EP2892885A1 - Amides d'acide bicycloarylcarboxylique à action herbicide - Google Patents

Amides d'acide bicycloarylcarboxylique à action herbicide

Info

Publication number
EP2892885A1
EP2892885A1 EP13756174.2A EP13756174A EP2892885A1 EP 2892885 A1 EP2892885 A1 EP 2892885A1 EP 13756174 A EP13756174 A EP 13756174A EP 2892885 A1 EP2892885 A1 EP 2892885A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
cycloalkyl
halo
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.)
Withdrawn
Application number
EP13756174.2A
Other languages
German (de)
English (en)
Inventor
Hartmut Ahrens
Andreas Van Almsick
Ralf Braun
Arnim Köhn
Stefan Lehr
Hansjörg Dietrich
Elmar Gatzweiler
Christopher Hugh Rosinger
Dirk Schmutzler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP13756174.2A priority Critical patent/EP2892885A1/fr
Publication of EP2892885A1 publication Critical patent/EP2892885A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A01N43/82—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 three 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
    • A01N43/64—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
    • 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
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • 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
    • 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
    • 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
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and weeds in
  • EP 1 1158258 discloses N- (tetrazol-5-yl), N- (triazol-5-yl) and N- (1, 2,5-oxadiazol-3-yl) bicycloarylcarboxamides and their use as herbicides. However, these compounds do not always show a sufficient effect against harmful plants and / or they are sometimes not sufficiently compatible with some important ones
  • Crops such as cereals, corn or rice.
  • N- (tetrazol-5-yl), N- (triazol-5-yl), N- (1, 2,5-oxadiazol-3-yl) - and N- (1, 3,4-oxadiazol-2-yl) bicycloarylcarboxylic acid amides substantially different from those known in the art
  • An object of the present invention are thus N- (tetrazol-5-yl) -, N- (triazol-5-yl) -, N- (1, 2,5-oxadiazol-3-yl) - and N- (1 , 3,4-oxadiazol-2-yl) bicycloarylcarboxamides of the formula (I) or salts thereof
  • X is nitro, halo, cyano, rhodano, (d-Ce alkyl, halo (Ci-C6) 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, halo (C 3 -C 6) cycloalkyl, (C 3 -C 6) - cycloalkenyl, halo (C 3 -C 6) - cycloalkenyl, (C 3 -C 6) -cycloalkenyl, (C 3 -C 6) -cycloalkyl- (Ci-C6) alkyl, halo (C 3 -C 6) -cycloalkyl- (Ci-C6) alkyl, (C 3
  • R 2 O (O) C (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl, (R 1 ) 2 N (O) C (R 1 ) N (O) C- (Ci-C 6 ) -alkyl,
  • R 2 (O) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl
  • W is hydrogen, halogen, nitro, cyano, rhodano, (C 1 -C 6 -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) -alkenyl, (C2-C6) alkynyl, halo (C 3 - C 6) -alkynyl, (C 3 -C /) - cycloalkyl, halo (C 3 -C /) - cycloalkyl, (Ci-C 6) - Alkoxy, halogen- (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkyl- (O) n S-, (C 1 -C 6 ) -haloalkyl (O) nS-, (C 1 -C 6) - Alkoxy, hal
  • R is hydrogen, (Ci-C 6) -alkyl, Ha! Ogen (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C2-C6) alkenyl, (C 2 -C 6 ) alkynyl, halo (C 3 -C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl, halo (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) -CycSoalkyl - (Ci-C6) alkyl, halo (C 3 -C 6) - cycloalkyl- (Ci-C 6) alkyl, R 1 (O) C- (Ci-C 6) alkyl, R 1 O (O) C- (Ci-C 6) -alkyl, (R 1) 2 N (O) C- (Ci- C 6) -A!
  • R x is (C 3 -C) -cycloalkyl, heteroaryl, heterocyclyl or phenyl, where the four radicals mentioned above are in each case represented by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogen (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl,
  • R Y is hydrogen, (Ci-C 6) -A! Kyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) -a! Kenyi , (C2-C6) -Alkiny !, halo (C 3 -C 6) -alkynyl, (Cs-C / J-cycloalkyl,
  • Trifluoromethylcarbonyl halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl,
  • R z is hydrogen, (C 1 -C 6 ) -alkyl, R 1 0- (C 1 -C 6 ) -alkyl, R'CH 2 , (C 3 -C 6 ) -cycloalkyl, halogeno (C 1 -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, R 1 0 , R 1 (H) N, methoxycarbonyl, ethoxycarbonyl,
  • Heterocyclyl carries n oxo groups
  • R 1 represents hydrogen, (Ci-C 6) 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, (Cs-CeJ-cycloalkyl, (C 3 -C 6 ) -cycloalkenyl, halo (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, cycloalkyl- (C 1 -C 6 ) -alkyl-O- (Ci C 6 ) alkyl, phenyl, phenyl (C
  • R 2 is (Ci-C 6) -alkyl, Haiogen- (Ci-C 6) alkyl, (C 2 -C 6) -Alkenyi, halo (C 2 -C 6) - alkenyl, (C 2 -C 6) -Aikinyl, halo (C3-C6) -alkynyl, (C 3 -C 6) -Cycloaikyl, (C 3 -C 6) -
  • R 3 represents hydrogen, (Ci-C 6) alkyl, halo (Ci-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 (Ci-Ce) alkyl, halo (Ci-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 hydrogen or (C 1 -C 4 ) -alkyl
  • R 6 is (C 1 -C 4 ) -alkyl
  • R 'de notes acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl,
  • L is a 3-, 4- or 5-membered fused-on, unsaturated bridge whose bridge atoms consist of t carbon atoms and m heteroatoms from the group consisting of O, S and N.
  • alkyl radicals having more than two carbon atoms may be straight-chain or branched.
  • Alkyl radicals mean e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1, 3-dimethylbutyl.
