" to be subjected to the seed treatment are plants in the early stages of cultivation for reproduction, and include seeds, corms, tubers, seed pieces, embryos, propagules, bulbs, and plants for vegetative reproduction by cuttings.

[0067] When implementing the methods of the present invention, "soil" and "cultivation medium" for plants refer to the support used to cultivate plants, particularly the support for root growth, and the material is not particularly limited. Any material can be used as long as the plant can grow in it, including, for example, soil, a nursery bed, and water. Other materials that can be used include sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, polymeric substances, rock wool, glass wool, wood chips, and bark.

[0068] As methods of application to the stems and leaves of crops, or stored grain pests, residential pests, sanitary pests, forest pests, etc., the following methods can be mentioned: a method comprising appropriately diluting a liquid preparation (such as an emulsion, a flowable preparation, etc.) or a solid preparation (such as a wettable powder or a water-dispersible granule, etc.) with water and spraying it; a method of spraying a powder; or fumigation, etc.

[0069] As for application to the soil, for example, the following methods can be mentioned: a method comprising applying a liquid preparation diluted or undiluted in water to plant nutrients, nurseries for raising seedlings, etc. of a plant body; a method comprising applying granules to plant nutrients or nurseries for raising seedlings, etc. of a plant body; a method comprising applying powders, wettable powders, water-dispersible granules, granules, etc. before sowing or transplanting and allowing them to be mixed into the soil as a whole; a method comprising applying wettable powders, water-dispersible granules, granules, etc. to planting holes, sowing furrows, etc. before sowing or planting, etc.

[0070] In rice seedling boxes, the formulation can be varied depending on the timing, such as application at sowing, greening, or transplanting. Powders, water-dispersible granules, granules, and other formulations can be used. Application can also be performed by mixing into grove soil, where the grove soil can be mixed with the powder, water-dispersible granules, granules, and the like. For example, the formulation can be mixed into the bed soil, the cover soil, or the entire grove soil. Simply put, the grove soil and the various formulations can be applied in alternating layers.

[0071] Application to paddy fields is typically done by spraying solid formulations such as jumbo sprays, packs, granules, and water-dispersible granules; or liquid formulations such as flowables and emulsions onto flooded fields. Alternatively, suitable formulations can be applied directly or mixed with fertilizers and then injected into the soil during rice planting. Furthermore, liquid formulations such as emulsions and flowables can be applied to water inlets and sources of water flowing to paddy fields, such as irrigation equipment, allowing for effortless application during the water supply process.

[0072] For dryland crops, treatment can be applied to the seeds, the cultivation medium to be placed near the plants, etc., during the period from sowing to the seedling raising stage. For plants to be sown directly in the field, direct seed treatment or treatment of the plant nutrients during cultivation is preferred. Granular formulations or soil injection treatment using a liquid formulation diluted or undiluted with water are also possible. Mixing the granules with the cultivation medium before sowing and sowing the mixture is also a preferred treatment.

[0073] For treatment of plants to be transplanted during the sowing or seedling raising stages, direct seed treatment, soil drench treatment in a nursery using a liquid formulation, or dispersion treatment using a granular formulation are preferred. Furthermore, treatment of the planting hole with granules during transplanting or mixing the granules with the growth medium to be placed near the transplanting site are also preferred.

[0074] The agricultural and horticultural pesticide of the present invention is usually prepared into a convenient form according to the general formulation of agricultural chemicals.

[0075] That is, the aryl alkoxy pyrimidine oxide derivative represented by formula I of the present invention or its salt is blended with a suitable inert carrier and optional adjuvant in an appropriate proportion and prepared into a suitable formulation form by dissolving, dispersing, suspending, mixing, impregnating, adsorbing or adhering, such as a suspension, an emulsifiable concentrate, a soluble concentrate, a wettable powder, a water-dispersible granule, a granule, a powder, a tablet, a filling agent, etc.

[0076] In addition to the active ingredients, the composition of the present invention (agricultural and horticultural pesticide or animal parasite control agent) may also contain additional components commonly used in pesticide formulations or animal parasite control agents as needed. Examples of such additional components include: carriers (such as solid carriers, liquid carriers, etc.), surfactants, dispersants, wetting agents, adhesives, tackifiers, thickeners, colorants, spreaders, adhesives, antifreeze agents, anti-caking agents, disintegrants, stabilizers, etc. If necessary, preservatives, plant debris, etc. may also be used as other additional components. These additional components may be used alone or as mixtures of two or more thereof.

[0077] Examples of solid carriers include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, etc.; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride, etc.; organic solid carriers such as synthetic silicic acid, synthetic silicates, starch, cellulose, plant powders (e.g., sawdust, coconut shells, corn cobs, tobacco stalks, etc.); plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, etc.; urea, hollow inorganic bodies, hollow plastics, fumed silica (white carbon), etc. These can be used alone or in mixtures of two or more thereof.

[0078] Examples of liquid carriers include: alcohols, including monohydric alcohols (such as methanol, ethanol, propanol, isopropanol, butanol, etc.) and polyhydric alcohols (such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, glycerol, etc.); polyol compounds such as propylene glycol ether, etc.; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.; ethers such as diethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.; aliphatic hydrocarbons such as normal paraffin, cycloparaffin, isoparaffin, kerosene, mineral oil, etc.; aromatic hydrocarbons Such as benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, etc.; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc.; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, etc.; lactones such as γ-butyrolactone, etc.; amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidone, etc.; nitriles such as acetonitrile, etc.; sulfur compounds such as dimethyl sulfoxide, etc.; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, castor oil, etc.; water, etc. These can be used alone or in mixtures of two or more thereof.

[0079] Examples of the surfactant to be used as a dispersant or wetting agent include nonionic surfactants such as sorbitan esters of fatty acids, polyoxyethylene sorbitan esters of fatty acids, sucrose esters of fatty acids, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenyl ether-formaldehyde condensates, polyoxyethylene-polyoxypropylene block copolymers, polyoxystyrene-polyoxyethylene block copolymers, alkylpolyoxyethylene-polypropylene block copolymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid biphenyl ethers, polyalkylene benzylphenyl ethers, polyoxyalkylene styrylphenyl ethers, acetylene glycols, polyoxyalkylene-added acetylene glycols, polyoxyethylene ether-type silicones, ester-type silicones, fluorine surfactants, polyoxyethylene castor oil Oil, hydrogenated polyoxyethylene castor oil, etc.; anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylphenyl ether sulfates, polyoxyethylene styrylphenyl ether sulfates, alkylbenzenesulfonates, alkylarylsulfonates, ligninsulfonates, alkylsulfosuccinates, naphthalenesulfonates, alkylnaphthalenesulfonates, salts of naphthalenesulfonic acid formaldehyde condensates, salts of alkylnaphthalenesulfonic acid formaldehyde condensates, fatty acid salts, polycarboxylates, polyacrylic acid salts, N-methyl-fatty acid sarcosinates, resinates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkylphenyl ether phosphates, etc.; cationic surfactants such as laurylamine hydrochloride, stearamide hydrochloride, oleylamine hydrochloride, stearamide acetate, stearamidopropylamine acetate, alkylamine salts (including alkyltrimethylammonium chloride and alkyldimethylbenzalkonium chloride), etc.; amphoteric surfactants such as amino acid or betaine surfactants, etc. These surfactants can be used alone or in mixtures of two or more thereof.

