EP3601242A1 - Amides d'acide n-(1,3,4-oxadiazol-2-yl)arylcarboxylique et leur utilisation comme herbicides - Google Patents

Amides d'acide n-(1,3,4-oxadiazol-2-yl)arylcarboxylique et leur utilisation comme herbicides

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Publication number
EP3601242A1
EP3601242A1 EP18712609.9A EP18712609A EP3601242A1 EP 3601242 A1 EP3601242 A1 EP 3601242A1 EP 18712609 A EP18712609 A EP 18712609A EP 3601242 A1 EP3601242 A1 EP 3601242A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
ome
methyl
cycloalkyl
oxadiazol
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Withdrawn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
EP18712609.9A
Other languages
German (de)
English (en)
Inventor
Arnim Köhn
Hartmut Ahrens
Christian Waldraff
Ralf Braun
Stephen David Lindell
Anu Bheemaiah MACHETTIRA
Elmar Gatzweiler
Christopher Hugh Rosinger
Hansjörg Dietrich
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
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Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP3601242A1 publication Critical patent/EP3601242A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • 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

Definitions

  • the invention relates to the technical field of herbicides, in particular the field of heterocyclic substituted arylcarboxamides for the selective control of weeds and grass weeds in crops.
  • Document WO 2012/028579 Al discloses N- (tetrazol-4-yl) benzamides and N- (triazol-3-yl) benzamides, which are subsituted in the 2-, 3- and 4-position of the phenyl ring and have a herbicidal activity.
  • Document WO 2014/184015 A1 also discloses N- (tetrazol-4-yl) -benzamides and N- (triazol-3-yl) -benzamides having a herbicidal action, those disclosed in document WO 2014/184015
  • the object of the present invention is therefore to provide further
  • N- (l, 3,4-oxadiazol-2-yl) benzamides having improved herbicidal activity.
  • N- (l, 3,4-oxadiazol-2-yl) arylcarbonklareamide according to claim 1, i. by N- (l, 3,4-oxadiazol-2-yl) arylcarboxamides of the formula (I) or salts thereof
  • R is hydrogen, halogen, (Ci-C 6 ) -alkyl, R'O-CCi-Cei-alkyl, CH 2 R 6 , (C 3 -C 7 ) -cycloalkyl, halo (Ci-C 6 ) -alkyl , (Ci-C6) alkoxy (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 - C 6) alkynyl , Halogeno (C 2 -C 6 ) -alkmyl, OR 1 , NHR 1 , methoxycarbonyl, ethoxycarbonyl,
  • s radicals selected from the group consisting of halogen, nitro, cyano, (Ci-C6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, S (0) 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 12) -alkyl, substituted heteroaryl , Heterocyclyl, benzyl or phenyl, X is nitro, halogen, cyano, formyl, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno ( C
  • Z represents hydrogen, nitro, halogen, cyano, thiocyanato, (Ci-C6) alkyl, (Ci-C6) alkoxy, halo (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, halogen - (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, halogen- (C 2 -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 4 ) -cycloalkyl, C 6) alkyl, R 1 (0) C, R ⁇ ON
  • Positions of the radicals V and W of the compound (1) may be either only V or only W hydrogen,
  • S 1 is a covalent bond or (C 1 -C 4 ) -alkanediyl
  • S 2 is (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -) C 6 ) alkenyl, (C 2 -C 6 ) -
  • S 3 is halogen, nitro, (C 1 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) haloalkynyl, (Ci-C 6) - alkoxy, (Ci-C 4) Alkoxy- (C 1 -C 4 ) -alkyl,
  • R 1 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) - haloalkenyl, (C2-C6) - Alkynyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkenyl, (C 3 -C 6 ) -halocycloalkyl, (C 1 -C 6 ) -alkyl-O- (Ci -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl- (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -
  • R 2 is (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -haloalkenyl, (C 2 - C 6) alkynyl , (C 2 -C 6 ) -haloalkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkenyl, (C 3 -C 6 ) - Halocycloalkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) alkyl, heteroaryl, (Ci-C 6) alkyl-heteroary
  • 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, represents (C 2 -C 6) -alkenyl or (C 2 -C 6) alkynyl,
  • R 5 is methyl or ethyl
  • R 6 is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl,
