WO2006105056A2 - 2,4-diaminoquinazolines insecticides et derives associes - Google Patents

2,4-diaminoquinazolines insecticides et derives associes Download PDF

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WO2006105056A2
WO2006105056A2 PCT/US2006/011218 US2006011218W WO2006105056A2 WO 2006105056 A2 WO2006105056 A2 WO 2006105056A2 US 2006011218 W US2006011218 W US 2006011218W WO 2006105056 A2 WO2006105056 A2 WO 2006105056A2
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optionally substituted
compound
group
halogen
hydrogen
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WO2006105056A3 (fr
Inventor
John A. Dixson
Elizabeth G. Rowley
Saroj Sehgel
Thomas G. Cullen
Michael J. Wyle
Frank J. Zawacki
Louis V. Lafrance Iii
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FMC Corp
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FMC Corp
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    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • the present invention generally relates to pesticidal compounds and their use in controlling insects and acarids.
  • it pertains to compositions of insecticidal 2,4-diaminoquinazolines, related derivatives and agriculturally acceptable salts thereof, and methods for their use in controlling insects and acarids.
  • insects in general can cause significant damage, not only to crops grown in agriculture, but also, for example, to structures and turf where the damage is caused by soil-borne insects, such as termites and white grubs. Such damage may result in the loss of millions of dollars of value associated with a given crop, turf or structures.
  • Insecticides and acaricides are useful for controlling insects and acarids which may otherwise cause significant damage to crops such as wheat, corn, soybeans, potatoes, and cotton to name a few.
  • insecticides and acaricides are desired which can control the insects and acarids without damaging the crops, and which have no deleterious effects to mammals and other living organisms.
  • R is selected from the group consisting of hydrogen, haloalkyl, alkoxyalkyl, alkphenylalkyl, alkoxycarbonylalkyl, alkthioalkyl, alkoxycarbonylaminoalkyl, phenoxycarbonylaminoalkyl, phenylcarbonylalkyl, optionally substituted cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl and optionally substituted cycloalkalkyl, wherein the optional substituents are selected from the group consisting of halogen, alkyl, aryl, alkamino, dialkylamino, alkenylalkyl, alkynylalkyl, carbonylaryl, phenylalkyl, alkoxycarbonyl, haloalkcarbonyl, alkoxyalkyl, 3-pyridylcarbonyl, heterocyclyl, phenoxythionyl, phenylaminocarbonyl, pheny
  • R 6 and R 10 are independently selected from the group consisting of halogen, alkyl, alkoxy and cyano, and wherein * denotes a point of attachment;
  • R 2 and R 4 are independently selected from hydrogen or alkylcarbonyl;
  • R 5 is selected from the group consisting of optionally substituted aryloxy, optionally substituted cycloalkyl and
  • optional substituents are independently selected from the group consisting of halogen, alkyl, alkoxy, haloalkyl, haloalkoxy and SF 5
  • R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, SF 5 and either of R and
  • R 8 , or R 8 and R 9 taken together with -OCH 2 O-, -OC(CH 3 ) 2 CH 2 - or -OC(CH 3 ) 2 O-, forming a benzo-fused ring; and the corresponding agriculturally acceptably salts thereof.
  • the present invention is also directed to methods of controlling insects, where control is desired, which comprise applying an insecticidally effective amount of the above composition to the locus of crops, or other areas where insects are present or are expected to be present.