  • alkenyl means e.g. 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 selected from the group consisting of oxygen, nitrogen and sulfur, and which may additionally be annelated by a benzo ring.
  • 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 selected from the group consisting of oxygen, nitrogen and sulfur, and which 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,
  • the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetrically substituted carbon atoms are present, enantiomers and diastereomers may occur. Likewise, stereoisomers occur when sulfoxides are present. Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants. The invention also relates to all stereoisomers and mixtures thereof which are of the general formula (I), but not specifically defined. The compounds of formula (I) can form salts. Salt formation can through
  • Suitable bases are organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates
  • alkylsulfonium and alkylsulfoxonium salts such as (C 1 -C 4) -trialkylsulfonium and (C 1 -C 4) -trialkylsulfoxonium salts.
  • the compounds of formula (I) may be prepared by addition of a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, e.g. Carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulfonic acids, such as p-toluenesulfonic acid, to a basic group, e.g. Amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, e.g. Carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicy
  • R 7 , R 8 , R 12 , R 13 , R 22 and R 23 are each independently
  • R 1 ) 2 N (O) C, R 1 O, (R 1 ) 2 N, R 2 (O) n S, R 1 O (0) 2 S, (R 1 ) 2 N (O) 2 S and R 1 is 0- (C 1 -C 6 ) -alkyl, and wherein heterocyclyl carries n oxo groups, R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 are each independently hydrogen, halogen, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (Ci-C) alkoxy, (Ci C 4) -haloalkoxy or (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl or in each case two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24
  • R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 is an acetal of the formula -O- (C 2 -C 4 ) -alkylene O-,
  • R 1 1, R 18, R 19, R 26 and R 27 are each independently hydrogen, (Ci- C 6) 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, where the six radicals mentioned above are each represented by s radicals from the group consisting of nitro, cyano , R 2 (0) n S, (R 1 ) 2 N , R 1 O, R 1 (0) C, R 1 0 (0) C, R 1 (0) CO, R 2 0 (0) CO, R 1 (0) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N, (C 3 -C 6 ) -cycloalkyl, heteroaryl, heterocyclyl and phenyl, wherein the four last-menti
  • R 28, R 29, R 30 and R 31 are each independently hydrogen, nitro, halogen, cyano, thiocyanato, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6 ) alkenyl,
  • Halogeno (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, halogeno (C 3 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, halogeno (C 3 -) C6) cycloalkyl, (C3-C6) cycloalkenyl, halo (C 3 -C 6) cycloalkenyl, (C 3 - C 6) -cycloalkyl- (Ci-C (6) alkyl, halo C 3 - C6) cycloalkyl- (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkenyl, (Ci-C 6) alkyl, halo (C 3 -C 6) cycloalkenyl (C 6 ) -alkyl, R 1 (O) C, R 1 (R 1 ON ) C,
  • R 2 (O) 2 S (R 1 ) N (O) C- (C 1 -C 6 ) -alkyl
  • Q represents a remainder Q1, Q2, Q3 or Q4,
  • X is nitro, halo, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) - alkenyl, (C 2 -C 6) -alkynyl, (C 3 -C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, halo (C 3 -C 6) cycloalkyl (C 1 -C 6 ) -alkyl, R 1 (O) C,
  • R 1 (R 1 ON ) C, R 1 O (O) C, (R 1 ) 2 N (O) C, RO, (R 1 ) 2 N, R 1 (O) C (R 1 ) N, R 2 (O) 2 S (R 1 ) N,
  • W is hydrogen, halogen, nitro, cyano, (Ci-CeJ-alkyl, halogeno (Ci-Ce) - alkyl, (C 3 -C) -cycloalkyl, (Ci-C 6 ) -alkoxy, (Ci-C 6 ) -Alkyl- (O) n S-, R 1 O (0) C, (R 1 ) 2 N, R 1 (O) C (R 1 ) N or R 2 (O) 2 S (R 1 ) N .
  • R is hydrogen
  • R x represents (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 - C6) alkenyl, (C 2-C6) alkynyl, halo (C3-C6) -alkynyl, where the radicals mentioned above six respectively by s radicals selected from the group consisting (from R 2 0) n S, (R 1) 2 N, R 1 0 , R 1 (0) C, RO (0) C, R 1 (0) CO, R 2 0 (0) CO, R 1 (0) C (R 1) N, R 2 (0) 2 S (R 1 ) N, (C 3 -C 6) -cycloalkyl, heteroaryl, heterocyclyl and phenyl, where the four last-mentioned radicals are represented by s radicals from the group consisting of (C 1 -C 6 -alkyl, halogeno (C 1
  • R Y is hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C /) - cycloalkyl, (Ci-C6) alkoxy, methoxycarbonyl, methoxycarbonylmethyl, halogen, amino .
  • R z is hydrogen, (C 1 -C 6 ) -alkyl, R 1 O- (C 1 -C 6 ) -alkyl, R'CH 2 , (C 3 -C 7 ) -cycloalkyl, halogeno (C 1 -C 6 ) -alkyl, R 1 O, R 1 (H) N, methoxycarbonyl, acetylamino or methylsulfonyl, R 1 represents hydrogen, (Ci-C 6) -A! KyS, halo (Ci-C 6) alkyl, (C3-C 6) -Cyc!
  • R 2 is (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, halo (C 3 - C 6) cycloalkyl, (C3-C6 ) -Cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl,
  • R 3 is hydrogen or (C 1 -C 6 ) -alkyl
  • R 4 is (C 1 -C 6 ) -alkyl
  • R 5 is hydrogen or (C 1 -C 4 ) -alkyl
  • R ' is acetoxy, acetamido, methoxycarbonyl or (C-3-C6) -cycloalkyl, n is 0, 1 or 2, s is 0, 1, 2 or 3,
  • L represents a bridge selected from the group consisting of A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A1, A12, A13, A14, A17, A25, A26, A27, A28, A29 , A30, A31, A32, A33, A34, A35, A36, A37, A38, A41, 49, 50, 51, 53, 55, 57, 59, 61, 62, 72, 13, 14, 14, 14, 14, 144, ⁇ 145, ⁇ 146, ⁇ 147, ⁇ 148, ⁇ 149, ⁇ 150, ⁇ 151, ⁇ 157, ⁇ 58, ⁇ 168, ⁇ 274, ⁇ 275, ⁇ 276, ⁇ 277, ⁇ 278, ⁇ 279, ⁇ 280, ⁇ 281, ⁇ 282, ⁇ 283, ⁇ 284, ⁇ 285, ⁇ 286, ⁇ 287, ⁇ 363 , ⁇ 364, ⁇ 365, ⁇ 366, ⁇ 367, ⁇ 368,
