WO2014149208A1 - Compositions pesticides à base de purine et procédés associés - Google Patents

Compositions pesticides à base de purine et procédés associés Download PDF

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Publication number
WO2014149208A1
WO2014149208A1 PCT/US2014/014719 US2014014719W WO2014149208A1 WO 2014149208 A1 WO2014149208 A1 WO 2014149208A1 US 2014014719 W US2014014719 W US 2014014719W WO 2014149208 A1 WO2014149208 A1 WO 2014149208A1
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Prior art keywords
alkyl
substituted
halogen
haloalkoxy
haloalkyl
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PCT/US2014/014719
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English (en)
Inventor
Mark A. Pobanz
William H. DENT
Chaoxian Geng
Akshay PATNY
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Dow Agrosciences Llc
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Publication of WO2014149208A1 publication Critical patent/WO2014149208A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • aspects and embodiments relate generally to pesticidal compositions and to methods of preparing and using such pesticidal compositions. Particular aspects and embodiments generally relate to purine-based pesticidal compositions and to the methods of producing and using such pesticidal compositions.
  • Controlling insect populations is essential to modern agriculture, food storage, and hygiene. There are more than ten thousand species of insects that cause losses in agriculture. The world-wide agricultural losses amount to billions of U.S. dollars each year. Accordingly, there exists a continuous need for new pesticides and for methods of producing and using such pesticides.
  • Embodiments of the present disclosure include purine-based compounds and pesticidal compositions comprising such purine-based compound.
  • Embodiments of the present disclosure further include methods of producing purine-based compounds.
  • Further embodiments of the present disclosure include methods of controlling pests that comprise applying a purine-based pesticidal composition near a population of pests.
  • alkyl refers to an acyclic, saturated, branched or unbranched, substituent consisting of carbon and hydrogen, for example, methyl, ethyl, propyl, isopropyl, 1 -butyl, 2-butyl, isobutyl, tert-butyl, pentyl, 2-methylbutyl, 1 ,1-dimethylpropyl, hexyl, heptyl, octyl, nonyl, and decyl.
  • cycloalkyl means a monocyclic or polycyclic, saturated substituent consisting of carbon and hydrogen, such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, norbornyl, bicycle[2.2.2]octyl, and decahydronapthyl .
  • alkenyl means and includes a straight, branched, or cyclic hydrocarbon containing at least one carbon-carbon double bond. Examples may include, but are not limited to, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, or decenyl.
  • cycloalkenyl means a cyclic hydrocarbon containing at least one carbon-carbon double bond, such as, for example, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, and cyclodecenyl.
  • alkynyl means and includes a straight, branched, or cyclic hydrocarbon containing at least one carbon-carbon triple bond. Examples may include, but are not limited to, ethynyl, propargyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, or decynyl.
  • aryl means and includes an aromatic ring compound with or without any substitution, such as, for example, phenyl and naphthyl.
  • alkoxy means and includes an alkyl or a cycloalkyl group containing at least one carbon-oxygen single bond. Non-limiting examples may include methoxy, ethoxy, propoxy, butoxy, cyclopropxy, cyclobutoxy, or cyclopentoxy.
  • alkylthio means and includes an alkyl group containing at least one carbon-sulfur single bond.
  • haloalkylthio means and includes an alkyl group containing at least one carbon-sulfur single bond and halogen atom.
  • halo and halogen mean and include fluorine, chlorine, bromine, or iodine.
  • heteroatom means and includes sulfur (S), oxygen (O) or nitrogen (N) atom.
  • heteroaryl means and includes an aromatic moiety containing at least one sulfur (S), oxygen (O), or nitrogen (N) atom in the aromatic ring.
  • Non-limiting examples may include furyl, pyridyl, pyrimidyl, thienyl, isothiazolyl, imidazolyl, tetrazolyl, pyrazinyl, benzofuranyl, benzothiophenyl, quinolyl, isoquinolyl, benzothienyl, isobenzofuryl, pyrazolyl, indolyl, isoindolyl, benzimidazolyl, purinyl, carbozolyl, oxazolyl, thiazolyl, isothiazolyl, 1 ,2,4-thiadiazolyl, isooxazolyl, pyrrolyl, pyrazolyl, quinazolinyl, pyridazinyl, pyrazinyl, cinnolinyl, phthalazinyl, quinoxalinyl, xanthinyl, hypoxanthinyl, pteridinyl,
  • heteroalkyl means and includes an alkyl moiety as defined herein containing at least one sulfur (S), oxygen (O), or nitrogen (N) atom.
  • cyano means and includes a functional group containing a carbon-nitrogen triple bond.
  • nitro means and includes a functional group containing a nitrogen atom joined to two oxygen atoms.
  • esticidally effective amount means and includes an amount of active material that causes an adverse effect to the at least one insect, wherein the adverse effect may include deviations from natural development, killing, regulation, or the like.
  • control means and includes regulating the number of living insects or regulating the number of viable eggs of the pests.
  • the pesticidal composition may comprise a purine compound having general formula I, or any agriculturally acceptable salt thereof:
  • Ar may be any aryl or heteroaryl moiety including, but not limited to, phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, pyrazolo, imidazolo, thiophenyl, furyl, or any other heteroaromatic ring system. Ar may be substituted or unsubstituted.
