WO1993007116A1 - Fungicides - Google Patents

Fungicides Download PDF

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Publication number
WO1993007116A1
WO1993007116A1 PCT/GB1992/001641 GB9201641W WO9307116A1 WO 1993007116 A1 WO1993007116 A1 WO 1993007116A1 GB 9201641 W GB9201641 W GB 9201641W WO 9307116 A1 WO9307116 A1 WO 9307116A1
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WO
WIPO (PCT)
Prior art keywords
compound
optionally substituted
formula
alkyl
reacting
Prior art date
Application number
PCT/GB1992/001641
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English (en)
French (fr)
Inventor
Ian Richard Matthews
Christopher Richard Ayles Godfrey
John Martin Clough
Original Assignee
Zeneca Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26299611&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO1993007116(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from GB919120771A external-priority patent/GB9120771D0/en
Priority claimed from GB919122875A external-priority patent/GB9122875D0/en
Priority to US08/211,390 priority Critical patent/US6465457B1/en
Priority to EP92918847A priority patent/EP0606251B1/en
Priority to JP50669493A priority patent/JP3371139B2/ja
Application filed by Zeneca Limited filed Critical Zeneca Limited
Priority to DE69216632T priority patent/DE69216632T2/de
Priority to AU25139/92A priority patent/AU660711C/en
Priority to KR1019940701021A priority patent/KR100229945B1/ko
Publication of WO1993007116A1 publication Critical patent/WO1993007116A1/en
Priority to US08/748,088 priority patent/US5777162A/en
Priority to KR1019997003766A priority patent/KR100231635B1/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
    • C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
    • C07C271/64—Y being a hydrogen or a carbon atom, e.g. benzoylcarbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
    • C07C317/42—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
    • C07C323/35—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
    • C07C323/36—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/38—Amides of thiocarboxylic acids
    • C07C327/48—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
    • C07C329/02—Monothiocarbonic acids; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
    • C07C329/02—Monothiocarbonic acids; Derivatives thereof
    • C07C329/04—Esters of monothiocarbonic acids
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C333/02—Monothiocarbamic acids; Derivatives thereof
    • C07C333/08—Monothiocarbamic acids; Derivatives thereof having nitrogen atoms of thiocarbamic groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/96—Esters of carbonic or haloformic acids
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid
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    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/76—Benzo[c]pyrans

Definitions

  • the present invention relates to carbonate, carbamate, thiocarbonate, dithiocarbonate and thiocarbamate derivatives that are useful as
  • fungicides to processes for preparing them, to compositions containing them and to methods of using them to combat fungi, especially fungal infections of plants.
  • CH 3 ON CCO 2 CH 3 and stereoisomers thereof; n is 0 or 1; X is oxygen or sulphur; Z is oxygen, sulphur or NR 1 ; R 1 is hydrogen or alkyl optionally substituted with halogen, C 1-6 alkoxy, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl or aryl; R 2 is alkyl, haloalkyl, alkenyl, alkynyl,
  • alkoxycarbonyl(C 1-4 )alkyl optionally substituted aryl, optionally substituted heteroaryl, optionally substituted aryl(C 1-4 )alkyl, optionally substituted heteroaryl(C 1-4 )alkyl, optionally substituted aryloxy(C 1-4 )- alkyl, optionally substituted heteroaryloxy(C 1-4 )alkyl, optionally substituted aryloxy(C 2-4 )alkenyl, optionally substituted heteroaryloxy- (C 2-4 )alkenyl, optionally substituted aryl(C 2-4 )alkenyl, optionally substituted heteroaryl(C 2-4 )alkenyl, optionally substituted arylcarbonyl- (C 1-4 )alkyl, optionally substituted heteroarylcarbonyl(C 1-4 )alkyl, optionally substituted aryloxycarbonyl-(C 1-4 )alkyl, optionally substituted heteroaryloxycarbonyl(C
  • the compounds of the invention may be obtained in the form of mixtures of (E)- and (Z)-geometric isomers. However, these mixtures can be separated into individual isomers, and this invention embraces such isomers and mixtures thereof in all proportions including those which consist substantially of the
  • Aryl is preferably phenyl.
  • Heteroaryl includes 5- and 6-membered aromatic rings containing one or more heteroatoms selected from the list comprising oxygen, sulphur and nitrogen and can be fused to benzenoid ring systems. Examples of
  • heteroaryl are pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, indolinyl, isoindolinyl, benzofuranyl, benzothiophenyl and benzimidazolinyl.
  • heterocyclic ring system which can be formed by R 1 and R 2 are pyrrole, pyrrolidine, thiomorpholine, indoline, azetidine, indole, isoindole, imidazole, piperidine, morpholine, benzimidazole and pyrazole.
