WO1997038995A1 - Derives fongicides d'oxazolidinediones - Google Patents
Derives fongicides d'oxazolidinediones Download PDFInfo
- Publication number
- WO1997038995A1 WO1997038995A1 PCT/GB1997/000822 GB9700822W WO9738995A1 WO 1997038995 A1 WO1997038995 A1 WO 1997038995A1 GB 9700822 W GB9700822 W GB 9700822W WO 9738995 A1 WO9738995 A1 WO 9738995A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- halo
- alkoxy
- optionally substituted
- aryl
- Prior art date
Links
- 0 *COc1ccc(C(*)(C(*2**)=O)OC2=O)cc1 Chemical compound *COc1ccc(C(*)(C(*2**)=O)OC2=O)cc1 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
Definitions
- the present invention relates to novel oxazolidinedione derivatives, to processes 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 a C-linked 6-membered heteroaromatic ring containing 2 or 3 nitrogen atoms and which is optionally N- or C-substituted with one or more of halo, hydroxy, oxo, C ⁇ -6 alkyl, C 3 . 6 cycloalkyl, halo(C ⁇ . 6 )alkyl, C ⁇ -4 alkoxy(C ⁇ . 6 )alkyl, aryl(C ⁇ -6 )alkyl, Ci. 6 alkoxy, halo(C ⁇ . 6 )alkoxy, C 2 . 4 alkenyloxy, d_ 6 alkylthio, C ⁇ -6 alkylcarbonyl, C ⁇ .
- 6 alkylcarbonylamino Ci.6 alkoxycarbonyl, arylcarbonyl, aryl, aryloxy, or heteroaryl, the aryl and heteroaryl substituents themselves being optionally substituted with one or more of halo, C ⁇ . 6 alkyl, halo(C ⁇ . 6 )alkyl, C
- R 2 is phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, thiadiazolyl, oxadiazolyl or tetrazolyl, any of which is optionally substituted with one or more of halo, C ⁇ -6 alkyl, halo(C[. 6 )alkyl, C
- alkyl moieties including the alkyl moieties of haloalkyl, alkoxy, alkylthio, alkylsulphonyl, etc., suitably contain from 1 to 6 , for example from 1 to 4, carbon atoms in the form of straight or branched chains. Examples are methyl, ethyl, n- and wo-propyl, n-, sec-, iso- and tert-butyl and n-hexyl.
- C 3 . 6 cycloalkyl includes cyclopropyl and cyclohexyl.
- Halo includes fluoro, chloro, bromo and iodo. Most commonly it is fluoro or chloro.
- Haloalkyl is typically trifluoromethyl and haloalkoxy is typically trifluoromethoxy.
- Aryl is usually phenyl but also includes naphthyl.
- Heteroaryl includes the residues of 6-membered heteroaromatic rings containing from 1 to 3 N atoms, eg pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or 1,3,5-triazinyl, and the residues of 5-membered heteroaromatic rings containing 1 to 3 heteroatoms selected from N, O and S, eg furyl, thienyl, pyrrolyl, thiazolyl, oxazolyl, isothiazolyl, isoxazolyl, pyrazolyl, imidazolyl, thiadiazolyl, oxadiazolyl or triazolyl.
- heteroaryl is pyridyl, thienyl, furyl, pyrrolyl, isoxazolyl or isothiazolyl.
- the 6-membered heteroaromatic ring R 1 is selected from pyrimidinyl, pyrazinyl, pyridazinyl and 1,2,4- and 1,3,5-triazinyl.
- R 1 is 2-pyrimidinyl, 4-pyrimidinyl, 5- pyrimidinyl, 2-pyrazinyl, 3 -pyridazinyl, or 2-( 1,3,5-triazinyl) optionally N- or C-substituted with one or more of the R 1 substituents listed above.
