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  • C07C59/40—Unsaturated compounds
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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
  • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
  • C07D253/06—1,2,4-Triazines
  • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
  • C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D253/075—Two hetero atoms, in positions 3 and 5
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
  • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
  • C07C59/40—Unsaturated compounds
  • C07C59/76—Unsaturated compounds containing keto groups
  • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
  • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
  • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
  • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
  • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
  • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
  • C07D253/06—1,2,4-Triazines
  • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
  • C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
  • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
  • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
  • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
  • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
  • C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
  • C07D277/62—Benzothiazoles
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  • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
  • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
  • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
  • C07D279/16—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

• the present invention relates to new substituted 6-aryl-3-thioxo-5- (thi) oxo-2, 3, 4, 5-tetrahydro-l, 2, 4-triazines of the formula I.
• R l C ⁇ -Cg-alkyl, Ci-Cg-haloalkyl or phenyl, which if desired can carry one to three substituents, each selected from the group consisting of nitro, halogen, -C-C 6 alkyl, Ci-Cg-haloalkyl and Ci-Cg-alkoxy;
• R 2 amino, C ⁇ -Cg-alkyl, Ci-Cg-haloalkyl, C 2 -Cg-alkenyl, C 3 -Cg-alkynyl, (Ci-Cg-alkoxy) carbonyl-C ⁇ -Cg-alkyl, C ⁇ -C 6 - Alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl or C 3 -Cg-cycloalkyl;
• Ar is a substituted aryl radical of the formula Ar 1 to Ar 4 :
• R3 is hydrogen or halogen; R 4 cyano, halogen, -CS-NH 2 , hydroxy, C _.- C 6 alkoxy,
• Ci-Cg-haloalkoxy C 2 -C -alkenoxy, C 2 -C 4 -alkynyloxy, (-C-C 4 -alkoxy) carbonyl -C-C 4 -alkoxy or benzyloxy, which are unsubstituted or one to three substituents on the phenyl ring can wear, each selected from the group consisting of halogen, Ci-Cg-alkyl, Ci-Cg-alkoxy and Ci-Cg-haloalkoxy;
• N-OR 15 together with R 4 is a chain 0-CH 2 -CH 2 -0, which is a cyano-, halogen-, Ci-Cg-alkyl-, oxo-, hydroxycarbonyl- or (Ci-Cg-alkoxy) carbonyl- Can carry substituents;
• R 6 is hydrogen, hydroxy, Ci-Cg-alkyl, Ci-Cg-alkoxy, (-C-C 6 -alkoxy) carbonyl -CC-Cg-alkyl, Ci-Cg-alkoxy- (Ci-Cg-alkoxy) carbonyl -Ci-Cg-alkyl, (Ci-Cg-alkoxy) carbonyl-C ⁇ -Cg-alkoxy, C 3 -Cg-alkenyl, C 3 -Cg-alkynyl, C3-Cg-alkenyloxy or C 3 -Cg-alkynyloxy ;
• R 7 is hydrogen, Ci-Cg-alkyl or (Ci-Cg-alkoxy) carbonyl;
• R 8 is hydrogen, hydroxy, mercapto, halogen, Ci-Cg-alkyl, -C-Cg-alkoxy-C ⁇ -Cg-alkyl, hydroxycarbonyl, hydroxycarbonyl-Ci-Cg-alkyl, (Ci-Cg-alkoxy) carbonyl-Ci -Cg-alkyl, (Ci-Cg-alkoxy) carbonyl, Ci-Cg-alkoxy, C ⁇ ⁇ Cg-alkoxy-Ci-Cg-alkoxy, C 3 -Cg-alkenyloxy, C 3 -Cg-alkynyloxy, (Ci-Cg -Alkoxy) carbonyl-Ci-Cg-alkoxy, Ci-Cg-alkylthio, (Ci-Cg-alkoxy) carbonyl-Ci-Cg-alkylthio, C 3 -Cg-alkenylthio, C 3 -C 6 -
• n zero or 1;
• R 9 water tof f, Ci-Cg-alkyl or (Ci-Cg-alkoxy) carbonyl-
• R11 R12 independently of one another at position 4 or 5 of the dioxolane ring are hydrogen, Ci-Cg-alkyl, hydroxycarbonyl or (Ci-Cg-alkoxy) carbonyl;
