EP1003741A1 - Substituierte herbizide tetrazolinoncarbonsäureamide - Google Patents

Substituierte herbizide tetrazolinoncarbonsäureamide

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Publication number
EP1003741A1
EP1003741A1 EP98941362A EP98941362A EP1003741A1 EP 1003741 A1 EP1003741 A1 EP 1003741A1 EP 98941362 A EP98941362 A EP 98941362A EP 98941362 A EP98941362 A EP 98941362A EP 1003741 A1 EP1003741 A1 EP 1003741A1
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EP
European Patent Office
Prior art keywords
alkyl
enyl
formula
methyl
substituted
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.)
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EP98941362A
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German (de)
English (en)
French (fr)
Inventor
Cyrill Zagar
Gerhard Hamprecht
Markus Menges
Olaf Menke
Robert Reinhard
Peter Schäfer
Karl-Otto Westphalen
Martina Otten
Helmut Walter
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BASF SE
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BASF SE
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • heterocycles can carry one or two substituents selected from a group consisting of halogen, Ci-C ⁇ -alkyl or Ci-C ⁇ -haloalkyl;
  • R 1 C ⁇ -C 6 -alkyl, C 6 haloalkyl, cyano-C ⁇ -C 4 alkyl,
  • cycloalkyl rings, cycloalkenyl rings, phenyl rings or heterocyclyl rings can each be unsubstituted or carry one to four substituents, each selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 - C 6 alkynyl, C 1 -C 4 haloalkyl, C ⁇ -C 4 -alkoxy, C 4 haloalkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 4 -alkoxycarbonyl -C-C 4 -alkoxy, -C-C 4 -alkylthio,
  • C ⁇ -C4-haloalkylthio C ⁇ -C 4 alkylsulfonyl, C 1 -C 4 halo-alkylsulfonyl, C ⁇ -C 4 alkoxycarbonyl, C ⁇ -C alkyl-carbonyl, C 1 -C 4 haloalkylcarbonyl, C 1 -C 4 alkylcarbonyloxy and C 1 -C 4 haloalkylcarbonyloxy;
  • R2 are hydrogen, C 6 -alkyl, C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 8 cycloalkyl,
  • cycloalkyl, phenyl or heterocyclyl rings are in each case unsubstituted or a 4 alkyl up to four substituents, each selected from the group consisting of halogen, cyano, nitro, C ⁇ -C, C ⁇ -C4 haloalkyl, C ⁇ -C 4 alkoxy, C ⁇ -C -haloalkoxy, C ⁇ -C 4 alkylthio, C ⁇ -C4-haloalkylthio, C ⁇ -C 4 alkylsulfonyl, C ⁇ -C4-haloalkylsulfonyl, C ⁇ -C 4 alkoxy carbonyl, C ⁇ -C 4 alkylcarbonyl, C ⁇ -C4 haloalkylcarbonyl, C ⁇ -C 4 alkylcarbonyloxy and C ⁇ -C 4 haloalkylcarbonyloxy tra- gen.
  • the invention also relates to processes for the preparation of substituted tetrazolinonecarboxamides of the formula I, their use as herbicides, herbicidal compositions which contain the substituted tetrazolinonecarboxamides of the formula I as active substances, processes for the preparation of these herbicidal compositions and processes for combating undesired plant growth.
  • Herbicidally active tetrazolinone carboxamides are described, for example, in EP-A-146 279.
  • Cycloalkyl-substituted tetrazolinone carboxamides with herbicidal activity on the amide nitrogen are known, for example, from EP-A-692 482, EP-A-672 663, EP-A-612 735, EP-A-732 326, EP-A-202 929, EP-A -712 850, EP-A-711 761, EP-A-708 097, EP-A-728 750, EP-A-695 748, EP-A-733 625, EP-A-733 624.
  • the object of the present invention was therefore to provide new herbicidally active compounds with which undesired plants can be better controlled. Accordingly, the present substituted tetrazolinone carboxamides of the formula 1 and their herbicidal activity have been found.
  • herbicidal compositions which contain the compounds I and have a very good herbicidal action.
  • processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.
