EP2844649A1 - Salze von n-(tetrazol-5-yl)- und n-(triazol-5-yl)arylcarbonsäureamiden und ihre verwendung als herbizide - Google Patents

Salze von n-(tetrazol-5-yl)- und n-(triazol-5-yl)arylcarbonsäureamiden und ihre verwendung als herbizide

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Publication number
EP2844649A1
EP2844649A1 EP13719550.9A EP13719550A EP2844649A1 EP 2844649 A1 EP2844649 A1 EP 2844649A1 EP 13719550 A EP13719550 A EP 13719550A EP 2844649 A1 EP2844649 A1 EP 2844649A1
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EP
European Patent Office
Prior art keywords
alkyl
cycloalkyl
alkoxy
heterocyclyl
radicals
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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EP13719550.9A
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German (de)
English (en)
French (fr)
Inventor
Ralf Braun
Simon DÖRNER-RIEPING
Hartmut Ahrens
Christian Waldraff
Arnim Köhn
Hansjörg Dietrich
Elmar Gatzweiler
Christopher Hugh Rosinger
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Bayer CropScience AG
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Bayer CropScience AG
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Priority to EP16179944.0A priority Critical patent/EP3121172B1/de
Priority to EP13719550.9A priority patent/EP2844649A1/de
Priority to PL16179944T priority patent/PL3121172T3/pl
Publication of EP2844649A1 publication Critical patent/EP2844649A1/de
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/12—Quaternary ammonium compounds
    • 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
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • 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
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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
    • A01N43/80—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 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62—Quaternary ammonium compounds
    • C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and weeds in
  • WO 2012/028579 A1 discloses N- (tetrazol-5-yl) - and N- (triazol-5-yl) benzamides as herbicides.
  • Priority earlier and unpublished applications EP 1 1 176 378 and EP 1 1 187 669 disclose N- (tetrazol-5-yl) and N- (triazol-5-yl) arylcarbonic acid amides as herbicides.
  • these drugs do not always have a sufficient effect against harmful plants and / or they are sometimes not sufficiently compatible with some important crops, such as cereals, corn or rice.
  • the object of the present invention is therefore to provide further herbicidally active substances. This task is described by the following
  • An object of the present invention are thus salts of N- (tetrazol-5-yl) - and N- (triazol-5-yl) arylcarbonklareamiden of formula (I)
  • A is N or CY B is N or CH
  • X is nitro, halogen, cyano, formyl, thiocyanato, (Ci-C6) alkyl, halo (Ci- C6) alkyl, (C2-C6) alkenyl, halo (C2-C6) alkenyl , (C2-C6) alkynyl, halo (C 3 -C 6) - alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C (O) N (R 1 ) 2 , NR 1 C (O) N (R 1 ) 2 , OC (O) N (
  • Y is hydrogen, nitro, halogen, cyano, thiocyanato, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 - C 6) -alkynyl, (C3-C6) -cycloalkyl, (C3-C6) cycloalkenyl, halo (C3-C6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C (O) N (
  • radicals in each case by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy or halogeno (C 1 -C 6) -alkoxy, and wherein
  • Heterocyclyl carries oxo groups, or
  • Z can also be hydrogen, (C 1 -C 6) -alkyl or (C 1 -C 6) -alkoxy, if Y is the radical S (O) n R 2 ,
  • W is hydrogen, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) alkynyl, halo (C2-C6) -alkynyl, (C 3 -C 7) cycloalkyl, (C 3 -C 7) -halocycloalkyl, (Ci-C 6) alkoxy, (Ci-C 6) - Haloalkoxy, S (O) n - (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6) -alkyl, (Ci -C 6 ) alkoxy-