• R 13 is hydrogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy-Ci-Cg-alkyl, cyano-C ⁇ ⁇ Cg-alkyl, C 3 -C 7 cycloalkyl, 3-oxetanyl, C 3 -Cg alkenyl, C 3 -Cg haloalkenyl or C 3 -Cg alkynyl;
• R15 is hydrogen or Ci-Cg-alkyl
• R 15 is hydrogen, Ci-Cg-alkyl, C 3 -C 7 cycloalkyl, (Ci-Cg-alkoxy) carbonyl-Ci-Cg-alkyl, Ci-Cg-alkylsulfonyl or together with R 15 a tetramethylene or pentarethylene - chain which can be interrupted by an oxygen bridge and / or substituted by a (Ci-Cg-alkoxy) carbonyl group;
• R 17 is hydrogen, halogen or Ci-Cg-alkyl
• R 20 is hydrogen, Ci-Cg-alkyl or Ci-Cg-alkylsulfonyl
• R 21 , R22 independently of one another Ci-Cg-alkyl, (Ci-Cg-alkoxy) carbonyl-Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -Cg-alkynyl or benzyl;
• R 23 is hydrogen or Ci-Cg-alkyl
• R 4 is hydrogen, Ci-Cg-alkyl, (Ci-Cg-alkoxy) carbonyl-Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 ⁇ Cg-alkynyl or benzyl;
• the invention also relates to the use of these compounds I as herbicides or for the desiccation / defoliation of plants, herbicidal agents and agents for the desiccation / defoliation of plants which contain the compounds I as active substances,
• R a is C ⁇ -C -alkyl, C 4 haloalkyl, C 3 -C alkenyl or C 3 -C 4 alkynyl substituents and Q is o-halophenyl containing 1 or 2 further substituents or certain heterocycles fused can stand.
• JP-A 10/053 508 finally relates to 1,2,4-triazines of the formula X.
• R b is C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 -alkynyl or C ⁇ -C 4 haloalkyl
• R c is hydrogen or R b
• R d are, inter alia, H, Ci-Cg-alkyl or -CH (Ci -C 4 alkyl) -COO (H / -C-C 6 alkyl), which is also attributed to a herbicidal activity there.
• the object of the present invention was therefore to develop new herbicides To provide effective compounds with which undesirable plants can be controlled better than before.
• the task also extends to the provision of new desiccant / defoliant connections.
• the compounds I are also suitable for the desiccation and / or defoliation of parts of plants, for which crop plants such as cotton, potatoes, oilseed rape, sunflower, soybeans or field beans, in particular cotton, are suitable.
• crops plants such as cotton, potatoes, oilseed rape, sunflower, soybeans or field beans, in particular cotton
• agents for the desiccation and / or defoliation of plants, methods for producing these agents and methods for the desiccation and / or defoliation of plants with 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.
• E / Z isomers may also be possible.
• the invention relates both to the pure enantiomers or slide ereomers and to their mixtures.
• the substituted 6-aryl-3-thioxo-5- (thi) oxo-2, 3, 4, 5-tetra-hydro-1,2, 4-triazines can be in the form of their agriculturally useful salts, depending on the type of the salt usually does not arrive.
• the salts of I with such bases and those acid addition salts into which the herbicidal action is not adversely affected in comparison with the free compound I are suitable.
• Particularly suitable as basic salts are those of the alkali metals, preferably the sodium and potassium salts, those of the alkaline earth metals, preferably calcium and magnesium salts, those of the transition metals, preferably zinc and iron salts, and ammonium salts in which the ammonium ion is present if desired can carry up to four C 1 -C 4 alkyl, hydroxy C 1 -C 4 alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium and trimethyl (2nd -hydroxyethyl) -ammonium- Salts, furthermore phosphonium salts, sulfonium salts such as preferably tri- (C 1 -C 4 -alkyl) sulfonium salts, and sulfoxonium salts such as preferably tri- (C 1 -C
• Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C 1 -C 4 -alkanoic acids, preferably formate, acetate, propionate and butyrate.