  • R 7 and R 8 are each independently (Ci-C6) alkyl, halo (Ci-C6) alkyl, (C3-C6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, phenyl, heteroaryl or heterocyclyl, where the three last-mentioned radicals are in each case represented by s radicals from the group consisting of nitro,
  • heterocyclyl carries n oxo groups, or R 7 and R 8 together with the sulfur atom to which they are attached form a 3- to 8-membered unsaturated, partially saturated or saturated ring which, in addition to the carbon atoms and the sulfur atom of the sulfoximino group, contains m ring members from the group from NCR 1 ), O and S (0) n , this ring being in each case represented by s radicals from the group consisting of nitro, halogen, cyano, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, R 1 0 (0) C, (R 1 ) 2 N (O) C, R'O, (R 1 ) 2 N, R 2 (O) n S, R 1 0 (O) 2 S, (R 1 ) 2 N (O) 2 S and
  • R 9 is substituted by s radicals from the group consisting of halogen, (C 3 -C 6) -cycloalkyl and R u O substituted (Ci-C6) alkyl,
  • R 10 is hydrogen, cyano, R u (0) C or (R u ) 2 N (0) C,
  • R 11 is hydrogen, (C 1 -C 6 ) -alkyl or halogeno (C 1 -C 6 ) -alkyl,
  • R 12 is hydrogen, cyano, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, halogeno (C 1 -C 6 ) -alkyl, OR 8 , SR 8 , or NR 8 R 9 , m means 0, 1 or 2 n means 0, 1 or 2, and s means 0, 1, 2 or 3, with the proviso that the compounds
  • N- (1,3,3-oxadiazol-2-yl) -arylcarboxamides of the invention differ from the known N- (1,3,3-oxadiazol-2-yl) -arylcarboxamides in particular by the additional substituents in the 5 and 6 positions of the phenyl part.
  • the essence of the invention relates to the surprising finding that in the case of N- (l, 3,4-oxadiazol-2-yl) arylcarbonklareamide the phenyl substituent, in the 5 and 6 position of the phenyl, im
  • 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.
  • 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 consisting of oxygen, nitrogen and sulfur, and may additionally be fused by a benzo ring.
  • 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 means an aromatic cyclic radical containing 3 to 6 ring atoms, of which 1 to 4 are from the group oxygen, nitrogen and sulfur, and additionally by a
  • Benzoring can be annealed.
  • heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl,
  • the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Similarly, stereoisomers occur when n is 1 (sulfoxides). 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.
  • R is hydrogen, halogen, (Ci-C i) -alkyl, halogeno (Ci-C i) -alkyl or (Ci-C i) -alkoxy- (Ci-C 4 ) -alkyl,
  • X is nitro, halo, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, OR 1, S (0) 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-S0 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 S0 2 R 2 , (C 1 -C 6 ) -alkyl Heteroaryl, (C 1 -C 6 ) -alkyl heterocyclyl, where the two last-mentioned radicals
  • Y is hydrogen, 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 2 -C 6 ) alkynyl, halo (C 2 -C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkenyl, halogen (C 3 -) C 6) cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, halo (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, COR 1, COOR ⁇ COOR ' ⁇ R'COOR 1 , C
  • Z represents hydrogen, nitro, halogen, cyano, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, halogeno (C 2 -C 6 ) alkynyl, (C 3 -C 6 ) -
  • V is hydrogen, halogen, cyano, nitro, (Ci-C i) -alkyl or (Ci-C 4 ) -haloalkyl,
  • W is halogen, cyano, nitro, (Ci-C 4 ) -alkyl or (Ci-C 4 ) -haloalkyl, wherein R 1 to R 12 and m, n and s are each independently defined as in claim 1, with the Provided that the connections
  • R is hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl or halogen
  • X is nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, methoxy, ethoxy,
  • Methylsulfanyl methylsulfinyl, methylsulfonyl, ethylsulfanyl, ethylsulfinyl, ethylsulfonyl,
  • Y is hydrogen, nitro, fluorine, chlorine, bromine, iodine, cyano, (Ci-C6) alkyl, halo (Ci-C6) - alkyl, OR 1, S (0) n R 2, S0 2 N (R 1 ) 2 , N (R 1 ) 2 , NR 1 S0 2 R 2 , NR'COR 1 ,
  • Ce -alkoxy, halogeno (Ci-C6) -alkoxy, (Ci-C6) -alkoxy- (Ci-C4) -alkyl and cyanomethyl substituted, and
  • Z denotes hydrogen, nitro, cyano, fluorine, chlorine, bromine or iodine
  • V is hydrogen, fluorine, methyl or trifluoromethyl (CF 3), W is fluorine, wherein R 1 to R 12 and m, n and s are each independently as defined above.
