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EP1608637A1 - Anilide d'acide carboxylique trifluoromethylthiophene et son utilisation en tant que fongicide - Google Patents

Anilide d'acide carboxylique trifluoromethylthiophene et son utilisation en tant que fongicide

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Publication number
EP1608637A1
EP1608637A1 EP04722169A EP04722169A EP1608637A1 EP 1608637 A1 EP1608637 A1 EP 1608637A1 EP 04722169 A EP04722169 A EP 04722169A EP 04722169 A EP04722169 A EP 04722169A EP 1608637 A1 EP1608637 A1 EP 1608637A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
substituted
halogen
phenyl
alkenyl
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Withdrawn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
EP04722169A
Other languages
German (de)
English (en)
Inventor
Markus Gewehr
Bernd Müller
Thomas Grote
Wassilios Grammenos
Andreas Gypser
Jordi Tormo I Blasco
Anja Schwögler
Joachim Rheinheimer
Carsten Blettner
Frank Schieweck
Michael Rack
Ulrich Schöfl
Siegfried Strathmann
Reinhard Stierl
Jan Rether
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP1608637A1 publication Critical patent/EP1608637A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms

Definitions

  • Trifluoromethyl-thiophenecarboxylic acid anilides and their use as fungicides
  • the present invention relates to
  • R independently of one another CC 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 -
  • Phenyl, phenyl-C C 6 alkyl, phenyl-C 2 -C 6 alkenyl, phenyl-C 2 -C 6 alkynyl, phenyloxy-Ci-C6 alkyl, phenoxy-C 2 -C 6 -AI kenyl, phenyloxy-C 2 -C 6 -AI kinyl, where the alkyl, alkenyl and alkynyl part can be substituted by R 7 and the phenyl ring by R 5 ; -C (R 8 ) NOR 6 ; XO, S or direct bond; R 5 H, -CC 4 alkyl, C 3 -C 6 cycloalkyl, CC 4 alkoxy, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, where these groups can be substituted by halogen, halogen , nitro, CN, phenyl which may be substituted with R 1, phen
  • the present invention relates to the use of the trifluoromethylthiophenecarboxanilides as fungicides and agents containing them.
  • Thiophene carboxylic acid anilide derivatives are known from JP 08092223, JP 092592, JP 092593, JP 01302605, JP 01313402, EP-A 915868 and WO 02/08197.
  • the object of the present invention was to provide new thiophene carbonate anilide derivatives with improved activity, in particular even at low application rates.
  • the organic molecule parts mentioned in the definition of the substituents R 1 to R 8 - like the meaning halogen - are collective terms for individual lists of the individual group members. All carbon chains, that is to say all alkyl, halogenoalkyl, arylalkyl, alkenyl, Haloalkenyl, alkynyl and haloalkynyl parts can be straight or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms. Halogen is fluorine, chlorine, bromine or iodine.
  • CC 4 alkyl and the CC 4 alkyl parts in CC 4 alkoxy for: CH 3 , C 2 H 5 , CH 2 -C 2 H 5 , CH (CH 3 ) 2 , n-butyl, CH (CH 3 ) - C 2 H5, CH 2 -CH (CH 3 ) 2 or C (CH 3 );
  • dC -alkyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CH 2 F, CHF 2 , CF 3 , CH 2 CI, CH (CI) 2 , C (CI) 3 , chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,
  • 2,2,2-trichloroethyl, C 2 F 5 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl , 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-tri-chloropropyl, CH 2 -C 2 F Sl CF 2 -C 2 F 5 , 1 - (fluoromethyl) -2-f luorethyl, 1 - (chloromethyl) -2-chloroethyl, 1 - (bromomethyl) -2-bromethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;
  • C 1 -C 1 -alkyl and the C 1 -C 8 -alkyl parts in C 1 -C 8 -alkoxy for a CrC 4 -alkyl radical as mentioned above, or for, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl , 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1 -dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,