  • R 7 , R 8 , R 12 , R 13 , R 22 and R 23 are each independently
  • R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 are each independently hydrogen, halogen, (C 1 -C 4) -alkyl, (C 1 -C 4) Haloalkyl or (C 1 -C 4) -alkoxy, or two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 form together with the carbon atom, to which they are attached, a carbonyl group or a
  • Oxime of the formula C NOR 1 or in each case two geminaie R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 is an acetal of the formula -0- (C 2 -C4) -alkylene-0-,
  • R 11 , R 18 , R 19 , R 26 and R 27 are each independently hydrogen or (Ci-Cr-alkyl, wherein the (Ci-Ce) alkyl group by s radicals from the group
  • X is nitro, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, chiorofluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, cyclopropyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, Methoxyethoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl,
  • W is hydrogen, chlorine or methyl
  • R is hydrogen
  • R x represents methyl, ethyl, n-propyl, prop-2-en-1-yl, methoxyethyl, ethoxyethyl or methoxyethoxyethyl
  • R Y is methyl, ethyl, n-propyl, chlorine or amino
  • R z is methyl, ethyl, n-propyl or methoxymethyl.
  • L denotes a bridge selected from the group consisting of A1, A2, A4, A5, A6, A7, A8, A25, A26, A28, A29, A30, A31, A32, A49, A50, A51, A53, A55, A57, A59, A61, A139, A140, A141, A142, A143, A145, A146, A147, A148, A149, A150, A274, A275, A278, A279, A280, A281, A282, A283, A284, A285, A286, A363, A364, A365, A366, A367, A368, A369, A370, A371, A372 and A373,
  • R 7 , R 8 , R 12 , R 13 , R 22 and R 23 are each independently
  • R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 are each independently hydrogen, halogen, methyl, methoxy, ethoxy or two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 together with the carbon atom to which they are attached form a carbonyl group or a
  • Oxime of formula C NOR 1 or two geminal R 9 , R 10 , R 14 , R 15 , R 16 , R 17 , R 20 , R 21 , R 24 and R 25 is an acetal of the formula -0- (CH 2 ) 2-0-,
  • R 1 is hydrogen, methyl or ethyl
  • R 11 , R 19 , R 26 and R 27 are each independently hydrogen or methyl
  • R 28 , R 29 , R 30 and R 31 independently of one another are each hydrogen, nitro, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl,
  • Chlorodifluoromethyl dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, Heptafluoroisopropyl, cyclopropyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl.
  • the substituents and symbols unless otherwise defined, have the same meaning as described for formula (I).
  • dehydrating reagents commonly used for amidation reactions such as B. 1, 1 'carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 2,4,6-tripropyl-1, 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc. are used.
  • CDI 1, 1 'carbonyldiimidazole
  • DCC dicyclohexyl carbodiimide
  • T3P 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide
  • alkylating agents such as. B. alkyl halides, sulfonates or dialkyl sulfates can be used in the presence of a base.
  • 5-amino-1H-tetrazoles of the formula (III) are either commercially available or can be prepared analogously to methods known from the literature.
  • substituted 5-aminotetrazoles can be prepared from amino-tetrazole by the method described in Journal of the American Chemical Society (1954), 76, 923-924:
  • X represents a leaving group such as iodine.
  • the 5-amino-1H-triazoles of the formula (III) are either commercially available or can be prepared analogously to methods known from the literature.
  • substituted 5-aminotriazoles can be prepared from aminotriazole according to the method described in Zeitschrift fur Chemie (1990), 30 (12), 436-437:
  • X represents a leaving group such as iodine.
  • Substituted 5-aminotriazoles can also be synthesized, for example, as described in Chemische Berichte (1964), 97 (2), 396-404:
  • Substituted 5-aminotriazoles can also be used, for example, as in Angewandte Chemie
  • the 4-amino-1, 2,5-oxadiazoles of the formula (VI) are either commercially available or known or can be prepared analogously to methods known from the literature.
  • 3-alkyl-4-amino-1,2,5-oxadiazoles can be prepared according to the method described in Russian
  • 3-aryl-4-amino-1, 2,5-oxadiazoles can be synthesized as described in Russian Chemical Bulletin, 54 (4), 1057-1059, (2005) or Indian Journal of Chemistry, Section B:
  • 3-Amino-4-halo-1, 2,5-oxadiazoles can be prepared, for example, from the commercially available 3,4-diamino-1, 2.5 by the method described in Heteroatom Chemistry 15 (3), 199-207 (2004) Oxadiazole be prepared by a Sandmeyer reaction:
  • Nucleophilic radicals R Y can be found in Journal of Chemica! Research, Synopses, (6), 190, 1985 or in or Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, (9), 2086-8, 1986 or in Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya), 53 (3 ), 596-614, 2004, by substitution of the leaving group L in 3-amino-1, 2,5-oxadiazoles.
  • L stands for a leaving group such. Chlorine, bromine, iodine, mesyloxy, tosyloxy, trifluorosulfonyloxy etc.
  • dehydrating reagents commonly used for amidation reactions such as B. 1, 1 'carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 2,4,6-tripropyl-1, 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc. are used.
  • CDI 1, 1 'carbonyldiimidazole
  • DCC dicyclohexyl carbodiimide