  • Ar may be substituted with alkoxy, cycloalkoxy, haloalkyl, cyclohaloalkyl, haloalkoxy, cyclohaloalkoxy, alkylthio, haloalkylthio, halothio, cyano, nitro, sulfone, sulfoxide, ester, acetate, amide, unsubstituted amines, substituted amines, unsubstituted aryloxy, substituted aryloxy, or combinations thereof;
  • R 2 , R.3, R4 and R 6 each may independently be selected from:
  • aryl or heteroaryl substituted with any combination of hydrogen, halogen, alkyl, cycloalkyl, alkoxy, cycloalkoxy, haloalkyl, cyclohaloalkyl, haloalkoxy, cyclohaloalkoxy, alkenyl, cycloalkenyl, alkynyl, alkylthio, haloalkylthio, halothio, cyano, nitro, sulfone, sulfoxide, ester, acetate, amide or substituted amine group, unsubstituted aryloxy, substituted aryloxy; and the alkyl, alkenyl, or alkynyl group may be substituted with one or more heteroatoms such as N, O, Si, or SO n (n 0, 1 , 2) at any position; or (i) an amino moiety substituted with hydrogen, C1 -C8 alkyl, C3-C8 cycloalkyl, C
  • the pesticidal composition may comprise a purine compound of formula I or any agriculturally acceptable salt thereof, wherein:
  • Ar, R 2 and R 3 each may be selected from the groups as described above,
  • R may be selected from the group consisting of C1-C8 alkyl substituted with at least two halogen atoms, C3-C8 cycloalkyl substituted with at least two halogen atoms, 0- Cl-C8) alkyl that may be substituted with at least two halogen atoms, 0 ⁇ (C3-C8) cycloalkyl that may be substituted with at least one halogen atom, phenyl substituted with at least one of halogen, haloalkyl and haloalkoxy, and heteroaiyl substituted with at least one of halogen, haloalkyl and haloalkoxy, and
  • R 6 may be selected from the group consisting of C1 -C8 alkyl, C1-C8 alkyl substituted with at least two halogen atoms, C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with at least two halogen atoms , 0-(Cl-C8) alkyl , 0- Cl-C8) alkyl that may be substituted with two halogen atoms, 0-(C3-C8) cycloalkyl , 0 ⁇ C3-C8) cycloalkyl that may be substituted with at least one halogen atom, phenyl substituted with at least one of halogen, haloalkyl and haloalkoxy, heteroaryl substituted with at least one of halogen, haloalkyl and haloalkoxy, O- phenyl substituted with at least one of halogen, haloalkyl and haloalkoxy, O- phenyl
  • the pesticidal composition may comprise a purine compound having general formula III or any agriculturally acceptable salt thereof, wherein Ar, R 2 , R3, R 4 and R ⁇ j are as described above.
  • the pesticidal composition may comprise a purine compound having general formula II-l or any agriculturally acceptable salt thereof, wherein Ar, R 4 , and R 6 are as described above.
  • the pesticidal composition may comprise a purine compound having general formula II-2 or any agriculturally acceptable salt thereof, wherein Ar and R 6 are as described above.
  • the pesticidal composition may comprise a purine compound having general formula II-3 or any agriculturally acceptable salt thereof:
  • Ar and Ar' each may be an aryl or heteroaryl group selected from the group consisting of furyl, phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, pyrazolo, imidazolo, and thiophenyl, and wherein the aryl group is substituted at any open position with at least one of hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, haloalkyl, haloalkoxy, alkylthio, haloalkylthio, halothio, cyano, nitro, sulfone, amines, aryloxy, and combinations thereof, and R-2 and R4 each may independently be selected from the group consisting of:
  • R' is selected from the group consisting of an alkyl moiety substituted with at least one heteroatom, aryl or heteroaryl with at least one substituent being any combination of halogen, alkoxy, haloalkyl, haloalkoxy, alkylthio, haloalkylthio, halothio, cyano, nitro, sulfone, and aryloxy;
  • the purine compounds of formula II and III may be produced by reacting 2-R6-4-N' V- H,R2-amine-6-R 4 -pyrimidine-5-amine compound XI with an aldehyde compound IV as shown in Scheme 1.
  • Scheme 1 2-R6-4-N' V- H,R2-amine-6-R 4 -pyrimidine-5-amine compound XI with an aldehyde compound IV as shown in Scheme 1.
  • the method of Scheme 1 may comprise reacting 2-R 6 -4-A r ', V- Ri ,R2-amine-6-R 4 -pyrimidine-5-amine compound XI with an aldehyde compound IV in a dry polar aprotic solvent, such as DMF, at temperature from about 80°C tol00°C to provide the purine compounds of formula II and HI.
  • a dry polar aprotic solvent such as DMF
  • the purine compounds of formula II-l and III-l may be produced by the method of Scheme 2, wherin R4 may be a (CI -C8)alkyl substituted with at least two or more halogen atoms, (C3-C8)cycloalkyl substituted with at least two or more halogen atoms, substituted aryl or substituted hetroaryl, R6 may be (Cl -C8)alkyl with or without substitutent, (C3-C8)cycloalkyl with or without substitutent, substituted phenyl or substituted hetroaryl, 0(C1 -C8)alkyl substituted, O-phenyl substituted, O-heteroaryl substituted, S(Cl -C8)alkyl substituted, S-phenyl substituted, S-heteroaryl substituted, N(Cl -C8)alkyl, N-phenyl substituted, N-heteroaryl substituted, where the substituent of the
  • the purine compounds II-l and III-l may be produced from the reaction of 2-R 6 -4-TV',TV'- R] ,R2-amine-6-R 4 -pyrimidine-5-amine compound XI with Ar-substituted aldehyde of formula IV-1, that is a substituted phenyl or substituted heteroaryl and iron (III) chloride (FeCl 3 ) adsorbed on silica gel, in a dry polar aprotic solvent, such as 1 ,4-dioxane, at temperatures between 80°C and 100°C for about 18 hours (h) to about 24 h.