  • Substitutents which may be present in optionally substituted aryl and heteroaryl moieties include one or more of the following: halo, hydroxy, mercapto, C 1-4 alkyl (especially methyl and ethyl), C 2-4 alkenyl
  • alkynyloxy especially propargyloxy
  • halo(C 1-4 )alkyl especially
  • pyrimidinyloxy optionally substituted aryl(C 1-4 )alkyl (especially optionally substituted benzyl, optionally substituted phenethyl and optionally substituted phenyl n-propyl) in which the alkyl moiety is optionally substituted with hydroxy, optionally substituted heteroaryl- (C 1-4 )alkyl (especially optionally substituted pyridyl- or pyrimidinyl(C 1-4 )alkyl), optionally substituted aryl(C 2-4 )alkenyl (especially
  • pyrimidinylethenyl optionally substituted aryl(C 1-4 )alkoxy (especially optionally substituted benzyloxy), optionally substituted heteroaryl(C 1-4 )- alkoxy (especially optionally substituted pyridyl- or pyrimidinyl(C 1-4 )- alkoxy), optionally substituted aryloxy(C 1-4 )alkyl (especially phenoxy- methyl), optionally substituted heteroaryloxy(C 1-4 )alkyl (especially optionally substituted pyridyloxy- or pyrimidinyloxy(C 1-4 )alkyl), acyloxy (including C 1-4 alkanoyloxy (especially acetyloxy) and benzoyloxy), cyano, thiocyanato, nitro, -NR ' R “ , -NHCOR ' , -NHCONR ' R " , -CONR ' R " , -COOR ' , -
  • R ' and R " are independently hydrogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkylthio, C 3-6 cycloalkyl, C 3-6 cycloalkyl(C 1-4 )alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C 1-4 , alkyl or C 1-4 alkoxy; when R ' and
  • R " are in CONR ' R " they can together form a 5- or 6-membered heterocyclic ring (for example a pyrrole, imidazole, pyrrolidine, piperidine or morpholine ring); or two substituents, when they are in adjacent positions on the aryl or heteroaryl ring can join to form a fused alphatic ring (especially to form a fused 6-membered carbon aliphatic ring).
  • a 5- or 6-membered heterocyclic ring for example a pyrrole, imidazole, pyrrolidine, piperidine or morpholine ring
  • two substituents when they are in adjacent positions on the aryl or heteroaryl ring can join to form a fused alphatic ring (especially to form a fused 6-membered carbon aliphatic ring).
  • Substituents which may be present in the aryl or heteroaryl rings of any of the foregoing substituents include one or more of the following: halo, hydroxy, mercapto, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 alkoxy, C 2-4 alkenyloxy, C 2-4 alkynyloxy, halo(C 1-4 )alkyl,
  • alkoxy(C 1-4 )alkyl C 3-6 cycloalkyl, C 3-6 cycloalkyl(C 1-4 )alkyl,
  • alkanoyloxy benzoyloxy, cyano, thiocyanato, nitro, -NR ' R " , -NHCOR ' ,
  • alkyl moieties and the alkyl moiety of alkoxy preferably contain from 1 to 6, more preferably from 1 to 4, carbon atoms. They can be in the form of straight or branched chains, for example methyl, ethyl, n- or isopropyl, or n-, sec-, iso- or tert-butyl.
  • Alkenyl and alkynyl moieties preferably contain from 2 to 6, more preferably from 2 to 4, carbon atoms. They can be in the form of straight or branched chains, and the alkenyl moieties, where appropriate, may have either the (E)- or (Z)-configuration. Examples are vinyl, allyl and propargyl.
  • Halogen is typically fluorine, chlorine or bromine.
  • the present invention provides a compound of formula (I) wherein R 2 is optionally substituted phenyl (especially phenyl substituted by halogen, hydroxy, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, nitro or cyano).
  • the present invention provides a compound of formula (I) wherein Z is NR 1 (wherein R 1 is hydrogen, alkyl (especially methyl or ethyl) or alkyl substituted by alkenyl or alkynyl (thus forming, for example, an allyl or propargyl group)).
