WO1997049697A1 - Pyridylaminopyrimidines fongicides - Google Patents

Pyridylaminopyrimidines fongicides Download PDF

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Publication number
WO1997049697A1
WO1997049697A1 PCT/GB1997/001438 GB9701438W WO9749697A1 WO 1997049697 A1 WO1997049697 A1 WO 1997049697A1 GB 9701438 W GB9701438 W GB 9701438W WO 9749697 A1 WO9749697 A1 WO 9749697A1
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WIPO (PCT)
Prior art keywords
methyl
fluoro
chloro
alkyl
halo
Prior art date
Application number
PCT/GB1997/001438
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English (en)
Inventor
Patrick Jelf Crowley
William Guy Whittingham
James John Eshelby
John Williams
Original Assignee
Zeneca Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GBGB9613080.2A external-priority patent/GB9613080D0/en
Priority claimed from GBGB9703495.3A external-priority patent/GB9703495D0/en
Application filed by Zeneca Limited filed Critical Zeneca Limited
Priority to AU29678/97A priority Critical patent/AU2967897A/en
Publication of WO1997049697A1 publication Critical patent/WO1997049697A1/fr

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Classifications

    • 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
    • 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

Definitions

  • the present invention relates to novel pyridylaminopyrimidines, to process for preparing them, to fungicidal compositions containing them and to methods of using them to combat fungi, especially fungal infections of plants.
  • R 1 is C M alkyl, halo(C ⁇ -4 )alkyl, C 3 . 6 cycloalkyi, C M alkoxy or halo(C M )alkoxy
  • R 2 is H, C ⁇ -4 alkyl, d. 4 alkylcarbonyl or C ⁇ - 4 alkoxycarbonyl
  • R 3 and R 5 are independently H, halo or methyl
  • R 4 and R 6 are independently H, halo, hydroxy, C M alkyl, halo(C ⁇ . 4 )alkyl, 0. 4 alkoxy, halo(C ⁇ -4 )alkoxy, cyano or hydrazino
  • R 7 is C M alkyl or C 1-4 alkoxy.
  • halo includes fluoro, chloro and bromo. Preferred values are fluoro and chloro.
  • Alkyl and the alkyl moieties of alkoxy, alkylcarbonyl and alkoxycarbonyl contain from 1 to 4 carbon atoms and may be in the form of straight or branched chains. Examples are methyl, ethyl, wo-propyl and tert-bulyl. A preferred value is methyl.
  • Cycloalkyi contains from 3 to 6 carbon atoms. It is preferably cyclopropyl but also includes cyclobutyl, cyclopentyl and cyclohexyl. Halo(C ⁇ .
  • Halo(C].4)alkoxy is preferably halomethoxy and, especially, trifluoromethoxy.
  • the invention provides a compound of formula (I) wherein R 1 is methyl, cyclopropyl, methoxy or trifluoromethyl, R 2 is H, methyl or acetyl, R 3 and R 5 are independently H, fluoro, chloro or methyl, R 4 and R 6 are independently H, fluoro, chloro, hydroxy, methyl, trifluoromethyl or methoxy and R 7 is methyl or methoxy.
  • R 3 and R 5 are both hydrogen. It is also generally preferred that R 1 is methyl or cyclopropyl and R 7 is methyl.
  • the invention provides a compound of formula (I) wherein R 1 is methyl or cyclopropyl, R 2 is H, methyl or acetyl, R 3 and R 5 are both H, R 4 and R 6 are independently H, fluoro, chloro, hydroxy, methyl, trifluoromethyl or methoxy and R 7 is methyl.
  • the invention provides a compound of formula (I) wherein R' is methyl or cyclopropyl, R 2 is H, methyl or acetyl, R 3 and R 5 are both H, R 4 is H, fluoro or chloro, R 6 is H, fluoro, chloro, hydroxy, methyl, trifluoromethyl or methoxy and R 7 is methyl.
  • the invention provides a compound of the general formula (la) :
  • R 2 is H or methyl
  • R 4 is fluoro or chloro
  • R 6 is fluoro, chloro, hydroxy or methoxy.
  • the invention provides a compound of formula (la) wherein R * is H or methyl and R 4 and R 6 are either both fluoro or both chloro.
