FI92392C - Akrylaattifungisidit ja niiden käyttö - Google Patents

Akrylaattifungisidit ja niiden käyttö Download PDF

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Publication number
FI92392C
FI92392C FI883297A FI883297A FI92392C FI 92392 C FI92392 C FI 92392C FI 883297 A FI883297 A FI 883297A FI 883297 A FI883297 A FI 883297A FI 92392 C FI92392 C FI 92392C
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Finland
Prior art keywords
compound
compounds
methyl
year
substituted
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FI883297A
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English (en)
Swedish (sv)
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FI92392B (fi
FI883297A0 (fi
FI883297A (fi
Inventor
Geoffrey Ross Cliff
Ian Christopher Richards
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Schering Agrochemicals Ltd
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26292482&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=FI92392(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from GB878716392A external-priority patent/GB8716392D0/en
Priority claimed from GB888807388A external-priority patent/GB8807388D0/en
Application filed by Schering Agrochemicals Ltd filed Critical Schering Agrochemicals Ltd
Publication of FI883297A0 publication Critical patent/FI883297A0/fi
Publication of FI883297A publication Critical patent/FI883297A/fi
Publication of FI92392B publication Critical patent/FI92392B/fi
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    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • 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
    • A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • 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
    • A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
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    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
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    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
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    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
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    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • 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
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    • 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
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    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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    • C07D231/14—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 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
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    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
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    • C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
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    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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    • 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
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    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
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    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
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    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
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    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having 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
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    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
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    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings 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
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    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
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    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/82—Nitrogen atoms
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    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
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    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
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    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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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
    • C07D295/21—Radicals derived from sulfur analogues of carbonic acid
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    • 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
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    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
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    • 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
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    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
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Description

5 . j o ~i q 9 .7 0 7 L.
Akrylaattifungisidit ja niiden kåytto - Akrylatfungicider och deras anvåndning
Keksinnon kohteena ovat yhdisteet, joilla on sieniå, hyon-teisiå ulkoloisia tai rikkakasveja torjuva vaikutus.
Sieniå torjuvan vaikutuksen omaavia akryylihappojohdannai-10 sia on aiemmin esitetty useissa julkaisuissa, erityisesti julkaisuissa EP 178826 ja 203608.
EP-julkaisussa 178826 kuvataan 3-alkoksi-2-fenyyli-2-pro-penoiinihapon estereitå, joissa fenyyli voi olla substitu-15 oitu erilaisilla substituenteilla, mm. mahdollisesti subs-tituoidulla alkyylilla. Ainoat ryhmåt, jotka on esitetty substituentteina edellå mainitussa mahdollisesti substitu-oidussa alkyyliryhmåsså on halogeeni, fenyyli, fenoksi ja hydroksi. Olemme nyt havainneet, ettå metyyli-3-metoksi-2-20 fenyyli-2-propenonaatit, joissa fenyyli on ortosubstituoitu metyylillå, joka on substituoitu ryhmillå, joita ei edellå mainitussa EP-julkaisussa ole kuvattu, omaavat arvokkaita pestisidisiå ja erityisesti fungisidisia vaikutuksia.
25 EP-julkaisu 226917 kuvaa keksintoåmme muistuttavia yhdis- teitå, joissa fenyyliryhmå on substituoitu 2-asemassa inter alia mahdollisesti substituoidulla fenyylitiometyyliryhmål-lå. EP-203606 lisåksi kuvaa vastaavanlaisia yhdisteitå, joissa fenyyliryhmå on substituoitu 2-asemassa inter alia 30 mahdollisesti substituoidulla bentsyylioksiryhmållå. Olemme nyt huomanneet, ettå vastaavilla yhdisteillå, joissa subs-tituentti 2-asemassa on mahdollisesti substituoitu fenyyli-tiolilla, on erinomaiset sienten vastaiset aktiivisuudet.
35 Keksinnon mukaan valmistetaan kaavan I
92392 2 5 η R1 - (CH2) m-S- (CH2) ^ I OMe 0 = c^cf
10 I
OMe jossa (i) n on 1, m on = 0 ja R1 on substituoimaton tai substi- 15 tuoitu heteroaryyli, substituoimaton heterosyklyyli- (tio)karbonyyli, N-fenyyli-imino(alkyylitio)metyyli tai substituoitu heterosyklylideenimetyyli; tai (ii) n on 0 ja m on 1 ja R1 on substituoimaton tai substituoitu fenyyli; r 20 ja minkå tahansa emåksisten yhdisteiden happamet additio-suolat ja minkå tahansa happamien yhdisteiden emåksiset additiosuolat.
Keksinnon mukaisia yhdisteitå on strukturaalisina isomee-25 reina, ja keksinto kåsittåå niin yksittåisiå isomeereja kuin nåiden seoksia.
Termit heteroaryyli ja heterosyklyyli sisåltåvåt sellaisia ryhmiå kuin tienyyli, furyyli, pyridyyli, pyrimidyyli, 30 pyratsolyyli, tiatsolyyli, tiatsolinyyli, tiatsoloni, oksatsolyyli, bentsimidatsolyyli, tetratsolyyli, bentsok-;· satsolyyli, tiadiatsolyyli, dioksolanyyli, imidatsopyridi- nyyli, 1,3-bentsoksatsinyyli; l,3-bentsotiatsinyyli, oksat-solopyridinyyli, triatsolyyli, triatsinyyli, imidatsolyyli, 35 morfoliini, bentsofuranyyli, pyratsolinyyli, kinolinyyli, kinatsolinyyli, dihydrokinatsolinyyli tai bentsotiatsolyy-li, joilla itsellåån voidaan substituoida esim. fenyyli.