[0080] Examples of binders and thickeners include carboxymethyl cellulose or its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol having an average molecular weight of 6,000-20,000, polyethylene oxide having an average molecular weight of 100,000-5,000,000, phospholipids (e.g., cephalin or lecithin), cellulose powder, dextrin, processed starch, polyaminocarboxylic acid chelate compounds, cross-linked polyvinyl pyrrolidone, maleic acid-styrene copolymers, (meth)acrylic acid copolymers, half esters of polyols and dicarboxylic acid anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffin wax, terpene, polyamide resin, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ether, alkylphenol formaldehyde condensate, and synthetic resin emulsions.

[0081] Examples of the thickener include water-soluble polymers such as xanthan gum, guar gum, diutan gum, carboxymethyl cellulose, polyvinyl pyrrolidone, carboxyvinyl polymers, acrylic acid polymers, starch derivatives and polysaccharides; inorganic fine powders such as high-purity bentonite and fumed silica (white carbon); and the like.

[0082] 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; and the like.

[0083] Examples of the antifreeze agent include polyols such as ethylene glycol, diethylene glycol, propylene glycol, glycerin, and the like.

[0084] Examples of auxiliary agents for preventing caking or promoting disintegration include: polysaccharides (such as starch, alginic acid, mannose and galactose), polyvinyl pyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, sodium hexametaphosphate, metal stearates, cellulose powder, dextrin, methacrylate copolymers, polyvinyl pyrrolidone, polyaminocarboxylic acid chelate compounds, sulfonated styrene-isobutylene-maleic anhydride copolymers and starch-polyacrylonitrile graft copolymers, etc.

[0085] Examples of the stabilizer include: desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol compounds, amine compounds, sulfur compounds, phosphoric acid compounds, etc.; ultraviolet absorbers such as salicylic acid compounds, benzophenone compounds, etc., and the like.

[0086] Examples of preservatives include potassium sorbate, 1,2-benzothiazoline-3-one, and the like.

[0087] In addition, if necessary, functional spreading agents, activity enhancers (such as metabolic decomposition inhibitors, such as piperonyl butoxide), antifreeze agents (such as propylene glycol), antioxidants (such as BHT), ultraviolet absorbers and other adjuvants may also be used.

[0088] The content of the compound as an active ingredient can be varied as needed, and the compound as an active ingredient can be used in a proportion appropriately selected within the range of 0.01 to 90 parts by weight per 100 parts of the agricultural and horticultural agent of the present invention. For example, in a dust, granule, emulsion, or wettable powder, the suitable content of the compound as an active ingredient is 0.01 to 50 parts by weight (0.01 to 50% by weight of the total weight of the agricultural and horticultural insecticide).

[0089] The application amount of the agricultural and horticultural insecticide of the present invention varies depending on various factors, such as the purpose, the pest to be controlled, the growth state of the plant, the tendency of pest emergence, climate, environmental conditions, formulation, application method, application site, and application time. It can be appropriately selected within the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg (in terms of the compound as the active ingredient) per 10 ares, depending on the purpose.

[0090] The agricultural and horticultural pesticides of the present invention can be mixed with other agricultural and horticultural pesticides, acaricides, nematicides, fungicides, biopesticides, etc. to broaden the range of pests and diseases that can be controlled, increase the effective application period, or reduce the dosage. Furthermore, the agricultural and horticultural pesticides of the present invention can be mixed with herbicides, plant growth regulators, fertilizers, etc., depending on the application.

[0091] Examples of other agricultural and horticultural insecticides, acaricides and nematicides to be used for such purposes include: 3,5-dimethylphenylcarbamate (dimethoate), prepared from Bacillus thuringienses aizawai, Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses kurstaki, Bacillus thuringienses tenebrionis, Bacillus thuringienses spp. thuringienses), BPMC, Bt toxin insecticide compounds, CPCBS (carbofuran), dichloroisopropyl ether (dichlorodiisopropyl ether), DD (1,3-dichloropropylene), DDT, NAC, O,O-diethylphosphothioate-O-4-dimethylsulfamoylphenyl ester (DSP), O-ethyl O-4-nitrophenyl phenylthiophosphonate (benthion), tripropyl isocyanurate (TPIC), fluthrin, azadirachtin, azinphos-methyl , acetamiprid, acetamiprid, acetophenone, acephate, abamectin, abamectin-B, sulfamethoxam, amitraz, cotton boll carb, aldicarb, aldisulfone carb, aldrin, α-endosulfan, cis-cypermethrin, prothiocarb, allethrin, chlorpyrifos, isamidofos, isoamidofos, isoxathiophos, isofenphos, isoprocarb: MIPC, ivermectin, imicyafos, imidacloprid, imidacloprid, indoxacarb, cypermethrin, ethiofencarb, ethion, ethiprole Nitrile, etoxazole, ethofenprox, cypermethrin, pyrimithin, emamectin, emamectin benzoate, endosulfan, dextromethrin, oxamectin, sulfoxide, isosulfoxide: ESP, oxbendazole, oxfendazole, potassium oleate, sodium oleate, cadusafos, cartap, carbaryl, butasulfuron, carbofuran, cyhalothrin, methomyl, quinalphos, methoprene, cypermethrin, chlorfenapyr, clothianidin, clofentazine, chlorfenapyr, chlorantraniliprole, chlorpyrifos, chlorpyrifos-methyl, chlorfenapyr Qing, cypermethrin, chlorfenapyr, chlorfluanid, ethyl cypermethrin, chlorobenzoate, trichloroacetic acid, salicylic acid, cypermethrin nitrile: CYAP, cypermethrin, cyfluthrin, cyanamide, highly effective trans-cypermethrin, bendigram, cypermethrin nitrile, vegetable fruit phosphorus, benzyl ether, σ-cypermethrin, cypermethrin: ECP, cypermethrin, dichlorvos: DDVP, disulfoton, dinotefuran, chlorflucythrin, cypermethrin, flucythrin, diflubenzuron, cyflumetofen, fluazifop, tricyclamate, cypermethrin, methyl cypermethrin, dimethoate,Flumethrin, cyromazine, ethyl spinosad, spinosad, spirodiclofen, spirotetramat, spiromesifen, sulfluramid, sulfenthiocarb, sulfenthiopyrid, ζ-cypermethrin, diazinon, fluvalinate, dazomethan, thiacloprid, thiomethoxam, thiodicarb, thiocyclam, thiodimethoate, dimethomorph, thiomethoate, methyl sulfenthiophosphate, DEET, dieldrin, chlorpyrifos, trichlorfon, flumethrin Ester, tetramethrin, butylated pyrimidin, tebufenozide, tebufenpyrad, tefluthrin, fenfluramide, methyl demeton, temephos, deltamethrin, terbufos, bromopyrrole nitrile, tralomethrin, transfluthrin, triazolam, triazuron, salicylate, trichlorfon: DEP, triflumuron, tolfenpyrad, tribromophos: BRP, nithiazine, nitenpyram, fluazifop, polyflumuron, Methoprene, Methylfiprole, Acyril, Parathion, Parathion Methyl, Benzylfen, Chlorfenapyr, Bistrifluron, Dimethoate, Hydrahydrazone, Hydroxypropyl Starch, Benthiocarb, Bifenazate, Bifenthrin, Pymetrozine, Pyraclofos, Pyrazofos, Pyridafenphos, Pyridafen, Pyridafen, Pyridalyl, Pyridafen, Pyridafen, Pyrimidine ... Sulfur: MPP, Paofengsan: PAP, cypermethrin, fenpyroximate, cypermethrin, fenbendazole, thiamethoxam, fluazifop, butyrimphos, buprofezin, furathiocarb, fenacet, fluazinam, fluazinam, fluthiazolin, flutolan, flucythrin, fluvalinate, flupyralid, flufenoxam, flufenoxam, flumethrin, flufenoxam, flutolan, flucythrin, fluvalinate, flupyralid, flufenoxam, flufenoxam, flufenoxam, flutolan ... BPPS, profenofos, profluthrin, propoxur: PHC, bromopyrene, beta-cypermethrin, hexaflumuron, hexathiazolin, heptaclofos, permethrin, isothiamethoxam, benzylpyridinium chloride, sulfamethoxam, benzylpyridinium chloride, chlorpyrifos, benzonitr, benfuracarb, phoxim, phosalone, thiothioate, butyralidone, phosphamidon, phosphamidon, phosmet, phosphamidon, phosmet, polynaphate, fenamiprid, anthracene, phorate, motor oil, malathion, milbemycin, milbemycin-A, milbemycin, aphidicide, methylsulfoxide, methomyl, metaldehyde, metaflumizone, methamidophos, chlorpyrifos Ammonium, methamphetamine, methoxam, methoxazolidinone, DMTP, methyl isothiocyanate, methylneodecanamide, methyl parathion, mefenamic acid, methoxychlor, methoxyfenozide, metofluthrin, methoprene, methicillin, cyfluthrin, mefenphos, monocrotophos, cyhalothrin, ryanodine, lufenuron, resmethrin, lepidomycin, rotenone, levamisole hydrochloride, fenbutatin, morantel tartrate, methyl bromide, tricyclotin, calcium cyanamide, calcium polysulfide, sulfur, nicotine sulfate, etc.