  • T3P 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide
  • the compound of formula VIII employed in scheme 8 can be prepared by reacting an acyl isothiocyanate of formula X with a hydrazide of formula IX according to the method described in Synth. Commun. 25 (12), 1885-1892 (1995).
  • dehydrating reagents commonly used for amidation reactions such as B. 1, 1 'carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 2,4,6-tripropyl-1, 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc. are used.
  • CDI 1, 1 'carbonyldiimidazole
  • DCC dicyclohexyl carbodiimide
  • T3P 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide
  • the amines of the formula (XII) are either commercially available or known in the literature or can, for example, by the method described in Scheme 13 by base-catalyzed alkylation or by reductive alkylation or by the method described in Scheme 14 by nucleophilic substitution of a leaving group L such as chlorine Amine R-NH2 can be produced.
  • 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.
  • Synthesis methods allow a number of protocols known from the literature, which in turn can be carried out manually or automatically.
  • the reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
  • the preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries.
  • the present invention also provides libraries containing at least two compounds of formula (I) and their salts.
  • the compounds of the formula (I) according to the invention (and / or their salts), together referred to as "compounds according to the invention", have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants
  • the present invention therefore also relates to a method for controlling undesirable plants or regulating the growth of plants, preferably in plant crops, wherein one or more of the plants according to the invention are plants which are expectorant from rhizomes, rhizomes or other permanent organs
  • Compound (s) on the plants e.g., weeds such as mono- or dicotyledons
  • the compounds according to the invention can be applied, for example, in pre-sowing (optionally also by incorporation into the soil), pre-emergence or postemergence process.
  • 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.
  • 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 cultures Preferred with respect to transgenic cultures is the use of the compounds of the invention in economically important transgenic crops of useful and
  • Ornamental plants z.
  • cereals such as wheat, barley, rye, oats, millet, rice and corn or cultures of sugar beet, cotton, soybeans, rapeseed, potato, tomato, pea and other vegetables.
  • the compounds of the invention can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or
  • the application of the compounds of the invention or their salts in economically important transgenic crops of useful and ornamental plants eg.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • the compounds according to the invention can be used 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 characterized by a combination 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.
  • adapters or linkers can be attached to the fragments be, see, for. Sambrook et al., 1989, Molecular Cioning, A Laboratory Manual, 2nd Ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one
  • Cosuppressions canes or the expression of at least one appropriately engineered ribozyme that specifically cleaves transcripts of the above gene product.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. 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 synthase (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthase
  • HPPD hydroxyphenylpyruvate 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 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, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and 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 spreading and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG),
  • WP wettable powder
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW emulsions
  • SC suspension concentrates
  • 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, in addition to the active substance, also contain ionic and / or nonionic surfactants (wetting agents, dispersants) other than a diluent or inert substance, for example polyoxyethylated alkylphenols.
  • the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are made by dissolving the active ingredient in one
  • organic solvents e.g. Butanol, cyclohexanone, 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 can be used are: alkylarylsulfonic acid calcium salts such as calcium 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 such as e.g. Sorbitan fatty acid esters or
  • Polyoxethylenesorbitanester such. Polyoxyethylene. 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.
  • 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.
  • EW Oil-in-water emulsions
  • Granules can either be adsorbed by atomizing the active ingredient, granulated inert material or by applying active substance concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carriers such as sand, Kaoiinite or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • adhesives for example polyvinyl alcohol, sodium polyacrylate or mineral oils
  • 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. at
  • the active substance concentration can be about 1 to 90,
  • 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 .-% 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,
