[go: up one dir, main page]

WO1991016299A1 - Carbamates d'oxime fongicides - Google Patents

Carbamates d'oxime fongicides Download PDF

Info

Publication number
WO1991016299A1
WO1991016299A1 PCT/US1990/005998 US9005998W WO9116299A1 WO 1991016299 A1 WO1991016299 A1 WO 1991016299A1 US 9005998 W US9005998 W US 9005998W WO 9116299 A1 WO9116299 A1 WO 9116299A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
phenyl
halogen
alkyl
dimethylamino
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US1990/005998
Other languages
English (en)
Inventor
Stephen Lee Hartzell
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from PCT/US1990/002124 external-priority patent/WO1990012784A1/fr
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of WO1991016299A1 publication Critical patent/WO1991016299A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
    • 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
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/02—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by halogen atoms
    • 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
    • C07C271/60—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups having oxygen atoms of carbamate groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/76—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/77—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/78—Halides of sulfonic acids
    • C07C309/86—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/89—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
    • C07C311/47—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • 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
    • C07C317/28—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 acyclic carbon atoms of the carbon skeleton
    • 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
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • 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
    • C07C323/10—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 singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—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 singly-bound oxygen atoms 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
    • C07C323/19—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 singly-bound oxygen atoms 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 with singly-bound oxygen atoms bound to acyclic carbon atoms of the carbon skeleton
    • 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
    • C07C323/39—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 at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—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
    • C07C323/50—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 carboxyl groups bound to the same carbon skeleton
    • C07C323/51—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • C07C323/50—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 carboxyl groups bound to the same carbon skeleton
    • C07C323/62—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 carboxyl 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C325/00—Thioaldehydes; Thioketones; Thioquinones; Oxides thereof
    • C07C325/02—Thioketones; Oxides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/38—Amides of thiocarboxylic acids
    • C07C327/40—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • 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
    • C07C329/06—Esters of monothiocarbonic acids having sulfur atoms of thiocarbonic groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/02—Thiocyanates
    • C07C331/12—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07C333/12—Monothiocarbamic acids; Derivatives thereof having nitrogen atoms of thiocarbamic groups bound to other hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/14—Compounds containing a carbon atom having four bonds to hetero atoms with a double bond to one hetero atom and at least one bond to a sulfur atom further doubly-bound to oxygen atoms
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D295/18—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 carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D295/18—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 carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/194—Radicals derived from thio- or thiono carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
    • C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
    • 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/095—Compounds containing the structure P(=O)-O-acyl, P(=O)-O-heteroatom, P(=O)-O-CN
    • C07F9/097—Compounds containing the structure P(=O)-O-N
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Definitions

