[go: up one dir, main page]

EP2892345A1 - Utilisation de 2-amidobenzimidazoles, de 2-amidobenzoxazoles et de 2-amidobenzothiazoles substitués ou de leurs sels comme principes actifs contre le stress abiotique des plantes - Google Patents

Utilisation de 2-amidobenzimidazoles, de 2-amidobenzoxazoles et de 2-amidobenzothiazoles substitués ou de leurs sels comme principes actifs contre le stress abiotique des plantes

Info

Publication number
EP2892345A1
EP2892345A1 EP13758839.8A EP13758839A EP2892345A1 EP 2892345 A1 EP2892345 A1 EP 2892345A1 EP 13758839 A EP13758839 A EP 13758839A EP 2892345 A1 EP2892345 A1 EP 2892345A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
heterocyclyl
aryl
amino
alkoxy
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Withdrawn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
EP13758839.8A
Other languages
German (de)
English (en)
Inventor
Jens Frackenpohl
Ines Heinemann
Thomas Müller
Jan Dittgen
Pascal VON KOSKULL-DÖRING
Dirk Schmutzler
Martin Jeffrey Hills
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 EP13758839.8A priority Critical patent/EP2892345A1/fr
Publication of EP2892345A1 publication Critical patent/EP2892345A1/fr
Withdrawn legal-status Critical Current

Links

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
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/10—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/14—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D401/10—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 carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D409/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D413/10—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 carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Definitions