  • -C 8 haloalkoxy for a CrC 12 alkyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for one of the radicals mentioned under dC -haloalkyl or for 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5- Trichloro-1-penyl, undecafluoropentyl, 6-fluoro-1-hexyl, 6-chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1-hexyl, 6,6,6-trichloro 1 -hexyl or dodecafluorohexyl;
  • - C 2 -C 4 alkenyl unsaturated, straight-chain or branched hydrocarbon residues with 2 to 4 carbon atoms and a double bond in any one Position, e.g. ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-buten-1-yl, 1-buten-2-yl, 1-buten-3-yl, 2-buten-1-yl, 1 -Methyl-prop-1-en-1-yl, 2-methyl-prop-1-en-1-yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-ene -1 -yl;
  • C 2 -C 4 -Halogenalkenyl for unsaturated, straight-chain or branched hydrocarbon radicals with 2 to 4 carbon atoms and a double bond in any position (as mentioned above), the hydrogen atoms in these groups being partially or completely against halogen atoms as mentioned above, in particular fluorine , Chlorine and bromine are replaced, for example 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2- Bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;
  • C 2 -C 2 haloalkenyl and the haloalkenyl parts of C 2 -C 8 haloalkenyloxy for C 2 -C 2 alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for the radicals mentioned for C 2 -C 4 haloalkenyl;
  • C 2 -Ci 2 alkynyl and the C 2 -C 8 alkynyl parts in C 2 -C 8 alkynyloxy for straight-chain or branched hydrocarbon groups having 2 to 12 carbon atoms and a triple bond in any position for example ethynyl, prop-1-in -1-yl, prop-2-yn-1-yl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-BuM-yn-4-yl, n -But-2-in-1-yl, n-pent-1 -in-1 -yl, n-pent-1 -in-3-yl, n-pent-1 -in-4-yl, n-pent -1-in-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methyl-but -1-
  • C 2 -C 4 -Halogenalkynyl for unsaturated, straight-chain or branched hydrocarbon radicals with 2 to 4 carbon atoms and a triple bond in any position (as mentioned above), the hydrogen atoms in these groups being partially or completely against halogen atoms as mentioned above, in particular fluorine , Chlorine and bromine can be replaced, for example 1, 1-difluoroprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobutyl-2-yn-1-yl, 1 , 1-difluorobut-2-in-1-yl, 5-fluoropent-3-in-1-yl or 6-fluorohex-4-in-1-yl;
  • C 2 -C 2 haloalkynyl and the C 2 -C 8 haloalkynyl parts in C 2 -C 8 haloalkynyloxy for C 2 -C 12 alkynyl as mentioned above, partially or completely by fluorine, chlorine, bromine and / or iodine is substituted, for example for the radicals mentioned for C 2 -C 4 -haloalkynyl;
  • CC 4 alkoxy for OCH 3 , OC 2 H 5 , OCH 2 -C 2 H 5 , OCH (CH 3 ) 2 , n-butoxy, OCH (CH 3 ) - C 2 H 5 , OCH -CH (CH 3 ) 2 or C (CH 3 ) 3 , preferably for OCH 3 , OC 2 H 5 or OCH (CH 3 ) 2 ;
  • CrC -haloalkoxy for a dC 4 -alkoxy radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CI, OCH (CI ) 2) OC (CI) 3) chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2 - fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-
  • d-Cs-alkoxy for a -CC 4 alkoxy radical as mentioned above, or for example n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 1 -
  • CrC 8 haloalkoxy for a CrC 8 alkoxy radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example one of the radicals mentioned under dC haloalkoxy or for 5-fluorine
  • C 3 -Ci 2 -cycloalkyl for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl;
  • PhenyI -CC 6 alkyl for CrC 6 alkyl which is substituted with phenyl, for example for benzyl, 1- or 2-phenylethyl, 1-, 2- or 3-phenylpropyl; Phenyloxy-dC 6 -alkyl: for d-C ⁇ -alkyl which is substituted with phenoxy, for example for phenoxymethyl, 1- or 2-phenoxyethyl, 1-, 2- or 3-phenoxypropyl;
  • Phenyl-C 2 -C 6 -alkenyl for C -C 6 - alkenyl which is substituted by phenyl, for example for 1 - or 2-phenylethenyl, 1 -Phenylprop-2-en-1-yl, 3-phenyl- 1-propen-1-yl, 3-
  • Phenyl-C 2 -C 6 -alkynyl for C 2 -C 6 -alkynyl which is substituted with phenyl, for example for 1-phenylprop-2-yn-1-yl, 3-phenyl-1-propyne-1- yl, 3-phenyl-2-propin-1-yl, 4-phenyl-1-butin-1 -yl or 4-phenyl-2-butyn-1-yl.
