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WO1998051673A1 - Nouveaux derives de l'imidazole et du pyrrole utiles comme fongicides - Google Patents

Nouveaux derives de l'imidazole et du pyrrole utiles comme fongicides Download PDF

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Publication number
WO1998051673A1
WO1998051673A1 PCT/GB1998/001208 GB9801208W WO9851673A1 WO 1998051673 A1 WO1998051673 A1 WO 1998051673A1 GB 9801208 W GB9801208 W GB 9801208W WO 9851673 A1 WO9851673 A1 WO 9851673A1
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WO
WIPO (PCT)
Prior art keywords
optionally substituted
compounds
alkyl
compound
phenyl
Prior art date
Application number
PCT/GB1998/001208
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English (en)
Inventor
Christopher Geoffrey Earnshaw
Thomas Lawley Hough
Dale Robert Mitchell
Original Assignee
Agrevo Uk 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
Application filed by Agrevo Uk Limited filed Critical Agrevo Uk Limited
Priority to AU72187/98A priority Critical patent/AU7218798A/en
Publication of WO1998051673A1 publication Critical patent/WO1998051673A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D413/10—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 carbon chain containing aromatic rings

Definitions

  • This invention relates to new derivatives of imidazole or pyrrole useful as fungicides.
  • W is N or CH
  • A is a phenyl or a 5 or 6 membered heterocyclyl group, each of which is optionally substituted one or more times by the same or different group 0.1 ;
  • Q and ⁇ which may be the same or different, are Y-(X) n -, optionally substituted amino, halogen, cyano, nitro, or two adjacent groups together with the carbon atoms to which they are attached can form an optionally substituted benzo or heterocyclic ring;
  • R 1 is C ⁇
  • Y and R 2 which may be the same or different, are alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, phenyl or heterocyclyl, each of which is optionally substituted, hydrogen or acyl;
  • X is oxygen or sulfur;
  • n is 0 or 1;
  • s is 0 to 2, together with complexes with metal salts, as well as salts with bases of compounds which are acids and salts with acids of compounds which are bases.
  • Alkyl groups are preferably of 1 to 20, e.g. 1 to 6, carbon atoms.
  • Alkenyl and alkynyl groups are generally of 2 to 6 carbon atoms.
  • Cycloalkyl or cycloalkenyl groups are preferably of 3 to 8 carbon atoms.
  • Substituents when present on any alkyl, cycloalkyl, cycloalkenyl, alkenyl or alkynyl moiety include halogen, azido, cyano, optionally substituted alkoxy, optionally substituted alkylthio, hydroxy, nitro, optionally substituted amino, acyl, acyloxy, optionally substituted phenyl, optionally substituted heterocyclyl, optionally substituted phenoxy and optionally substituted heterocyclyloxy.
  • Cycloalkyl or cycloalkenyl groups may also be substituted by alkyl, alkenyl or alkynyl
  • Substituents when present on any phenyl or heterocyclyl group are usually one or more of the same groups as defined for Q.
  • heterocyclyl includes both aromatic and non-aromatic heterocyclyl groups.
  • Heterocyclyl groups are generally 5, 6 or 7-membered rings containing up to 4 hetero atoms selected from nitrogen, oxygen and sulfur.
  • Examples of heterocyclyl groups are furyl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, dioxolanyl, oxazolyl, thiazolyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, pyranyl, pyridyl, piperidinyl, dioxanyl, morphoiino, dithianyl, thiomorpholino, pyridazinyl,
  • Amino groups may be substituted for example by one or two optionally substituted alkyl or acyl, or two substituents can form a ring, preferably a 5 to 7-membered ring, which may be substituted and may contain other heteroatoms, for example morpholine, thiomorpholine, or piperidine. This ring can be substituted as for heterocyclyl.
  • acyl includes the residue of sulfur and phosphorus-containing acids as well as carboxylic acids.
  • Examples of acyl groups are thus -COR 5 , -COOR 5 , -CXNR 5 R 6 , -CON(R 5 )OR 6 , -COONR 5 R 6 , -CON(R 5 )NR 6 R 7 , -COSR 5 , -CSSR 5 , -S(O) p R 5 ,
  • R 5 , R 6 and R 7 which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted phenyl or optionally substituted heterocyclyl, or R 5 and R®, or R ⁇ and R 7 , together with the atom(s) to which they are attached can form a ring, q is 1 or 2 and X is O or S.
  • Complexes are usually formed from a salt of formula MAn2, in which M is a divalent metal cation, e.g. copper, manganese, cobalt, nickel, iron or zinc and An is one equivalent of an anion, e.g. chloride, nitrate or sulfate.