[0092] Examples of agricultural and horticultural fungicides to be used for the same purpose as above include soil fungicides such as aureomycin, oxepiconazole, cypermethrin, fatty acid salts, acibenzolar, benzothiadiazole, azoxystrobin, difop-butyl, indazolesulfamide, aminopropylphosphonic acid, sinotriptyline, allyl alcohol, dodecanol, mancozeb, isothiocyanate, isovaledione, napystrobin, blastifungin, ipconazole, iprodione, isopropanil, isoprofen, imazalil, iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, amide, uniconazole, monoclonal, echlome zole, dichlorvos, ethoconazole, hanlenin, ethimol, manthiocarb, ethoxyquin, thiabendazole, oxathiapiprolin, fluoxepin, oxadixyl, oxycarboxin, 8-hydroxyquinoline copper, oxytetracycline, copper-oxinate, oximidazole, oximidazole-fumarate, quinocetone, octhiazol, furamide, oxamoxadil, metamidine, etc., kasugamycin, mofenac, capramide, carbendazim, carboxin, carvone, quinone, quinocetone, phenoxyquinoline, mite-killing agent, captan, captan, bensulfuron, chlorbenzene, pentachloronitrobenzene, biguanide salt, thiocarb, cypermethrin, fruit green, cypermethrin, imidacloprid, cresol, kresoxim-methyl, acetaminophen ... Bacillus, clotrimazole, chlorpyrifos, diamine, tetrachloroquinone, tetrachloroquinoxaline, chloropicrin, benzimidazolin, chlorodinitronaphthalene, chlorothalonil, dimethoate, cyanamide, salicylanilide, cyazofamid, diethyl pyrocarbonate, diethofencarb, cyclamates, dichlorocyanamide, sclerotium, benzyltriazole, diflunisal, actinomycin, cycloheximide, chloranil, dichlorophen, dichloronaphthoquinone, disulfiram, dichlorvos, dithiothionol, diniconazole, R-diniconazole, mancozeb, chloranil, o-dimethoate, nitrobenzene, butyl nitrate, chloranil, nitropentyl nitrate, dithiopyridine, diphenylamine, oxadiazole, flutolanil, fluazifop, cyproconazole, cyprodinil, cyprodinil, cyanamide, Sifluazole, dimethomorph, dimethomorph, cymoxanil, etherstrobin, methyl bromide, zinc thiam, silthiopyrad, streptomycin, spiroxamine, pentothyl sulfone, cyproconazole, zoxamide, dazomet, thiadiazine, thiazamide, fluthiazide, thiabendazole, tioxymid, thiochlorfenphim, thiophanate, methyl thiophanate, thiabendazole, chlorpyrifos, thiofuran, thiram, tetrachloronitrobenzene, chlorpyrifos, thiram, fluconazole, imidacloprid, dehydroacetic acid, tebuconazole, isobutyl ethoxyquin, dodecylbenzenesulfonic acid bis(ethylenediamine)copper(II) (DBEDC), dodecylbenzenesulfonic acidCyclomorph, hydrazine, triadimenol, triadimenol, butyltriazole, imidazolin, cypermethrin, myclobutanil, salicylate, tricyclazole, triclopidogrel, trimorpholine, tributyltin oxide, trifloxystrobin, trifloxystrobin, triamcinol, tolylfluanid, methyl tolclofos, domycin, sodium mancozeb, phthalostrobin, nitrostyrene, flubendiamide, copper nonylphenolsulfonate, quinoline acrylate, validamycin, downy mildew, harpin protein, bixafen, picoxystrobin, fluopyram, thiochlorophenol, bifenthrin, soil fungus elimination, soil fungus elimination potassium, binamitraz, biphenyl, disease flower spirit, oxamyl, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, methoxystrobin, pyraclostrobin, Pyrimidine oxime, pyrimidine, pyrimethanil, chlorpyrifos, pyroquilon, vinclozolin, oxadiazon, imidacloprid, imidacloprid, dioxon, chlorpyrifos, seed coat ester, cyanamide, pyrimidine, ferbam, triphenyltin, fenpiclonil, fenpyraclostrobin, fenbendazole, furamide, fenpropimorph, fenhexamid, tetrachlorophthalide, thiosulfan, butylamine, pyrimidine sulfonate, wheat spike, blasticidin, furazolidone, furalaxyl, pyrimidine, fluazinam, fluoxastrobin, triflubenzuron, fluopyram, fluopyram, fluclorac, dimethylfuran, fluoxaclostrobin, fluquinconazole, furconazole, furoconazole, fludioxonil, flusilazole, sulfamethoxazole, fluthiazide , flutolanil, flutriafol, furfural, maogule, fluoxamido, flumorph, quinoline, prochloraz, procymidone, thiocarb, prothioconazole, propamocarb, propiconazole, propineb, furasuron, allylbenzazole, fuconazole, hexachlorobutadiene, hexaconazole, cyclohexyl, pyridazine, bensulfuron, bensulfuron-methyl, malathion, benomyl, blastifungin, quinone oxime hydrazone, penazazole, antibacterial, pencycuron, benzohydroxamic acid, bentaluron, benzothiopyrad, penthiopyrad, pentosuccinate, boscalid, chlorpyrifos, triethyl phosphate, triethyl aluminum, polyoxin, polyoxin, mancozeb, folpet, formaldehyde, engine oil, maneb, mancozeb, dimethoate Propylene glycol, meclocyclamide, myclobutanil, midomycin, mesaccharin, benzocarb, sulfamethoxam, metachlorothiazolin, metamifungin, metamifungin, metalaxyl, metalaxyl-M, metiram, methyl isothiocyanate, mepthyldinocap, metconazole, thiopyrad, mefenamic acid, mefenoxam, mefenamic acid, mefenamic acid, mefenamic acid, mefenamic acid, mefenamic acid, mefenamic acid, iodomethane, pyrimidine, benzalkonium chloride, basic copper chloride, inorganic antimicrobial agents such as basic copper sulfate, silver, sodium hypochlorite, copper hydroxide, wettable sulfur, calcium polysulfide, potassium bicarbonate, sodium bicarbonate, sulfur, anhydrous copper sulfate, nickel thiamethoxam, copper compounds such as quinoline copper, zinc sulfate, copper sulfate pentahydrate, etc.