  • Hubele CH 66-16,259 claims compounds of Formulaii as fungicides for crop protection.
  • EP 293 667 A as fungicides for crop protection.
  • fungus comprising the application of an effective amount of a compound of Formula I to the locus to be protected,
  • Q and Q 1 are independently oxygen, NR 8 or a
  • L is O or S
  • n 0, 1 or 2;
  • R is C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20
  • 0-1 groups selected from -CH 2 (CH 2 ) p CH 2 -, -O(CH 2 ) p CH 2 -, -S(CH 2 ) p CH 2 -, -O(CH 2 ) p O,
  • SO 2 NR 14 R 15 2-, 3-, or 4-pyridyl, or phenyl substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl, dimethylamino or amino;
  • R can additionally be a heterocyclic ring
  • R can additionally be a heteroaromatic or fused heteroaromatic ring system, ring-carbon- linked to the carbonyl group when A is
  • heteroatoms comprise 1-3 nitrogen atoms, or
  • R 1 is C 1 -C 20 alkyl, C 3 -C 20 alkenyl, C 3 -C 20
  • alkynyl or C 1 -C 8 alkyl, C 3 -C 8 alkenyl or
  • alkoxyalkyl C 1 -C 6 alkylthio, C 3 -C 6
  • cycloalkyl CN or with a phenyl group substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl, dimethylamino, amino, phenyl or phenoxy; provided that, if R 1 is alkenyl or alkynyl, the unsaturated carbons are not bonded directly to the oxygen atom of
  • R 2 and R 3 are independently selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, benzyl or phenyl; R 4 is H or C 1 -C 4 alkyl;
  • R 5 is C 1 -C 4 alkyl substituted with 0-3 halogen, or R 5 is a phenyl group substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl,
  • R 6 is H, C 1 -C 4 alkyl substituted with 0-3
  • halogen or R6 is a phenyl group substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S,
  • R 7 is H or C 1 -C 4 alkyl substituted with 0-3 halogen, or R 6 and R 7 taken together with the nitrogen atom to which they are attached can be piperidine, pyrrolidine or
  • R 8 is H or C 2 -C 4 alkyl
  • R 9 is C 1 -C 8 alkyl substituted with 0-3 halogen, or R 9 is phenyl substituted with 0-2
  • R 10 and R 11 are independently H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkoxyalkyl, or benzyl or phenyl, said benzyl or phenyl rings being substituted with 0-2 halogen, CH 3 , CF 3 , CH 3 O or CN; or R 10 and R 11 , taken together with the nitrogen atom to which they are attached, can be azetidine,
  • R 12 is C 1 -C 12 alkyl or haloalkyl, or benzyl
  • R 13 is C 1 -C 4 alkyl, haloalkyl or C 2 -C 4
  • alkoxyalkyl C 3 -C 4 alkenyl, haloalkenyl, alkynyl or haloalkynyl, or benzyl or phenyl, said benzyl or phenyl rings being
  • R 14 is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, or
  • R 16 is C 1 -C 6 alkyl, C 3 -C 4 alkenyl, or benzyl substituted with 0-2 halogen, methyl, trifluoromethyl, nitro or methoxy; and p is 1 or 2.
  • Q and Q 1 are independently oxygen, NR 8 or a
  • L is O or S
  • n 0, 1 or 2;
  • R is C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20
  • carbocyclic aromatic ring systems wherein said rings are substituted with 0-4 halogen, and 0-1 groups selected from -CH 2 (CH 2 ) p CH 2 -, -O(CH 2 ) p CH 2 -, -S(CH 2 ) p CH 2 -, -O(CH 2 ) p O,
  • SO 2 NR 14 R 15 2-, 3-, or 4-pyridyl, or phenyl substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl, dimethylamino or amino;
  • R can additionally be a heterocyclic ring
  • R can additionally be a heteroaromatic or fused heteroaromatic ring system, ring-carbon- linked to the carbonyl group when A is
  • heteroatoms comprise 1-3 nitrogen atoms, or
  • R 1 is C 1 -C 20 alkyl, C 3 -C 20 alkenyl, C 3 -C 20
  • alkynyl or C 1 -C 8 alkyl, C 3 -C 8 alkenyl or
  • alkoxyalkyl C 1 -C 6 alkylthio, C 3 -C 6
  • cycloalkyl CN or with a phenyl group substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl, dimethylamino, amino, phenyl or phenoxy; provided that, if R 1 is alkenyl or alkynyl, the unsaturated carbons are not bonded directly to the oxygen atom of R 2 and R 3 are independently selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, benzyl or phenyl; R 4 is H or C 1 -C 4 alkyl;
  • R 5 is C 1 -C 4 alkyl substituted with 0-3 halogen, or R 5 is a phenyl group substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl,
  • R 6 is H, C 1 -C 4 alkyl substituted with 0-3
  • halogen or R6 is a phenyl group substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S,