92392 3
Erityisen edullisen yhdisteryhmån muodostavat ne yhdisteet, joissa n on 1 ja R1 on heteroaryyli.
Keksinnon mukaiset yhdisteet ovat erityisen arvokkaita 5 fungisideina, erityisesti kåytettåvåksi kasvien sienitau-deissa, esim. viljanruosteet ja erityisesti viljan hår-måsieni (Erysiphe araminis), viinin levåsieni (Plasmonara viticola), riisiin ruostesieni (Pvricularia oryzae), viljan viirutauti (Pseudocoercosporella herpotrichoides), 10 riisin tuppiruostesieni (Pellicularia sasakii), harmaahome (Botrvtis cinerea.) , perunaraåtå (Rhizoctonia solani) , vehnån ruostesieni (Puccinia recondita) perunarutto (Phvtophthora infestans) ja omenarupi (Venturia inaeaualis). Muita sieni-tauteja, joihin yhdisteet voivat tehota ovat muut hårmåsie-15 net, muut ruostesienet ja yleiset Deuteromycete-, Ascomyce-te-, Phycomycete ja Basidomycete-peråiset patogeenit.
Keksinnån mukaisilla yhdisteillå on myos hyånteisiå, punk-keja ja sukkulamatoja torjuva vaikutus, ja ne ovat erityi-20 sen kåyttokelpoisia useiden taloudellista vahinkoa tuotta-vien hyonteisten, punkkien ja kasvien sukkulamatojen, sekå elåinten ulkoloisten ja erityisesti kaksisiipisten, kuten lampaan lihakårpåsen, Lucilla sericata. ja huonekårpåsen, Musca domestica: perhosten, kuten Plutella xvlostella.
25 Spodoptera littoralis. Heliothis armigera ja Pieris Brassi-. cae? yhtålåissiipisten, kuten lehtikirvojen, esim. Megoura viciae; kovakuoriaisten, kuten viljan juurimatojen (Diabro-tica spp., esim. Diabrotica undecimpunctata); ja håmåhåkki-punkkien kuten Tetranvchus spp. torjunnassa.
30
Keksintoon kuuluu myos menetelmå tuhosienten ja hyonteisten (s.o. sienten, hyonteisten, sukkulamatojen ja punkkien) torjumiseksi paikassa, johon niitå on ilmaantunut tai todennåkoisesti ilmaantuu. Menetelmå kåsittåå kaavan I 35 mukaisen yhdisteen levittåmisen ao. paikkaan.
92392 4
Keksintoon kuuluu myos tuhosienten ja -hyonteisten torjuntaan tarkoitettu seos, joka kåsittåå kaavan I mukaisen yhdisteen sekoitettuna maatalouskåyttoon hyvåksyttåvåån laimennusaineeseen tai kantajaan.
5
Keksinnon mukainen seos voi tietysti sisåltåå useamman kuin yhden keksinnon mukaisen yhdisteen.
Lisåksi yhdiste voi kåsittåå yhden tai useamman vaikuttavan 10 lisåaineen, esim. yhdisteitå, joilla tiedetåån olevan kasvin kasvua sååteleviå, rikkakasveja, sieniå, hyonteisiå tai punkkeja torjuvia ominaisuuksia. Vaihtoehtoisesti keksinnon mukaisia yhdisteitå voidaan kåyttåå peråkkåin muun vaikuttavan aineen kanssa.
15
Keksinnon mukaisen seoksen liuotin tai kantaja voi olla kiinteå aine tai neste, joka on valinnaisesti yhdistetty pinta-aktiiviseen aineeseen, esim. dispersioaineeseen, emulgointiaineeseen tai kostutusaineeseen. Sopivia pinta-20 aktiivisia aineita ovat anioniset yhdisteet, kuten karbok-sylaatti, esim. pitkåketjuisen rasvahapon metallikarboksy-laatti; N-asyylisarkosinaatti; rasva-alkoholietoksylaatteja sisåltåvån fosforihapon mono- tai diesterit tai tållaisten estereiden suolat; rasva-alkoholisulfaatit, kuten natrium-25 dodesyylisulfaatti, natriumoktadesyylisulfaatti tai nat- ; riumsetyylisulfaatti; etoksiloidut rasva-alkoholisulfaatit; etoksiloidut alkyylifenolisulfaatit; ligniinisulfonaatit, petrolisulfonaatit; alkyyli-aryylisulfonaatit, kuten alkyy-libentseenisulfonaatit tai alemmat alkyylinaftaleenisulfo-30 naatit, esim. butyyli-naftaleenisulfonaatti; sulfonoitujen naftaleeniformaldehydikondensaattien suolat; sulfonoitujen fenoliformaldehydikondensaattien suolat; tai monimutkaisem-mat sulfonaatit, kuten amidisulfonaatit, esim. oleiinihapon ja N-metyylitauriinin sulfonoitu kondensaatiotuote tai di-35 alkyylisulfosukkinaatit, esim. dioktyylisukkinaatin nat- riumsulfonaatti. Nonionisia aineita ovat rasvahappoesterei-den, rasva-alkoholien, rasvahappoamidien tai rasva-alkyyli- 5 y i. o y 2.
tai alkenyyli-substituoitujen fenolien etyleenioksidin kanssa muodostetut kondensaatiotuotteet, polyhydristen alkoholieettereiden kuten sorbitaanirasvahappoestereiden rasvaesterit, tållaisten estereiden etyleenioksidin kanssa 5 muodostetut kondensaatiotuotteet, esim. polyoksietyleeni-sorbitaanirasvahappoesterit, etyleenioksidin ja propyleeni-oksidin kappalepolymeerit, asetyleeniglykolit kuten 2,4,7,9-tetrametyyli-5-desyyni-4,7-diolia, tai etoksyloidut asetyleeniglykolit.