- R 1 is 2-pyrimidinyl optionally substituted with hydroxy, oxo, CM alkyl, C 3 . 6 cycloalkyl, halo(C
- the aryl or heteroaryl substituent of the 6-membered heteroaromatic ring R 1 may be any aryl or heteroaryl group defined above and may be optionally substituted with one or more of halo, CM alkyl, halo(C ⁇ . 4 )alkyl, C M alkoxy, halo(C ⁇ . 4 )alkoxy, C M alkoxy (C ⁇ . 4 )alkyl, nitro, amino, mono- or di(C M )alkylamino, cyano, C M alkoxycarbonyl or C
- the group R 2 is typically unsubstituted phenyl but may also be phenyl substituted with a bromine or iodine atom, with 1 to 5 chlorine or fluorine atoms, with 4 chlorine or fluorine atoms and a methyl or trifluoromethyl group or with 1 to 3 substituents selected from halo, CM alkyl, halo(C ⁇ . 4 )alkyl, C M alkoxy, halo(C ⁇ . 4 )alkoxy, C I-4 alkylthio, nitro, cyano, thiocyanato, C M alkylsulphonyl, halo(C ⁇ .
- R 2 is, for example, 2-, 3- or 4-pyridyl, 2-, 4- or 5-pyrimidinyl, 3-pyridazinyl, 3-thienyl, 3- or 5-pyrazolyl, 2-thiazolyl, 3-(l,2,4-triazolyl), 5- (1,2,3-thiadiazolyl) or 5-tetrazolyl, any of which is optionally substituted with 1 to 3 substituents selected from halo, C
- R 2 is, for example, 2-, 3- or 4-quinolinyl, 4-quinazolinyl, 1- phthalazinyl, 2-quinoxalinyl, 3-(l,2,4-benzotriazinyl), 2-benzoxazolyl or 2-benzothiazolyl, any of which is optionally substituted in its fused benzene ring with halo, C M alkyl, C M alkoxy or nitro and in its heterocyclic ring with halo, C M alkyl, halo(C
- the present invention is illustrated by the compounds of general formula (I) listed in
- Table 1 comprises 167 compounds of the general formula (I), wherein R' is 4-methyl- 6-hydroxypyrimidin-2-yl and R 2 has the value listed below.
- Table 2 comprises 167 compounds of the general formula (I), wherein R 1 is 4- methoxy-6-methylpyrimidin-2-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 3 comprises 167 compounds of the general formula (I), wherein R' is 4- allyloxy-6-methylpyrimidin-2-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 4 comprises 167 compounds of the general formula (I), wherein R 1 is 4,6- dimethoxypyrimidin-2-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 5 comprises 167 compounds of the general formula (I), wherein R 1 is 4,6- dimethylpyrimidin-2-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 6 comprises 167 compounds of the general formula (I), wherein R 1 is 1,4- dimethyl-6-oxopyrimidin-2-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 7 comprises 167 compounds of the general formula (I), wherein R' is 2- wopropyl-6-hydroxypyrimidin-4-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 8 comprises 167 compounds of the general formula (I), wherein R 1 is 2-(5- trifluoromethylpyrid-2-yl)-6-methylpyrimidin-4-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 9 comprises 167 compounds of the general formula (I), wherein R 1 is pyrimidin- 5-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 10 comprises 167 compounds ofthe general formula (I), wherein R 1 is 2- methylpyrimidin-5-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 11 comprises 167 compounds of the general formula (I), wherein R 1 is 2-t- butylpyrimidin-5-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 12 comprises 167 compounds ofthe general formula (I), wherein R 1 is 2- trifluoromethylpyrimidin-5-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 13 comprises 167 compounds of the general formula (I), wherein R 1 is 2- trifluoromethyl-4,6-dimethylpyrimidin-5-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 14 comprises 167 compounds of the general formula (I), wherein R 1 is 2,4- dimethoxypyrimidin-5-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 15 comprises 167 compounds of the general formula (I), wherein R 1 is pyridazin-3-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 16 comprises 167 compounds of the general formula (I), wherein R 1 is pyrazin- 2-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- Table 8 comprises 167 compounds of the general formula (I), wherein R 1 is 4,6- diphenyl-l,3,5-triazin-2-yl and R 2 has the value listed for the correspondingly numbered compound in Table 1.
- the compounds of the invention may be obtained in the form of mixtures of stereoisomers, including enantiomers, diastereomers and geometric isomers. Such mixtures may be separated into individual isomers by techniques well known in the art and this invention embraces the individual isomers and mixtures thereof in all proportions. It is to be expected that one isomer may be more fungicidally active than another.
