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WO1994029267A1 - Arylacetamides, leur procede de preparation, compositions les contenant et leur utilisation en tant que fongicides - Google Patents

Arylacetamides, leur procede de preparation, compositions les contenant et leur utilisation en tant que fongicides

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Publication number
WO1994029267A1
WO1994029267A1 PCT/EP1994/001938 EP9401938W WO9429267A1 WO 1994029267 A1 WO1994029267 A1 WO 1994029267A1 EP 9401938 W EP9401938 W EP 9401938W WO 9429267 A1 WO9429267 A1 WO 9429267A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
group
cor
ring
same
Prior art date
Application number
PCT/EP1994/001938
Other languages
English (en)
Inventor
Uwe Döller
Peter Braun
Burkhard Sachse
Original Assignee
Hoechst Schering Agrevo Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoechst Schering Agrevo Gmbh filed Critical Hoechst Schering Agrevo Gmbh
Priority to AU71239/94A priority Critical patent/AU7123994A/en
Priority to JP7501348A priority patent/JPH08511772A/ja
Priority to EP94920452A priority patent/EP0703899A1/fr
Publication of WO1994029267A1 publication Critical patent/WO1994029267A1/fr

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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
    • 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
    • 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
    • A01N37/40—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 having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • 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
    • A01N37/42—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 within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • 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
    • A01N43/72—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
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
    • C07C235/76—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C07C235/78—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
    • C07C235/80—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms having carbon atoms of carboxamide groups and keto groups bound to the same carbon atom, e.g. acetoacetamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/88—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having the nitrogen atom of at least one of the carboxamide groups further acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/52—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the nitrogen atom of at least one of the carboxamide groups further acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C243/30—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
    • C07C243/32—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
    • C07C255/44—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms at least one of the singly-bound nitrogen atoms being acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
    • C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
    • C07C271/64—Y being a hydrogen or a carbon atom, e.g. benzoylcarbamates
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07C311/46—Y being a hydrogen or a carbon atom
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
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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
    • C07D317/44—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 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—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 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms

Definitions

  • the present invention relates to arylacetamides, process for their preparation, compositions containing them and their use as fungicides.
  • the present invention thus relates to the use for
  • A is an optionally substituted aryl group
  • A' is an optionally substituted aryl group
  • B is a carbonyl group or a methylene group which is
  • X is an optionally substituted alkylene chain of 2 to 4 carbon atoms, in which two optional substituents on any one carbon can form an oxo or optionally
  • R 7 is heterocyclyl, aryl, silyl, alkyl, alkenyl,
  • cycloalkyl alkynyl, cycloalkenyl, amino, hydroxy, mercapto, each of which is optionally substituted or is hydrogen, cyano or acyl and in which when B is substituted by optionally substituted hydroxy, the substituent on the hydroxy can form a ring with either R 7 or with the other optional substituent on B.
  • X and R 7 are as previously defined;
  • B is a methylene group which is substituted by optionally substituted hydroxy
  • A' is dialkoxyphenyl, in which the phenyl group is
  • A is phenyl, substituted by one or more groups selected from halo, cyano, nitro, optionally substituted amino, optionally substituted alkyl, haloalkoxy, aryl, heterocyclyl, in which the phenyl group is optionally further substituted.
  • A is preferably phenyl,
  • alkyl groups and the alkyl moiety of alkyl-containing groups are preferably of 1 to 20, eg 1 to 6, carbon atoms.
  • Alkenyl and alkynyl groups are generally of 3 to 6 carbon atoms.
  • Cycloalkyl or cycloalkenyl groups are preferably of 3 to 8 carbon atoms.
  • Substituents, when present on any alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, alkoxy or alkylthio group include halogen, cyano, alkoxy (e.g. of 1 to 4 carbon atoms, and which may be substituted, e.g. by halo), hydroxy, alkylthio, nitro, optionally substituted amino, carboxy, alkoxycarbonyl, acyl, acyloxy, heterocyclyl and aryl.
  • Cycloalkyl or cycloalkenyl groups may also be substituted by alkyl.
  • Aryl groups are phenyl and when optionally substituted, substituents are, e.g. halogen, optionally substituted alkyl or alkoxy, aryl, heterocyclyl, aryloxy, cyano, nitro, optionally substituted amino or acyl or two
  • adjacent groups can form and fused benzo group which is optionally substituted as for aryl.
  • Preferred substituents on any aryl group are halogen, alkyl, trifluoromethyl, alkoxy, haloalkoxy, nitro, dialkylamino, amino or cyano.
  • Hydroxy and mercapto groups can be substituted by a range of groups including, e.g. optionally substituted alkyl, optionally substituted cycloalkyl, aryl, acyl, cyano and heterocyclyl
  • Optional further substituents on B, when it is a hydroxy substituted methylene group include those which can be optional substituents on hydroxy.