  • One aspect of the present invention relates to certain new and useful compounds, namely novel 2,4-diaminoquinazolines and related derivatives (hereinafter termed "compounds of formula I") as depicted in formula I:
  • R is selected from the group consisting of hydrogen, haloalkyl, alkoxyalkyl, alkphenylalkyl, alkoxycarbonylalkyl, alkthioalkyl, alkoxycarbonylarninoalkyl, phenoxycarbonylaminoalkyl, phenylcarbonylalkyl, optionally substituted cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl and optionally substituted cycloalkalkyl, wherein the optional substituents are selected from the group consisting of halogen, alkyl, aryl, alkamino, dialkylamino, alkenylalkyl, alkynylalkyl, carbonylaryl, phenylalkyl, alkoxycarbonyl, haloalkcarbonyl, alkoxyalkyl, 3-pyridylcarbonyl, heterocyclyl, phenoxythionyl, phenylaminocarbonyl, phen
  • A is selected from the group consisting of optionally substituted cycloalkyl, optionally substituted thiopheneyl,
  • R 2 and R 4 are independently selected from hydrogen or alkylcarbonyl
  • R 5 is selected from the group consisting of optionally substituted aryloxy, optionally substituted cycloalkyl and
  • optional substituents are independently selected from the group consisting of halogen, alkyl, alkoxy, haloalkyl, haloalkoxy and SF 5
  • R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, SF 5 and either of R 7 and R 8 , or R 8 and R 9 taken together with -OCH 2 O-, -OC(CH 3 ) 2 CH 2 - or -OC(CH 3 ) 2 O-, forming a benzo-fused ring; and the corresponding agriculturally acceptably salts thereof.
  • Preferred species of the present invention are those compounds of formula I where R 2 is hydrogen and A is
  • More preferred species of the present invention are those compounds of formula I where R 2 is hydrogen, A is
  • R 4 is hydrogen and R 5 is
  • R , R and R are independently selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, SF 5 and either of R 7 and R 8 , or R 8 and R 9 taken together with -OCH 2 O-, -OC(CH 3 ) 2 CH 2 - or -OC(CH 3 ) 2 O-, forming a benzo-fused ring.
  • R 4 is hydrogen and R 5 is
  • R 8 is hydrogen
  • R and R 9 are independently selected from the group consisting of halogen, haloalkyl and haloalkoxy, and R is
  • Z 1 is selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, haloalkyl and haloalkoxy; more particularly wherein R 7 , R 9 and Z 1 are halogen.
  • R is selected from the group consisting of
  • R 14 , R 22 , R 26 and R 27 are independently selected from the group consisting of
  • R 5 is selected from the group consisting of
  • the compounds of the present invention may possess asymmetric centers, which can give rise to optical enantiomorphs and diastereomers.
  • the compounds may exist in two or more forms, i.e., polymorphs, which are significantly different in physical and chemical properties.
  • the compounds of the present invention may also exist as tautomers, in which migration of a hydrogen atom within the molecule results in two or more structures, which are in equilibrium.
  • the compounds of the present invention may also possess acidic or basic moieties, which may allow for the formation of agriculturally acceptable salts or agriculturally acceptable metal complexes.
  • Agriculturally acceptable salts and metal complexes include, without limitation, for example, ammonium salts, the salts of organic and inorganic acids, such as hydrochloric acid, sulfonic acid, ethanesulfonic acid, trifiuoroacetic acid, methylbenzenesulfonic acid, phosphoric acid, gluconic acid, pamoic acid, and other acid salts, and the alkali metal and alkaline earth metal complexes with, for example, sodium, potassium, lithium, magnesium, calcium, and other metals.
  • compositions containing an insecticidally effective amount of at least one compound of formula I with an insecticidally compatible carrier therefor Another aspect of the present invention relates to compositions containing an insecticidally effective amount of at least one compound of formula I, and an effective amount of at least one second compound, with an insecticidally compatible carrier therefor.
  • Another aspect of the present invention relates to methods of controlling insects by applying an insecticidally effective amount of a composition set forth above to a locus of crops such as, without limitation, cereals, cotton, vegetables, and fruits, or other areas where insects are present or are expected to be present.
  • the present invention also includes the use of the compounds and compositions set forth herein for control of non-agricultural insect species, for example, dry wood termites and subterranean termites; as well as for use as pharmaceutical agents and compositions thereof.
  • the present insecticidal compounds may be formulated as a granular of relatively large particle size (for example, 8/16 or 4/8 US Mesh), as water-soluble or water-dispersible granules, as powdery dusts, as wettable powders, as emulsifiable concentrates, as aqueous emulsions, as solutions, or as any of other known types of agriculturally-useful formulations, depending on the desired mode of application. It is to be understood that the amounts specified in this specification are intended to be approximate only, as if the word "about" were placed in front of the amounts specified.