10
Kationisia pinta-aktiivisia aineita ovat esimerkiksi ali-faattinen mono-, di- tai polyamiini, kuten asetaatti, naftenaatti tai oleaatti; hapen sisåltåvå amiini kuten amiinioksidi tai polyoksietyleenialkyyliamiini; amidisidok-15 sinen amiini, joka on valmistettu kondensoimalla karboksyy-lihappo di- tai polyamiinin kanssa; tai kvaternåårinen ammoniumsuola.
Keksinnon mukaiset yhdisteet voivat olla misså tahansa 20 muodossa, joka on tunnettu maatalouskemikaalien muodostami-sessa, esim. liuoksena, dispersiona, vesipitoisena emulsiona, polytysjauheena, peittausaineena, desinfioimisaineena, savuna, syottinå, sirotteena, emulsiofioitavana tiivisteenå tai rakeina. Lisåksi se voi olla sopivassa muodossa levi-25 tettåvåksi suoraan tai tiivisteenå tai primååriseoksena, joka laimennetaan sopivalla måårålla vettå tai muuta liuo-tinta ennen levittåmistå.
Emulsifioitava tiiviste sisåltåå keksinnon mukaisen yhdis-30 teen liuotettuna veteen sekoittumattomaan laimennusainee-seen, joka on muodostettu vesipitoiseksi emulsioksi emul-goimisaineen låsnåollessa.
Polytysjauhe kåsittåå keksinnon mukaisen yhdisteen, joka on 35 perusteellisesti sekoitettu ja jauhettu kiinteån jauhemai-sen laimennusaineen, esim. kaoliinin kanssa.
92392 6
Rakeinen kiinteå aine sisåltåå keksinnon mukaisen yhdisteen yhdistettynå samanlaisiin laimennusaineisiin kuin ne, joita voidaan kåyttåå polytysjauheissa, mutta seos rakeistetaan tunnetuilla menetelmillå. Vaihtoehtoisesti seos kåsittåå 5 aktiivisen aineen, joka on absorboitu tai adsorboitu esira-keistettuun laimennusaineeseen, esim. Fullerin maahan, attapulgiittiin tai kalkkikivirouheeseen.
Kasteltavat jauheet, rakeet tai jyvåset sisåltåvåt tavalli-10 sesti vaikuttavan aineen sekoitettuna sopivaan pinta-aktii-viseen aineeseen ja inerttiin jauhemaiseen laimennusaineeseen kuten kaoliiniin.
Toinen sopiva tiiviste on juokseva suspensiotiiviste, joka 15 on muodostettu jauhamalla yhdiste veden tai muun nesteen, kostutusaineen ja suspendoimisaineen kanssa.
Vaikuttavan aineen pitoisuus keksinnon mukaisessa yhdis-teesså kasveille sovellettuna on edullisesti 0,001 - 3,0 % 20 painosta, erityisesti 0,01 - 1,0 % painosta. Primååriyhdis-teenå vaikuttavan aineen måårå voi vaihdella suuresti ja voi olla esim. 5 - 905 % yhdisteen painosta.
Keksinnon mukaisessa menetelmåsså yhdistettå levitetåån 25 yleenså siemeniin, kasveihin tai niiden kasvupaikkaan.
Siten yhdistettå voidaan levittåå suoraan maaperåån ennen rivikylvoå, sen aikana tai sen jålkeen, niin ettå vaikuttavan yhdisteen låsnåolo maaperåsså voi eståå siemeniin mahdollisesti ilmaantuvien sienten kasvua. Kun maaperå 30 kåsitellåån vålittomåsti, vaikuttava yhdiste voidaan levittåå millå tahansa tavalla, joka mahdollistaa yhdisteen perusteellisen sekoittumisen maaperåån, kuten sumuttamalla, hajakylvåmållå kiinteitå rakeita tai levittåmållå vaikutta-vaa ainetta rivikylvon yhteydesså kylvåmållå yhdistettå 35 samaan vakoon siementen kanssa. Sopiva kåyttomåårå on 0,05 - 20 kg hehtaaria kohti, edullisimmin 0,1 - 10 kg hehtaaria kohti.
* 92392 7
Vaihtoehtoisesti vaikuttavaa yhdistettå voidaan levittåå suoraan kasviin esim. suihkuttamalla tai polyttåmållå joko sienien alettua ilmestyå kasviin tai suojatoimenpiteenå ennen niiden ilmestymista. Molemmissa tapauksissa edullinen 5 levitysmuoto on lehtiin suihkutus. On yleenså tårkeåå valvoa tehokkaasti sienten ilmaantumista kasvin kasvun alkuvaiheessa, koska juuri tåsså vaiheessa kasvi voi vauri-oitua pahimmin. Suihke tai pålyte voi edullisesti sisåltåå esi- tai jålkivaikuttavaa herbisidiå, mikåli se katsotaan 10 tarpeellisesti. Joskus on edullista kåsitellå kasvin juuret ennen istutusta tai sen aikana, esim. upottamalla juuret sopivaan nesteeseen tai kiinteåån aineeseen. Kun vaikuttavaa ainetta levitetåån suoraan kasviin, sopiva kåyttomåårå on 0,10 - 10 kg hehtaaria kohti, edullisesti 0,05 - 5 kg 15 hehtaaria kohti.