  • the term heterocyclyl includes both aromatic and non- aromatic heterocyclyl groups. Heterocyclyl groups are generally 5 or 6-membered rings containing up to 3 hetero atoms from nitrogen, oxygen and sulfur. The heterocyclyl groups may be fused to a benzene ring to form a fused heterocyclyl group. Examples of heterocyclyl groups are thienyl, furyl, pyridyl, pyrimidinyl, pyrazolyl,
  • tetrazolyl benzoxazolyl, thiadiazolyl, dioxolanyl, imidazopyridinyl, 1,3-benzoxazinyl, 1 ,3-benzothiazinyl, oxazolopyridinyl, triazolyl, triazinyl, imidazolyl, morpholino, benzofuranyl, pyrazolinyl, quinolinyl, quinazolinyl, sulfolanyl, dihydroquinazolinyl,
  • Amino groups may be substituted for example by one or two optionally substituted alkyl or acyl groups, or two substituents can form a ring, preferably a 5 to 7-membered ring, which may be substituted and may contain other hetero atoms, for example morpholine, thiomorpholine, or piperidine.
  • acyl includes the residue of sulfur
  • acyl groups are thus -COR a , -COOR a , -CO-Am, -CS-Am, -COSR a , -CSSR a , -S(O) q R a , -S(O) 2 OR a , -S(O) q Am,
  • R a and R b which may be the same or different, are hydrogen.
  • R a and R b which may be the same or different, are hydrogen.
  • A is a group of formula II or III
  • n, m' and n' are integers
  • n 1 to 7;
  • n' 0 to 7;
  • R 1 and R 2 which are the same or different and
  • R 3 and R 4 which are the same or different and independently of each other are hydrogen, (C 1 -C 18 )-alkyl,
  • R 3 and R 4 together form a (C 3 -C 6 )-alkylene group, in which a CH 2 -group is optionally replaced by CO, O, S or NR 3 ; R 3' is the same or different group from the group hydrogen,
  • B is a group of formula VI or VII;
  • R 5 is hydrogen, (C 1 -C 18 ) -alkyl, (C 3 -C 12 ) -cycloalkyl,
  • -COOR 3 , -CONR 3 R 4 or -SiR 3 3 and R 3 and R 4 are as defined above, in which in the second to eighth of the named groups optionally at least one of conditions a) to h) specified for groups R 1 and R 2 are fulfilled;
  • R 5 and R 6 together form a (C 3 -C 6 )-alkylene group, in which a CH 2 - group is optionally replaced by CO, O, S or NR 3
  • R 7 is hydrogen or, with the exception of nitro and
  • halogen is defined as for R 1 , or
  • X is a group of formula VIII,
  • R 8 , R 9 , R 10 and R 11 which are the same or different and
  • R 7 independently of each other, are as defined for R 7 or are halogen or nitro, and where R 8 and R 9 , or R 10 and R 11 , by forming an oxo group can also together be O, or
  • R 7 and R 8 together form a (C 2 -C 5 )-alkylene group
  • R 7 and R 10 together form a (C 1 -C 4 )-alkylene group
  • p 1, 2 or 3
  • R 1 and R 2 which are the same or different and
  • R 3, and B are as defined above;
  • R 5 is hydrogen, (C 1 -C 12 )-alkyl, (C 3 -C 12 )-cycloalkyl,
  • -COOR 3 , -CONR 3 R 4 or -SiR 3 3 and R 3 and R 4 are as defined above, in which in the second to eighth of the named groups, optionally at least one of conditions a) to h) specified for groups R 1 and R 2 are fulfilled;
  • R 7 is hydrogen or, with the exception of nitro and
  • halogen is as defined for R 1 , or
  • R 5 and R 7 form the above defined ring
  • R 6 and R 7 form the above defined ring
  • X is as defined above
  • R 7 + R 8 , R 7 + R 10 or R 8 + R 10 form the above defined ring and the groups which are not concerned with this ring connection are as defined above; and p is as defined above,
  • R 1 and R 2 which are the same or different and
  • R 5 and R 6 independently of each other are hydrogen
  • R 7 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl,
  • heterocyclic aryl groups each have up to 8 carbon atoms and up to 4 of the same or different hetero atoms selected from N, S and O,
  • R 8 , R 9 , R 10 and R 11 which are the same or different and
  • R 7 , or R 7 + R 8 , R 7 + R ? or R 8 + R 10 form part of a saturated or unsaturated 5 or 6-, 7- or 8-membered ring, and the remaining groups and variables are as defined above.