• the organic molecule parts mentioned in the definition of R 1 , R 2 and R 4 to R 24 represent collective terms for individual lists of the individual group members.
• All carbon chains that is to say all alkyl, haloalkyl, alkoxy, haloalkoxy, Alkylthio, alkylsulfonyl, cyanoalkyl, hydroxycarbonylalkyl, alkoxycarbonyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenyl hi and alkynylthio parts 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.
• Ci-Cg-alkyl for: CH 3 , C 2 H 5 , n-propyl, CH (CH 3 ) 2 , n-butyl, CH (CH 3 ) -C 2 H 5 , CH 2 -CH (CH 3 ) 2 , C (CH 3 ) 3 , 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, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3- Wench hylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1,2-
• Ci-Cg-haloalkyl for: Ci-Cg-alkyl 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 C1, CH (C1) 2 , C (C1) 3 , CHFC1, 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, CF 5 ,
• C 3 -C 7 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, in particular for cyclopentyl or cyclohexyl;
• Hydroxycarbonyl-Ci-Cg-alkyl for: eg CH 2 -COOH, 2-hydroxycarbonyl-eth-1-yl, 2-hydroxycarbonyl-prop-1-yl, 3-hydroxycarbonyl-prop-1-yl, l -Hydroxycarbonyl-prop-2-yl, 2-hydroxycarbonyl-but-1-yl, 3-hydroxycarbonyl-but-l-yl, 4-hydroxycarbonyl-but-l-yl, l-hydroxycarbonyl-but-2-yl , 1-Hydroxycarbonyl-but-3-yl, 2-Hydroxycarbonyl-but-3-yl, l-Hydroxycarbonyl-2-methyl-prop-3-yl, 2-Hydroxycarbonyl-2-methyl-prop-3-yl or 2 - (Hydroxycarbonylmethyl) prop-2-yl, especially for 2-hydroxycarbonyl-ethyl;
• Cyano-Ci-Cg-alkyl for: e.g. CH 2 CN, 1-cyanoeth-l-yl, 2-cyano-eth-l-yl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3- Cyano-prop-1-yl, l-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4- Cyanobut-l-yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, l-cyanobut-3-yl, 2-cyano-but-3-yl, l-cyano-2-methyl-prop- 3-yl, 2-cyano-2-methyl-prop-3-yl, 3-cyano-2-methyl-prop-3-yl or 2-cyanomethyl-prop-2-yl, especially for CH 2 CN or 2- Cyanoethyl;
• Ci-Cg-alkoxy for: -C-C 4 alkoxy as mentioned above, and for example n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbu oxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2, 2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2, 2-dimethylbutoxy, 2, 3-dirnethylb toxy, 3, 3-dirnethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1,2, 2-trimethylpropoxy, 1-ethyl-l-methylpropoxy and l -Ethyl-2-methylpropoxy, especially for OCH 3 , 0C 2 Hs or OCH (CH 3 ) 2 ; Ci-Cg-hal
• (Ci-Cg-alkoxy) carbonyl for: e.g. CO-OCH 3 , CO-OC 2 Hs, CO-OCH 2 -C 2 H 5 , CO-OCH (CH 3 ) 2 , n-butoxycarbonyl, CO-OCH (CH 3 ) -C 2 H 5 , CO-OCH 2 -CH (CH 3 ) 2 , CO-OC (CH 3 ) 3 , n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2 , 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1, 1-dimethylbutoxycarbonyl , 1, 2-d
