US 2013/0296271 A1 · Agri-Horticultural Pest Control Compositions Comprising 4-(3-Butynyl)Aminopyrimidine Derivatives

Abstract

Agri-horticultural pest control compositions having outstanding control effect on pests, in particular, agri-horticultural pests, which comprise as active ingredients one or more 4-(3-butynyl)aminopyrimidine derivatives represented by the general formula [I], namely, where R1 is typically selected from among: a) phenyl c) —SiR5R6R7 (R5, R6, and R7 which may be the same or different represent a linear or branched alkyl having 1-6 carbon atoms, a linear or branched haloalkyl having 1-3 carbon atoms which is substituted by one halogen atom, a linear or branched cyanoalkyl having 1-3 carbon atoms which is substituted by one cyano group, and phenyl); d) hydropgen atom; R2 typically represents a hydrogen atom; R3 typically represents a hydrogen atom; R4 represents a hydrogen atom and one or more agri-horticultural pest control compounds selected from among agri-horticultural antimicrobial compounds, say, multi-site contact active compouns, nucleic acids synthesis inhibitory active compounds, mitosis and cell divesion inhibitory active compounds, and/or agri-horticultural insecticidal, miticidal or nematicidal compounds, say, acetylcholinesterase inhibitors, GABA-gated chloride antagonists, and sodium channel modulators. Since the 4-(3-butynyl)aminopyrimidine derivatives and the existing antimicrobial active compounds and/or insecticidal active compounds are used in admixture, the 4-(3-butynyl)aminopyrimidine derivatives which are useful as pest control agents, particularly as agri-horticultural pest control agents, need be used in smaller amounts and yet their antimicrobial or insecticidal activity can be improved.

An agri-horticultural pest control composition which comprises as active ingredients one or more 4-(3-butynyl)aminopyrimidine derivatives represented by the general formula [I] and one or more agri-horticultural antimicrobial compounds or agri-horticultural insecticidal compounds selected from among the following (1) to (39):