  • R 1 and R 2 which are the same or different and
  • fluoroalkylthio CN, OH, NO 2 , F, Cl, Br, I, CO 2 R 3 , OCOR 3 , COR 3 , NR 3 COR 4 , NR 3 R 4 , SO 3 R 3 , SO 2 NR 3 R 4 ,
  • heteroaryl, heteroaryloxy, in which the heterocyclic aryl groups each have up to 5 carbon atoms and up to 3 of the same or different hetero atoms selected from N, S and O, and R 3 and R 4 have the meanings given above; m 1 to 5,
  • n 1 to 4
  • n' 2 to 4;
  • R 5 and R 6 which are the same or different and
  • R 6 (C 2 -C 6 )-haloalkenyl, COOR 3 , COR 3 , CONR 3 R 4 or SiR 3 3 , and when R 5 is not hydrogen, R 6 can also be
  • R 5 with R 6 can form a saturated or unsaturated 5 or 6-membered ring and R 3 and R 4 have the meanings given above;
  • R 7 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl,
  • R 8 , R 9 , R 10 and R 11 which are the same or different and
  • R 7 , or R 7 + R 8 or R 7 + R 10 or R s + R 10 can be constituents of a saturated or unsaturated 5 or 6-membered ring and the remaining groups and variables are as defined above, as well as their salts, especially acid addition salts.
  • R 1 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl,
  • R 2 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl,
  • heterocyclic aryl groups each have up to 5 carbon atoms and up to 3 of the same or different hetero atoms selected from N, S and O, and R 3 and R 4 have the meanings given above, as well as their salts, especially acid addition salts.
  • a particularly preferred group of compounds are those where
  • A is of formula II, in which m is 1 or 2 and R 1 is halogen,
  • C 1 -C 4 -alkyl especially methyl, or halo-C 1 -C 4 -alkyl, especially trifluoromethyl and preferably with the R 1 in the 3 and/or 4 positions;
  • B is -CH(OH)-, -CH(O-acyl)- or -CH(O-alkyl);
  • R 7 is hydrogen
  • X is optionally substituted ethylene
  • A' is of formula IV, in which m' is 2 and R 2 is
  • C 1 -C 4 -alkoxy especially methoxy or ethoxy, and preferably with the R 2 in the 3 and 4 positions.
  • B is -CH(OH)- and X is ethylene.
  • halogen is to be understood a fluorine, chlorine, bromine or iodine atom
  • alkyl is to be understood a straight chain or branched hydrocarbon group, such as, e.g. methyl, ethyl, propyl, 1-methylethyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl, heptyl, octyl, 1,1,3,3-tetramethylbutyl, nonyl, isononyl, decyl, undecyl or dodecyl; by the term “cycloalkyl", v/hich is mono- bi- or tricyclic, preferably monocyclic, is to be understood, e.g.
  • cycloalkylalkyl is to be understood a hydrocarbon group, v/hich has the meanings given above under the term “alkyl” and v/hich is substituted by a hydrocarbon group, given under the term “cycloalkyl”, such as cyclohexylmethyl, 2-cyclohexylethyl or 2-cyclohexyl-2-propyl;
  • alkoxy is to be understood a hydrocarbon group, which has the meanings given above under the term
  • alkoxyalkyl is to be understood for example 1-methoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, methoxymethyl, ethoxymethyl, 3-methoxypropyl or 4-butoxybutyl;
  • haloalkyl is to be understood named alkyl group under the term “alkyl”, in which one or more
  • hydrogen atoms are replaced by the halogen atoms, named above, preferably chlorine or fluorine, such as CF 3 ,
  • haloalkoxy group whose halogen-hydrocarbon residue has the meaning given under the term "haloalkyl", such as OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CF 3 , OCH 2 CCl 3 , OCH(CF 3 ) 2 or
  • aryl is to be understood for example phenyl, naphthyl or biphenyl, especially phenyl;
  • aryl-alkyl is to be understood one of the above named alkyl groups, which is substituted with an aryl group, for example benzyl, 2-phenylethyl, 1- phenylethyl, 1-methyl-1-phenylethyl, 3-phenylpropyl or 4-phenylbutyl;
  • heteroaryl is to be understood an aryl group as previously defined in which at least one CH-group is replaced by N and/or at least two neighbouring CH-groups are replaced by S , NH or O.
  • groups are thienyl, furyl, benzofuryl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl and
  • alkythio-alkyl is to be understood for example methylthiomethyl, ethylthiomethyl,
  • alkenyl is to be understood, e.g. allyl, 1-methylallyl, 2-butenyl or 3-methyl-2-butenyl;
  • alkynyl is to be understood, e.g.
  • hemiacetals and hemiketals inasmuch as they are not stabilised by special groups, are as a rule unstable; such groups are not preferred.
  • the invention includes all stereoisomers , that can occur in the compounds of the invention of Formula I, especially individual enantiomers and their mixtures in any ratio, as well as their salts especially acid addition salts.