  • V is hydrogen
  • R, X, Y and Z and the radicals R 1 to R 12 and m, n and s are each independently as defined above.
  • N- (1,3,4-oxadiazol-2-yl) arylcarboxamides of the formula (I) in which A is C-Y in which
  • R is hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, or
  • X is nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, methoxy, ethoxy,
  • Methylsulfanyl methylsulfinyl, methylsulfonyl, ethylsulfanyl, ethylsulfinyl, ethylsulfonyl,
  • Y is hydrogen, 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 2 -C 6 ) alkynyl, halo (C 2 -C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkenyl, halogen (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
  • Z represents hydrogen, nitro, halogen, cyano, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, halogeno (C 2 -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, R 1 (O) C, R 1
  • V is hydrogen
  • W is fluorine
  • R 1 to R 12 and m, n and s are each independently as defined in claim 1, with the proviso that the compounds
  • X is nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, methoxy, ethoxy,
  • Methylsulfanyl methylsulfinyl, methylsulfonyl, ethylsulfanyl, ethylsulfinyl, ethylsulfonyl,
  • Y is hydrogen, nitro, fluorine, chlorine, bromine, iodine, cyano, (Ci-C6) alkyl, halo (Ci-C6) - alkyl, OR 1, S (0) n R 2, S0 2 N (R 1 ) 2 , N (R 1 ) 2 , NR 1 S0 2 R 2 , NR'COR 1 ,
  • Z is hydrogen, nitro, cyano, fluorine, chlorine, bromine or iodine
  • W means fluorine
  • R 1 to R 12 and m, n and s are each independently of one another as defined above, where in particular for the radicals R 1 and R 2 :
  • R 1 represents hydrogen, (Ci-C 6) -alkyl or (Ci-C 6) -haloalkyl
  • radicals R 1 except hydrogen, are substituted by s radicals from the group consisting of cyano, halogen and nitro,
  • R 2 is (Ci-C 6) -alkyl or (Ci-C 6) -haloalkyl
  • radicals R 2 are substituted by s radicals from the group consisting of cyano, halogen, nitro, and s is 0, 1, 2 or 3, with the proviso that the compounds
  • a particular aspect of the invention relates to N- (l, 3,4-oxadiazol-2-yl) arylcarboxamides of the formula (I) in which the substituents have the following meanings:
  • A is C-Y
  • R is hydrogen, methyl, ethyl, trifluoromethyl or methoxymethyl
  • X is fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl or cyclopropyl
  • Y is S (0) "R"
  • Z is trifluoromethyl, difluoromethyl or pentafluoroethyl
  • V is hydrogen
  • W represents fluorine
  • R 2 represents (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl
  • radicals R 2 are substituted by s radicals from the group consisting of cyano, halogen, nitro, n is 0, 1 or 2, s is 0, 1, 2 or 3.
  • A is C-Y
  • R is methyl
  • X is chlorine or methyl
  • Y is SMe, SOMe, or S0 2 Me
  • Z is trifluoromethyl or chlorine, V is hydrogen,
  • W is fluorine, particularly preferred in connection with the aforementioned particular aspect.