  • the compounds of the formula I can contain one or more centers of chirality and are then present as mixtures of enantiomers or diastereomers.
  • the invention relates both to the pure enantiomers or diastereomers and to their mixtures.
  • the organic molecule parts mentioned for the substituents Het, R 1 , R 2 or as residues on cycloalkyl, phenyl or heterocyclyl rings represent collective terms for individual lists of the individual group members. All carbon chains, that is to say all alkyl, haloalkyl, alkoxy, haloalkoxy -, alkylthio, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, cyanoalkyl, phenylalkyl, heterocyclylalkyl, alkylcarbonyl, haloalkylcarbonyl, alkylcarbonyloxy, haloalkylcarbonyloxy, alkoxycarbonyl, alkenyl, haloalkenyl, alkanoalkenyl, cyanoalkenyl Groups can be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms.
  • Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine or chlorine.
  • -C 1 -C 4 alkyl for: CH 3 , C 2 H 5 , n-propyl, CH (CH 3 ) 2 , n-butyl,
  • Ci-Cg-alkyl for: -C-C 4 alkyl as mentioned above, or for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1st , 1-Dimethylpropyl, 1, 2-Dimethylpropyl, 1-Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1, 1-Dimethylbutyl, 1,2-Dirnethylbutyl, 1, 3-Dimethylbutyl, 2, 2 -Dimethylbutyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2, 2-trimethylpropyl, 1-ethyl-1-methylpropyl and l -Eth
  • C ⁇ -C 4 haloalkyl for: a -CC 4 alkyl radical as mentioned above, which is partially or completely by fluorine, chlorine,
  • Bromine and / or iodine is substituted, e.g. CH 2 C1, CH (C1) 2 , C (C1) 3 , CH 2 F, CHF 2 , CF 3 , CHFCl, CF (C1) 2 , CF 2 C1, CF 2 Br, 1-fluoroethyl, 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, 1,2-dichloroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2, 3-d
  • Ci-Ce-haloalkyl for: Ci-C ⁇ - alkyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, that is to say, for example, one of the aforementioned C 1 -C 4 -haloalkyl radicals, or 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodo-pentyl, 5, 5, 5-trichloro-pentyl, undecafluoropentyl, 6-fluorohexyl, 6-chloro-hexyl, 6-bromohexyl, 6-iodo-hexyl, 6, 6, 6-trichloro-hexyl or dodecafluoro-hexyl; in particular for fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;
  • C 3 -C 8 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl; especially for cyclopentyl or cyclohexyl;
  • C 5 -C 8 cycloalkenyl for: cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3-enyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohept-1 -enyl, cyclohept-2-enyl, cyclohept-3-enyl, cyclohept-4-enyl, cyclooct-1-enyl, cyclooct-2-enyl, cyclooct-3-enyl or cyclooct-4-enyl; in particular for cyclopen- 1-enyl or cyclohex-1-enyl; C 1 -C 4 alkoxy and the alkoxy radicals of alkoxycarbonylalkoxy for: OCH 3 , OC 2 H 5 , n-propoxy, OCH (CH 3 ) 2 , n-but
  • -C-C 4 haloalkoxy -C-C 4 alkoxy as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 0CH 2 C1, 0CH (C1) 2 , 0C (C1) 3 , OCH 2 F, OCHF 2 , OCF 3 , 0CHFC1, 0CF (C1) 2 , 0CF 2 C1, OCF 2 Br, 1-fluoroethoxy, 2-fluoroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2- Di-fluoroethoxy, 2, 2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 1, 2-dichloroethoxy, 2, 2, 2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy
  • -CC alkylthio for: SCH 3 , SC 2 H 5 , n-propylthio, SCH (CH 3 ) 2 , n-butylthio, 1-methylpropylthio, 2-methylpropylthio or SC (CH 3 ); especially for SCH 3 or SC 2 H 5 ;
  • C 1 -C 4 alkylsulfonyl for: S0 2 CH 3 , S0 2 C 2 H 5 , n-propylsulfonyl, S0 2 CH (CH 3 ) 2 , n-butylsulfonyl, 1-methylpropylsulfonyl,
  • C ⁇ -C4-haloalkylsulfonyl a C ⁇ -C 4 alkylsulfonyl as mentioned above, the, chlorine, bromine and / or iodine is partially or fully substituted by fluorine, eg chloromethylsulfonyl, Dichlormethylsulfonyl, trichloromethyl sulfonyl, fluoromethylsulfonyl, difluoromethylsulfonyl, Trifluoromethylsulfonyl, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2, 2-difluoroethylsulfon
  • Phenyl-C ⁇ -C 4 alkyl for: benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-l-yl, 1-phenylbut-l- yl, 2-phenylbut-l-yl, 3-phenylbut-l-yl, 4-phenylbut-l-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1- (phenylmethyl) -eth-l-yl, 1- (phenylmethyl) -1- (methyl) -eth-l-yl or 1- (phenylmethyl ) -prop-1-yl; especially for benzyl or 2-phenylethyl;
  • C 3 -C 8 cycloalkyl -CC 4 -alkyl for: cyclopropylmethyl, 1-cyclopropyl-ethyl, 2-cyclopropyl-ethyl, 1-cyclopropyl-prop-l-yl, 2-cyclopropyl-prop-l- yl, 3-cyclopropyl-prop-l-yl, 1-cyclopropyl-but-1-yl, 2-cyclopropyl-but-l-yl, 3-cyclopropyl-but-l-yl, 4-cyclopropyl-but- l-yl, l-cyclopropyl-but-2-yl, 2-cyclopropyl-but-2-yl, 3-cyclopropyl-but-2-yl, 3-cyclopropyl-but-2-yl, 4-cyclopropyl- but-2-yl, 1- (cyclopropylmethyl) eth-l-yl, 1- (cyclopropylmethyl) -1- (CH 3
  • C 5 -C 8 cycloalkenyl-C 1 -C 4 alkyl for: (cyclopent-1-enyl) methyl, (cyclopent-2-enyl) methyl, (cyclopent-3-enyl) methyl, l- (cyclopent -1-enyl) ethyl, 1- (cyclopent-2-enyl) ethyl, 1- (cyclopent-3-enyl) ethyl, 2- (cyclopent-1-enyl) ethyl, 2- (cyclopent-2 -enyl) ethyl, 2- (cyclopent-3-enyl) ethyl, l- (cyclopent-l-enyl) prop-l-yl, 1- (cyclopent-2-enyl) prop-1-yl, 1- (Cyclopent-3-enyl) prop-1-yl, 2- (Cyclopent-1-enyl) prop-1-yl, 2- (Cyclopent-2
  • Heterocyclyl -CC 4 -alkyl for: heterocyclylmethyl, 1- (heterocyclic) ethyl, 2- (heterocyclyl) ethyl, 1- (heterocyclyl) prop-1-yl, 2- (heterocyclyl) prop-1-yl, 3- (heterocyclyl) prop-1-yl, 1- (heterocyclyl) but-l-yl, 2- (heterocyclyl) but-l-yl, 3- (heterocyclyl) but-l-yl, 4- (heterocyclyl) but -l-yl, 1- (heterocyclyl) but-2-yl, 2- (heterocyclyl) but-2-yl, 3- (heterocyclyl) but-2-yl, 3- (heterocyclyl) but-2-yl, 3- (heterocyclyl) but-2-yl, 3- (heterocyclyl) but-2-yl, 3- (
  • C 1 -C 4 -alkoxy-C 4 -alkyl for: C 1 -C 4 -alkoxy as mentioned above substituted C 1 -C 4 -alkyl, for example for CH 2 OCH 3 , CH 2 OC 2 H 5 , n-propoxymethyl , (1-methylethoxy) methyl, n-butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, (1, 1-dimethylethoxy) methyl, 2- (methoxy) ethyl,
  • Ci-C ⁇ 4 haloalkoxy-C ⁇ -C 4 alkyl by C ⁇ -C 4 -haloalkoxy as mentioned above substituted C ⁇ -C4 alkyl, eg of 2 - (difluoromethoxy) ethyl, 2- (trifluoromethoxy) ethyl or 2 - (pentafluoroethoxy) ethyl; C 1 -C 4 -Alkylthio -CC 4 -alkyl for: C 1 -C 4 -alkylthio as mentioned above substituted C 1 -C 4 -alkyl, that is, for. B.