  • the invention relates to the use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoie and 2-amidobenzothiazoles or their salts as active ingredients for increasing the stress tolerance in plants to abiotic stress, in particular for strengthening the plant growth and / or to increase the plant yield. It is known that certain substituted benzimidazoles as
  • Pesticides used see W094 / 1 1349) and that certain haloalkyl-substituted 2-Amidobenzimidazole can be used as active ingredients against abiotic plant stress (see WO201 1 107504). It is also known that substituted amidobenzimidazoie as pharmaceutical agents (see WO2000029384 and WO2000026192) and cosmetic
  • WO97 / 04771 also describes the pharmaceutical use of predominantly aryl-substituted benzimidazoles, while in WO2000032579 heterocyclyl-substituted benzimidazoles are described.
  • the preparation of heterocyclyl-substituted benzimidazoles and their inhibiting action on enzymes from the family of the poly (ADP-ribose) polymerase is described, for example, in Org. Proc. Res Devel. 2007, 11, 693; J. Med. Chem. 2009, 52, 1619 and J. Med. Chem. 2009, 52, 514, while J. Med. Chem. 2010, 53, 3142 disclose methods of preparation for providing specific aryl-substituted benzimidazoles ,
  • abiotic stress defense reactions e.g., cold, heat, drought, salt, flooding
  • signal transduction chains e.g., transcription factors, kinases, phosphatases
  • the signal chain genes of the abiotic stress reaction include, among others.
  • ROS reactive oxygen species
  • HSF Heat Shock Factors
  • HSP Heat Shock Proteins
  • Substances or their stable synthetic derivatives and derived structures are also effective in external application to plants or seed dressing and activate defense reactions that result in an increased stress or pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589].
  • osmolytes e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives have been observed (Chen et al., 2000, Plant Cell Environ 23: 609-618, Bergmann et al., DE-4103253).
  • the action of antioxidants such as naphtols and xanthines to increase the abiotic stress tolerance in plants has also been described (Bergmann et al., DD-277832, Bergmann et al., DD-277835).
  • the molecular causes of the anti-stress effects of these substances are largely unknown.
  • PARP poly-ADP-ribose polymerases
  • PARG poly (ADP-ribose) glycohydrolases
  • the object of the present invention was to provide further compounds which increase the tolerance to abiotic stress in plants.
  • the present invention accordingly provides for the use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles
  • R 1 , R 2 , R 3 independently of one another represent hydrogen, halogen, alkyl, cycloalkyl,
  • R 1 and R 2 with the atoms to which they are attached form a completely saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring,
  • R 2 and R 3 with the atoms to which they are attached, a fully saturated, form part-saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring,
  • W stands for oxygen, sulfur,
  • X is oxygen, sulfur, NR 4 ,
  • R 4 is hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cyanoalkyl,
  • Q is alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, aryl, arylalkyl,
  • heteroarylalkyl heterocyclylalkyl, heteroaryl, heterocyclyl, heterocyclylaryl, heterocyclylheteroaryl, heteroarylheteroaryl, heteroarylaryl, arylaryl,
  • Arylalkylaminocarbonyl aminocarbonyl, alkylaminocarbonyl,
  • Cycloalkylaminocarbonyl bis-alkylaminocarbonyl, heterocyclyl-N-carbonyl, imino, alkylimino, arylimino, cycloalkylimino, cycloalkylalkylimino,
  • Cycloalkylaminoalkyl alkoxy (alkoxy) alkyl, arylalkoxyalkylaryl, heterocyclyl-N-alkylaryl, aryl (alkyl) aminoalkylaryl, arylalkyl (alkyl) aminoalkylaryl,
  • Alkoxycarbonylalkylaminoalkylaryl alkoxycarbonylalkyl (alkyl) aminoalkylaryl, heteroaryl (alkyl) aminoalkylaryl, heteroarylalkyl (alkyl) aminoalkylaryl,
  • Z 2 is hydrogen, alkyl, cycloalkyl, branched or unbranched haloalkyl, aikinyl, alkenyl, cyanoalkyl, arylalkyl, heteroarylalkyl, alkylcarbonyl,
  • Alkoxycarbonyl is or
  • Z 1 and Z 2 together are part of an optionally substituted Sulfilimin- or amidine group or form a iminophosphorane.
  • the compounds of general 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.
  • 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 form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • These salts then contain the conjugate base of the acid as an anion.
  • Cycloalkyl (-, the inventive use of compounds of general formula (I) wherein R 1, R 2, R 3 are independently hydrogen, halogen, (Ci-C 8) -alkyl, (C 3 -C 8) is preferably C 4 -C 8) cycloalkenyl, (C 3 -C 8) halocycloalkyl, (C 2 -C 8) alkenyl, (C2-C8) -alkynyl, optionally substituted phenyl, aryl (Ci-C 8) -alkyl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (Ci -C 8) alkyl, (dC 8) alkylthio, (Ci-C
  • Cycloalkoxy (C 3 -C 8) cycloalkyl (Ci-C8) alkoxy, aryloxy, Heteroraryloxy,
  • R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • interrupted and optionally further substituted 5 to 7-membered ring represents oxygen, sulfur,
  • X represents oxygen, sulfur, NR 4, represents hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) cycloalkyl (Ci-C8) - alkyl , (C 4 -C 8) cycloalkenyl, cyano (Ci-C 8) alkyl, (C 2 -C 8) alkenyl (Ci-C 8) alkyl, (Ci-C 8) haloalkyl, (C 2 -C 8) alkynyl (Ci-C 8) alkyl, aryl (Ci-C 8) alkyl, heteroaryl (dC 8) alkyl, heterocyclyl (Ci-C8) alkyl, (Ci-C 8) alkylcarbonyl, (C 3 -C 8) - cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (Ci-C 8)
  • Z 2 is hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) -Cyc Oalkyl, (Ci-C8) -haloalkyl, (C 2 -C 8) - alkynyl, (C 2 -C 8 ) alkenyl, cyano (Ci-C 8 ) alkyl, aryl (Ci-C 8 ) alkyl, heteroaryl (Ci-Cs) alkyl, (Ci-C 8 ) alkylcarbonyl, (Ci-C 8 ) alkoxycarbonyl or
  • Z 1 and Z 2 together form a N- (bis (Ci-C8) alkyl) sulfanyliden-, N- (aryl (dC 8) - alkyl) sulfanyliden-, N- (bis- (C 3 -C 8 ) -Cycloalkyl) sulfanylidene, N - ((C 1 -C 8 ) -alkyl
  • R 1 , R 2 , R 3 independently of one another represent hydrogen, iodine, bromine, chlorine, fluorine, (C 1 -C 7 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 7 ) -cycloalkenyl, ( C 3 -C 7 ) -halocycloalkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 4) -alkyl, aryl- (C 2 -C) -alkenyl , Heteroaryl, heteroaryl (Ci-C /) - alkyl, heterocyclyl,
  • Alkylamino bis - [(Ci-C 7 ) -alkyl] amino, (Ci-C 7 ) - Aikylcarbonylamino, (C3-C7) - Cycloalkyicarbonylamino, Arylcarbonylamino, (Ci-C) -Aikoxycarbonylamino, Heterocyclyi- (Ci-C 7 ) -alkoxy, (C 3 -C 7 ) -cycloalkyl-(C 1 -C 4 ) -alkyl, (C 2 -C 7 ) -hioacylic, (C 2 -C 6) -haloalkynyl, heterocyciyl- (C 2 -) C /) alkynyl, (C3-C7) halocycloalkoxy, (C 2 -C) -haloalkylinyloxy, arylthio, heteroaryithio, (C 1 -C
  • R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • W stands for oxygen, sulfur,
  • X is oxygen, sulfur, NR 4, R 4 is hydrogen, (dC /) - alkyl, (C 3 -C 7) -cycloalkyl, (C 3 -C 7) cycloalkyl (Ci-C7) - alkyl , (C 4 -C 7) cycloalkenyl, cyano (Ci-C /) - alkyl, (C 2 -C 7) alkenyl (Ci-C7) alkyl, (Ci-C7) haloalkyl, (C 2 -C 6) -alkynyl- (C 1 -C 4) -alkyl, aryl- (C 1 -C 4) -alkyl, heteroaryl- (C 1 -C 6) -alkyl, heterocyclyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylcarbonyl, (C 3 -C 7 ) -cycl
  • heterocyclyl heterocyclylaryl, heterocyclylheteroaryl, heteroarylheteroaryl, heteroarylaryl, arylaryl, aryloxyaryl, aryl- (C 2 -C 7 ) -alkenyl, heteroaryl- (C 2 -C) -alkenyl, heterocyclyl- (C 2 -C 7 ) -alkenyl, aryl- (C 2 -C /) - alkynyl, heteroaryl (C 2 -C 7) - alkynyl, heterocyclyl (Ci-C7) alkynyl, (C 3 -C /) - cycloalkyl- (C 2 -C 7) -alkynyl, ( C1-C7) -alkylamino- (C 1 -C 7 ) -alkyl, bis- [(C 1 -C 4) -alkyl] amino- (C 1 -C 4)
  • Z 1 represents hydrogen, hydroxy, (C 1 -C 4 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -
  • Halocycloalkyl bromine, chlorine, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 7 ) -alkynyl, (C 2 -C / ) Alkenyl, cyano- (Ci-C /) - alkyl, nitro (Ci-C /) - alkyl, amino- (Ci-C /) - alkyl, alkyl- (Ci-C 7 ) -amino- (Ci -C 7) alkyl, - bis [(Ci-C) alkyl] amino- (Ci-C7) alkyl, (C 2 -C 7) alkynyl (Ci-C7) alkyl, aryl (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 4 ) -
  • Z 2 is hydrogen, (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 7 ) -alkynyl, (C 2 -C /) Alkenyl, cyano- (Ci-C /) - alkyl, aryl- (Ci-C 7 ) -alkyl, heteroaryl- (Ci-C 7 ) -alkyl, (Ci-C /) - alkylcarbonyl, (Ci-C 7 ) Alkoxycarbonyl or
  • R 1 , R 3 and R 3 independently of one another represent hydrogen, iodine, bromine, chlorine, fluorine, (C 1 -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 3 -C 6 ) -halocycloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 4 ) -alkyl, aryl- (C 2 -C 4 ) -alkenyl, Heteroaryl, heteroaryl- (C 1 -C 4) -alkyl, heterocyclyl,
  • R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • X is oxygen, sulfur, NR 4 ,
  • R 4 represents hydrogen, (Ci-C 4) -alkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C4) - alkyl, (C 4 -C 6) cycloalkenyl, cyano (Ci-C 4) alkyl, (C2-C4) alkenyl (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 2 -C) alkynyl ( C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl, heterocyclyl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylcarbonyl, ( C 3 -C 6) - cycloalkylcarbonyl, arylcarbon
  • Q is (C 1 -C 4 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 4 -C 6) cycloalkenyl, optionally substituted phenyl, aryl- (Ci-C4) - alkyl, heteroaryl (Ci-C) alkyl, heterocyclyl (Ci-C 4) alkyl, heteroaryl,
  • Heterocyclyl (Ci-C 4) alkyl, (dC 4) alkylcarbonyl, (Ci-C 4) alkoxycarbonyl, (C 3 -C 6) cycloalkoxycarbonyl, (Ci-C 4) alkylsulfonyl, arylsulfonyl,
  • Residue definitions apply both to the end products of the formula (I) and
  • R ⁇ R 2 , R 3 independently of one another represent hydrogen, halogen, (C 1 -C 6 -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) -halocycloalkyl , (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 8 ) -alkyl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl, heteroaryl- C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8
  • R 1 and R 2 with the atoms to which they are attached form a completely saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring, R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • W is oxygen, sulfur, X is oxygen, sulfur is,
  • Q is (Ci-C 8) haloalkyl, (Ci-C 8) alkoxy (Ci-C8) -haloalkyl, (C 3 -C 8) halocycloalkyl, (Ci-C8) haloalkoxy (dC 8 ) -haloalkyl, aryl- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -haloalkyl, bis [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 4) -alkyl C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl,
  • Z 1 is hydrogen, hydroxy, (C 1 -C 5 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -
  • Z 2 is hydrogen, (DC 8) alkyl, (C 3 -C 8) cycloalkyl, (DC 8) -haloalkyl, (C 2 -C 8) - alkynyl, (C 2 -C 8) alkenyl, cyano - (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (C 1 -C 8 ) -alkoxycarbonyl or
  • R ⁇ R 2, R 3 are independently hydrogen, halogen, (Ci-C 4) -alkyl, (C 3 -C 8) - cycloalkyl, (C 4 -C 8) cycloalkenyl, (C 3 -C 8) -Halocycloalkyl, (C 2 -C 4 ) -alkenyl,
  • (C 2 -C 4 ) -alkynyl optionally substituted phenyl, aryl- (C 1 -C 4 ) -alkyl, aryl- (C 2 -C 5) -alkenyl, heteroaryl, heteroaryl- (C 1 -C 4 ) -alkyl, heterocyclyl, heterocyclyl -
  • R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • W is oxygen, sulfur, X is oxygen, sulfur, Q is (Ci-C /) - haloalkyl, (Ci-C 4) alkoxy (Ci-C 4) -haloalkyl, (C 3 -C 8) halocycloalkyl,
  • Z 1 represents hydrogen, hydroxy, (Ci-C 4) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) - halocycloalkyl, halogen, (C2-C4) alkenyl (Ci C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl,
  • Z 2 is hydrogen, (Ci-C 4) -alkyl, (C 3 -C 8) -Cyc Oalkyl, (Ci-C 4) -haloalkyl, (C2-C4) - alkynyl, (C2-C4) - Alkenyl, cyano- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 ) Alkoxycarbonyl or
  • Z 1 and Z 2 together form a N- (bis (C 1 -C 6 ) alkyl) sulfanylidene, N- (aryl- (C 1 -C 6 ) -alkyl) sulfanylidene, N- (bis (C 3 -C 7 ) -Cycloalkyl) sulfanylidene, N - ((C 1 -C 6 ) -alkyl-
  • R 2 , R 3 independently of one another represent hydrogen, halogen, (C 1 -C 6 -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) -halocycsoalkyl, (C 2 -C 8) alkenyl, (C2-C8) -alkynyl, optionally substituted phenyl, aryl (Ci-C8) alkyl, aryl (C2-C8) alkenyl, heteroaryl, heteroaryl (Ci- C8) alkyl, heterocyclyl, heterocyclyl (Ci-C8) alkyl, (Ci-C 8 () alkoxy- Ci-C 8) alkyl, (CrC 8) alkylthio, (Ci-C 8) - haloalkylthio, (Ci-C 8) haloalkyl, (Ci-C
  • R 1 and R 2 contain the atoms they are bonded, form a fully saturated, partially saturated or unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring, R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or form unsaturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 7-membered ring, W for oxygen, sulfur! sees
  • X is NR 4 ,
  • R 4 represents hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) -Cyc oa ky -! (Ci-C8) - alkyl, (C 4 -C 8) cycloalkenyl, cyano (Ci-C8) -a! kyl, (C 2 -C 8) alkenyl (Ci-C 8) alkyl, (Ci-C 8) -Ha! oa !
  • kyl (C 2 -C 8) alkynyl (Ci-C 8) alkyl, aryl (Ci-C 8) -alkyS, heteroaryl (Ci-Cs) -a! kyl, heterocyclyl (Ci- C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl, (C 3 -C 8 ) -cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 1 -C 8 ) -haloalkylcarbonyl, heterocyclylcarbonyl, aryl- (C 1 -C 8 ) -alkylcarbonyl , (C 1 -C 8 ) -alkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl- (C
  • Q is (Ci-C 8) alkyl, (C 2 -C 8) -alkenyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) - alkyl, (C 4 -C 8 ) -cycloalkenyl, optionally substituted phenyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryi (C 1 -C 8 ) -acyl, heterocyclyl- (C 1 -C 8 ) -alkyl, heteroaryl,
  • heterocyclyl heterocyclylaryl, heterocyclylheteroaryl, heteroarylheteroaryl, heteroarylaryl, arylaryl, aryloxyaryl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl- (C 2 -C 8 ) -alkenyl, heterocyclyl- (C 2 -C 8 ) -alkenyl, aryl- C2-C8) alkynyl, heteroaryl (C2-C8) - alkynyl, heterocyclyl (Ci-C8) -alkynyl, (C 3 -C 8) -Cycloalky - (C2-C8) -a!
  • Aryloxyheteroaryl (Ci-C8) alkylsulfinyl, (Ci-C 8) - alkylthio, (Ci-C 8) -A kylsulfonyl, (C3-C8) cycloalkylsulfinyl, (C 3 -C 8) -cycloalkylthio , (C 3 -C 8) -cycloalkylsulfonyl, arylsulfinyl, arylthio, arylsulfonyl, amino, (C 1 -C 8 ) -alkylamino, bis - [(C 1 -C 8 ) -alkyl] amino, arylamino, aryl- (C 1 -C 8 ) alkylamino, (C 3 -C 8 ) -cycloalkylamino, formyl, (C 1 -C 8 ) -alkylcarbonyl,
  • Z 1 and Z 2 together form a N- (bis (C 1 -C 8 ) -acyl) sulfanylidene, N- (aryl- (C 1 -C 8 ) -alkyl) sulfanylidene, N- (bis (C 3 -C 8 ) Cycloalkyl) sulfanylidene, N - ((C 1 -C 8 ) alkyl (C 3 -C 8 ) cycloalkyl) sulfanylidene group or an N, N-di (C 1 -C 8) alkylformylidene group.
  • R 1 , R 3 and R 3 independently of one another are hydrogen, halogen, (C 1 -C 4 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 3 -C 8 ) - Halocycloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, optionally substituted phenyl, aryl- (C 1 -C 4 ) -alkyl, aryl- (C 2 -C 4 ) -alkenyl, heteroaryl, heteroaryl- (C 1 -C 4 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C
  • R 1 and R 2 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • R 2 and R 3 with the atoms to which they are attached, a fully saturated, partially saturated or unsaturated, optionally by heteroatoms
  • W is oxygen, sulfur, X is NR 4 ,
  • R 4 represents hydrogen, (Ci-C 4) -alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) -cycloalkyl- (Ci-C4) - alkyl, (C4-C8) - cycloalkenyl, cyano (Ci-C 4) alkyl, (C2-C4) alkenyl (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C2-C4) alkynyl (Ci- C 4) alkyl, aryl (Ci-C 4) alkyl, heteroaryl (Ci-C 4) alkyl, heterocyclyl (Ci-C 4) alkyl, (Ci-C 4) alkylcarbonyl, (C 3 -C 8 ) -cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 1 -C 4 ) -haloalkyl
  • Z 1 and Z 2 together form an N- (bis (C 1 -C 4) alkyl) sulfanylidene, N- (aryl- (C 1 -C 4) -alkyl) sulfanylidene, N- (bis- (C 3 -C 8 ) Cycloalkyl) sulfanylidene, N - ((C 1 -C 4 ) -alkyl- (C 3 -C 8) -cycloalkyl) sulfanylidene group or an N, N-di- (C 1 -C 4 ) -alkylformylidene group.
  • arylsulfonyl is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, here in particular optionally substituted naphthylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino,
  • Alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups
  • cycloalkylsulfonyl alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
  • alkylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably having 1 to 8, or having 1 to 6 carbon atoms such as methylsulfonyl,
  • heteroarylsulfonyl is optionally substituted
  • substituted polycyclic heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino,
  • Alkylcarbonylamino, dialkylamino or alkoxy groups Alkylcarbonylamino, dialkylamino or alkoxy groups.
  • alkylthio alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n- Butylthio, isobutylthio, sec-butylthio and tert-butylthio.
  • Alkenylthio represents an alkenyl radical bonded via a sulfur atom
  • alkynylthio represents an alkynyl radical bonded via a sulfur atom
  • cycloalkylthio represents a cycloalkyl radical bonded via a sulfur atom
  • cycloalkenylthio represents a cycloalkenyl radical bonded via a sulfur atom
  • Alkoxy means an alkyl radical bonded via an oxygen atom
  • alkenyloxy represents an alkynyl radical bound via an oxygen atom
  • alkynyloxy means an alkynyl radical bound via an oxygen atom
  • cycloalkyloxy denotes a cycloalkyl radical bonded via an oxygen atom
  • cycloalkynyloxy denotes a cycloalkenyl radical bonded via an oxygen atom.
  • aryl means an optionally substituted mono-, bi- or
  • polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, the binding site being on the aromatic system.
  • Aryl is also generally known from the term “optionally substituted phenyl ".
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl,
  • heterocyclic ring preferably contains 3 to 9 ring atoms, especially 3 to 6
  • Ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two oxygen atoms should be directly adjacent, as
  • heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrole-2 or 3-yl, 2,3-dihydro-1 H-pyrrole 1- or 2- or
  • 2- or 3-tetrahydrothiophenyl 2,3-dihydrothiophene-2 or 3 or 4 or 5-yl; 2,5-dihydrothiophene-2 or 3-yl; Tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 3,6-dihydro-2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 2H-thiopyran-2 or 3 or 4 or 5 or 6-yl; 4H-thiopyran-2- or 3- or 4-yl.
  • Preferred 3-membered and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -Dioxetan-2-yl. Further examples of
  • Heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3 or 4 or 5-yl; 4,5-dihydro-1H-pyrazole-1 or 3 or 4 or 5-yl; 2,3-dihydro-1H-pyrazole-1 - or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazole-1 - or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; Hexahydropyridazine-1 - or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazine-1 -
  • 5- or 6-yl 5,6-dihydro-4H-1,2-oxazine-3- or 4- or 5- or 6-yl; 2H-1, 2-oxazine-2 or 3 or 4 or 5 or 6-yl; 6H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 4H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 1,3-oxazinan-2 or 3 or 4 or 5 or 6-yl;
  • 6- or 7-yl 1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; isothiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazole-2- or 3- or 4- or 5-yl; 2,5-dihydroisothiazole-2 or 3 or 4 or 5-yl; 4,5-dihydroisothiazole-3 or 4 or 5-yl; 1,3-thiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1, 3-thiazole-2 or 3 or
  • Heterocycly are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as 1, 4,2-Dioxazo! idin-2- or 3- or 5-yl; 1, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,2,2,2-dioxazine-3- or 5- or 6-yl; 1,2,2-dioxazine-3- or 5- or 6-yl; 1, 4,2-dioxazepan-2 or 3 or 5 or 6 or 7-yl; 6,7-dihydro-5H-1, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 2,3-dihydro-7H-, 4,2-dioxazepin-2 or 3 or 5 or 6 or 7-yl; 2,3-dihydro-5H-1,2,2-dio
  • heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl,
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo.
  • Oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
  • lactones and lactams are preferably also included.
  • the oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. in the case of N and S, for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring.
  • N and S for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring.
  • -N (O) and -S (O) groups both enantiomers are included.
  • heteroaryl is heteroaromatic
  • Heteroaryls of the invention are, for example, 1H-pyrro-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazole-1-yl; 1 H-imidazol-2-yl; 1 H -imidazol-4-yl; 1 H -imidazol-5-yl; 1H-pyrazole-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1 H-pyrazol-5-yl, 1 H-1, 2,3-triazol-1-yl, 1 H-1, 2,3-triazol-4-yl, 1 H-1, 2,3-triazole 5-yl, 2H-1, 2,3-triazol-2-yl, 2H-1, 2,3-triazol-4-yl, 1H-1, 2,4-triazol-1-y
  • heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
  • quinolines for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
  • quinoxaline for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • quinoxaline e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-
  • quinazoline cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine;
  • heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indole-4 yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4 -yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl , 1-benzothiophene-5-yl, 1-benzothiophene
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alky Denotes a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally mono- or polysubstituted, preferably unsubstituted, Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino- or nitro groups, particular preference is given to methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine.
  • Haloalkyl means the same or different
  • Polyhaloalkyl such. B. CH2CHFCI, CF2CCIFH, CF 2 CBrFH, CH2CF3;
  • perhaloalkyl also encompasses the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated
  • Hydrocarbon which is mono- or polysubstituted by fluorine, wherein the corresponding fluorine atoms as substituents on one or more
  • Hydrocarbon chain can be located, such as. B. CHFCH3, CH2CH2F, CH2CH2CF3, CHF 2, CH 2 F, CHFCF2CF3
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, all other optionally present
  • Halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the
  • Haloalkoxy is eg OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl;
  • (C 1 -C 4) -alkyl given here by way of example means a A shorthand notation for straight-chain or branched alkyl having one to 4 carbon atoms corresponding to the range for C atoms, ie, the radicals comprises methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl , General alkyl radicals having a larger specified range of carbon atoms, eg. B. "(Ci-C-6) -alkyl", accordingly also include straight-chain or branched alkyl radicals having a larger number of carbon atoms, ie according to Example, the alkyl radicals having 5 and 6 carbon atoms.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl, even in assembled radicals, are the lower
  • Carbon skeletons e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred.
  • Alkyl radicals also in the assembled radicals such as alkoxy, haloalkyl, etc., mean e.g.
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the Aikylresten, wherein at least one double bond or triple bond is included. Preference is given to radicals having a double bond or triple bond.
  • alkenyl also includes in particular straight-chain or branched open-chain carbon hydrogen radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds alkenyl is, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example propylene-1-ene-1, such as, for example, allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.
  • alkynyl in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond or else having one or more triple bonds and one or more double bonds such as 1,3-butatrienyl and 3-penten-1-yn-1-yl, respectively.
  • C 2 -C 6) -alkynyl is, for example, ethynyl, propargyl, 1-ethyl-prop-2-yn-1-yl, 2-butynyl,
  • 2-pentynyl or 2-hexynyl preferably propargyl, but-2-yn-1-yl, but-3-yn-1-yl or 1-ethyl-but-3-yn-1-yl.
  • cycloalkyl means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.