  • N- (l, 3,4-oxadiazol-2-yl) arylcarboxamides of the formula (I) in which A is C-Y in which
  • R is hydrogen, methyl, ethyl, trifluoromethyl or methoxymethyl
  • X is F, Cl, Br, CH 3, ethyl, n-propyl, iso-propyl, CF 3, 0-CH 2 -cycloproypl, or SMe S0 2 Me means
  • YH, F, Cl, Me, ethyl, propyl iso -propyl, CH 2 OMe, CH 2 OEt, CH 2 OCH 2 CHF 2 , CH 2 OCH 2 CF 3 , CH 2 OCH 2 CF 2 CHF 2 , CH 2 OcPentyl , CH 2 O-tetrahydrofuran-3-yl, CH 2 OCH 2 -tetrahydrofuran-2-yl, CH 2 OCH 2 -tetrahydrofuran-3-yl, CH 2 PO (OMe) 2 , COOMe, CONMe 2 , CONMe ( OMe), NH 2 ,
  • N- (l, 3,4-oxadiazol-2-yl) arylcarboxamides of formula (I) wherein A is N (rather than C-Y) are preferred wherein
  • V is hydrogen
  • R, X and Y and the radicals R 1 to R 12 and m, n and s are each independently as defined above.
  • the substituents and symbols, unless otherwise defined, have the same meaning as described for formula (I).
  • Compounds according to the invention can be prepared, for example, by the method indicated in Scheme 1 by base-catalyzed reaction of a benzoic acid or nicotinic acid chloride (II) with a 2-amino-1,3,4-oxadiazole (III):
  • benzoic acid chlorides of the formula (II) or the benzoic acids on which they are based are known in principle and can be described, for example, in accordance with the processes described in US Pat. No. 6,376,429 B1, EP 1 585 742 A1, WO2014 / 184015, WO2014 / 184016, WO2013 / 083859 and EP 1 202 978 A1 Methods are produced.
  • Amidation reactions such as. B. ⁇ , ⁇ -carbonyldiimidazole (CDI), dicyclohexyl-carbodiimide (DCC), 2,4,6-tripropyl-l, 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxides (T3P) etc . are used.
  • CDI ⁇ -carbonyldiimidazole
  • DCC dicyclohexyl-carbodiimide
  • T3P 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxides
  • the cyclization can, according to the in Synth. Commun. 31 (12), 1907-1912 (2001) or Indian J. Chem., Section B: Organic Chemistry Including Medicinal Chemistry; Vol. 43 (10), 2170-2174 (2004).
  • the compound of the formula V used in Scheme 3 can be prepared by reacting an acyl isocyanate of the formula VII with a hydrazide of the formula VI according to the method described in Synth. Commun. 25 (12), 1885-1892 (1995).
  • Collections of compounds of formula (I) and / or their salts, which may be synthesized following the above reactions, may also be prepared in a parallelized manner, which may be done in a manual, partially automated or fully automated manner. It is possible, for example, to automate the reaction procedure, the work-up or the purification of the products or intermediates. Overall, this is understood as a procedure, as described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (publisher Günther Jung), Verlag Wiley 1999, on pages 1 to 34 is described.
  • Chromatographieapparaturen available, for example, the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.
  • 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.
  • Solid-phase assisted synthesis methods allow a number of protocols known from the literature, which in turn can be performed 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. Both solid and liquid phases may require the performance of one or more
  • Present invention are also libraries containing at least two compounds of formula (I) and their salts.
  • the present invention therefore also provides a method for controlling
  • Plant cultures in which one or more compounds of the invention (s) on the plants eg harmful plants such as mono- or dicotyledonous weeds or undesirable crops
  • the seed eg grains, seeds or vegetative propagules such as tubers or sprouts with buds
  • the area on the plants grow eg the acreage
  • the compounds of the invention may be e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence or Nachauflaufmaschinen 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 before germination, then either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die off completely after a lapse of three to four weeks.