- the compounds of formula (I) can be prepared by reacting a compound of formula (II):
- R 1 has the meaning given above and R is, for example, C M alkyl, suitably ethyl, with a carbonylating agent, suitably l.l'-carbonyldiimidazole, in a convenient water-immiscible solvent, such as dichloromethane, at an elevated temperature, for example the reflux temperature of dichloromethane (ca 41°C).
- a convenient water-immiscible solvent such as dichloromethane
- the product is conveniently isolated by pouring the reaction mixture into water and separating, or extracting with a solvent, the organic phase, which is washed, dried and evaporated.
- the product redissolved in the water-immiscible solvent, is reacted with a hydrazine of formula R 2 NHNH 2 in the presence of an acid catalyst, for example acetic acid, typically at ambient temperature.
- an acid catalyst for example acetic acid
- the reaction mixture may be poured into water and the organic phase extracted with a solvent or otherwise separated from the aqueous phase.
- the organic phase is washed, for example, successively with a dilute mineral acid, such as hydrochloric acid, an aqueous base, such as sodium bicarbonate, and brine before being dried and evaporated to give the desired product in crude form.
- the product can then be purified by the usual chromatographic techniques.
- Carbonylating agents such as l,l'-carbonyldiimidazole, are commercially available, as are many hydrazines of formula R 2 NHNH 2 . Hydrazines of formula R 2 NHNH 2 not commercially available may be prepared by methods well documented in the literature.
- R and R 1 have the meanings given above and X is halo, suitably chloro, in a convenient solvent, such as N,N-dimethylformamide, and in the presence of a base, such as potassium carbonate.
- a convenient solvent such as N,N-dimethylformamide
- a base such as potassium carbonate.
- the desired product may be isolated by pouring the reaction mixture into water, extracting the product with a solvent, for example ethyl acetate, and washing, drying and evaporating the organic extract.
- the product may be purified by the usual chromatographic techniques.
- the compound RXCH 2 X is either commercially available or can be prepared by methods well documented in the literature.
- Compounds of the formula (III) can be prepared by treating a compound of formula (III) can be prepared by treating a compound of formula (III)
- TBDMSO t-butyldimethylsiloxy and R has the meaning given above
- a solvent such as tetrahydrofuran
- tetrabutylammonium fluoride a solution of tetrabutylammonium fluoride
- Compounds of formula (IV) can be prepared by reacting the Grignard reagent formed from magnesium, iodine and 4- bromo-l-(/-butyldimethylsiloxy)benzene with sodium pyruvate in tetrahydrofuran and treating the propionic acid so formed with ethyl iodide in N,N-dimethyl formamide in the presence of diisopropylethylamine.
- 4-Bromo- 1 -(t-butyldimethylsiloxy)benzene may be obtained by reacting 4-bromophenol with t-butyl-dimethylsilylchloride in N,N-dimethyl formamide in the presence of imidazole .
- compounds of formula (II) may be obtained by reacting the Grignard reagent formed from magnesium and a compound of formula (V):
- Compounds of formula (V), may be obtained by reacting 4-bromophenol with a compound of the formula R'-CH 2 X in the presence of a base such as potassium carbonate.
- the present invention provides processes, as herein described, for preparing the compounds of formula (I).
- 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. turf, rye, coffee, pears, apples, peanuts, sugar beet, vegetables and ornamental plants;
- Erysiphe graminis on barley, wheat, rye and turf and other powdery mildews on various hosts such as Sphaerotheca macularis on hops, Sphaerotheca fuliginea on cucurbits (e.g. cucumber), Podosphaera leucotricha on apple and Uncinula necator on vines; Cochliobolus spp., Helminthosporium spp., Drechslera spp. (Pyrenophora spp.), Rhynchosporium spp., Septoria spp.
- Ramularia spp. on sugar beet and other hosts 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 Eutypa lata, Guignardia bidwellii, Phellinus igniarus, Phomopsis viticola, Pseudopezicula tracheiphila and Stereum hirsutum; other pathogens on lumber, notably Cephaloascus fragrans, Ceratocystis spp., Ophiostoma piceae, Penicillium spp., Trichoderma pseudokoningii, Trichoderma viride, Trichoderma harzianum, Aspergillus niger, Leptographium lindbergi and
- 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.
- 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. Moreover, 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 0. Ig 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.