• (C ⁇ -Cg-alkoxy) carbonyloxy for: O-CO-OCH 3 , 0-CO-OC 2 H 5 , n-propoxycarbonyloxy, 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy, 1-methylpropoxycarbonyloxy, 2-methylpropoxycarbonyloxy, 1, 1-dimethylethoxycarbonyloxy, n-pentoxycarbonyloxy, 1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy, 3-methylbutoxycarbonyloxy, 2,2-dimethylpropoxycarbonyloxy,
• (Ci-Cg-alkoxy) carbonylthio for: methoxycarbonylthio, ethoxycarbonylthio, n-propoxycarbonylthio, 1-methylethoxycarbonylthio, n-butoxycarbonylthio, 1-methylpropoxycarbonylthio,
• 2-methylpropoxycarbonylthio 1, 1-dimethylethoxycarbonylthio, n-pentoxycarbonylthio, 1-methylbutoxycarbonylthio, 2-methylbutoxycarbonylthio, 3-methylbutoxycarbonylthio, 2, 2-dimethylpropoxycarbonylthio, 1-ethylpropoxycarbonylthio, n-hexoxycarbonyl -Dimethylpropoxycarbonylthio, 1, 2-dimethyl-propoxycarbonylthio, 1-methylpentoxycarbonylthio, 2-methyl-pentoxycarbonylthio, 3-methylpentoxycarbonylthio, 4-methyl-pentoxycarbonylthio, 1, 1-dimethylbutoxycarbonylthio, 1,2-dimethylbutoxycarbonylthio, 1,2-dimethylbutoxycarbonylthio Dimethylbutoxycarbonylthio, 2, 2-dimethylbutoxycarbonylthio, 2, 3-dimethylbutoxycarbonylthio, 3, 3-dimethylbutoxy
• Ci-Cg-alkylthio for: SCH 3 , SC 2 H 5 , SCH 2 -C 2 H 5 , SCH (CH 3 ) 2 , n-butylthio, SCH (CH 3 ) -C 2 H 5 , SCH 2 -CH ( CH 3 ) 2 , 1, l-dimethylethylthio, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio,
• Ci-Cg-alkoxy carbonyl-Ci-Cg-alkyl for: Ci-Cg-alkyl substituted by (C ⁇ ⁇ Cg-alkoxy) carbonyl as mentioned above, for example for methoxycarbonylmethyl, ethoxycarbonylmethyl, 1 - (methoxycarbonyl) ethyl, 2 - (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl, 3 - (methoxycarbonyl) ropyl, 4- (methoxycarbonyl) butyl, 5- (methoxycarbonyl) pentyl or 6- (methoxycarbonyl) hexyl; Ci-Cg-alkylthio-Ci-Cg-alkyl for: Ci-Cg-alkylthio substituted by Ci-Cg-alkylthio as mentioned above, for example for CH 2 -SCH 3 , CH 2 -SC 2 H 5 , n
• Ci-Cg-alkoxy- (Ci-Cg-alkoxy) carbonyl-Ci-Cg-alkyl for: substituted by Ci-Cg-alkoxy as mentioned above (C ⁇ ⁇ Cg-alkoxy) carbonyl-C ⁇ -Cg-alkyl, so for example for CH 2 -COOCH 2 -OCH 3 , CH 2 -COOCH 2 -OC 2 H 5 , CH 2 -COOCH 2 -OCH (CH 3 ) 2 or CH 2 -COOCH 2 -OC (CH 3 ) 3 ;
• C 2 -Cg alkenyl for: ethenyl or one of the radicals mentioned under C 3 -Cg alkenyl, in particular for ethenyl or prop-2-en-1-yl;
• 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-chloro-allyl, 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-tribromo-allyl or 2, 3-dibromobut-2-enyl, in particular for 2-chloro-allyl, 3-chloroallyl or 3, 3-dichloroallyl;