  • the active ingredients are applied to the green parts of the plants postemergence, growth stops after the treatment and the harmful plants remain in the growth stage existing at the time of application or die completely after a certain time, so that a weed competition harmful to the crop plants takes place very early and sustainably eliminated.
  • the compounds of the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops, e.g. dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Pineapple, Asparagus , Avena, Hordeum, Oryza, Panicum, Saccharum, Seeal, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, depending on the structure of the respective compound of the invention and their application rate only insignificantly or not at all damaged.
  • the present compounds are very well suited for the selective control of undesired plant growth in crops such as agricultural crops or ornamental plants.
  • the compounds according to the invention (depending on their respective structure and the applied application rate) have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as by
  • Triggering of desiccation and stunting are used. 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 for controlling harmful plants in crops of genetic or conventional Mutagenesis modified plants are used.
  • 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 properties relate to z.
  • transgenic crops Fatty acid composition of the crop known.
  • transgenic crops is the use of the compounds of the invention in economically important transgenic crops of useful and ornamental plants, eg.
  • 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 compounds of the invention in economically important transgenic crops of useful and ornamental plants, eg.
  • 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.
  • Compounds of the invention are used as herbicides in crops that are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
  • 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 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 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
  • Compounds of the invention are used as herbicides in crops that are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
  • transgenic crops which are resistant to certain glufosinate-type herbicides (cf., for example, EP-A-0242236, EP-A-242246) or glyphosates
  • transgenic crops for example cotton, with the ability
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins (Bt toxins) to produce, which the
  • transgenic crops which are characterized by higher yields or better quality transgenic crops characterized by a combination of z.
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration 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, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Gene and Clones", VCH Weinheim 2nd edition, 1996
  • 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 corresponding antisense RNA, a sense RNA to obtain a cosuppression effect, or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules can be used which encode the entire
  • a sequence of a gene product including any flanking sequences, 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 of DNA sequences having a high degree of homology to the coding sequences of a
  • 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 to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (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).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants can in principle be plants of any one
  • Plant species that is, both monocotyledonous and dicotyledonous plants.
  • the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against herbicides, the essential plant enzymes, eg. 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.
  • the essential plant enzymes eg. 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.
  • the active compounds according to the invention in addition to the effects observed in other crops on harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops.
  • the invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules are used in the usual preparations.
  • 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.
  • 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 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.
  • WP wettable powder
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW emulsions
  • SC Suspension concentrates
  • SC oil- or water-based dispersions
  • auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticides Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J., H.v. Olphen,
  • Suitable safeners are, for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl,
  • Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, also contain surfactants of an ionic and / or nonionic type (wetting agent,
  • Dispersants for example polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, ligninsulfonsaures Sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltaurine acid.
  • the herbicidal active ingredients are finely ground, for example, in conventional apparatus such as hammer mills, blower mills and air jet mills and simultaneously or subsequently with the
  • Formulation aids mixed.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, 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).
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents
  • surfactants of ionic and / or nonionic type emulsifiers
  • 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 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.
  • 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. are already listed above for the other formulation types.
  • Emulsions e.g. Oil-in-water (EW) emulsions may be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants such as those described e.g. listed above for the other formulation types.
  • EW Oil-in-water
  • Granules can either be prepared by atomizing the active ingredient on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the
  • 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 .-%.
  • 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.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreezing and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent.
  • combination partners for the compounds according to the invention in mixture formulations or in the tank mix are known active compounds which are based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine Synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase are based, can be used, such as from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 15th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2009 and cited therein.
  • herbicides or plant growth regulators with the inventive
  • Compounds which can be combined include, for example, the following active substances (the compounds are denoted either by the “common name” according to the International Organization for Standardization (ISO) or by the chemical name or by the code number) and always include all forms of application, such as acids, Salts, esters and isomers such as stereoisomers and optical isomers.
  • active substances the compounds are denoted either by the "common name” according to the International Organization for Standardization (ISO) or by the chemical name or by the code number
  • ISO International Organization for Standardization
  • isomers such as stereoisomers and optical isomers.
