WO1992007835A1 - Fongicides aux imidazoles - Google Patents
Fongicides aux imidazoles Download PDFInfo
- Publication number
- WO1992007835A1 WO1992007835A1 PCT/GB1991/001836 GB9101836W WO9207835A1 WO 1992007835 A1 WO1992007835 A1 WO 1992007835A1 GB 9101836 W GB9101836 W GB 9101836W WO 9207835 A1 WO9207835 A1 WO 9207835A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- optionally substituted
- alkyl
- compound
- aryl
- alkenyl
- Prior art date
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title description 16
- 239000000417 fungicide Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- -1 cycloakenyl Chemical group 0.000 claims abstract description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 18
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- 125000002252 acyl group Chemical group 0.000 claims abstract description 16
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 12
- 241000233866 Fungi Species 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
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- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 239000011593 sulfur Substances 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract 6
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- 238000000034 method Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
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- 230000000694 effects Effects 0.000 abstract description 4
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
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- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
- WEOVZYGEOHNNDT-UHFFFAOYSA-N n-(4-chlorophenyl)-4-cyano-1-(dimethylsulfamoyl)imidazole-2-carboxamide Chemical compound CN(C)S(=O)(=O)N1C=C(C#N)N=C1C(=O)NC1=CC=C(Cl)C=C1 WEOVZYGEOHNNDT-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/68—Halogen atoms
-
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/70—One oxygen atom
-
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
-
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
Definitions
- This invention relates to imidazole fungicides.
- R 1 is -S0 ⁇ 7 2R- , -P-R 7 or -COR 8
- R 5 is aryl, optionally substituted alkyl or optionally substituted amino
- R 6 and R 7 may be the same or different and are amino, alkoxy or alkylthio, each of which is optionally substituted;
- R 8 has the same meaning as R 5 or can be alkoxy, alkenyloxy, alkynyloxy or alkylthio, each of which is optionally substituted, or is aryloxy;
- R 9 is hydrogen, optionally substituted alkyl, alkenyl, alkynyl, alkoxycarbonyl, acyl, aryl or cycloalkyl;
- R 10 is hydrogen, optionally substituted alkyl, alkenyl or alkynyl
- R 11 is alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, all of which are optionally substituted, or is aryl;
- ,12 has the same meaning as Rll or is acyl
- Z is oxygen or sulfur; and p is 0 or 1.
- R 3 is alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, alkanoyl or amino, all of which are optionally substituted, hydrogen, halogen, hydroxy, nitro, acyl,
- R 12 0 or aryl
- R 5 is aryl, optionally substituted alkyl or optionally substituted amino
- R 6 and R 7 may be the same or different and are amino, alkoxy or alkylthio, each of which is optionally substituted
- R 9 is hydrogen, optionally substituted alkyl, alkenyl, alkynyl, alkoxycarbonyl, acyl, aryl or cycloalkyl
- R 10 is hydrogen, optionally substituted alkyl, alkenyl or lkynyl
- R 11 is alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl or amino, all of which are optionally substituted, or is aryl;
- R 12 has the same meaning as R 11 or is acyl; Z is oxygen or sulfur; and p is 0, 1 or 2.
- Alkyl, alkanoyl and alkoxy groups are preferably of 1 to 8 carbon atoms, especially methyl, and alkenyl and alkynyl groups are usually of 3 to 4 carbon atoms. Substituents, when present on any such group, include halogen, hydroxy, alkoxy and aryl.
- Aryl groups are usually phenyl, optionally substituted, e.g.
- R 13 has the same meaning as R 5 or can be hydroxy, alkoxy, alkenyloxy, alkynyloxy or alkylthio, each of which is optionally substituted, or is aryloxy
- R 13 has the same meaning as R 5 or can be hydroxy, alkoxy, alkenyloxy, alkynyloxy or alkylthio, each of which is optionally substituted, or is aryloxy
- R 13 has the same meaning as R 5 or can be hydroxy, alkoxy, alkenyloxy, alkynyloxy or alkylthio, each of which is optionally substituted, or is aryloxy
- sulfamoyl optionally substituted amino, alkyl-SO , or aryl-SO , where g is 0, 1 or 2, and any alkyl or alkoxy group is optionally substituted.