  • R 2 is hydrogen.
  • the invention provides a compound of formula (I) wherein R 2 is H and R 4 and R 6 are both fluoro or both chloro.
  • the compound (I) can be prepared by reacting a 2-methanesulphonylpyrimidine (LI) with a 4- aminopyridine (DT) in a suitable solvent, for example, a polar aprotic solvent such as dimethyl acetamide, using a base such as sodium hydride or potassium carbonate, at a suitable temperature for example between 0°C and 100°C, as shown in Scheme 1.
  • a suitable solvent for example, a polar aprotic solvent such as dimethyl acetamide
  • a base such as sodium hydride or potassium carbonate
  • 2-Methanesulphonylpyrimidine (LI) may be prepared by oxidising a 2-methylthiopyrimidine (IV), for example, with potassium permanganate.
  • the 2-methylthiopyrimidines (IV) are readily available commercially or are well known in the literature.
  • the butanedione (V) may be prepared, for example, by reacting a 2,4-butanedione (V) with 2-methyl-2-thiopseudourea in a suitable solvent such as N.N-dimethylformamide.
  • the butanedione (V) may be prepared by reacting a ketone (VI) with an ethyl alkanoate (XIV) in the presence of a base such as sodium ethoxide.
  • Alternatively compounds (I) may be made by the reaction of 2-aminopyrimidines (VII) with 4-fluoropyridines (VLII), in a suitable solvent, for example, a polar aprotic solvent such as dimethyl acetamide, or an ether such as tetrahydrofuran (THF), using a base such as sodium hydride, at a temperature between 0°C and 150°C.
  • a suitable solvent for example, a polar aprotic solvent such as dimethyl acetamide, or an ether such as tetrahydrofuran (THF)
  • THF tetrahydrofuran
  • VLLI 4-Fluoropyridines
  • IX reducing compounds
  • X and Y can be hydrogen, chlorine or bromine, with at least one of X and Y not being hydrogen.
  • the reduction can be carried out for example by catalytic hydrogenation using hydrogen gas over a suitable metal catalyst such as palladium on carbon, in a suitable solvent such as acetic acid in the presence of a base such as sodium acetate, at a suitable pressure, for example between atmospheric pressure and 20 bar.
  • suitable metal catalyst such as palladium on carbon
  • a suitable solvent such as acetic acid
  • a base such as sodium acetate
  • Aminopyridines are either available commercially, or can be made, for example, by the reduction of the corresponding nitropyridine N-oxides (X), as shown in Scheme 2. The reduction can be carried out, for example, by a metal such as iron or tin, in a suitable acid such as acetic acid.
  • the nitropyridine N-oxides ( X) can be made by nitration of the pyridine N-oxides(XI), using concentrated nitric acid and concentrated sulphuric acid at a suitable temperature, for example between 0°C and 50°C.
  • the pyridine N-oxides (XI) are available commercially or can be made by oxidation of pyridines (XLI) with a peracid, for example, that generated by the addition of hydrogen peroxide to acetic acid.
  • aminopyridines can be made by the reduction of compounds (XIII), where X and Y can be hydrogen, chlorine or bromine, with at least one of X and Y not being hydrogen.
  • the reduction can be carried out, for example, by catalytic hydrogenation using hydrogen gas over a suitable metal catalyst such as palladium on carbon, in a suitable solvent such as acetic acid in the presence of a base such as sodium acetate, at a suitable pressure, for example between atmospheric pressure and 20 bar, and at a suitable temperature, between 0°C and 100°C.
  • a suitable metal catalyst such as palladium on carbon
  • a suitable solvent such as acetic acid
  • a base such as sodium acetate
  • Compounds (XLTI) are well known in the literature, or are available commercially.
  • Compounds of formula (I) where R 2 is methyl can be prepared by the yV-methylation of compounds of formula (I), where R 2 is hydrogen using a methylating agent such as dimethyl sulphate using well known
  • Compounds of formula (I) where R 2 is acetyl can be made by reacting compounds of formula (I) where R 2 is hydrogen, with an acetylating agent such as acetyl chloride in the presence of a base, for example, triethylamine.