Keksinnon mukaiset yhdisteet voidaan valmistaa useilla tavoin, esim. saattamalla kaavan II
20 ^ i i , x (11)
25 0 = C^^CH
OMe
mukainen yhdiste, jossa Z on jåånnosryhmå, kuten halogeeni, 30 reagoimaan kaavan III
R1 (CH-2) m~S~H (III) mukaisen yhdisteen kanssa.
» 35 8 O OZ Q O o y Δ.
Vaihtoehtoisesti kaavan IV
5 rj RMCHJ).-S-<aVn'''’^j (IV) o = cr OMe 10
mukainen yhdiste voidaan saattaa reagoimaan kaava V
(v) 15 HCOOCHj mukaisen formiaattiesterin kanssa emåksisisså olosuhteissa.
2 0 Yhdisteet, joissa X on SO tai S02, voidaan saada aikaan ha- pettamalla yhdiste, jossa X on S, sopivalla hapetusaineel-la, kuten metakloroentsoehapolla. Muut menetelmåt ovat ilmeisiå ala ammattimiehelle, kuten myos menetelmåt, joilla valmistetaan låhtoaineet ja vålituotteet. Esimerkeistå il-25 menee myos erilaisia menetelmiå keksinnon mukaisten yhdis-teiden sekå myos låhtoaineiden ja vålituotteiden valmista-miseksi.
Keksintoå havainnollistetaan seuraavissa esimerkeisså.
30 Eristettyjen uusien yhdisteiden rakenteet on todettu alku-aineanalyysillå ja/tai muilla sopivilla analyyseillå. Låmpdtilat on ilmaistu celsiusasteina.
Esimerkki 1 35
Metyyli-o-tolyyliasetaattia (100 g) liuotettiin metyylifor-miaatin (450 ml) ja dimetyyliformamidin (200 ml) seokseen.
92392 9
Liuos sekoitettiin bensiinillå puhdistettuun natriumhydri-disuspensioon (36,5 g:sta 80 %:n 51jydispersiossa) dimetyy-liformamidissa (100 ml) jååhdyttåen. Seosta sekoitettiin huoneen låmpotilassa yon ajan. Ylimååråinen metyyliformi-5 aatti ja suurin osa dimetyyliformamidista haihdutettiin, ja vettå (500 ml) lisåttiin. Seosta kåsiteltiin eetterillå ja vesivaihe erotettiin, hapotettiin ja uutettiin eetterillå. Uute sekoitettiin tavanomaisella tavalla ruskean oljyn aikaansaamiseksi. Tama liuotettiin tetrahydrofuraaniin, ja 10 liuos lisåttiin tipoittain natriumhydridiin 816,5 g 80 % 51jydispersiossa) tetrahydrofuraanista (50 ml) jååhdyttåen. Kun vetyå ei enåå muodostunut, lisåttiin metyylijodidia (35 ml) ja seos kuumennettiin takaisinvirtauksessa 5 tunnin ajan. Metanolia (5 ml) lisåttiin ja liuotin haihdutettiin. 15 Tuloksena saatu oljy jaettiin eetteriksi ja vedeksi, ja orgaaninen vaihe sekoitettiin tavanomaisella tavalla, jolloin saatiin aikaan metyyli(Z)-3-metoksi-2-(o-tolyyli)-prop-2-enoaatti, sulamispiste 68 - 70°C. Tåmå tuote (185 g) liuotettiin hiilitetrakloridin (1250 ml). N-Bromosukkinimi-20 dia (159,3 g) lisåttiin ja seosta kuumennettiin takaisinvirtauksessa 3 tunnin ajan. Reaktioseos jååhdytettiin ja sekoitettiin vaalean ruskean 61jyn aikaansaamiseksi. Raaka-tuote trituroitiin 10 % di-isopropyylieetteriliuoksella kevyesså petrolissa, jolloin saatiin metyyli(E)-3-metoksi-25 2-[ (2-bromometyyli) fenyyli] prop-2-enoaatti, sulamispiste 87 - 90°C. 2-merkaptobentsotiatsolia (101,87 g) tetrahydro-furaanissa (600 ml) lisåttiin tipoittain sekoittaen bensiinillå puhdistettuun natriumhydridiliuokseen (18,42 g 80 % oljydisperiossa), tetrahydrofuraanissa (200 ml). Seosta 30 kuumennettiin takaisinvirtauksessa 30 minuutin ajan ja se jååhdytettiin huoneen låmpotilaan. Bromometyyliyhdisteliu-osta (175 g) tetrahydrofuraanissa (1000 ml) lisåttiin tunnin ajan, ja seosta sekoitettiin viisi tuntia huoneen låmpotilassa. Vesipitoista tetrahydrofuraania lisåttiin reak-35 tion sammuttamiseksi, ja seos haihdutettiin. Jåånnos sekoitettiin tavanomaisella tavalla, jolloin saatiin metyyli(E)- 10 92ο 9 2 2-[2-[[(2-bentsotiatsolyyli)tio]metyyli]fenyyli]-3-metoksi-2-propenoaatti, sulamispiste 77 - 78°C. (Yhdiste 1)·