  • the present invention provides a compound of formula (XI) wherein R 1 is hydrogen or C 1-4 alkyl (especially methyl or ethyl); and R 2 is phenyl optionally substituted with halogen (for example fluorine or chlorine), hydroxy, C 1-6 alkyl (such as methyl or ethyl), C 1-6 haloalkyl (for example trifluoromethyl), C 1-6 alkoxy (such as methoxy or ethoxy), C 1-6 haloalkoxy (for example trifluoromethoxy), C 1-6 alkylthio
  • halogen for example fluorine or chlorine
  • hydroxy for example fluorine or chlorine
  • C 1-6 alkyl such as methyl or ethyl
  • C 1-6 haloalkyl for example trifluoromethyl
  • C 1-6 alkoxy such as methoxy or ethoxy
  • C 1-6 haloalkoxy for example trifluoromethoxy
  • the present invention provides a compound of general formula (II), wherein n is 0 or 1; X is oxygen or sulphur; R 1 is hydrogen or C 1-4 alkyl (especially methyl or ethyl); and R 2 is phenyl(C 1-4 )alkyl
  • CH 3 O.CH CCO 2 CH 3 ;
  • n is 0 or 1;
  • X is sulphur or, preferably, oxygen;
  • Z is oxygen, sulphur or, preferably, NR 1 ;
  • R 1 is hydrogen, C 1-4 alkyl (especially methyl, ethyl or n-propyl), C 1-4 haloalkyl (especially CH 2 CHF 2 ) or C 2-4 alkynyl (especially CH 2 C ⁇ CH);
  • R 2 is phenyl (optionally substituted by halogen (especially fluorine or chlorine), nitro, cyano, C 1-4 alkyl
  • methylsulphonyl methylenedioxy or C 1-4 alkoxycarbonyl (especially methoxy- or ethoxy-carbonyl)), phenyl(C 1-4 ,)alkyl (especially benzyl), benzoyl, C 2-4 alkenyl (especially allyl), pyridinyl (optionally substituted by halogen (especially fluorine or chlorine), C 1-4 alkoxy (especially methoxy), pyrazinyl, pyrimidinyl (optionally substituted by nitro), pyridazinyl, benzothiazolyl (optionally substituted by C 1-4 alkoxy
  • indolyl especially methoxy
  • thiazolyl optionally substituted by C 1-4 alkyl (especially methyl)
  • benzoxazolyl optionally substituted by halogen (especially chlorine)
  • Table 2 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is methyl, X is oxygen, n is 11 and R 2 is as listed in Table 1
  • Table 3 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is ethyl, X is oxygen, n is 1 and R 2 is as listed in Table 1.
  • Table 4 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is n-propyl, X is oxygen, n is 1 and R 2 is as listed in Table 1.
  • Table 5 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is CH 2 CHF 2 , X is oxygen, n is 1 and R 2 is as listed in Table 1.
  • Table 6 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is hydrogen, X is sulphur, n is 1 and R 2 is as listed in
  • Table 7 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is methyl, X is sulphur, n is 1 and R 2 is as listed in Table 1
  • Table 8 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is ethyl, X is sulphur, n is 11 and R is as listed in Table 1.
  • Table 9 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is n-propyl, X is sulphur, n is 1 and R 2 is as listed in
  • Table 10 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is CH 2 CHF 2 , X is sulphur, n is 1 and R 2 is as listed in Table 1.
  • Table 11 comprises 121 compounds of general formula (II) wherein Z is oxygen, X is oxygen, n is 1 and R 2 is as llisted in Table 1
  • Table 12 comprises 121 compounds of general formula (II) wherein Z is oxygen, X is sulphur, n is 1 and R 2 is as listed in Table 1
  • Table 13 comprises 121 compounds of general formula (II) wherein Z is sulphur, X is oxygen, n is 1 and R 2 is as listed in Table 1.
  • Table 14 comprises 121 compounds of general formula (II) wherein Z is sulphur, X is sulphur, n is 1 and R 2 is as listed in Table 1.
  • Table 15 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is CH 2 C ⁇ CH, X is oxygen, n is 1 and R 2 is as listed in Table 1.
  • Table 16 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is CH 2 CsCH, X is sulphur, n is 1 and R 2 is as listed in Table I.
  • Each of Tables 17 to 32 comprises 121 compounds of general formula (II) and respectively take the values of Z, X and R 2 in Tables 1 to 16.
  • Each of Tables 33 to 64 comprises 121 compounds of general formula (IX) and respectively take the values of Z, X, R 2 and n in Tables 1 to 32.
  • Each of Tables 65 to 96 comprises 121 compounds of general formula (X) and respectively take the values of Z, X, R 2 and n in Tables 1 to 32.
  • Table 97 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is benzyl, X is oxygen ,, n is 11 and R 2 is as listed in Table 1.
  • Table 98 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is benzyl, X is sulphuir,, n is 11 and R 2 is as listed in Table 1.
  • Table 99 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is CO.CH 3 , X is oxygen, n is 1 and R 2 is as listed in Table 1.
  • Table 100 comprises 121 compounds of general formula (II) wherein Z is
  • NR 1 and R 1 is CO.CH 3 , X is sulphur, n is 1 and R 2 is as listed in Table 1.
  • Table 101 comprises 121 compounds of general formula (II) wherein Z is
  • Each of Tables 103 to 108 comprises 121 compounds of general formula (II) and respectively take the values of Z, X and R 2 in Tables 97 to 102.
  • Each of Tables 109 to 120 comprises 121 compounds of general formula (IX) and respectively take the values of Z, X, R 2 and n in Tables 97 to 108.
  • Each of Tables 121 to 132 comprises 121 compounds of general formula (X) and respectively take the values of Z, X, R 2 and n in Tables 97 to 108.
  • Table 133 comprises compounds of formula (II) wherein n is 1, X is 0 and Z is NR 1 , and R 1 and R 2 join to form a ring optionally bearing substituents.
  • a compound of formula (Ia) can be prepared by treating a chloroformate or chlorothionoformate of formula (VI), wherein V, X and n are as defined above, with a compound of formula HZR 2 , wherein Z and R 2 are as defined above, in a suitable solvent (such as toluene or dichloromethane) and in the presence of a suitable base (such as pyridine or triethylamine).