  • substituents also have one
  • an alkylidene group such as methylidene, are included.
  • optionally substituted cycloalkyl also become
  • polycyclic aliphatic systems such as, for example, bicyclo [.1] o-butan-1-yl, bicyclo [1 .1] -butan-2-yl, bicyclo [2.1.0] pentan-1-yl, bicyclo [2.1. 0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.2.1] hept-2-yl (norbornyl), bicyclo [2.2.2] octan-2-yl, adamantane-1 -yl and adamantan-2-yl.
  • (C3-C7) cycloalkyl means a shorthand notation for cycloalkyl having from three to seven carbon atoms corresponding to the range of C atoms.
  • substituted cycloalkyl are also spirocyclic aliphatic
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-
  • Alkylidene group such as methylidene, are included. In case of if necessary
  • alkylidene for example also in the form of (C 1 -C 10) -alkylidene, means the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond naturally only positions on the body in question, where two H atoms can be replaced by the double bond; Remains are z.
  • Cycloalkylidene means a carbocyclic radical which is bonded via a double bond.
  • stannyl stands for a further substituted radical containing a tin atom
  • “Germanyl” is analogous to a further substituted radical which is a
  • Zeroconyl represents a further substituted radical containing a zirconium atom.
  • Hafnyl represents a further substituted radical containing a hafnium atom.
  • Boryl represents a further substituted radical containing a hafnium atom.
  • Boryl is further substituted and optionally cyclic groups, each containing a boron atom.
  • Plumbanyl represents a further substituted radical containing a lead atom.
  • Haldrargyl represents a further substituted radical containing a mercury atom.
  • Alignyl represents a further substituted radical containing an aluminum atom.
  • Magnnesyl represents a further substituted radical containing a magnesium atom.
  • Zincyl represents a further substituted radical containing a zinc atom.
  • the compounds of the general formula (I) can exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
  • Stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods. The chromatographic separation can be used both on an analytical scale for
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
  • the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof Synthesis:
  • Substituted 2-amidobenzimidazoles can be prepared by known methods (compare J. Med. Chem. 2000, 43, 4084, Bioorg. Med. Chem. 2008, 16, 6965, Bioorg. Med. Chem. 2008, 16, 3955; Org Proc. Res. Develop., 2007, 11, 693; J. Med. Chem. 2009, 52, 514; J. Heterocyclic Chem. 2001, 38, 979; WO2000026192;
  • Synthetic routes are based on commercially available or easily prepared 2-amino-3-nitrobenzoic acids or 2,3-diaminobenzonitriles.
  • the optionally additionally substituted 2-amino-3-nitrobenzoic acid in question can be converted with the aid of thionyl chloride and ammonia into the corresponding 2-amino-3-nitrobenzamide, either with hydrogen in the presence of palladium on carbon in a suitable solvent or with tin ( ll) chloride is reduced to an optionally further substituted 2,3-diaminobenzamide.
  • the thus obtained 2,3-diaminobenzamide can in the following step on various
  • Reaction variants eg., condensation with a carboxylic acid, with an aldehyde or an amidoxime can be converted into the desired benzimidazole derivative.
  • the corresponding benzimidazole can also be constructed by condensation of a 2,3-diaminobenzoic acid with a carboxylic acid or by N-acylation of a 2-amino-3-nitrobenzoic acid ester and subsequent reduction with hydrogen in the presence of palladium on carbon and the carboxyl function in the final step in the desired amide be transferred.
  • a further reaction route for the synthesis of the compounds according to the invention is the condensation of an optionally substituted 2,3-diaminobenzonitrile with a corresponding carboxylic acid and the subsequent reaction with a hydroxide base (eg.
  • Benzimidazole N-atom succeeds by deprotonation with a suitable base, for.
  • a suitable base for example, sodium hydride in an aprotic solvent, and subsequent reaction with a suitable electrophile, for example an acyl chloride, an alkyl halide or a chloroformate.
  • the amide group of the fluoroalkyl-substituted 2-amidobenzimidazoles prepared according to the invention can also be converted into the corresponding thioamide with the aid of 2,4-bis- (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4-disulfide or in a two-step synthesis by reaction with tert-butyl hypochlorite and AIBN in an aprotic solvent (e.g. B.
  • aprotic solvent e.g. B.
  • Substituted 2-amidobenzoxazoles can likewise be prepared by known processes (compare, Bioorg.Med.Chem., 2006, 14, 6106, WO2010083220;
  • optionally further substituted 2-amino-3-hydroxybenzoeklathylester is thereby converted with a suitable anhydride in THF or by condensation with a suitable carboxylic acid in the corresponding optionally substituted benzoxazole.
  • the ethyl ester is cleaved with the aid of a suitable hydroxide base (for example LiOH, KOH or NaOH) to give the optionally further substituted benzoxazolylcarboxylic acid, which may then be further introduced into the product according to the invention by using thionyl chloride and subsequent reaction of the acid chloride with ammonia substituted 2-amidobenzoxazole is transferred.
  • a suitable hydroxide base for example LiOH, KOH or NaOH
  • Substituted 2-amidobenzothiazoles can likewise be prepared analogously to the synthesis routes described above by processes known from the literature (compare Bioorg.Med.Chem. 2006, 14, 6106, WO2010083199).
  • further substituted 2-nitro-3-chlorobenzoic acids are first converted into the corresponding 2-amino-3-hydrothiobenzoic acids with the aid of sodium sulfide hydrate in a suitable polar protic solvent (eg methanol or water) (Scheme 4).
  • the relevant optionally further substituted 2-amino-3-hydrothiobenzoic acid is in this case with a suitable anhydride in THF or by direct condensation with a suitable carboxylic acid in the corresponding optionally further substituted benzothiazolylcarboxylic acid, which is subsequently purified by use of thionyl chloride or another suitable
  • Chlorination reagent eg., Oxalylchlorid
  • subsequent reaction of the acid chloride with ammonia to the optionally further substituted 2-amidobenzothiazole according to the invention is reacted.
  • the radicals R 1 , R 3 and Q mentioned in the following scheme 4 likewise have the meanings defined above.
  • Pentafluoropropionic anhydride (471 mg, 1.52 mmol) in abs. THF (2 ml) was added and the reaction mixture was kept at -78 ° C for 30 minutes and then for 1 hour
  • Compounds A5-1 to A5-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is chlorine, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 is the respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A5-1 to A5-1000).
  • Residue definitions (Nos 1 to 1000, corresponding to compounds A10-1 to A10-1000).
  • A1 1 Compounds A1 1 -1 to A1 1 -1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is ethynyl, X is NR 4 and Q, W, Z 1 , Z 2 and R 4 for the respective individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A1 1 -1 to A1 1 -1000).
  • Residue definitions (Nos 1 to 1000, corresponding to compounds A14-1 to A14-1000).
  • A15. Compounds A15-1 to A15-1000 of the general formula (I) wherein R 1 and R 2 are hydrogen, R 3 is fluorine, X is NR 4 and Q, W, Z ⁇ Z 2 and R 4 for the Respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A15-1 to A15-1000).
  • A16 Compounds A15-1 to A15-1000 of the general formula (I) wherein R 1 and R 2 are hydrogen, R 3 is fluorine, X is NR 4 and Q, W, Z ⁇ Z 2 and R 4 for the Respective individual compounds correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A15-1 to A15-1000).
  • Compounds A17-1 to A17-1000 of the general formula (I) wherein R 1 and R 2 are hydrogen, R 3 is bromine, X is NR 4 and Q, W, Z ⁇ Z 2 and R 4 for the corresponding individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A17-1 to A17-1000).
  • Residue definitions (Nos 1 to 1000, corresponding to compounds A18-1 to A18-1000).
  • Residue definitions (nos 1 to 1000, corresponding to compounds A30-1 to A30-1000).
  • Residue definitions (Nos 1 to 1000, corresponding to compounds A32-1 to A32-1000).
  • A33 Compounds A33-1 to A33-1000 of the general formula (I) wherein R 1 and R 3 are hydrogen, R 2 is ethenyl, X is NR 4 and Q, W, Z ⁇ Z 2 and R 4 for the corresponding individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A33-1 to A33-1000).
  • A34 Compounds A34-1 to A 34-1000 of the general formula (I) in which R 1 and R 3 are hydrogen, R 2 is cyclobutyl, X is NR 4 and Q, W, Z 1 , Z 2 and
  • R 4 for the respective individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 1000, corresponding to compounds A34-1 to A34-1000).
  • Residue definitions (nos 1 to 1000, corresponding to compounds A36-1 to A36-1000).
  • the present invention thus provides the use of at least one compound selected from the group consisting of substituted
  • abiotic stress factors preferably drought stress
  • a further subject of the present invention is a spray solution for the treatment of plants, comprising an amount of at least one effective for increasing the resistance of plants to abiotic stress factors
  • heat, drought, cold and drought stress stress caused by drought and / or water deficiency
  • osmotic stress waterlogging
  • increased soil salt content increased exposure to minerals, ozone conditions
  • High light conditions limited availability of nitrogen nutrients, limited availability of phosphorus nutrients.
  • Substituted 2-Amidobenzimidazole, 2-Amidobenzoxazole and 2-amidobenzothiazoles of the general formula (!), are applied by a spray application to appropriate plants or plant parts to be treated.
  • the use according to the invention of the compounds of the general formula (I) or salts thereof is preferably carried out with a dosage of between 0.00005 and 3 kg / ha, more preferably between 0.0001 and 2 kg / ha, particularly preferably between 0.0005 and 1 kg / ha, more preferably between 0.001 and 0.25 kg / ha.
  • the admixing of abscisic acid is preferably carried out in one dosage between 0.0001 and 3 kg / ha, more preferably between 0.001 and 2 kg / ha, particularly preferably between 0.005 and 1 kg / ha, in particular preferably between 0.006 and 0.25 kg / ha.
  • resistance or resistance to abiotic stress is understood to mean various advantages for plants. Such advantageous properties are manifested, for example, in the following improved plant characteristics: improved root growth in terms of surface area and depth, increased tailing or stocking, stronger and more productive shoots and tillers,
  • Sprout base diameter increased leaf area, higher yields of nutrients and ingredients, such as carbohydrates, fats, oils, proteins, vitamins, minerals, essential oils, dyes, fibers, better fiber quality, earlier flowering, increased number of flowers, reduced content of toxic products such as mycotoxins , reduced content of residues or unfavorable ingredients of any kind or better digestibility, improved storage stability of the crop, improved tolerance to unfavorable temperatures, improved tolerance to drought and Dryness, as well as lack of oxygen due to excess water, improved
  • nutrients and ingredients such as carbohydrates, fats, oils, proteins, vitamins, minerals, essential oils, dyes, fibers, better fiber quality, earlier flowering, increased number of flowers, reduced content of toxic products such as mycotoxins , reduced content of residues or unfavorable ingredients of any kind or better digestibility, improved storage stability of the crop, improved tolerance to unfavorable temperatures, improved tolerance to drought and Dryness, as well as lack of oxygen due to excess water, improved
  • Photosynthesis beneficial plant properties, such as
  • 2-amidobenzimidazoles according to the invention, 2-amidobenzoxazoles and 2-amidobenzothiazoles of the general formula (I) inter alia with insecticides, attractants, acaricides, fungicides, nematicides, herbicides,
  • Amidobenzothiazoles of general formula (I) with genetically modified varieties with respect to increased abiotic stress tolerance is also possible.
  • Non-limiting resistance to abiotic stress ⁇ at least one in general 3%, in particular greater than 5%
  • At least one root development generally improved by 3%, in particular greater than 5%, particularly preferably greater than 10%,
  • At least one shoot size increasing by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
  • At least one leaf area increased by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
  • a further subject of the present invention is a spray solution for the treatment of plants, comprising an amount of at least one effective for increasing the resistance of plants to abiotic stress factors
  • the spray solution may comprise other conventional ingredients, such as solvents, formulation auxiliaries, especially water.
  • Other ingredients may include agrochemical agents, which are further described below.
  • Another object of the present invention is the use of
  • potassium salts preferably chlorides, sulfates, nitrates
  • phosphoric acid salts and / or salts of phosphorous acid preferably potassium salts and ammonium salts.
  • NPK fertilizers ie fertilizers containing nitrogen, phosphorus and potassium, calcium ammonium nitrate, ie fertilizers which still contain calcium, ammonium sulphate nitrate (general formula (NH 4 ) 2 SO 4 NH 4 NO 3), ammonium phosphate and ammonium sulphate.
  • ammonium sulphate nitrate generally formula (NH 4 ) 2 SO 4 NH 4 NO 3
  • ammonium phosphate and ammonium sulphate generally known to those skilled in the art, see also, for example, Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A 10, pages 323 to 431, Verlagsgesellschaft, Weinheim, 1987.
  • the fertilizers may also contain salts of micronutrients (preferably calcium,
  • Fertilizers used according to the invention may also contain other salts such as monoammonium phosphate (MAP), diammonium phosphate (DAP), potassium sulfate,
  • fertilizers Containing potassium chloride, magnesium sulfate. Suitable amounts for the secondary nutrients or trace elements are amounts of 0.5 to 5 wt .-%, based on the total fertilizer.
  • Further possible ingredients are crop protection agents, insecticides or fungicides, growth regulators or mixtures thereof. Further explanations follow below.
  • the fertilizers can be used, for example, in the form of powders, granules, prills or compactates. However, the fertilizers can also be used in liquid form dissolved in an aqueous medium. In this case, dilute aqueous ammonia can be used as nitrogen fertilizer. Further possible ingredients for fertilizers are, for example, in Ullmann's
  • the general composition of the fertilizers which in the context of the present invention may be single-nutrient and / or complex nutrient fertilizers,
  • nitrogen, potassium or phosphorus may vary within a wide range.
  • a content of 1 to 30 wt .-% of nitrogen preferably 5 to 20 wt .-%), from 1 to 20 wt .-% potassium (preferably 3 to 15% by weight) and a content of 1 to 20% by weight of phosphorus (preferably 3 to 10% by weight) is advantageous.
  • the content of microelements is usually in the ppm range, preferably in the range of from 1 to 1000 ppm.
  • the fertilizer and one or more compounds of the general formula (I) can be administered at the same time.
  • the fertilizer and one or more compounds of the general formula (I) can be administered at the same time.
  • it is also possible first the fertilizer and then one or more compounds of the general formula (I) can be administered at the same time.
  • inventive compounds of formula (I) and the fertilizer in a time frame of less than 1 hour, preferably less than 30 minutes, more preferably less than 15 minutes.
  • the forest stock includes trees for the production of wood, pulp, paper and products made from parts of the trees.
  • crops as used herein refers to
  • Among the useful plants include z.
  • the following plant species Triticale, Durum
  • Durum wheat turf, vines, cereals, such as wheat, barley, rye, oats, rice, corn and millet
  • Beets for example sugar beets and fodder beets
  • Fruits such as pome fruit, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries and berries, eg. Strawberries, raspberries, blackberries
  • Legumes such as beans, lentils, peas and soybeans
  • Oil crops such as oilseed rape, mustard, poppy, olives, sunflowers, coconut,
  • Castor oil plants cocoa beans and peanuts; Cucurbits, for example squash, cucumbers and melons; Fiber plants, for example cotton, flax, hemp and jute; Citrus fruits, such as oranges, lemons, grapefruit and mandarins; Vegetables such as spinach, (head) salad, asparagus, cabbages, carrots, onions, tomatoes, potatoes and peppers; Laurel family, such as avocado, cinnamomum, camphor, or plants such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, vines, hops, bananas,
  • Natural rubber plants and ornamental plants such as flowers, shrubs, deciduous trees and conifers such as conifers. This list is not a limitation.
  • Particularly suitable target crops for the application of the method according to the invention are the following plants: oats, rye, triticale, durum, cotton, aubergine, turf, pome fruit, stone fruit, berry fruit, corn, wheat, barley, cucumber, tobacco, vines, rice, cereals , Pear, pepper, beans, soybeans, rape, tomato, paprika, melons, cabbage, potato and apple.
  • Examples of trees which can be improved according to the process of the invention are: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., PSatanus sp., Tilia sp., Acer sp., Tsuga sp., Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp ., Populus sp ..
  • trees which can be improved according to the method of the invention, may be mentioned: From the tree species Aesculus: A. hippocastanum, A. pariflora, A. carnea; from the tree species Platanus: P. aceriflora, P. occidentalis, P. racemosa; from the tree species Picea: P. abies; from the tree Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P.
  • albicaulis P. resinosa, P. palustris, P. taeda, P. flexilis, P. jeffregi, P. baksiana, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis, E.
  • the present invention may also be practiced on any turfgrasses, including "cool season turfgrasses” and “warm season turfgrasses.”
  • cold season turf species are blue grasses (Poa spp.), Such as “Kentucky bluegrass” (Poa pratensis L), “rough bluegrass” (Poa trivialis L), “Canada bluegrass” (Poa compressa L), “annual bluegrass” (Poa annua L), “upland bluegrass” (Poa glaucantha Gaudin), “Wood bluegrass” (Poa nemoralis L.) and “bulbous bluegrass” (Poa bulbosa L); ostrich grasses ("Bentgrass”, Agrostis spp.), Such as “creeping bentgrass” (Agrostis palustris Huds.), “Colonial bentgrass” (Agrostis Tenuis Sibth.), “velvet bentgrass” (Agrostis canina L),
  • Lolium ryegrasses, Lolium spp.
  • Examples of other "cool season turfgrasses” are “beachgrass” (Ammophila breviligulata Fern.), “smooth bromegrass” (Bromus inermis leyss.), reeds (“cattails”) such as “Timothy” (Phleum pratense L.
  • orchardgrass (Dactylis glomerata L.), "weeping alkaligrass” (Puccinellia distans (L.) Pari.) and “crested dog's-tail” (Cynosurus cristatus L.).
  • Examples of “warm season turfgrasses” are “Bermudagrass” (Cynodon spp., LC Rieh), “zoysiagrass” (Zoysia spp. Willd.), “St. Augustine grass” (Stenotaphrum secundatum Walt Kuntze), “centipedegrass” (Eremochloa ophiuroides Munrohack.), “Carpetgrass” (Axonopus affinis chase), “Bahia grass” (Paspalum notatum flügge), “Kikuyugrass” (Pennisetum clandestinum detergent, ex Chiov.), “Buffalo grass” (Buchloe daetyloids (Nutt.) Engelm.) , “Blue gramma” (Bouteloua gracilis (HBK) lag.
  • the compounds of general formula (I) according to the invention plants of each commercial or in use treated plant varieties.
  • Plant varieties are understood to be plants with new traits which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques.
  • Crop plants can therefore be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties protectable or non-protectable plant varieties.
  • the treatment method according to the invention can thus also for the treatment of genetically modified organisms (GMOs), z.
  • GMOs genetically modified organisms
  • Genetically modified plants or transgenic plants
  • heterologous gene essentially means a gene that is provided or assembled outside the plant and that when introduced into the plant
  • Cell nucleus genome, the chloroplast genome or the hypochondrial genome of the transformed plant by conferring new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by having another gene present in the plant or other genes present in the plant; downregulated or switched off (for example by means of antisense technology, co-suppression technology or RNAi technology [RNA Interference]).
  • a heterologous gene present in the genome is also referred to as a transgene.
  • a transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
  • Plants and plant varieties which are preferably treated with the compounds of the general formula (I) according to the invention include all plants which have genetic material which gives these plants particularly advantageous, useful features (regardless of whether this is achieved by breeding and / or biotechnology has been).
  • Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are resistant to one or more abiotic stress factors. To the abiotic stress factors,
  • Stress conditions can include, for example, heat, drought, cold and dry stress, osmotic stress, waterlogging, increased soil salt content, increased exposure to minerals, ozone conditions, high light conditions, limited availability of
  • Nitrogen nutrients limited availability of phosphorus nutrients or avoiding shadows.
  • Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are characterized by increased yield properties. An increased yield can in these plants z. B. on improved plant physiology, improved
  • Plant growth and improved plant development such as
  • the yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for the production of hybrid seed,
  • Root growth seed size, fruit size, pod size, pods or
  • Plants which can also be treated with the compounds of the general formula (I) according to the invention are hybrid plants which have already been used
  • Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner).
  • the hybrid seed is typically harvested from the male sterile plants and sold to propagators.
  • Pollen sterile plants can sometimes (for example in the case of corn) by Entfahnen (ie mechanical removal of male genitalia or male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome.
  • the desired product as one wants to harvest from the hybrid plants, is the seeds, it is usually beneficial to ensure that the pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility , completely restored. This can be accomplished by ensuring that the male crossbred partners possess appropriate fertility restorer genes capable of controlling pollen fertility in humans
  • Pollen sterility may be localized in the cytoplasm.
  • CMS cytoplasmic male sterility
  • Brassica species WO 92/005251, WO 95/009910, WO 98/27806, WO 05/002324, WO 06/021972 and US 6,229,072
  • genetic determinants of pollen sterility can also be found in the
  • Pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering.
  • a particularly convenient means of producing male-sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens.
  • the fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells (eg WO 91/002069).
  • Plants or plant varieties which are obtained by plant biotechnology methods, such as genetic engineering), which also with the inventive
  • herbicide-tolerant plants d. H. Plants tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.
  • Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H.
  • glyphosate-tolerant plants can Transformation of the plant with a gene encoding the enzyme 5-enolpyruvylshikimat 3-phosphate synthase (EPSPS) can be obtained.
  • EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., Science (1983), 221, 370-371), the CP4 gene of the bacterium
  • Glyphosate-tolerant plants can also be obtained by expressing a gene coding for a glyphosate oxidoreductase enzyme as described in US 5,776,760 and US 5,463,175. Glyphosate-tolerant plants may also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in, e.g. WO 02/036782, WO 03/092360, WO 05/012515 and WO 07/024782. Glyphosate-tolerant plants can also be obtained by culturing plants containing the naturally occurring mutations of the above-mentioned genes, as described, for example, in WO 01/024615 or WO
  • herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate.
  • Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition.
  • an effective detoxifying enzyme is, for example, an enzyme suitable for
  • Phosphinotricin acetyltransferase encoded such as the bar or pat protein from Streptomyces species. Plants expressing an exogenous phosphinotricin acetyltransferase are described, for example, in US 5,561,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 and US 7,112,665.
  • hydroxyphenylpyruvate dioxygenase HPPD
  • HPPD hydroxyphenylpyruvate dioxygenase
  • the hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate.
  • Plants tolerant to HPPD inhibitors may be treated with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant HPPD enzyme according to WO 96/038567, WO
  • Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 99/034008 and WO 2002/36787.
  • the tolerance of plants to HPPD inhibitors can also be improved by transforming plants, in addition to a gene which codes for an HPPD-tolerant enzyme, with a gene which codes for a prephenate dehydrogenase enzyme, as described in WO 2004 / 024928 is described.
  • ALS acetolactate synthase
  • known ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines,
  • Acetohydroxy acid synthase known
  • Sulfonylurea and imidazolinone tolerant plants are also useful in e.g. WHERE
  • Imidazolinones, sulfonylureas and / or sulfamoylcarbonyltriazolinones can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutagenesis, as for example for the soybean in US 5,084,082, for rice in WO 97/41218, for the sugar beet in US 5,773,702 and WO 99/057965, for salad in US 5,198,599 or for the sunflower in WO 2001/065922.
  • Plants or plant varieties obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
  • insect-resistant transgenic plants i. Plants that have been made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance.
  • an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof such as the insecticidal crystal proteins collected by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature (online at:
  • insecticidal parts thereof e.g. Proteins of Cry protein classes CrylAb, CrylAc, Cryl F, Cry2Ab, Cry3Ae or Cry3Bb or insecticidal parts thereof; or 2) a crystal protein from Bacillus thuringiensis or a part thereof which is present in
  • a second, different crystal protein than Bacillus thuringiensis or a part thereof insecticide such as the binary toxin consisting of the crystal proteins Cy34 and Cy35 (Moellenbeck et al., Nat. Biotechnol. (2001), 19, 668-72; Schnepf et al., Applied Environment Microb. (2006) 71, 1765-1774); or 3) an insecticidal hybrid protein comprising parts of two different insecticides of Bacillus thuringiensis crystal proteins, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g.
  • the protein Cry1A.105 produced by the corn event MON98034 WO
  • amino acids have been replaced by another amino acid to achieve higher insecticidal activity against a target insect species and / or to broaden the spectrum of the corresponding target insect species and / or due to changes in the coding DNA during cloning or Transformation were induced, such as the protein Cry3Bb1 in maize events MON863 or MON88017 or the protein Cry3A in the maize event MIR 604; or
  • VIP3Aa Proteins of protein class VIP3Aa:
  • a secreted protein from Bacillus thuringiensis or Bacillus cereus which acts in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus insecticide, such as the binary toxin consisting of the proteins VIP1A and VIP2A (WO 94/21795); or
  • an insecticidal hybrid protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or
  • insect-resistant transgenic plants in the present connection also any plant comprising a combination of genes coding for the proteins of any of the above classes 1 to 8.
  • an insect resistant plant contains more than one transgene encoding a protein of any one of the above 1 to 8 in order to extend the spectrum of the corresponding target insect species or to develop a protein
  • Plants or plant varieties obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
  • Compounds of general formula (I) are tolerant to abiotic stressors. Such plants can be caused by genetic
  • Transformation or by selection of plants containing a mutation conferring such stress resistance include the following: a. Plants which contain a transgene which have the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or
  • Nicotinate phosphoribosyltransferase nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase, as described e.g. As described in EP 04077624.7 or WO 2006/133827 or PCT / EP07 / 002433.
  • Plants or plant varieties obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
  • Compounds of general formula (I) may have an altered amount, quality and / or shelf life of the harvested product and / or altered properties of certain components of the harvested product, such as:
  • Viscosity behavior the gel strength, the starch grain size and / or
  • Wildtype plants are modified without genetic modification. Examples are plants which produce polyfructose, in particular of the inulin and levan type, as described in EP 0663956, WO 96/001904, Wo 96/021023, WO 98/039460 and WO 99/024593, plants which are alpha-1 To produce 4-glucans, as in WO
  • Plants or plant varieties obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
  • plants of general formula (I) can be treated are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; These include: a) plants, such as cotton plants, which have an altered form of
  • cellulose synthase genes Contain cellulose synthase genes, as described in WO 98/000549, b) plants, such as cotton plants, which contain an altered form of rsw2 or rsw3-homologous nucleic acids, as described in WO 2004/05329; c) plants such as cotton plants with an increased expression of the
  • Sucrose phosphate synthase as described in WO 2001/017333; d) plants such as cotton plants with an increased expression of
  • Sucrose synthase as described in WO 02/45485; e) plants such as cotton plants in which the timing of the passage control of the Plasmodesmen is changed at the base of the fiber cell, z. B. by
  • Plants or plant varieties obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
  • Compounds of general formula (I) can be treated are plants such as rapeseed or related Brassica plants with altered properties of
  • Oil composition Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; These include: a) plants such as rape plants that produce high oleic oil, as described, for example, in US 5,969,169, US 5,840,946 or US 6,323,392 or US 6,063,947; b) plants such as oilseed rape plants which produce low linolenic acid oil, as described in US 6,270,828, US 6,169,190 or US 5,965,755. c) plants such as rape plants, which produce oil with a low saturated fatty acid content, as z. As described in US 5,434,283. Particularly useful transgenic plants with the inventive
  • Compounds of general formula (I) may be treated as plants containing transformation events, or a combination of transformation events, for example as listed in the files of various national or regional authorities.
  • Exemplary plants having one or more genes encoding one or more toxins are the transgenic plants available under the following tradenames: YIELD GARD® (for example, corn, cotton , Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example maize), StarLink® (for example corn), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn),
  • Herbicide-tolerant crops to be mentioned include, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready®
  • Herbicide-resistant plants plants traditionally grown for herbicide tolerance
  • Clearfield® for example corn
  • the compounds of the formula (I) to be used according to the invention can be converted into customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, Active substance - impregnated natural substances, active substance-impregnated synthetic substances, fertilizers and microencapsulation in polymeric substances.
  • customary formulations such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, Active substance - impregnated natural substances, active substance-impregnated synthetic substances, fertilizers and microencapsulation in polymeric substances.
  • customary formulations such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powder
  • the present invention therefore further relates to a spray formulation for increasing the resistance of plants to abiotic stress.
  • a spray formulation is described in more detail:
  • the formulations for spray application are prepared in a known manner, e.g. by mixing the compounds of the formula (I) to be used according to the invention with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • Other conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives,
  • Gibberellins and also water may also be used if necessary.
  • the preparation of the formulations is carried out either in suitable systems or before or during use.
  • Excipients which can be used are those which are suitable for imparting special properties to the composition itself or to preparations derived therefrom (for example spray mixtures), such as certain technical properties and / or special biological properties.
  • spray mixtures for example spray mixtures
  • typical aids are:
  • Hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • ketones such as acetone, cyclohexanone
  • esters including fats and oils
  • Poly ethers simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide).
  • organic solvents can also be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Suitable wetting agents which may be present in the formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are alkylnaphthalene sulfonates such as diisopropyl or diisobutylnaphthalene sulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds.
  • Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which can be used in the formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds Be contained substances. Preference is given to using silicone defoamers and magnesium stearate.
  • Formulations all substances that can be used for such purposes in agrochemical agents be present. Examples include dichlorophen and benzyl alcohol hemiformal.
  • Suitable secondary thickeners which may be present in the formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions.
  • suitable are cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
  • Further additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also micronutrients), such as salts of iron, manganese, boron , Copper, cobalt, molybdenum and zinc, stabilizers such as low-temperature stabilizers, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents.
  • nutrients also micronutrients
  • stabilizers such as low-temperature stabilizers, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents.
  • the formulations generally contain between 0.01 and 98% by weight, preferably between 0.5 and 90%, of the compound of general formula (I).
  • the compounds of general formula (I) according to the invention can be prepared in commercial formulations and in the formulations prepared from these formulations in admixture with other active substances such as insecticides,
  • Attractants sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or
  • the described positive effect of the compounds of the formula (I) on the plant's own defenses can be assisted by additional treatment with insecticidal, fungicidal or bactericidal active substances.
  • Preferred times for the application of the compounds of the general formula (I) to be used according to the invention or their salts for increasing the resistance to abiotic stress are soil, parent and / or
  • the active compounds of the general formula (I) or salts thereof to be used according to the invention can generally also be used in their commercial form
  • F1 inhibitors of nucleic acid synthesis e.g. Benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimo S, ethirimol, furaiaxyl, hymexazole, metalaxyl, metalaxyl-M, ofurace, oxadixyl, oxolinic acid;
  • F2 inhibitors of mitosis and cell division, e.g. Benomyl, carbendazim, diethofencarb, fuberidazole, fluopicolide, pencycuron, thiabendazole, thiophanate-methyl, zoxamide and chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1, 2 , 4] triazolo [1,5-ajpyrimidine;
  • Benomyl carbendazim
  • diethofencarb fuberidazole
  • fluopicolide fluopicolide
  • pencycuron thiabendazole
  • thiophanate-methyl zoxamide
  • Cyazofamide dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoximethyl, metominostrobin, orysastrobin, pyraclostrobin, pyribencarb,
  • F6 inhibitors of ATP production e.g. Fentin acetate, fentin chloride, fentin hydroxide, silthiofam
  • inhibitors of amino acid and protein biosynthesis e.g. Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim,
  • F10) inhibitors of ergosterol biosynthesis eg. Fenhexamid, azaconazole, bitertanol, bromuconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, penconazole, Propiconazole, Prothioconazole, Simeconazole, Spiroxamine, Tebuconazole, Triadimefon, Triadimenol, Triticonazole, Uniconazole, Voriconazole, Imazalil,
  • F1 1) inhibitors of cell wall synthesis, e.g. Benthiavalicarb, Bialaphos,
  • F12 inhibitors of melanin biosynthesis, e.g. Capropamide, diclocymet, fenoxanil, phtalid, pyroquilone, tricyclazole F13) resistance induction, e.g. Acibenzolar-S-methyl, probenazole, tiadinil
  • Unknown mechanism e.g. Amibromdole, benthiazole, bethoxazine,
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g.
  • Organophosphates e.g. Acephates, azamethiphos, azinphos (-methyl, -ethyl),
  • Dicrotophos dimethoates, dimethylvinphos, disulphoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthione, fosthiazate, heptenophos, isofenphos, isopropyl O- (methoxyaminothio-phosphoryl) salicylate, isoxathione, malathion, mec-carbam, methamidophos, ethidathione, Mevinphos, Monocrotophos, Naled,
  • Phosalone Phosmet, Phosphamidone, Phoxim, Pirimiphos (-methyl), Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep,
  • Tebupirimfos Temephos, Terbufos, Tetrachlorvinphos, Thiometone, Triazophos, Triclorfon and Vamidothion.
  • GABA-controlled chloride channel antagonists such as organo-chiorines, e.g. Chlordane and endosulfan (alpha); or fiproles (phenylpyrazoles), e.g. Ethiprole, Fipronil, Pyrafluprole and Pyriprole.
  • organo-chiorines e.g. Chlordane and endosulfan (alpha)
  • fiproles phenylpyrazoles
  • Ethiprole e.g. Ethiprole, Fipronil, Pyrafluprole and Pyriprole.
  • Sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids, e.g. Acrinathrin, allethrin (d-cis-trans, d-trans), bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin (beta-), cyhalothrin (gamma, lambda), cypermethrin (alpha-, beta , theta, zeta), cychenothrin [(1R) -fra / 7s isomers], deltamethrin, dimefluthrin, empenthrin [(EZ) (1R) isomers], esfenvalerates, etofenprox, fenpropathrin, fenvalerates , Flucythrinates, flumethrin, fluval
  • nicotinergic acetylcholine receptor agonists such as neonicotinoids, eg, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; or nicotine.
  • aceiylcholine receptor moduators agonists
  • spinosyns eg spinetoram
  • spinosad thiamethoxam
  • chloride channel activators such as avermectins / milbemycins, eg
  • Juvenile hormone analogs e.g. Hydroprene, kinoprene, methoprene; or
  • Active ingredients with unknown or non-specific mechanisms of action such as fumigants, e.g. Methyl bromide and other alkyl halides; or chloropicrin; sulfuryl fluoride; Borax; Tartar emetic.
  • Selective feeding inhibitors e.g. pymetrozine; or flonicamide.
  • mite growth inhibitors e.g. Clofentezine, diflovidazine, hexythiazox, etoxazole.
  • inhibitors of oxidative phosphorylation such as diafenthiuron; or organotin compounds, e.g. Azocyclotine, cyhexatin, fenbutatin oxide; or propargite; Tetrad ifon.
  • ATP disruptors such as diafenthiuron
  • organotin compounds e.g. Azocyclotine, cyhexatin, fenbutatin oxide; or propargite; Tetrad ifon.
  • Decoupling of oxidative phosphorylation by interruption of the H proton gradient such as chlorfenapyr and DNOC.
  • nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap (hydrochloride), thiocyclam, and thiosultap (-sodium).
  • inhibitors of chitin biosynthesis, type 0, such as benzoylureas, eg bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron,
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Moisture-disrupting agents such as cyromazines.
  • ecdysone agonists / disruptors such as diacylhydrazines, e.g.
  • Chromafenozide Halofenozide, Methoxyfenozide and Tebufenozide.
  • Octopaminergic agonists such as amitraz.
  • I20 complex I l electron transport inhibitors such as, for example, hydramethylnone; acequinocyl; Fluacrypyrim.
  • Complex I electron transport inhibitors for example from the group of the METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad; or Rotenone (Derris).
  • METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad; or Rotenone (Derris).
  • voltage dependent sodium channel blockers e.g. indoxacarb; Metaflumizone.
  • inhibitors of acetyl-CoA carboxylase such as tetronic acid derivatives, e.g. Spirodiclofen and spiromesifen; or tetramic acid derivatives, e.g. Spirotetramat.
  • complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine, zinc phosphide; or cyanide.
  • phosphines e.g. Aluminum phosphide, calcium phosphide, phosphine, zinc phosphide; or cyanide.
  • Complex I l electron transport inhibitors such as cyenopyrafen.
  • ryanodine receptor effectors such as, for example, diamides, eg flubendiamide, chiorantraniipyrole (rynaxypyr), cyantraniliproie (cyazypyr) and 3-bromo-N- ⁇ 2-bromo-4-chloro-6 - [(1-cyclopropylethyl) carbamoyl] phenyl ⁇ -1 - (3-chloropyridin-2-yl) -1H-pyrazole-5- carboxamide (known from WO2005 / 077934) or methyl 2- [3,5-dibromo-2 - ( ⁇ [3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl ⁇ amino) benzoyl] -1, 2-dimethylhydrazinecarboxylate (known from WO2007 / 043677).
  • Other drugs with unknown mechanism of action such as
  • Triazole-5-amines (known from WO 2006/043635), [(3S, 4aR, 12R, 12aS, 12 ⁇ S) -3- [(cyclopropylcarbonyl) oxy] -6,12-dihydroxy-4,12b-dimethyl-11 -oxo-9- (pyridin-3-yl) -1,4,4,4a, 5,6,6a, 12,12a, 12 ⁇ -decahydro-2H, 1: 1 H-benzo [f] pyrano [4,3 -b] chromen-4-yl] methylcyclopropanecarboxylate (known from WO 2006/129714), 2-cyano-3- (difluoromethoxy) -N, N-dimethylbenzenesulfonamide (known from WO2006 / 056433), 2-cyano-3- (difluoromethoxy ) -N-methylbenzenesulfonamide (known from WO2006 / 100288), 2-cyano-3- (d
  • Safeners are preferably selected from the group consisting of:
  • riA is a natural number of 0 to 5, preferably 0 to 3;
  • RA 1 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C 1 -C 4 ) haloalkyl;
  • WA is an unsubstituted or substituted divalent heterocyclic radical selected from the group consisting of the monounsaturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group N and O, where at least one N atom and at most one O atom are present in the ring, preferably one Remainder of the group (W A 1 ) to (WA 4 ),
  • rriA is 0 or 1
  • RA 2 is ORA 3 , SRA 3 or NRA 3 RA 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is bonded via the N- Atom is connected to the carbonyl group in (S1) and is unsubstituted or substituted by radicals from the group (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy or optionally substituted phenyl, preferably a radical of the formula ORA 3 , NHRA 4 or N (CH 3) 2, in particular of the formula ORA 3 ;
  • RA 3 is hydrogen or an unsubstituted or substituted aliphatic
  • Carbon hydrogen radical preferably having a total of 1 to 18 carbon atoms
  • RA 4 is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkoxy or substituted or
  • RA 5 is H, (C 1 -C 8 ) alkyl, (C 1 -C 8 ) haloalkyl, (C 1 -C 4 ) alkoxy (C 1 -C 8 ) alkyl, cyano or COORA 9 , in which R A 9 is hydrogen, (C 1 -C 8 ) alkyl, (Ci-C 8) haloalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-Ce) hydroxyalkyl, (C3-Ci2) -cycloalkyl or tri- (Ci-C 4 ) -alkyl-silyl; RA 6 , RA 7 , RA 8 are identical or different hydrogen, (C 1 -C 8 ) alkyl, (C 1 -C 8 ) haloalkyl,
  • Ci2 cycloalkyl or substituted or unsubstituted phenyl; preferably: a) compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid (S1 a ), preferably compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid, 1- ( 2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoiin-3-carboxylic acid ethyl ester (S1 -1) ("mefenpyr-diethyl”), and related compounds, as described in WO-A -91 / 07874 are described;
  • S1 C 1,5-diphenylpyrazole-3-carboxylic acid
  • S1 C preferably compounds such as 1- (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylic acid ethyl ester (S1 -5), 1- (2 -Chlorphenyi) -5-phenylpyrazole-3-carboxylic acid methyl ester (S1 -6) and related compounds as described for example in EP-A-268554;
  • RB 1 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, nitro or (C 1 -C 4 ) haloalkyl;
  • ne is a natural number of 0 to 5, preferably 0 to 3;
  • RB 2 is OR B 3 , SRB 3 or NR B 3 RB 4 or a saturated one
  • RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 8 C atoms;
  • RB 4 is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkoxy or substituted or
  • TB is a (Ci or C2) alkanediyl chain which is unsubstituted or substituted by one or two (Ci-C) alkyl radicals or by [(d-C3) alkoxy] carbonyl; preferably:
  • Rc 1 is (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl,
  • (C3-C) cycloalkyl preferably dichloromethyl
  • Rc 2, rc 3 are identical or different hydrogen, (Ci-C 4) alkyl, (C2-C4) alkenyl, (C 2 -C) alkynyl, (Ci-C 4) haloalkyl, (C 2 -C 4) haloalkenyl, (Ci-C 4) alkylcarbamoyl (Ci-C) alkyl, (C 2 -C 4) Alkenylcarbamoyl- (Ci-C) alkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, dioxolanyl (Ci-C) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine,
  • Pre-emergence safeners are applied, such. B.
  • X D is CH or N
  • RD 1 is CO-NR D 5 RD 6 or NHCO-RD 7 ;
  • RD 2 is halogen, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy, nitro, (Ci-C 4) alkyl,
  • RD 3 is hydrogen, (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl;
  • R D 4 is halogen, nitro, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy,
  • RD 5 is hydrogen, (Ci-C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (Cs-CeJCycloalkenyl, phenyl or 3-6 heterocyclyl-containing hetero-hetero atoms from the group consisting of nitrogen, oxygen and sulfur, where the last seven radicals are represented by VD substituents from the group consisting of halogen, (C 1 -C 6 -alkoxy, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 2 ) -alkylsulfinyl, ( Ci-C 2 ) alkylsulfonyl, (C 3 -C 6 ) cycloalkyl, (Ci- C 4 ) alkoxycarbonyl, (Ci-C 4 ) alkylcarbonyl and phenyl and in
  • RD 7 is hydrogen, (Ci-C 4) alkylamino, di (Ci-C 4) alkylamino, (Ci-C 6) alkyl,
  • (C3-C6) cycloalkyl where the 2 last-mentioned radicals by VD substituents selected from the group consisting of halogen, (Ci-C 4 ) alkoxy, (d-C6) haloalkoxy and (Ci-C 4 ) alkylthio and in the case of cyclic radicals also (Ci -C 4) alkyl and (Ci-C4) haloalkyl groups;
  • n D 0, 1 or 2;
  • VD is 0, 1, 2 or 3; Of these, preference is given to compounds of the N-acylsulfonamide type, for example of the following formula (S4 a ), which are, for example, B. are known from WO-A-97/45016
  • RD 7 (Ci-C6) alkyl, (C3-C-6) cycloalkyl, wherein the latter two radicals by VD substituents selected from the group consisting of halogen, (Ci-C 4 ) alkoxy, (Ci-Ce) haloalkoxy and (d-C 4 ) alkylthio and in the case of cyclic radicals are also (Ci-C4) alkyl and (Ci-C 4 ) haloalkyl substituted;
  • RD 4 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3;
  • ITID 1 or 2