  • a dry polar aprotic solvent such as 1 ,4-dioxane
  • the isolated residue may or may not be treated with an oxididant, such as 4,5-dichloro-3,6-dioxocyclohexa-l ,4-diene-l,2-dicarbonitrile (DDQ), to provide purine compounds II-l and III-l
  • wherin R4 may be a (Cl-C8)alkyl substituted with at least two or more halogen atoms, (C3-C8)cycloalkyl substituted with at least two or more halogen atoms, substituted aryl or substituted hetroaryl
  • 3 ⁇ 4 may be (Cl-C8)alkyl with or without substitutent, (C3-C8)cycloalkyl with or without substitutent, substituted phenyl or substituted hetroaryl, 0(C1 -C8)alkyl substituted, O-phenyl substituted, O-heteroaryl substituted, S(Cl-C8)alkyl substituted, S-phenyl substitute
  • compound 2-R ⁇ -4-N',N'-Ri,R 2 -amine-6-R ⁇ 4-pyrimidine-5-amine may be produced as shown in Scheme 3.
  • the phenyl diazonium salt may be prepared by reacting an aryl amine, such as aniline, in an acidic solvent such as concentrated hydrochloric acid (HC1) with an aqueous solution of sodium nitrite (NaN0 2 ) at a temperature from about - 10°C to about 10°C.
  • the method may include diazotizing compound R4-substituted- ? ⁇ diketoacetate (V) with phenyldiazonium salt in a basic solution, such as aqueous sodium acetate (NaOAc), at a temperature from about -10°C to about 10°C to provide the diazenyl-oxo-butanoates compound VI, then reacting compound VI with R 6 -substituted imidamide (VII) in the presence of base, such as sodium «-butoxide (NaO/zBu), in a polar protic solvent such as n-butanol to provide 2-R 6 -5-(phenyldiazenyl)-6-R 4 -pyrimidin-4-ol compound VIII.
  • a basic solution such as aqueous sodium acetate (NaOAc)
  • base such as sodium «-butoxide (NaO/zBu)
  • a polar protic solvent such as n-butanol
  • the hydroxy substituent group at the 4-position of the pyrimidinol compound VIII may be converted to the chloride group using a chlorinating reagent such as phosphorus oxychloride (POCI 3 ) in the presence of a base, such as NN-diethylaniline, at a temperature from about 100°C to about 1 10°C to provide 2-R 6 -4-chloro-5-(phenyldiazenyl)-6-R 4 -pyrimidine compound IX.
  • a chlorinating reagent such as phosphorus oxychloride (POCI 3 ) in the presence of a base, such as NN-diethylaniline, at a temperature from about 100°C to about 1 10°C to provide 2-R 6 -4-chloro-5-(phenyldiazenyl)-6-R 4 -pyrimidine compound IX.
  • Rj and R 2 are hydrogen atoms
  • a polar protic solvent such as methanol (MeOH)
  • Rj and R 2 are hydrogen atoms
  • a polar protic solvent such as methanol (MeOH)
  • R 2 is C1 -C8 alkyl with or without halogens
  • R 2 is an amine substituted with C1-C8 alkyl that is substituted and a protecting group such as BOC in a polar aprotic solvents, such as tetrahydrofuran (THF), at ambient temperature i.e.
  • THF tetrahydrofuran
  • 2-R 6 -4-N' 7V'-Ri,R 2 -amine-5-(phenyldiazenyl)-6-R 4 -pyrimidine compound X may be obtained. Then, the pyrimidine compound X may be subjected to hydrogenation to produce 2-R 6 -4-N'7V'-R),R 2 -amine-6-R 4 -pyrimidine-5-amine compound XI.
  • the hydrogenation of pyrimidine compound X may be performed in a polar protic solvent, such as EtOH, under a hydrogen atmosphere (1 atmosphere) at an RT stirring for 24 h to provide 2-R 6 -4-N',N'-Ri,R 2 -amine-6-R 4 -pyrimidine-5-amine compound XI, wherein R may be a (Cl-C8)alkyl substituted with at least two or more halogen atoms, (C3-C8)cycloalkyl substituted with at least two or more halogen atoms, substituted aryl or substituted hetroaryl, R 6 may be (Cl-C8)alkyl with or without substitutent, (C3-C8)cycloalkyl with or without substitutent, substituted phenyl or substituted hetroaryl, 0(C1-C8)alkyl substituted, O-phenyl substituted, O-heteroaryl substituted, S(Cl-C8)alkyl
  • XI may be produced as shown in Scheme 4.
  • the method may comprise reacting 2-chloro-4-7V',
  • N'-R] ,R2-amine-5-nitro-6-R 4 -pyrimidine compound XII with an alcohol (e.g., MeOH) and a base (e.g., pyridine), or with a thiol (e.g., methanethiol) and a base (e.g., sodium) in a polar aprotic solvent such as THF at an RT for 24 h to provide 2-R6-4- V',N'-Ri ,R2-amine-5-nitro-6-R 4 -pyrimidine compound XIII, as described in Clark, J. et al. J. Chem. Soc.
  • (C), 1971, 12, 2278-2282, wherein 3 ⁇ 4 may be 0-(Cl-C8) alkyl substituted, O-phenyl substituted with halogen, alkyl, haloalkyl, alkoxy or haloalkoxy, O-heteroaryl substituted with halogen, alkyl, haloalkyl, alkoxy or haloalkoxy, S-(C1-C8)alkyl substituted, S- phenyl substituted with halogen, alkyl, haloalkyl, alkoxy or haloalkoxy, and S-heteroaryl substituted with halogen, alkyl, haloalkyl, alkoxy or haloalkoxy.
  • the nitro substituent group on compound XIII may be reduced with sodium hyposulfite (Na 2 S 2 0 3 ) and a base, such as an aqueous saturated sodium bicarbonate (NaHC0 3 ) solution, in a polar solvent such as acetone at an RT for about 20 minutes (min) to about 1 h to provide 2-R 6 -4-N',N'-R 1 ,R 2 -amine-6-R 4 -pyrimidine-5-amine compound XI.