  • an acetylating agent such as acetyl chloride in the presence of a base, for example, triethylamine.
  • Compounds of formula (XVI) as shown in Scheme 3 can be made by reducing hydrazine compounds of formula (XV) with copper sulphate, in a suitable solvent such as water, containing an acid such as acetic acid.
  • Compounds of formula (XV) can be made by reacting compounds of formula (1), where R 6 is a halogen, with aqueous hydrazine hydrate in a suitable solvent such as ethanol, to give compounds of formula (XV).
  • the compounds of formula (I) are active fungicides and may be used to control one or more of the following pathogens: Pyricularia oryzae on rice and wheat and other Pyricularia spp. on other hosts; Puccinia recondita, Puccinia striiformis and other rusts on wheat, Puccinia hordei, Puccinia striiformis and other rusts on barley, and rusts on other hosts e.g.
  • post-harvest diseases particularly of fruit e.g. Pencillium digitatum and P. italicum and Trichoderma viride on oranges, Colletotrichum musae and Gloeosporium musarum on bananas and Botrytis cinerea on grapes
  • other pathogens on vines notably Eu ⁇ ypa lata, Guignardia bidwellii, Phellinus igniarus,
  • BYMV barley yellow mosaic virus
  • some of the compounds may be useful as seed dressings against pathogens including Fusarium spp., Septoria spp., Tilletia spp., (e.g. bunt, a seed-borne disease of wheat), Ustilago spp. and Helminthosporium spp. on cereals, Rhizoctonia solani on cotton and Pyricularia oryzae on rice.
  • the compounds may move acropetally/locally in plant tissue.
  • the compounds may be volatile enough to be active in the vapour phase against fungi on the plant.
  • the invention therefore provides a method of combating fungi which comprises applying to a plant, to a seed of a plant or to the locus of the plant or seed a fungicidally effective amount of a compound as hereinbefore defined, or a composition containing the same.
  • the compounds may be used directly for agricultural purposes but are more conveniently formulated into compositions using a carrier or diluent.
  • the invention thus provides fungicidal compositions comprising a compound as hereinbefore defined and an acceptable carrier or diluent therefor. It is preferred that all compositions, both solid and liquid formulations, comprise 0.0001 to 95%, more preferably 1 to 85%, for example 1 to 25% or 25 to 60%, of a compound as hereinbefore defined.
  • the compounds of the invention When applied to the foliage of plants, the compounds of the invention are applied at rates of O.lg to 10kg, preferably lg to 8kg, more preferably lOg to 4kg, of active ingredient (invention compound) per hectare.
  • the compounds of the invention are used at rates of O.OOOlg (for example O.OOlg or 0.05g) to lOg, preferably 0.005g to 8g, more preferably 0.005g to 4g, of active ingredient (invention compound) per kilogram of seed.
  • O.OOOlg for example O.OOlg or 0.05g
  • the compounds can be applied in a number of ways. For example, they can be applied, formulated or unformulated, directly to the foliage of a plant, to seeds or to other medium in which plants are growing or are to be planted, or they can be sprayed on, dusted on or applied as a cream or paste formulation, or they can be applied as a vapour or as slow release granules. Application can be to any part of the plant including the foliage, stems, branches or roots, or to soil surrounding the roots, or to the seed before it is planted, or to the soil generally, to paddy water or to hydroponic culture systems.
  • the invention compounds may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial i ⁇ igation systems.
  • plant as used herein includes seedlings, bushes and trees. Furthermore, the fungicidal method of the invention includes preventative, protectant, prophylactic, systemic, curative and eradicant treatments.
  • the compounds are preferably used for agricultural and horticultural purposes in the form of a composition.
  • the type of composition used in any instance will depend upon the particular purpose envisaged.
  • compositions may be in the form of dustable powders or granules comprising the active ingredient (invention compound) and a solid diluent or carrier, for example, fillers such as kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, fuller's earth, gypsum, diatomaceous earth and china clay.
  • a solid diluent or carrier for example, fillers such as kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, fuller's earth, gypsum, diatomaceous earth and china clay.
  • Such granules can be preformed granules suitable for application to the soil without further treatment.
  • These granules can be made either by impregnating pellets of filler with the active ingredient or by pelleting a mixture of the active ingredient and powdered filler.