• C 3 -C 6 alkenyloxy for: for example prop-1-en-l-yloxy, prop-2-en-l-yl-oxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2- yloxy, n-butene-3-yloxy, 1-methyl-prop-l-en-l-yloxy, 2-methyl-prop-1-en-l-yloxy, l-methyl-prop-2-en-l- yloxy, 2-methyl-prop-2-en-l-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, 1- Methyl-but-l-en-l-yloxy, 2-methyl-but-l-en-l-yloxy, 3-methyl-but-l-en-l-yloxy, l-methyl-but-2- en-l-yloxy, 2-methyl-
• C 2 -C 4 alkenyloxy for: ethenyloxy, prop-1-en-l-yloxy, prop-2-en-l-yloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2 -yloxy, n-buten-3-yloxy, 1-methyl-prop-1-en-1-yloxy, 2-methyl-prop-1-en-1-yloxy, 1-methyl-prop-2-en-1 -yloxy or 2-methyl-prop-2-en-1-yloxy, especially for prop-2-en-1-yloxy;
• C 3 -C 6 alkenylthio for: for example prop-1-en-1-ylthio, prop-2-en-1-ylthio, 1-methylethenylthio, n-buten-1-ylthio, n-buten-2- ylthio, n-butene-3-ylthio, 1-methyl-prop-l-en-l-ylthio, 2-methyl-prop-l-en-l-ylthio, l-methyl-prop-2-en-l- ylthio, 2-methyl-prop-2-en-l-ylthio, n-penten-1-ylthio, n-pentene-2-ylthio, n-penten-3-ylthio, n-penten-4-ylthio, 1-methyl-but-l-en-1-ylthio, 2-methyl-but-l-en-l-ylthio, 3-methyl-but-l-en-l-ylthio, l-methyl-but-2
• 1-en-l-ylthio 1, 2-dimethyl-prop-2-en-l-ylthio, 1-ethyl-prop-l-en-2-ylthio, l-ethyl-prop-2-en-l- ylthio, n-hex-l-en-1-ylthio, n-hex-2-en-l-ylthio, n-hex-3-en-l-ylthio, n-hex-4-en-1-ylthio, n-hex-5-en-l-ylthio, 1-methyl-pent-l-en-l-ylthio, 2-methyl-pent-l-en-l-ylthio, 3-methyl-pent-l-en- l-ylthio, 4-methyl-pent-l-en-l-ylthio, l-methyl-pent-2-en-l-ylthio, 2-methyl-pent-2-en-l-ylthio, 3-methyl pent-2-
• C 3 ⁇ Cg alkynyl for: e.g. B. Prop-1-in-l-yl, propargyl, n-but-1-in-l-yl, n-but-l-in-3-yl, n-but-l-in-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 l-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
• C 3 ⁇ Cg-alkynyloxy for: for example prop-1-in-l-yloxy, prop-2-in-l-yl-oxy, n-but-1-in-l-yloxy, n-but-l-in -3-yloxy, n-but-l-in-4-yloxy, n-but-2-in-l-yloxy, n-pent-1-in-l-yloxy, n-pent-l-in -3-yloxy, n-pent-1-in-4-yloxy, n-pent-1-in-5-yl-oxy, n-pent-2-in-1-yloxy, n-pent-2-in -4-yloxy, n-pent-2-yn-5-yloxy, 3-methyl-but-l-yn-3-yloxy, 3-methyl-but-l-yn-4-yloxy, n-hex-1 -in-l-yloxy, n-hex-l
• C 2 -C 4 alkynyloxy for: ethynyloxy, prop-1-in-1-yloxy or prop-2-in-1-yloxy, in particular for Pr ⁇ p-2-in-1-yloxy;
• C 3 ⁇ Cg-alkynylthio for: prop-1-in-l-ylthio, prop-2-in-l-ylthio, n-but-1-in-l-ylthio, n-but-l-in-3- ylthio, n-but-l-in-4-ylthio, n-but-2-in-l-ylthio, n-pent-1-in-l-ylthio, n-pent-l-in-3-ylthio, n-pent-l-in-4-ylthio, n-pent-l-in-5-ylthio, n-pent-2-in-l-ylthio, n-pent-2-in-4-ylthio, n- Pent-2-in-5-ylthio, 3-methyl-but-l-in-3-ylthio, 3-methylbut-l-in-4-ylthio, n-Hex-1-in-l-ylthi
• Ci-Cg alkylene for: e.g. Methylene, 1,1-ethylene, 1,2-ethylene, 1, 3-propylene, 2, 2-propylene, 1,4-butylene, 1,5-pentylene or 1,6-hexylene, especially for methylene, 1, 1-ethylene or 2,2-propylene.