Esimerkki 2 5
Bentso[b]tiofeeni-2(3H)-onia (6 g) ja natriumhydroksidia (3,2 g) saatettiin takaisinvirtaukseen vedesså (40 ml) tunnin ajaksi. 4-klorobentsyylikloridia (6,44 g) lisåttiin, ja seos saatettiin takaisinvirtaukseen vielå 1,5 tunniksi 10 ja sen annettiin jååhtyå yon ajan. Vettå 825 ml) lisåttiin ja sen jålkeen etikkahappoa (100 ml). Kiinteå aine koot-tiin, puhdistettiin vedellå ja kuivattiin, jolloin saatiin [2-(4-klorobentsyylitio)fenyyli]etikkahappo, sulamispiste 149 - 151°C. Tåmån tuotteen ja (10,4 g) metanolin (250 ml) 15 muodostamaa liuosta, joka sisålsi rikkihappokonsentraattia (0,5 ml) kuumennettiin takaisinvirtauksessa yon ajan, ja ylimååråinen metanoli haihdutettiin. Eetteriå ja vettå lisåttiin, ja orgaaninen vaihde puhdistettiin vesipitoisella natriumhydroksidilla, kuivattiin ja haihdutettiin. Kiintey-20 tynyt tuote toistokiteytettiin heksaanista, jolloin saatiin låhtohapon metyyliesteri, sulamispiste 52 - 54°C. Tåmå kå-siteltiin metyyliformiaatilla ja natriumhydridillå samalla tavoin kuin esimerkisså 1 kuvatussa menettelysså, jolloin saatiin metyyli(E)-3-metoksi-2-[2-(4-klorobentsyylitio)-25 fenyyli]-prop-2-enoaatti, sulamispiste 81 - 84°C, (yhdiste 3) ja vastaava Z-isomeeri, sulamispiste 127 - 128°C, (yhdiste 4), joka erotettiin silikageelisauvakromatografialla.
Esimerkki 3 30
Metyylikloro-oksoasetaatin (22,5 ml) ja tetrahydrofuraanin "· (60 ml) seosta lisåttiin tipoittain yhden tunnin ajan se- koitettuun imidatsoliliuokseen (33,35 g) tetrahydrofuraa-nissa (500 ml), jota pidettiin 0°C:n låmpdtilassa typesså. 35 Seosta sekoitettiin vielå tunnin ajan tåsså låmpdtilassa.
Reaktioseos suodatettiin, ja sakka puhdistettiin tetrahyd-rofuraanilla. Suodate ja liete, jotka sisålsivåt metyyli 92392 11 a-okso-lH-imidatsoli-l-asetaattia, jååhdytettiin -65°C:een, ja Grignard-reagentin liuosta, joka oli valtfiistettu o-bro-motolueenista (42 g), 1,2-dibromoetaanista (3,6 ml) ja magnesiumista (7 g) tetrahydrofuraanissa, lisåttiin 45 5 minuutin ajan, pitåen låmpotilan -60 ja -70°C:n vålillå.
Sen jålkeen seosta sekoitettiin tåsså låmpotilassa 15 minuutin ajan ja huoneen låmpotilassa 2,5 tunnin ajan. Sen jålkeen se kaadettiin jåihin/veteen, uutettiin eetterillå, uutteet puhdistettiin suolaliuoksella, kuivattiin ja tii-10 vistettiin. Jåånnos tislattiin alennetussa paineessa, jolloin saatiin metyyliokso(o-tolyyli)asetaatti, kiehumis-piste 92 - 97°C/0,5 mm. Tåmån tuotteen liuos (5 g) meta- nolissa (100 ml) kuumennettiin takaisinvirtauksessa kolmen tunnin ajan metoksiamiinihydrokloridin (2,55 g) kanssa.
15 Seos jååhdytettiin, haihdutettiin, trituroitiin di-isopro-pyylieetterillå, suodatettiin, ja suodate haihdutettiin, jolloin saatiin metyyli(metoksi-imiini)(o-tolyyli)asetaat-tia. Tåmå kåsiteltiin N-bromosukkiini-imidillå hiilitetra-kloridissa takaisinvirtauksessa 300 watin lampun alla 20 lisåten bentsoyyliperoksidia (0,005 g) joka 10. minuutti. Tavanomaisella kåsittelyllå saatiin bromometyyliyhdiste, joka saatettiin reagoimaan 2-merkaptobentsotiatsolin kanssa samalla tavoin kuin esimerkisså 1 on kuvattu, jolloin saatiin metyyli [2-[[(2-bentsotiatsolyyli)tiojmetyyli]-25 fenyyli](metoksi-imiini)asetaatti, sulamispiste 113 - 114°C (tåmå yhdiste ei kuuluu patenttivaatimusten piiriin).
Samalla tavoin kuin kuvattu jossakin edellisistå esimer-keistå, saatiin seuraavat yhdisteet. Ellei toisin ole 30 ilmoitettu, yhdisteet ovat E-muodossa.