  • M is a divalent metal cation, e.g. copper, manganese, cobalt, nickel, iron or zinc
  • An is one equivalent of an anion, e.g. chloride, nitrate or sulfate.
  • W is preferably N.
  • Rl is preferably methyl or ethyl.
  • R 2 is preferably hydrogen or C--
  • Z is a heterocyclic group it is preferably carbon linked to the phenyl. Especially preferred is 1 ,2,4-oxadiazol-3-yl, substituted in the 5-position by methyl or ethyl.
  • A is preferably phenyl, which is generally substituted by one or two Ql groups.
  • Q.1 is preferably chloro or methoxy or two adjacent Q 1 groups form a methylenedioxy ring.
  • s is preferably 0.
  • W is CH
  • s is preferably 1
  • Q is generally in the 2-position and is preferably alkyl or haloalkyl, especially methyl.
  • the compounds of the invention have particularly advantageous activity against fungal pathogens of plants and usually those pathogens of Ascomycete origin, especially against mildew diseases of plants, particularly cereal powdery mildew (Erysiphe graminis), cucumber powdery mildew (Erysiphe cichoracearum), vine downy mildew ⁇ Uncinula necato ⁇ , and apple powdery mildew ⁇ Podosphaera leuchotricha).
  • mildew diseases of plants particularly cereal powdery mildew (Erysiphe graminis), cucumber powdery mildew (Erysiphe cichoracearum), vine downy mildew ⁇ Uncinula necato ⁇ , and apple powdery mildew ⁇ Podosphaera leuchotricha).
  • mildew diseases of plants particularly cereal powdery mildew (Erysiphe graminis), cucumber powdery mildew (Erysiphe cichoracearum), vine downy mildew
  • rice blast (Pyricularia oryzae), cereal eyespot (Pseudocercosporella herpotrichoides), rice sheath blight (Pellicularia sasakii), grey mould (Botrytis cinerea), wheat brown rust (Puccinia recondita), late tomato or potato blight (Phytophthora infestans), apple scab (Venturia inaequalis) and glume blotch (Leptosphaeria nodorum).
  • Some compounds may be active against only a few pathogens whereas others may have a broader spectrum of activity.
  • the compounds of the invention are generally formulated in conventional compositions used for fungicides. These compositions can contain one or more additional pesticides, for example compounds known to possess herbicidal, fungicidal, insecticidal, acaricidal or nematicidal properties. In addition the compounds may be merely mixed with the additional pesticide.
  • the diluent or carrier in the composition of the invention can be a solid or a liquid optionally in association with a surface-active agent, for example a dispersing agent, emulsifying agent or wetting agent.
  • Suitable surface-active agents include anionic compounds such as a carboxylate, for example a metal carboxylate of a long chain fatty acid; an N-acylsarcosinate; mono- or di-esters of phosphoric acid with fatty alcohol ethoxylates or salts of such esters; fatty alcohol sulfates such as sodium dodecyl sulfate, sodium octadecyl sulfate or sodium cetyl sulfate; ethoxylated fatty alcohol sulfates; ethoxylated alkylphenol sulfates; lignin sulfonates; petroleum sulfonates; alkyl-aryl sulfonates such as alkyl-benzene s
  • butyl-naphthalene sulfonate salts of sulfonated naphthalene-formaldehyde condensates; salts of sulfonated phenol-formaldehyde condensates; or more complex sulfonates such as the amide sulfonates, e.g. the sulfonated condensation product of oleic acid and N-methyl taurine or the dialkyl sulfosuccinates, e.g. the sodium sulfonate of dioctyl succinate.
  • amide sulfonates e.g. the sulfonated condensation product of oleic acid and N-methyl taurine or the dialkyl sulfosuccinates, e.g. the sodium sulfonate of dioctyl succinate.
  • Nonionic agents include condensation products of fatty acid esters, fatty alcohols, fatty acid amides or fatty-alkyl- or alkenyl-substituted phenols with ethylene oxide, fatty esters of polyhydric alcohol ethers, e.g. sorbitan fatty acid esters, condensation products of such esters with ethylene oxide, e.g. polyoxyethylene sorbitan fatty acid esters, block copolymers of ethylene oxide and propylene oxide, acetylenic glycols such as 2,4,7,9-tetramethyl-5-decyne-4,7-diol, or ethoxylated acetylenic glycols.
  • a cationic surface-active agent examples include, for instance, an aliphatic mono-, di-, or polyamine as an acetate, naphthenate or oleate; an oxygen-containing amine such as an amine oxide or polyoxyethylene alkylamine; an amide-linked amine prepared by the condensation of a carboxylic acid with a di- or polyamine; or a quaternary ammonium salt.