  • C ⁇ -C 4 -Halogenalkylthio -C ⁇ -C 4 -alkyl for: C ⁇ -C 4 -Halogen- alkylthio substituted as C ⁇ -C 4 alkyl as mentioned above, for example for 2 - (difluoromethylthio) ethyl, 2 - (trifluoromethyl) - thio) ethyl or 2- (pentafluoroethylthio) ethyl;
  • C 1 -C 4 alkylsulfonyl C 1 -C 4 alkyl for: C 1 -C 4 alkylsulfonyl as mentioned above substituted C 1 -C 4 alkyl, for example for CH 2 S0 2 CH 3 , CH 2 S0 2 C 2 H 5 , n-propylsulfonylmethyl, (1-methylethylsulfonyl) methyl, n-butylsulfonylmethyl, (1-methylpropylsulfonyl) methyl, (2-methylpropylsulfonyl) methyl, (1,1-dimethylethylsulfonyl) methyl, 2-methylsulfonylethyl, 2 -Ethylsulfonylethyl, 2- (n-propylsulfonyl) ethyl, 2- (1-methylethylsulfonyl) ethyl, 2- (n-butyl
  • - (-C-C 4 alkyl) carbonyl for: COCH 3 , COC 2 Hs, n-propylcarbonyl,
  • COCH (CH 3 ) 2 n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or COC (CH 3 ) 3 ; in particular for COCH 3 , COC H 5 or COC (CH 3 ) 3 ;
  • (C ⁇ -C 4 -haloalkyl) carbonyl (-C-C 4 alkyl) carbonyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example C0CH 2 C1, C0CH (C1) 2 , C0C (C1) 3 , C0CH 2 F, COCHF 2 , COCF3 COCHFC1, C0CF (C1) 2 , COCFCl, COCF 2 Br, 1-fluoroethylcarbonyl, 2-fluoroethylcarbonyl, 2, 2-difluoroethylcarbonyl, 2, 2, 2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2, 2-difluoroethyl - carbonyl, 2, 2-dichloro-2-fluoroethylcarbonyl, 1, 2-dichloroethyl - carbonyl,
  • - C ⁇ -C 4 -alkylcarbonyloxy for: O-COCH 3 , O-COC 2 H 5 , n-propyl - carbonyloxy, O-COCH (CH 3 ) 2 , n-butylcarbonyloxy, 1-methylpropyl - carbonyloxy, 2-methylpropylcarbonyloxy or 0-COC (CH 3 ) 3 , in particular for O-COCH 3 , O-COC 2 H 5 or 0-COC (CH 3 ) 3 ;
  • - (-C-C 4 haloalkyl) carbonyloxy for: (-C-C 4 alkyl) carbonyloxy as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for 0-COCH 2 Cl , O-COCH (Cl) 2 , 0-COC (Cl) 3 , 0-COCH 2 F, 0-COCHF 2 , O-COCF 3 , O-COCHFCl, 0-COCF (Cl) 2 , 0-COCF 2 Cl , 0-COCF 2 Br, 1-fluoroethylcarbonyloxy, 2-fluoroethylcarbonyloxy, 2,2-di-fluoroethylcarbonyloxy, 2,2, 2-trifluoroethylcarbonyloxy, 2-chloro-2-fluoroethylcarbonyloxy, 2-chloro-2, 2-difluoroethylcarbonyloxy , 2, 2-
  • C 3 -Cg haloalkenyl for: C 3 -Cg alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for 2-chloroallyl, 3-chloroallyl, 2, 3-dichlorallyl, 3, 3-dichlorallyl, 2,3,3-trichlorallyl, 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; in particular for 2-chloro-allyl, 3-chloroallyl or 3, 3-dichloroallyl; C 2 -C 6 haloalkenyl for: C 3 -C 6 haloalkenyl as mentioned above and 2 -Cl -ethenyl;
  • Cyano-C 3 -C 6 -alkenyl for: eg 2-cyanoallyl, 3-cyanoallyl, 4-cyanobut-2-enyl, 4-cyanobut-3-enyl or 5-cyanopent-4-enyl; especially for 3-cyanoallyl or 4-cyanobut-2-enyl;
  • alkynyl and the alkynyl radicals of alkynyloxy for: prop-1-in-1-yl, propargyl, n-but-1-in-1-yl, n-but-1-in-3-yl, n-but-l-in-4-yl, n-but-2-in-l-yl, n-pent-1-in-l-yl, n-pent-l-in-3-yl, n- Pent-l-in-4-yl, n-pent-1-in-5-yl, n-pent-2-in-l-yl, n-pent-2-in-4-yl, n-pent 2-in-5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n-hex-1-in- 1-yl, n- Hex-l-in-3-yl, n-hex-l-in-4-yl,
  • 3- to 7-membered heterocyclyl is understood to mean both saturated, partially or completely unsaturated and aromatic heterocycles having one to three heteroatoms, selected from a group consisting of one to three nitrogen atoms, one or two oxygen atoms and one or two sulfur atoms .