[0093] Similarly, examples of herbicides include: 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-T butyric acid, 2,4-D, 2,4-D butyric acid, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, 2-methyl-4-chlorophenoxyacetic acid (MCPA), 2-methyl-4-chlorophenoxyacetic acid ethyl ester (MCPA), 2-methyl-4-chlorophenoxyacetic acid thio ... thioethyl), 2-methyl-4-chlorobutyric acid (MCPB), iobenzyl, bennitroprop-butyl, azopyralid, trifluoroacetic acid, azido, tetrazosulfuron, sulfamethoxam, acetochlor, atrazine, atraton, sulfuron, silystrobin, tetrazolin, abscisic acid, amicarbazone, amidosulfuron, cyproconazole, chlorpyrifos, teroxazolidinone, methylaminophosphine, terzinone, ametryn, alachlor, dipropylene glycol, chlorfenapyr, pentachlorovaleric acid, isoxadiazon, chloramphenicol, isoxadiazon, isoxadiazon, isoxadiazon, isoxadiazon, isoxadiazon, isoxadiazon, isoproturon, Isoprolin, isopolinate, butamidosulfuron, anti-indocyanine, anti-indocyanine, halofenazole, prethiopyralid, imazaquin, methyl imazapyr, imazamethapyr, imazamethapyr, imazamox, imazamox, imazamox, azole pyrasulfuron, triazine indole, indolebutyric acid, monogram, glycyrrhizin, dicamba, ethametsulfuron, methyl ethametsulfuron, ethosulfuron, sulfadiazine, indolesulfuron, nitroglycerin, ethephon, ethoxysulfuron, chlorpyrifos, ethametsulfuron, ethosulfuron-butyl, ethoxysulfuron, ethosulfuron-butyl, sulfadiazine, sulfadiazine, chlorpyrifos ... Ketone, propargyl oxazolidinone, cloxacillin, cyprosulfuron, oxadiazon, oxyfluorfen, chlorpyrifos, pyrimidifensulfuron, pyrimidifensulfuron, pyralid, mesotrione, carbazolin, mesotrione, mesotrione ethyl, terachlor, dimethoate, teroxazole, quizalofop-ethyl, quizalofop-ethyl, mesotrione, dimethylbenzene, chloranil, dichloroquinoline, chloroquinoline, benzylpyridinium, iodine chlorpyrifos, glyphosate, glufosinate, glufosinate-P, ethoxysulfuron, clethodim, fruit acid, clodinafop-butyl, clodinafop-butyl, clomeluron, diclopyralid, cyclobutene, fruit acid, chlorbromide, chlorbutane, isoclomazone, Chlorodiol, methoxyfenoxam, chloranil, chlorfenapyr, chloranil ...4-Dichlorprop, dichlorvos, diclofop-butyl, diclofop-butyl, chloranil, diquat, chloranil, disul, cyclohexane, dimethoprim-butyl, dimethomorph, indolesulfuron, pentophenol, sulfamethoxam, dinoseb, terephthalate, dimethomorph, cyanamide, cyhalofop-butyl, cypermethrin, cyhalofop-butyl, cypermethrin, flufenacet, cybutryne, cyproconazole, tricyclic cypermethrin, fluazifop-butyl, dimethomorph, cyproconazole, isopropylamine, cyproconazole, gibberellin, simazine, cyproconazole, dimethoate, isopentanol, dimethomorph, simethomorph, simethomorph, cymaton, piperon, oxazolidinone, cyclohexane Heptaclof, fenpyroxen, azapropazone, sulfotrione, chlorpyrifos, sulfentrazone, sulfosulfuron, sulfosulfuron-methyl ... Gluconol, bensulfuron-methyl, wild wheat chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos-butyl, chlorpyrifos-butyl, chlorpyrifos-butyl, trifloxysulfuron, trifloxysulfuron, indole, bensulfuron-methyl, bensulfuron-methyl, trifloxypropionic acid, trifloxysulfuron oxime, trimethoate, naphthamide, naproxenamide, propamide, nicosulfuron, sulfalin, herbicide ether, trifluoroacetic acid, pyraclostrobin, chlorpyrifos, chlorpyrifos, chlorpyrifos, avena cava, paclobutrazol, paraquat, flurfothiazolin, halofop-methyl, flupyrifos-butyl, flupyrifos-butyl methyl, flunitramide, chlorpyrifos-butyl, chlorpyrifos-butyl, chlorpyrifos-butyl, chlorpyrifos-butyl, chlorpyrifos-butyl Amine, bicyclic pyraclostrobin, bispyribac-sodium, bidanone, pinoxaden, methylcarboxylic acid sulfamethoxazole, oxazolidinone, oxazolidinone, pyrimidine, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, bialamoyl, pyraclostrobin-ethyl, chlorpyrifos, pyridafol, pyrimidine, pyrimidine, pyridafol, pyrimidine, pyrimidine, pyrifos, pyrimidine, pyrifos, pyrifos, pyrifos, pyroxasulfone, methoxysulfone, acetaminophen, pyrimidine ...5-propionic acid, benzoyldiuron, thiazolyl-butyl, chlorophenoxyethanol, tetrazolam, betaine, betaine-ethyl ester, butachlor, fluazifop-butyl, thiamethoxam, butachlor, thiamethoxam-butyl, butachlor, fluazifop-butyl, butachlor, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, propargyl, sulfamethoxam, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, chlorpyrifos, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl , fluazifop-butyl, flupyridazine-butyl, fluazifop-butyl, tetrafluoropropionic acid, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, clofosulphonate, fluazifop-butyl, trifluoxazine, flumethalin, flupyralid, flupyralid, fluazifop-butyl ... Bromobutyric acid amine, furfural nitrile, bispyribac, hexachloroacetone, hexazinone, pethoxamid, benzylchlor, penoxsulam, gram grass antagonist, flubutyric acid amine, bispyribac, yellow grass antagonist, acetaminophen, amino acid killing, benzylchlor, benzylaminopurine, benzylchlor, bispyribac, dithiocarb, benzylsulfuron, new Yanling, benzobicyclon, pyraclostrobin, flusulfuron, bentazone, valerylbenfensulfuron, pendimethalin, pendimethalin, penoxazole, ethylbutyralid, furosulfuron, phosphamidon, fomesulfuron, formosan, formidable amide, bud inhibitor, 2-methyl-4-chloropropionic acid, 2-methyl-4-chloropropionic acid, dioxin, methyl disulfuron, methylsulfuron, mesotrione, methotrexate, methoxypropyl, metazachlor, methomyl, bispyribac, bispyribac Methiocarb, methylbenzimidazole, metamitron, metamifop, metsulfuron, fluazifop, metsulfuron-methyl, metsulfuron-methyl, metsulfuron-methyl, bromothiocarb, pyranocarb, ethersulfuron, isopropyl metolachlor, metribuzin, mefenacet, mefenacet, fluazifop, heptachlor, monisouron, mefenacet, monochloroacetic acid, chlorpyrifos, chlorfenapyr, iodosulfuron, iodosulfuron sodium, iodine nitrile, iodomethane, lactofen, linuron, sulfamethoxam, lenacil, thiocyanate, calcium peroxide, methyl bromide, etc.