  • R 7 is H or C 1 -C 4 alkyl substituted with 0-3 halogen, or R 6 and R 7 taken together with the nitrogen atom to which they are attached can be piperidine, pyrrolidine or
  • R 8 is H or C 1 -C 4 alkyl
  • R 9 is C 1 -C 8 alkyl substituted with 0-3 halogen, or R 9 is phenyl substituted with 0-2
  • R 10 and R 11 are independently H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkoxyalkyl, or benzyl or phenyl, said benzyl or phenyl rings being substituted with 0-2 halogen, CH 3 , CF 3 , CH 3 O or CN; or R 10 and R 11 , taken together with the nitrogen atom to which they are attached, can be azetidine,
  • R 12 is C 1 -C 12 alkyl or haloalkyl, or benzyl
  • R 13 is C 1 -C 4 alkyl, haloalkyl or C 2 -C 4
  • alkoxyalkyl C 3 -C 4 alkenyl, haloalkenyl, alkynyl or haloalkynyl, or benzyl or phenyl, said benzyl or phenyl rings being
  • R 14 is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, or
  • R 16 is C 1 -C 6 alkyl, C 3 -C 4 alkenyl, or benzyl substituted with 0-2 halogen, methyl, trifluoromethyl, nitro or methoxy; and p is 1 or 2;
  • R is C 1 -C 2 alkyl substituted with a phenyl
  • phenyl group being substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S,
  • R is a phenyl or naphthyl ring, substituted
  • R 10 and R 11 are independently H, C 1 -C 4 alkyl, haloalkyl or benzyl substituted with 0-2 halogen, CH 3 , CF 3 , CH 3 O or CN; or R 10 and R 11 , taken together with the nitrogen atom to which they are attached, can be piperidine, pyrrolidine or morpholine, each substituted with 0-2 methyl groups; and
  • X is Cl. 4.
  • Particularly preferred for ease of synthesis and/or fungicidal activity are compounds of Preferred 3 wherein:
  • R is C 1 -C 2 alkyl substituted with a phenyl
  • phenyl group being substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S,
  • R is a substituted phenyl or naphthyl ring
  • substituent is selected from: 0-3 halogen and 0-2 CH 3 , CF 3 , CH 3 O, CN, CH 3 S, methylsulfonyl, dimethylamino, amino, phenyl or phenoxy; and
  • X is Cl. Also particularly preferred for ease of
  • R is C 1 -C 2 alkyl substituted with a phenyl
  • phenyl group being substituted with 0-3 halogen and 0-2 groups selected from CH 3 , CF 3 , CH 3 O, CN, CH 3 S,
  • R is a substituted phenyl or naphthyl ring
  • the compounds of Formula I can be prepared from compounds of Formula III and an appropriate
  • electrophilic reagent of Formula II in an inert solvent with or without a base used either as a catalyst or acid scavenger Suitable solvents include polar aprotic solvents such as acetonitrile, dimethylformamide, or dimethylsulfoxide; ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; ketones such as acetone or 2-butanone;
  • hydrocarbons such as toluene or benzene
  • halocarbons such as dichloromethane or chloroform.
  • Appropriate bases include alkali metal alkoxides such as sodium methoxide or potassium tert-butoxide, inorganic bases such as sodium hydride or potassium carbonate, or tertiary amines such as triethylamine, pyridine, 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU), or triethylenediamine (DABCO).
  • alkali metal alkoxides such as sodium methoxide or potassium tert-butoxide
  • inorganic bases such as sodium hydride or potassium carbonate
  • tertiary amines such as triethylamine, pyridine, 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU), or triethylenediamine (DABCO).
  • temperature can vary between 0°C and 150° for periods of 1 to 72 hours depending on the choice of base, solvent, temperature, and substrates.
  • a novel method of preparation of compounds of Formula Ia-c comprises sequential preparation of the novel chloroformate Ig by reaction of compounds of Formula III with phosgene in the presence of organic bases such as N,N-diethylaniline and pyridine,
  • a suitable acid scavenger such as N,N-diethylaniline, pyridine or triethylamine.
  • Compounds of Formula Id can be prepared from compounds of Formula III and a carboxylic acid Ilg in the presence of a coupling auxiliary reagent such as, but not limited to, N,N-dicyclohexyl carbodiimide (DCC) or 2,2'-dipyridyldisulfide (DPDS).
  • a coupling auxiliary reagent such as, but not limited to, N,N-dicyclohexyl carbodiimide (DCC) or 2,2'-dipyridyldisulfide (DPDS).
  • hydroximoyl chlorides or bromides of Formulas la, b, d, e, f can be prepared from the corresponding aldoximes of Formula IV with halogens (see H. Metzger, Heinrich Oximen, Houben-Weyl, Methoden der organische Chemie, E.