  • compositions of the invention can take any form known in the art for the formulation of agrochemicals, for example, a solution, a dispersion, an aqueous emulsion, a dusting powder, a seed dressing, a fumigant, a smoke, a dispersible powder, an emulsifiable concentrate or granules. Moreover it can be in a suitable form for direct application or as a concentrate or primary composition which requires dilution with a suitable quantity of water or other diluent before application.
  • the composition comprises a compound of the invention dispersed in a liquid medium, preferably water. It is often convenient to supply the consumer with a primary composition which can be diluted with water to form a dispersion having the desired concentration.
  • the primary composition can be provided in any one of the following forms. It can be a dispersible solution which comprises a compound of the invention dissolved in a water-miscible solvent with the addition of a dispersing agent.
  • a further alternative comprises a compound of the invention in the form of a finely ground powder in association with a dispersing agent and intimately mixed with water to give a paste or cream which can if desired be added to an emulsion of oil in water to give a dispersion of active ingredient in an aqueous oil emulsion.
  • An emulsifiable concentrate comprises a compound of the invention dissolved in a water-immiscible solvent together with an emulsifying agent and which is formed into an emulsion on mixing with water.
  • a dusting powder comprises a compound of the invention intimately mixed with a solid pulverulent diluent, for example, kaolin.
  • a granular solid comprises a compound of the invention associated with similar diluents to those which may be employed in dusting powders, but the mixture is granulated by known methods. Alternatively it comprises the active ingredient adsorbed or absorbed on a pre-granular diluent, for example, Fuller's earth, attapulgite or limestone grit.
  • a wettable powder usually comprises the active ingredient in admixture with a suitable surfactant and an inert powder diluent such as china clay.
  • a suitable concentrate particularly when the product is a solid, is a flowable suspension concentrate which is formed by grinding the compound with water, a wetting agent and a suspending agent.
  • the concentration of the active ingredient in the composition of the present invention is preferably within the range of 1 to 30 per cent by weight, especially 5 to 30 per cent by weight.
  • the amount of active ingredient can vary widely and can be, for example, from 5 to 95 per cent by weight of the composition.
  • the concentration of the active ingredient in the composition of the present invention, as applied to plants is preferably within the range of 0.0001 to 1.0 per cent by weight, especially 0.0001 to 0.01 per cent by weight.
  • the amount of active ingredient can vary widely and can be, for example, from 5 to 95 per cent by weight of the composition.
  • the compound is generally applied to seeds, plants or their habitat.
  • the compound can be applied directly to the soil before, at or after drilling so that the presence of active compound in the soil can control the growth of fungi which may attack seeds.
  • the active compound can be applied in any manner which allows it to be intimately mixed with the soil such as by spraying, by broadcasting a solid form of granules, or by applying the active ingredient at the same time as drilling by inserting it in the same drill as the seeds.
  • a suitable application rate is within the range of from 5 to 1000 g per hectare, more preferably from 10 to 500 g per hectare.
  • the active compound can be applied directly to the plant by, for example, spraying or dusting either at the time when the fungus has begun to appear on the plant or before the appearance of fungus as a protective measure.
  • spraying or dusting either at the time when the fungus has begun to appear on the plant or before the appearance of fungus as a protective measure.
  • the preferred mode of application is by foliar spraying. It is generally important to obtain good control of fungi in the early stages of plant growth as this is the time when the plant can be most severely damaged.
  • the spray or dust can conveniently contain a pre- or post-emergence herbicide if this is thought necessary.
  • it is practicable to treat the roots of a plant before or during planting for example, by dipping the roots in a suitable liquid or solid composition.
  • a suitable rate of application is from 0.025 to 5 kg per hectare, preferably from 0.05 to 1 kg per hectare.
  • the compounds of the invention can be applied to plants, or parts thereof, which have been genetically modified to exhibit a trait such as fungal and/or herbicidal resistance.