  • R 1 is halogen or dC-alkyl, which can be substituted by halogen, particularly preferably fluorine, chlorine, bromine or methyl;
  • R 2 is H, methyl, OH or methoxy
  • alkynyl these groups can be substituted by halogen and C 1 -C 4 -alkyl;
  • Phenyl, phenyl-dC 6 -alkyl, where the phenyl ring can be substituted by R 5 ; or -C (dC 4 -alkyl) NO-R 6 , where the CC 4 -alkyl group can be substituted by halogen;
  • X is a direct bond or O, particularly preferably a direct bond, further particularly preferably O;
  • R 4 halogen, dC 4 alkyl, dC 4 alkoxy, where these groups can be substituted by halogen, particularly preferably fluorine, chlorine, methyl, trifluoromethyl or methoxy, trifluoromethoxy, difluoromethyl;
  • R 5 H dC -alkyl, C 3 -C 6 -cycloalkyl, C r C 4 -alkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, where these groups can be substituted by halogen, halogen, nitro, CN, phenyl which may be substituted with R 1, phenoxy which may be substituted me R 1, 6 -alkyl-phenyl, wherein the alkyl portion can be substituted by halogen and the phenyl ring may be substituted with R 1; R 6 CC alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, where these groups may be substituted by halogen, phenyl which may be substituted by R 1 ;
  • R 7 CC 4 alkyl, CC 8 alkoxy, C 2 -C 8 alkenyloxy, C 2 -C 8 alkynyloxy, CC 4 alkoxy-d- C 8 alkoxy, where these groups can be substituted by halogen, halogen ;
  • Phenyl which may be substituted with R 5 ; n 0-4, preferably 0.1, particularly preferably 0; m 0.1, particularly preferably 0.
  • Trifluoromethyl-thiophenecarboxanilides of the general formulas Ia, Ib, IIIa, IIb, lilac and IIIb are particularly preferred
  • R 3 C r C 12 alkyl, C 3 -C 12 cycloalkyl, C 2 -C 12 alkenyl, C 5 -C 12 cycloalkenyl, C 2 -C 12 -
  • alkynyl these groups can be substituted by halogen or CC 4 alkyl;
  • CC 4 alkyl NO-R 6 , where the CC 4 alkyl group can be substituted by halogen;
  • X is a direct bond or O, particularly preferably a direct bond, further particularly preferably O.
  • R 1 is H, R 1 'is methyl, X is a direct bond and R 3 has the meaning given in Table A.
  • R for H, R 1 ' for fluorine, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is H, R 1 is chlorine, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is methyl, R 1 'is methyl, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is methyl, R 1 'is fluorine, X is a direct bond and R 3 is one in the table
  • R is methyl, R 1 'is chlorine, X is a direct bond and R 3 is one in the table
  • R 1 is fluorine, R 1 'is H, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is fluorine, R 1 'is chlorine, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is chlorine, R 1 'is H, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is chlorine, R 1 'is methyl, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is chlorine, R 1 'is chlorine, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is H, R 1 'is methyl, X is O and R 3 has the meaning given in Table A.
  • R 1 represents H
  • R 1 represents fluorine
  • X represents O
  • R 3 has the meaning given in Table A.
  • R 1 is H, R 1 'is chlorine, X is O and R 3 has the meaning given in Table A.
  • R 1 is methyl, R 1 'is H, X is O and R 3 has a meaning given in Table A.
  • R 1 is methyl, R 1 'is fluorine, X is O and R 3 has the meaning given in Table A.
  • R 1 is methyl, R 1 'is chlorine, X is O and R 3 has the meaning given in Table A.
  • R 1 is fluorine, R 1 'is H, X is O and R 3 has the meaning given in Table A.