Γϊ
35 L
MeOCO cn-OMe 92392 12
Yhdiste sulamis- nro R1 m n piste 6 6-EtO-bentsotiatsol-2-yyli O 1 100-101 7 bentsoksatsol-2-yyli O 1 oljy 5 8 l-Me-imidatsol-2-yyli O 1 102-104 9 4-Me-pyrimidin-2-yyli O 1 94- 95 10 4,6-Me2-pyrimidiini-2-yyli O 1 oljy 11 4-But-lH-imidatsol-2-yyli 0 1 Iasi 12 (MeS) (3-Me-5-okso-l-Ph-pyratsolin- 10 4-ylideeni)metyyli O 1 129-131 13 pyrimidin-2-yyli O 1 75- 76 14 2-tiatsolin-2-yyli 0 1 104-106 15 5-MeCO-bentsotiatsol-2-yyli O 1 109-110 16 Ph (Z-isomeeri) 1 0 92- 94 15 17 5-CF3-bentsimidatsol-2-yyli 0 1 oljy 18 l-Ph-tetratsol-5-yyli O 1 126-127 19 5-CH3-bentsotiatsol-2-yyli O 1 97- 99 20 Ph 1 O 71- 74 21 4,4-Me2-5-raetyleeni-2-tiatsolin- 20 2-yyli 0 1 101 22 5-Ph-pyrimidin-2-yyli O 1 105-106,5 23 6-Cl-4-Me-bentsotiatsol-2-yyli O 1 89- 91 24 5-Me-bentsotiatsol-2-yyli 0 1 83- 85 25 5-aminobentsotiatsol-2-yyli O 1 hartsi 25 26 4-Cl-bentsotiatsol-2-yyli O 1 152-154 27 2-pyridyyli 0 1 80- 82 28 1-(3-N02-Ph)tetratsol-5-yyli O 1 93- 95 29 2-tienyyli 0 1 64- 65 30 5-Me-bentsoksatsol-2-yyli O 1 90- 91 30 31 3-CN-4-COOEt-6-Me-2-pyridyyli O 1 113-114 32 7-Cl-bentsotiatsol-2-yyli 0 1 132-134 ·; 33 5,6-Cl2-lH-bentsimidatsol-l-yyli 0 1 169,5-171 34 5-Cl-bentsoksatsol-2-yyli O 1 105-107 35 6-Cl-bentsoksatsol-2-yyli O 1 110-112 35 37 5-(2-N02-bentsylidiini)-4-okso- 2 -tiatsolin-2-yyli O 1 177-178,5 38 4-OH-5-Me-6-Pr-pyrimidin-2-yyli O 1 169-170 92392 13 39 imidatsoli[1,5-a]pyridin-3-yyli 0 1 77- 79 40 4-Ph-tiatsol-2-yyli O 1 oljy 41 5-propargyylitio-l,3,4-tiadiatsol- 2-yyli O 1 oljy 5 42 3-CN-4,6-Me2-2-pyridyyli O 1 140-142 43 3-MeO-Ph 1 O 87- 89 44 3-MeO-Ph (Z-isomeeri) 1 O 95- 97 45 l-Br-bentsimidatsol-2-yyli O 1 68- 70 46 4-Bufc-Ph 1 O oljy 10 47 4-pyridyyli O 1 101-103 49 l-Me-5-MeS-bentsimidatsol-2-yyli O 1 90- 92 50 l-Ph-l,2,4-triatsol-3-yyli O 1 oljy 51 l-Phi-bentsimidatsol-2-yyli O 1 oljy 52 5-Br-bentsotiatsol-2-yyli O 1 124-124,5 15 53 5-Br-lH-bentsimidatsol-2-yyli O 1 179-180 58 7-Cl-4-MeO-bentsotiatsol-2-yyli O 1 hartsi 59 lH-bentsimidatsol-2-yyli O 1 166-168 60 5-Cl-bentsotiatsol-2-yyli O 1 109-110 61 5-N02-bentsoksatsol-2-yyli O 1 120-122 20 62 5-t-Bu-bentsoksatsol-2-yyli O 1 85- 87 63 5-EtS-2-Me-bentsimidatsol-2-yyli O 1 hartsi 64 4,6,7-Cl3-bentsotiatsol-2-yyli O 1 159-161 65 5-Ph-tiatsol-2-yyli O 1 oljy 66 5,7-Me2-bentsoksatsol-2-yyli O 1 97- 98 25 67 6-Me-bentsoksatsol-2-yyli O 1 70- 73 68 morfoliinitioksometyyli O 1 97- 99 69 4-Cl, 3-MeO-Ph 1 O oljy 70 1,2,4-triatsol-l-yyli 1 O oljy 74 1,2,4-triatsin-3-yyli O 1 163 30 75 pyrimidin-4-yyli O 1 101 77 6-Pr-bentsotiatsol-2-yyli O 1 oljy 78 6-PhO-bentsotiatsol-2-yyli O 1 124-126 79 5-MeCONH-bentsotiatsol-2-yyli O 1 151-153 80 4-Ph-Ph 1 O 131-133 35 83 4-(4-Cl-PhO)-Ph 1 O 109-113 85 4-okso-3,4-dihydropyrimidin-2-yyli O 1 163 86 5-PhCONH-bentsotiatsol-2-yyli O 1 100 14 ο Og o s δ. -j y £ 87 5-(1,3-bentsodioksol-5-yylimety- leeniamino)bentsotiatsol-2-yyli 0 1 vaahto 88 4-okso-3,4-dihydrokinatsolin-2-yyli O 1 223-226 89 kinolin-2-yyli 0 1 88- 90 5 91 4-(4-Cl-PhO)-Ph (Z-isomeeri) 1 O 148-151 92 5-Ph-l,2,4-triatsin-3-yyli O 1 167 93 3-Ph-l,2,4-tiatiatsol-5-yyli O 1 oljy 96 5-PhCH=N-bentsotiatsol-2-yyli O 1 hartsi 97 5-PhN=C(MeS) O 1 hartsi 10 98 4-(4-Cl-Ph)-tiatsol-2-yyli O 1 99-102 99 4-(4-Me-Ph)-tiatsol-2-yyli O 1 hartsi 100 5-Me-4-Ph-tiatsol-2-yyli O 1 88- 91 101 5-Cl-l-H-bentsimidatsol-2-yyli O 1 161-164 102 2-Me-4-oksi-3,4-dihydro-kinatsolin- 15 2-yyli O 1 144-146 103 4-Me-5-Ph-tiatsol-2-yyli O 1 oljy 104 2H-1,4-bentsotiatsin-3-yyli O 1 oljy 105 2H-1,4-bentsoksatsin-3-yyli O 1 oljy 106 6-Cl-oksatsolo[4,5-b]pyridin-2-yyli O 1 114-116 20 107 5-Cl-l-Me-bentsimidatsol-2-yyli O 1 132-135
Esimerkki 4 Tåmå esimerkki kuvaa tyypillisiå konsentraatteja, joita 25 voidaan muodostaa keksinnon mukaisista yhdisteistå.