  • the starting compounds are either known or can be prepared in known manner.
  • Example 2 2-[2-(4-Methoxyphenyl)imidazol-1-yl]benzonitrile, from Example 1 (4.6 g), hydroxylamine hydrochloride (2.3 g) and potassium carbonate (2.3 g) were heated under reflux in aqueous ethanol overnight. The mixture was cooled and the solvent removed under reduced pressure. The residue was washed with water and the solid collected by filtration. The solid was washed with dichloromethane to give 2-[2-(4- methoxyphenyl)imidazol-1-yl]benzamide oxime, m.p. 187-190°C. (Compound 2)
  • Example 3 The product of Example 2 (1.2 g) and acetic anhydride (0.8 ml) were heated under reflux for 2 hours in acetic acid (50 ml). The mixture was cooled and the solvent removed under reduced pressure. The residue was treated with water and extracted with dichloromethane. The organic layer was dried and evaporated. The residue was purified by silica gel column chromatography to give 5- ⁇ 2-[2-(4-methoxyphenyl)- imidazol-1-yl]phenyl ⁇ -3-methyl-1 ,2,4-oxadiazole, as an orange semi-solid. (Compound 3)
  • N,N-dimethyl-1 ,1-dimethoxyethylamine (5.7 g) was heated under reflux for 1 1 /2 hours. The mixture was evaporated to dryness to give crude Nl-[1-(dimethylamino)- ethylidene]-2-[2-(4-methoxyphenyl)1 H-1-imidazolyl]benzamide.
  • a solution of this compound (2.14 g) in acetic acid (10 ml) was treated with hydroxylamine hydrochloride (0.6 g), dioxane (10 ml) and aqueous sodium hydroxide (4.4.ml of 2M) and the mixture heated at 90°C for 2 hours.
  • Example 7 A solution of the product of Example 6 (0.71 g) in dioxane (25 ml) was heated under reflux for 3 days. The solvent was evaporated under reduced pressure and the residue purified by silica gel column chromatography to give 3- ⁇ 2-[2-(1 ,3-benzodioxol- 5-yl)-1/-/-1-imidazolyl]phenyl ⁇ -5-methyl-1,2,4-oxadiazole, as a yellow gum. (Compound 7) The following compounds of the invention were prepared in an analogous manner to one of the previous examples
  • Compounds are assessed for activity against one or more of the following:
  • Erysiphe graminis f. sp. tritici wheat powdery mildew Pyricularia oryzae: rice blast
  • Leptosphaeria nodorum glume blotch
  • Plasmopara viticola downy mildew of vines Aqueous solutions or dispersions of the compounds at the desired concentration, including a wetting agent, were applied by spray or by drenching the stem base of the test plants, as appropriate. After a given time, plants or plant parts were inoculated with appropriate test pathogens and kept under controlled environmental conditions suitable for maintaining plant growth and development of the disease. After an appropriate time, the degree of infection of the affected part of the plant was visually estimated. Compounds are assessed on a score of 1 to 3 where 1 is little or no control, 2 is moderate control and 3 is good to total control. At a concentration of 500 ppm (w/v) or less, the following compounds scored 2 or more against the fungi specified.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne des composés de formule (I), dans laquelle W est N ou CH; A est phényle ou un groupe hétérocyclyle à 5 ou 6 éléments, dont chacun peut être substitué une ou plusieurs fois par un groupe Q1 identique ou différent; Z est COOR1, C(NH¿2)=NOR?2 ou un groupe oxadiazolyle ou thiazolyle, substitué par alkyle, haloalkyle ou cycloalkyle; Q et Q1, identiques ou différents, sont Y-(X)¿n?-, amino éventuellement substitué, halogène, cyano, nitro, ou bien deux groupes adjacents aux atomes de carbone sur lesquels ils sont fixés forment un noyau benzo ou hétérocyclique éventuellement substitué; R?1¿ est alkyle C¿1?-C6; Y et R?2¿, identiques ou différents, sont alkyle, cycloalkyle, cycloalcényle, alcényle, alcynyle, phényle ou hétérocyclyle, tous pouvant être substitués, hydrogène ou acyle; X est oxygène ou soufre; n est 0 ou 1; et s est compris entre 0 et 2, avec des complexes renfermant des sels métalliques, ainsi que des sels avec des bases de composés qui sont des acides et des sels avec des acides de composés qui sont des bases. Ces composés sont utiles comme fongicides, notamment contre les champignons phytopathogènes.
PCT/GB1998/001208 1997-05-09 1998-05-08 Nouveaux derives de l'imidazole et du pyrrole utiles comme fongicides WO1998051673A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU72187/98A AU7218798A (en) 1997-05-09 1998-05-08 Novel imidazole and pyrrole derivatives useful as fungicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9709317.3A GB9709317D0 (en) 1997-05-09 1997-05-09 Fungicides
GB9709317.3 1997-05-09