- aryl may include heteroaryl groups such as thienyl, furyl or pyridyl and can also include polynuclear aromatic groups, such as naphthyl and benzimidazolyl.
- acyl can include residues of both carboxylic and sulfonic acids and includes the groups R 13 (0) r C0 and R 13 S0 2 , where R 13 has the same meaning as R 11 , or is optionally substituted amino and r is 0 or 1. It thus includes residues of carba ic and sulfa ic acids.
- Acyl groups are preferably alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, N,N-dialkylsulfamoyl or N-alkyl-N-arylsulfamoyl, in which the alkyl groups are e.g. of 1 to 4 carbon atoms, and the alkyl and phenyl can be substituted as previously mentioned.
- Amino groups are usually substituted by one or more of the groups R 11 , acyl, optionally substituted amino (including groups substituted through a double bond) , hydroxy or optionally substituted alkoxy, or two substituents can form a ring, e.g. a morpholino or piperidino ring.
- Sulfamoyl groups can be substituted similarly to amino groups.
- Cycloalkyl groups are usually of 3 to 8 carbon atoms especially cyclopentyl or cyclohexyl.
- R 1 is generally a substituted sulfamoyl group, especially dimethylsulfamoyl.
- R 2 is preferably cyano or thiocarbamoyl.
- R 3 is preferably phenyl or benzoyl, optionally substituted by up to three groups, selected from halogen, alkyl (especially methyl) , trifluoromethyl, nitro and alkoxy (especially methoxy) .
- the compounds of the invention have activity as fungicides, especially against fungal diseases of plants, e.g. downy mildews, especially vine downy mildew fPlasmopara viticola) , and late tomato blight and potato blight fPhytophthora infestans . They are also active against powdery mildews, such as barley powdery mildew (Erysiphe ⁇ raminis) , as well as being active against diseases such as rice blast (Pyricularia orvzae) and apple scab (Venturia inaequalis) . They may also have activity against other fungi, such as Botrvtis spp. ,
- the invention thus also provides a method of combating fungi at a locus infested or liable to be infested therewith, which comprises applying to the locus a compound of formula I.
- the invention also provides an agricultural composition
- an agricultural composition comprising a compound of formula I in admixture with an agriculturally acceptable diluent or carrier.
- composition of the invention may of course include more than one compound of the invention.
- composition can comprise one or more additional active ingredients, for example compounds known to possess plant-growth regulant, herbicidal, fungicidal,insecticidal or acaricidal properties.
- additional active ingredients for example compounds known to possess plant-growth regulant, herbicidal, fungicidal,insecticidal or acaricidal properties.
- the compounds of the invention can be used in sequence with the other active ingredient.
- 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.
- An emulsifiable concentrate comprises a compound of the invention dissolved in a water-immiscible solvent which is formed into an emulsion with water in the presence of an emulsifying agent.
- a dusting powder comprises a compound of the invention intimately mixed and ground 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 absorbed or adsorbed on a pre-granular diluent, for example, Fuller's earth, attapulgite or limestone grit.
- Wettable powders, granules or grains usually comprise the active ingredient in admixture with a suitable surfactant and an inert powder diluent such as china clay.
- Another suitable concentrate is a flowable suspension concentrate which is formed by grinding the compound with water or other liquid, a wetting agent and a suspending agent.
- the concentration of the active ingredient in the composition of the present invention, as applied to plants is preferably within the range of 0.01 to 3.0 per cent by weight, especially 0.01 to 1.0 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 0.01 to 10 kg per hectare, more preferably from 0.05 to 1 kg 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.
- 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.
- a suitable rate of application is from 0.01 to 10 kg. per hectare, preferably from 0.05 to 5 kg per hectare.
- the compounds of the invention may be prepared, in known manner, in a variety of ways, for example by reacting a compound of formula II ⁇ N
- R 2 is as defined above, except for thiocarbamoyl, with a compound of formula R*Q, where Q is a leaving group, such as halogen, especially chlorine.
- Compounds of formula II can be obtained by reacting the corresponding compound where R 2 is trihalomethyl with ammonium hydroxide to give a compound where R 2 is cyano.