  • saturated heterocycles which can contain a carbonyl or thiocarbonyl ring member are:
  • unsaturated heterocycles which can contain a carbonyl or thiocarbonyl ring member are: dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl, 1,3-oxazoline 2-yl;
  • the 5- and 6-membered ones are preferred, e.g. Furyl such as 2-furyl and 3-furyl, thienyl such as 2-thienyl and 3-thienyl, pyrrolyl such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl such as 2-oxazolyl, 4-oxazolyl and 5-0xazolyl, thiazolyl such as 2-thiazolyl, 4-thiazolyl and 5- Thiazolyl, imidazolyl such as 2-imidazolyl and 4-imidazolyl, oxadiazolyl such as 1, 2, 4-0x
  • R 1 C ⁇ -C 6 -alkyl, C 6 haloalkyl, cyano-Ci ⁇ alkyl,
  • cycloalkyl rings, cycloalkenyl rings, phenyl rings or heterocyclyl rings can each be unsubstituted or carry one to four substituents, each selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 4 -alkoxy, -C-C 4 -haloalkoxy, -C-C 4 -alkylthio, C !
  • C ⁇ -C 6 alkyl particularly preferably C ⁇ -C 6 alkyl, Ci-Cg-haloalkyl, cya no-C ⁇ -C4 ⁇ alkyl, C 3 -C 6 alkenyl, C 3 -CG-haloalkenyl,
  • cycloalkyl rings, cycloalkenyl rings, phenyl rings or heterocyclyl rings are each unsubstituted or one to four substituents, each selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 4 -C 4 halogen alkyl, C 1 -C 4 4 -alkoxy, -CC 4 ⁇ haloalkoxy, -CC 4 -alkylthio, 4-halo can alkylsulfonyl or C ⁇ -C 4 alkylcarbonyl wear C ⁇ -C4-haloalkylthio, C ⁇ -C 4 alkylsulfonyl, C ⁇ -C;
  • cycloalkyl rings, cycloalkenyl rings, phenyl rings or heterocyclyl rings are each unsubstituted or one to four substituents, each selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C ⁇ -C 4 -haloalkyl, C ⁇ -C 4 -Alkoxy, -C-C 4 -haloalkoxy, -C-C 4 -alkylthio, -C-C 4 -haloalkylthio, C ⁇ -C 4 -alkylsulfonyl, C ⁇ -C 4 -halo-alkylsulfonyl or C ⁇ -C 4 -alkylcarbonyl can wear;
  • Ci A ß- alkyl, -C-C 6 haloalkyl, C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, phenyl or C 3 -C 7 membered heterocyclyl, which is a carbonyl or thiocarbonyl Ring link can contain
  • cycloalkyl rings, cycloalkenyl rings, phenyl rings or heterocyclyl rings are each unsubstituted or one to four substituents, each selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C ⁇ -C 4 -alkoxy, -C-C 4 ⁇ haloalkoxy, C ⁇ -C 4 -alkylthio, C ⁇ -C 4 -haloalkylthio, C ⁇ -C 4 -alkylsulfonyl, C ⁇ -C 4 -halo-alkylsulfonyl or C ⁇ ⁇ C 4 alkylcarbonyl can wear;
  • phenyl which is unsubstituted or carries one to four substituents, each selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 6 -haloalkyl, Cx ⁇ -alkoxy, C 1 -C 4 -Halogenalkoxy, -C-C 4 alkylthio, -C-C 4 -Halogenalkyl hio, -C-C -Alkylsulfonyl, C ⁇ -C 4 -Halogenalkylsulfonyl or C ⁇ -C 4 alkylcarbonyl; in particular the substituents X n listed in detail in Table 1;
  • heterocyclic tetrazolinone carboxamides are particularly preferred:
  • substituted tetrazolinecarboxamides of the formula I are very particularly preferred, in which the variables have the following meaning:
  • R 2 -C 6 alkyl in particular C -C alkyl
  • M + in formula IV stands for a cation derived from the base, for example triethylammonium, tetraethylammonium, Na + , K + or Ca 2+ / 2.