  • a suitable solvent such as toluene or dichloromethane
  • a suitable base such as pyridine or triethylamine
  • a chloroformate or chlorothionoformate of formula (VI), wherein V, X and n are as defined above can be prepared by reacting a compound of formula (III), wherein V and n are as defined above, with phosgene or thiophosgene in a suitable solvent (such as toluene or dichloromethane) in the presence of a suitable base (such as pyridine).
  • a suitable solvent such as toluene or dichloromethane
  • a suitable base such as pyridine
  • a compound of formula (Ia), wherein Z is NR 1 can alternatively be prepared from a carbonate of general formula (VII), wherein R 6 is not aliphatic (which, when V is W, is a compound of formula (I) wherein Z and X are oxygen) in a suitable solvent (such as N,N-dimethylformamide)
  • a suitable base such as sodium hydride
  • a suitable amine of type R 1 R 2 NH wherein R 1 and R 2 are as defined above.
  • a compound of formula (VII) can be prepared by treating an alcohol of formula (III) with a chloroformate of formula (VIII) in a suitable solvent (such as toluene or dichloromethane) in the presence of a suitable base (such as pyridine or 4-N,N-dimethylaminopyridine).
  • a suitable solvent such as toluene or dichloromethane
  • a suitable base such as pyridine or 4-N,N-dimethylaminopyridine.
  • Chloroformates of general formula (VIII) are known in the art or can be made by adapting literature procedures (H.E. Carter, R.L. Frank and H.W. Johnston, Org. Synth. collective volume III page 167, or W.L. Haas, E.V. Knumkalns and K. Gerzon, J.Am.Chem.Soc., (1966), 88, page 1988.)
  • a compound of formula (V) (wherein Z is NR 1 and R 1 is not hydrogen, and wherein V, n, R 2 are as defined above and X is oxygen) can be prepared by alkylating a compound of formula (IV) (which, when V is W, is a compound of formula (I)) wherein Z is NR 1 and R 1 is hydrogen, and wherein V, n, X and R 2 are as defined above, with a compound of formula R 1 L, wherein R 1 is not hydrogen and L is a leaving group (such as a halogen atom or a sulphate or sulphonate group) in the presence of a suitable base (such as potassium or sodium carbonate, potassium or sodium hydroxide or sodium hydride) in a suitable solvent (such as N,N-dimethylformamide or dimethylsulphoxide).
  • a suitable base such as potassium or sodium carbonate, potassium or sodium hydroxide or sodium hydride
  • a suitable solvent such as N,N-dimethylformamide or di
  • a compound of formula (IV) can be prepared by treating an alcohol of formula (III), wherein V and n are as defined above, with an isocyanate of formula R 2 NCO (wherein R 2 is as defined above) or an isothiocyanate of formula R 2 NCS (wherein R 2 is as defined above), in a suitable solvent (such as dichloromethane or diethyl ether) and optionally in the presence of a suitable catalyst (such as pyridine or 4-N,N-dimethylaminopyridine).
  • a suitable solvent such as dichloromethane or diethyl ether
  • a suitable catalyst such as pyridine or 4-N,N-dimethylaminopyridine
  • isocyanates of formula R 2 NCO and isothiocyanates of formula R 2 NCS are either known in the art or can be made by adapting standard literature methods [see for example, 'Advanced Organic Chemistry', Jerry March, 3rd edition (1985), page 1166, Wiley-Interscience, and references cited therein].
  • the alcohols of formula (III) are either known in the art or can be made by adapting standard literature methods (GB 2189485 or EP-A2-0398692).
  • a compound of formula (la), (IV) or (V), wherein V is W, is a compound of formula (I).
  • the present invention provides processes for preparing compounds of formula (I).
  • the present invention also relates to a process for the preparation of oxime ether amides which are useful intermediates for the preparation of compounds of formula (X).
  • the present invention provides a process for the preparation of a compound of formula (XX), wherein p is 0 or 1, the process comprising the steps:
  • the present invention provides a process for the preparation of a compound of formula (XX), wherein p is 0 or 1, the process comprising the steps:
  • the present invention provides steps (a), (b) and (c) individually or in combination.
  • the present invention provides a process for the preparation of a compound of formula (XX), wherein p is 0 or 1, the process comprising the steps:
  • Steps (a) and (b) above can be combined to give a "one-pot" process.
  • the present invention provides a process for the preparation of a compound of formula (XX), wherein p is 0 or 1, the process comprising the steps of:
  • the present invention provides a process for the preparation of a compound of formula (XXIV), wherein Y is chlorine or bromine, and p is 1, the process comprising reacting a compound of formula (XX) with a chlorinating or brominating agent.