Publications (1)

Publication Number Publication Date
WO1998051673A1 true WO1998051673A1 (fr) 1998-11-19

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PCT/GB1998/001208 WO1998051673A1 (fr) 1997-05-09 1998-05-08 Nouveaux derives de l'imidazole et du pyrrole utiles comme fongicides

Country Status (3)

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AU (1) AU7218798A (fr)
GB (1) GB9709317D0 (fr)
WO (1) WO1998051673A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009137538A3 (fr) * 2008-05-08 2012-04-19 E. I. Du Pont De Nemours And Company Azoles substitués fongicides
JP2013509408A (ja) * 2009-10-29 2013-03-14 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 複素二環置換されたアゾリルベンゼン殺菌・殺カビ剤

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1563664A (en) * 1977-01-06 1980-03-26 Sumitomo Chemical Co N-benzoylanthranilates processes for producing them and compositions containing them
US4339448A (en) * 1978-11-02 1982-07-13 Basf Aktiengesellschaft Imidazole-copper complex compounds and fungicides containing them
WO1997010228A1 (fr) * 1995-09-16 1997-03-20 Agrevo Uk Limited Anilides substitues de l'acide benzoique ou thiobenzoique utilises comme fongicides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1563664A (en) * 1977-01-06 1980-03-26 Sumitomo Chemical Co N-benzoylanthranilates processes for producing them and compositions containing them
US4339448A (en) * 1978-11-02 1982-07-13 Basf Aktiengesellschaft Imidazole-copper complex compounds and fungicides containing them
WO1997010228A1 (fr) * 1995-09-16 1997-03-20 Agrevo Uk Limited Anilides substitues de l'acide benzoique ou thiobenzoique utilises comme fongicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
STETTER H ET AL: "Preparation of bi- and tricyclic pyrrole systems", LIEBIGS ANN. CHEM., no. 5, 1980, pages 703 - 714, XP002073707 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009137538A3 (fr) * 2008-05-08 2012-04-19 E. I. Du Pont De Nemours And Company Azoles substitués fongicides
WO2009137651A3 (fr) * 2008-05-08 2012-04-26 E. I. Du Pont De Nemours And Company Azoles substitués fongicides
JP2013509408A (ja) * 2009-10-29 2013-03-14 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 複素二環置換されたアゾリルベンゼン殺菌・殺カビ剤

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AU7218798A (en) 1998-12-08
GB9709317D0 (en) 1997-06-25

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