Landscapes

  • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Utilisation de 2-amidobenzimidazoles, de 2-amidobenzoxazoles et de 2-amidobenzothiazoles substitués de formule générale (I) ou de leurs sels, les groupes de la formule générale (I) ayant les définitions figurant dans la description, pour augmenter la tolérance des plantes au stress abiotique, renforcer la croissance des plantes et/ou augmenter le rendement des plantes, et procédés spéciaux pour produire les composés susmentionnés.
EP13758839.8A 2012-09-05 2013-09-03 Utilisation de 2-amidobenzimidazoles, de 2-amidobenzoxazoles et de 2-amidobenzothiazoles substitués ou de leurs sels comme principes actifs contre le stress abiotique des plantes Withdrawn EP2892345A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP13758839.8A EP2892345A1 (fr) 2012-09-05 2013-09-03 Utilisation de 2-amidobenzimidazoles, de 2-amidobenzoxazoles et de 2-amidobenzothiazoles substitués ou de leurs sels comme principes actifs contre le stress abiotique des plantes

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP12183149 2012-09-05
EP13758839.8A EP2892345A1 (fr) 2012-09-05 2013-09-03 Utilisation de 2-amidobenzimidazoles, de 2-amidobenzoxazoles et de 2-amidobenzothiazoles substitués ou de leurs sels comme principes actifs contre le stress abiotique des plantes
PCT/EP2013/068167 WO2014037340A1 (fr) 2012-09-05 2013-09-03 Utilisation de 2-amidobenzimidazoles, de 2-amidobenzoxazoles et de 2-amidobenzothiazoles substitués ou de leurs sels comme principes actifs contre le stress abiotique des plantes

Publications (1)

Publication Number Publication Date
EP2892345A1 true EP2892345A1 (fr) 2015-07-15

Family

ID=47044766

Family Applications (1)

Application Number Title Priority Date Filing Date
EP13758839.8A Withdrawn EP2892345A1 (fr) 2012-09-05 2013-09-03 Utilisation de 2-amidobenzimidazoles, de 2-amidobenzoxazoles et de 2-amidobenzothiazoles substitués ou de leurs sels comme principes actifs contre le stress abiotique des plantes

Country Status (9)

Country Link
US (1) US20150216168A1 (fr)
EP (1) EP2892345A1 (fr)
JP (1) JP2015532650A (fr)
CN (1) CN104780764A (fr)
AU (1) AU2013311826A1 (fr)
BR (1) BR112015004858A2 (fr)
CA (1) CA2883574A1 (fr)
EA (1) EA201590482A1 (fr)
WO (1) WO2014037340A1 (fr)

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201223265D0 (en) * 2012-12-21 2013-02-06 Selvita Sa Novel benzimidazole derivatives as kinase inhibitors
US9662311B2 (en) 2013-06-21 2017-05-30 Zenith Epigenetics Ltd. Substituted bicyclic compounds as bromodomain inhibitors
BR112015031073B1 (pt) * 2013-06-21 2022-11-29 Zenith Epigenetics Ltd Compostos inibidores bicíclicos de bromodomínio e composição farmacêutica contendo os referidos compostos
CN105593224B (zh) 2013-07-31 2021-05-25 恒元生物医药科技(苏州)有限公司 作为溴结构域抑制剂的新型喹唑啉酮类化合物
TWI652014B (zh) * 2013-09-13 2019-03-01 美商艾佛艾姆希公司 雜環取代之雙環唑殺蟲劑
GB201316602D0 (en) * 2013-09-18 2013-10-30 Redx Pharma Ltd Agricultral chemicals
EP3424909A1 (fr) * 2014-01-05 2019-01-09 Washington University Un inhibiteur de la poly (adp-ribose) polymérase-1 (parp-1) et ses utilisations
CN104926793B (zh) * 2014-03-21 2017-05-24 成都海创药业有限公司 一种治疗肿瘤的化合物及其用途
CN106715428B (zh) * 2014-09-16 2020-07-07 先正达参股股份有限公司 具有含硫取代基的杀有害生物活性四环衍生物
EP3215509B1 (fr) 2014-11-06 2020-02-26 Lysosomal Therapeutics Inc. Pyrrolo[1,2-a]pyrimidines substituées et leur utilisation dans le traitement de troubles médicaux
WO2016073889A1 (fr) 2014-11-06 2016-05-12 Lysosomal Therapeutics Inc. Imidazo[1,5-a]pyrimidines substituées et leur utilisation dans le traitement de troubles médicaux
CN107001379B (zh) 2014-11-06 2022-11-01 Bial研发投资股份有限公司 取代的吡唑并[1,5-a]嘧啶以及它们在治疗医学障碍中的用途
US10710992B2 (en) 2014-12-01 2020-07-14 Zenith Epigenetics Ltd. Substituted pyridinones as bromodomain inhibitors
WO2016092375A1 (fr) 2014-12-11 2016-06-16 Zenith Epigenetics Corp. Hétérocycles substitués à titre d'inhibiteurs de bromodomaines
US10231953B2 (en) 2014-12-17 2019-03-19 Zenith Epigenetics Ltd. Inhibitors of bromodomains
CN112679467B (zh) * 2015-03-11 2024-11-01 Fmc公司 杂环取代的二环唑杀有害生物剂
TW201639811A (zh) 2015-03-13 2016-11-16 佛瑪治療公司 作為ＨＤＡＣ８抑制劑之α－桂皮醯胺化合物與組成物
EP3440080A4 (fr) 2016-04-06 2020-01-22 Lysosomal Therapeutics Inc. Composés de pyrazolo[1,5-a]pyrimidinyl carboxamide et leur utilisation dans le traitement de troubles médicaux
JP7034935B2 (ja) 2016-04-06 2022-03-14 リソソーマル・セラピューティクス・インコーポレイテッド ピロロ［１，２－ａ］ピリミジニルカルボキサミド化合物および医学的障害の処置におけるその使用
EP3440083A4 (fr) 2016-04-06 2019-09-18 Lysosomal Therapeutics Inc. Composés imidazo [1,5-a]pyrimidinyl carboxamide et leur utilisation dans le traitement de troubles médicaux
US11345698B2 (en) 2016-05-05 2022-05-31 Bial—R&D Investments, S.A. Substituted imidazo[1,2-a]pyridines, substituted imidazo[1,2-a]pyrazines, related compounds, and their use in the treatment of medical disorders
BR112018072552A8 (pt) 2016-05-05 2023-03-14 Lysosomal Therapeutics Inc Compostos de imidazo [1,2-b]piridazinas e imidazo [1,5-b] piridazinas substituídas, composição farmacêutica que os compreende e seu uso no tratamento de distúrbios médicos
GB201617339D0 (en) 2016-10-12 2016-11-23 Lytix Biopharma As Therapeutic compounds
WO2018084141A1 (fr) * 2016-11-01 2018-05-11 日本農薬株式会社 Composé n-alkylsulfonylindoline, insecticide agricole et horticole le comprenant et son procédé d'utilisation
WO2018115984A1 (fr) 2016-12-19 2018-06-28 Cellix Bio Private Limited Compositions et méthodes pour le traitement d'une inflammation
JP2020128340A (ja) * 2017-04-27 2020-08-27 日本農薬株式会社 ５員環の含窒素複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法
WO2019048988A1 (fr) * 2017-09-08 2019-03-14 Pi Industries Ltd. Nouveaux composés hétérocycliques fongicides
CN109232540A (zh) * 2018-06-15 2019-01-18 深圳市坤健创新药物研究院 一种取代苯并咪唑衍生物及应用
CN108503632B (zh) * 2018-06-26 2020-07-28 北京圣永制药有限公司 一种吲哚类衍生物及其在糖尿病中的应用
MX2021001456A (es) * 2018-08-06 2021-05-27 Univ Leland Stanford Junior 2-arilbenzimidazoles como activadores de ppargc1a para tratar enfermedades neurodegenerativas.
UA127747C2 (uk) * 2018-10-23 2023-12-20 Басф Се Трициклічні пестицидні сполуки
CN110105300B (zh) * 2019-06-28 2023-04-14 福州大学 一种合成2-三氟乙基取代苯并噁唑化合物的方法
JP2022542396A (ja) * 2019-07-31 2022-10-03 ライボン・セラピューティクス・インコーポレイテッド Ｃｄ３８の阻害剤としてのヘテロ二環式アミド
JP2023022335A (ja) * 2019-11-28 2023-02-15 日本農薬株式会社 ベンゾイミダゾール化合物又はその塩類及び該化合物を含有する農園芸用殺虫殺ダニ剤並びにその使用方法
CN115135384B (zh) * 2019-11-28 2024-03-22 日本农药株式会社 苯并咪唑化合物或其盐类、和含有该化合物的农艺和园艺用杀虫杀螨剂以及其使用方法
CA3181537A1 (fr) 2020-05-06 2021-11-11 Ajax Therapeutics, Inc. 6-heteroaryloxy benzimidazoles et azabenzimidazoles en tant qu'inhibiteurs de jak2
CN111620837B (zh) * 2020-06-29 2022-02-15 郑州大学 香柏酮噻唑酰胺类化合物、及其制备方法和应用
US12115154B2 (en) 2020-12-16 2024-10-15 Srx Cardio, Llc Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9)
US12043632B2 (en) 2020-12-23 2024-07-23 Ajax Therapeutics, Inc. 6-heteroaryloxy benzimidazoles and azabenzimidazoles as JAK2 inhibitors
WO2023086320A1 (fr) 2021-11-09 2023-05-19 Ajax Therapeutics, Inc. Formes et compositions d'inhibiteurs de jak2
JP2024540292A (ja) 2021-11-09 2024-10-31 エイジャックス セラピューティクス， インコーポレイテッド Ｊａｋ２阻害剤としての６－ヘテロアリールオキシベンゾイミダゾール及びアザベンゾイミダゾール
WO2023248871A1 (fr) * 2022-06-20 2023-12-28 日本曹達株式会社 Composé hétéroaryle et agent de lutte contre les organismes nuisibles
CN115583922B (zh) * 2022-10-17 2023-09-19 黄山学院 含氟n-(3-(苯并噁唑-2-基)苯基)酰胺类化合物及其制备方法和应用
CN115477615B (zh) * 2022-10-17 2024-06-18 黄山学院 N-(3-(苯并咪唑-2-基)苯基)酰胺类化合物及其制备方法和应用