[0094] As for the biopesticide, the same effects as above can be expected by mixing the agricultural and horticultural agent of the present invention with, for example, virus preparations obtained from nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), entomopoxvirus (EPV), etc.; microbial insecticides used as insecticides or nematicides, such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans, etc.; microbial insecticides used as fungicides, such as Trichoderma lignorum, Agrobacterium radiobacter, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc. subtilis) and the like; and biopesticides used as herbicides such as Xanthomonas campestris and the like.

[0095] In addition, the agricultural and horticultural agent of the present invention can be used in combination with biological insecticides, including natural enemies such as parasitic wasps (Encarsia formosa), parasitic wasps (Aphidius colemani), gall midges (Aphidoletes aphidimyza), parasitic wasps (Diglyphus isaea), parasitic mites (Dacnusa sibirica), predatory mites (Phytoseiulus persimilis), predatory mites (Amblyseius cucumeris), predatory stink bugs (Orius sauteri), etc.; microbial insecticides such as Beauveria bassiana, (Beauveria brongniartii) and the like; and pheromones such as (Z)-10-tetradecenyl acetate, (E,Z)-4,10-tetradecadienyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-eicosene-10-one, 14-methyl-1-octadecene and the like.

[0096] In a specific embodiment, the insecticidal composition comprises a biologically effective amount of the pyridylalkoxypyrimidine compound or its salt (component A), and at least one other active ingredient (component B) selected from the following compounds: chlorpyrifos, malathion, dinotefuran, imidacloprid, thiamethoxam, trifluanid, sulfoxaflor, nitenpyram, pymetrozine, cypermethrin, buprofezin, oxazolidinone or oxazolidinone.

[0097] In another specific embodiment, the weight ratio of the active ingredients A and B in the insecticidal composition is 1:100-100:1, 1:80-80:1, 1:50-50:1, 1:20-20:1, 1:10-10:1, 1:5-1:1 or 1:1-5:1.

[0098] The term "biologically effective amount" refers to an amount of a biologically active compound (e.g., a compound of Formula I or a salt thereof) sufficient to produce the desired biological effect when applied to (i.e., contacted with) the pest to be controlled or its environment, or the plant, the seed from which the plant grows, or the locus of the plant (e.g., the growth medium), thereby protecting the plant from damage by the pest or achieving other desired effects (e.g., increasing plant vigor). The compounds of the present invention can also be applied prophylactically to locations where pests or parasites are expected to appear. DETAILED DESCRIPTION

[0099] The following examples are provided to illustrate the present invention and should not be considered to limit the present invention in any way. The scope of the rights claimed in the present invention is described in the claims.

[0100] Given the economical efficiency and diversity of the compounds, we have selected and synthesized a number of compounds. A selection of these compounds is listed in Table 1 below. The specific compound structures and corresponding compound information are shown in Table 1. The compounds in Table 1 are intended to better illustrate the present invention but are not intended to limit the present invention. Those skilled in the art should not interpret this as limiting the scope of the present invention to the following compounds.

[0101] Table 1 Compound structures and their 1 H NMR

[0102] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The starting materials can be purchased commercially or can be prepared by methods known in the literature or as described in detail. It will be understood by those skilled in the art that other synthetic routes can also be used to synthesize the compounds of the present invention. Although the specific starting materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar starting materials and conditions, and these modifications or variations of the preparation methods of the present invention that result in various isomerizations of the compounds are included within the scope of the present invention. In addition, the preparation methods described below can be further modified according to the present disclosure using conventional chemical methods well known to those skilled in the art. For example, appropriate groups can be protected during the reaction, etc.

[0103] The following process examples are provided to facilitate a further understanding of the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further illustrate the present invention and are not intended to limit its reasonable scope. The reagents used in the synthesis of the compounds shown in the table below are either commercially available or can be readily prepared by one of ordinary skill in the art.

[0104] Examples of representative compounds are shown below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0105] 1. Synthesis of Compound 24

[0106] 4,6-Dichloro-5-pyrimidinecarboxaldehyde (0.4 g, 2.26 mmol, 1 eq), triethyl orthoformate (0.5 g, 3.39 mmol, 1.5 eq), and p-toluenesulfonic acid (39 mg, 0.226 mmol, 0.1 eq) were dissolved in 15 ml of ethanol and stirred at room temperature for 2 h. The product was monitored as the main peak. After completion of the reaction, the ethanol solvent was rotary evaporated, and the mixture was extracted with water and ethyl acetate. The organic phase was washed twice with saturated brine and dried over anhydrous sodium sulfate. The mixture was mixed and subjected to normal phase separation (EA / PE = 1 / 10) to obtain 0.24 g of 24-1, with a yield of 42.3%.

[0107] The above-obtained 24-1 (0.24 g, 0.956 mmol, 1 eq) and 5-trifluoromethylpyridine-2-methanol (0.169 g, 0.956 mmol, 1 eq) were dissolved in DMF (10 ml) and added to a 50 ml single-necked flask. Sodium hydride (27.5 mg, 1.15 mmol, 1.2 eq) was added under an ice bath and allowed to react for 2 h. After monitoring the reaction for completion, water and ethyl acetate were added for extraction and separation. The organic phase was washed twice with saturated brine and dried over anhydrous sodium sulfate. The mixture was mixed and subjected to normal phase separation (EA / PE = 1 / 7) to afford 24-2 (230 mg, yield: 61.4%).