• R 1 Ci-Cg-alkyl, especially methyl
• R 2 amino or Ci-Cg-alkyl, especially amino or methyl
• R 3 halogen, especially fluorine or chlorine
• R 4 halogen, especially chlorine
• R 6 is hydrogen, hydroxy, Ci-Cg-alkyl, Ci-Cg-alkoxy, C 3 -Cg -alkenyl or C 3 -Cg-alkynyl, in particular C 3 ⁇ Cg-alkynyl;
• R 7 is hydrogen
• R 8 is hydrogen, Ci-Cg-alkyl or (Ci-Cg-alkoxy) carbonyl-Ci-Cg-alkyl; n 1;
• R 14 is methylene or 1,1-ethylene
• substituted 6-aryl-3-thioxo-5-oxo-2, 3, 4, 5-tetrahydro-l, 2, 4-triazines of the formulas lu to ly are very particularly preferred, in particular
• R 25 represents hydrogen or Ci-Cg-alkyl.
• an inert solvent / diluent e.g. in acetic acid, a lower alcohol such as methanol, ethanol, n-propanol and isopropanol, an ether such as tert. -Butyl methyl ether, tetrahydrofuran, dioxane and 1, 2-diethoxyethane, an aprotic solvent such as dimethyl formamide, dimethyl sulfoxide and pyridine.
• aprotic solvent such as dimethyl formamide, dimethyl sulfoxide and pyridine.
• tert. -Butyl methyl ethers are also suitable as mixtures of the solvents / diluents mentioned with water.
• the reaction is generally carried out at 20 ° C. to the boiling point of the respective reaction mixture.
• the condensation of IV with V is generally catalyzed by acids, in particular carboxylic acids such as formic acid and acetic acid, sulfonic acids such as benzenesulfonic acid and p-toluenesulfonic acid or mineral acids such as hydrochloric acid, sulfuric acid and phosphoric acid.
• acids in particular carboxylic acids such as formic acid and acetic acid, sulfonic acids such as benzenesulfonic acid and p-toluenesulfonic acid or mineral acids such as hydrochloric acid, sulfuric acid and phosphoric acid.
• the ring closure reaction from IV to I is usually catalyzed by bases.
• bases Suitable for this are e.g. Alkali metal carbonates such as sodium carbonate, alkali metal hydrogen carbonates such as sodium hydrogen carbonate and alkali metal hydroxides such as sodium hydroxide, but also nitrogen bases such as triethylamine, dicyclohexylethylamine, pyridine and 4-dimethylaminopyridine.
• arylglyoxylic acids and their alkyl esters (V) are known or can be prepared in a manner known per se (see, for example, JS Nimitz & HS Mosher, J. Org. Chem. 46. (1981), 211-213; WMP Johnson & G. Holan, Aust. J. Chem. 34 (1981), 2363 and X. Creary, J. Org. Chem. J52. (1987), 5026).
• L stands for chloride, bromide, iodide or 0-S0 2 -OR 1 .
• Suitable solvents / diluents are especially aprotic solvents such as N, N-dimethylformamide, dimethyl sulfoxide, acetonitrile, acetone, tetrahydrofuran, dioxane and 1,2-diethoxyethane.
• the Reaktios unit is carried out at 0 ° C to boiling ⁇ temperature of the reaction mixture.
• thiosemicarbazides and thiocarboxylhydrazides IV and IX are known, but can also be prepared in a manner known per se (see, for example, KA Jensen et al., Acta Che ica Scandinavica 22 (1968), 1 and C.-J. Krö- ger et al., Liebigs Ann. Chem. 643 (1961), 121).
• the sulfurization is usually carried out in an inert solvent / diluent, for example in an aromatic hydrocarbon such as toluene and the xylenes or in an organic amine such as pyridine.
• the reaction temperature is usually from 20 ° C to the boiling point of the reaction mixture.