  • compositions for dressing seed may include an agent (for example, a mineral oil) for assisting the adhesion of the composition to the seed; alternatively the active ingredient can be formulated for seed dressing purposes using an organic solvent (for example, N-methylpyrrolidone, propylene glycol or N,N-dimethylforrnamide).
  • the compositions may also be in the form of water dispersible powders or water dispersible granules comprising wetting or dispersing agents to facilitate the dispersion in liquids.
  • the powders and granules may also contain fillers and suspending agents.
  • compositions may also be in the form of soluble powders or granules, or in the form of solutions in polar solvents.
  • Soluble powders may be prepared by mixing the active ingredient with a water-soluble salt such as sodium bicarbonate, sodium carbonate, magnesium sulphate or a polysaccharide, and a wetting or dispersing agent to improve water dispersibility/solubility. The mixture may then be ground to a fine powder. Similar compositions may also be granulated to form water-soluble granules. Solutions may be prepared by dissolving the active ingredient in polar solvents such as ketones, alcohols and glycol ethers. These solutions may contain surface active agents to improve water dilution and prevent crystallisation in a spray tank.
  • polar solvents such as ketones, alcohols and glycol ethers.
  • Emulsifiable concentrates or emulsions may be prepared by dissolving the active ingredient in an organic solvent optionally containing a wetting or emulsifying agent and then adding the mixture to water which may also contain a wetting or emulsifying agent.
  • organic solvents are aromatic solvents such as alkylbenzenes and alkylnaphthalenes, ketones such as cyclohexanone and methylcyclohexanone, chlorinated hydrocarbons such as chlorobenzene and trichlorethane, and alcohols such as benzyl alcohol, furfuryl alcohol, butanol and glycol ethers.
  • Aqueous suspension concentrates of largely insoluble solids may be prepared by ball or bead milling with a dispersing agent with a suspending agent included to stop the solid settling.
  • compositions to be used as sprays may be in the form of aerosols wherein the formulation is held in a container under pressure of a suitable propellant.
  • the invention compounds can be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating in enclosed spaces a smoke containing the compounds.
  • the compounds may be used in micro-encapsulated form. They may also be formulated in biodegradable polymeric formulations to obtain a slow, controlled release of the active substance.
  • additives for improving the uptake, distribution, adhesive power and resistance to rain on treated surfaces the different compositions can be better adapted for various utilities.
  • Other additives may be included to improve the biological efficacy of the various formulations.
  • Such additives can be surface active materials to improve the wetting and retention on surfaces treated with the formulation and also the uptake and mobility of the active material, or additionally can include oil based spray additives, for example, certain mineral oil and natural plant oil (such as soya bean and rape seed oil) additives, or blends of them with other adjuvants.
  • the invention compounds can be used as mixtures with fertilisers (e.g. nitrogen-, potassium- or phosphorus-containing fertilisers).
  • compositions comprising only granules of fertiliser incorporating, for example coated with, a compound of formula (I) are preferred. Such granules suitably contain up to 25% by weight of the compound.
  • the invention therefore also provides a fertiliser composition comprising a fertiliser and the compound of general formula (I) or a salt or metal complex thereof.
  • Water dispersible powders, emulsifiable concentrates and suspension concentrates will normally contain surfactants, e.g. a wetting agent, dispersing agent, emulsifying agent or suspending agent. These agents can be cationic, anionic or non-ionic agents.
  • Suitable cationic agents are quaternary ammonium compounds, for example, cetyltrimethylammonium bromide.
  • Suitable anionic agents are soaps, salts of aliphatic monoesters of sulphuric acid (for example, sodium lauryl sulphate), and salts of sulphonated aromatic compounds (for example, sodium dodecylbenzenesulphonate, sodium, calcium or ammonium lignosulphonate, butylnaphthalene sulphonate, and a mixture of sodium diisopropyl- and triisopropylnaphthalene sulphonates).
  • Suitable non-ionic agents are the condensation products of ethylene oxide with fatty alcohols such as oleyl or cetyl alcohol, or with alkyl phenols such as octyl- or nonylphenol and octylcresol.