Family Cites Families (241)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1905834C3 (de) 1969-02-06 1972-11-09 Basf Ag Verfahren zur Vermeidung des Staubens und Zusammenbackens von Salzen bzw.Duengemitteln
DE2906507A1 (de) 1979-02-20 1980-08-28 Bayer Ag Mittel zur regulierung des pflanzenwachstums
DE2948024A1 (de) 1979-11-29 1981-08-27 Bayer Ag, 5090 Leverkusen 1-amino-cyclopropancarbonsaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren
MA19709A1 (fr) 1982-02-17 1983-10-01 Ciba Geigy Ag Application de derives de quinoleine a la protection des plantes cultivees .
ATE103902T1 (de) 1982-05-07 1994-04-15 Ciba Geigy Ag Verwendung von chinolinderivaten zum schuetzen von kulturpflanzen.
DE3335514A1 (de) 1983-09-30 1985-04-18 Bayer Ag, 5090 Leverkusen 1-methylamino-cyclopropan-1-carbonsaeure-derivate
JPS6087254A (ja) 1983-10-19 1985-05-16 Japan Carlit Co Ltd:The 新規尿素化合物及びそれを含有する除草剤
US5331107A (en) 1984-03-06 1994-07-19 Mgi Pharma, Inc. Herbicide resistance in plants
US5304732A (en) 1984-03-06 1994-04-19 Mgi Pharma, Inc. Herbicide resistance in plants
US4761373A (en) 1984-03-06 1988-08-02 Molecular Genetics, Inc. Herbicide resistance in plants
DE3525205A1 (de) 1984-09-11 1986-03-20 Hoechst Ag, 6230 Frankfurt Pflanzenschuetzende mittel auf basis von 1,2,4-triazolderivaten sowie neue derivate des 1,2,4-triazols
EP0191736B1 (fr) 1985-02-14 1991-07-17 Ciba-Geigy Ag Utilisation de dérivés de la quinoléine pour la protection de plantes cultivables
DE3534948A1 (de) 1985-10-01 1987-04-09 Bayer Ag Fungizide und wachstumsregulatorische mittel
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
US5123951A (en) 1986-03-31 1992-06-23 Rhone-Poulenc Nederland B.V. Synergistic plant growth regulator compositions
US5273894A (en) 1986-08-23 1993-12-28 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5276268A (en) 1986-08-23 1994-01-04 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
US5637489A (en) 1986-08-23 1997-06-10 Hoechst Aktiengesellschaft Phosphinothricin-resistance gene, and its use
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
US5378824A (en) 1986-08-26 1995-01-03 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5605011A (en) 1986-08-26 1997-02-25 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
DE3633840A1 (de) 1986-10-04 1988-04-14 Hoechst Ag Phenylpyrazolcarbonsaeurederivate, ihre herstellung und verwendung als pflanzenwachstumsregulatoren und safener
EP0268554B1 (fr) 1986-10-22 1991-12-27 Ciba-Geigy Ag Dérivés d'acide diphényl-1,5-pyrazol-3-carbonique pour la protection de plantes de culture
US5638637A (en) 1987-12-31 1997-06-17 Pioneer Hi-Bred International, Inc. Production of improved rapeseed exhibiting an enhanced oleic acid content
DE3808896A1 (de) 1988-03-17 1989-09-28 Hoechst Ag Pflanzenschuetzende mittel auf basis von pyrazolcarbonsaeurederivaten
GB8810120D0 (en) 1988-04-28 1988-06-02 Plant Genetic Systems Nv Transgenic nuclear male sterile plants
DE3817192A1 (de) 1988-05-20 1989-11-30 Hoechst Ag 1,2,4-triazolderivate enthaltende pflanzenschuetzende mittel sowie neue derivate des 1,2,4-triazols
US5084082A (en) 1988-09-22 1992-01-28 E. I. Du Pont De Nemours And Company Soybean plants with dominant selectable trait for herbicide resistance
DE58903221D1 (en) 1988-10-20 1993-02-18 Ciba Geigy Ag Sulfamoylphenylharnstoffe.
US5201931A (en) 1988-12-01 1993-04-13 Her Majesty The Queen In Right Of Canada, As Represented By The National Research Council Of Canada Abscisic acid-related plant growth regulators - germination promoters
DD277832A1 (de) 1988-12-13 1990-04-18 Forschzent Bodenfruchtbarkeit Mittel zur erhoehung der stresstoleranz von kulturpflanzen
DD277835A1 (de) 1988-12-13 1990-04-18 Forschzent Bodenfruchtbarkeit Mittel zur erhoehung der stresstoleranz von kulturpflanzen
US6013861A (en) 1989-05-26 2000-01-11 Zeneca Limited Plants and processes for obtaining them
ATE496135T1 (de) 1989-08-10 2011-02-15 Bayer Bioscience Nv Pflanzen mit modifizierten blüten
DE3939010A1 (de) 1989-11-25 1991-05-29 Hoechst Ag Isoxazoline, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschuetzende mittel
DE3939503A1 (de) 1989-11-30 1991-06-06 Hoechst Ag Neue pyrazoline zum schutz von kulturpflanzen gegenueber herbiziden
US5739082A (en) 1990-02-02 1998-04-14 Hoechst Schering Agrevo Gmbh Method of improving the yield of herbicide-resistant crop plants
US5908810A (en) 1990-02-02 1999-06-01 Hoechst Schering Agrevo Gmbh Method of improving the growth of crop plants which are resistant to glutamine synthetase inhibitors
ATE152572T1 (de) 1990-04-04 1997-05-15 Pioneer Hi Bred Int Herstellung von rapssamen mit verringertem gehalt an gesättigten fettsäuren
US5198599A (en) 1990-06-05 1993-03-30 Idaho Resarch Foundation, Inc. Sulfonylurea herbicide resistance in plants
EP0536330B1 (fr) 1990-06-25 2002-02-27 Monsanto Technology LLC Plantes tolerant le glyphosate
EP0539588A1 (fr) 1990-07-05 1993-05-05 Nippon Soda Co., Ltd. Derive d'amine
FR2667078B1 (fr) 1990-09-21 1994-09-16 Agronomique Inst Nat Rech Sequence d'adn conferant une sterilite male cytoplasmique, genome mitochondrial, mitochondrie et plante contenant cette sequence, et procede de preparation d'hybrides.
DE59108636D1 (de) 1990-12-21 1997-04-30 Hoechst Schering Agrevo Gmbh Neue 5-Chlorchinolin-8-oxyalkancarbonsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Antidots von Herbiziden
DE4103253C2 (de) 1991-02-04 2000-03-23 Aua Agrar Und Umweltanalytik G Mittel zur Erhöhung der Streßtoleranz von land- und forstwirtschaftlichen Kulturpflanzen
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
US5731180A (en) 1991-07-31 1998-03-24 American Cyanamid Company Imidazolinone resistant AHAS mutants
DE4128828A1 (de) 1991-08-30 1993-03-04 Basf Ag Ammonium- oder harnstoffhaltige duengemittel und verfahren zu ihrer herstellung
US6270828B1 (en) 1993-11-12 2001-08-07 Cargrill Incorporated Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability
TW259690B (fr) 1992-08-01 1995-10-11 Hoechst Ag
DE4227061A1 (de) 1992-08-12 1994-02-17 Inst Genbiologische Forschung DNA-Sequenzen, die in der Pflanze die Bildung von Polyfructanen (Lävanen) hervorrufen, Plasmide enthaltend diese Sequenzen sowie Verfahren zur Herstellung transgener Pflanzen
GB9218185D0 (en) 1992-08-26 1992-10-14 Ici Plc Novel plants and processes for obtaining them
DE69233352T2 (de) 1992-10-14 2004-10-07 Syngenta Ltd Pflanzen und verfahren zu ihrer herstellung
DE4237557A1 (de) 1992-11-06 1994-05-11 Bayer Ag Substituierte Benzimidazole
GB9223454D0 (en) 1992-11-09 1992-12-23 Ici Plc Novel plants and processes for obtaining them
BR9406484A (pt) 1993-03-25 1996-01-09 Ciba Geigy Ag Novas proteinas e cepas pesticidas
JP3527242B2 (ja) 1993-04-27 2004-05-17 カージル，インコーポレーテッド 食用の非水素化カノラ油
WO1995004826A1 (fr) 1993-08-09 1995-02-16 Institut Für Genbiologische Forschung Berlin Gmbh Enzymes de deramification et sequences d'adn les codant, utilisables dans la modification du degre de ramification de l'amidon amylopectinique dans des plantes
DE4330960C2 (de) 1993-09-09 2002-06-20 Aventis Cropscience Gmbh Kombination von DNA-Sequenzen, die in Pflanzenzellen und Pflanzen die Bildung hochgradig amylosehaltiger Stärke ermöglichen, Verfahren zur Herstellung dieser Pflanzen und die daraus erhaltbare modifizierte Stärke
DE4331448A1 (de) 1993-09-16 1995-03-23 Hoechst Schering Agrevo Gmbh Substituierte Isoxazoline, Verfahren zu deren Herstellung, diese enthaltende Mittel und deren Verwendung als Safener
US5866782A (en) 1993-10-01 1999-02-02 Mitsubishi Corporation Gene which determines cytoplasmic sterility and a method of producing hybrid plants using said gene
AU692791B2 (en) 1993-10-12 1998-06-18 Agrigenetics, Inc. Brassica napus variety AG019
JPH09505467A (ja) 1993-11-09 1997-06-03 イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー トランスジェニックフルクタン蓄積作物およびその生産法
GB9404485D0 (en) 1994-03-09 1994-04-20 Cancer Res Campaign Tech Benzamide analogues
WO1995026407A1 (fr) 1994-03-25 1995-10-05 National Starch And Chemical Investment Holding Corporation Procede pour produire une fecule modifiee a partir de plants de pommes de terre
ATE368118T1 (de) 1994-05-18 2007-08-15 Bayer Bioscience Gmbh Für enzyme, die die fähigkeit besitzen lineare alpha 1,4-glucane in pflanzen, pilzen und mikroorganismen zu synthesieren, kodierende dna sequenzen
US5824790A (en) 1994-06-21 1998-10-20 Zeneca Limited Modification of starch synthesis in plants
AU706849B2 (en) 1994-06-21 1999-06-24 Cerestar Usa, Inc. Novel plants and processes for obtaining them
NL1000064C1 (nl) 1994-07-08 1996-01-08 Stichting Scheikundig Onderzoe Produktie van oligosacchariden in transgene planten.
DE4441408A1 (de) 1994-11-10 1996-05-15 Inst Genbiologische Forschung DNA-Sequenzen aus Solanum tuberosum kodierend Enzyme, die an der Stärkesynthese beteiligt sind, Plasmide, Bakterien, Pflanzenzellen und transgene Pflanzen enhaltend diese Sequenzen
DE4447387A1 (de) 1994-12-22 1996-06-27 Inst Genbiologische Forschung Debranching-Enzyme aus Pflanzen und DNA-Sequenzen kodierend diese Enzyme
JP3840259B2 (ja) 1995-01-06 2006-11-01 プラント リサーチ インターナショナル ベスローテン フェンノートシャップ 炭水化物ポリマー合成酵素をコードするｄｎａ配列及びトランスジェニック植物を製造するための方法
DE19509695A1 (de) 1995-03-08 1996-09-12 Inst Genbiologische Forschung Verfahren zur Herstellung einer modifizieren Stärke in Pflanzen, sowie die aus den Pflanzen isolierbare modifizierte Stärke
US5853973A (en) 1995-04-20 1998-12-29 American Cyanamid Company Structure based designed herbicide resistant products
ES2275275T3 (es) 1995-04-20 2007-06-01 Basf Aktiengesellschaft Productos resistentes a herbicidas diseñados sobre la base de la estructura.
DK0826061T3 (da) 1995-05-05 2007-09-24 Nat Starch Chem Invest Forbedringer af eller relaterede til plantestivelsessammensætninger
FR2734842B1 (fr) 1995-06-02 1998-02-27 Rhone Poulenc Agrochimie Sequence adn d'un gene de l'hydroxy-phenyl pyruvate dioxygenase et obtention de plantes contenant un gene de l'hydroxy-phenyl pyruvate dioxygenase, tolerantes a certains herbicides
US5712107A (en) 1995-06-07 1998-01-27 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
US6284479B1 (en) 1995-06-07 2001-09-04 Pioneer Hi-Bred International, Inc. Substitutes for modified starch and latexes in paper manufacture
GB9513881D0 (en) 1995-07-07 1995-09-06 Zeneca Ltd Improved plants
FR2736926B1 (fr) 1995-07-19 1997-08-22 Rhone Poulenc Agrochimie 5-enol pyruvylshikimate-3-phosphate synthase mutee, gene codant pour cette proteine et plantes transformees contenant ce gene
EA000999B1 (ru) * 1995-08-02 2000-08-28 Ньюкастл Юниверсити Венчерз Лимитед Соединение бензимидазола
DK0851934T3 (da) 1995-09-19 2006-07-31 Bayer Bioscience Gmbh Planter, som syntetiserer en modificeret stivelse, fremgangsmåder til deres fremstilling samt modificeret stivelse
GB9524938D0 (en) 1995-12-06 1996-02-07 Zeneca Ltd Modification of starch synthesis in plants
DE19601365A1 (de) 1996-01-16 1997-07-17 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle aus Pflanzen codierend Enzyme, die an der Stärkesynthese beteiligt sind
DE19608918A1 (de) 1996-03-07 1997-09-11 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle, die neue Debranching-Enzyme aus Mais codieren
US5773704A (en) 1996-04-29 1998-06-30 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Herbicide resistant rice
DE19618125A1 (de) 1996-05-06 1997-11-13 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle, die neue Debranching-Enzyme aus Kartoffel codieren
DE19619918A1 (de) 1996-05-17 1997-11-20 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle codierend lösliche Stärkesynthasen aus Mais
DE69737448T2 (de) 1996-05-29 2007-11-15 Bayer Cropscience Ag Nukleinsäuremoleküle, die für enzyme aus weizen kodieren, welche an der stärkesynthese beteiligt sind
DE19621522A1 (de) 1996-05-29 1997-12-04 Hoechst Schering Agrevo Gmbh Neue N-Acylsulfonamide, neue Mischungen aus Herbiziden und Antidots und deren Verwendung
EP0904454A1 (fr) 1996-06-12 1999-03-31 Pioneer Hi-Bred International, Inc. Substituts de l'amidon modifie utilises dans la fabrication du papier
JP2001503607A (ja) 1996-06-12 2001-03-21 パイオニア ハイ―ブレッド インターナショナル，インコーポレイテッド 製紙における改変澱粉の代用品
JP2000512349A (ja) 1996-06-12 2000-09-19 パイオニア ハイ―ブレッド インターナショナル，インコーポレイテッド 製紙における改変澱粉の代用品
AUPO069996A0 (en) 1996-06-27 1996-07-18 Australian National University, The Manipulation of plant cellulose
US5850026A (en) 1996-07-03 1998-12-15 Cargill, Incorporated Canola oil having increased oleic acid and decreased linolenic acid content
US5773702A (en) 1996-07-17 1998-06-30 Board Of Trustees Operating Michigan State University Imidazolinone herbicide resistant sugar beet plants
DE19631764A1 (de) 1996-08-06 1998-02-12 Basf Ag Neue Nitrifikationsinhibitoren sowie die Verwendung von Polysäuren zur Behandlung von Mineraldüngemitteln die einen Nitrifikationsinhibitor enthalten
US6294504B1 (en) 1996-09-26 2001-09-25 Syngenta Crop Protection, Inc. Herbicidal composition
GB9623095D0 (en) 1996-11-05 1997-01-08 Nat Starch Chem Invest Improvements in or relating to starch content of plants
CN1114604C (zh) * 1996-11-15 2003-07-16 达尔文发现有限公司 双环芳基甲酰胺及其治疗应用
US6232529B1 (en) 1996-11-20 2001-05-15 Pioneer Hi-Bred International, Inc. Methods of producing high-oil seed by modification of starch levels
DE19652961A1 (de) 1996-12-19 1998-06-25 Hoechst Schering Agrevo Gmbh Neue 2-Fluoracrylsäurederivate, neue Mischungen aus Herbiziden und Antidots und deren Verwendung
DE19653176A1 (de) 1996-12-19 1998-06-25 Planttec Biotechnologie Gmbh Neue Nucleinsäuremoleküle aus Mais und ihre Verwendung zur Herstellung einer modifizierten Stärke
CA2193938A1 (fr) 1996-12-24 1998-06-24 David G. Charne Oleagineux du genre brassica renfermant un gene restaurateur de la fertilite ameliore encodant la sterilite male cytoplasmique ogura
US5981840A (en) 1997-01-24 1999-11-09 Pioneer Hi-Bred International, Inc. Methods for agrobacterium-mediated transformation
DE19708774A1 (de) 1997-03-04 1998-09-17 Max Planck Gesellschaft Nucleinsäuremoleküle codierend Enzyme die Fructosylpolymeraseaktivität besitzen
US6071856A (en) 1997-03-04 2000-06-06 Zeneca Limited Herbicidal compositions for acetochlor in rice
DE19709775A1 (de) 1997-03-10 1998-09-17 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle codierend Stärkephosphorylase aus Mais
DE19727410A1 (de) 1997-06-27 1999-01-07 Hoechst Schering Agrevo Gmbh 3-(5-Tetrazolylcarbonyl)-2-chinolone und diese enthaltende nutzpflanzenschützende Mittel
GB9718863D0 (en) 1997-09-06 1997-11-12 Nat Starch Chem Invest Improvements in or relating to stability of plant starches
DE19742951A1 (de) 1997-09-29 1999-04-15 Hoechst Schering Agrevo Gmbh Acylsulfamoylbenzoesäureamide, diese enthaltende nutzpflanzenschützende Mittel und Verfahren zu ihrer Herstellung
DE19749122A1 (de) 1997-11-06 1999-06-10 Max Planck Gesellschaft Nucleinsäuremoleküle codierend Enzyme, die Fructosyltransferaseaktivität besitzen
FR2770854B1 (fr) 1997-11-07 2001-11-30 Rhone Poulenc Agrochimie Sequence adn d'un gene de l'hydroxy-phenyl pyruvate dioxygenase et obtention de plantes contenant un tel gene, tolerantes aux herbicides
FR2772789B1 (fr) 1997-12-24 2000-11-24 Rhone Poulenc Agrochimie Procede de preparation enzymatique d'homogentisate
EP1068333A1 (fr) 1998-04-09 2001-01-17 E.I. Du Pont De Nemours And Company Homologues de la proteine r1 de phosphorylation de l'amidon
DE19820607A1 (de) 1998-05-08 1999-11-11 Hoechst Schering Agrevo Gmbh Nucleinsäuremoleküle codierend Enzyme aus Weizen, die an der Stärkesynthese beteiligt sind
DE19820608A1 (de) 1998-05-08 1999-11-11 Hoechst Schering Agrevo Gmbh Nucleinsäuremoleküle codierend Enzyme aus Weizen, die an der Stärkesynthese beteiligt sind
EP1078088B1 (fr) 1998-05-13 2006-07-26 Bayer BioScience GmbH Vegetaux transgeniques presentant l'activite modifiee d'un translocateur d'adp/atp plastidien
DE19821614A1 (de) 1998-05-14 1999-11-18 Hoechst Schering Agrevo Gmbh Sulfonylharnstoff-tolerante Zuckerrübenmutanten
US6635756B1 (en) 1998-06-15 2003-10-21 National Starch And Chemical Investment Holding Corporation Starch obtainable from modified plants
US6693185B2 (en) 1998-07-17 2004-02-17 Bayer Bioscience N.V. Methods and means to modulate programmed cell death in eukaryotic cells
DE19836099A1 (de) 1998-07-31 2000-02-03 Hoechst Schering Agrevo Gmbh Nukleinsäuremoleküle kodierend für eine ß-Amylase, Pflanzen, die eine modifizierte Stärke synthetisieren, Verfahren zur Herstellung der Pflanzen, ihre Verwendung sowie die modifizierte Stärke
DE19836098A1 (de) 1998-07-31 2000-02-03 Hoechst Schering Agrevo Gmbh Pflanzen, die eine modifizierte Stärke synthetisieren, Verfahren zur Herstellung der Pflanzen, ihre Verwendung sowie die modifizierte Stärke
EP1108040A2 (fr) 1998-08-25 2001-06-20 Pioneer Hi-Bred International, Inc. Acides nucleiques de glutamine vegetale: fructose-6-phosphate amidotransferase
EP1109916A1 (fr) 1998-09-02 2001-06-27 Planttec Biotechnologie GmbH Molecules d'acide nucleique codant une amylosucrase
