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EP0703899A1 - 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
EP0703899A1
EP0703899A1 EP94920452A EP94920452A EP0703899A1 EP 0703899 A1 EP0703899 A1 EP 0703899A1 EP 94920452 A EP94920452 A EP 94920452A EP 94920452 A EP94920452 A EP 94920452A EP 0703899 A1 EP0703899 A1 EP 0703899A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
group
cor
ring
same
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP94920452A
Other languages
German (de)
English (en)
Inventor
Uwe Döller
Peter Braun
Burkhard Sachse
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Hoechst Schering Agrevo GmbH
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Filing date
Publication date
Application filed by Hoechst Schering Agrevo GmbH filed Critical Hoechst Schering Agrevo GmbH
Publication of EP0703899A1 publication Critical patent/EP0703899A1/fr
Withdrawn legal-status Critical Current

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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
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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
    • A01N43/74—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
    • 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
    • C07C235/42—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
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    • 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
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    • 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
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    • 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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    • C07D—HETEROCYCLIC COMPOUNDS
    • 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

  • Arylacetamides process for their preparation, compositions containing them and their use as fungicides
  • the present invention relates to arylacetamides, process for their preparation, compositions containing them and their use as fungicides.
  • Substituted arylacetamides containing in which an optionally substituted hydroxy group is attached at the ..-position are described as active components in herbicides (JP- 5 8032-853) and as compositions for treating skin diseases (EP-A-98743) . There are also many references to compounds of this type as intermediates and in the chemical literature.
  • the present invention thus relates to the use for combating fungi, of a compound of formula I, its stereoiso ers as well as mixtures of these, 0
  • 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 substituted by optionally substituted hydroxy and an optional further substituent;
  • X is an optionally substituted alkylene chain of 2 to 4 carbon atoms, in v/hich two optional substituents on any one carbon can form an oxo or optionally substituted imino group; and 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.
  • B is a methylene group which is substituted by optionally substituted hydroxy
  • A' is dialkoxyphenyl, in which the phenyl group is optionally further substituted; and 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.
  • novel compounds A is preferably phenyl, substituted by one or more groups selected from halo, cyano, alkyl, trifluoromethyl and haloalkoxy. It is particularly preferred that there is a substituent in the 4-position.
  • A' is preferably 3,4-dimethoxyphenyl or 4-ethoxy- 3-methoxyphenyl.
  • the invention also includes as novel compounds all the compounds in the tables for v/hich a melting point or a physical description, such as oil, gum, wax or foam has been given.
  • 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.
  • 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.
  • 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.
  • heterocyclyl groups are thienyl, furyl, pyridyl, pyri idinyl, pyrazolyl, thiazolyl, thiazolinyl, oxazolyl, benzimidazolyl, tetrazolyl, benzoxazolyl, thiadiazolyl, dioxolanyl, imidazopyridinyl, 1, 3-benzoxazinyl, 1, 3-benzothiazinyl, oxazolopyridinyl, triazolyl, triazinyl, imidazolyl, orpholino, benzofuranyl, pyrazolinyl, quinolinyl, quinazolinyl, sulfolanyl, dihydroquinazolinyl, benzothiazolyl, piperidinyl, phthalimido, 2-oxopyrrolidino, 2-oxobenzoxazolin-3-yl and benzo