[0108] 24-2 (230 mg, 0.587 mmol, 1 eq), formic acid (53 mg, 0.881 mmol, 1.5 eq), and triethylamine (95 mg, 0.939 mmol, 1.6 eq) were dissolved in DMF and added to a 50 ml single-necked flask. Tetrakis(triphenylphosphine)palladium (68 mg, 0.059 mmol, 0.1 eq) was added under a nitrogen atmosphere, and the mixture was allowed to react at 80°C under nitrogen for 12 h. After monitoring the reaction completion, water and ethyl acetate were added for extraction. The organic phase was washed twice with saturated brine and dried over anhydrous sodium sulfate. The sample was mixed and subjected to normal phase separation (EA / PE = 1 / 8) to afford 150 mg of compound 24 in a yield of 71.5%.

[0109] 2. Synthesis of Compound 26

[0110] 26-1 (218 mg, 1.06 mmol, 1 eq) was dissolved in 5 ml of DMF, and 5-trifluoromethylpyridine-2-methanol (206.2 mg, 1.166 mmol, 1.1 eq) was added. 60% pure sodium hydride (50.78 mg, 1.272 mmol, 1.2 eq) was added under ice-cooling conditions, and the mixture was stirred at room temperature for 2 h. After monitoring the reaction for completion, water was added to quench the sodium hydride, and the mixture was extracted with water and ethyl acetate. The organic phase was washed twice with saturated brine and dried over anhydrous sodium sulfate. The mixture was mixed and subjected to normal phase separation (EA / PE = 1 / 3) to obtain 26-2 (179 mg, yield: 49%).

[0111] 26-2 (179 mg, 0.52 mmol, 1 eq) was dissolved in 8 ml of DMA, and triethylamine (83.59 mg, 0.83 mmol, 1.6 eq) and formic acid (35.64 mg, 0.78 mmol, 1.5 eq) were added. Finally, tetrakistriphenylphosphine palladium (59.66 mg, 0.05 mmol, 0.1 eq) was added. The nitrogen atmosphere was evacuated three times and the reaction was carried out at 80°C for 12 h. The product was monitored as the main peak, with a small amount of starting material remaining. The tetrakistriphenylphosphine palladium was filtered through celite, and the mixture was extracted with water and ethyl acetate. The organic phase was washed twice with saturated brine and dried over anhydrous sodium sulfate. The sample was mixed and subjected to normal phase separation (EA / PE = 1 / 3) to obtain 26 (31 mg, yield: 19.2%).

[0112] 3. Synthesis of Compound 27

[0113] 4-Chloro-5-iodopyrimidine (200 mg, 0.83 mmol, 1 eq) and 5-trifluoromethylpyridine-2-methanol (147 mg, 0.83 mmol, 1 eq) were dissolved in 5 mL of DMF, cooled to 0°C, and 60% sodium hydride (40 mg, 0.99 mmol, 1.2 eq) was added. The system was allowed to return to room temperature naturally and stirred for 2 h. After monitoring the completion of the reaction, the reaction was quenched with water and extracted with ethyl acetate. The organic phase was washed twice with saturated brine and dried over anhydrous sodium sulfate. The sample was mixed and subjected to normal phase separation (EA / PE = 1 / 10) to obtain 190 mg of 27-1 in a yield of 59.9%.

[0114] 27-1 (300 mg, 0.78 mmol, 1 eq) was dissolved in 10 ml of toluene and added to a 50 ml single-necked flask. 1 ml of water was then added, along with cyclopropylboronic acid (101 mg, 1.18 mmol, 1.5 eq), potassium phosphate (584 mg, 2.75 mmol, 3.5 eq), palladium acetate (17 mg, 0.078 mmol, 0.1 eq), and tricyclohexylphosphine (22 mg, 0.078 mmol, 0.1 eq). Under N2 protection, the reaction was heated to 80°C and allowed to react for 12 h. The remaining starting material was monitored for the presence of a product peak. Silica gel was then added to the sample, and the mixture was separated by normal phase separation (EA / PE = 1 / 1) to afford 40 mg of 27, a 17.2% yield.

[0115] 4. Synthesis of Compound 2

[0116] Compound 2-1 (2.3 g, 12.03 mmol) was dissolved in DMF (25 mL), and compound 2-2 (3.22 g, 14.44 mmol) was added. The temperature was lowered to 0°C, and 60% sodium hydride (0.72 g, 18.05 mmol) was slowly added. The reaction was allowed to react at room temperature for 1 h, and the disappearance of the starting material was monitored. The reaction solution was quenched with water, extracted three times with ethyl acetate, and washed three times with saturated brine. After concentration and column purification (PE / EA = 5 / 1), compound 2-3 (3.6 g, 79% yield) was obtained as a white solid.

[0117] Compound 2-3 (3.6 g, 9.53 mmol) was dissolved in DMF (40 mL), and triethylamine (1.54 g, 15.25 mmol) and formic acid (0.66 g, 14.30 mmol) were slowly added. After nitrogen displacement, a catalytic amount of 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloromethane complex was added. The temperature was slowly raised to 80°C and the reaction was allowed to react for 12 hours, monitoring the disappearance of the starting materials. The reaction mixture was added with water and extracted three times with ethyl acetate, and then washed three times with saturated brine. After drying and concentration, the product was purified by column chromatography, and the fraction was spin-dried to obtain compound 2 (2.2 g, 67% yield) as a white solid.

[0118] 5. Synthesis of Compound 38

[0119] Compound 2 (2.2 g, 6.41 mmol) was dissolved in 25 ml of HCl / EA solution and reacted at room temperature for 24 h. The product signal was detected. The reaction solution was concentrated and purified by column chromatography (PE / EA = 3 / 1) to obtain compound 38-1 (1.6 g, yield 84%) as a white solid.

[0120] Compound 38-1 (1.6 g, 5.38 mmol) was dissolved in 20 ml of tetrahydrofuran and added to a 100 ml three-necked flask. The atmosphere was replaced with nitrogen three times, and the mixture was cooled to 0°C in an ice bath. Methylmagnesium bromide (3.59 ml, 10.77 mmol, 3 M in THF) was slowly added dropwise. The mixture was reacted at room temperature for 6 h. The disappearance of the reaction starting material was monitored, the reaction solution was quenched, concentrated, purified by normal phase, and the fraction was spin-dried to obtain compound 38-2 (0.9 g, 53% yield) as a white solid.

[0121] Compound 38-2 (0.9 g, 2.87 mmol) was dissolved in DMF (15 mL), cooled to 0°C, and 60% sodium hydride (0.17 g, 4.31 mmol) was added. The reaction was allowed to react at room temperature for 15 minutes. Iodomethane (0.49 g, 3.45 mmol) was then added and allowed to react at room temperature for 3 hours, monitoring the disappearance of the starting material. The reaction solution was quenched with water, extracted three times with ethyl acetate, and washed three times with saturated brine. After drying over anhydrous sodium sulfate, the sample was mixed and purified by column chromatography (PE / EA = 6 / 1) to obtain compound 38 (0.52 g, 55% yield) as a white solid.