BR9915026A (pt) 1998-10-09 2001-07-17 Planttec Biotechnologie Gmbh Móleculas de ácido nucléico codificando uma enzima ramificadora de bactérias do gênero neisseria bem como métodos para a produção de alfa-1,4 glicanos ramificados para alfa-1,6
DE19924342A1 (de) 1999-05-27 2000-11-30 Planttec Biotechnologie Gmbh Genetisch modifizierte Pflanzenzellen und Pflanzen mit erhöhter Aktivität eines Amylosucraseproteins und eines Verzweigungsenzyms
BR9915013A (pt) 1998-11-03 2001-08-07 Basf Ag Composto, uso dos mesmos, processo para preparar os mesmos, droga, e, método para detecção in vitro para inibidores parp
US6624139B1 (en) 1998-11-05 2003-09-23 Eden Bioscience Corporation Hypersensitive response elicitor-induced stress resistance
JP2002529094A (ja) 1998-11-09 2002-09-10 プランテック バイオテクノロジー ゲーエムベーハー コメ由来核酸分子および改変デンプンの生産のためのその使用
PL347684A1 (en) * 1998-11-17 2002-04-22 Basf Ag 2-phenylbenzimidazoles and 2-phenylindoles, and production and use thereof
HUP0200749A3 (en) * 1998-11-27 2003-03-28 Basf Ag Substituted benzimidazoles and their use as parp inhibitors and process for their preparation
US6531648B1 (en) 1998-12-17 2003-03-11 Syngenta Participations Ag Grain processing method and transgenic plants useful therein
DE19905069A1 (de) 1999-02-08 2000-08-10 Planttec Biotechnologie Gmbh Nucleinsäuremoleküle codierend Alternansucrase
US6323392B1 (en) 1999-03-01 2001-11-27 Pioneer Hi-Bred International, Inc. Formation of brassica napus F1 hybrid seeds which exhibit a highly elevated oleic acid content and a reduced linolenic acid content in the endogenously formed oil of the seeds
BR0010069A (pt) 1999-04-29 2002-01-22 Syngenta Ltd Polinucelotìdeo isolado, vetor, material vegetal, plantas ineiras, férteis, morfologicamente normais, plantas de milho, métodos para controlar seletivamente ervas daninhas em um campo, e para produzir vegetais que sejam substancialmente tolerantes resistentes ao herbicida glifosato, uso de polinucleotìdeo, e, métodos para selecionar material biológico transformado, e para regenerar uma planta transformada fértil para conter dna estranho
EP1173580A1 (fr) 1999-04-29 2002-01-23 Syngenta Limited Plantes resistant aux herbicides
DE19926771A1 (de) 1999-06-11 2000-12-14 Aventis Cropscience Gmbh Nukleinsäuremoleküle aus Weizen, transgene Pflanzenzellen und Pflanzen und deren Verwendung für die Herstellung modifizierter Stärke
DE19937348A1 (de) 1999-08-11 2001-02-22 Aventis Cropscience Gmbh Nukleinsäuremoleküle aus Pflanzen codierend Enzyme, die an der Stärkesynthese beteiligt sind
DE19937643A1 (de) 1999-08-12 2001-02-22 Aventis Cropscience Gmbh Transgene Zellen und Pflanzen mit veränderter Aktivität des GBSSI- und des BE-Proteins
AU7647000A (en) 1999-08-20 2001-03-19 Basf Plant Science Gmbh Increasing the polysaccharide content in plants
US6423886B1 (en) 1999-09-02 2002-07-23 Pioneer Hi-Bred International, Inc. Starch synthase polynucleotides and their use in the production of new starches
US6472588B1 (en) 1999-09-10 2002-10-29 Texas Tech University Transgenic cotton plants with altered fiber characteristics transformed with a sucrose phosphate synthase nucleic acid
GB9921830D0 (en) 1999-09-15 1999-11-17 Nat Starch Chem Invest Plants having reduced activity in two or more starch-modifying enzymes
AR025996A1 (es) 1999-10-07 2002-12-26 Valigen Us Inc Plantas no transgenicas resistentes a los herbicidas.
US6803501B2 (en) 2000-03-09 2004-10-12 Monsanto Technology, Llc Methods for making plants tolerant to glyphosate and compositions thereof using a DNA encoding an EPSPS enzyme from Eleusine indica
ES2414438T3 (es) 2000-03-09 2013-07-19 E.I. Du Pont De Nemours And Company Plantas de girasol tolerantes a las sulfonilureas
DE10021468A1 (de) 2000-05-04 2001-11-08 Basf Ag Verwendung von PARP-Inhibitoren in kosmetischen Zubereitungen
US7169970B2 (en) 2000-09-29 2007-01-30 Syngenta Limited Herbicide resistant plants
US6734340B2 (en) 2000-10-23 2004-05-11 Bayer Cropscience Gmbh Monocotyledon plant cells and plants which synthesise modified starch
AR031027A1 (es) 2000-10-23 2003-09-03 Syngenta Participations Ag Composiciones agroquimicas
FR2815969B1 (fr) 2000-10-30 2004-12-10 Aventis Cropscience Sa Plantes tolerantes aux herbicides par contournement de voie metabolique
CA2425956C (fr) 2000-10-30 2014-12-23 Maxygen, Inc. Nouveaux genes glyphosate n-acetyltransferase (gat)
EP1349446B1 (fr) 2000-12-08 2013-01-23 Commonwealth Scientific And Industrial Research Organisation Modification de l'expression genetique de la sucrose synthase dans le tissu vegetal et ses applications
WO2002079410A2 (fr) 2001-03-30 2002-10-10 Basf Plant Science Gmbh Domaines de longueur de la chaine de glucan
DE60226508D1 (de) 2001-06-12 2008-06-19 Bayer Cropscience Gmbh Transgene pflanzen die stärke mit hohem amylosegehalt herstellen
WO2003013226A2 (fr) 2001-08-09 2003-02-20 Cibus Genetics Plantes non transgeniques resistant aux herbicides
HUP0401861A2 (hu) 2001-10-17 2004-12-28 Basf Plant Science Gmbh Keményítő
DE10208132A1 (de) 2002-02-26 2003-09-11 Planttec Biotechnologie Gmbh Verfahren zur Herstellung von Maispflanzen mit erhöhtem Blattstärkegehalt und deren Verwendung zur Herstellung von Maissilage
AR039501A1 (es) 2002-04-30 2005-02-23 Verdia Inc Genes de glifosato n-acetil transferasa (gat)
GB0213715D0 (en) 2002-06-14 2002-07-24 Syngenta Ltd Chemical compounds
US20040034078A1 (en) 2002-06-14 2004-02-19 Agouron Pharmaceuticals, Inc. Benzimidazole inhibitors of poly(ADP-ribosyl) polymerase
FR2844142B1 (fr) 2002-09-11 2007-08-17 Bayer Cropscience Sa Plantes transformees a biosynthese de prenylquinones amelioree
WO2004040012A2 (fr) 2002-10-29 2004-05-13 Basf Plant Science Gmbh Compositions et procedes permettant d'identifier des plantes presentant une meilleure tolerance aux herbicides imidazolinones
US20040110443A1 (en) 2002-12-05 2004-06-10 Pelham Matthew C. Abrasive webs and methods of making the same
DK1578973T3 (da) 2002-12-19 2008-11-24 Bayer Cropscience Ag Planteceller og planter, der syntetiserer en stivelse med foröget slutviskositet
CA2517879A1 (fr) 2003-03-07 2004-09-16 Basf Plant Science Gmbh Production d'amylose amelioree dans les plantes
WO2004084631A1 (fr) 2003-03-26 2004-10-07 Bayer Cropscience Gmbh Utilisation de composés aromatiques hydroxy comme phytoprotecteurs
CA2521729C (fr) 2003-04-09 2013-12-03 Bayer Bioscience N.V. Procedes et elements destines a augmenter la tolerance de plantes par rapport a des conditions de stress
MXPA05011585A (es) 2003-04-29 2006-05-25 Pioneer Hi Bred Int Genes de glifosato-n-acetil transferasa (gat) novedosos.
TWI312272B (en) 2003-05-12 2009-07-21 Sumitomo Chemical Co Pyrimidine compound and pests controlling composition containing the same
CA2526480A1 (fr) 2003-05-22 2005-01-13 Syngenta Participations Ag Amidon modifie, ses utilisations, ses procedes de production
EP1633875B1 (fr) 2003-05-28 2012-05-02 Basf Se Plantes de ble presentant une tolerance accrue aux herbicides d'imidazolinone
EP1493328A1 (fr) 2003-07-04 2005-01-05 Institut National De La Recherche Agronomique Production des lignées B. napus double zéro restauratrices avec une bonne qualité agronomique
CN1833026A (zh) 2003-07-31 2006-09-13 东洋纺织株式会社 生产透明质酸的植物
DE10335726A1 (de) 2003-08-05 2005-03-03 Bayer Cropscience Gmbh Verwendung von Hydroxyaromaten als Safener
DE10335725A1 (de) 2003-08-05 2005-03-03 Bayer Cropscience Gmbh Safener auf Basis aromatisch-aliphatischer Carbonsäuredarivate
CN100575490C (zh) 2003-08-15 2009-12-30 联邦科学与工业研究组织 改变产纤维植物中纤维特征的方法和手段
ES2743420T3 (es) 2003-08-29 2020-02-19 Instituto Nac De Tecnologia Agropecuaria Plantas de arroz que tienen tolerancia incrementada frente a herbicidas de imidazolinona
WO2005030942A1 (fr) 2003-09-30 2005-04-07 Bayer Cropscience Gmbh Vegetaux ayant une activite reduite de l'enzyme de ramification de classe 3
EP1687416A1 (fr) 2003-09-30 2006-08-09 Bayer CropScience GmbH Plantes presentant une activite augmentee d'une enzyme de ramification de classe 3
UA79404C2 (en) 2003-10-02 2007-06-11 Basf Ag 2-cyanobenzenesulfonamide for controlling pests
GB0329744D0 (en) 2003-12-23 2004-01-28 Koninkl Philips Electronics Nv A beverage maker incorporating multiple beverage collection chambers
WO2005077934A1 (fr) 2004-02-18 2005-08-25 Ishihara Sangyo Kaisha, Ltd. Anthranilamides, procédé pour la production de ceux-ci et agents antiparasitaires contenant ceux-ci
AR048026A1 (es) 2004-03-05 2006-03-22 Bayer Cropscience Gmbh Procedimientos para la identificacion de proteinas con actividad enzimatica fosforiladora de almidon
ATE541042T1 (de) 2004-03-05 2012-01-15 Bayer Cropscience Ag Pflanzen mit reduzierter aktivität des stärkephosphorylierenden enzyms phosphoglucan- wasser-dikinase
ZA200607637B (en) 2004-03-05 2008-05-28 Nissan Chemical Ind Ltd Isoxazoline-substituted benzamide compound and noxious organism control agent
AR048024A1 (es) 2004-03-05 2006-03-22 Bayer Cropscience Gmbh Plantas con actividad aumentada de distintas enzimas fosforilantes del almidon
AR048025A1 (es) 2004-03-05 2006-03-22 Bayer Cropscience Gmbh Plantas con actividad aumentada de una enzima fosforilante del almidon
US7432082B2 (en) 2004-03-22 2008-10-07 Basf Ag Methods and compositions for analyzing AHASL genes
DE102004023332A1 (de) 2004-05-12 2006-01-19 Bayer Cropscience Gmbh Chinoxalin-2-on-derivate, diese enthaltende nutzpflanzenschützende Mittel und Verfahren zu ihrer Herstellung und deren Verwendung
WO2006007373A2 (fr) 2004-06-16 2006-01-19 Basf Plant Science Gmbh Polynucleotides codant des proteines ahasl matures aux fins de creation de vegetaux tolerants a l'imidazolinone
DE102004029763A1 (de) 2004-06-21 2006-01-05 Bayer Cropscience Gmbh Pflanzen, die Amylopektin-Stärke mit neuen Eigenschaften herstellen
BRPI0513981A (pt) 2004-07-30 2008-05-20 Basf Agrochemical Products Bv planta, semente, métodos para controlar ervas daninhas na vizinhança de uma planta de girassol e de uma planta transformada, para aumentar a atividade de ahas em uma planta, para produzir uma planta resistente a herbicida, para intensificar a toleráncia a herbicida em uma planta tolerante a herbicida, para selecionar uma célula de planta trasnformada, para aumentar a resistência a herbicida de uma planta, e para combater vegetação indesejável, molécula de polinucleotìdeo isolada, cassete de expressão, célula hospedeira de não-humano, vetor de transformação, célula de planta transformada, e, polipeptìdeo isolado
BRPI0514047A (pt) 2004-08-04 2008-05-27 Basf Plant Science Gmbh polinucleotìdeo isolado, vetor de expressão de planta, polipeptìdeo isolado, célula de planta transgênica, métodos para realçar a atividade da ahas em uma planta, para controlar ervas daninhas na vizinhança de uma planta, e para produzir uma planta transgênica tendo atividade da ahas aumentada, planta transgênica, e, polipeptìdeo de fusão
DK1786908T3 (da) 2004-08-18 2010-06-07 Bayer Cropscience Ag Planter med forøget plastidisk aktivitet af stivelsesphosphorylerende R3-enzym
AU2005276075B2 (en) 2004-08-26 2010-08-26 National Dairy Development Board A novel cytoplasmic male sterility system for Brassica species and its use for hybrid seed production in Indian oilseed mustard Brassica juncea
EP1805312B9 (fr) 2004-09-23 2009-12-09 Bayer CropScience AG Procédé et moyens pour la production de hyaluronan
US7872036B2 (en) 2004-10-20 2011-01-18 Kumiai Chemical Industry Co., Ltd. 3-triazolylphenyl sulfide derivative and insecticide, miticide and nematicide containing it as an active ingredient
CA2586520A1 (fr) 2004-11-26 2006-06-01 Basf Aktiengesellschaft Composes de 2-cyano-3-(halo)alcoxy-benzenesulfonamide destines au combat des parasites des animaux
AR051690A1 (es) 2004-12-01 2007-01-31 Basf Agrochemical Products Bv Mutacion implicada en el aumento de la tolerancia a los herbicidas imidazolinona en las plantas
EP1672075A1 (fr) 2004-12-17 2006-06-21 Bayer CropScience GmbH Plantes transformées exprimant un dextrane sucrase et synthétisant un amidon modifie
EP1679374A1 (fr) 2005-01-10 2006-07-12 Bayer CropScience GmbH Plantes transformées exprimant un mutane sucrase et synthétisant un amidon modifie
KR20070118133A (ko) 2005-03-24 2007-12-13 바스프 악티엔게젤샤프트 종자 처리를 위한 2-시아노벤젠술폰아미드 화합물
JP2006304779A (ja) 2005-03-30 2006-11-09 Toyobo Co Ltd ヘキソサミン高生産植物
EP1707632A1 (fr) 2005-04-01 2006-10-04 Bayer CropScience GmbH Amidon de pomme de terre cireux phosphorylé
EP1710315A1 (fr) 2005-04-08 2006-10-11 Bayer CropScience GmbH Amidon à forte teneur en phosphate
TWI388282B (zh) 2005-06-01 2013-03-11 Meiji Seika Pharma Co Ltd 害蟲控制劑
WO2006133827A2 (fr) 2005-06-15 2006-12-21 Bayer Bioscience N.V. Methodes permettant d'augmenter la resistance de plantes a des conditions d'hypoxie
KR101468830B1 (ko) 2005-06-24 2014-12-03 바이엘 크롭사이언스 엔.브이. 식물 세포벽의 반응성을 변경하는 방법
AR054174A1 (es) 2005-07-22 2007-06-06 Bayer Cropscience Gmbh Sobreexpresion de sintasa de almidon en vegetales
JPWO2007023719A1 (ja) 2005-08-22 2009-02-26 クミアイ化学工業株式会社 薬害軽減剤及び薬害が軽減された除草剤組成物
EA200800622A1 (ru) 2005-08-24 2008-08-29 Пайонир Хай-Бред Интернэшнл, Инк. Композиции, обеспечивающие толерантность к нескольким гербицидам, и способы их применения
JPWO2007023764A1 (ja) 2005-08-26 2009-02-26 クミアイ化学工業株式会社 薬害軽減剤及び薬害が軽減された除草剤組成物
UA96421C2 (ru) 2005-08-31 2011-11-10 Монсанто Текнолоджи Ллс Нуклеотидная последовательность, кодирующая инсектицидный белок
CA2624973C (fr) 2005-10-05 2016-01-19 Bayer Cropscience Ag Production de hyaluronan a partir de plantes transgeniques pour la synthase de l'hyaluronan, la glutamine fructose-6-phosphate amidotransferase et la deshydrogenase de glucose de diphosphate d'uridine
CN101297041A (zh) 2005-10-05 2008-10-29 拜尔作物科学股份公司 具有增加的乙酰透明质酸ⅱ产量的植物
CA2624592C (fr) 2005-10-05 2016-07-19 Bayer Cropscience Ag Plantes exprimant de la glutamine fructose-6-phosphate amidotransferase avec une production d'hyaluronan accrue
JP4871289B2 (ja) 2005-10-06 2012-02-08 日本曹達株式会社 環状アミン化合物および有害生物防除剤
WO2007043677A1 (fr) 2005-10-14 2007-04-19 Sumitomo Chemical Company, Limited Dérivé d'hydrazide et son utilisation en tant que pesticide
US20090069317A1 (en) 2005-11-21 2009-03-12 Basf Se Insecticidal Methods Using 3-Amino-1,2-Benzisothiazole Derivatives
TW200803740A (en) 2005-12-16 2008-01-16 Du Pont 5-aryl isoxazolines for controlling invertebrate pests
DE102006015468A1 (de) 2006-03-31 2007-10-04 Bayer Cropscience Ag Substituierte Enaminocarbonylverbindungen
DE102006015467A1 (de) 2006-03-31 2007-10-04 Bayer Cropscience Ag Substituierte Enaminocarbonylverbindungen
DE102006015470A1 (de) 2006-03-31 2007-10-04 Bayer Cropscience Ag Substituierte Enaminocarbonylverbindungen
TWI381811B (zh) 2006-06-23 2013-01-11 Dow Agrosciences Llc 用以防治可抵抗一般殺蟲劑之昆蟲的方法
JP5047588B2 (ja) 2006-10-31 2012-10-10 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 キノリン誘導体およびそれを含んでなる農園芸用殺虫剤
BRPI0807371A2 (pt) 2007-03-01 2014-05-06 Basf Se Misturas pesticidas, composto, métodos para proteger plantas do ataque ou de infestação por insetos, acarídeos ou nematódeos, para controlar insertos, aracnídeos ou nematódeos, para proteger sementes, para proteger animais contra infestação ou infecção por parasitas, e para tratar animais infestados ou infectados por parasitas, semente, uso de uma mistura, e, composição pesticida ou parasitica
EP1987718A1 (fr) 2007-04-30 2008-11-05 Bayer CropScience AG Utilisation de pyridine-2-oxy-3-carbonamides en tant que phytoprotecteur
EP1987717A1 (fr) 2007-04-30 2008-11-05 Bayer CropScience AG Pyridinecarboxamide, agent phytoprotecteur la comportant, son procédé de fabrication et son utilisation
GB0720126D0 (en) 2007-10-15 2007-11-28 Syngenta Participations Ag Chemical compounds
EP2247600A4 (fr) 2008-02-06 2011-09-14 Biomarin Pharm Inc Inhibiteurs à base de composés benzoxazole-carboxamide de l activité poly(adp-ribose)polymérase (parp)
JP5268461B2 (ja) 2008-07-14 2013-08-21 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Ｐｆ１３６４物質、その製造方法、生産菌株、及び、それを有効成分とする農園芸用殺虫剤
FR2934943B1 (fr) 2008-08-12 2011-06-17 Algieplus Utilisation d'apiogalacturonanes et de ses derives pour la stimulation des reactions de defense et de resistance des plantes contre le stress biotiques et abiotiques
WO2010083220A1 (fr) * 2009-01-19 2010-07-22 Abbott Laboratories Inhibiteurs de poly(adp-ribose)polymérase de type benzoxazole
WO2010083199A1 (fr) * 2009-01-19 2010-07-22 Abbott Laboratories Inhibiteurs benzthiazole de la poly(adp-ribose)polymérase
WO2010122956A1 (fr) 2009-04-20 2010-10-28 花王株式会社 Composition pour communiquer une tolérance au stress à une plante
EP2248421A1 (fr) 2009-05-07 2010-11-10 GMI - Gregor-Mendel-Institut für Molekulare Pflanzenbiologie GmbH Accumulation de biomasse dans les plantes
US8822515B2 (en) 2009-10-16 2014-09-02 University Of Maryland, Baltimore County Heterocyclic benzoxazole compositions as inhibitors of hepatitis C virus
AR080443A1 (es) * 2010-03-04 2012-04-11 Bayer Cropscience Ag 2-amidobencimidazoles sustituidos con fluruoalquilo