  • sodium hyposulfite Na 2 S 2 0 3
  • a base such as an aqueous saturated sodium bicarbonate (NaHC0 3 ) solution
  • a polar solvent such as acetone
  • the purine compounds of formula II-l may be produced by reacting protected compound II with an acid to remove the protecting group, as shown in Scheme 5.
  • the method of Scheme 5 may comprise reacting the protected compound II in a solvent, such as dichloromethane (CH2CI2), with triethylsilane and trifluoroacetic acid (TFA) at a temperature of about 40°C for about four h.
  • a solvent such as dichloromethane (CH2CI2)
  • TFA trifluoroacetic acid
  • the pesticidal composition comprising a purine compound of formula I may be used to control a wide variety of pests.
  • the pesticidal composition comprising a purine compound of formula I may be used to control one or more members of at least one of Phylum Arthropoda, Phylum Nematoda, Subphylum Chelicerata, Subsphylum Myriapoda, Subphylum Hexapoda, Class Insecta, Class Arachnida, and Class Symphyla.
  • the method of the present disclosure may be used to control one or more members of at least one of Class Insecta and Class Arachnida.
  • the method of the present disclosure may be used to control one or more members of at least one of Phylum Arthropoda, Phylum Nematoda, Subphylum Chelicerata, Subsphylum Myriapoda, Subphylum Hexapoda, Class Insecta, Class Arachnida, and Class Symphyla.
  • the method of the present disclosure may be used to control one or more members of at least one of Class Insecta and Class Arachnida.
  • the method of the present disclosure may be used to control members of the Order Coleoptera (beetles) including, but not limited to, Acanthoscelides spp. (weevils), Acanthoscelides obtectus (common bean weevil), Agrilus planipennis (emerald ash borer), Agriotes spp. (wireworms), Anoplophora glabripennis (Asian longhorned beetle), Anthonomus spp. (weevils), Anthonomus grandis (boll weevil), Aphidius spp., Apion spp. (weevils), Apogonia spp.
  • Acanthoscelides spp. (weevils)
  • Acanthoscelides obtectus common bean weevil
  • Agrilus planipennis emerald ash borer
  • Agriotes spp. wireworms
  • Ataenius spretulus Black Turfgrass Ataenius
  • Atomaria linearis pygmy mangold beetle
  • Aulacophore spp. Bothynoderes punctiventris (beet root weevil), Bruchus spp. (weevils), Bruchus pisorum (pea weevil), Cacoesia spp., Callosobruchus maculatus (southern cow pea weevil), Carpophilus hemipteras (dried fruit beetle), Cassida vittata, Cerosterna spp., Cerotoma spp.
  • the method of the present disclosure may be used to control members of the Order Dermaptera (earwigs).
  • the method of the present disclosure may be used to control members of the Order Dictyoptera (cockroaches) including, but is not limited to, Blattella germanica (German cockroach), Blatta orientalis (oriental cockroach), Parcoblatta pennylvanica, Periplaneta americana (American cockroach), Periplaneta australoasiae (Australian cockroach), Periplaneta brunnea (brown cockroach), Periplaneta fuliginosa (smokybrown cockroach), Pyncoselus suninamensis (Surinam cockroach), and Supella longipalpa (brownbanded cockroach).
  • cockroaches including, but is not limited to, Blattella germanica (German cockroach), Blatta orientalis (oriental cockroach), Parcoblatta pennylvanica, Periplaneta americana (American cockroach), Periplaneta australoasiae (Australian cockroach), Periplan
  • the method of the present disclosure may be used to control members of the Order Diptera (true flies) including, but is not limited to, Aedes spp. (mosquitoes), Agromyza frontella (alfalfa blotch leafminer), Agromyza spp. (leaf miner flies), Anastrepha spp. (fruit flies), Anastrepha suspensa (Caribbean fruit fly), Anopheles spp. (mosquitoes), Batrocera spp. (fruit flies), Bactrocera cucurbitae (melon fly), Bactrocera dorsalis (oriental fruit fly), Ceratitis spp.
  • Aedes spp. mosquitoes
  • Agromyza frontella alfalfa blotch leafminer
  • Agromyza spp. leaf miner flies
  • Anastrepha spp. fruit flies
  • Muscid flies Musca autumnalis (face fly), Musca domestica (house fly), Oestrus ovis (sheep bot fly), Oscinella frit (frit fly), Vegomyia betae (beet leafminer), Phorbia spp., PsUa rosae (carrot rust fly), Rhagoletis cerasi (cherry fruit fly), Rhagoletis pomonella (apple maggot), Sitodiplosis mosellana (orange wheat blossom midge), Stomoxys calcitrans (stable fly), Tabanus spp. (horse flies), and Tipula spp. (crane flies).
  • the method of the present disclosure may be used to control members of the Order Hemiptera (true bugs) including, but is not limited to, Acrosternum hilare (green stink bug), Blissus leucopterus (chinch bug), Calocoris norvegicus (potato mirid), Cimex hemipterus (tropical bed bug), Cimex lectularius (bed bug), Dagbertus fasciatus, Dichelops furcatus, Dysdercus suturellus (cotton stainer), Edessa meditabunda, Eurygaster maura (cereal bug), Euschistus heros, Euschistus servus (brown stink bug), Helopeltis antonii, Helopeltis theivora (tea blight plantbug), Lagynotomus spp.