  • Hydroximoyl chlorides of Formula lb and I d can be prepared by the reaction of nitro compounds of
  • the thiocarboxamide and thioketone compounds of Formula I can be prepared from the carboxamide or ketone compounds, respectively, of Formula I by methods described elsewhere (see S. Scheibye,
  • the ⁇ -chloroaldoximes of Formula III can be prepared by treating amines of Formula V with sodium nitrite and hydrochloric acid (see G. S. Skinner, J. Am. Chem. Soc., 1924, 46,731).
  • ⁇ -chloroaldoximes of Formula III can also be prepared from aldoximes of Formula VI by treatment with N-chlorosuccinimide (see K. E. Larsen and K. B. G. Torsell, Tetrahedron, 1984, 40, 2985) or
  • Some ⁇ -haloaldoximes of Formula III may be prepared from amide oximes VII by treatment with sodium nitrite in hydrohalic acid solution (see
  • ⁇ -haloaldoximes of Formula III can be prepared from trihalomethyl compounds of Formula VIII by basic hydrolysis in the presence of hydroxylamine (see A. P. Kozikowski and M. Adamczyk, J. Org. Chem., 1983, 48 , 366).
  • the ⁇ -haloaldoximes of Formula III can be prepared by the reaction of nitrile N-oxides of
  • nitrile N-oxides of Formula IX can be prepared by several methods well known in the chemical art (for a summary of methods, see T. Shimizu,
  • the carobxamide and carboxylic acid ester compounds of Formula III can be prepared by the
  • the thiocarboxamide compounds of Formula III can be prepared from the trihalothioacetamides of Formula XI which are obained from the haloimmonium chlorides of Formula XII. See W. Walter and K. -D. Bode, Angew,
  • the ketone compounds of Formula III can be prepared from halomethyl ketones of Formula XIII by treatment with an alkyl nitrite and hydrochloric acid (see N. Levin and W. H. Hartung, Oro. Synthesis, 1944, 24 , 25).
  • the ketone compounds of Formula III can also be prepared from halomethyl ketones of Formula XIII by treatment with dimethyl sulfide to afford compounds of Formula XIV, which are then treated with sodium nitrite and hydrochloric acid (see Y. Ofsuji,
  • the ketone compounds of Formula III can be prepared from ⁇ -ketosulfoxides of Formula XV by treatment with sodium nitrite in hydrohalic acid solution (see Y. Otsuji, Y. Tsujii, A. Yoshida and E. Imoto, Bull. Chem. Soc. Japan, 1971, 44, 219).
  • the ketone compounds of Formula III can also be prepared from compounds of Formula VI by treatment with chlorine gas (see G. Casnati and A. Ricca, Tet. Letters. 1967, 327 and Y. H. Chiang, J. Org. Chem., 1971, 36, 2146).
  • the thioalkyl and thioaryl compounds of Formula III can be prepared from dihaloformaldoxime XVI (see D. Chiarino, M. Napoletano and A. Sala, Synth. Comm., 1988, 18, 1171 and D. M. Vyas, Y. Chiang and
  • the sulfonylcarbohydroximoyl chlorides of Formula III can be prepared from
  • compounds of Formula I are O-substituted oximes which can be of either the syn or anti form.
  • the scope of the specification referring to compounds of Formula I includes both stereoisomeric oxime forms either as a specific steroisomer, a mixture of stereoisomers, or as any reciprocal mixture ratio of the two
  • N,N-dimethylformamide was added 2-biphenylcarboxylic acid (3.42 g), followed by N,N'-dicyclohexyl- carbodiimide (3.56 g). The next day the mixture was filtered, the filtrate diluted with ice water, and the mixture extracted with ethyl acetate. The ethyl acetate solution was washed with water, IN HCl, water, saturated sodium bicarbonate solution, and saturated brine, dried (MgSO 4 ), filtered and the filtrate evaporated to a colorless oil. Chromatography of the oil on silica gel with 25% EtOAc in CHCl 3 provided a solid, on evaporation of eluent, which was
  • chlorothiolformate (2.23 g) was added to the solution at room temperature.
  • the solution was cooled to 10°C, then triethylamine was added to the solution.
  • the reaction was allowed to warm to room temperature.
  • the oil was dissolved in BuCl ( ⁇ 100 mL), diluted to the cloud point with hexane, and restripped to an oil, which solidified to a light-orange solid under a nitrogen stream.
  • the solid was dissolved in 100 mL of hot cyclohexane, and the supernatant decanted from a little insoluble oil; the oil was extracted with 25 mL of hot cyclohexane, and the combined, hot, turbid extracts treated with MgSO 4 (6 g) to soak up some of the oil present, and filtered.