  • 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
  • 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.
  • Step 1 Synthesis of 7-methyl-1-benzothiophene-6-carboxylic acid methyl ester
  • Step 3 Synthesis of 7-methyl-N- (1-methyl-1H-tetrazol-5-yl) -1-benzothiophene-6-carboxamide
  • n-Pr n-propyl
  • c-Pr c-propyl
  • Ph phenyl
  • Table 2 Compounds of the invention of the general formula (I) wherein Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A30, wherein the radicals R 7 and R 8 are both hydrogen
  • Table 1 1 Compounds of the invention of the general formula (I), wherein Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A32, wherein the radicals R 7 and R 8 are both hydrogen
  • R x is an ethyl group and R is hydrogen and L is the bridge A8, wherein the radical R 7 is hydrogen
  • R Y is a methyl group and R is hydrogen and L is the bridge A8, wherein the radical R 7 is hydrogen
  • R z represent a methyl group and R is hydrogen and L is the bridge A8, where R 7 is hydrogen
  • Table 20 Compounds of the invention of the general formula (I) wherein Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A363, wherein the radicals R 28 , R 29 , R 30 and R 31 is
  • Table 25 Compounds according to the invention of the general formula (I) in which Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A364 in which R 29 , R 30 and R 31 are hydrogen
  • Table 26 Compounds according to the invention of the general formula (I) in which Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A364 in which the radicals R 29 , R 30 and R 31 are hydrogen
  • Table 29 Compounds according to the invention of the general formula (I) in which Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A364, where R 29 , R 30 and R 31 are hydrogen
  • Table 31 Compounds of the invention of the general formula (I) wherein Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A365, wherein the radicals R 28 , R 30 and R 31 are hydrogen
  • Table 32 Compounds of the invention of the general formula (I) in which Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A365, in which the radicals R 28 , R 30 and R 31 are hydrogen
  • Table 33 Compounds of the invention of the general formula (I) in which Q is Q1, R x is an n-propyl group and R is hydrogen and L is the bridge A365 in which the radicals R 28 , R 30 and R 31 are hydrogen
  • Bridge A365 means where R 28 , R 30 and R 31 are hydrogen
  • Table 35 Compounds of the invention of the general formula (I) in which Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A365 in which the radicals R 28 , R 30 and R 31 are hydrogen
  • Table 37 Compounds of the invention of the general formula (I) in which Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A366, in which R 28 , R 29 and R 31 are hydrogen
  • Table 38 Compounds according to the invention of the general formula (I) in which Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A366 in which the radicals R 28 , R 29 and R 31 are hydrogen
  • Table 40 Compounds of the invention of the general formula (I) wherein Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A366 in which R 28 , R 29 and R 31 are hydrogen
  • Table 43 Compounds of the invention of the general formula (I) in which Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A367, in which R 28 , R 29 and R 30 are hydrogen
  • Table 44 Compounds of the invention of the general formula (I) in which Q is Q1, R x is an ethyl group and R is hydrogen and L is the bridge A367, in which the radicals R 28 , R 29 and R 30 are hydrogen
  • Table 46 Compounds of the invention of the general formula (I) in which Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A367, in which R 28 , R 29 and R 30 are hydrogen
  • Table 55 Compounds of the invention of the general formula (I) in the form of the sodium salts, wherein Q is Q1, R * is a methyl group and L is the bridge A366, wherein the radicals R 28 , R 29 and R 31 are hydrogen
  • Table 57 Compounds of the invention of the general formula (I) in which Q is Q1 and R is hydrogen and L is the bridge A6, in which the radicals R 7 and R 8 are hydrogen
  • Y is a methyl group and R is hydrogen and L is the
  • Table 61 Compounds of the invention of the general formula (I) wherein Q is Q1, R x is a methyl group and R is hydrogen and L is the bridge A282, wherein the radicals R 12 , R 13 , R 14 and R 15 is
  • Table 62 Compounds of the general formula (I) according to the invention wherein Q is Q1, R x is an ethyl group, and R is hydrogen and L the bridge A282 means, in which the radicals R 12, R 13, R 14 and R 15 are hydrogen
  • Table 63 Compounds of the invention of the general formula (I) in which Q is Q1, R x is an n-propyl group and R is hydrogen and L is the bridge A282 in which the radicals R 12 , R 13 , R 14 and R 15
  • Q is Q1
  • R x is an n-propyl group and R is hydrogen
  • L is the bridge A282 in which the radicals R 12 , R 13 , R 14 and R 15
  • Table 64 Compounds of the invention of the general formula (I) wherein Q is Q 2, R x is a methyl group and R is hydrogen and L is the bridge A282, wherein the radicals R 12 , R 13 , R 14 and R 15 are
  • Table 65 Compounds of the invention of the general formula (I) wherein Q is Q3, R Y is a methyl group and R is hydrogen and L is the bridge A282 in which the radicals R 12 , R 13 , R 14 and R 15 are
  • Table 68 Compounds of the general formula (I) according to the invention wherein Q is Q1, R x is an ethyl group, and R is hydrogen and L the bridge A286 means, in which the radicals R 12, R 13, R 14 and R 15 are hydrogen