where R1 is selected from among:
a) a monocyclic or bicyclic ring optionally containing 0-3 hetero atoms, as selected from the group consisting of phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzisothiazolyl, pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzisooxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, and pyridonyl;
b) a linear or branched alkyl having 1-6 carbon atoms, a linear or branched alkenyl having 2-8 carbon atoms, a linear or branched alkynyl having 2-8 carbon atoms, a cycloalkyl having 3-8 carbon atoms, or a cycloalkenyl having 3-8 carbon atoms;
c) —SiR5R6R7 (where R5, R6 and R7 are a linear or branched alkyl having 1-6 carbon atoms, a linear or branched haloalkyl having 1-3 carbon atoms which is substituted by one halogen atom, a linear or branched cyanoalkyl having 1-3 carbon atoms which is substituted by one cyano group, and phenyl, provided that two or all of these may be the same substituent or all may be different substituents);
d) a hydrogen atom;
in the case of a) or b), R1 may be substituted by —C(O)OR, —C(O)R, —R, —OR, —SR, —SO2R, —OC(O)R, —C(O)NHR, —C(O)NR2, —NHSO2R, —NRSO2R, —NHR, —NR2, —NHC(O)R, —NRC(O)R, —NHC(O)OR, —NRC(O)OR, —N(OR)C(O)OR, —NHSO2R, —NRSO2R, —SO2NHR, —SO2NR2 (where R is a linear or branched alkyl having 1-8 carbon atoms, a linear or branched alkenyl having 2-8 carbon atoms, a linear or branched alkynyl having 2-8 carbon atoms, or a cycloalkyl having 3-8 carbon atoms), —SiR5R6R7, —OSiR5R6R7 (where R5, R6 and R7 are a linear or branched alkyl having 1-6 carbon atoms, a linear or branched haloalkyl having 1-3 carbon atoms which is substituted by one halogen atom, a linear or branched cyanoalkyl having 1-3 carbon atoms which is substituted by one cyano group, and phenyl, provided that two or all of these may be the same substituent or all may be different substituents), haloalkyl (a linear or branched alkyl group having 1-4 carbon atoms which is substituted by 1-9 halogen atoms which may be the same or different), haloalkenyl (a linear or branched alkenyl group having 2-6 carbon atoms which is substituted by 1-4 halogen atoms which may be the same or different), haloalkoxy (a linear or branched alkoxy group having 1-4 carbon atoms which is substituted by 1-9 halogen atoms which may be the same or different), acylalkoxy (a linear or branched alkoxy group having 1-3 carbon atoms which is substituted by one or two acyl groups represented by (a linear or branched aliphatic hydrocarbon group having 1-8 carbon atoms)-CO—), acyloxyalkyl (a linear or branched alkyl group having 1-3 carbon atoms which is substituted by one or two acyloxy groups represented by (a linear or branched aliphatic hydrocarbon group having 1-8 carbon atoms)-CO—O—), alkylsulfonylalkyl (a linear or branched alkyl group having 1-3 carbon atoms which is substituted by one or two linear or branched alkylsulfonyl groups having 1-8 carbon atoms), siloxyalkyl (a linear or branched alkyl group having 1-3 carbon atoms which is substituted by one or two —OSiR5R6R7 (where R5, R6 and R7 are a linear or branched alkyl having 1-6 carbon atoms, a linear or branched haloalkyl having 1-3 carbon atoms which is substituted by one halogen atom, a linear or branched cyanoalkyl having 1-3 carbon atoms which is substituted by one cyano group, and phenyl, provided that two or all of these may be the same substituent or all may be different substituents)), hydroxyalkyl (a linear or branched alkyl group having 1-3 carbon atoms which is substituted by one or two hydroxyl groups), alkoxyalkyl (a linear or branched alkyl group having 1-3 carbon atoms which is substituted by one or two linear or branched alkoxy groups having 1-8 carbon atoms), haloalkoxyalkyl (a linear or branched alkyl group having 1-3 carbon atoms which is substituted by one or two linear or branched haloalkoxy groups having 1-4 carbon atoms which are substituted by 1-9 halogen atoms which may be the same or different), alkylthioalkyl (a linear or branched alkyl group having 1-3 carbon atoms which is substituted by one or two linear or branched alkylthio groups having 1-8 carbon atoms), dialkoxyacetal (a dialkoxymethyl group having two linear or branched alkoxy groups with 1-8 carbon atoms substituted on the methyl group), alkoxyalkoxy (a linear or branched alkoxy group having 1-3 carbon atoms which is substituted by one or two linear or branched alkoxy groups having 1-8 carbon atoms), cyanoalkyl (a linear or branched alkyl group having 1-3 carbon atoms which is substituted by one or two cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzodioxolyl, imide, formyl (—CHO), carboxyl (—COOH), formamide (—NHCHO), cyclic ether, and cyclic amine;