  • Acrosternum hilare green stink bug
  • Blissus leucopterus chinch bug
  • Calocoris norvegicus pot
  • the method of the present disclosure may be used to control members of the Order Homoptera (aphids, scales, whiteflies, leaflhoppers) including, but is not limited to, Acrythosiphon pisum (pea aphid), Adelges spp. (adelgids), Aleurodes proletella (cabbage whitefly), Aleurodicus disperses, Aleurothrixus floccosus (woolly whitefly), Aluacaspis spp., Amrasca bigutella bigutella, Aphrophora spp. (leafhoppers), Aonidiella aurantii (California red scale), Aphis spp.
  • Acrythosiphon pisum pea aphid
  • Adelges spp. Adelges spp.
  • Aleurodes proletella cabbage whitefly
  • Aleurodicus disperses Aleurothrixus floccosus (woo
  • Aphids Aphis gossypii (cotton aphid), Aphis pomi (apple aphid), Aulacorthum solani (foxglove aphid), Bemisia spp. (whiteflies), Bemisia argentifolii, Bemisia tabaci (sweetpotato whitefly), Brachycolus noxius (Russian aphid), Brachycorynella asparagi (asparagus aphid), Brevennia rehi, Brevicoiyne brassicae (cabbage aphid), Ceroplastes spp.
  • Rhapalosiphum spp. aphids
  • Rhapalosiphum maida corn leaf aphid
  • Rhapalosiphum padi oat bird-cherry aphid
  • Saissetia spp. scales
  • Saissetia oleae black scale
  • Schizaphis graminum greenbug
  • Sitobion avenae English grain aphid
  • Sogatella furcifera white-backed planthopper
  • the method of the present disclosure may be used to control Myzus persicae.
  • the method of the present disclosure may be used to control members of the Order Hymenoptera (ants, wasps, and bees) including, but not limited to, Acromyrrmex spp., Athalia rosae, Atta spp. (leafcutting ants), Camponotus spp. (carpenter ants), Diprion spp. (sawflies), Formica spp. (ants), Iridomyrmex humilis (Argentine ant), Monomorium ssp., Monomorium minumum (little black ant), Monomorium pharaonis (Pharaoh ant), Neodiprion spp. (sawflies), Pogonomyrmex spp.
  • Acromyrrmex spp. Athalia rosae
  • Atta spp. leafcutting ants
  • Camponotus spp. carpenter ants
  • Diprion spp. sawflies
  • the method of the present disclosure may be used to control members of the Order Isoptera (termites) including, but not limited to, Coptotermes spp., Coptotermes curvignathus, Coptotermes frenchii, Coptotermes formosanus (Formosan subterranean termite), Cornitermes spp. (nasute termites), Cryptotermes spp. (drywood termites), Heterotermes spp. (desert subterranean termites), Heterotermes aureus, Kalotermes spp. (drywood termites), Incistitermes spp. (drywood termites), Macrotermes spp. (fungus growing termites), Marginitermes spp.
  • Coptotermes spp. Coptotermes curvignathus, Coptotermes frenchii, Coptotermes formosanus (Formosan subterranean termite), Cornitermes spp. (nasute termites), Cryptotermes spp. (drywood termites), Heterotermes
  • the method of the present disclosure may be used to control members of the Order Lepidoptera (moths and butterflies) including, but not limited to, Achoea janata, Adoxophyes spp., Adoxophyes orana, Agrotis spp.
  • members of the Order Lepidoptera including, but not limited to, Achoea janata, Adoxophyes spp., Adoxophyes orana, Agrotis spp.
  • Pseud moths Pseudaletia unipunctata (armyworm), Pseudoplusia includens (soybean looper), Rachiplusia nu, Scirpophaga inceriulas, Sesamia spp. (stemborers), Sesamia inferens (pink rice stem borer), Sesamia nonagrioides, Setora nitens, Sitotroga cerealella (Angoumois grain moth), Sparganothis pilleriana, Spodoptera spp.
  • the method of the present disclosure may be used to control Spodoptera exigua.
  • the method of the present disclosure may be used to control members of the Order Mallophaga (chewing lice) including, but not limited to, Bovicola ovis (sheep biting louse), Menacanthus stramineus (chicken body louse), and Menopon gallinea (common hen house).
  • the method of the present disclosure may be used to control members of the Order Orthoptera (grasshoppers, locusts, and crickets) including, but not limited to, Anabrus simplex (Mormon cricket), Gryllotalpidae (mole crickets), Locusta migratoria, Melanoplus spp. (grasshoppers), Microcentrum retinerve (angularwinged katydid), Pterophylla spp. (kaydids), chistocerca gregaria, Scudderia furcata (forktailed bush katydid), and Valanga nigricorni.
  • the method of the present disclosure may be used to control members of the Order Phthiraptera (sucking lice) including, but not limited to, Haematopinus spp. (cattle and hog lice), Linognathus ovillus (sheep louse), Pediculus humanus capitis (human body louse), Pediculus humanus humanus (human body lice), and Pthirus pubis (crab louse).
  • the method of the present disclosure may be used to control members of the Order Siphonaptera (fleas) including, but not limited to, Ctenocephalides canis (dog flea), Ctenocephalides felis (cat flea), and Pulex irritans (human flea).
  • the method of the present disclosure may be used to control members of the Order Thysanoptera (thrips) including, but not limited to, Frankliniella fusca (tobacco thrips), Frankliniella occidentalis (western flower thrips), Frankliniella shultzei, Frankliniella williamsi (corn thrips), Heliothrips haemorrhaidalis (greenhouse thrips), Riphiphorothrips cruentatus, Scirtothrips spp., Scirtothrips citri (citrus thrips), Scirtothrips dorsalis (yellow tea thrips), Taeniothrips rhopalantennalis, and Thrips spp.
  • Thysanoptera including, but not limited to, Frankliniella fusca (tobacco thrips), Frankliniella occidentalis (western flower thrips), Frankliniella shultzei, Frankliniella williamsi (
  • the method of the present disclosure may be used to control members of the Order Thysanura (bristletails) including, but not limited to, Lepisma spp. (silverfish) and Thermobia spp. (firebrats).