  • N-(((3,5-dichlorophenyl)amino-carbonyloxy))-2-dimethyl- amino)-2-oxo dissolved in 50 mL of CH 2 Cl 2 was added 0.35 g of Lawesson's reagent. The yellow solution was stirred for four days at room temperature. After concentration to one-half the original volume, the solution was flash chromatographed, eluting with 25% ethyl acetate/hexanes. The product had a Rf of 0.3 and 0.27 g (52%) of yellow solid were obtained; m.p. 156-157°C.
  • the above was prepared by dissolving 23.7 mL of piperidine in 100 mL H 2 O. After cooling to 3°C, diketene was added dropwise over 10 minutes, causing an exotherm to 32°C. The mixture was stirred while cooling to 5°C for 10 minutes. 16.6 g of sodium nitrite was added in three portions, keeping the temperature less than 10°C whereupon the mixture was stirred for 30 minutes. Under a nitrogen blanket, 21 mL of concentrated HCl was added portionwise over 10 minutes, keeping the temperature ⁇ 35°C. After all of the acid had been added, the suspension was cooled to 2°C and stirred at that temperature for 45 minutes. Vacuum filtration, followed by a cold water wash yielded an off-white solid which was partially dried by filtration suction. The material was used without further characterization in the above step.
  • Y of (Ii) is the same as X of (I), W-Z-A 1 of (Ii) is the same as A of (I).
  • TMS tetramethylsilane
  • Peak multiplicities are listed using abbreviations familiar to those skilled in the art, singlet (s), doublet (d), triplet (t), quartet (q), and multiplet (m).
  • the compounds of this invention will generally be used in formulation with a liquid or solid diluent or with an organic solvent.
  • Useful formulations of the compounds of Formula I can be prepared in
  • formulations can be extended in suitable media and used at spray volumes of from about one to several hundred liters per hectare. High strength
  • compositions are primarily used as intermediates for further formulation.
  • the formulations broadly,
  • surfactant(s) and b) about 5% to 99% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following
  • compositions Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are
  • Emulsifiers Annual MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc. Preferably, ingredients should be approved by the U.S. Environmental Protection
  • compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Water dispersible granules may be produced by agglomerating a fine powder composition (see, for example, B. Cross and H. Scher, "Pesticide Formulations", ACS Symposium Series 371, American Chemical Society, Washington, D. C., 1988, pp.
  • Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent 3,060,084).
  • Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning,
  • the ingredients are blended, hammermilled, re-blended and packaged.
  • the ingredients are blended and ground in a hammermill to produce a high strength
  • N-methyl-2-pyrrolidone 70% The ingredients are combined and stirred to produce a solution, which can be used for low volume applications.
  • the compounds of this invention are useful as plant disease control agents. They provide control of diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete and
  • Oomycete classes are effective in controlling a broad spectrum of plant diseases, particularly foliate pathogens of ornamental, vegetable, field, cereal and fruit crops. These pathogens included, Plasmopora viticolgi/ Phytpphthorg infestans, Peronospora
  • the compounds of this invention can be mixed with fungicides, bactericides, acaricides,
  • nematicides nematicides, insecticides, or other biologically active compounds in order to achieve desired results with a minimum expenditure of time, effort and material.
  • Suitable agents of this type are well-known to those skilled in the art. Some are listed below:
  • pre-infection to the portion of the plant to be protected such as the roots, stems, foliage, fruit, seeds, tubers or bulbs.
  • the compound may also be applied to the seed, to protect the seed and seedling.
  • Rates of application for these compounds can be influenced by many factors of the environment and should be determined under actual use conditions.