  • Other non-ionic agents are the partial esters derived from long chain fatty acids and hexitol anhydrides, alkyl glucosides, polysaccharides and the lecithins and the condensation products of the said partial esters with ethylene oxide.
  • Suitable suspending agents are hydrophihc colloids (for example, polyvinylpyrrolidone and sodium carboxymethylcellulose), and swelling clays such as bentonite or attapulgite.
  • compositions for use as aqueous dispersions or emulsions are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being diluted with water before use.
  • These concentrates should preferably be able to withstand storage for prolonged periods and after such storage be capable of dilution with water in order to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment.
  • the concentrates may conveniently contain up to 95%, suitably 1-85%, for example 1-25% or 25-60%, by weight of the active ingredient.
  • compositions of this invention may contain other compounds having biological activity, e.g. compounds having similar or complementary fungicidal activity or which possess plant growth regulating, herbicidal or insecticidal activity.
  • the resulting composition can have a broader spectrum of activity or a greater level of intrinsic activity than the compound of general formula (I) alone. Further the other fungicide can have a synergistic effect on the fungicidal activity of the compound of general formula (I).
  • fungicidal compounds which may be included in the composition of the invention are (Ej-N-methyl-2-(2-phenoxyphenyl)-2- methoxyiminoacetamide, (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy- iminoacetamide, (RS)-l -aminopropylphosphonic acid, ( ⁇ S>4-(4-chlorophenyl)-
  • This Example illustrates the preparation of 2-(2,6-difluoro-4-pyridylamino)-4- cyclopropyl-6-methylpyrimidine (compound 1 of Table 1).
  • EXAMPLE 2 This Example illustrates the preparation of 2-(2,6-difluoro-4-pyridyl-(N-methyl)- amino)-4-cyclopropyl-6-methylpyrimidine (compound 3 of Table 1), 2-(2-fluoro-4- methoxypyrid-4-yl-(N-methyl)-amino)-4-cyclopropyl-6-methylpyrimidine (compound 6 of Table 1) and 2-(2-fluoro-4-hydroxypyrid-4-yl-(N-methyl)-amino)-4-cyclopropyl-6- methylpyrimidine (compound 8 of Table 1).
  • 2-Methanesulphonyl-4,6-dimethylpyrimidine (1.9 g), 4-amino-2,6-difluoropyridine (1.3 g) and anhydrous potassium carbonate (2.75 g) were heated at 155°C in dry DMF for 2.5 hours, and then cooled to room temperature. The reaction mixture was quenched with aqueous NH 4 C1, and extracted three times with ethyl acetate. The organic extracts were dried over magnesium sulphate, and evaporated to yield a pale brown solid.
  • This Example illustrates the preparation of 4-amino-3-fluoropyridine (an intermediate used in the preparation of compound 15 of Table 1).
  • 3-FIuoropyridine-N-oxide (8.60 g) was added portionwise to concentrated sulphuric acid (18 ml) with stirring at 10°C. Concentrated nitric acid (18 ml) was then added dropwise to the stirring solution , and the temperature rose to approximately 30-35°C. The addition rate was adjusted to control the temperature, the reaction then stirred at room temperature for 30 minutes, and then refluxed for 6 hours. It was then cooled, neutralised with solid sodium carbonate, and extracted with dichloromethane, and the organic extract dried over magnesium sulphate. The solvent was evaporated to give a sludge, which was triturated to yield the required product as a yellow solid (6.1 g).
  • EXAMPLE 7 The compounds were tested against a variety of foliar fungal diseases of plants. The technique employed was as follows.
  • the plants were grown in John Lanes Potting Compost (No 1 or 2) in 4 cm diameter minipots.
  • the test compounds were formulated either by bead milling with aqueous Dispersol T or as a solution in acetone or acetone/ethanol which was diluted to the required concentration immediately before use.
  • the formulations (100 ppm active ingredient) were sprayed on to the foliage of the plants to maximum retention. Tween 20 was added to give a final concentration of 0.1% by volume when the sprays were applied to cereals.