  • 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 and phosphorus-containing acids as well as carboxylic acids.
  • optionally substituted alkyl optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted alkenyl, optionally substituted alkynyl, aryl or heterocyclyl, Am is optionally substituted amino and q is 1 or 2.
  • A is a group of formula II or III
  • R 1 and R 2 which are the same or different and independently of each other, are (C,-C 18 ) -alkyl,
  • R 3 and R 4 which are the same or different and independently of each other are hydrogen, (C j -C 18 ) -alkyl, (C 3 -C 12 ) -cycloalkyl, (C 3 -C 12 ) -cycloalkyl-(C
  • 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, (C C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C j -C 6 ) -haloalkyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl-(C,-C 4 ) -alkyl, (C 6 -C 10 ) -aryl, (C 7 -C n ) -aralkyl and (C
  • B is a group of formula VI or VII;
  • R 5 is hydrogen, (C [ -C 18 ) -alkyl, (C 3 -C 12 ) -cycloalkyl, (C 3 -C, 2 ) -cycloalkyl- (C r C ⁇ ) -alkyl, (C 6 -C 18 ) -aryl, (C 6 -C 18 ) -aryl-(C,-C 6 ) -alkyl, (C j -C 8 ) -heteroaryl, (C,-C 8 ) -heteroaryl-(C [ -C 6 ) -alkyl, cyano, -COR 3 , -COOR 3 , -CONR-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 8 , R 9 , R 10 and R 11 which are the same or different and 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
  • Preferred compounds of formula I are those in which R 1 and R 2 , which are the same or different and independently of each other, are (C t -C 12 ) -alkyl, (C 3 -C 12 ) -cycloalkyl, (C 3 -C 12) -cycloalkyl-(C j -C 4 ) -alkyl, (C 6 -C 12 )-aryl, (C 6 -c 12 ) -aryl-(C r C 4 ) -alkyl, (C,-C 8 ) -heteroaryl, (C,- 8 ) -heteroaryl-(C j -C 4 ) -alkyl, cyano, nitro, halogen, -COR 3 , -C00R 3 , -CONR 3 R 4 , -OR 3 , -0C0R 3 , -0C00R 3 , -OCO-NR 3 R 4 ,
  • R 3 and R 4 which are the same or different and independently of each other, are (C,-C 17 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkyl-(C j -C 4 ) -alkyl, (C 6 -C, 2 )-aryl, (C 6 -C, 2 ) -aryl-(C,-C 4 ) -alkyl, (C j -C 8 ) -heteroaryl or (C 1 -C 8 -heteroaryl-(C j -C 4 ) -alkyl, in which in the last seven named groups, optionally at least one of the conditions b) , c) , e) , g) and h) defined for these groups and the following conditions are fulfilled:
  • R 3 ' and B are as defined above;
  • R 5 is hydrogen, (C
  • R 5 and R 6 form the above defined ring
  • 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
  • R 7 + R 8 , R 7 + R 10 or R s + R 10 form the above defined ring
  • p is as defined above, as well as their salts, especially acid addition salts.
  • R 1 and R 2 which are the same or different and independently of each other, are (C j -C 12 )-alkyl, (C 2 -C 12 ) -alkenyl, (C 2 -C 12 )-alkynyl, (C 6 -C 12 ) -aryl, (C 7 -C 13 ) -aralkyl, (C j -C 12 )-alkoxy, (C 2 -C I2 )-alkenyloxy, (C,-C 12 ) -alkynyloxy, (C [ -C 12 )-alkylthio, (C 6 -C 12 )- aryloxy, (C 7 -C 13 ) -arylalkoxy, (C 7 -C 13 ) -arylalkylthio, (C 6 -C p ) -arylthio, heteroaryl, heteroaryl-(C j
  • R 5 and R 6 independently of each other are hydrogen
  • R 7 is hydrogen, (C
  • R 8 , R 9 , R 10 and R 11 which are the same or different and independently of each other, are F, Cl, Br, I, CN or have the same meaning as 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 independently of each other, are (C j -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 3 -C 6 ) -alkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cycloalkenyl, (C 3 -C 6 ) -alkoxy, benzyloxy, (C
  • (C 3 -C 7 ) -halocycloalkylthio especially fluoroalkylthio, CN, OH, N0 2 , F, Cl, Br, I, C0 2 R 3 , OCOR 3 , COR 3 , NR 3 COR 4 , NR R 4 , S0 3 R 3 , S0-,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 0, and R 3 and R 4 have the meanings given above;
  • R 5 and R 6 which are the same or different and independently of each other, are hydrogen, (C C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cycloalkenyl, phenyl, heteroaryl, 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, (C,-C 6 ) -hydroxyalkyl, (C,-C 6 ) -haloalkyl, (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 7 is hydrogen, (C j -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl,