  • R 1 is fluorine, R 'is methyl, X is O and R 3 has the meaning given in Table A.
  • R 1 is fluorine, R 1 'is fluorine, X is O and R 3 has a meaning given in Table A.
  • R 1 represents chlorine, R 1 'represents H, X represents O and R 3 has the meaning given in Table A.
  • R 1 is chlorine, R 1 'is methyl, X is O and R 3 has the meaning given in Table A.
  • R 1 is chlorine, R 1 'is fluorine, X is O and R 3 has the meaning given in Table A.
  • R 1 is chlorine, R 1 'is chlorine, X is O and R 3 has a meaning given in Table A.
  • R 1 is H, R 1 'is methyl, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 for H, R 1 ' for fluorine, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is H, R 1 'is chlorine, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is methyl, R 1 is methyl, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is methyl, R 1 'is chlorine, X is a direct bond and R 3 is one in the table
  • R 1 is fluorine, R 1 'is H, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is fluorine, R 1 'is methyl, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is fluorine
  • R r is chlorine
  • X is a direct bond
  • R 3 has the meaning given in Table A.
  • R 1 is chlorine, R 1 'is H, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is chlorine, R 1 'is methyl, X is a direct bond and R 3 is one in the table
  • R 1 is chlorine, R 1 'is fluorine, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is chlorine, R 1 'is chlorine, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 represents H
  • X represents O
  • R 3 has the meaning given in Table A.
  • R 1 is H, R 1 'is chlorine, X is O and R 3 has the meaning given in Table A.
  • R 1 is methyl, R 1 'is H, X is O and R 3 has a significance given in Table A ⁇ processing.
  • R 1 is methyl, R 1 'is methyl, X is O and R 3 is one given in Table A.
  • R 1 is methyl, R 1 'is fluorine, X is O and R 3 has a meaning given in Table A.
  • R 1 is fluorine, R 1 'is H, X is O and R 3 has the meaning given in Table A.
  • R 1 is fluorine, R 1 'is methyl, X is O and R 3 has the meaning given in Table A.
  • R 1 is fluorine, R 1 'is fluorine, X is O and R 3 has the meaning given in Table A.
  • R 1 is fluorine, R 1 'is chlorine, X is O and R 3 has a meaning given in Table A.
  • R 1 stands for chlorine
  • R 1 ' for H
  • X for O
  • R 3 has the meaning given in Table A.
  • R is chlorine, R 1 'is fluorine, X is O and R 3 has the meaning given in Table A.
  • R 1 is chlorine, R 1 'is chlorine, X is O and R 3 has the meaning given in Table A.
  • R 1 is H, R 1 'is methyl, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is H, R 1 'is chlorine, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is methyl, R 1 'is H, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is methyl, R 1 'is methyl, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is methyl, R 1 'is chlorine, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is fluorine, R 1 'is H, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is fluorine, R 1 'is methyl, X is a direct bond and R 3 is one in the table
  • R 1 is fluorine, R 1 'is fluorine, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is fluorine, R 1 'is chlorine, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is chlorine, R 1 'is methyl, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is chlorine, R 1 'is fluorine, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is chlorine, R 1 'is chlorine, X is a direct bond and R 3 has the meaning given in Table A.
  • R 1 is H, R 1 'is methyl, X is O and R 3 has the meaning given in Table A.
  • R 1 stands for H, R 1 ' for fluorine, X for O and R 3 has a meaning given in Table A.
  • R 1 is methyl, R 1 'is H, X is O and R 3 has the meaning given in Table A.
  • R 1 is methyl, R 1 'is methyl, X is O and R 3 is one given in Table A.
  • R 1 is methyl, R 1 'is fluorine, X is O and R 3 has the meaning given in Table A.
  • R 1 is methyl, R 1 'is chlorine, X is O and R 3 has a meaning given in Table A.
  • R 1 is fluorine, R 1 'is H, X is O and R 3 has a meaning given in Table A.
  • R 1 is fluorine, R 1 'is fluorine, X is O and R 3 has the meaning given in Table A.