a) Kasteltava iauhe
Keksinnon mukainen yhdiste 25 % w/w
Natriumlignosulfonaatti 5 % w/w 30 Piihappo 5 % w/w
Kaoliini 65 % w/w b) Emulsifioitava tiiviste
Keksinnon mukainen yhdiste 250 g/1 35 Soprophor BSU1 200 g/1 N-Metyylipyrrolidoni 657 g/1 15 92oy 2 1 Tristyryylifenolietoksylaatti nonioninen emul-gointiaine
Testiesimerkki A 5
Arvioidaan yhdisteiden vaikutus yhtå tai useampaa seuraa-vista vastaan: a) Lehtitestit 10 Phvtophthora infestans: tomaattirutto (PI)
Plasmopara viticola: viinin levåsieni (PV)
Erysiohe qraminis: ohran hårmåsieni (EG)
Pvricularis orvzae: riisin ruostesieni (PO)
Pellicularia sasakii: riisin tuppiruostesieni (PS) 15 Botrvtis cinerea: tomaatin harmaahome (BC)
Venturia inaecrualis: omenarupi (VI)
Puccinia recondita: vehnån ruostesieni (PR)
Yhdisteiden vesipitoisia liuoksia tai dispersioita, joihin 20 sisåltyi kostutusaine, levitettiin eri pitoisuuksina suih-kuttamalla tai kastelemalla testikasvien varren alaosa. Kasveihin istutettiin asianmukaiset testipatogeenit, ja niitå pidettiin valvotuissa, kasvien kasvulle ja taudin kehittymiselle suotuisissa ympåristoolosuhteissa. Sopivan 25 ajan kuluttua lehden pinnan saama tartunta-aste arvioitiin silmåmååråisesti.
Yhdisteitå pidettiin aktiivisina, jos niiden taudinesto oli suurempi kuin 50 % pitoisuutena 125 ppm (w/v) tai våhemmån.
30 b) Maaperån patoqeenitesti Tåsså testisså arvioitiin yhdisteiden vaikutusta Rhizoctonia solania (RS) vastaan.
Hiekkaa/maissijauhoa sisåltåviin pulloihin istutettiin testisientå ja annettiin sen itåå. Maissijauho-hiekkavilje- 35 16 g o z q o J L· L· lyå sekoitettiin kompostimultaan, joka pantiin muoviastioi-hin. Yhdisteiden vesipitoisia liuoksia tai dispersioita, jotka sisålsivåt kostutusaineen, lisåttiin astioihin, jolloin kuhunkin astiaan saatiin haluttu yhdistepitoisuus.
5 Vertailuastioihin lisåttiin samanlaisia liuoksia tai dispersioita ilman testiyhdistettå. Heti testiyhdisteen lisåå-misen jålkeen kuhunkin astiaan kylvettiin kaalinsiemeniå. Siemenet peitettiin yhdisteellå kåsitellyllå sientå sisål-tåvållå mullalla, ja astioita idåtettiin valvotuissa, 10 kasvien kasvulle ja taudin kehittymiselle sopivissa olosuh-teissa. Itåneiden kaalintaimien lukumåårå laskettiin, ja taudinestoprosentti todettiin vertaamalla itåneitå taimia yhdisteellå kåsittelemåttomien, sientå sisåltåvien astioi-den tuloksiin.
15
Yhdisteet katsottiin aktiivisiksi, jos ne tuottivat suurem-man kuin 50 %:n taudineston pitoisuutena 100 osaa tai våhemmån yhdisteen painosta miljoonaa osaa multamååråstå kohti.
20
Vaikutukset esitettiin seuraavasti (+ = aktiivinen).