  • hydrogen halide acids such as hydrochloric acid or hydrobromic acid, as well as phosphoric acid, nitric acid, sulfuric acid, mono- or bi-functional carboxylic acids and hydroxycarboxylic such as acetic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, or lactic acid, as well as sulfonic acids such as for example p-toluenesulfonic acid or 1, 5-naphthalene- disulfonic acid.
  • the acid addition salts of the compounds of Formula I can be obtained in a simple manner according to conventional methods for forming salts, e.g. by
  • Base addition salts can be obtained by treatment with alkali or alkaline earth metal hydroxides or carbonates or with an organic amine.
  • the novel arylacetamides of formula I can be obtained in known manner, for example
  • Arylacetamides of formula I in which B is a group of formula VII, R 5 H and the remaining substituents are as defined in formula I are obtained for example by analogy to the method described in Synthesis (1985,) 12, 1153 by treatment of dioxolanones of formula IX, in which R 12 , R 13 independently of each other are H, (C 1 -C 8 )-alkyl, (C 1 -C 3 )-haloalkyl or R 11 and R 12 can be components of a 5-, 6- or 7-membered, saturated or mono-unsaturated, isocyclic ring and the remaining substituents are as defined in formula I with an amine of formula X in which the
  • the amines can be obtained in known manner as described for example in Bull. Chem. Soc. Jap. 1990, 63, 1252;
  • the reaction is carried out at a temperature of 0 up to the boiling point of the mixture, preferably under reflux over 0.5 to 120 hours.
  • the amine of formula X is treated in an amount of 1 to 10, preferably 1 to 2 molar
  • solvent Preferred solvents are ethers, aromatic or aliphatic hydrocarbons, halogenated hydrocarbons, ketones, alcohols or a mixture thereof, especially diethyl ether, dioxane, tetrahydrofuran, methyl tert-butyl ether,
  • the dioxolanones of formula IX can be obtained in a similar manner to that described in Organic Synthesis, Coll Vol 3, 536 and J. Org. Chem. Vol. 51 (19), 3747, (1986).
  • the compounds of formula I can also be obtained by treatment of a carboxylic acid of formula XI,
  • the process represents the acylation of a compound of formula X with a carboxylic acid of formula XI, whereby the reaction advantageously is carried out in the presence of acid XI activating compound or a dehydrating agent or with a reactive derivative of the carboxylic acid XI or of the educt X.
  • Examples of derivatives of formula XI that are optionally prepared in the reaction mixture are for example their alkyl, aryl or arylalkyl esters, such as the methyl, ethyl, phenyl or benzyl ester, their imidazolides, their acid halides such as the acid chloride or bromide, their anhydrides, their mixed anhydrides with aliphatic or aromatic carboxylic, sulfonic or carbonic acid esters, for example with acetic acid, propionic acid,
  • acid activating and/or dehydrating agents are chlorinated carbonic acid esters, such as ethyl
  • titanium tetraalkoxides such as titanium tetraisopropylate, titanium tetraethylate, titanium tetramethylate, titanium tetrapropylate or by the use of increased pressure (Angew Chemie, (1986), 6, 569).
  • reaction is suitably carried out in a solvent or mixture of solvents such methylene chloride, chloroform, carbon tetrachloride, ether, tetrahydrofuran, dioxane, benzene, toluene, acetonitrile, N-methylpyrrolidine or dimethylformamide, optionally in the presence of an inorganic base such as sodium or potassium carbonate or a tertiary organic base such as triethylamine,
  • N-methylmorpholine or pyridine which can also act at the same time as a solvent, and optionally in the presence of an acid activating agent, at temperatures between -78°C and 120°C, preferably however at temperatures between -78 °C and the boiling point of the reaction mixture.
  • the compounds are especially
  • the activity spectrum of the claimed compounds includes various economically important phytopathogenic fungi, for example Phytophthora infestans and Plasmopara viticola .
  • the compounds can be used to treat crop seeds to prevent seed borne diseases.
  • the compounds of the invention are suitable also for the use in technical areas, for example as wood preservatives, as preservatives in paints, thickeners, in cooling
  • compositions of the invention contains generally from 1 to 95 % by weight of the active ingredient.
  • Formulation possibilities are included, for example, wettable powders (WP), emulsifiable concentrates (EC), aqueous dispersions in oil or water based (SC),
  • WP wettable powders
  • EC emulsifiable concentrates
  • SC aqueous dispersions in oil or water based
  • suspoemulsions SC
  • dusting powders DP
  • disinfectants granules in the form of water-dispersible granules (WG)
  • WG water-dispersible granules
  • ULV-formulations rr.icrocapsules
  • waxes or baits these individual formulation types are known and are described for example in:
  • the necessary formulation additives are also known as inert materials, surfactants, solvents and other additives and are described for example in:
  • fertilisers and/or growth regulators can be prepared, for example in the form of a ready formulation or as a tank mix.