• the substituted 6-aryl-3-thioxo-5- (thi) oxo-2, 3, 4, 5-tetrahydro-1,2,4-triazines I can normally be prepared by one of the synthesis processes mentioned above. For economic or procedural reasons, however, it may be more convenient to use some compounds I from similar 6-aryl-3-thioxo-5- (thi) oxo-2, 3, 4, 5-tetrahydro-l, 2, 4-triazines differ, however, in particular in the meaning of one of the residues on Ar, to be produced, in a manner known per se, for example through nitration, sulfonation, chlorosulfonation, halogenation, alkylation, acylation, acetal hydrolysis, acetalization, amidation, ester hydrolysis, condensation reaction, oxidation, Peterson olefination, reduction, etherification, esterification, Wittig reaction or Meerwein 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 one organic solvents and working up the organic phase towards the product.
• the substituted 6-aryl-3-thioxo-5- (thi) oxo-2, 3, 4, 5-tetra-hydro-1, 2, 4-triazines I can be obtained in the preparation as isomer mixtures, which, however, if desired, according to the usual methods such as crystallization or chromatography, also on an optically active adsorbate, into which largely pure isomers can be separated. Leave pure optically active isomers can advantageously be produced from corresponding optically active starting products.
• Salts of the compounds I which can be used commercially can be formed by reaction with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride, or by reaction with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
• a base of the corresponding cation preferably an alkali metal hydroxide or hydride
• an acid of the corresponding anion preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
• Salts of I can also be prepared in a conventional manner by salting the corresponding alkali metal salt, as can ammonium, phosphonium, sulfonium and sulfoxonium salts using ammonia, phosphonium, sulfonium or sulfoxonium hydroxides.
• the compounds I and their agriculturally useful salts 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:
• the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
• the compounds I or the compositions comprising them can be sprayed, atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, sprays or granules. Dusting, scattering or pouring can be used.
• the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
• inert auxiliaries mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils as well as 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 as well as oils of vegetable or animal origin
• aliphatic, cyclic and aromatic hydrocarbons e.g. Paraffins, tetrahydronaphthalene, alkylated n
• Aqueous use forms can be made from emulsion concentrates,
• Suspensions, pastes, wettable powders or water-dispersible granules can be prepared by adding water.
• the substrates as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
• wetting agents adhesives, dispersants or emulsifiers.
• concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
• the surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols as well as fatty alcohol glycol ether, 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, tributylphen
• Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
• Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
• 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.
• the concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
• the formulations contain from about 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).
• Dissolved mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and There are 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.
• the active ingredients I or 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 hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
• 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.
• Example 32 6- (3-Chloro-4-hydroxyphenyl) -2, 4-dimethyl-5-oxo-3-thioxo - 2,3,4,5-tetrahydro -1,2,4-triazine Using 2 - (3-chloro-4-hydroxyphenyl) -2-oxoacetic acid, the desired product of value was obtained analogously to Example 12.
• 1,2,4-triazine and 21.9 g (0.51 mol) of lithium chloride in 610 ml of dimethylformamide were heated to the reflux temperature for 7 hours. Then poured onto ice water. After acidification with dilute hydrochloric acid, the solid product of value formed was filtered off, then washed with water and ethyl acetate and finally dried. Yield: 45.5 g; M.p .: 219-221 ° C.
• Plastic flower pots with loamy sand with about 3.0% humus served as culture vessels.
• the seeds of the test plants were sown separately according to species.
• the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
• the tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic covers until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.
• test plants For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
• the application rate for post-emergence treatment was 31.2, 15.6, 7.8 and 3.9 g / ha a.S. (active substance).
• the plants were kept in a species-specific manner at temperatures of 10 to 25 ° C and 20 to 35 ° C.
• the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
• Young, 4-leafed (without cotyledons) cotton plants served as test plants, which were grown under greenhouse conditions (relative humidity 50 to 70%; day / night temperature 27/20 ° C.).
• the young cotton plants were dripping wet ( ', based on the spray addition of 0.15 wt .-% of the fatty alcohol alkoxylate Plurafac LF 700 ® 1 - broth) with aqueous preparations of the active compounds I treated leaf.
• the amount of water applied was the equivalent of 1000 l / ha. After 13 days, the number of leaves dropped and the degree of defoliation in% were determined.
• U is a low-foam, non-ionic surfactant from BASF AG

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