  • R represents (Ci-C 8) alkyl, halo (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, halo (C 2 - C 8) alkenyl, (C2-C8) alkynyl , Halo (C 2 -C 8) -alkynyl, where these six radicals mentioned above are in each case represented by s radicals from the group consisting of hydroxyl, nitro, cyano, SiR 5 3 , PO (OR 5 ) 2 , S (O) n - ( Ci-C 6) -alkyl, S (O) n - (Ci-C 6) -haloalkyl, (Ci-C 6) - alkoxy, halo (Ci-C 6) -alkoxy, N (R 3) 2, COR 3 , COOR 3 , OCOR 3 , NR 3 COR 3 ,
  • each of the seven latter radicals is substituted by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and wherein heterocyclyl n carries oxo groups, or R is in each case by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy and (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl-substituted (C 3 -C 7 ) Cycloalkyl, heteroaryl
  • Q is O, S, or NR 3 ,
  • R 1 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C2-C6) alkenyl, (C 2 - C 6) haloalkenyl, (C2-C6) alkynyl , (C2-C6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O- (C -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) alkyl- heteroaryl , Heterocycl, (Ci-C 6) alkyl-heterocyclyl, (Ci-C 6) al
  • Heterocyclyl where the 21 last-mentioned radicals are in each case represented by s radicals from the group consisting of cyano, halogen, nitro, rhodano, OR 3 , S (O) n R 4 , N (R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 4 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , COSR 4 , CON (R 3 ) 2 and (C 1 -C 4 ) alkoxy- (C 2 -C 6) alkoxycarbonyl substituted and wherein heterocyclic n
  • R 3 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) - Cycloalkyl- (C 1 -C 6 ) -alkyl or phenyl, R 4 is (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl (C 1 -C 6 ) -alkyl or phenyl,
  • R 5 is (C 1 -C 4 ) -alkyl
  • M + represents a cation selected from the group consisting of
  • a saturated or unsaturated / aromatic N-containing heterocyclic ionic compound having 1 -10 C atoms in the ring system, optionally mono- or poly-fused and / or (C 1 -C 4 ) -alkyl, meaning 0, 1 or 2, p is 0, 1, 2, 3 or 4, s is 0, 1, 2 or 3.
  • alkyl radicals having more than two carbon atoms may be straight-chain or branched.
  • Alkyl radicals mean, for example, methyl, Ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1, 3-dimethylbutyl.
  • AI kenyl is, for example, allyl, 1-methylprop-2-en-1-yl,
  • Alkynyl means e.g. Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl.
  • the multiple bond can each be in any position of the unsaturated radical.
  • Cycloalkyl means a carbocyclic saturated ring system having three to six C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • cycloalkenyl is a monocyclic alkenyl group having three to six carbon ring members, e.g. Cyclopropenyl, cyclobutenyl,
  • Cyclopentenyl and cyclohexenyl, wherein the double bond may be in any position.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Heterocyclyl means a saturated, partially saturated or fully unsaturated cyclic radical containing from 3 to 6 ring atoms, of which from 1 to 4 are from the group oxygen, nitrogen and sulfur, and additionally by a
  • heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl,
  • Heteroaryl means an aromatic cyclic radical containing from 3 to 6 ring atoms, of which from 1 to 4 are from the group consisting of oxygen, nitrogen and sulfur, and may additionally be fused by a benzo ring.
  • heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1, 2,3-oxadiazolyl, 1, 2 4-oxadiazolyl, 1, 2,5-oxadiazolyl, 1, 3,4-oxadiazolyl, 1, 2,4-triazolyl, 1, 2,3-triazolyl, 1, 2,5-triazolyl, 1, 3,4- Triazolyl, 1, 2,4-triazolyl, 1, 2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1, 2,3-thiadiazolyl, 1, 2,5-thiadiazolyl, 2H-1,2,3, 4-tetrazolyl,
  • cation M + is understood to mean that the salts of the formula (I) according to the invention are present in charge-neutral form.
  • polyvalent cations for example divalent or trivalent cations, two or three anions are present as counteranions.