  • insecticidal compositions may be applied either as water-diluted sprays, or dusts, or granules to the areas in which suppression of insects is desired. These formulations may contain as little as 0.1%, 0.2% or 0.5% to as much as 95% or more by weight of active ingredient.
  • Dusts are free flowing admixtures of the active ingredient with finely divided solids such as talc, natural clays, kieselguhr, flours such as walnut shell and cottonseed flours, and other organic and inorganic solids which act as dispersants and carriers for the toxicant; these finely divided solids have an average particle size of less than about 50 microns.
  • a typical dust formulation useful herein is one containing 1.0 part or less of the insecticidal compound and 99.0 parts of talc.
  • Wettable powders, also useful formulations for insecticides are in the form of finely divided particles that disperse readily in water or other dispersant.
  • wettable powder is ultimately applied to the locus where insect control is needed either as a dry dust or as an emulsion in water or other liquid.
  • Typical carriers for wettable powders include Fuller's earth, kaolin clays, silicas, and other highly absorbent, readily wet inorganic diluents. Wettable powders normally are prepared to contain about 5-80% of active ingredient, depending on the absorbency of the carrier, and usually also contain a small amount of a wetting, dispersing or emulsifying agent to facilitate dispersion.
  • a useful wettable powder formulation contains 80.0 parts of the insecticidal compound, 17.9 parts of Palmetto clay, and 1.0 part of sodium lignosulfonate and 0.3 part of sulfonated aliphatic polyester as wetting agents. Additional wetting agent and/or oil will frequently be added to a tank mix for to facilitate dispersion on the foliage of the plant.
  • ECs emulsif ⁇ able concentrates
  • ECs emulsif ⁇ able concentrates
  • ECs emulsif ⁇ able concentrates
  • these concentrates are dispersed in water or other liquid carrier and normally applied as a spray to the area to be treated.
  • the percentage by weight of the essential active ingredient may vary according to the manner in which the composition is to be applied, but in general comprises 0.5 to 95% of active ingredient by weight of the insecticidal composition.
  • Flowable formulations are similar to ECs, except that the active ingredient is suspended in a liquid carrier, generally water.
  • Flowables like ECs, may include a small amount of a surfactant, and will typically contain active ingredients in the range of 0.5 to 95%, frequently from 10 to 50%, by weight of the composition.
  • flowables may be diluted in water or other liquid vehicle, and are normally applied as a spray to the area to be treated.
  • Typical wetting, dispersing or emulsifying agents used in agricultural formulations include, but are not limited to, the alkyl and alkylaryl sulfonates and sulfates and their sodium salts; alkylaryl polyether alcohols; sulfated higher alcohols; polyethylene oxides; sulfonated animal and vegetable oils; sulfonated petroleum oils; fatty acid esters of polyhydric alcohols and the ethylene oxide addition products of such esters; and the addition product of long-chain mercaptans and ethylene oxide.
  • Many other types of useful surface-active agents are available in commerce. Surface-active agents, when used, normally comprise 1 to 15% by weight of the composition.
  • compositions include suspensions of the active ingredient in a relatively non-volatile solvent such as water, corn oil, kerosene, propylene glycol, or other suitable solvents.
  • Still other useful formulations for insecticidal applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene, or other organic solvents.
  • Granular formulations, wherein the toxicant is carried on relative coarse particles, are of particular utility for aerial distribution or for penetration of cover crop canopy.
  • Pressurized sprays, typically aerosols wherein the active ingredient is dispersed in finely divided form as a result of vaporization of a low- boiling dispersant solvent carrier may also be used.
  • Water-soluble or water- dispersible granules are free flowing, non-dusty, and readily water-soluble or water- miscible.
  • the granular formulations, emulsifiable concentrates, flowable concentrates, aqueous emulsions, solutions, etc. may be diluted with water to give a concentration of active ingredient in the range of say 0.1% or 0.2% to 1.5% or 2%.
  • the active insecticidal compounds of this invention may be formulated and/or applied with one or more second compounds.