  • R 1 is fluorine, R 1 'is chlorine, X is O and R 3 has the meaning given in Table A.
  • R 1 represents chlorine, R 1 'represents H, X represents O and R 3 has the meaning given in Table A.
  • R 1 is chlorine, R 1 'is methyl, X is O and R 3 has a meaning given in Table A.
  • R 2 is methyl
  • X is a direct bond
  • R 3 has a meaning given in Table A.
  • R 2 stands for OH
  • X stands for a direct bond
  • R 3 has the meaning given in Table A.
  • R 2 is methyl, X is O and R 3 has the meaning given in Table A.
  • R 2 is methoxy, X is O and R 3 has the meaning given in Table A.
  • R 2 stands for OH
  • X stands for a direct connection
  • R 3 has a meaning given in Table A.
  • R 2 is methyl, X is O and R 3 has the meaning given in Table A.
  • R 2 is methoxy, X is O and R 3 has the meaning given in Table A.
  • R 2 is methyl
  • X is a direct bond
  • R 3 has a meaning given in Table A.
  • R 2 stands for OH
  • X stands for a direct bond
  • R 3 has the meaning given in Table A.
  • R 2 is methoxy
  • X is a direct bond
  • R 3 has the meaning given in Table A.
  • R 2 is methyl, X is O and R 3 has the meaning given in Table A.
  • R 2 stands for OH
  • X stands for O
  • R 3 has the meaning given in Table A.
  • R 2 is methoxy, X is O and R 3 has the meaning given in Table A.
  • the active ingredients I, II and III can be prepared by processes known from the literature by reacting activated trifluorothiophenecarboxylic acid derivatives IV with an aniline V [Houben-Weyl: “Methods of organ. Chemie ", Georg-Thieme-Verlag, Stuttgart, New York 1985, Volume E5, pp. 941-1045.].
  • Activated carboxylic acid derivatives are, for example, halides, active esters, anhydrides, azides, for example chlorides, fluorides, bromides, para-nitrophenyl esters, pentafluorophenyl esters , N-hydroxysuccinimide ester, hydroxybenzotriazol-1-yl ester.
  • the active ingredients I, II and III can be prepared by reacting the acids VI with an aniline V in the presence of a coupling reagent.
  • Coupling reagents can be, for example:
  • Coupling reagents based on carbodiimide e.g. N, N'-dicyclohexylcarbodiimide
  • Coupling reagents that form mixed anhydrides with carbonic acid esters for example 2-ethoxy-1-ethoxycarbonyl-1, 2-dihydroquinoline [B. Belleau, G. Malek, J. Amer. Chem. Soc. 1968, 90, 1651.], 2-iso-butyloxy-1-iso-butyloxycarbonyl-1, 2-dihydroquinoline [Y. Kiso, H. Yajima, J. Chem. Soc, Chem. Commun.
  • Coupling reagents based on uronium or with guanidinium N-oxide structure e.g. N, N, N ', N'-tetramethyl-O- (1 H-benzotriazol-1-yl) -uronium hexafluorophosphate [R. Knorr, A. Trazoak, W. Bannwarth, D. Gillessen, Tetrahedron Lett. 1989, 30, 1927.]
  • N, N, N ', N'-tetramethyl-O- (benzotriazol-1-yl) uronium tetrafluoroborate, (benzotriazol-l-yloxy) dipiperidinocarbenium hexafluorophosphate S. Chen, J. Xu, Tetrahedron Lett. 1992, 33, 647.
  • Coupling reagents that form acid chlorides e.g. Phosphoric acid bis (2-oxo oxazolidide) chloride [J. Diago-Mesequer, Synthesis 1980, 547.].
  • the trifluoromethyl-thiophenecarboxylic acids VI can be prepared by methods known from the literature [M. Nishida et.al., J. Fluorine Chem. 1990, 46, 445. JP 1980-5059135. DE 3620064. US 4803205. W. Dmowski, K. Piasecka, J. Fluorine Chem. 1996, 78, 59.].
  • the activated thiophenecarboxylic acid derivatives IV can be synthesized therefrom by methods known from the literature [Houben-Weyl: “Methods of organ. Chemistry ", Georg Thieme Verlag, Stuttgart, New York 1985, Volume E5, pp. 587-614, 633-772.]