  • Foliage can normally be protected when treated at a rate of from less than 10 g/ha to 10,000 g/ha of active ingredient. Seed and seedlings can normally be protected when seed is treated at a rate of from .1 to 10 g per kilogram of seed.
  • test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on apple seedlings. The following day the seedlings were inoculated with a spore suspension of Venturia inaegualis (the causal agent of apple scab) and incubated in a saturated atmosphere at 20°C for 24 hr, and then moved to a growth chamber at 22°C for 11 days, after which disease ratings were made.
  • a spore suspension of Venturia inaegualis the causal agent of apple scab
  • Example B The test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on peanut seedlings.
  • Trem 014 polyhydric alcohol esters
  • test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on wheat seedlings. The following day the seedlings were inoculated with a spore suspension of Puccinia recondita (the causal agent of wheat leaf rust) and incubated in a saturated atmosphere at 20°C for 24 hr, and then moved to a growth chamber at 20°C for 6 days, after which disease ratings were made.
  • Puccinia recondita the causal agent of wheat leaf rust
  • Example D The test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on rice seedlings.
  • Trem 014 polyhydric alcohol esters
  • test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on tomato seedlings. The following day the seedlings were inoculated with a spore suspension of Phytophthora infestans (the causal agent of potato and tomato late blight) and incubated in a saturated atmosphere at 20°C for 24 hr, and then moved to a growth chamber at 20°C for 5 days, after which disease ratings were made.
  • Trem 014 polyhydric alcohol esters
  • Example F The test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on grape seedlings.
  • Trem 014 polyhydric alcohol esters
  • the seedlings were inoculated with a spore suspension of Plasmopara viticola (the causal agent of grape downy mildew) and incubated in a saturated atmosphere at 20°C for 24 hr, moved to a growth chamber at 20°C for 6 days, and then incubated in a saturated atmosphere at 20°C for 24 hr, after which disease ratings were made.
  • Plasmopara viticola the causal agent of grape downy mildew
  • test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on cucumber
  • Example H The test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on sugar beet
  • Example I The test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 1000 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on tobacco seedlings. The following day the seedlings were inoculated with a spore suspension of Peronospora tabacina (the causal agent of tobacco blue mold) and incubated in a
  • Example J The test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on cucumber
  • Pseudoperonospora cubensis the causal agent of cucumber downy mildew
  • incubated in a saturated atmosphere at 20°C for 24 hr moved to a growth chamber at 20°C for 6 days, and then incubated in a saturated atmosphere at 20°C for 24 hr, after which disease ratings were made.
  • Results for Examples A to J are given in Tables A, B and C.
  • a rating of 100 indicates 100% disease control and a rating of 0 indicates no disease control(relative to the carrier sprayed controls).
  • NT indicates that no test was performed.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Procédé de lutte contre les maladies de plantes, tout particulièrement contre les champignons, utilisant des composés de la formule (I) et de nouveaux composés appartenant à la classe (I): dans laquelle A représente C(=O)OR1, C(=O)SR1, P(=O)QR2Q1R3; C(=O)NHR, SO¿2R?5, SO2NR6R7; Q et Q1 représentent indépendemment oxygène NR8 ou une liaison directe; X représente C1 ou Br; à condition que lorsque X représente Br, A représente C(=O)R; G représente C(=L)R9, C(=L)NR10R11, C(=O)OR12, CN, SO¿2?NR?10R11¿, ou SO¿mR?13; L représente O ou S; m représente 0, 1 ou 2; et R et R¿1¿ à R9 représentent les composants définis dans la présente invention.
PCT/US1990/005998 1989-04-25 1990-10-24 Carbamates d'oxime fongicides Ceased WO1991016299A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US34287689A 1989-04-25 1989-04-25
US39826689A 1989-08-24 1989-08-24
AUPCT/US90/02124 1990-04-24
PCT/US1990/002124 WO1990012784A1 (fr) 1989-04-25 1990-04-24 Carbamates d'oxyme fongicides