[0122] 6. Synthesis of Compound 39

[0123] Compound 39-1 (200 mg, 1.14 mmol), dimethyl disulfide (127 mg, 2.00 mmol), and trimethylsilyl chloride (371 mg, 3.40 mmol) were dissolved in 10 ml of acetonitrile. Indium (131 mg, 1.14 mmol) was added and stirred overnight at room temperature under a nitrogen atmosphere. LCMS monitored the reaction for completion. The reaction solution was concentrated and diluted with ethyl acetate. The organic phase was washed with water and saturated brine, dried, and concentrated. The residue was purified by column chromatography (EA / PE = 1 / 5) to afford compound 39-2 (0.2 g, 69.3%).

[0124] Compound 39-3 (139 mg, 0.78 mmol) was dissolved in 5 ml of DMF. Sodium hydroxide (31 mg, 0.78 mmol) was added under ice-cooling conditions and allowed to react for 15 minutes. Compound 39-2 (200 mg, 0.78 mmol) was then added and allowed to react for 1 hour. The reaction was quenched with water and diluted with ethyl acetate. The organic phase was washed with water and saturated brine, dried, and concentrated. The residue was purified by column chromatography (EA / PE = 2 / 5) to afford compound 39-4 (0.2 g, 64.5%).

[0125] Compound 39-4 (200 mg, 0.50 mmol), formic acid (45 mg, 0.75 mmol), triethylamine (81 mg, 0.80 mmol), and a catalytic amount of tetrakistriphenylphosphine palladium were dissolved in 10 ml of DMF and stirred at 80°C under a nitrogen atmosphere for 12 hours. The reaction solution was concentrated and diluted with ethyl acetate. The organic phase was washed with water and saturated brine, dried, and concentrated. The residue was purified by column chromatography (EA / PE = 1 / 4) to give 39 (69 mg, 36%).

[0126] 7. Synthesis of Compound 45

[0127] Compound 45-1 (250 mg, 1.31 mmol) was dissolved in 5 ml of DMF. Sodium hydroxide (52 mg, 1.31 mmol) was added under ice-cooling conditions and allowed to react for 15 minutes. Compound 45-2 (314 mg, 1.31 mmol) was then added and allowed to react for 1 hour. The reaction was quenched with water and diluted with ethyl acetate. The organic phase was washed with water and saturated brine, dried, and concentrated. The residue was purified by column chromatography (EA / PE = 2 / 5) to afford compound 45-3 (0.32 g, 61.9%).

[0128] Compound 45-3 (320 mg, 0.81 mmol) was dissolved in 5 ml of toluene and 1 ml of water. Cyclopropylboronic acid (139 mg, 1.62 mmol) and potassium phosphate (343 mg, 1.62 mmol) were added, along with catalytic amounts of tricyclohexylphosphine and palladium acetate. The mixture was stirred at 100°C under a nitrogen atmosphere for 12 hours. The reaction mixture was concentrated and diluted with ethyl acetate. The organic phase was washed with water and saturated brine, dried, and concentrated. The residue was purified by column chromatography to yield compound 45 (80 mg, 31.9%).

[0129] Biological activity evaluation:

[0130] (1) Insecticidal activity test:

[0131] After the original drug is dissolved in acetone, the solution is diluted with distilled water to a gradient dose. 3rd-instar test insects (brown planthoppers / white-backed planthoppers) with the same physiological state raised indoors are selected and placed in cups, with 40 test insects in each cup. Select Huaidao No. 5 rice with a stem thickness of more than 3mm, cut it from the base of the stem, and then insert it into a 2.5×2.5×2.5cm cross-shaped seedling sponge. Then put the rice and the seedling sponge into the cup and spray it using a spray tower. After the spraying is completed, cover the cup mouth with a cup and repeat 3 times. The highest dose of acetone is used as a control. After application, transfer it to the insecticide treatment room for breeding. The results were investigated after 4-7 days, and the mortality of each treatment was counted separately. The mortality rate was calculated according to the formula: mortality rate (%) = (number of dead insects / number of test insects) * 100. Representative data are shown in Table 2.

[0132] Table 2 Insecticidal activity test results

[0133] Note: N stands for no data; Reference compound A: Control compound B:

[0134] (2) Conductivity test:

[0135] Healthy rice plants were selected and planted in small black bowls. The rice was drought-treated for 24 hours in advance, with 2-3 rice plants per bowl. 20 mL of the prepared solution was then poured through the rice roots. Two bowls of rice were treated, with 20 mL poured into each bowl. A water control was provided, and the plants were kept under normal light conditions to ensure normal root growth. After two days of treatment, the plants were cut at the base of the stem and inserted into a 2.5 × 2.5 × 2.5 cm cross-shaped seedling sponge. The rice and sponge were then placed in a cup, and 40 test insects were inoculated into each cup. Results were collected after 4-7 days, and mortality was counted for each treatment. The mortality rate was calculated using the formula: mortality (%) = (number of dead insects / number of test insects) * 100. Representative results are shown in Table 3.

[0136] Table 3 Conductivity test results

[0137] Note: Control compound C:

[0138] (3) Composition insecticide activity determination test:

[0139] 3.1) Test conditions and operating steps

[0140] Referring to the above insecticidal activity test, the test target is brown planthopper.

[0141] 3.2) Qualitative evaluation of efficiency

[0142] Toxicity tests were performed at different ratios within the selected range, and the optimal ratio was selected based on the synergistic effect. A synergistic effect > 0 indicates a synergistic effect; a synergistic effect close to 0 indicates an additive effect; and a synergistic effect < 0 indicates an antagonistic effect.

[0143] Synergistic effect = actual mortality rate - theoretical mortality rate

[0144] Theoretical mortality rate = 1-(1-P1)(1-P2)

[0145] Where, P1, P2 are the mortality rates of each single dose in the mixture.

[0146] Table 4 Qualitative evaluation test results of the composition synergistic effect

[0147] The pyridylalkoxypyrimidine compound or its salt of the present invention has excellent effects as an agricultural and horticultural insecticide. In addition, the compound or its salt shows effects on pests that parasitize pet animals (such as dogs and cats) and domestic animals (such as cattle and sheep).