  • R 8 , R 9 , R !0 and R 11 which are the same or different and independently of each other, are F, Cl, Br, I or CN or have the same meaning as 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 is (C [ -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 3 -C 6 ) -alkynyl, (C 3 -C 7 ) -cycloalkyl, (C -C 7 ) -cycloalkenyl, phenyl, (C,-C 6 ) -haloalkyl, (C-,-C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C,-C 6 ) -haloalkoxy, (C 2 -C 6 ) -haloalkenyloxy, (C 3 -C 6 ) -haloalkynyloxy, (C 3 -C 7 ) -cycloalkyloxy, (C j -C 6 ) -haloalkylthio, (C 2 -C 6 ) -haloalkenylthio
  • R 2 is (C j -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 3 -C 6 ) -alkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cycloalkenyl, (C j -C 6 ) -alkoxy, benzyloxy, (C,-C 6 ) -alkylthio, phenoxy, phenylthio, (C 2 -C 6 ) -alkenyloxy, (C 3 -C 6 ) -alkynyloxy, (C 7 -C 13 ) -phenylalkoxy, (C 7 -C 13 ) -phenylalkylthio, (C [ -C 6 ) -haloalkyl, (C
  • 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 j -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;
  • C j -C 4 -alkoxy especially methoxy or ethoxy, and preferably with the R 2 in the 3 and 4 positions. It is especially preferred that 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.
  • cycloalkyl v/hich is mono- bi- or tricyclic, preferably onocyclic, is to be understood, e.g.
  • alkyl under the term “alkoxyalkyl” is to be understood for example 1-methoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, ethoxymethyl, ethoxy ethyl, 3-methoxypropyl or 4- butoxybutyl; under the term “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 , CF 2 CHF 2 , CC1 3 , CC1 2 F, CF 2 CF 2 CF 3 , CF 2 CHFCF 3 , CH 2 CF 3 , (CF 2 ) 3 CF 3 , CF 2 H, CHF 2 , CH 2 C1, CHC1-, or CCl 3 CH ⁇ and correspondingly for haloalkenyl, haloalkynyl and the like; under the
  • Examples of such groups are thienyl, furyl, benzofuryl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl and tetrazolyl; under the term “cycloalkoxy” is to be understood a cycloalkoxy group, whose hydrocarbon group has the meaning given under the term “alkyl”; under the term “alkythio-alkyl” is to be understood for example methylthiomethyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, 2-ethylthioethyl or 3-methylthiopropyl; under the term “alkenyl” is to be understood, e.g.
  • alkynyl is to be understood, e.g. ethynyl, propargyl, 2-butynyl or 2-pentynyl.
  • the invention includes all stereoiso ers, 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.
  • the following acids can be considered: 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 dissolving in an organic solvent and addition of the acid, and purified in known manner, for example by filtering, isolation and optionally washing with an inert solvent.
  • Base addition salts can be obtained by treatment with alkali or alkaline earth metal hydroxides or carbonates or with an organic amine.
  • the amines can be obtained in known manner as described for example in Bull. Chem. Soc. Jap. 1990, _6_1, 1252; Angew. Chem. 1989, 101. 202 and 1992, 104, 914; Heterocycles, 1987, _2_6, 1595 and J. Med. Chem.
  • 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 equivalents, per 1 equivalent of dioxolane of formula IX.
  • the reaction is optionally carried out in an inert 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, dimethoxyethane, toluene, xylene, chlorobenzene, hexane, cyclohexane, heptane, petroleum ether, acetone, methyl ethyl ketone, dichloromethane, 1, 2-dichloroethane, methanol or ethanol.
  • 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 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, p-toluenesulfonic acid or O-ethyl or O-isobutylcarbonic acid or their N-hydroxyimide esters.
  • alkyl, aryl or arylalkyl esters such as the methyl, ethyl, phenyl or benzyl ester
  • their imidazolides such as the acid chloride or bromide
  • their anhydrides their mixed anhydrides with aliphatic or aromatic carboxylic,
  • acid activating and/or dehydrating agents are chlorinated carbonic acid esters, such as ethyl chloroformate, isobutyl chlorofor ate, phosphorous pentoxide, N,N'-dicyclohexylcarbodiimide, N,N'-carbonyldiimide, N,N'-carbonyldiimidazole or N,N'-thionyldiimide.
  • chlorinated carbonic acid esters such as ethyl chloroformate, isobutyl chlorofor ate, phosphorous pentoxide, N,N'-dicyclohexylcarbodiimide, N,N'-carbonyldiimide, N,N'-carbonyldiimidazole or N,N'-thionyldiimide.