- 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 irrigation systems.
- plant as used herein includes seedlings, bushes and trees. Furthermore, the fungicidal method of the invention includes preventative, protectant, prophylactic, systemic 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-dimethylformamide).
- 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.
- 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 hydrophilic 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 (£>N-methyl-2-(2-phenoxyphenyl)-2- methoxyiminoacetamide, (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy- iminoacetamide, (R5)-l-aminopropylphosphonic acid, (RS)-4-(4-chlorophenyl)- -2-phenyl-2-( IH- 1 ,2,4-triazol- 1 -ylmethyl)butyronitrile, (Z)-N-but-2-enyloxymethyl- -2-chloro-2',6'-diethylacetanilide, 1 -(2-cyano-2-methoxyiminoacetyl)-3-ethyl urea, 4-(2,2-difluoro- 1 ,3-benzodioxol-4-yl)pyrrole-3-carbonitrile
- Methanesulphonyl chloride (677 mg, 5.91 mmol) was to a stirred solution of 2- hydroxymethylpyrazine (500 mg, 4.5 mmol) and triethylamine (1.3 ml, 9.1 mmol) in dry dichloromethane (10 ml) at 0 °C. The solution was stirred at ambient temperature for 5 hours, then poured into water and extracted with dichloromethane. The combined organic extracts were washed with water and brine, dried and evaporated to provide a dark brown oil.
- EXAMPLE 8 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 Innes 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 a maximum retention. Tween 20 was added to give a final concentration of 0.05% when the sprays were applied to cereals.
- the compounds were applied to the foliage (by spraying) one or two days before the plant was inoculated with the disease.
- Foliar pathogens were applied by spray as zoosporangial suspensions onto the leaves of test plants. After inoculation, the plants were put into an appropriate environment to allow infection to proceed and then incubated until the disease was ready for assessment. The period between inoculation and assessment varied from four to fourteen days according to the disease and environment.
- the disease level present (i.e. leaf area covered by actively sporulating disease) on each of the treated plants was recorded using the following assessment scale:
- 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 9.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (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
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU21673/97A AU2167397A (en) | 1996-04-15 | 1997-03-24 | Fungicidal oxazolidinedione derivatives |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9607784.7 | 1996-04-15 | ||
GBGB9607784.7A GB9607784D0 (en) | 1996-04-15 | 1996-04-15 | Fungicides |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997038995A1 true WO1997038995A1 (fr) | 1997-10-23 |
Family
ID=10792089
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1997/000822 WO1997038995A1 (fr) | 1996-04-15 | 1997-03-24 | Derives fongicides d'oxazolidinediones |
Country Status (4)
Country | Link |
---|---|
AU (1) | AU2167397A (fr) |
GB (1) | GB9607784D0 (fr) |
WO (1) | WO1997038995A1 (fr) |
ZA (1) | ZA972985B (fr) |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0393911A1 (fr) * | 1989-04-21 | 1990-10-24 | E.I. Du Pont De Nemours And Company | Oxazolidinones fongicides |
WO1991015480A1 (fr) * | 1990-04-10 | 1991-10-17 | E.I. Du Pont De Nemours And Company | Oxazolidinones fongicides |
WO1991019703A2 (fr) * | 1990-06-11 | 1991-12-26 | E.I. Du Pont De Nemours And Company | Iminooxazolidinones fongicides |
EP0503798A1 (fr) * | 1991-03-15 | 1992-09-16 | E.I. Du Pont De Nemours And Company | 4-Thioxooxazolidin-2-ones et 4-iminooxazoliden-2-ones fongicides |
WO1993018016A1 (fr) * | 1992-03-11 | 1993-09-16 | E.I. Du Pont De Nemours And Company | Oxazolidinones fongicides |