  • the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, then enantiomers and
  • stereoisomers can be prepared by using stereoselective reactions using optically active starting materials and / or
  • the invention also relates to all stereoisomers and mixtures thereof which are of the general formula (I), but not specifically defined.
  • the compounds of the invention may also occur as geometric isomers (E / Z isomers) due to the oxime ether structure.
  • the invention also relates to all E / Z isomers and mixtures thereof, which are of the general formula (I), but not specifically defined. Preference is given to compounds of the general formula (I) in which
  • A is N or CY
  • B is N or CH
  • X is nitro, halogen, cyano, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogen- (C 2 -C 6 ) -alkenyl, C 6) alkenyl, (C2-C6) alkynyl, halo (C3-C6) -alkynyl, (C 3 - C 6) cycloalkyl, halo (C3-C6) cycloalkyl, (Ci- C6) alkyl-O- (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, halo (C3-C6) cycloalkyl- (Ci-C 6 ) -alkyl, COR 1 , OR 1
  • Heterocyclyl carries n oxo groups
  • Y is hydrogen, nitro, halogen, cyano, thiocyanato, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6 ) alkynyl, halo (C 3 -C 6 ) alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkenyl, halogeno (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , OR 1 , COOR 1 , CHNOR 1 , CH 2
  • Z represents halogen, cyano, nitro, thiocyanato, halo (Ci-C6) alkyl, (C 2 -C 6) - alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl , Halogeno (C 3 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, halogeno (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, halogeno, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , COOR 1 , C (O) N (R 1 ) 2 , C (O) NR 1 OR 1 , OSO 2 R 2 , S (O) n R
  • Z can also be hydrogen, (C 1 -C 6) -alkyl or (C 1 -C 6) -alkoxy, if Y is the radical S (O) n R 2 , W represents hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (Ci-Ce) alkoxy, (Ci- C 6) haloalkoxy, S (O) n - (Ci- C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl, halogen, nitro or cyano, R means (C 1 -C 4 ) 8) alkyl, halo (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, halo (C 2 - C 8) alkenyl, (
  • heterocyclyl n carries oxo groups, or R is in each case by s radicals from the group consisting of halogen, nitro, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, S (O) n - (Ci-C 6) alkyl (C 1 -C 6) -alkoxy, halogeno (C 1 -C 6) -alkoxy and (C 1 -C 6) -alkoxy- (C 1 -C 4 ) -alkyl-substituted (C 3 -C 7) -cycloalkyl, heteroaryl, heterocyclyl or phenyl,
  • Q is O, S, or NR 3 ,
  • R 1 represents hydrogen, (Ci-C 6) -alkyl, (C2-C6) alkenyl, (C2-C6) -alkynyl, (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) - Alkyl-heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl-heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-
  • radicals in each case by s radicals from the group consisting of cyano, halogen, nitro, OR 3 , S (O) n R 4 , N (R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , CON (R 3 ) 2 and (C 1 -C 4) -alkoxy- (C 2 -C 6 ) -alkoxycarbonyl, and where heterocyclyl carries n oxo groups,
  • R 2 is (C 1 -C 6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 4) -alkyl C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C
  • R 3 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl or (C 3 -C 6 ) - cycloalkyl- (Ci-C 6) alkyl, R 4 is (Ci-C 6) -alkyl, (C 2 -C 6) -alkenyl or (C 2 -C 6) alkynyl,
  • R 5 is methyl or ethyl
  • M + represents a cation selected from the group consisting of
  • ammonium ions whose hydrogen atoms are represented by p radicals from the group consisting of (C 1 -C 4) -alkyl, hydroxy (C 1 -C 4) -alkyl, (C 3 -C 6) -cycloalkyl, (C 1 -C 2 ) - Alkoxy (Ci-C 2 ) -alkyl, hydroxy (Ci-C 2 ) -alkoxy- (Ci-C 2 ) -alkyl, (Ci-C 2 ) -Mercaptoalkyl, phenyl and benzyl are substituted, whereby the before radicals mentioned by n radicals from the group consisting of halogen nitro, cyano, azido, (Ci-C 2) alkyl, (Ci-C 2) - haloalkyl, (C 3 -C) cycloalkyl, (Ci-C 2) Alkoxy, (Ci-C 2 ) -haloalkyl