  • the present invention provides a process for the preparation of a compound of formula (XXIV), wherein Y is chlorine or bromine and p is 1, the process comprising the steps:
  • the present invention provides a process for the preparation of a compound of formula (XXIV), wherein p is 1, and Y is chlorine or bromine, the process comprising the steps:
  • methylating agent in the presence of a base (for example an alkali metal carbonate or hydroxide or sodium hydride) to form a compound of formula (XXIII), wherein p is 1;
  • a base for example an alkali metal carbonate or hydroxide or sodium hydride
  • the present invention provides a process for the preparation of a compound of formula (XXIV), wherein p is 1 and Y is chlorine or bromine, the process comprising the steps:
  • the alkyl moiety of an alkyl nitrite is a straight or branched chain and preferably contains from 1 to 10, (for example from 4 to 8) carbon atoms, and is, for example, a tert-butyl or iso-amyl moiety.
  • Alkali metals include sodium or potassium.
  • the alkoxide moiety is especially C 1-4 alkoxide, for example
  • Methylating agents are compounds of formula CH 3 L, wherein L is a leaving group (for example halogen), and are, for example, methyl iodide or dimethyl sulphate.
  • the present invention provides a process for the preparation of a compound of formula (XX) wherein p is 1.
  • a compound of formula (XX) can be prepared by reacting a compound of formula (XXIII) with methylamine in a suitable solvent (such as methanol or ethanol).
  • a compound of formula (XXIII) can be prepared by treating a compound of formula (XXII) with a suitable base (such as sodium or potassium carbonate or hydroxide or sodium hydride) and a methylating agent (such as methyl iodide or dimethyl sulphate) in a suitable solvent (such as
  • a compound of formula (XXIII) can be prepared by treating a compound of formula (XXI) with a base (such as potassium
  • tert-butoxide in a suitable solvent (such as tert-butanol), treating this mixture with an alkyl nitrite (such as tert-butyl nitrite) and then adding a methylating agent (such as methyl iodide or dimethyl sulphate) to the reaction mixture.
  • a suitable solvent such as tert-butanol
  • a compound of formula (XXII) can be prepared by treating a compound of formula (XXI) with a base (such as sodium methoxide) in a suitble solvent (such as methanol) in the presence of an alkyl nitrite (for example
  • a compound of formula (XXII) can be prepared by treating a compound of formula (XXI) with an acid (such as hydrogen chloride) in a suitable solvent (such as methanol or ethanol) in the presence of an alkyl nitrite (for example tert-butyl nitrite).
  • an acid such as hydrogen chloride
  • a suitable solvent such as methanol or ethanol
  • a compound of formula (XXIV) wherein p is 1 can be prepared by treating a compound of formula (XX) wherein p is 1 with a suitable
  • chlorinating or brominating agent for example a combination of either carbon tetrabromide or carbon tetrachloride and triphenylphosphine
  • a suitable solvent such as 1,2-dichloroethane or tetrahydrofuran
  • the present invention provides the intermediate compounds of formulae (XX), wherein p is 0, and (XXII), (XXIII) and (XXIV) wherein p is 0 or 1.
  • 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
  • rusts on other hosts e.g. turf, rye, coffee, pears, apples, peanuts, sugar beet, vegetables and ornamental plants.
  • Erysiphe graminis (powdery mildew) 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. (including Mycosphaerella graminicola and Leptosphaeria nodorum), Pseudocercosporella herpotrichoides and Gaeumannomyces graminis on cereals (e.g. wheat, barley, rye), turf and other hosts.
  • Cercospora arachidicola and Cercosporidium personatum on peanuts and other Cercospora species on other hosts for example, sugar beet, bananas, soya beans and rice.
  • Botrytis cinerea grey mould
  • Alternaria spp. on vegetables e.g. cucumber
  • oil-seed rape e.g. apples
  • tomatoes e.g. wheat
  • other hosts e.g.
  • Venturia spp. including Venturia inaequalis (scab) on apples, pears, stone fruit, tree nuts and other hosts.
  • Cladosporium spp. on a range of hosts including cereals (e.g. wheat).
  • Phytophthora infestans on potatoes and tomatoes and other Phytophthora spp. on vegetables, strawberries, avocado, pepper, ornamentals, tobacco, cocoa and other hosts.
  • Thanatephorus cucumeris on rice and turf and other Rhizoctonia species on various hosts such as wheat and barley, vegetables, cotton and turf.
  • Colletotrichum spp. on a range of hosts including turf, coffee and vegetables.
  • Urocystis spp., Tilletia spp., and Claviceps purpurea on a variety of hosts but particularly wheat, barley, turf and maize.
  • 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.
  • pathogens on vines notably Eutypa lata, Guignardia bidwellii, Phellinus igniarus, Phomopsis viticola, Pseudopezicula tracheiphila and
  • pathogens on lumber notably Cephaloascus fragrans, Ceratocystis spp., Ophiostoma piceae, Penicillium spp., Trichoderma pseudokoningii,
  • Trichoderma viride Trichoderma harzianum, Aspergillus niger, Leptographium lindbergi and Aureobasidium pullulans.
  • Fungal vectors of viral diseases e.g. Polymyxa graminis on cereals as the vector of barley yellow mosaic virus (BYMV).
  • BYMV barley yellow mosaic virus
  • compositions show a broad range of activities against fungi in vitro.
  • compositions may be active 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
  • 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 the foliage of plants, the compounds of the invention are applied at rates of 0.1g to 10Kg, preferably 1g to 8Kg, more preferably 10g to 4Kg, of active ingredient (invention compound) per hectare.