  • Thysanura bristletails
  • Lepisma spp. silverfish
  • Thermobia spp. firebrats
  • the method of the present disclosure may be used to control members of the Order Acari (mites and ticks) including, but not limited to, Acarapsis woodi (tracheal mite of honeybees), Acarus spp. (food mites), Acarus siro (grain mite), Aceria mangiferae (mango bud mite), Aculops spp., Aculops lycopersici (tomato russet mite), Aculops pelekasi, Aculus pelekassi, Aculus convincedendali (apple rust mite), Amblyomma americanum (lone star tick), Boophilus spp.
  • Acarapsis woodi tracheal mite of honeybees
  • Acarus spp. food mites
  • Acarus siro grain mite
  • Aceria mangiferae mango bud mite
  • Aculops spp. Aculops lycopersici (tomato russet mite)
  • the method of the present disclosure may be used to control members of the Order Nematoda (nematodes) including, but not limited to, Aphelenchoides spp. (bud and leaf& pine wood nematodes), Belonolaimus spp. (sting nematodes), Criconemella spp. (ring nematodes), Dirofilaria immitis (dog heartwom), Ditylenchusspp. (stem and bulb nematodes), Heterodera spp. (cyst nematodes), Heterodera zeae (corn cyst nematode), Hirschmanniella spp. (root nematodes), Hoplolaimus spp.
  • Aphelenchoides spp. bud and leaf& pine wood nematodes
  • Belonolaimus spp. sting nematodes
  • Criconemella spp. ring nematodes
  • Dirofilaria immitis dog heartwo
  • the method of the present disclosure may be used to control at least one insect in one or more of the Orders Lepidoptera, Coleoptera, Homoptera, Hemiptera, Thysanoptera, Isoptera, Orthoptera, Diptera, Hymenoptera, and Siphonaptera, and at least one mite in the Order Acari.
  • CEW Cabbage Looper
  • CL Cabbage Looper
  • BAW has few effective parasites, diseases, or predators to lower its population.
  • BAW infests many weeds, trees, grasses, legumes, and field crops. In various places, it is of economic concern upon asparagus, cotton, corn, soybeans, tobacco, alfalfa, sugar beets, peppers, tomatoes, potatoes, onions, peas, sunflowers, and citrus, among other plants.
  • CEW is known to attack corn and tomatoes, but it also attacks artichoke, asparagus, cabbage, cantaloupe, collards, cowpeas, cucumbers, eggplant, lettuce, lima beans, melon, okra, peas, peppers, potatoes, pumpkin, snap beans, spinach, squash, sweet potatoes, and watermelon, among other plants.
  • CEW is also known to be resistant to certain insecticides.
  • CL feeds on a wide variety of cultivated plants and weeds. It feeds readily on crucifers, and has been reported damaging broccoli, cabbage, cauliflower, Chinese cabbage, collards, kale, mustard, radish, rutabaga, turnip, and watercress.
  • Other vegetable crops injured include beet, cantaloupe, celery, cucumber, lima bean, lettuce, parsnip, pea, pepper, potato, snap bean, spinach, squash, sweet potato, tomato, and watermelon.
  • CL is also known to be resistant to certain insecticides. Consequently, because of the above factors control of these pests is important. Furthermore, molecules that control these pests are useful in controlling other pests.
  • Bioassays on BAW were conducted using a 128-well diet tray assay.
  • One to five second instar BAW larvae were placed in each well (3 mL) of the diet tray that had been previously filled with 1 mL of artificial diet to which 50 ⁇ of the test compound (dissolved in 50 of 90:10 acetone-water mixture) had been applied (to each of eight wells) and then allowed to dry.
  • Trays were covered with a clear self-adhesive cover, and held at 25°C, 14: 10 light-dark for five to seven days. Percent mortality was recorded for the larvae in each well; activity in the eight wells was then averaged. The results are indicated in the tables entitled "Table 1" (See Table Section).
  • Bioassays on CEW were conducted using a 128-well diet tray assay.
  • One to five second instar CEW larvae were placed in each well (3 mL) of the diet tray that had been previously filled with 1 mL of artificial diet to which 50 ⁇ g /cm " of the test compound (dissolved in 50 ⁇ xL of 90:10 acetone-water mixture) had been applied (to each of eight wells) and then allowed to dry. Trays were covered with a clear self-adhesive cover, and held at 25°C, 14:10 light-dark for five to seven days. Percent mortality was recorded for the larvae in each well; activity in the eight wells was then averaged. The results are indicated in the table entitled "Table 1" (See Table Section).
  • Bioassays on CL were conducted using a 128-well diet tray assay.
  • One to five second instar CL larvae were placed in each well (3 mL) of the diet tray that had been previously filled with 1 mL of artificial diet to which 50 ⁇ g /cm 2 of the test compound (dissolved in 50 of 90:10 acetone-water mixture) had been applied (to each of eight wells) and then allowed to dry.
  • Trays were covered with a clear self-adhesive cover, and held at 25°C, 14:10 light-dark for five to seven days. Percent mortality was recorded for the larvae in each well; activity in the eight wells was then averaged. The results are indicated in the table entitled "Table 1" (See Table Section).
  • Example B Bioassays on Green Peach Aphid (“GPA”) (Myzus persicae).
  • GPA is the most significant aphid pest of peach trees, causing decreased growth, shriveling of the leaves, and the death of various tissues. It is also hazardous because it acts as a vector for the transport of plant viruses, such as potato viais Y and potato leafroll virus to members of the nightshade/potato family Solanaceae, and various mosaic viruses to many other food crops. GPA attacks such plants as broccoli, burdock, cabbage, carrot, cauliflower, daikon, eggplant, green beans, lettuce, macadamia, papaya, peppers, sweet potatoes, tomatoes, watercress, and zucchini, among other plants. GPA also attacks many ornamental crops such as carnation, chrysanthemum, flowering white cabbage, poinsettia, and roses. GPA has developed resistance to many pesticides.