Publications (1)

Publication Number Publication Date
WO1991016299A1 true WO1991016299A1 (fr) 1991-10-31

Family

ID=27376421

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1990/005998 Ceased WO1991016299A1 (fr) 1989-04-25 1990-10-24 Carbamates d'oxime fongicides

Country Status (1)

Country Link
WO (1) WO1991016299A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0672654A1 (fr) * 1994-03-19 1995-09-20 Basf Aktiengesellschaft Amides carbamoyleoxime carboxyliques fongicides

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1806120A1 (de) * 1967-10-31 1969-05-14 Agripat Sa Neue Carbamoyloxime,Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekaempfung von Schaedlingen
DE2134332A1 (de) * 1970-07-10 1972-01-13 Roussel Uclaf, Paris Neue substituierte Oxime und Ver fahren zu deren Herstellung
FR2327984A1 (fr) * 1973-03-15 1977-05-13 Roussel Uclaf Nouveaux derives substitues de l'o chlore o isonitrose acetophenone, procede de preparation et application comme pesticides
DE2621102A1 (de) * 1976-05-10 1977-11-24 Schering Ag Propan-1,2-diondioxime, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung
GB2028797A (en) * 1978-08-31 1980-03-12 Ciba Geigy Ag Oxime carbamates and oxime carbonates for the protection of cultivated crops
EP0010588A2 (fr) * 1978-08-28 1980-05-14 Ciba-Geigy Ag Composés d'oxime contenant du soufre et leur utilisation pour la protection des plantes cultivées
US4272453A (en) * 1980-07-24 1981-06-09 Morton-Norwich Products, Inc. 1-Chloro-1-p-methoxybenzoylformaldoxime-N-methylcarbamate

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1806120A1 (de) * 1967-10-31 1969-05-14 Agripat Sa Neue Carbamoyloxime,Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekaempfung von Schaedlingen
DE2134332A1 (de) * 1970-07-10 1972-01-13 Roussel Uclaf, Paris Neue substituierte Oxime und Ver fahren zu deren Herstellung
FR2327984A1 (fr) * 1973-03-15 1977-05-13 Roussel Uclaf Nouveaux derives substitues de l'o chlore o isonitrose acetophenone, procede de preparation et application comme pesticides
DE2621102A1 (de) * 1976-05-10 1977-11-24 Schering Ag Propan-1,2-diondioxime, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung
EP0010588A2 (fr) * 1978-08-28 1980-05-14 Ciba-Geigy Ag Composés d'oxime contenant du soufre et leur utilisation pour la protection des plantes cultivées
GB2028797A (en) * 1978-08-31 1980-03-12 Ciba Geigy Ag Oxime carbamates and oxime carbonates for the protection of cultivated crops
US4272453A (en) * 1980-07-24 1981-06-09 Morton-Norwich Products, Inc. 1-Chloro-1-p-methoxybenzoylformaldoxime-N-methylcarbamate