  • quaternary phosphonium ions such as tetra ((C 1 -C 4 ) -alkyl) phosphonium and tetraphenylphosphonium, where the (C 1 -C 4 ) -alkyl radicals and the phenyl radicals are represented by p radicals from the group consisting of halogen (C 1 -C 2 ) -alkyl, (C 1 -C 2 ) -haloalkyl, (C 3 -C 4 ) -cycloalkyl, (C 1 -C 2 ) -alkoxy and (C 1 -C 2 ) -haloalkoxy being substituted,
  • tertiary sulfonium ions such as Ti - ((C 1 -C 4 ) -alkyl) sulfonium
  • tertiary oxonium ions such as tri - ((Ci-C 4) alkyl) -oxonium, wherein the (Ci-C 4) - alkyl with p radicals from the group consisting of halo (Ci-C 2) - Alkyl, (C1- C 2) -haloalkyl, (C 3 -C) cycloalkyl, (Ci-C2) alkoxy and (Ci-C2) haloalkoxy substituted,
  • ions derived from heterocyclic compounds consisting of the group pyridine, quinoline, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl 2-methylpyridine, piperidine, pyrrolidine, morpholine, thiomorpholine, pyrrole, imidazole, 1, 5-diazabicyclo [4.3.0] non-5-ene (DBN) and 1,8-diazabicyclo [5.4.0] undec-7 en (DBU), n means 0, 1 or 2, p means 0, 1, 2, 3 or 4, s means 0, 1, 2 or 3.
  • A is N or CY
  • B is N or CH
  • X is nitro, halo, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, OR 1, S (O) n R 2 ( C 1 -C 6 -alkyl-S (O) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) Alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , (C 1 -C 6 ) -alkyl Heteroaryl, (C 1 -C 6 ) -alkyl heterocyclyl, where the two last-mentioned radicals are in each
  • Y is hydrogen, nitro, halogen, cyano, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, OR 1, S (O) n R 2, SO 2 N (R 1) 2, N (R 1 ) 2 , CHNOR 1 , CH 2 ONC (R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (Ci-C 6 ) - alkyl-S (O) n R 2 , (Ci-C 6 ) -Alkyl-OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , (C 1 -C 6 ) -al
  • Z can also be hydrogen, methyl, methoxy or ethoxy, if Y is the radical S (O) n R 2 , W is hydrogen, methyl, ethyl, methoxymethyl, methoxy, fluorine, chlorine or S (O) n CH 3 ,
  • R represents (Ci-C 8) alkyl, halo (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, halo (C 2 - C 8) alkenyl, (C2-C8) alkynyl , Halo (C 2 -C 8) -alkynyl, where these six radicals mentioned above are in each case represented by s radicals from the group consisting of cyano, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) - Alkoxy, halo (C 1 -C 6 ) alkoxy, COR 3 , COOR 3 , OCOR 3 , NR 3 COR 3 , NR 3 SO 2 R 4 , (C 3 -C 6 ) cycloalkyl, heteroaryl, heterocyclyl and phenyl wherein the three last-mentioned radicals are each substituted by s radicals from the group consist
  • R is substituted by s radicals selected from the group consisting of halogen, nitro, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl-substituted phenyl, R 1 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl (C 1
  • radicals in each case by s radicals from the group consisting of cyano,
  • R 2 is in each case substituted by s radicals from the group consisting of halogen and OR 3 substituted (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl or (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) - alkyl, R 3 is hydrogen or (C 1 -C 6 ) -alkyl, R 4 is (C 1 -C 6 ) -alkyl
  • M + represents a cation selected from the group consisting of
  • Methylammonium Ion Dimethylammonium Ion, Trimethylammonium Ion,
  • n means 0, 1 or 2
  • n means 0, 1 or 3
  • N- (tetrazol-5-yl) - and N- (triazol-5-yl) benzamides and nicotinamides of the formula (II) can, for example, according to the in WO 2012/028579 A1, EP1 1 176 378 and
  • Reactions can also be synthesized in a parallelized manner, which can be done in a manual, partially automated or fully automated manner. It is possible, for example, the implementation of the reaction, the work-up or the purification of the products or
  • the listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed.