  • the compounds of the invention are used at rates of 0.0001g (for example 0.001g or 0.05g) to 10g, 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.
  • plant as used herein includes seedlings, bushes and trees.
  • 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).
  • 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
  • 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.
  • 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 propellant, e.g. fluorotrichloromethane or dichlorodifluoromethane.
  • a propellant e.g. fluorotrichloromethane or dichlorodifluoromethane.
  • 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
  • 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.
  • 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
  • the concentrates may conveniently contain up to 95%, suitably 1-85%, for example 1-25% or 25-60%, by weight of the active ingredient.
  • aqueous preparations may contain varying amounts of the active ingredient depending upon the intended purpose, but an aqueous preparation containing 0.0001 to 10%, for example 0.005 to 10%, by weight of active ingredient may be used.
  • compositions of this invention may contain other compounds having biological activity, e.g. compounds having similar or complementary
  • An additional fungicidal compound may be present in the composition of the invention.
  • 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). Examples of fungicidal compounds which may be included in the composition of the invention are
  • chlorozolinate clozylacon
  • copper containing compounds such as copper oxychloride, copper oxyquinolate, copper sulphate and Bordeaux mixture, cycloheximide, cymoxanil, cyproconazole, cyprofuram, di-2-pyridyl
  • fenbuconazole fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fluoroimide, flutolanil, flutriafol, flusilazole, folpet, fuberidazole, furalaxyl, furconazole-cis, guazatine, hexaconazole, hydroxyisoxazole, hymexazole, imazalil, imibenconazole, ipconazole, iprobenfos, iprodione, isopropanyl butyl carbamate, isoprothiolane, kasugamycin, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, methfuroxam, metiram, metiram-zinc, metsulfovax
  • the compounds of general formula (I) can be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.
  • This Example illustrates the preparation of N-methyl-2-(2-hydroxymethylphenyl)-2-methoxyiminoacetamide.
  • This Example illustrates the preparation of N-methyl-2-(2-bromomethylphenyl)-2-methoxyiminoacetamide.
  • Carbon tetrabromide (0.33g) was added to a solution of N-methyl-2-(2--hydroxymethylphenyl)-2-methoxyiminoacetamide (0.11g) and triphenylphosphine (0.26g) in tetrahydrofuran (10ml) at 0°C.
  • the reaction mixture was stirred at 0°C for 11 ⁇ 2 hours and then at room temperature for 1 hour.
  • the reaction mixture was then poured into water and extracted three times with ethyl acetate. The combined extracts were washed with brine and dried over magnesium sulphate. The solution was then concentrated under reduced pressure to leave a gum.
  • N,N-dimethylformamide (10ml) and morpholine (70mg) was added dropwise at room temperature under an atmosphere of nitrogen.
  • the reaction mixture was stirred for 2 hours and then poured into water (50ml).
  • the products were extracted into diethyl ether (2x50ml) which was washed with water (50ml) and dried over magnesium sulphate.
  • the solvent was removed at reduced pressure to give a clear gum.
  • N,N-dimethylformamide (10ml) was added to the reaction mixture dropwise over 5 minutes and then allowed to stir at room temperature for 20 minutes.
  • a solution of methyl iodide (0.14g) in dry N,N-dimethylformamide (2ml) was added dropwise to the reaction mixture which was then left for 2 hours.
  • the solution was poured into water and extracted with diethyl ether (x3).
  • the combined organic phases were washed with water and dried with magnesium sulphate. The solvent was removed at reduced pressure to give a gum
  • the compounds were tested against a variety of foliar fungal diseases of plants.
  • the technique employed was as follows.
  • 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
  • the sprays were applied to maximum retention and the root drenches to a final concentration equivalent to approximately 40 ppm a. i. in dry soil.
  • TWEEN 20 was added to give a final concentration of 0.05% when the sprays were applied to cereals.