  • titanium tetraalkoxides such as titanium tetraisopropylate, titanium tetraethylate, titanium tetramethylate, titanium tetrapropylate or by the use of increased pressure (Angew Chemie, (1986) , 6, 569).
  • the 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.
  • a solvent or mixture of solvents such methylene chloride, chloroform, carbon tetrachloride, ether, tetrahydrofuran, dioxane, benzene, toluene, acet
  • the compounds of the invention of formula I are characterised by an excellent fungicidal activity against phytopathogenic fungi.
  • the compounds are especially valuable for their curative activity. This is especially important and advantageous in such fungal diseases that cannot be controlled effectively with conventional fungicides.
  • 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 lubricating agents for metal working, or as preservatives in boring and cutting oils.
  • compositions of the invention contains generally from 1 to 95 % by weight of the active ingredient.
  • WP wettable powders
  • EC e ulsifiable concentrates
  • SC aqueous dispersions in oil or water based
  • SC suspoemulsions
  • DP dusting powders
  • WG water-dispersible granules
  • ULV-formulations rr.icrocapsules, waxes or baits.
  • the necessary formulation additives are also known as inert materials, surfactants, solvents and other additives and are described for example in: Watkins, "Handbook of Insecticide Dust Diluents and Carrier", 2nd Clay Colloid Chemistry, 2nd Ed., J. Wiley & Sons, N. Y.; Marschen, “Solvents Guide”, 2nd Ed., Interscience, N. Y. 1950; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N. J. ; Sisley and Wood, “Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N. Y.
  • 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 ligninsulfonates, sodium 2 , 2'-dinaphthyl-methane- 6, 6'-disulfonate, sodium dibutylnapthalenesulfonate or and also sodium salt of oleylmethyltaurine.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g.
  • 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.
  • alkylarylsulfonic acids such as calcium dodecylbenzenesulfonate or non-ionic emulsifiers
  • 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 polyacrylates or mineral oils onto the surfaces of carriers such as sand, kaolinite or of granulated inert material.
  • Suitable active ingredients can also be granulated in the usual manner for the preparation of fertiliser granules optionally in mixture with fertiliser.
  • the active ingredient concentration is for example around 10-9%, the rest of up to 100% comprising conventional formulation parts.
  • the active ingredient concentration is around 5-80%. Dusting formulations contain at most 5-20%.
  • 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 materials, fillers and etc are used.
  • 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 combination with other fungicides known in the literature.
  • the compounds of the invention can be combined with most known fungicides including for example: a compound selected from (i) a conazole steroid demethylation inhibitor, (ii) a steroid reduction inhibitor based on a l-[3-(4-tert-butylphenyl) -2-methylpropyl] group which is attached via the N-atom to piperidine or 2, 6-dimethylmorpholine (i ⁇ ) a dithiocarbamate fungicide
  • a phthalimide fungicide in which a chloroalkylthio group is attached via the N-atom to the optionally hydrogenated phthalimide group, (v) an anilide fungicide (vi) an mbc fungicide.
  • fungicide selected from the group consisting of chlorothalonil , dimethomorph, fenpiclonil, fluazinam, hymexazol, nuarimol, pencycuron, pyrifenox, thicyofen, probenazole, pyroquilon, tricyclazole, quaternary ammonium compounds, fludioxonil, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one (and mixtures of these two) , furmecyclox, 3-iodo-2-propynyl butylcarbamate and sulfur.
  • Conazoles are defined in ISO standard 257 as compounds based on i idazole 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, cyproconazole, diniconazole, fenbuconazole, imibenconazole, furconazole, tetraconazole, myclobutanil, penconazole, fluquinconazole, azaconazole, imazalil, triflumizole, epoxiconazole, triticonazole, metconazole and the fungicide having the code No SSF 109. Examples of type (ii) fungicides include fenpropimorph and fenpropidin.
  • type (iii) fungicides include ancozeb and thiram.