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Bull. Chem. Soc. Japan, volume 59, September 1986, The Chemical Society of Japan, T. Shumizu et al.: "A convenient preparative method of nitrile oxides by the dehydration of primary nitro compounds with ethyl chloroformate or benzenesulfonyl chloride in the presence of triethylamine" pages 2827-2831 *
Chemical Abstracts , volume 71, 1969, (Columbus, Ohio, US), Y.L. Kruglyak et al.: "Phosphorylated oximes. VI. Reaction of salts of nitro carboxylic acid esters with diethyl chloroposphite", see page 283 *
Chemical Abstracts, volume 81, 1974, (Columbus, Ohio, US), H. Brachwitz: "Hydroximic acid derivatives. VIII. Reduction of hydroximic acid derivatives", see page 491 *
Chemical Pharm. Bull., volume 28, no. 11, 1980, K. Harafa et al.: "Synthesis of five-membered heterocycles containing a nitrogen-oxygen bond via o-acylation of aliphatic nitro compounds", pages 3296-3303 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0672654A1 (fr) * 1994-03-19 1995-09-20 Basf Aktiengesellschaft Amides carbamoyleoxime carboxyliques fongicides

Similar Documents

Publication Publication Date Title
RU2092051C1 (ru) Производные оксазолидинона, фунгицидная композиция и способ борьбы с грибковыми заболеваниями
PL174704B1 (pl) Nowe 4(3H)-chinazolinony i środek grzybobójczy do zwalczania mączniaka pszenicy
US4957933A (en) Fungicidal oxazolidinones
US5328915A (en) Arthropodicidal amidrazone ureas
WO1992019615A2 (fr) Pyrazoles, pyrazolines et tetrahydropyridazines fongicides
US5223523A (en) Fungicidal oxazolidinones
WO1990012784A1 (fr) Carbamates d&#39;oxyme fongicides
EP0359400A1 (fr) Dérivés de benzodioxane amine fongicide
WO1991016299A1 (fr) Carbamates d&#39;oxime fongicides
US5356908A (en) Fungicidal oxazolidinones
EP0937051A1 (fr) Amides cycliques fongicides
EP0533734A1 (fr) Iminooxazolidinones fongicides
WO1992003050A1 (fr) Esters fongicides de sulfoneoxime
US4210668A (en) Insecticidal carbamates
WO1992002491A1 (fr) Nouveaux derives de (chlorure d&#39;hydroximidoyl)-bis utilises comme fongicides agricoles
EP0636121A1 (fr) Sulfonates de pyrazole arthropodicides
WO1991015480A1 (fr) Oxazolidinones fongicides
EP0007156B1 (fr) Carbamates, compositions les contenant, leur utilisation comme insècticides et nématocides ainsi qu&#39;un procédé de leur préparation
EP0503798A1 (fr) 4-Thioxooxazolidin-2-ones et 4-iminooxazoliden-2-ones fongicides
US5128348A (en) Bicyclo(3.1.0)hexane amines and bicyclo(4.1.0)-heptane amines as agricultural fungicides
WO1993021150A2 (fr) Arlylsulfonates arthropodicides
WO1992004318A1 (fr) Carbonates d&#39;oxime utilises comme fongicides
WO1992010475A1 (fr) Nouvelles amidines et guanidines heterocycliques utilisees comme fongicides pour plantes
USH1829H (en) Fungicidal fused bicyclic pyrimidinones
WO1992011762A1 (fr) Hydroxypyranones fongicides

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP KR