  • Wettable powders are preparations that are evenly
  • dispersible in water which besides the substance also contain a diluent or inert substance including a
  • surfactant for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkyl or alkylphenol sulfonate and dispersing agents for example sodium
  • Emulsifiable concentrates are prepared by dissolving the active
  • emulsifiers there can be used for example, calcium salts of
  • alkylarylsulfonic acids such as calcium
  • dodecylbenzenesulfonate or non-ionic emulsifiers such as fatty acid polyglycol esters, alkylarylpolyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide, ethylene oxide, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitan esters.
  • Dusting agents can be obtained by milling the active ingredient with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite, pyrophyllite, or diatomaceous earths.
  • Granules can be prepared either by distribution of the active ingredients on absorbing granular inert materials or by bringing concentrates of active ingredients by means of sticking agents, for example polyvinyl alcohol, sodium
  • Suitable active ingredients can also be
  • the active ingredient concentration is for example around 10-9%, the rest of up to 100%
  • the active ingredient concentration is around 5-80%. Dusting formulations contain at most 5-20%. In granulates the active ingredient content depends partly on whether the active compound is liquid of solid and which compound is liquid or solid and which granulating
  • active ingredient formulating agents there can be optionally conventional adhesive, surfactant, dispersing, emulsifying, penetration, solvent, filling or carrier substances.
  • the concentrates in commercially available forms are usually diluted in conventional manner, for example wetting powders, emulsifiable concentrates, dispersions and also micro granules by using water. Dusts and granule preparations as well as sprayable solutions are generally not diluted before use with further inert substances
  • the necessary rate of use can be varied. It can be limited within wide ranges, for example between 0.005 and 10,0 kg/ha or more active substances, for example by between 0.01 and 5 kg/ha.
  • the active ingredients of the invention can be used in their commercial formulations, either alone or in
  • the compounds of the invention can be combined with most known fungicides including for example:
  • fungicide selected from the group consisting of chlorothalonil, dimethomorph, fenpiclonil, fluazinam, hymexazol, nuarimol, pencycuron,
  • Conazoles are defined in ISO standard 257 as compounds based on imidazole or 1,2,4-triazole and containing a halogenated phenyl group. Examples include prochloraz (and its metal complexes - especially the manganese or copper complex), propiconazole, flusilazole, hexaconazole, tebuconazole, difenoconazole, bromuconazole,
  • imibenconazole furconazole, tetraconazole, myclobutanil, penconazole, fluquinconazole, azaconazole, imazalil, triflumizole, epoxiconazole, triticonazole, metconazole and the fungicide having the code No SSF 109.
  • type (ii) fungicides include fenpropimorph and fenpropidin.
  • type (iii) fungicides include mancozeb and thiram.
  • type (iv) fungicides include folpet, captafol and captan.
  • type (v) fungicides include
  • anilino nitrogen comprises a ring carrying two oxo substituents, in positions adjacent the nitrogen, e.g. iprodione, vinclozolin or procymidone, or b) acetanilide fungicides, e.g. metalaxyl or ofurace, c) sulfanilide fungicides, e.g. dichlofluanid,
  • benzanilide fungicides e.g. flutolanil
  • heteroarylanilide fungicides e.g. thifluzamide.
  • type (vi) fungicides include carbendazim, benomyl and thiophanate-methyl.
  • type (vii) fungicides include diethofencarb and propamocarb.
  • type (viii) fungicides include Bordeaux mixture, oxine-copper, copper oxychloride and copper naphthenate.
  • type (ix) fungicides include tributyltin oxide and tributyltin naphthenate.
  • Strobilurine type fungicides are methyl esters of arylacetic acid in which the acetic acid also carries a methoxymethylene or methoxyimino
  • the aryl group is usually a 2-substituted phenyl group. Examples of such compounds are those
  • type (xi) fungicides include pyrimethanil, cyprodinil and mepanipyrim.
  • type (xii) fungicides include pyrazophos, fosetyl aluminium and tolclofos-methyl .
  • the compounds of the invention in commercial formulations as v/ell as the ready for use forms from these formulations can be mixed with other active ingredients, such as insecticides, desiccating agents, sterilants, acaricide, nematicides or herbicides.
  • active ingredients such as insecticides, desiccating agents, sterilants, acaricide, nematicides or herbicides.
  • insecticides include phosphorus acid esters, carbamates, carboxylates, formamidine, tin compounds, compounds prepared from microorganisms, etc.