  • anilines V can be synthesized by methods known from the literature [Houben-Weyl: “Methods of organ. Chemistry ", Georg Thieme Verlag, Stuttgart, New York, Volume XI, Part 1, pp. 9-1005.]
  • the compounds I, II and III are suitable as fungicides. They are characterized by excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them are systemically effective and can be used in plant protection as leaf and soil fungicides.
  • Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines
  • Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Erysiphe graminis (powdery mildew) on cereals, Fusarium and Verticillium species on various plants, Helminthosporium species on cereals,
  • Rhizoctonia species on cotton, rice and lawn are Rhizoctonia species on cotton, rice and lawn.
  • Venturia species scab on apples and pears.
  • the compounds I, II and III are also suitable for combating harmful fungi such as Paecilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
  • harmful fungi such as Paecilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
  • the compounds I, II and III are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds.
  • the application can take place both before and after the infection of the materials, plants or seeds by the fungi.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
  • the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kg of seed are generally required.
  • the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates in material protection are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active ingredient per cubic meter of treated material.
  • the compounds I, II and III can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, where in the case of water as a diluent other organic solvents can also be used as auxiliary solvents.
  • auxiliaries solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g.
  • Carriers such as natural powdered rock (e.g. kaolins, clays, talc, chalk) and synthetic powdered rock (e.g. highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • Carriers such as natural powdered rock (e.g. kaolins, clays, talc, chalk) and synthetic powdered rock (e.g. highly disperse silica, silicates)
  • Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste
  • Suitable surfactants are alkali metal, alkaline earth metal salts, sulfonic acid ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ethers, condensates of sulfonated naphthalene and naphthalene derivatives with Formaldehyde, condensation products of naphthalene or naphthalene sulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alky
  • Mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, are used to produce directly sprayable solutions, emulsions, pastes or oil dispersions.
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coating, I impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. Mineral soils, such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, do
  • the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • V. 80 parts by weight of a compound according to the invention are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel and grind in a hammer mill (active ingredient content 80% by weight).
  • the active substances as such in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, Suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkles, granules by spraying, atomizing, dusting, scattering or pouring can be used.
  • the application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates composed of an active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil, which are suitable for dilution with water.
  • the active ingredient concentrations in the ready-to-use preparations can be varied over a wide range. Generally they are between 0.0001 and 10%. Small amounts of active compound I are often sufficient in the ready-to-use preparation, e.g. 2 to 200 ppm. Ready-to-use preparations with active ingredient concentrations in the range from 0.01 to 1% are also preferred.
  • the active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume process
  • Oils of various types, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.
  • compositions according to the invention can also be present together with other active compounds which, e.g. with herbicides, insecticides, growth regulators, fungicides or also with fertilizers. Mixing the compounds I or the compositions containing them in the use form as fungicides with other fungicides results in an enlargement of the fungicidal spectrum of action in many cases.