  • Such combinations may provide certain advantages, such as, without limitation, exhibiting synergistic effects for greater control of insect pests, reducing rates of application of insecticide thereby minimizing any impact to the environment and to worker safety, controlling a broader spectrum of insect pests, safening of crop plants to phytotoxicity, and improving tolerance by non-pest species, such as mammals and fish.
  • Second compounds include, without limitation, other pesticides, plant growth regulators, fertilizers, soil conditioners, or other agricultural chemicals.
  • an effective amount and concentration of the active compound is of course employed; the amount may vary in the range of, e.g. about 0.001 to about 3 kg/ha, preferably about 0.03 to about 1 kg/ha.
  • higher application rates e.g., four times the rates mentioned above may be employed.
  • the herbicides include, without limitation, for example: N- (phosphonomethyl)glycines such as glyphosate; aryloxyalkanoic acids such as 2,4- D, MCPA, and MCPP; ureas such as isoproturon; imidazolinones such as imazapyr, imazamethabenz, imazethapyr, and imazaquin; diphenyl ethers such as acifluorfen, bifenox, and fomasafen; hydroxybenzonitriles such as ioxynil and bromoxynil; sulfonylureas such as chlorimuron, achlorsulfuron, bensulfuron, pyrazosulfuron, thifensulfuron, and triasulfuron; 2-(4-aryloxymethyl)glycines such as glyphosate; aryloxyalkanoic acids such as 2,4- D, MCPA, and MCPP;
  • the other insecticides include, for example: organophosphate insecticides, such as chlorpyrifos, diazinon, dimethoate, malathion, parathion- methyl, and terbufos; pyrethroid insecticides, such as fenvalerate, deltamethrin, fenpropathrin, cyfluthrin, flucythrinate, permethrin, ⁇ / ⁇ -cypermethrin, beta- cypermethrin, zet ⁇ -cypermethrin, bifenthrin, cypermethrin, resolved cyhalothrin, etofenprox, esfenvalerate, tralomethrin, tefluthrin, cycloprothrin, bet
  • organophosphate insecticides such as chlorpyrifos, diazinon, dimethoate, malathion, parathion- methyl,
  • the fungicides include, for example: benzimidazole fungicides, such as benomyl, carbendazim, thiabendazole, and thiophanate-methyl; 1,2,4-triazole fungicides, such as epoxyconazole, cyproconazole, flusilazole, flutriafol, propiconazole, tebuconazole, triadimefon, and triadimenol; substituted anilide fungicides, such as metalaxyl, oxadixyl, procymidone, and vinclozolin; organophosphoras fungicides, such as fosetyl, iprobenfos, pyrazophos, edifenphos, and tolclofos-methyl; morpholine
  • the active insecticidal compounds of the present invention are used in combination with one or more of second compounds, e.g., with other pesticides such as nematicides
  • the nematicides include, for example: carbofuran, carbosulfan, turbufos, aldecarb, ethoprop, fenamphos, oxamyl, isazofos, cadusafos, and other nematicides.
  • the plant growth regulators include, for example: maleic hydrazide, chlormequat, ethephon, gibberellin, mepiquat, thidiazon, inabenf ⁇ de, triaphenthenol, paclobutrazol, unaconazol, DCPA, prohexadione, trinexapac-ethyl, and other plant growth regulators.
  • Soil conditioners are materials which, when added to the soil, promote a variety of benefits for the efficacious growth of plants.
  • Soil conditioners are used to reduce soil compaction, promote and increase effectiveness of drainage, improve soil permeability, promote optimum plant nutrient content in the soil, and promote better pesticide and fertilizer incorporation.
  • the soil conditioners include organic matter, such as humus, which promotes retention of cation plant nutrients in the soil; mixtures of cation nutrients, such as calcium, magnesium, potash, sodium, and hydrogen complexes; or microorganism compositions which promote conditions in the soil favorable to plant growth.
  • microorganism compositions include, for example, bacillus, pseudomonas, azotobacter, azospirillum, rhizobium, and soil-borne cyanobacteria.
  • Fertilizers are plant food supplements, which commonly contain nitrogen, phosphorus, and potassium.