  • Preferred mixing partners are:
  • pirimiphos-methyl profenofos, propaphos, propetamphos, prothiofos, pyraclofos, pyridapenthion, quinalophos, sulprofos, temephos, terbufos, tetrachlorvinphos,
  • aldicarb 2-sec.-butylphenyl methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb,
  • acrinathrin allethrin, alpha-cypermethrin, 5-benzyl-3-furylmethyl-(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropane-carboxylate, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, biphenate, cycloprothrin, cyhalothrin, cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D-isomer), bifenthrin,
  • thuringiensis bensultap, binapacryl, bromopropylate, buprofezin, cartap, chlorobenzilate, chlorfluazuron, clofentezine, chlorfluazuron, cyromazine, dicofol, hexaflumuron, diflubenzuron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene)-2,4-xylidine, dinobuton, dinocap, endosulfan, ethofenprox, (4-ethoxyphenyl) (dimethyl) (3-(3-phenoxyphenyl)propyl)silane, silafluofen, fenproximate, fenazaquin, fenoxycarb, fipronil, fluazuron, flufenoxuron, flubenzimine, flucycloxuron, flufenoxuron, gamma-HCH, hexa
  • propargite pymetrozin, pyrolen, pyridaben, triazamate, tebufenozid, tebufenpyrod, teflubenzuron, tetradifon, tetrasul, thiocyclam, triflumuron.
  • the content of active ingredient in the ready for use forms, prepared from the commercial formulations, can vary over a wide range with the concentration varying from 0.0001 up to 95% by weight of active ingredient,
  • a granulate was prepared from 2 to 15 parts by
  • an inert granulate carrier material such as attapulgite, pumice
  • granules and/or quartz sand Suitably a suspension of the wettable powder from Example b) having a solid material content of 30 % is sprayed on the surface of a attapulgite granules, dried and mixed intimately.
  • the ready granules comprise an amount by weight of ca. 5 % of the wettable powder and ca. 95 % of the carrier material.
  • Trimethylsilyl chloride (1.1 ml) was added dropwise, with stirring to mixture of 4-cyanomandelic acid (0.7 g, 4.0 mmol) in dry dichloromethane (8 ml) and pyridine (0.67 ml) and a catalytic amount of dimethylaminopyridine. The mixture was stirred for 4 hours at room temperature, cooled to 0°C and 3 drops dimethylformamide added followed by oxalyl chloride (0.36 ml). The mixture was stirred for a further 1 hour at 0°C and 30 minutes at room
  • Butyllithium (32 ml) was added dropwise via a syringe to diisopropylamine (8.08 g) under nitrogen, dissolved in dry tetrahydrofuran (150 ml) at -60°C. The mixture was warmed to -5°C and then cooled again to -60°C and treated with a solution of isobutyric acid (3.52 g) in tetrahydrofuran (20 ml). The mixture was allowed to warm to room
  • the compound of the invention was subjected to various tests.
  • the compound was assessed for activity against
  • Plasmopara viticola (vine downy mildew - PV).
  • Aqueous solutions or dispersions of the compound at the desired concentration, including a wetting agent, were sprayed onto the appropriate plant and then inoculated by spraying with spore suspensions of the fungi. Plants were then kept under controlled environment conditions suitable for maintaining plant growth and development of the disease. After an appropriate time, the degree of

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Abstract

Composés de la formule (I) dans laquelle A représente un groupe aryle éventuellement substitué; A' représente un groupe aryle éventuellement substitué; B représente un groupe carbonyle ou méthylène substitué par un hydroxy éventuellement substitué et un éventuel substituant supplémentaire; X représente une chaîne alkylène éventuellement substituée de 2 à 4 atomes de carbone dans laquelle deux éventuels substituants sur n'importe quel atome de carbone peuvent former un groupe oxo ou un groupe imino éventuellement substitué; et R7 représente hétérocyclyle, aryle, silyle, alkyle, alcényle, cycloalkyle, alkynyle, cycloalcényle, amino, hydroxy, mercapto, chacun étant éventuellement substitué, ou représente hydrogène, cyano, acyle, et dans lequel, lorsque B est substitué par un hydroxy éventuellement substitué, le substituant sur l'hydroxy peut former un cycle avec R7 ou l'autre substituant sur B; lesdits composés présentent une activité fongicide, en particulier contre les champignons phytopathogènes.