  • type (iv) fungicides include folpet, captafol and captan.
  • type (v) fungicides include a) 3 ' , 5'-dichloroanilide fungicides in which the 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, d) benzanilide fungicides, e.g. flutolanil, and e) 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-coppe , 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 methoxyi ino substituent.
  • the aryl group is usually a 2-substituted phenyl group.
  • Examples of such compounds are those disclosed in a wide number of patent applications, including EPS 178326, 203606, 203608, 206523, 229974, 226917, 242070, 242081, 243012, 243014, 251082, 256667, 260794, 260832, 267734, 270252, 273572, 274825, 278595, 291196, 299694, 307101, 307103, 310954, 312221, 312243, 329011 and 336211.
  • Specific compounds are those having the having the code Nos BAS 490F and ICIA 5504.
  • Examples of type (xi) fungicides include pyrimethanil, cyprodinil and mepanipyrim.
  • type (xii) fungicides include pyrazophos, fosetyl aluminium and tolclofos-methyl.
  • the names quoted for these compounds are the non- proprietary common names and the chemical structure can be found for example by reference to the "Pesticide Manual", ninth edition, 1991, published by the British Crop Protection Council or in other recent publications.
  • 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, ne aticides or herbicides.
  • active ingredients such as insecticides, desiccating agents, sterilants, acaricide, ne aticides or herbicides.
  • insecticides include phosphorus acid esters, carbamates, carboxylates, formamidine, tin compounds, compounds prepared from microorganisms, etc.
  • Preferred mixing partners are:
  • 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, preferably between 0.001 and 1% by weight.
  • the application is carried out in conventional manner adapted to the particular application form. The following examples illustrate the invention, without being limiting in any way.
  • a dusting composition was obtained by mixing 10 parts by weight active ingredient and 90 parts by weight talc as inert ingredient and micronising in a hammer mill.
  • a wettable powder, easily dispersible in water was obtained by mixing 25 parts by weight active ingredient 65 parts by weight kaolin containing quartz as inert ingredient, 10 parts by weight potassium lignin sulfonate and 1 part by weight sodium salt of oleylmethyltaurine as wetting and dispersing agents and milled in a pinned disk mill.
  • a dispersible concentrate, easily dispersible in water was prepared by mixing 40 parts by weight active ingredient with 7 parts by weight of a sulfosuccinate half ester, 2 parts by weight sodium ligninsulfonate and 51 parts by weight water and milling to below 5 microns in grinding ball mill.
  • An emulsifiable concentrate was prepared from 15 parts by weight active ingredient, 75 parts by weight cyclohexanone as solvent and 10 parts by weight nonylphenolethoxylate (10 AeO) as emulsifier.
  • a granulate was prepared from 2 to 15 parts by weight active ingredient and an inert granulate carrier material such as attapulgite, pumice granules and/or quartz sand.
  • an inert granulate carrier material such as attapulgite, pumice granules and/or quartz sand.
  • 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.
  • Tri ethylsilyl 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 temperature.
  • This product was added to nitrogen purged dry methanol (50 ml), followed by solid sodium methoxide (0.29 g) .
  • the mixture was agitated for 5 hours, poured into dilute hydrochloric acid, the organic layer, evaporated and extracted with ethyl acetate/water and the organic layer washed with water, dried and evaporated to give 0.48 g of the title product, as an oil.
  • 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 temperature and 1,3-dimethyl-3,4,5,6-tetrahydro-2(Iff)- pyri idineone (5.12 g) in tetrahydrofuran (15 ml) was added.
  • the compound of the invention was subjected to various tests.
  • the compound was assessed for activity against Phvtophthora infestans (late tomato blight - PI) and Plasmooara 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 infection of the leaf surface was visually estimated. The following compounds of the invention gave 100% control at 500 ppm or less against one or both of these diseases.