  • the fertilizers include nitrogen fertilizers, such as ammonium sulfate, ammonium nitrate, and bone meal; phosphate fertilizers, such as superphosphate, triple superphosphate, ammonium sulfate, and dianimonium sulfate; and potassium fertilizers, such as muriate of potash, potassium sulfate, and potassium nitrate, and other fertilizers.
  • nitrogen fertilizers such as ammonium sulfate, ammonium nitrate, and bone meal
  • phosphate fertilizers such as superphosphate, triple superphosphate, ammonium sulfate, and dianimonium sulfate
  • potassium fertilizers such as muriate of potash, potassium sulfate, and potassium nitrate, and other fertilizers.
  • alkyl and “alkoxy”, used alone or as part of a larger moiety, includes straight or branched chains of at least one or two carbon atoms, as appropriate to the substituent, and preferably up to 12 carbon atoms, more preferably up to ten carbon atoms, most preferably up to seven carbon atoms.
  • haloalkyl and haloalkoxy alone or as part of a larger moiety, include straight or branched chain alkyls of 1 to 14 carbon atoms, preferably lower straight or branched chain alkyls of 1 to 6 carbon atoms, wherein one or more hydrogen atoms have been replaced with halogen atoms, as, for example, trifluoromethyl or 2,2,2-trifluoroethoxy, respectively.
  • alkenyl and “alkynyl” used alone or as part of a larger moiety includes straight or branched chains of at least two carbon atoms containing at least one carbon-carbon double bond or triple bond, and preferably up to 12 carbon atoms, more preferably up to ten carbon atoms, most preferably up to seven carbon atoms.
  • heterocyclic refers to a non-aromatic ring structure of four to eight atoms consisting of carbon and nitrogen, and may include oxygen or sulfur.
  • Five member rings include, without limitation, for example, pyrrolidine.
  • Six member rings include, without limitation, for example, piperazine, piperidine, morpholine and thiomorpholine.
  • aryl refers to an aromatic ring structure, including fused rings, having four to ten carbon atoms, for example, phenyl or naphthyl.
  • heteroaryl and heterocyclyl refer to an aromatic ring structure, including fused rings, in which at least one of the atoms is other than carbon, for example, without limitation, sulfur, oxygen, or nitrogen.
  • polycyclyl refers to a non-aromatic fused ring structure.
  • Ammonio refers to compounds of nitrogen that may be considered derived from ammonia and includes primary, secondary and tertiary amines wherein one or more of the hydrogen atoms is replaced with alkyl groups.
  • GC analysis refers to gas chromatographic analysis of, for example, a chemical reaction mixture.
  • DMF refers to N,N-dimethylformamide.
  • THF tetrahydrofuran.
  • TEA triethylamine.
  • ambient temperature or “room temperature” often abbreviated as "RT”, for example, in reference to a chemical reaction mixture temperature, refers to a temperature in the range of 20 0 C to 30 0 C.
  • insecticidal or "acaricidal”
  • insecticide or “acaricide” refers to a compound of the present invention, either alone or in admixture with at least one of a second compound, or with at least one compatible carrier, which causes the destruction or the inhibition of action of insects or acarids.
  • Cyclohexylamine 2 (5.7 mL, 50 mmol) was added to dichloroquinazoline 1 (5.0 g, 25 mmol) dissolved in 100 mL of tetrahydrofuran at 0 0 C. The mixture was stirred at ambient temperature under a nitrogen atmosphere for about 18 hours. The resulting solids were filtered off and washed with ethyl ether. The filtrate was evaporated to give 7.5 g of quinazoline 3 in tetrahydrofuran. This intermediate 3 was used in the next reaction without further purification.
  • the test was established as described above using sub-multiples of the standard 50 millimolar DMSO solution of candidate insecticide.
  • the standard 50 millimolar solution was diluted by the robot with DMSO to give 5, 0.5, 0.05, 0.005, 0.0005 millimolar, or more dilute solutions of the candidate insecticide.