R2 represents a hydrogen atom, —R, —OR, —C(O)OR, —C(O)NHR, —CONR2 (where R is a linear or branched alkyl having 1-8 carbon atoms, a linear or branched alkenyl having 2-8 carbon atoms, a linear or branched alkynyl having 2-8 carbon atoms, or a cycloalkyl having 3-8 carbon atoms), hydroxyalkyl (a linear or branched alkyl group having 1-3 carbon atoms which is substituted by 1 or 2 hydroxyl groups), alkoxyalkyl (a linear or branched alkyl group having 1-3 carbon atoms which is substituted by 1 or 2 alkoxy groups having 1-8 carbon atoms), haloalkoxyalkyl (a linear or branched alkyl groups having 1-3 carbon atoms which is substituted by 1 or 2 linear or branched haloalkoxy groups having 1-4 carbon atoms which are substituted by 1-9 halogen atoms which may be the same or different), phenyl, heteroaryl, halogen, cyano, haloalkyl (a linear or branched alkyl group having 1-4 carbon atoms which is substituted by 1-9 halogen atoms which may be the same or different), or haloalkoxy (a linear or branched alkoxy group having 1-4 carbon atoms which is substituted by 1-9 halogen atoms which may be the same or different);
R3 represents (1) a hydrogen atom, (2) a halogen atom, (3) an alkyl having 1-6 carbon atoms which is substituted by 1 to 4 acyloxys represented by (a linear or branched aliphatic hydrocarbon group having 1-8 carbon atoms)-CO—O—, 1-13 halogen atoms, or 1-4 hydroxyl groups, (4) an unsubstituted alkyl having 1-6 carbon atoms, (5) —OR, —SR, or —SO2R (where R is a linear or branched alkyl having 1-8 carbon atoms, a linear or branched alkenyl having 2-8 carbon atoms, a linear or branched alkynyl having 2-8 carbon atoms, or a cycloalkyl having 3-8 carbon atoms), or (6) a haloalkyl (a linear or branched alkyl group having 1-4 carbon atoms which is substituted by 1-9 halogen atoms which may be the same or different);
R4 represents a hydrogen atom, a halogen atom, an alkyl having 1-6 carbon atoms, a nitro, an amino, a phenyl, a benzyl or, taken together with R3 and two carbon atoms of the pyrimidine ring, may form a thiophene ring, a pyridine ring, a pyrrole ring, an imidazole ring, a benzene ring, a naphthalene ring, a pyrimidine ring, a furan ring, a pyrazine ring, a pyrazole ring, or an oxazole ring;
(1) multi-site contact active compounds:
chlorothalonil, dithianon, captan, folpet, iminoctadine albesilate, iminoctadine triacetate, ferbam, nabam, maneb, mancozeb, metiram, propineb, polycarbamate, thiram, ziram, zineb, cupric oxide, copper hydroxide, copper oxychloride, copper sulfate (anhydride), copper sulfate, and sulphur;
(2) nucleic acids synthesis inhibitory active compounds:
metalaxyl, metalaxyl-M, oxadixyl, bupirimate, hymexazol, and oxolinic acid;
(3) mitosis and cell division inhibitory active compounds:
benomyl, carbendazim, diethofencarb, thiophanate-methyl, zoxamide, pencycuron, and fluopicolide;
(4) succinate dehydrogenase inhibitory active compounds:
furametpyr, penthiopyrad, thifluzamide, boscalid, oxycarboxin, carboxin, fluopyram, flutolanil, mepronil, sedaxane, isopyrazam, penflufen, bixafen, and fluxapyroxad;
(5) strobilurin compounds:
azoxystrobin, picoxystrobin, kresoxim-methyl, trifloxystrobin, orysastrobin, metominostrobin, pyraclostrobin, famoxadone, fenamidone, pyribencarb, dimoxystrobin, pyrametostrobin, and pyraoxystrobin;
(6) other electron transport chain inhibitory active compounds:
diflumetorim, cyazofamid, amisulbrom, meptyl dinocap, fluazinam, and ferimzone;
(7) amino acids and protein synthesis inhibitory active compounds:
cyprodinil, mepanipyrim, pyrimethanil, blasticidin-S, streptomycin, and kasugamycin;
(8) sterol biosynthesis inhibitory active compounds:
azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, epoxiconazole, fenbuconazole, furconazole, hexaconazole, imibenconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole, tebuconazole, triadimefon, triadimenol, triticonazole, imazalil, triflumizole, pefurazoate, prochloraz, fenarimol, fenhexamid, fenpropimorph, piperalin, and spiroxamine;
(9) signal transduction inhibitory active compounds:
iprodione, myclozolin, procymidone, vinclozolin, quinoxyfen, fludioxonil, and proquinazid;
(10) lipid biosynthesis inhibitory active compounds:
iprobenfos, isoprothiolane, quintozene, propamocarb, and prothiocarb;
(11) cell wall biosynthesis inhibitory active compounds:
validamycin, polyoxin B, dimethomorph, iprovalicarb, benthiavalicarb, mandipropamid, flumorph, and valifenalate;
(12) melanine synthesis inhibitory active compounds:
pyroquilon, tricyclazole, carpropamid, diclocymet, and fenoxanil;
(13) host plant defence inducing compounds:
acibenzolar-5-methyl, probenazole, isotianil, and laminarin;
(14) compounds having unknown mode of actions:
cymoxanil, fosetyl-Al, triazoxide, methasulfocarb, flusulfamide, chinomethionat, ethaboxam, cyflufenamid, flutianil, metrafenone, tebufloquin, pyridylamidine, enestroburin, fluopyram, and pyriofenone;
(15) biocides:
Agrobacterium radiobacter, Bacillus subtilis, Erwinia carotovora, Pseudomonas fluorescens, Talaromyces flavus, and Trichoderma atroviride;
(16) acetylcholinesterase inhibitors (Carbamates):
aldicarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenobucarb, methiocarb, methomyl, oxamyl, and thiodicarb;
(17) acetylcholinesterase inhibitors (Organophosphates):
acephate, chlorpyrifos, diazinon, dimethoate, malathion, methamidophos, monocrotophos, parathion-methyl, profenofos, terbufos, and imicyafos;
(18) GABA-gated chloride antagonists:
endosulfan, ethiprole, fipronil, and acetoprole;
(19) sodium channel modulators:
bifenthrin, cypermethrin, esfenvalerate, etofenprox, lambda-cyhalothrin, tefluthrin, DDT, and methoxychlor;
(20) nicotinic acetylcholine receptor agonists:
acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam;
(21) nicotinic acetylcholine receptor allosteric activators:
spinetoram, and spinosad;
(22) chloride channel activators:
abamectin, emamectin benzoate, milbemectin, and lepimectin;
(23) juvenile hormone mimics:
kinoprene, methoprene, fenoxycarb, and pyriproxyfen;
(24) multi-site inhibitors:
methyl bromide, and chloropicrin;
(25) selective homopteran feeding blockers:
pymetrozine, and flonicamid;
(26) mite growth inhibitors:
clofentezine, hexythiazox, and etoxazole;
(27) microbial disruptors of insect midgut membranes:
Bacillus thuringiensis;
(28) mitochondrial ATP synthase inhibitory compounds:
diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, and tetradifon;
(29) oxidative phosphorylation decoupling compounds:
chlorfenapyr;
(30) nicotinic acetylcholine receptor channel blockers:
bensultap, cartap, and thiocyclam;
(31) chitin biosynthesis inhibitory compounds:
chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, bistrifluoron, and noviflumuron;
(32) ecdysis/metamorphosis disrupting compounds:
cyromazine, chromafenozide, halofenozide, methoxyfenozide, and tebufenozide;
(33) octopamine receptor agonistic compounds:
amitraz;
(34) electron transport chain inhibitory compounds:
fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, rotenone, hydramethylnon, and acequinocyl;
(35) mitochondrial complex IV electron transport inhibitors:
aluminium phosphide;
(36) voltage-dependent sodium channel blockers:
indoxacarb, and metaflumizone;
(37) acetyl CoA carboxylase inhibitory compounds:
spirodiclofen, spiromesifen, and spirotetramat;
(38) ryanodine receptor modulators:
chlorantraniliprole, flubendiamide, and cyantraniliprol;
(39) compounds having unknown mode of actions:
azadirachtin, benzoximate, bifenazate, chinomethionat, dicofol, pyridalyl, pyrifluquinazon, and fluensulfone.

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Agri-Horticultural Pest Control Compositions Comprising 4-(3-Butynyl)Aminopyrimidine Derivatives

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Agri-Horticultural Pest Control Compositions Comprising 4-(3-Butynyl)Aminopyrimidine Derivatives

Life of this patent

Abstract

Claims7