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyridine Compounds (AREA)

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

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4319887A DE4319887A1 (de) 1993-06-16 1993-06-16 Arylacetamide, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Fungizide
DE4319887 1993-06-16
PCT/EP1994/001938 WO1994029267A1 (fr) 1993-06-16 1994-06-14 Arylacetamides, leur procede de preparation, compositions les contenant et leur utilisation en tant que fongicides

Publications (1)

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EP0703899A1 true EP0703899A1 (fr) 1996-04-03

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EP94920452A Withdrawn 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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EP (1) EP0703899A1 (fr)
JP (1) JPH08511772A (fr)
CN (1) CN1128019A (fr)
AU (1) AU7123994A (fr)
DE (1) DE4319887A1 (fr)
HU (1) HUT73352A (fr)
IL (1) IL110037A0 (fr)
WO (1) WO1994029267A1 (fr)

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DE19512617A1 (de) * 1995-04-05 1996-10-10 Bayer Ag Hydrazonoessigsäureamide
DE19642863A1 (de) * 1996-10-17 1998-04-23 Bayer Ag Amide
FR2761986B1 (fr) * 1997-04-09 1999-05-21 Hoechst Schering Agrevo Sa Nouveaux amides aromatiques, leur procede de preparation et leur application comme pesticides
TW564244B (en) 1999-01-11 2003-12-01 Novartis Ag Novel propargylether derivatives
GB0011944D0 (en) * 2000-05-17 2000-07-05 Novartis Ag Organic compounds
UA75093C2 (en) 2000-10-06 2006-03-15 Dimensional Pharm Inc Aminopyridinyl-,aminoguanidinyl-, and alkoxyguanidinesubstituted phenylsubstituted phenylacetamides as protease inhibitors
GB0127557D0 (en) * 2001-11-16 2002-01-09 Syngenta Participations Ag Organic compounds
GB0127556D0 (en) * 2001-11-16 2002-01-09 Syngenta Participations Ag Organic compounds
GB0127554D0 (en) * 2001-11-16 2002-01-09 Syngenta Participations Ag Organic compounds
GB0127559D0 (en) * 2001-11-16 2002-01-09 Syngenta Participations Ag Organic compounds
GB0217211D0 (en) * 2002-07-24 2002-09-04 Syngenta Participations Ag Organic compounds
GB0223665D0 (en) * 2002-10-10 2002-11-20 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
US9120744B2 (en) 2007-04-16 2015-09-01 The Regents Of The University Of Michigan Plasminogen activator inhibitor-1 inhibitors and methods of use thereof to modulate lipid metabolism
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
PT2871180T (pt) 2012-07-04 2018-05-08 Agro Kanesho Co Ltd Derivado de éster do ácido 2-aminonicotínico e bactericida que o contém como ingrediente ativo
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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
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Also Published As

Publication number Publication date
HUT73352A (en) 1996-07-29
DE4319887A1 (de) 1994-12-22
WO1994029267A1 (fr) 1994-12-22
AU7123994A (en) 1995-01-03
JPH08511772A (ja) 1996-12-10
CN1128019A (zh) 1996-07-31
IL110037A0 (en) 1994-10-07
HU9503609D0 (en) 1996-02-28

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