  • This calculated POCO value is then rounded to the nearest of the values in the 9-point assessment scale shown above. In this particular example, the POCO value would be rounded to 30. If the calculated POCO falls exactly mid-way between two of the points, it is rounded to the lower of the two values. The results are shown in Table 3.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Composé fongicide représenté par la formule (I), dans laquelle R1 est C¿1-4? alkyle, halo(C1-4)alkyle, C3-6 cycloalkyle, C1-4 alcoxy ou halo(C1-4)alcoxy, R?2¿ est H, C¿1-4? alkyle, C1-4 alkylcarbonyle ou C1-4 alcoxycarbonyle, R?3 et R5¿ sont indépendamment H, halo ou méthyle, R4 et R6 sont indépendamment H, halo, hydroxy, C¿1-4? alkyle, halo(C1-4)alkyle, C1-4 alcoxy, halo(C1-4)alcoxy, cyano ou hydrazino, et R?7¿ est C¿1-4? alkyle ou C1-4 alcoxy.
PCT/GB1997/001438 1996-06-21 1997-05-27 Pyridylaminopyrimidines fongicides WO1997049697A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU29678/97A AU2967897A (en) 1996-06-21 1997-05-27 Pyridylaminopyrimidines as fungicides

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GBGB9613080.2A GB9613080D0 (en) 1996-06-21 1996-06-21 Fungicides
GB9613080.2 1996-06-21
GB9703495.3 1997-02-20
GBGB9703495.3A GB9703495D0 (en) 1997-02-20 1997-02-20 Fungicides

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CO (1) CO4790134A1 (fr)
WO (1) WO1997049697A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003535109A (ja) * 2000-06-08 2003-11-25 シンジエンタ パーテイスィペイシヨンズ アクチエンゲゼルシヤフト Ｎ−フェニル−（４−ピリジル）−２−ピリミジンアミン誘導体
CN101863829B (zh) * 2009-04-16 2012-02-15 上海联友制药技术有限公司 一种3-氟-4-氨基吡啶的合成方法
CN103739557A (zh) * 2013-12-30 2014-04-23 黄河三角洲京博化工研究院有限公司 一种4,6-二甲基-2-甲磺酰基嘧啶的合成方法
CN108840791A (zh) * 2018-07-18 2018-11-20 陕西恒润化学工业有限公司 一种环丙酰基丙酮及其合成方法
CN112321497A (zh) * 2020-12-11 2021-02-05 南京正荣医药化学有限公司 一种4-氨基吡啶类化合物的制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE780547A (fr) * 1971-03-19 1972-09-11 Ici Ltd Derives de diazines et compositions pesticides
US3974276A (en) * 1971-03-19 1976-08-10 Imperial Chemical Industries Limited Certain diazines as plant pesticides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE780547A (fr) * 1971-03-19 1972-09-11 Ici Ltd Derives de diazines et compositions pesticides
US3974276A (en) * 1971-03-19 1976-08-10 Imperial Chemical Industries Limited Certain diazines as plant pesticides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
P. MASNER ET AL.: "Possible methionine biosynthesis inhibition by pyrimidineamine fungicides.", PESTICIDE SCIENCE, vol. 42, 1994, BARKING GB, pages 163 - 166, XP002038591 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003535109A (ja) * 2000-06-08 2003-11-25 シンジエンタ パーテイスィペイシヨンズ アクチエンゲゼルシヤフト Ｎ−フェニル−（４−ピリジル）−２−ピリミジンアミン誘導体
CN101863829B (zh) * 2009-04-16 2012-02-15 上海联友制药技术有限公司 一种3-氟-4-氨基吡啶的合成方法
CN103739557A (zh) * 2013-12-30 2014-04-23 黄河三角洲京博化工研究院有限公司 一种4,6-二甲基-2-甲磺酰基嘧啶的合成方法
CN103739557B (zh) * 2013-12-30 2015-10-21 黄河三角洲京博化工研究院有限公司 一种4,6-二甲基-2-甲磺酰基嘧啶的合成方法
CN108840791A (zh) * 2018-07-18 2018-11-20 陕西恒润化学工业有限公司 一种环丙酰基丙酮及其合成方法
CN112321497A (zh) * 2020-12-11 2021-02-05 南京正荣医药化学有限公司 一种4-氨基吡啶类化合物的制备方法

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AU2967897A (en) 1998-01-14

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