  • This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots.
  • Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
  • the implementation of single or multiple synthetic steps can be supported by the use of polymer-supported reagents / Scavanger resins.
  • the present invention also provides libraries containing at least two compounds of the formula (I).
  • the compounds of the formula (I) according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Also difficult to control perennial harmful plants that expire from rhizomes, rhizomes or other permanent organs are well detected by the active ingredients.
  • the present invention therefore also provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, wherein one or more of the present invention
  • Compound (s) on the plants e.g., weeds such as mono- or dicotyledons
  • the compounds of the invention may be e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence or Nachauflaufmaschine be applied.
  • some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.
  • the compounds according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then stop their growth and finally die after three to four weeks
  • Ipomoea Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Pineapple, Asparagus, Avena,
  • Crops such as agricultural crops or ornamental plantings.
  • the compounds of the present invention (depending on their respective structure and applied application rate) are excellent
  • Influence of phytonutrients and harvest relief e.g. be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, since, for example, storage formation can thereby be reduced or completely prevented.
  • the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special special traits for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
  • Preferred with respect to transgenic crops is the use of the compounds of the invention in economically important transgenic crops of useful and ornamental plants, eg. As cereals such as wheat, barley, rye, oats, millet, rice and corn or even crops of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • the inventive Compounds are used as herbicides in crops that are resistant to the phytotoxic effects of herbicides or
  • the application of the compounds of the invention in economically important transgenic crops of useful and ornamental plants, eg. As cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or even crops of sugar beet, cotton, soybeans, rapeseed, potato, tomato, pea and others
  • the compounds according to the invention can preferably be employed as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • Glufosinate see, for example, EP-A-0242236, EP-A-242246) or glyphosate
  • transgenic crops for example cotton, with the ability
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins (Bt toxins) to produce, which the
  • Transgenic crop plants with modified fatty acid composition (WO 91/13972). genetically modified crops with new content or secondary substances z.
  • nucleic acid molecules can be used in any genetic manipulations.
  • nucleic acid molecules can be used in any genetic manipulations.
  • Plasmids are introduced which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments.
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one
  • Cosuppressions need.es or the expression of at least one appropriately engineered ribozyme that specifically cleaves transcripts of the above gene product.
  • DNA molecules can be used, which cover the entire coding sequence of a gene product including any flanking sequences present, as well as DNA molecules comprising only parts of the coding sequence, which parts must be long enough to cause an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known in the art (see, for example, Braun et al., EMBO J. 1 1 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106). Expression of the nucleic acid molecules can also be found in the
  • Organelles of the plant cells take place.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
  • transgenic plants are available, the altered properties by
  • the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against
  • Herbicides containing essential plant enzymes e.g. As acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydroxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD Hydroxyphenylpyruvat dioxygenases
  • Harmful plants often have effects that are specific for application in the particular transgenic culture, such as altered or specially extended weed spectrum that can be controlled
  • the invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic
  • the compounds according to the invention show a higher solubility in water and thus, for example, more advantageous formulation properties. They are very well suited for the production of water based formulations.