Yhdiste
nro_PI PV EG PO PS BC VI RS PR
25 1 + + + + + + 3 + + + + + + 4 + 6 + + + + + 7 + + + + + 30 8 + 9 + + + + + 10 + + + + + 11 + 12 + + 35 13 + + + + 14 + + + + 15 + + + + + + 17 92692 16++ + 17 + + 18 + 19 + ++ + 5 2 0 ++ + 21 + + + + + 22 + + + + + + + + 23 + + + + + + + 24 + + + + + + + + 10 25 + + + + + + 26+ + + ++ + 27 + + + + + 28++ + 29++ + + 15 30 + + + + + + + + 31 ++ + + 3 2 + ++ + + 33++ + 34 + + + + + + 20 35 + + + + 37 + 38 + 39 + 40 + ++ + + 25 41 + + .*42 ++ + + 43+ + + + 44 + + 45 + ++ + 30 46 + + 49 + + + + + + + + 50 ++ + 51++ + 52+ + + + + + 35 53 + + 59 + + 60 + + + + + + 92392 18 61 + + + 62 + + + + + + 63 + 64 + 5 65 + + + 66 + + + + + 67 + + + 69 + 70 + 10 71 + 74 + 75 + + 77 + + + + + 78 + + + + + 15 79 + + 80 + + 81 ++ + 82 ++. + 83 + 20 101 + +
Testiesimerkki B
Tåmå esimerkki havainnollistaa keksinnon mukaisten yhdis-25 teiden insektisidaalista vaikutusta. 1 ml testiyhdistettå eri vahvuuksina sisåltåvån asetonili-uoksen alikvootteja levitettiin 1 cm x 2 cm:n kokoisiin pumpulituppoihin, jotka oli sijoitettu lasiampulleihin, 30 joiden halkaisija oli 2 cm ja pituus 5 cm. Kun kåsitellyt tupot oli kuivattu, niihin imeytettiin 1 ml ravinneliuosta, jossa oli lampaan lihakårpåsen (Lucilia sericata) ensimmai-sen asteen toukkia, ampullit suljettiin pumpulitulpilla ja niitå pidettiin 25°C:n lampotilassa 24 tuntia. Vertailu-35 eråsså? toukkien kuolleisuus oli <5 %, kun taas esimerkki-en 6, 13, 15, 19 21-25 LC50 oli pienempi kuin 300 ppm.

Claims (4)

92392
1. Yhdiste, jonka kaava (I) on jQ R1- (CHj) m-S- (CHj) n OMe 0 =C^^CH
10 I OMe jossa (i) n on 1, m on 0 ja R1 on substituoimaton tai substitu-oitu heteroaryyli, substituoimaton heterosyklyyli- 15 (tio)karbonyyli, N-fenyyli-imino(alkyylitio)metyyli tai substituoitu heterosyklylideenimetyyli; tai (ii) n on 0 ja m on 1 ja R1 on substituoimaton tai substituoitu fenyyli; ja minkå tahansa emåksisten yhdisteiden happamet addit^o-20 suolat ja minkå tahansa happamien yhdisteiden emaksiset additiosuolat.
2. Patenttivaatimuksen 1 mukainen yhdiste, t u η n e t -t u siitå, ettå ettå kaavassa (I) n on 1, m on 0 ja R1 on 25 heteroaryyli. •
3. Tuhosienten ja -hyonteisten torjuntaan tarkoitettu seos, tunnettu siitå, ettå se sisåltåå vaatimuksen 1 tai 2 mukaisen yhdisteen sekoitettuna maanviljelyskåyttoon 30 hyvåksyttåvåån laimentimeen tai kantajaan.
4. Menetelmå tuhosienten ja -hyonteisten torjumiseksi niiden ilmenemispaikassa tai paikassa, johon niitå helposti ilmaantuu, tunnettu siitå, ettå menetelmå kåsittåå 35 patenttivaatimuksen 1 tai 2 mukaisen yhdisteen levittåmisen tåhån paikkaan. Q O - 0 O y c. o s L·
FI883297A 1987-07-11 1988-07-11 Akrylaattifungisidit ja niiden käyttö FI92392C (fi)

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ZW9388A1 (en) 1989-02-01
CN1025649C (zh) 1994-08-17
BR8803436A (pt) 1989-01-24
KR960012207B1 (ko) 1996-09-16
HU204658B (en) 1992-02-28
HUT47373A (en) 1989-03-28
DE3856431D1 (de) 2000-11-16
AU1880688A (en) 1989-01-12
DK381588D0 (da) 1988-07-08
PT87938B (pt) 1995-03-01
US5304530A (en) 1994-04-19
EP0299694A2 (en) 1989-01-18
ATE196900T1 (de) 2000-10-15
FI92392B (fi) 1994-07-29
KR890002091A (ko) 1989-04-08
NZ225339A (en) 1990-05-28
TR24201A (tr) 1991-07-01
PT87938A (pt) 1989-06-30
JPS6431746A (en) 1989-02-02
YU47288B (sh) 1995-01-31
DE3856431T2 (de) 2001-02-08
FI883297A0 (fi) 1988-07-11
US5192357A (en) 1993-03-09
EP0299694B1 (en) 2000-10-11
AU607235B2 (en) 1991-02-28
JP2688495B2 (ja) 1997-12-10
YU131888A (en) 1990-12-31
IL87020A (en) 1996-09-12
DK381588A (da) 1989-01-12
FI883297A (fi) 1989-01-12
IL87020A0 (en) 1988-12-30
EP0299694A3 (en) 1989-11-29
CN1031227A (zh) 1989-02-22

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