Abstract

L'invention concerne des amides d'acide bicycloarylcarboxylique de formule générale (I), utilisés comme herbicides. (I), Dans cette formule (I), X et W représentent des radicaux tels que hydrogène, des radicaux organiques tels que alkyle et d'autres radicaux tels que halogène. Q représente triazolyle, tétrazolyle ou oxadiazolyle.
EP13756174.2A 2012-09-05 2013-09-03 Amides d'acide bicycloarylcarboxylique à action herbicide Withdrawn EP2892885A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP13756174.2A EP2892885A1 (fr) 2012-09-05 2013-09-03 Amides d'acide bicycloarylcarboxylique à action herbicide

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP12183128 2012-09-05
EP13756174.2A EP2892885A1 (fr) 2012-09-05 2013-09-03 Amides d'acide bicycloarylcarboxylique à action herbicide
PCT/EP2013/068173 WO2014037342A1 (fr) 2012-09-05 2013-09-03 Amides d'acide bicycloarylcarboxylique à action herbicide

Publications (1)

Publication Number Publication Date
EP2892885A1 true EP2892885A1 (fr) 2015-07-15

Family

ID=47044765

Family Applications (1)

Application Number Title Priority Date Filing Date
EP13756174.2A Withdrawn EP2892885A1 (fr) 2012-09-05 2013-09-03 Amides d'acide bicycloarylcarboxylique à action herbicide

Country Status (6)