  • the seedlings were infested with 20-50 GPA (wingless adult and nymph stages) one day prior to chemical application.
  • Test compounds (2 mg) were dissolved in 2 mL of acetone/MeOH (1 :1) solvent, forming stock solutions of 1000 ppm test compound.
  • the stock solutions were diluted 5X with 0.025% Tween 20 in H 2 0 to obtain the solution at 200 ppm test compound.
  • a hand-held aspirator-type sprayer was used for spraying a solution to both sides of cabbage leaves until runoff.
  • Reference plants (solvent check) were sprayed with the diluent only containing 20% by volume of acetone/MeOH (1 :1) solvent. Treated plants were held in a holding room for three days at approximately 25°C and ambient relative humidity (RH) prior to grading. Evaluation was conducted by counting the number of live aphids per plant under a microscope. Percent Control was measured by using Abbott's correction formula (W.S. Abbott, "A Method of Computing the Effectiveness of an Insecticide" J. Econ. Entomol. 18 (1925), pp.265-267) as follows.
  • Example C BlOASSAYS ON Yellow Fever Mosquito "YFM" (Aedes aegypti).
  • YFM prefers to feed on humans during the daytime and is most frequently found in or near human habitations.
  • YFM is a vector for transmitting several diseases. It is a mosquito that can spread the dengue fever and yellow fever viruses. Yellow fever is the second most dangerous mosquito-borne disease after malaria. Yellow fever is an acute viral hemorrhagic disease and up to 50% of severely affected persons without treatment will die from yellow fever. There are an estimated 200,000 cases of yellow fever, causing 30,000 deaths, worldwide each year. Dengue fever is a nasty, viral disease; it is sometimes called "breakbone fever” or "break-heart fever” because of the intense pain it can produce. Dengue fever kills about 20,000 people annually. Consequently, because of the above factors control of this pest is important. Furthermore, molecules that control this pest (YFM), which is known as a sucking pest, are useful in controlling other pests that cause human and animal suffering.
  • Master plates containing 400 ⁇ g of a molecule dissolved in 100 of dimethyl sulfoxide (DMSO) (equivalent to a 4000 ppm solution) are used.
  • a master plate of assembled molecules contains 15 ⁇ , per well.
  • 135 of a 90: 10 watenacetone mixture is added to each well.
  • a robot Biomek® NXP Laboratory Automation Workstation
  • a robot is programmed to dispense 15 aspirations from the master plate into an empty 96-well shallow plate ("daughter” plate).
  • mosquito eggs are placed in Millipore water containing liver powder to begin hatching (4 g. into 400 ml). After the daughter plates are created using the robot, they are infested with 220 ⁇ , of the liver powder/larval mosquito mixture (about 1 day-old larvae). After plates are infested with mosquito larvae, a non-evaporative lid is used to cover the plate to reduce drying. Plates are held at RT for 3 days prior to grading. After 3 days, each well is observed and scored based on mortality.
  • TABLE 1 shows the pesticidal activities of the benzimidazole compounds against several insects: beet armyworm (BAW), corn earworm (CEW), cabbage looper (CL), green peach aphid (GPA), and yellow fever mosquitoes (YFM).
  • BAW beet armyworm
  • CEW corn earworm
  • CL cabbage looper
  • GPA green peach aphid
  • YFM yellow fever mosquitoes
  • the mortality efficiency of the benzimidazole compounds against BAW, CEW, CL and GPA insects is determined after five days of treatment.
  • the mortality efficiency against YFM is determined after three days of treatment.
  • the mortality efficiency is rated as shown in TABLES 2-4.
  • TABLE 1 shows the mortality study results of the purine compounds 1-106 against several insects: beet armyworm (BAW), corn earworm (CEW), cabbage looper (CL), green peach aphid (GPA), and yellow fever mosquitos (YFM).
  • Embodiments of the present disclosure further include methods of controlling pests that comprises applying an pesticidal composition comprising a purine compound of the general formula I near a population of pests.
  • the pesticidal composition may comprise a purine compound of the general formula I in a phytologically-acceptable inert carrier (e.g., solid carrier or liquid carrier), and may be applied near a population of pests.
  • a phytologically-acceptable inert carrier e.g., solid carrier or liquid carrier
  • the control of insects may be achieved by applying an pesticidally effective amount of the purine-based composition in form of sprays, topical treatment, gels, seed coatings, microcapsulations, systemic uptake, baits, eartags, boluses, foggers, fumigants aerosols, dusts, or the like.
  • the purine-based pesticidal compositions may be in the form of solid.
  • the solid forms may include power, dust or granular formulations.
  • the purine-based pesticidal compositions may be in the form of liquid formulation.
  • the liquid forms may include, but not limited to, dispersion, suspension, emulsion or solution in appropriate liquid carrier.
  • the purine-based pesticidal compositions may be in the form of liquid dispersion, wherein the purine compound may be dispersed in water or other agriculturally suitable liquid carrier.
  • the purine-based pesticidal compositions may be in the form of solution in an appropriate organic solvent.
  • the spray oils which are widely used in agricultural chemistry, may be used as the organic solvent for the purine-based pesticidal compositions.
  • the purine-based pesticidal compositions may be used in conjunction with at least one of other pesticides, fungicides and herbicides to obtain control of a wider variety of pests, diseases and weeds.
  • the purine-based pesticidal compositions may be formulated with the other pesticides or fungicides or herbicide, or applied sequentially with the other pesticides or fungicides or herbicides.