  • the bases for both processes A) and B) are amines, such as triethylamine, pyridine and 4-dimethylaminopyridine, tetraalkyl or tetraarylammonium hydroxides, such as tetraethylammonium hydroxide, alkali metal carbonates, hydrogen carbonates and hydrides, such as sodium carbonate, sodium hydrogen carbonate or sodium hydride, alkali metal or Alkaline earth metal hydroxides, such as sodium, potassium or calcium hydroxide.
  • amines such as triethylamine, pyridine and 4-dimethylaminopyridine
  • tetraalkyl or tetraarylammonium hydroxides such as tetraethylammonium hydroxide
  • alkali metal carbonates such as sodium carbonate, sodium hydrogen carbonate or sodium hydride
  • alkali metal or Alkaline earth metal hydroxides such as sodium, potassium or calcium hydroxide.
  • the salts of the formula IV can be obtained, which can be easily isolated, for example, as triethylammonium, tetraethylammonium, sodium, potassium or calcium salts.
  • the tetrazolinones of the formula . II are known per se and can be obtained, for example, by reacting the corresponding aliphatic or aromatic isocyanates with azido-trimethylsilane or with aluminum azide prepared in situ. (Houben-Weyl, Vol E8d, pages 692-693, Thieme-Verlag Stuttgart 1994).
  • the carbamoyl chlorides of the formula III can be prepared, for example, by phosgenation of the corresponding amines of the formula V.
  • Phosgene, diphosgene or triphosgene are suitable as phosgenating agents for this.
  • the phosgenation can alternatively be carried out in the presence or in the absence of a base, for example one of the bases mentioned above. It is also possible to convert the amine of the formula V before the phosgenation by reaction with an acid into the corresponding acid addition salt, for example with hydrogen chloride in the hydrochlorides.
  • Examples of suitable processes for the preparation of the amines of the formula V are the reductive amination of heterocyclic ketones of the formula VII with amines of the formula VIII, or alternatively the reductive amination of heterocyclic amines of the formula IX with aldehydes or ketones of the formula X.
  • This reaction is well known per se (e.g. BAF Abdel-Magid, KG Carson, BD Harris, CA Maryanoff, RD Shah, J. Org. Chem. 61 (1996) 3849 and the literature cited therein).
  • R a , R b R and R b together with the CH group to which they are attached form the radical R 2 , which as far as possible as in
  • the amines of the formula V can also be prepared by acylation of amines of the formula IX and subsequent reduction of the amides XI formed as an intermediate. Both reactions are known per se. (See, for example, Houben-Weyl, Methods of Organic Chemistry, Georg Thieme Verlag, Vol. E5, Stuttgart 1985, p. 972 ff., P. 977 ff. And Vol. XI / 1, Stuttgart 1957, p. 574 ff .)