- Compounds of formula I, where R 2 is cyano can be modified in known manner to give compounds where R 2 is thiocarbamoyl, by reaction with hydrogen sulfide and if desired modifying this group in known manner to give compounds where R 9 is not hydrogen. These reactions are usually carried out using a suitable acyl halide or isocyanate, for instance as described in EP 219192.
- R 30 CO is the same alkanoyl or aroyl group, e.g. using a dichromate, such as pyridinium dichromate.
- the invention is illustrated in the following Examples. Structures of isolated novel compounds were confirmed by elemental and/or other appropriate analyses. Temperatures are in °C and are uncorrected.
- the compounds of the invention were assessed for activity against one or more of the following:
- Plasmopara viticola vine downy mildew (PV)
- Phytophthora infestans late tomato blight (PI)
- Aqueous solutions or dispersions of the compounds at the desired concentration, including a wetting agent, were sprayed onto the appropriate plant and then inoculated by spraying with spore suspensions of the fungi. Plants were then kept under controlled environment conditions suitable for maintaining plant growth and development of the disease. After an appropriate time, the degree of infection of the leaf surface was visually estimated.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Composés de la formule (I), dans laquelle R1 représente -SO¿2R?5 ou (a), R2 is -CN, (b) ou -CH=N-OR10, R3 est alcoyle, cycloalkyle, cycloalcényle, alcényle, alcynyle, alcanoyle, ou amino, tous étant éventuellement substitués, hydrogène, halogène, hydroxy, nitro, acyle, R12O ou aryle; R5 est aryle, alkyle éventuellement substitué ou amino éventuellement substitué; R6 et R7 peuvent être identiques ou différents, et sont amino, alkoxy ou alkylthio, chacun étant éventuellement substitué; R9 est hydrogène, alkyle, alcényle, alcynyle, alcoxycarbonyle, acyle, aryle ou cycloalkyle éventuellement substitué; R10 est hydrogène, alcyle, alcényle ou alcynyle éventuellement substitué; R11 est alcyle, cycloalkyle, cycloalcényle, alcényle, alcynyle ou amino, tous étant éventuellement substitués, ou aryle; R12 a la même notation R11 ou est acyle; Z est oxygène ou soufre; et p est 0, 1 ou 2; lesdits composés présentent une activité contre les champignons phytopathogènes.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9023082.2 | 1990-10-24 | ||
GB909023082A GB9023082D0 (en) | 1990-10-24 | 1990-10-24 | Fungicides |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1992007835A1 true WO1992007835A1 (fr) | 1992-05-14 |
Family
ID=10684244
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1991/001836 WO1992007835A1 (fr) | 1990-10-24 | 1991-10-21 | Fongicides aux imidazoles |
Country Status (2)
Country | Link |
---|---|
GB (1) | GB9023082D0 (fr) |
WO (1) | WO1992007835A1 (fr) |
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US6043377A (en) * | 1996-06-11 | 2000-03-28 | Bayer Aktiengesellschaft | Imidazole compounds |
US9873671B2 (en) | 2014-01-16 | 2018-01-23 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
US9884818B2 (en) | 2013-05-17 | 2018-02-06 | Janssen Sciences Ireland Uc | Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
US9895349B2 (en) | 2013-04-03 | 2018-02-20 | Janssen Sciences Ireland Us | N-phenyl-carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
US10071961B2 (en) | 2013-10-23 | 2018-09-11 | Janssen Sciences Ireland Uc | Carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
US10077239B2 (en) | 2015-09-29 | 2018-09-18 | Novira Therapeutics, Inc. | Crystalline forms of a hepatitis B antiviral agent |
US10125094B2 (en) | 2013-02-28 | 2018-11-13 | Janssen Sciences Ireland Uc | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B |
US10160743B2 (en) | 2013-05-17 | 2018-12-25 | Janssen Sciences Ireland Uc | Sulphamoylthiophenamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
US10196376B2 (en) | 2011-12-21 | 2019-02-05 | Novira Therapeutics, Inc. | Hepatitis B antiviral agents |
US10213420B2 (en) | 2014-02-05 | 2019-02-26 | Novira Therapeutics, Inc. | Combination therapy for treatment of HBV infections |