  • aniline (21.2 g, 228 mmol) was dissolved in concentrated HC1 (65 mL) and mixed at 0°C with a solution of NaN0 2 (17.7 g, 256 mmol) in distilled water (36 mL). To this mixture was slowly added a solution of NaOAc (183 g, 2231 mmol) in distilled water (440 mL) with continuous stirring, and the temperature was kept at 0°C.
  • compound XI-23, XI -24, XI -25, XI-26, XI-27, XI-28, XI-29, XI-38, XI-39 and XI-40 (1 eq.) each was mixed with an appropriate aldehyde (2 eq.) in anhydrous dioxane (5 mL).
  • the reaction mixture was treated with FeCl 3 /Si0 2 (15%, 2 eq.) at 100°C under nitrogen for 18 h.
  • the cooled mixture was filtered and washed with EtOAc (2 x 15 mL).
  • Aldehydes used include: 2,6-dichlorobenzaldehyde, 2,6-dichloro-4-(trifluoromethyl) benzaldehyde, 2-chloro-5-(trifluoromethyl)benzaldehyde, 3-chlorothiophene-2-carbaldehyde, 2,4-dicWorobenzaldehyde,2-chloro-4-(dimethylamino)benzaldehyde,2-chloro-6-methylbenzalde hyde, 2-methoxy-4-(trifluoromethyl)benzaldehyde, 2-fluoro-4-(trifluoromethyl)-benzaldehyde, 2,4,6-tricUorobenzaldehyde,2,5-dicUorothiophene-3-carbaldehyde,5-chloro-thiophene-2-carbal dehyde,5-(trifluoromethyl)picolinaldehyde,2,6-di
  • reaction mixture was poured into a separatory funnel containing CH 2 CI 2 (50 mL), washed with sodium hydroxide (NaOH) aqueous solution (1 N, 3 x 25 mL). The aqueous layer was back-extracted with CH 2 CI 2 (1 x 25mL), and combined with the organic phases. The combined organic phases were dried over magnesium sulfate (MgS0 4 ), and filtered. After addition of S1O 2 (5g), the solvent was removed under vacuum. The residue was purified by column chromatography (hexanes - EtOAc:gradient; 25g column) to afford the purine Compound 86 and Compound 87.
  • NaOH sodium hydroxide
  • tert-butyl (8-(2-methoxy-4-(trifluoromethyl)phenyl)-6-(trifluoromethyl)-2- (6-(trifluoromethyl)pyridin-3-y)-9H-purin-9-yl)carbamate
  • Compound 93 and tert-butyl (8-(2-methoxy-4-(trifluoromethyl)phenyl)-6-(trifluoromethyl)-2-(6-(trifluoromethyl)pyridin-3-y) -7H-purin-9(8H)-yl)carbamate
  • Compound 94 was prepared from -methoxy-4-(trifluoromethyl)-benzaldehyde).

Abstract

L'invention concerne une composition pesticide comprenant un composé de purine de formule générale I, ou tout sel acceptable dans l'agriculture de celui-ci, formule dans laquelle Ar, R2, R3, R4 et R6 sont tels que décrits dans la description. L'invention concerne également une composition pesticide, comprenant un composé de purine de formule générale I ou tout sel acceptable dans l'agriculture de celui-ci. L'invention concerne également des procédés de préparation de telles compositions pesticides et le procédé de lutte contre les insectes à l'aide des compositions pesticides.
PCT/US2014/014719 2013-03-15 2014-02-04 Compositions pesticides à base de purine et procédés associés WO2014149208A1 (fr)

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JP2018509416A (ja) * 2015-03-12 2018-04-05 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ 複素環置換二環式アゾール殺有害生物剤
WO2022023439A1 (fr) * 2020-07-29 2022-02-03 King's College London Composés radiomarqués
CN114929809A (zh) * 2020-01-15 2022-08-19 亨斯迈先进材料（瑞士）有限公司 分散偶氮染料、其制备方法及其用途
WO2023058003A1 (fr) * 2021-10-07 2023-04-13 Tme Therapeutics Llc Nouveaux inhibiteurs de la pikfyve et leurs méthodes d'utilisation

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WO2005092892A1 (fr) * 2004-03-26 2005-10-06 Dainippon Sumitomo Pharma Co., Ltd. Compose 8-oxoadenine
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JP2018509416A (ja) * 2015-03-12 2018-04-05 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ 複素環置換二環式アゾール殺有害生物剤
WO2017025419A3 (fr) * 2015-08-07 2017-04-06 Bayer Cropscience Aktiengesellschaft Dérivés d'hétérocycles condensés à substitution 2-(het)aryle utilisés comme agents de lutte contre les nuisibles
JP2018523664A (ja) * 2015-08-07 2018-08-23 バイエル・クロップサイエンス・アクチェンゲゼルシャフト 有害生物防除剤としての２−（ヘタ）アリール−置換縮合ヘテロ環誘導体
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US10986840B2 (en) 2015-08-07 2021-04-27 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted fused heterocycle derivatives as pesticides
CN114929809A (zh) * 2020-01-15 2022-08-19 亨斯迈先进材料（瑞士）有限公司 分散偶氮染料、其制备方法及其用途
CN114929809B (zh) * 2020-01-15 2023-12-15 亨斯迈纺织染化(瑞士)有限公司 分散偶氮染料、其制备方法及其用途
WO2022023439A1 (fr) * 2020-07-29 2022-02-03 King's College London Composés radiomarqués
CN116322673A (zh) * 2020-07-29 2023-06-23 伦敦国王学院 放射性标记的化合物
WO2023058003A1 (fr) * 2021-10-07 2023-04-13 Tme Therapeutics Llc Nouveaux inhibiteurs de la pikfyve et leurs méthodes d'utilisation

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