  • amines of the formula v, with Het optionally substituted furan-3-yl or thiophene-3-yl, can be reacted with amines by reacting compounds of the formula XII, which in turn can be present as tautomers Xlla or Xllb or mixtures thereof R 2 -NH 2 , if desired, in the presence of a catalyst, for example acids, such as hydrochloric acid or sulfuric acid or Lewis acids, such as boron trifluoride, zinc chloride or titanium tetrachloride, are prepared,
  • R d halogen, -CC 6 alkyl or Ci -C 6 haloalkyl
  • the reactions to the substituted tetrazolinonecarboxamides of the formula I according to the invention and the intermediates of the formulas II to XII required for this are generally carried out in an inert organic solvent, for example in aliphatic or aromatic hydrocarbons such as hexane, cyclohexane and toluene, halogenated hydrocarbons such as dichloro - Methane or 1, 2-dichloroethane, ethers such as diethyl ether, tetrahydrofuran or dioxane, or aprotic solvents such as dimethylformamide, dimethyl sulfoxide and acetonitrile or also mixtures of the solvents mentioned.
  • an inert organic solvent for example in aliphatic or aromatic hydrocarbons such as hexane, cyclohexane and toluene, halogenated hydrocarbons such as dichloro - Methane or 1, 2-dichloroethane, ethers
  • the reaction temperature of all the reactions mentioned is between the melting and boiling point of the reaction mixture, preferably (unless stated otherwise) between 0 and 100 ° C. To achieve high conversions, it may be advantageous to carry out the reaction at the boiling point of the reaction mixture.
  • the reactants are generally used in equimolar amounts. To achieve a higher yield, however, it can also make sense to use one or more reactants in excess up to about ten times the molar amount.
  • the above reactions are conveniently carried out at atmospheric pressure or carried out under the autogenous pressure of the respective reaction mixture.
  • the substituted tetrazolinone carboxylic acid amides I can normally be prepared by one of the synthesis processes mentioned above. For economic or procedural reasons, however, it may be more expedient to prepare some compounds I from similar tetrazolinonecarboxamides, but which differ in particular in the meaning of the radical R 1 or R 2 , in a manner known per se, for example by alkylation, condensation reaction, Oxidation, olefination, reduction, etherification, esterification or Wittig reaction.
  • the starting compounds specified for the individual processes are either known or are obtainable in a manner known per se or in analogy to one of the processes described.
  • reaction mixtures are generally worked up by methods known per se, for example by diluting the reaction solution with water and then isolating the product by means of filtration, crystallization or solvent extraction, or by removing the solvent, distributing the residue in a mixture of water and a suitable organic solvent and working up the organic phase towards the product.
  • the substituted tetrazolinonecarboxamides I can be obtained in the preparation as isomer mixtures which, if desired, can, however, be separated into the largely pure isomers by the customary methods such as crystallization or chromatography, including on an optically active adsorbate. Pure optically active isomers can advantageously be prepared from corresponding optically active starting products.
  • the compounds I are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
  • the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants. The following crops are considered, for example:
  • Manihot esculenta Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communreis, Ribes sylvest , Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (see vulgar), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
  • the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not struck wherever possible, while the active ingredients are applied to the leaves below them unwanted plants or the uncovered floor area (post-directed, lay-by).
  • the compounds I or the herbicidal compositions comprising them can be sprayed or atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring.
  • directly sprayable aqueous solutions, powders, suspensions including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring.
  • the application forms depend on the uses; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives,
  • Aqueous use forms can be made from emulsion concentrates,
  • Suspensions, pastes, wettable powders or water-dispersible granules can be prepared by adding water.
  • the compounds I as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols as well as of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylpheny
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules, for example coated, impregnated and homogeneous granules can be placed on solid carriers forth ⁇ by binding the active ingredients.
  • Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or other
  • the concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
  • the formulations generally contain 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • the compounds according to the invention can be formulated, for example, as follows:
  • the substituted tetrazolinone carboxamides can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • the application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.) depending on the control target, the season, the target plants and the growth stage.
  • n-Propyl (tetrahydro-2H-pyran-4-yl) amine bp 90 ° C (12 mm).
  • n-Propyl (tetrahydrothiophen-3-yl) amine b.p. 104-108 ° C (12 mm).
  • the active ingredients suspended or emulsified in water were applied directly after sowing by means of finely defending ⁇ nozzles.
  • the containers were irrigated gently to promote germination and growth and subsequently covered with into account by ⁇ plastic covers until the plants grown were 0. This cover causes the test plants to germinate evenly, unless this was affected by the active ingredients.