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US10392349B2 (en) | 2014-01-16 | 2019-08-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
US10441589B2 (en) | 2016-04-15 | 2019-10-15 | Novira Therapeutics, Inc. | Combinations and methods comprising a capsid assembly inhibitor |
US10450270B2 (en) | 2013-07-25 | 2019-10-22 | Janssen Sciences Ireland Uc | Glyoxamide substituted pyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
US10537580B2 (en) | 2015-03-19 | 2020-01-21 | Novira Therapeutics, Inc. | Azocane and azonane derivatives and methods of treating hepatitis B infections |
US10875876B2 (en) | 2015-07-02 | 2020-12-29 | Janssen Sciences Ireland Uc | Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
US10973801B2 (en) | 2018-03-14 | 2021-04-13 | Janssen Sciences Ireland Unlimited Company | Capsid assembly modulator dosing regimen |
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EP0284277A1 (fr) * | 1987-03-21 | 1988-09-28 | AgrEvo UK Limited | Fongicides de cyanoimidazole |
EP0337103A2 (fr) * | 1988-03-11 | 1989-10-18 | ISHIHARA SANGYO KAISHA, Ltd. | Composition biocide |
EP0432892A1 (fr) * | 1989-11-15 | 1991-06-19 | AgrEvo UK Limited | Fongicides dérivés de l'imidazol |
EP0298196B1 (fr) * | 1987-03-13 | 1993-06-02 | Ishihara Sangyo Kaisha, Ltd. | Composés d'imidazole et compositions biocides les contenant |
-
1990
- 1990-10-24 GB GB909023082A patent/GB9023082D0/en active Pending
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1991
- 1991-10-21 WO PCT/GB1991/001836 patent/WO1992007835A1/fr active Application Filing
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US4574010A (en) * | 1985-05-06 | 1986-03-04 | Stauffer Chemical Company | Herbicidal esters of N-substituted 2-bromo-4-methylimidazole-5-carboxylic acid |
EP0298196B1 (fr) * | 1987-03-13 | 1993-06-02 | Ishihara Sangyo Kaisha, Ltd. | Composés d'imidazole et compositions biocides les contenant |
EP0284277A1 (fr) * | 1987-03-21 | 1988-09-28 | AgrEvo UK Limited | Fongicides de cyanoimidazole |
EP0337103A2 (fr) * | 1988-03-11 | 1989-10-18 | ISHIHARA SANGYO KAISHA, Ltd. | Composition biocide |
EP0432892A1 (fr) * | 1989-11-15 | 1991-06-19 | AgrEvo UK Limited | Fongicides dérivés de l'imidazol |
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US6043377A (en) * | 1996-06-11 | 2000-03-28 | Bayer Aktiengesellschaft | Imidazole compounds |
US10196376B2 (en) | 2011-12-21 | 2019-02-05 | Novira Therapeutics, Inc. | Hepatitis B antiviral agents |
US10995064B2 (en) * | 2012-08-28 | 2021-05-04 | Janssen Sciences Ireland Uc | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B |
US10676429B2 (en) | 2012-08-28 | 2020-06-09 | Janssen Sciences Ireland Uc | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B |
AU2018204597B2 (en) * | 2012-08-28 | 2020-03-05 | Janssen Sciences Ireland Uc | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of Hepatitis B |
JP2019069940A (ja) * | 2012-08-28 | 2019-05-09 | ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー | スルファモイル−アリールアミド及びb型肝炎の治療のための薬剤としてのその使用 |
US10941113B2 (en) | 2013-02-28 | 2021-03-09 | Janssen Sciences Ireland Uc | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis B |
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US10392349B2 (en) | 2014-01-16 | 2019-08-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
US9873671B2 (en) | 2014-01-16 | 2018-01-23 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
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US10632112B2 (en) | 2014-02-05 | 2020-04-28 | Novira Therapeutics, Inc. | Combination therapy for treatment of HBV infections |
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US10537580B2 (en) | 2015-03-19 | 2020-01-21 | Novira Therapeutics, Inc. | Azocane and azonane derivatives and methods of treating hepatitis B infections |
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US10441589B2 (en) | 2016-04-15 | 2019-10-15 | Novira Therapeutics, Inc. | Combinations and methods comprising a capsid assembly inhibitor |
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Also Published As
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