Country Link
US (1) US20150216171A1 (fr)
EP (1) EP2892885A1 (fr)
JP (1) JP2015528459A (fr)
CN (1) CN104768937B (fr)
BR (1) BR112015004648A2 (fr)
WO (1) WO2014037342A1 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3006444B1 (fr) 2013-05-31 2017-09-27 Nissan Chemical Industries, Ltd. Composé amide hétérocyclique
AR101230A1 (es) * 2014-07-28 2016-11-30 Bayer Cropscience Ag Amidas del ácido arilcarboxílico bicíclicas y su uso como herbicidas
GB201416111D0 (en) 2014-09-12 2014-10-29 Syngenta Participations Ag Improvements in or relating to organic compounds
TW201636329A (zh) 2015-02-02 2016-10-16 佛瑪治療公司 作為ｈｄａｃ抑制劑之雙環［４，６，０］異羥肟酸
US10112915B2 (en) 2015-02-02 2018-10-30 Forma Therapeutics, Inc. 3-aryl bicyclic [4,5,0] hydroxamic acids as HDAC inhibitors
GB201510254D0 (en) 2015-06-12 2015-07-29 Syngenta Participations Ag Improvements in or relating to organic compounds
BR112018000088B1 (pt) * 2015-07-03 2022-07-12 Bayer Cropscience Aktiengesellschaft Derivados de n-(1,3,4-oxadiazol-2-il)aril carboxamida com ação herbicida, seu uso, composição herbicida, e método para controle de plantas indesejadas
AU2016330250A1 (en) * 2015-09-28 2018-03-29 Bayer Cropscience Aktiengesellschaft Acylated N-(1,2,5-oxadiazole-3-yl)-, N-(1,3,4-oxadiazole-2-yl)-, n-(tetrazole-5-yl)- and N-(triazole-5-yl)-aryl carboxamides, and use thereof as herbicides
US10555935B2 (en) 2016-06-17 2020-02-11 Forma Therapeutics, Inc. 2-spiro-5- and 6-hydroxamic acid indanes as HDAC inhibitors
CN110392680A (zh) 2016-12-22 2019-10-29 拜耳作物科学股份公司 取代的唑基吡咯酮和唑基乙内酰脲及其盐及其作为除草活性物质的用途
CN110128346A (zh) * 2019-05-17 2019-08-16 南开大学 一类联芳酰胺吡唑衍生物及其制备方法和用途
CN116602296B (zh) * 2023-07-20 2023-09-15 成武县晨晖环保科技有限公司 一种包含炔苯酰草胺的除草组合物

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60500438A (ja) 1983-01-17 1985-04-04 モンサント　カンパニ− 植物細胞を形質転換するためのプラスミド
BR8404834A (pt) 1983-09-26 1985-08-13 Agrigenetics Res Ass Metodo para modificar geneticamente uma celula vegetal
BR8600161A (pt) 1985-01-18 1986-09-23 Plant Genetic Systems Nv Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio
EP0221044B1 (fr) 1985-10-25 1992-09-02 Monsanto Company Vecteurs de plantes
EP0242236B2 (fr) 1986-03-11 1996-08-21 Plant Genetic Systems N.V. Cellules végétales résistantes aux inhibiteurs de la synthétase de glutamine, produites par génie génétique
US5013659A (en) 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
IL83348A (en) 1986-08-26 1995-12-08 Du Pont Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
DE69133261D1 (de) 1990-03-16 2003-06-26 Calgene Llc Davis Dnas, die für pflanzliche desaturasen kodieren und deren anwendungen
JP3325022B2 (ja) 1990-06-18 2002-09-17 モンサント カンパニー 植物中の増加された澱粉含量
EP0536330B1 (fr) 1990-06-25 2002-02-27 Monsanto Technology LLC Plantes tolerant le glyphosate
SE467358B (sv) 1990-12-21 1992-07-06 Amylogene Hb Genteknisk foeraendring av potatis foer bildning av staerkelse av amylopektintyp
DE4104782B4 (de) 1991-02-13 2006-05-11 Bayer Cropscience Gmbh Neue Plasmide, enthaltend DNA-Sequenzen, die Veränderungen der Karbohydratkonzentration und Karbohydratzusammensetzung in Pflanzen hervorrufen, sowie Pflanzen und Pflanzenzellen enthaltend dieses Plasmide
DE19532312A1 (de) * 1995-09-01 1997-03-06 Basf Ag Pyrazol-4-yl-benzoylderivate
DE19638484A1 (de) * 1996-09-20 1998-03-26 Basf Ag Hetaroylderivate
AU9510998A (en) 1998-09-25 2000-04-17 Procter & Gamble Company, The Solid detergent compositions
BR112012007442B1 (pt) * 2009-09-25 2017-08-08 Bayer Intellectual Property Gmbh N- (1,2,5-oxadiazol-3-yl) benzamidasbenzamides, its uses, herbicide composition, and method for controlling undesired plants
US9035067B2 (en) * 2011-03-15 2015-05-19 Bayer Intellectual Property Gmbh N-(1,2,5-Oxadiazol-3-yl)-, N-(tetrazol-5-yl)- and N-(triazol-5-yl)bicycloarylcarboxamides and their use as herbicides
KR20140098140A (ko) * 2011-11-16 2014-08-07 바스프 에스이 치환 1,2,5-옥사디아졸 화합물 및 이들의 제초제 ｉｉ 로서의 용도