  • 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.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Environmental Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Indole Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
PCT/GB1992/001641 1991-09-30 1992-09-09 Fungicides WO1993007116A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
KR1019940701021A KR100229945B1 (ko) 1991-09-30 1992-09-09 살균제
AU25139/92A AU660711C (en) 1991-09-30 1992-09-09 Fungicides
DE69216632T DE69216632T2 (de) 1991-09-30 1992-09-09 Fungizide
EP92918847A EP0606251B1 (en) 1991-09-30 1992-09-09 Fungicides
JP50669493A JP3371139B2 (ja) 1991-09-30 1992-09-09 殺菌剤
US08/211,390 US6465457B1 (en) 1991-09-30 1992-09-09 Carbonate, carbamate, thiocarbonate dithiocarbonate and thiocarbomate derivatives useful as fungicides
US08/748,088 US5777162A (en) 1991-09-30 1996-11-12 Intermediates for the preparation of fungicides
KR1019997003766A KR100231635B1 (ko) 1991-09-30 1999-04-29 살균제

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB9120771.2 1991-09-30
GB919120771A GB9120771D0 (en) 1991-09-30 1991-09-30 Fungicides
GB9122875.9 1991-10-29
GB919122875A GB9122875D0 (en) 1991-10-29 1991-10-29 Chemical process

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WO1993007116A1 true WO1993007116A1 (en) 1993-04-15

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WO1994026705A1 (de) * 1993-05-17 1994-11-24 Bayer Aktiengesellschaft 3-methoxy-2-phenyl-acrylsäureester als schädlingsbekämpfungsmittel, insbesondere fungizide
US5416110A (en) * 1992-08-08 1995-05-16 Basf Aktiengesellschaft Benzyl derivatives and pesticides containing them
WO1995014009A1 (en) * 1993-11-19 1995-05-26 E.I. Du Pont De Nemours And Company Fungicidal cyclic amides
EP0656351A1 (en) * 1993-12-03 1995-06-07 Sumitomo Chemical Company, Limited Dithiocarbonimide derivatives as fungicides, insecticides, and acaricides
WO1996007635A1 (fr) * 1994-09-06 1996-03-14 Shionogi & Co., Ltd. Procede de production de derive d'alcoxyiminoacetamide
US5506254A (en) * 1994-07-06 1996-04-09 Kirstgen; Reinhard Pyrazoyly derivatives and their use
WO1996036615A1 (en) * 1995-05-16 1996-11-21 E.I. Du Pont De Nemours And Company Fungicidal cyclic amides
LT4112B (en) 1993-11-19 1997-02-25 Du Pont Fungicidal cyclic amides
EP0579071A3 (en) * 1992-07-16 1997-05-28 Basf Ag Heteroaromatic compounds and plant-protecting agents containing them
US5856560A (en) * 1994-06-10 1999-01-05 Basf Aktiengesellschaft Preparation of a-methoxyiminocarboxylic acid methylamides and intermediates therefore
US5962436A (en) * 1995-02-24 1999-10-05 E. I. Du Pont De Nemours And Company Fungicidal cyclic amides
US6022870A (en) * 1998-01-14 2000-02-08 E. I. Du Pont De Nemours And Company Fungicidal cyclic amides
WO2000058299A1 (de) * 1999-03-27 2000-10-05 Bayer Aktiengesellschaft Verfahren zur herstellung von benzofurandionoxim-derivaten
US6177463B1 (en) 1994-03-10 2001-01-23 Bayer Aktiengesellschaft Oxime derivatives and their use as pesticides
WO2001012590A1 (en) * 1999-08-13 2001-02-22 Monsanto Technology Llc Oxyme amides and hydrazone amides having fungicidal activity
WO2010089267A2 (en) 2009-02-05 2010-08-12 Basf Se Method for producing 2-halogenomethylphenyl acetic acid derivatives

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US6369083B1 (en) 1998-09-16 2002-04-09 Dow Agrosciences Llc 2-methoxyimino-2 (pyrinyloxymethyl) phenyl acetamides with polyether derivatives on the pyridine ring
US6306839B1 (en) 1998-09-16 2001-10-23 Dow Agrosciences Llc 2-methoxyimino-2-(pyridinyloxymethyl) phenyl acetamides with (derivatised) hydroxyalkyl derivatives on the pyridine ring
WO2000015637A1 (en) * 1998-09-16 2000-03-23 Dow Agrosciences Llc 2-methoxyimino -2-(pyridinyloxymethyl) phenyl acetamides with 5 membered heterocyclic rings on the pyridine ring as fungicides
WO2001044196A1 (en) 1999-12-15 2001-06-21 Dow Agrosciences, Llc Pyridine derivatives having fungicidal activity and processes to produce and use the same
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US9486441B2 (en) 2008-04-21 2016-11-08 Signum Biosciences, Inc. Compounds, compositions and methods for making the same
JP6326966B2 (ja) * 2014-05-26 2018-05-23 ユニマテック株式会社 含フッ素ウレタン（メタ）アクリレートの製造法
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CN114685313B (zh) * 2020-12-29 2024-04-05 江西天宇化工有限公司 一种肟菌酯的制备方法

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EP0307103A2 (en) * 1987-09-09 1989-03-15 Zeneca Limited Fungicides
EP0310954A1 (de) * 1987-10-07 1989-04-12 BASF Aktiengesellschaft Ortho-substituierte Carbonsäurebenzylester und Fungizide, die diese Verbindungen enthalten