PCT/EP1994/001938 1993-06-16 1994-06-14 Arylacetamides, leur procede de preparation, compositions les contenant et leur utilisation en tant que fongicides WO1994029267A1 (fr)

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EP94920452A EP0703899A1 (fr) 1993-06-16 1994-06-14 Arylacetamides, leur procede de preparation, compositions les contenant et leur utilisation en tant que fongicides

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WO2000041998A1 (fr) * 1999-01-11 2000-07-20 Syngenta Participations Ag Nouveaux derives de propargylether
WO2001087822A1 (fr) * 2000-05-17 2001-11-22 Syngenta Participations Ag Nouveaux derives de phenyle-propargylether
US6521663B2 (en) 2000-10-06 2003-02-18 3-Dimensional Pharmaceuticals, Inc. Aminoguanidinyl- and Alkoxyguanidinyl-substituted phenyl acetamides as protease inhibitors
US6555709B1 (en) 1997-04-09 2003-04-29 Hoechst Schering Agrevo S.A. Aromatic amides, their preparation process and their use as pesticides
WO2003042168A1 (fr) * 2001-11-16 2003-05-22 Syngenta Participations Ag NOUVEAUX DERIVES PHENETHYLAMIDES D'ACIDE CARBOXYLIQUE α-OXYGENES OU α-THIOLES
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WO2004011417A1 (fr) * 2002-07-24 2004-02-05 Syngenta Participations Ag Amide d'acide n-bisaryl- et n-aryl-cycloalkylidenyl-alpha-hydroxy- et alpha-alcoxy
WO2003042166A3 (fr) * 2001-11-16 2004-03-04 Syngenta Participations Ag PROCEDE DE PREPARATION D'AMIDES D'ACIDE HYDROCARBOXYLIQUE-α
WO2004033413A3 (fr) * 2002-10-10 2004-06-10 Syngenta Participations Ag Nouveaux derives de propargylether pour la lutte contre les microorganismes phytopathogenes
WO2014006945A1 (fr) 2012-07-04 2014-01-09 アグロカネショウ株式会社 Dérivé d'ester d'acide 2-aminonicotinique et bactéricide le contenant comme principe actif
WO2014070983A1 (fr) * 2012-10-31 2014-05-08 The Regents Of The University Of Michigan Inhibiteurs de l'activateur 1 du plasminogène et leurs procédés d'utilisation
US9527878B2 (en) 2007-04-16 2016-12-27 The Regents Of The University Of Michigan Plasminogen activator inhibitor-1 inhibitors and methods of use thereof to modulate lipid metabolism
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AU4265596A (en) * 1994-12-06 1996-06-26 Agrevo Uk Limited Heterocyclyl substituted hydroxyacetamide derivatives as fongicides
DE19642863A1 (de) * 1996-10-17 1998-04-23 Bayer Ag Amide
GB0127554D0 (en) * 2001-11-16 2002-01-09 Syngenta Participations Ag Organic compounds
WO2005068416A1 (fr) * 2003-12-12 2005-07-28 Sumitomo Chemical Company, Limited Compose d'amide et methode de lutte contre des maladies des plantes au moyen de ce compose
JP5793883B2 (ja) * 2010-03-03 2015-10-14 住友化学株式会社 植物病害防除組成物及び植物病害防除方法
CN103288669B (zh) * 2013-07-01 2015-06-24 南开大学 一种阿卓乳酸酰胺衍生物及应用
CN111747873B (zh) * 2019-03-29 2022-04-08 成都同心纵横生物医药有限公司 一种艾瑞昔布中间体及其制备方法和用途

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US5990171A (en) * 1995-04-05 1999-11-23 Bayer Aktiengesellschaft Hydrazonoacetic acid amides and the use thereof as pesticides
US6555709B1 (en) 1997-04-09 2003-04-29 Hoechst Schering Agrevo S.A. Aromatic amides, their preparation process and their use as pesticides
US6469005B1 (en) 1999-01-11 2002-10-22 Syngenta Participations Ag Propargylether derivatives
CZ302201B6 (cs) * 1999-01-11 2010-12-15 Syngenta Participations Ag Deriváty propargyletheru, zpusob jejich prípravy a prostredek proti fytopatogenním mikroorganismum
WO2000041998A1 (fr) * 1999-01-11 2000-07-20 Syngenta Participations Ag Nouveaux derives de propargylether
RU2237058C2 (ru) * 1999-01-11 2004-09-27 Зингента Партисипейшнс Аг Новые производные простого пропаргилового эфира
AU2001260301B2 (en) * 2000-05-17 2004-11-04 Syngenta Participations Ag Novel phenyl-propargylether derivatives
WO2001087822A1 (fr) * 2000-05-17 2001-11-22 Syngenta Participations Ag Nouveaux derives de phenyle-propargylether
AP1601A (en) * 2000-05-17 2006-04-28 Syngenta Participations Ag Novel phenyl-propargylether derivatives.