  • each well of the test plate was placed one second instar tobacco budworm larvea, each weighing approximately five milligrams. After the larvae were placed in each well, the plate was sealed with clear polyfilm adhesive tape. The tape over each well was perforated to ensure an adequate air supply. The plates were then held in a growth chamber at 25 0 C and 60% relative humidity for five days (light 14 hours/day).
  • insecticidal activity for each rate of application of compound was assessed as percent inhibition of insect weight relative to the weight of insects from untreated controls, and percent mortality when compared to the total number of insects infested.

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  • Organic Chemistry (AREA)
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  • Health & Medical Sciences (AREA)
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Abstract

La présente invention a trait à certains nouveaux composés de 2,4-diaminoquinazoline, à des dérivés associés et à leurs sels acceptables en agriculture qui ont présenté une activité pesticide inattendue. Ces composés sont de formule (I), dans laquelle: R, R2, R4, R5 et A sont tels que définis dans la description. L'invention a également trait à des compositions comportant une quantité à efficacité insecticide d'au moins un composé de formule (I), et éventuellement, une quantité efficace d'au moins un deuxième composé; ainsi qu'à des procédés de lutte contre les insectes comprenant l'application desdits composés à un site où des insectes sont présents ou sont susceptibles d'être présents.
PCT/US2006/011218 2005-03-28 2006-03-28 2,4-diaminoquinazolines insecticides et derives associes Ceased WO2006105056A2 (fr)

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WO2009084695A1 (fr) * 2007-12-28 2009-07-09 Carna Biosciences Inc. Dérivé de 2-aminoquinazoline
WO2009143058A1 (fr) * 2008-05-22 2009-11-26 Allergan, Inc. Composés bicycliques ayant une activité sur le récepteur cxcr4
WO2011140527A3 (fr) * 2010-05-07 2012-03-29 California Institute Of Technology And The University Of Kansas Méthodes et compositions pour l'inhibition de l'atpase transitionnelle du réticulum endoplasmique
JP2014500235A (ja) * 2010-09-29 2014-01-09 インターベツト・インターナシヨナル・ベー・ベー Ｎ−ヘテロアリール化合物
US20160024116A1 (en) * 2005-12-15 2016-01-28 Rigel Pharmaceuticals, Inc. Kinase Inhibitors And Their Uses
CN105367555A (zh) * 2014-08-07 2016-03-02 广东东阳光药业有限公司 取代的杂芳基化合物及其组合物和用途
CN106413715A (zh) * 2014-04-22 2017-02-15 林伯士艾瑞斯公司 Irak抑制剂和其用途
CN107531725A (zh) * 2015-08-13 2018-01-02 北京韩美药品有限公司 Irak4抑制剂及其应用
WO2018233648A1 (fr) * 2017-06-21 2018-12-27 南京明德新药研发股份有限公司 Dérivé d'isothiazolo[4,3-d]pyrimidine-5,7-diamine utilisé en tant qu'agoniste de tlr8
JP2019524790A (ja) * 2016-08-09 2019-09-05 ホンユン バイオテック カンパニー リミテッド チエノピリミジン系化合物、その製造方法、医薬組成物およびその応用
CN111423384A (zh) * 2019-07-04 2020-07-17 沈阳药科大学 2-氨基嘧啶类化合物及其用途
US11084807B2 (en) 2016-08-18 2021-08-10 Vidac Pharama Ltd. Piperazine derivatives, pharmaceutical compositions and methods of use thereof
WO2021155426A1 (fr) * 2020-02-04 2021-08-12 TroBio Therapeutics Pty Ltd Composés de quinazoline et leur utilisation dans le traitement du cancer