  • Acetochlor acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfamate, ancymidol, anilofos, asulam, Atrazines, azafenidine, azimsulfuron, aziprotryn, beflubutamide, benazoline, benazolin-ethyl,
  • Chlorfenac Chlorfenac Sodium, Chlorfenprop, Chlorflurenol, Chlorflurenol-methyl, Chloridazon, Chlorimuron, Chlorimuron-ethyl, Chlormequat-chloride, Chlornitrofen, Chlorophthalim, Chlorthal-dimethyl, Chlorotoluron, Chlorsulfuron, Cinidon, Cinidon-ethyl, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop, clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop, clopyralid,
  • Cloransulam Cloransulam-methyl, Cumyluron, Cyanamide, Cyanazine, Cyclanilide, Cycloate, Cyclosulfamuron, Cycloxydim, Cycluron, Cyhalofop, Cyhalofop-butyl, Cyperquat, Cyprazine, Cyprazole, 2,4-D, 2,4-DB, Daimuron / Dymron, Dalapon, Daminozide, Dazomet, n-Decanol,
  • MCPA MCPB
  • MCPB-methyl -ethyl and -sodium, mecoprop, mecoprop-sodium, mecoprop-butotyl, mecoprop-p-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, Mefenacet, Mefluidide, mepiquat chloride, mesosulfuron, mesosulfuron-methyl, mesotrione,
  • Methyl isothiocyanate metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam,
  • Oxadiazone oxasulfuron, oxaziclomefones, oxyfluorfen, paclobutrazole, paraquat, paraquat dichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone,
  • Perfluidone Pethoxamide, Phenisopham, Phenmedipham, Phenmediphamethyl, Picloram, Picolinafen, Pinoxaden, Piperophos, Pirifenop, Pirifenop-butyl, Pretilachlor, Primisulfuron, Primisulfuron-methyl, Probenazoles, Profluazole, Procyazine, Prodiamine, Prifluralines, Profoxydim, Prohexadione,
  • 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. Dust-like preparations, soil or
  • Spreading granulates and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the external conditions such as temperature, humidity, the type of herbicide used, inter alia, the required application rate of the compounds of the formula (I) varies. It can vary within wide limits, for example between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha.
  • aqueous phase is acidified to pH 4 with a 2M HCl solution and then extracted with t -bityl methyl ether.
  • the organic phase is dried over sodium sulfate, filtered and concentrated. Yield: 10 g (39 mmol, 78%).
  • reaction mixture was warmed to room temperature and stirred for 14 h at room temperature.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne des amides d'acide N-(1,3,4-oxadiazol-2-yl)arylcarboxylique de formule (I) ou leurs sels (I), ainsi que leur utilisation comme herbicides.
EP18712609.9A 2017-03-30 2018-03-22 Amides d'acide n-(1,3,4-oxadiazol-2-yl)arylcarboxylique et leur utilisation comme herbicides Withdrawn EP3601242A1 (fr)

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EP17163727 2017-03-30
PCT/EP2018/057268 WO2018177871A1 (fr) 2017-03-30 2018-03-22 Amides d'acide n-(1,3,4-oxadiazol-2-yl)arylcarboxylique et leur utilisation comme herbicides

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MX2019011774A (es) 2019-11-18
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CN110520414B (zh) 2023-11-28
WO2018177871A1 (fr) 2018-10-04
JP7277374B2 (ja) 2023-05-18
ZA201907150B (en) 2021-06-30
US20210076680A1 (en) 2021-03-18
BR112019020467A2 (pt) 2020-05-12
EA201992259A1 (ru) 2020-03-19
US11304418B2 (en) 2022-04-19
AU2018241490A1 (en) 2019-10-17
CN110520414A (zh) 2019-11-29
AR111301A1 (es) 2019-06-26
BR112019020467B1 (pt) 2023-02-07
JP2020515593A (ja) 2020-05-28
AU2018241490B2 (en) 2022-07-21

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