US6683211B1 (en) 2000-05-17 2004-01-27 Syngenta Crop Protection, Inc. Phenyl-propargylether derivatives
RU2259353C2 (ru) * 2000-05-17 2005-08-27 Зингента Партисипейшнс Аг Новые производные фенилпропаргилового эфира
US6521663B2 (en) 2000-10-06 2003-02-18 3-Dimensional Pharmaceuticals, Inc. Aminoguanidinyl- and Alkoxyguanidinyl-substituted phenyl acetamides as protease inhibitors
US6900231B2 (en) 2000-10-06 2005-05-31 3-Dimensional Pharmaceuticals, Inc. Aminopyridyl-substituted phenyl acetamides as protease inhibitors
WO2003042168A1 (fr) * 2001-11-16 2003-05-22 Syngenta Participations Ag NOUVEAUX DERIVES PHENETHYLAMIDES D'ACIDE CARBOXYLIQUE α-OXYGENES OU α-THIOLES
EP2314568A3 (fr) * 2001-11-16 2012-02-29 Syngenta Participations AG Nouveaux dérivés phénéthylamides d'acide carboxylique alpha-oxygenes ou alpha-thioles
EP1526128A3 (fr) * 2001-11-16 2005-06-08 Syngenta Participations AG Rocédé de preparation d'amides de l'acide alpha hydroxycarboxilique
WO2003042166A3 (fr) * 2001-11-16 2004-03-04 Syngenta Participations Ag PROCEDE DE PREPARATION D'AMIDES D'ACIDE HYDROCARBOXYLIQUE-α
WO2003042167A1 (fr) * 2001-11-16 2003-05-22 Syngenta Participations Ag Nouveaux derives phenethylamide de l'acide carboxylique $g(a)-oxygenes ou $g(a)-thioles
EP2314568A2 (fr) 2001-11-16 2011-04-27 Syngenta Participations AG Nouveaux dérivés phénéthylamides d'acide carboxylique alpha-oxygenes ou alpha-thioles
AP1843A (en) * 2001-11-16 2008-04-30 Syngenta Participations Ag Novel ?-oxygenated or ?-thiolated carboxylic acid penethylamide derivatives.
US7521579B2 (en) 2001-11-16 2009-04-21 Syngenta Crop Protection, Inc. Process for the preparation of alpha hydroxycarboxylic acid amides
EA011548B1 (ru) * 2001-11-16 2009-04-28 Зингента Партисипейшнс Аг НОВЫЕ ПРОИЗВОДНЫЕ ФЕНЕТИЛАМИДОВ α-КАРБОНОВЫХ ИЛИ α-ТИОКАРБОНОВЫХ КИСЛОТ
US7601674B2 (en) 2001-11-16 2009-10-13 Syngenta Crop Protection, Inc. α-oxygenated or α-thiolated carboxylic acid phenethylamide derivatives
KR100934112B1 (ko) * 2001-11-16 2009-12-29 신젠타 파티서페이션즈 아게 신규한 α-산소화 또는 α-티올화 카복실산 펜에틸아미드유도체
US7700522B2 (en) 2001-11-16 2010-04-20 Syngenta Crop Protection, Inc. α-Oxygenated or α-thiolated carboxylic acid phenethylamide derivatives
WO2004011417A1 (fr) * 2002-07-24 2004-02-05 Syngenta Participations Ag Amide d'acide n-bisaryl- et n-aryl-cycloalkylidenyl-alpha-hydroxy- et alpha-alcoxy
US7166746B2 (en) 2002-07-24 2007-01-23 Syngenta Crop Protection, Inc. N-bisaryl- and n-aryl-cycloakylidenyl-αhydroxy-and α-alkoxy acid amides
WO2004033413A3 (fr) * 2002-10-10 2004-06-10 Syngenta Participations Ag Nouveaux derives de propargylether pour la lutte contre les microorganismes phytopathogenes
US9527878B2 (en) 2007-04-16 2016-12-27 The Regents Of The University Of Michigan Plasminogen activator inhibitor-1 inhibitors and methods of use thereof to modulate lipid metabolism
WO2014006945A1 (fr) 2012-07-04 2014-01-09 アグロカネショウ株式会社 Dérivé d'ester d'acide 2-aminonicotinique et bactéricide le contenant comme principe actif
KR20150042781A (ko) 2012-07-04 2015-04-21 아구로카네쇼 가부시키가이샤 2-아미노니코틴산에스테르 유도체 및 이를 유효 성분으로 하는 살균제
US9096528B2 (en) 2012-07-04 2015-08-04 Agro-Kanesho Co., Ltd. 2-aminonicotinic acid ester derivative and bactericide containing same as active ingredient
WO2014070983A1 (fr) * 2012-10-31 2014-05-08 The Regents Of The University Of Michigan Inhibiteurs de l'activateur 1 du plasminogène et leurs procédés d'utilisation
US9718760B2 (en) 2012-10-31 2017-08-01 The Regents Of The University Of Michigan Plasminogen activator inhibitor-1 inhibitors and methods of use thereof
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HU9503609D0 (en) 1996-02-28
CN1128019A (zh) 1996-07-31
HUT73352A (en) 1996-07-29
JPH08511772A (ja) 1996-12-10
IL110037A0 (en) 1994-10-07
AU7123994A (en) 1995-01-03
DE4319887A1 (de) 1994-12-22
EP0703899A1 (fr) 1996-04-03

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