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IL88507A (en) * 1987-12-03 1993-02-21 Smithkline Beckman Intercredit 2,4-diaminoquinazolines, process for their preparation and pharmaceutical compositions comprising them
GB8910722D0 (en) * 1989-05-10 1989-06-28 Smithkline Beckman Intercredit Compounds
WO1997020822A1 (fr) * 1995-12-01 1997-06-12 Novartis Ag Quinazolin-2,4-diazirines en tant qu'antagoniste du recepteur du neuropeptide y
US6339089B2 (en) * 1997-08-13 2002-01-15 Fujirebio Inc. Pyrimidine nucleus-containing compound and a medicament containing the same for a blood oxygen partial pressure amelioration, and a method for preparing the same

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US9834568B2 (en) * 2005-12-15 2017-12-05 Rigel Pharmaceuticals, Inc. Kinase inhibitors and their uses
WO2009084695A1 (fr) * 2007-12-28 2009-07-09 Carna Biosciences Inc. Dérivé de 2-aminoquinazoline
WO2009143058A1 (fr) * 2008-05-22 2009-11-26 Allergan, Inc. Composés bicycliques ayant une activité sur le récepteur cxcr4
CN102105463A (zh) * 2008-05-22 2011-06-22 阿勒根公司 对cxcr4受体有活性的二环化合物
WO2011140527A3 (fr) * 2010-05-07 2012-03-29 California Institute Of Technology And The University Of Kansas Méthodes et compositions pour l'inhibition de l'atpase transitionnelle du réticulum endoplasmique
US8865708B2 (en) 2010-05-07 2014-10-21 California Institute Of Technology Methods and compositions for inhibition of the transitional endoplasmic reticulum ATPase
JP2014500235A (ja) * 2010-09-29 2014-01-09 インターベツト・インターナシヨナル・ベー・ベー Ｎ−ヘテロアリール化合物
CN106413715A (zh) * 2014-04-22 2017-02-15 林伯士艾瑞斯公司 Irak抑制剂和其用途
EP3134091A4 (fr) * 2014-04-22 2017-08-30 Nimbus Iris, Inc. Inhibiteurs d'irak et leurs utilisation
CN105367555A (zh) * 2014-08-07 2016-03-02 广东东阳光药业有限公司 取代的杂芳基化合物及其组合物和用途
CN105367555B (zh) * 2014-08-07 2019-06-25 广东东阳光药业有限公司 取代的杂芳基化合物及其组合物和用途
JP2018523672A (ja) * 2015-08-13 2018-08-23 北京韓美薬品有限公司 Ｉｒａｋ４阻害剤、及びその応用
EP3336091A4 (fr) * 2015-08-13 2019-01-23 Beijing Hanmi Pharmaceutical Co., Ltd. Inhibiteur d'irak4 et son utilisation
CN107531725A (zh) * 2015-08-13 2018-01-02 北京韩美药品有限公司 Irak4抑制剂及其应用
US10988482B2 (en) 2015-08-13 2021-04-27 Beijing Hanmi Pharmaceutical Co., Ltd. IRAK4 inhibitor and use thereof
JP2019524790A (ja) * 2016-08-09 2019-09-05 ホンユン バイオテック カンパニー リミテッド チエノピリミジン系化合物、その製造方法、医薬組成物およびその応用
US11078213B2 (en) 2016-08-09 2021-08-03 Hongyun Biotech Co., Ltd. Thienopyrimidine compound, preparation method thereof, pharmaceutical composition and application thereof
US11084807B2 (en) 2016-08-18 2021-08-10 Vidac Pharama Ltd. Piperazine derivatives, pharmaceutical compositions and methods of use thereof
US12162868B2 (en) 2016-08-18 2024-12-10 Vidac Pharma Ltd.. Piperazine derivatives, pharmaceutical compositions and methods of use thereof
WO2018233648A1 (fr) * 2017-06-21 2018-12-27 南京明德新药研发股份有限公司 Dérivé d'isothiazolo[4,3-d]pyrimidine-5,7-diamine utilisé en tant qu'agoniste de tlr8
CN111423384A (zh) * 2019-07-04 2020-07-17 沈阳药科大学 2-氨基嘧啶类化合物及其用途
CN111423384B (zh) * 2019-07-04 2021-10-15 沈阳药科大学 2-氨基嘧啶类化合物及其用途
JP2022538493A (ja) * 2019-07-04 2022-09-02 沈陽薬科大学 ２－アミノピリミジン化合物及びその使用
WO2021155426A1 (fr) * 2020-02-04 2021-08-12 TroBio Therapeutics Pty Ltd Composés de quinazoline et leur utilisation dans le traitement du cancer

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