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2014037342A1 *

Also Published As

Publication number Publication date
JP2015528459A (ja) 2015-09-28
US20150216171A1 (en) 2015-08-06
CN104768937A (zh) 2015-07-08
CN104768937B (zh) 2016-11-23
BR112015004648A2 (pt) 2017-07-04
WO2014037342A1 (fr) 2014-03-13

Similar Documents

Publication Publication Date Title
WO2014037342A1 (fr) Amides d'acide bicycloarylcarboxylique à action herbicide
EP3356334B1 (fr) Derives acyle de n-(1,2,5-oxadiazol-3-yl)-, n-(1,3,4-oxadiazol-2-yl)-, n-(tetrazol-5-yl)- et n-(triazol-5-yl)-arylamide et leur utilisation comme des herbicides
ES2929395T3 (es) 4-difluorometil-benzoilamidas de acción herbicida
WO2013164331A1 (fr) Sels des amides d'acide n-(tétrazol-5-yl)-arylcarboxylique et n-(triazol-5-yl)arylcarboxylique, et leur utilisation comme herbicides
WO2017144402A1 (fr) Amides d'acide n-(5-halogèn-1,3,4-oxadiazol-2-yl)arylcarboxylique et leur utilisation comme herbicides
EP2855437B1 (fr) Thioamides dýacide carboxylique de n-(tétrazol-5-yl)- et n-(triazol-5-yl)aryle et leur utilisation comme herbicides
WO2014053473A1 (fr) 1,2,4-triazine-3,5-dione-6-carboxamides et leur utilisation comme herbicides
JP2015508766A (ja) 除草３−（スルフィン−／スルホンイミドイル）−ベンズアミド
WO2014086746A1 (fr) Amides d'acide n-(isoxazol-3-yl)-arylcarboxylique et leur utilisation comme herbicides
EP3317272A1 (fr) Dérivés de n-(1,3,4-oxadiazol-2-yl)arylcarboxamide à action herbicide
EP2928887A1 (fr) Amides d'acide n-(oxazol-2-yl)-arylcarboxylique et leur utilisation comme herbicides
BR112016030654B1 (pt) Benzamida e seu uso, composição herbicida e seu uso, método de controle de plantas indesejadas, ácido benzoico e cloreto de benzoil
JP6134380B2 (ja) ６−ピリドン−２−カルバモイル−アゾール類及び除草剤としてのそれらの使用
WO2015071205A1 (fr) Dérivés de pyridazinone et leur utilisation comme herbicides
WO2017005567A1 (fr) Dérivés de n-(tétrazol-5-yl)arylcarboxamide et n-(triazol-5-yl)arylcarboxamide à action herbicide
WO2016016107A1 (fr) Amides d'acide arylcarboxylique bicycliques et leur utilisation en tant qu'herbicides
EP3068772A1 (fr) Dérivés de 2-hétéroarylpyridazinone et leur utilisation comme herbicides
WO2015007662A1 (fr) Azin-2-on-3-carboxamide et leur utilisation comme herbicides
BR112018003545B1 (pt) Cetoxima benzoilamidas substituídas
WO2015007633A1 (fr) Dérivés de 6-azinon-2-carbonyle et leur utilisation comme herbicides
BR112016030725B1 (pt) Amidas de ácido benzoico ativas por meio de herbicida, composição herbicida, método de controle de plantas indesejadas, uso dos referidos compostos, ácido benzoico e cloreto de benzoil
EP2882732A1 (fr) Dérivés d'acide 6'-phényl-2,2'-bipyridin-3-carboxylique à action herbicide
BR112014029117B1 (pt) Tioamidas de ácido n-(tetrazol-5-il)- e n-(triazol-5-il)arilcarboxílico, uso das mesmas como herbicidas, composição herbicida e método para controlar plantas indesejadas
TW201348217A (zh) 具除草活性之亞磺醯－及磺醯亞胺醯基苯甲醯胺類
WO2014023669A1 (fr) Dérivés d'acide 2'-phényl-2,4'-bipyridin-3-carboxylique à action herbicide

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20150407

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20151028

RIN1 Information on inventor provided before grant (corrected)

Inventor name: KOEHN, ARNIM

Inventor name: LEHR, STEFAN

Inventor name: DIETRICH, HANSJOERG

Inventor name: ROSINGER, CHRISTOPHER HUGH

Inventor name: AHRENS, HARTMUT

Inventor name: BRAUN, RALF

Inventor name: SCHMUTZLER, DIRK

Inventor name: GATZWEILER, ELMAR

Inventor name: VAN ALMSICK, ANDREAS