  • Nitroderivate such as dinitro- (1-methylheptyl) phenylcrotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl-isopropyl carbonate, 5-nitro- isophthalate di-isopropyl; Heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, O, O-diethyl-phthalimidophosphonothioate, 5-amino-1 - [bis- (dimethylamino) phosphinyl] -3-phenyl-1, 2,4-triazole, 2,3-dicyano-1, 4-dithioanthraquinone, 2-thio-1, 3-dithiolo [4,5-b] quinoxaline, 1 - (
  • N-cyclododecyl-morpholine or its salts N- [3- (p-tert-butylphenyl) -2-methylpropyl] -cis-2,6-dimethyl-morpholine, N- [3- (p-tert.- Butylphenyl) -2-methylpropyl] piperidine, 1 - [2- (2,4-dichlorophenyl) -4-ethyl-1, 3-dioxolan-2-yl-ethyl] -1 H-1, 2,4-triazole , 1- [2- (2,4-dichlorophenyl) -4-n-propyl-1, 3-dioxolan-2-yl-ethyl] -1 H-1, 2,4-triazole, N- (n-propyl ) -N- (2,4,6-trichlorphenoxyethyl) -
  • N'-imidazol-yl urea 1 - (4-chlorophenoxy) -3,3-dimethyl-1 - (1 H-1, 2,4-triazol-1 - yl) -2-butanone, 1 - (4th -Chlorphenoxy) -3,3-dimethyl-1 - (1 H- 1, 2,4-triazol-1-yl) -2-butanol, (2RS, 3RS) -1 - [3- (2-chlorophenyl) - 2- (4-fluorophenyl) oxiran-2-ylmethyl] -1 H-1, 2,4-triazole, a- (2-chlorophenyl) -a- (4-chlorophenyl) -5-pyrimidine-methanol, 5- Butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidine, bis- (p-chlorophenyl) -3-pyridine-methanol, 1,2-bis (3-ethoxycarbonyl-2-thiour
  • Anilinopyrimidines such as N- (4,6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (1-propynyl) pyrimidin-2-yl] aniline, N- [4-methyl 6-cyclopropyl-pyrimidin-2-yl] -aniline, phenylpyrroles such as 4- (2,2-difluoro-1, 3-benzodioxol-4-yl) -pyrrole-3-carbonitrile,
  • Cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acrylic morpholide,
  • fungicides such as dodecylguanidine acetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, hexachlorobenzene, DL-methyl-N- (2,6-dimethyl-phenyl) - N-furoyl (2) alaninate, DL-N- (2,6-dimethylphenyl) -
  • N- (2'-methoxyacetyl) alanine methyl ester N- (2,6-dimethylphenyl) -N-chloroacetyl-D, L-2-aminobutyrolactone, DL-N- (2,6-dimethylphenyl) -N - (phenylacetyl) alanine methyl ester, 5-methyl-5-vinyl-3- (3,5-dichlorophenyl) -2,4-dioxo-1,3-oxazolidine, 3- [3,5-dichlorophenyl (-5-methyl -5-methoxymethyl] -1, 3-oxazolidine-2,4-dione, 3- (3,5-dichlorophenyl) -1 -isopropylcarbamoylhydantoin, N- (3,5-
  • Pepper seedlings of the "Neusiedler Ideal Elite" variety after 4-5 leaves had developed well, were sprayed to runoff point with an aqueous suspension in the active compound concentration given below.
  • the suspension or emulsion was prepared from a stock solution with 10% active compound in a mixture consisting of 85% cyclohexanone and 5% emulsifier, the plants were then cultivated for 7 days and then the treated plants were inoculated with a spore suspension of Botrytis cinerea, which contained 1.7 x 10 6 spores / ml in a 2% aqueous biomalt solution
  • Botrytis cinerea which contained 1.7 x 10 6 spores / ml in a 2% aqueous biomalt solution
  • the test plants were then placed in a climatic chamber at high atmospheric humidity at 22 to 24 ° C. After 5 days, the extent of the fungal attack on the leaves could be determined visually in% and thus not only on the fungicidal action of the substances
  • the active compounds were prepared separately as a stock solution with 0.25% by weight of active compound in 1% by weight of the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) was added to this solution and diluted with water to the desired concentration the next day, the treated plants were treated with a spore suspension of Botrytis cinerea, which contained 1.7 x 10 6 spores / ml in a 2% aqueous biomalt solution, was inoculated, and the test plants were then placed in a climatic chamber at 22 to 24 ° C. in high atmospheric humidity After 5 days, the extent of the fungal attack could be reduced Scroll visually in%.
  • Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • the suspension or emulsion was prepared from a stock solution with 10% active ingredient in a mixture consisting of 85% cyclohexanone and 5% emulsifier 20 hours after the spray coating had dried on, the plants were inoculated with an aqueous spore suspension of cucumber powdery mildew (Sphaerotheca fuliginea) and the plants were then grown in a greenhouse at temperatures between 20 and 24 ° C. and 60 to 80% relative atmospheric humidity for 7 days The extent of mildew development was then determined visually in% of the cotyledon area.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Abstract

L'invention concerne un anilide d'acide carboxylique trifluorométhylthiophène de formule I, II et III, dans lesquelles les substituants ont la signification suivante: R<1>,R<4 >signifient indépendamment l'un de l'autre alkyle C1-C4, cycloalkyle C3-C6, alcényle C2-C4, alkinyle C2-C4, alcoxy C1-C4, ces groupes pouvant être substitués par halogène, H, halogène, nitro, CN; R<2> désigne H, OH, alkyle C1-C4, cycloalkyle C3-C6, alcoxy C1-C4, ces groupes pouvant être substitués par halogène; R<3> représente alkyle C1-C12, cycloalkyle C3-C12, alcényle C2-C12, cycloalcényle C5-C12, alkinyle C2-C12, cycloalkyle C3-C12, alkyle C1-C4, ces groupes pouvant être substitués par R<7>, phényle, phényle-alkyle C1-C6, phényle-alcényle C2-C6, phényle-alkinyle C2-C6, phényloxy-alkyle C1-C6, phényloxy-alcényle -C2-C6, phényloxy-alkinyle -C2-C6, les parties alkyle, alcényle et alkinyle pouvant être substituées par R<7> et le cycle phényle par R<5>, -C(R<8>)=NOR<6>; X désigne O, S ou une liaison directe; R<5> signifie H, alkyle C1-C4, cycloalkyle C3-C6, alcoxy C1-C4, alcényle C2-C4, alkinyle C2-C4, ces groupes pouvant être substitués par halogène, halogène, nitro, CN, phényle, qui peut être substitué par R<1>, phénoxy, qui peut être substitué par R<1>, phényle-alkyle Cl-C6, la partie alkyle pouvant être substituée par halogène et le cycle phényle par R<1>; R<6> représente alkyle C1-C4, cycloalkyle C3-C6, alcényle C2-C4, alkinyle C2-C4, ces groupes pouvant être substitués par halogène, phényle, qui peut être substitué par R<1>; R<7> désigne alkyle C1-C4, alcoxy C1-C8, alcényloxy C2-C8, alkinyloxy C2-C8, alcoxy Cl-C4-alcoxy- C1-C8, ces groupes pouvant être substitués par halogène, halogène; R<8> représente H, R<7> ou alkyle C1-C12, cycloalkyle C3-C12, alcényle C2-C12, cycloalcélyne C5-C12, cycloalkyle C3-C12-alkyle-C1-C4, ces groupes pouvant être substitués par halogène; phényle, qui peut être substitué par R<5>; n est 0-4 ; m est 0, 1. La présente invention porte également sur l'utilisation de l'anilide d'acide carboxylique trifluorométhylthiophène en tant que fongicide et sur les agents le contenant.
EP04722169A 2003-03-24 2004-03-20 Anilide d'acide carboxylique trifluoromethylthiophene et son utilisation en tant que fongicide Withdrawn EP1608637A1 (fr)

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DE10313126 2003-03-24
DE10313126 2003-03-24
DE10354549 2003-11-21
DE10354549 2003-11-21
PCT/EP2004/002933 WO2004085419A1 (fr) 2003-03-24 2004-03-20 Anilide d'acide carboxylique trifluoromethylthiophene et son utilisation en tant que fongicide

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AU (1) AU2004224205A1 (fr)
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US7484564B2 (en) 2005-08-16 2009-02-03 Halliburton Energy Services, Inc. Delayed tackifying compositions and associated methods involving controlling particulate migration
WO2007024744A2 (fr) * 2005-08-21 2007-03-01 Exelixis, Inc. Composes de carboxamide heterocycliques en tant qu'agents pharmaceutiques
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KR20050115925A (ko) 2005-12-08
CL2004000611A1 (es) 2005-05-06
AR043754A1 (es) 2005-08-10
CR7977A (es) 2006-05-29
WO2004085419A1 (fr) 2004-10-07
US7501530B2 (en) 2009-03-10
CO5631439A2 (es) 2006-04-28
AU2004224205A1 (en) 2004-10-07
CA2519990A1 (fr) 2004-10-07
MXPA05009339A (es) 2005-11-04
US20060172891A1 (en) 2006-08-03
JP2006521316A (ja) 2006-09-21

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