  • test plants For the purpose of post-emergence treatment, the test plants 15, depending on the growth habit, were first grown to a height of 3 to 15 cm and then treated with the active ingredients suspended or emulsified in water. The test plants were either sown directly and grown in the same containers, or the tightened WUR ⁇ separated first as seedlings and transplanted some days before 20 of the treatment to the pots.
  • the application rate for post-emergence treatment 1.0 kg / ha ai (active sub ⁇ substance).
  • the plants were kept at temperatures of 10 to 25 25 ° C or 20 to 35 ° C, depending on the species.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP98941362A 1997-08-06 1998-07-20 Substituierte herbizide tetrazolinoncarbonsäureamide Withdrawn EP1003741A1 (de)

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DE19733989 1997-08-06
DE19733989 1997-08-06
PCT/EP1998/004480 WO1999007702A1 (de) 1997-08-06 1998-07-20 Substituierte herbizide tetrazolinoncarbonsäureamide

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US6513908B2 (en) * 1997-07-15 2003-02-04 Silverbrook Research Pty Ltd Pusher actuation in a printhead chip for an inkjet printhead
GB0230045D0 (en) 2002-12-23 2003-01-29 Glaxo Group Ltd Compounds
JP4923698B2 (ja) * 2006-04-24 2012-04-25 宇部興産株式会社 ４−アミノテトラヒドロピラン化合物の製法
EP3159331A1 (en) 2010-05-05 2017-04-26 Infinity Pharmaceuticals, Inc. Tetrazolones as inhibitors of fatty acid synthase
US9822085B2 (en) 2014-03-20 2017-11-21 Sumitomo Chemical Company, Limited Method for producing tetrazolinone compound

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US4666502A (en) * 1982-02-09 1987-05-19 Sandoz Ltd. Herbicidal N-thienyl-chloroacetamides
US4826529A (en) 1983-12-09 1989-05-02 Uniroyal Chemical Company, Inc. Substituted tetrazolinones and herbicidal compositions thereof
US4618365A (en) * 1983-12-09 1986-10-21 Uniroyal Chemical Company, Inc. Substituted tetrazolinones and their use as herbicides
JP2822143B2 (ja) 1993-02-25 1998-11-11 日本バイエルアグロケム株式会社 テトラゾリノン類の水田用除草剤としての利用
JP3390499B2 (ja) * 1993-09-30 2003-03-24 バイエルクロップサイエンス株式会社 テトラゾリノン類の製造方法
JP3571751B2 (ja) 1994-03-18 2004-09-29 バイエルクロップサイエンス株式会社 テトラゾリノン類の水田用除草剤としての利用
JP3694051B2 (ja) 1994-07-12 2005-09-14 バイエルクロップサイエンス株式会社 １−ピリジルテトラゾリノン誘導体および除草剤
JPH0899975A (ja) 1994-08-05 1996-04-16 Nippon Bayeragrochem Kk ５員複素環置換テトラゾリノン誘導体および除草剤
EP0708097A1 (en) * 1994-10-18 1996-04-24 Nihon Bayer Agrochem K.K. Herbicidally active tetrazolinones
JPH08134046A (ja) 1994-11-11 1996-05-28 Nippon Bayeragrochem Kk テトラゾリノン誘導体および除草剤
JPH08193074A (ja) 1994-11-18 1996-07-30 Nippon Bayeragrochem Kk 除草性１−シクロプロピルテトラゾリノン類
JPH08225547A (ja) 1995-02-22 1996-09-03 Nippon Bayeragrochem Kk 除草性 １−シクロアルケニルテトラゾリノン類
EP0732326A1 (en) 1995-03-13 1996-09-18 Nihon Bayer Agrochem K.K. Herbicidally active tetrazolinones
JPH08259547A (ja) 1995-03-20 1996-10-08 Nippon Bayeragrochem Kk 除草性１−アルケニルテトラゾリノン類
JPH08259548A (ja) 1995-03-23 1996-10-08 Nippon Bayeragrochem Kk テトラゾリノン類及び除草剤
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CA2299502A1 (en) 1999-02-18
AR016805A1 (es) 2001-08-01

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