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Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0579071A3 (en) * 1992-07-16 1997-05-28 Basf Ag Heteroaromatic compounds and plant-protecting agents containing them
US5416110A (en) * 1992-08-08 1995-05-16 Basf Aktiengesellschaft Benzyl derivatives and pesticides containing them
WO1994026705A1 (de) * 1993-05-17 1994-11-24 Bayer Aktiengesellschaft 3-methoxy-2-phenyl-acrylsäureester als schädlingsbekämpfungsmittel, insbesondere fungizide
US5728729A (en) * 1993-05-17 1998-03-17 Bayer Aktiengesellschaft 3-methoxy-2-phenylacrylic acid esters used as pest-control agents, especially as fungicides
RU2126392C1 (ru) * 1993-11-19 1999-02-20 Е.И.Дю Пон де Немурс энд Компани Циклические амиды или их сельскохозяйственно пригодные соли, фунгицидная композиция, способ борьбы с болезнями растений, вызванными фитопатогенными грибами
WO1995014009A1 (en) * 1993-11-19 1995-05-26 E.I. Du Pont De Nemours And Company Fungicidal cyclic amides
US5977149A (en) * 1993-11-19 1999-11-02 E. I. Du Pont De Nemours And Company Dihydrotriazole compounds and their use for controlling fungal plant diseases
LT4112B (en) 1993-11-19 1997-02-25 Du Pont Fungicidal cyclic amides
US5747516A (en) * 1993-11-19 1998-05-05 E. I. Du Pont De Nemours And Company Dihydroazole compounds and their use for controlling fungal plant diseases
EP0656351A1 (en) * 1993-12-03 1995-06-07 Sumitomo Chemical Company, Limited Dithiocarbonimide derivatives as fungicides, insecticides, and acaricides
US5563159A (en) * 1993-12-03 1996-10-08 Sumitomo Chemical Company, Limited Dithiocarbonimide derivatives useful as acaricidal, fungicidal, and insecticidal agents
US6177463B1 (en) 1994-03-10 2001-01-23 Bayer Aktiengesellschaft Oxime derivatives and their use as pesticides
US5856560A (en) * 1994-06-10 1999-01-05 Basf Aktiengesellschaft Preparation of a-methoxyiminocarboxylic acid methylamides and intermediates therefore
US5506254A (en) * 1994-07-06 1996-04-09 Kirstgen; Reinhard Pyrazoyly derivatives and their use
US6037495A (en) * 1994-09-06 2000-03-14 Shinonogi & Co., Ltd. Process for producing alkoxyiminoacetamide derivatives
WO1996007635A1 (fr) * 1994-09-06 1996-03-14 Shionogi & Co., Ltd. Procede de production de derive d'alcoxyiminoacetamide
US5962436A (en) * 1995-02-24 1999-10-05 E. I. Du Pont De Nemours And Company Fungicidal cyclic amides
WO1996036615A1 (en) * 1995-05-16 1996-11-21 E.I. Du Pont De Nemours And Company Fungicidal cyclic amides
US6022870A (en) * 1998-01-14 2000-02-08 E. I. Du Pont De Nemours And Company Fungicidal cyclic amides
WO2000058299A1 (de) * 1999-03-27 2000-10-05 Bayer Aktiengesellschaft Verfahren zur herstellung von benzofurandionoxim-derivaten
US6462205B1 (en) 1999-03-27 2002-10-08 Bayer Aktiengesellscahft Method of preparing benzofurandione oxime derivatives
WO2001012590A1 (en) * 1999-08-13 2001-02-22 Monsanto Technology Llc Oxyme amides and hydrazone amides having fungicidal activity
US6297271B1 (en) 1999-08-13 2001-10-02 Monsanto Technology Llc Oxime amides and hydrazone amides having fungicidal activity
US6359156B1 (en) 1999-08-13 2002-03-19 Monsanto Technology Llc Oxime amides and hydrazone amides having fungicidal activity
WO2010089267A2 (en) 2009-02-05 2010-08-12 Basf Se Method for producing 2-halogenomethylphenyl acetic acid derivatives
WO2010089267A3 (en) * 2009-02-05 2011-10-13 Basf Se Method for producing 2-halogenomethylphenyl acetic acid derivatives
CN102438980A (zh) * 2009-02-05 2012-05-02 巴斯夫欧洲公司 制备2-卤代甲基苯基乙酸衍生物的方法
US8575366B2 (en) 2009-02-05 2013-11-05 Basf Se Method for producing 2-halogenomethylphenyl acetic acid derivatives

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GB9218541D0 (en) 1992-10-14
JPH07502985A (ja) 1995-03-30
US5939563A (en) 1999-08-17
EP0606251A1 (en) 1994-07-20
DE69230185T2 (de) 2000-04-27
ATE147374T1 (de) 1997-01-15
TW221366B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1994-03-01
EP0711751A1 (en) 1996-05-15
EP0606251B1 (en) 1997-01-08
ES2138252T3 (es) 2000-01-01
NZ270672A (en) 1996-01-26
US5585513A (en) 1996-12-17
DK0711751T3 (da) 2000-04-10
AU2513992A (en) 1993-05-03
US5777162A (en) 1998-07-07
AU660711B2 (en) 1995-07-06
EP0711751B1 (en) 1999-10-20
DE69216632D1 (de) 1997-02-20
DE69216632T2 (de) 1997-05-22
KR100229945B1 (ko) 1999-11-15
NZ244266A (en) 1996-01-26
ATE185794T1 (de) 1999-11-15
KR100231635B1 (ko) 2000-03-15
US6465457B1 (en) 2002-10-15
JP3371139B2 (ja) 2003-01-27
DE69230185D1 (de) 1999-11-25

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