WO1993022299A1 (fr) * | 1992-04-24 | 1993-11-11 | E.I. Du Pont De Nemours And Company | Oxazolidinones fongicides |
WO1994011359A1 (fr) * | 1992-11-13 | 1994-05-26 | E.I. Du Pont De Nemours And Company | Procedes de preparation de 2,4-oxazolidinediones |
JPH06220049A (ja) * | 1993-01-27 | 1994-08-09 | Nissan Chem Ind Ltd | オキサゾリノン誘導体および農園芸用殺菌剤 |
-
1996
- 1996-04-15 GB GBGB9607784.7A patent/GB9607784D0/en active Pending
-
1997
- 1997-03-24 AU AU21673/97A patent/AU2167397A/en not_active Abandoned
- 1997-03-24 WO PCT/GB1997/000822 patent/WO1997038995A1/fr active Application Filing
- 1997-04-08 ZA ZA9702985A patent/ZA972985B/xx unknown
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0393911A1 (fr) * | 1989-04-21 | 1990-10-24 | E.I. Du Pont De Nemours And Company | Oxazolidinones fongicides |
WO1991015480A1 (fr) * | 1990-04-10 | 1991-10-17 | E.I. Du Pont De Nemours And Company | Oxazolidinones fongicides |
WO1991019703A2 (fr) * | 1990-06-11 | 1991-12-26 | E.I. Du Pont De Nemours And Company | Iminooxazolidinones fongicides |
EP0503798A1 (fr) * | 1991-03-15 | 1992-09-16 | E.I. Du Pont De Nemours And Company | 4-Thioxooxazolidin-2-ones et 4-iminooxazoliden-2-ones fongicides |
WO1993018016A1 (fr) * | 1992-03-11 | 1993-09-16 | E.I. Du Pont De Nemours And Company | Oxazolidinones fongicides |
WO1993022299A1 (fr) * | 1992-04-24 | 1993-11-11 | E.I. Du Pont De Nemours And Company | Oxazolidinones fongicides |
WO1994011359A1 (fr) * | 1992-11-13 | 1994-05-26 | E.I. Du Pont De Nemours And Company | Procedes de preparation de 2,4-oxazolidinediones |
JPH06220049A (ja) * | 1993-01-27 | 1994-08-09 | Nissan Chem Ind Ltd | オキサゾリノン誘導体および農園芸用殺菌剤 |
Non-Patent Citations (1)
Title |
---|
CHEMICAL ABSTRACTS, vol. 122, no. 11, 13 March 1995, Columbus, Ohio, US; abstract no. 133170q, NAKJIMA,Y. ET AL.: "Preparation of oxazolidinone derivatives as agrochemical fungicides" page 1116; XP002034233 * |
Also Published As
Publication number | Publication date |
---|---|
AU2167397A (en) | 1997-11-07 |
GB9607784D0 (en) | 1996-06-19 |
ZA972985B (en) | 1997-10-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5939563A (en) | O-methyloximes of benzopyran-3,4- and benzofuran-2,3-diones and methods for their preparation | |
US5668160A (en) | Fungicidal oxazolyl and oxadiazolyl derivatives | |
US5723471A (en) | Pyrimidine fungicides | |
US5723473A (en) | Propenoic acid derivatives useful as fungicides | |
US6169101B1 (en) | Pyridine derivatives as fungicides | |
US5491156A (en) | Benzoxazole, benzothiazole and benzimidazole derivatives as fungicides | |
US6124356A (en) | Fungicides | |
EP0858997B1 (fr) | Fongicides | |
WO1997049697A1 (fr) | Pyridylaminopyrimidines fongicides | |
WO1997038995A1 (fr) | Derives fongicides d'oxazolidinediones | |
WO1997038997A1 (fr) | Oxazolidinediones substituees et leur utilisation comme fongicides | |
AU660711C (en) | Fungicides | |
EP0664791A1 (fr) | Procede de preparation de derives d'oxime, certains intermediaires et leur utilisation en tant que fongicides | |
GB2276380A (en) | Fungicidal and insecticidal compounds containing a phenylsulphurpentafluoride group | |
WO1997049696A1 (fr) | Pyridylaminopyrimidines utilises comme fongicides | |
GB2314080A (en) | Fungicidal cyclic boron compounds | |
WO1996015672A1 (fr) | Composition fongicide |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE HU IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK TJ TM TR TT UA UG US UZ VN AM AZ BY KG KZ MD RU TJ TM |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH KE LS MW SD SZ UG AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
NENP | Non-entry into the national phase |
Ref country code: JP Ref document number: 97536827 Format of ref document f/p: F |
|
NENP | Non-entry into the national phase |
Ref country code: CA |
|
122 | Ep: pct application non-entry in european phase |