  • the compounds of the invention may be in the form of wettable powders,
  • the invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates,
  • EC emulsifiable concentrates
  • EW emulsions
  • Water-in-oil emulsions sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • SC suspension concentrates
  • CS capsule suspensions
  • DP dusts
  • mordants mordants
  • granules for litter and soil application granules (GR) in the form of micro, spray, elevator and adsorption granules
  • WG water-dispersible granules
  • SG water-soluble granules
  • ULV formulations microcapsules and waxes.
  • the necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are, for example
  • Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agent, dispersing agent) in addition to the active ingredient, apart from a diluent or inert substance.
  • surfactants of the ionic and / or nonionic type wetting agent, dispersing agent
  • Emulsifiable concentrates are made by dissolving the active ingredient in one
  • organic solvents e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • emulsifiers which may be used are: alkylarylsulfonic acid calcium salts, such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as
  • Fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers,
  • Propylene oxide-ethylene oxide condensation products alkyl polyethers, sorbitan esters, e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g.
  • Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. upstairs with the others
  • Emulsions e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as described e.g. listed above for the other formulation types.
  • Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
  • the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • Dust-like formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which
  • Granulation aids, fillers, etc. are used. In the water
  • the content of active ingredient is for example between 1 and 95 wt .-%, preferably between 10 and 80 wt .-%.
  • the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, preserving,
  • Antifreeze and solvents, fillers, carriers and dyes, defoamers, Evaporation inhibitors and pH and viscosity affecting agents are included in the composition.
  • the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dusty preparations, ground or spreading granules and sprayable
  • Solutions are usually no longer diluted with other inert substances before use.
  • the type of herbicide used u.a. varies the required application rate of the compounds of formula (I). It can vary within wide limits, e.g. between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha.
  • the following examples illustrate the invention.
  • a dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuting in a hammer mill.
  • a wettable powder readily dispersible in water is obtained by adding 25 parts by weight of a compound of formula (I) and / or its salts, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight
  • a dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight
  • Mineral oil (boiling range, for example, about 255 to about 277 C) mixed and ground in a ball mill to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a
  • a water-dispersible granule is also obtained by
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
  • test plants Greenhouse grown under good growth conditions.2 to 3 weeks after sowing, the test plants are treated in the single leaf stage.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
  • Echinochloa crus galli Matricaria inodora, Pharitis purpureum, Stellaria media and Veronica persica.

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EP13719550.9A 2012-05-03 2013-04-30 Salze von n-(tetrazol-5-yl)- und n-(triazol-5-yl)arylcarbonsäureamiden und ihre verwendung als herbizide Withdrawn EP2844649A1 (de)

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EP13719550.9A EP2844649A1 (de) 2012-05-03 2013-04-30 Salze von n-(tetrazol-5-yl)- und n-(triazol-5-yl)arylcarbonsäureamiden und ihre verwendung als herbizide
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EP13719550.9A EP2844649A1 (de) 2012-05-03 2013-04-30 Salze von n-(tetrazol-5-yl)- und n-(triazol-5-yl)arylcarbonsäureamiden und ihre verwendung als herbizide

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MX2014013159A (es) 2015-01-19
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HUE042768T2 (hu) 2019-07-29
US20150105253A1 (en) 2015-04-16
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ZA201408836B (en) 2017-09-27
CO7180218A2 (es) 2015-02-09
BR112014027185B1 (pt) 2019-10-22
UA113545C2 (xx) 2017-02-10
CN104271563A (zh) 2015-01-07
BR112014027185A2 (pt) 2017-06-27
US9371315B2 (en) 2016-06-21
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EA025517B1 (ru) 2016-12-30
AU2013255929B2 (en) 2017-02-16
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EA201401205A1 (ru) 2015-04-30
CN104271563B (zh) 2017-10-17
JP6104368B2 (ja) 2017-03-29
WO2013164331A1 (de) 2013-11-07
KR20150003784A (ko) 2015-01-09
AU2013255929A1 (en) 2014-11-20
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