Claims

1. A pyridylalkoxypyrimidine compound or a salt thereof, as shown in Formula I: in, X and Y each independently represent hydrogen, hydroxy, alkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, cycloalkylalkyloxy, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, cycloalkylalkylthio, or represents -CH=CH-R, -CH=NOR or cycloalkyl; Z represents hydrogen, halogen, cyano, amino, nitro, formyl, cyanoalkyl, hydroxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkylthio, alkylamino, haloalkoxy, haloalkylthio, alkylcarbonyl, alkoxycarbonyl, alkoxyalkyl, haloalkoxyalkyl, alkylaminoalkyl, aryl, heterocyclyl, arylalkyl or heterocyclylalkyl, wherein the alkyl, alkenyl or alkynyl is optionally substituted with halogen, and the cycloalkyl, cycloalkenyl, heterocyclyl or aryl is optionally substituted with at least one group selected from alkyl, haloalkyl, alkylsulfonyl, alkylacyl, alkylacyloxy, alkoxyacyl, halogen, alkoxy, alkylthio, cyano, amino or alkylamino; R each independently represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl or arylalkyl; wherein the cycloalkyl, cycloalkenyl, heterocyclyl or aryl is optionally substituted by at least one group selected from alkyl, haloalkyl, alkylsulfonyl, alkylacyl, alkylacyloxy, alkoxyacyl, halogen, alkoxy, alkylthio, cyano, amino or alkylamino.

2. The pyridylalkoxypyrimidine compound or its salt according to claim 1, characterized in that: X and Y each independently represent hydrogen, hydroxy, C1-C8 alkyl, C1-C8 alkoxy, C2-C8 alkenyloxy, C2-C8 alkynyloxy, C3-C8 cycloalkyloxy, C3-C8 cycloalkylC1-C8 alkyloxy, C1-C8 alkylthio, C2-C8 alkenylthio, C2-C8 alkynylthio, C3-C8 cycloalkylthio, C3-C8 cycloalkylC1-C8 alkylthio, or represents -CH=CH-R, -CH=NOR or C3-C8 cycloalkyl; Z represents hydrogen, halogen, cyano, amino, nitro, formyl, cyano C1-C8 alkyl, hydroxy C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, halogenated C1-C8 alkoxy, halogenated C1-C8 alkylthio, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy C1-C8 alkyl, halogenated C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylamino C1-C8 Alkyl, aryl, heterocyclic group, aryl C1-C8 alkyl or heterocyclic C1-C8 alkyl, wherein the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally substituted with halogen, and the C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclic group or aryl is optionally substituted with at least one group selected from C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkylsulfonyl, C1-C8 alkylacyl, C1-C8 alkylacyloxy, C1-C8 alkoxyacyl, halogen, C1-C8 alkoxy, C1-C8 alkylthio, cyano, amino or C1-C8 alkylamino; R each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl or arylC1-C8 alkyl; In the above, the C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl or aryl is optionally substituted by at least one group selected from C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkylsulfonyl, C1-C8 alkylacyl, C1-C8 alkylacyloxy, C1-C8 alkoxyacyl, halogen, C1-C8 alkoxy, C1-C8 alkylthio, cyano, amino or C1-C8 alkylamino.

3. The pyridylalkoxypyrimidine compound or a salt thereof according to claim 1 or 2, characterized in that: X and Y each independently represent hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkyloxy, C3-C6 cycloalkylC1-C6 alkyloxy, C1-C6 alkylthio, C2-C6 alkenylthio, C2-C6 alkynylthio, C3-C6 cycloalkylthio, C3-C6 cycloalkylC1-C6 alkylthio, or represents -CH=CH-R, -CH=NOR or C3-C6 cycloalkyl; Z represents hydrogen, halogen, cyano, amino, nitro, formyl, cyano C1-C6 alkyl, hydroxy C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, halogenated C1-C6 alkoxy, halogenated C1-C6 alkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy C1-C6 alkyl, halogenated C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylamino C1-C6 Alkyl, aryl, heterocyclic group, aryl C1-C6 alkyl or heterocyclic C1-C6 alkyl, wherein the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally substituted with halogen, and the C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic group or aryl is optionally substituted with at least one group selected from C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkylsulfonyl, C1-C6 alkylacyl, C1-C6 alkylacyloxy, C1-C6 alkoxyacyl, halogen, C1-C6 alkoxy, C1-C6 alkylthio, cyano, amino or C1-C6 alkylamino; R each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl or arylC1-C6 alkyl; wherein the C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl or aryl is optionally substituted by at least one group selected from C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkylsulfonyl, C1-C6 alkylacyl, C1-C6 alkylacyloxy, C1-C6 alkoxyacyl, halogen, C1-C6 alkoxy, C1-C6 alkylthio, cyano, amino or C1-C6 alkylamino; Preferably, the compound is selected from any one of Table 1 in the specification.

4. The method for preparing a pyridylalkoxypyrimidine compound or a salt thereof according to any one of claims 1 to 3, comprising the following steps: (1) Compound II is subjected to hydrogenation reaction to obtain compound I, and the chemical reaction equation is as follows: Alternatively, (2) Compound III and Compound IV are subjected to a substitution reaction to obtain Compound I, and the chemical reaction equation is as follows: Alternatively, (3) Compound V and Compound IV are first subjected to a substitution reaction to obtain Compound VI, and Compound VI is then reacted with VII to obtain Compound I. The chemical reaction equation is as follows: in, Hal each independently represents a halogen, and the substituents X, Y and Z are defined as described in any one of claims 1 to 3.

5. The method for preparing a pyridylalkoxypyrimidine compound or a salt thereof according to claim 4, characterized in that: The step (1) is carried out in the presence of formic acid or hydrogen, a base, a catalyst and a solvent; or the first step in the step (2) and the step (3) is carried out in the presence of a base and a solvent; or the second step in the step (3) is carried out in the presence of a catalyst, a base and a solvent; preferably, the catalyst in the second step in the step (1) and the step (3) is Pd(dppf)Cl2·CH2Cl2, Pd(dppf)Cl2, Pd(PPh3)4, PdCl2, Pd(OAc)2, tricyclohexylphosphine palladium acetate, Pd(PPh3)2Cl2 or NiCl2(dppf); the solvent in the steps (1), (2) and (3) is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, toluene, water, dichloromethane or ethyl acetate; and the base in the steps (1), (2) and (3) is selected from at least one of an inorganic base or an organic base.

6. An insecticidal composition, characterized in that: The invention comprises a biologically effective amount of at least one of the pyridylalkoxypyrimidine compounds or salts thereof according to any one of claims 1 to 3; preferably, it also comprises a formulation adjuvant; more preferably, it also comprises other active ingredients.

7. The insecticidal composition according to claim 6, characterized in that The other active ingredients are selected from at least one of the following compounds: chlorpyrifos, malathion, dinotefuran, imidacloprid, thiamethoxam, trifluanid, sulfoxaflor, nitenpyram, pymetrozine, cypermethrin, buprofezin, oxathiapiprolin or oxathiasulfuron; preferably, the weight ratio of the pyridylalkoxypyrimidine compound or its salt to the other active ingredients in the insecticidal composition is 1:100-100:1, 1:80-80:1, 1:50-50:1, 1:20-20:1, 1:10-10:1, 1:5-1:1 or 1:1-5:

1.

8. A method for controlling pests, characterized in that: The method comprises contacting the pest or its environment with a biologically effective amount of the pyridylalkoxypyrimidine compound or a salt thereof according to any one of claims 1 to 3 or the composition according to claim 6 or 7.

9. Use of the pyridylalkoxypyrimidine compound or its salt according to any one of claims 1 to 3 or the composition according to claim 6 or 7 in controlling pests.

Images