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2014037340A1 *

Also Published As

Publication number Publication date
CA2883574A1 (fr) 2014-03-13
CN104780764A (zh) 2015-07-15
WO2014037340A1 (fr) 2014-03-13
EA201590482A1 (ru) 2015-07-30
US20150216168A1 (en) 2015-08-06
BR112015004858A2 (pt) 2017-07-04
AU2013311826A1 (en) 2015-03-26
JP2015532650A (ja) 2015-11-12

Similar Documents

Publication Publication Date Title
EP2892345A1 (fr) Utilisation de 2-amidobenzimidazoles, de 2-amidobenzoxazoles et de 2-amidobenzothiazoles substitués ou de leurs sels comme principes actifs contre le stress abiotique des plantes
EP2611300B1 (fr) Dérivés de dihydropyrimdinone annelés et substitués
WO2012089721A1 (fr) Utilisation d&#39;acides sulfonamido-carboxyliques spirocycliques substitués, de leurs esters d&#39;acide carboxylique, de leurs amides d&#39;acide carboxylique et de leurs carbonitriles ou de leurs sels pour augmenter la tolérance au stress chez des plantes.
EP2729007A1 (fr) Utilisation d&#39;isoquinoléinones, d&#39;isoquinoléinediones, d&#39;isoquinoléinetriones et de dihydroisoquinoléinones substituées ou de leurs sels comme principes actifs contre le stress abiotique des plantes
EP2892344A1 (fr) Utilisation de benzodiazepinones et de benzazepinones substituées ou de leurs sels comme principes actifs contre le stress abiotique des plantes
AU2012242124B2 (en) Substituted 5-(cyclohex-2-en-1-yl)-penta-2,4-dienes and 5-(cyclohex-2-en-1-yl)-pent-2-en-4-ynes as active agents against abiotic stress in plants
WO2011113861A2 (fr) Aryl- et hétarylsulfonamides en tant que substances actives contre le stress abiotique des végétaux
EP2928297A1 (fr) Utilisation de 1-(aryléthinyl)-bicycloalcanols, 1-(hétéroaryléthinyl)-bicycloalcanols, 1-(hétérocyclyléthinyl)-bicycloalcanols et 1-(cyloalcényléthinyl)-bicycloalcanols substitués comme principes actifs contre le stress abiotique des plantes
EP2757886A1 (fr) Utilisation de dérivés d&#39;acide 1-phényl-pyrazol-3-carboxylique à substitution en position 4 en tant qu&#39;agents actifs contre le stress abiotique chez les végétaux
WO2012139891A1 (fr) Vinyl- et alcinyl-cyclohexénols substitués en tant que principes actifs contre le stress abiotique des végétaux
EP2928296A1 (fr) Utilisation de 1-(aryléthinyl)-cyclohexanols, 1-(hétéroaryléthinyl)-cyclohexanols, 1-(hétérocyclyléthinyl)-cyclohexanols et 1-(cyloalcényléthinyl)-cyclohexanols substitués comme principes actifs contre le stress abiotique des plantes
EP2555619A2 (fr) Utilisation de l&#39;acide 4-phényl butyrique et/ou de ses sels pour augmenter la tolérance au stress chez des végétaux
CN102884054B (zh) 氟烷基取代的2-氨基苯并咪唑及其用于提高植物胁迫耐受性的用途
WO2022268520A1 (fr) Utilisation de pyrrolidinones substituées ou de leurs sels pour augmenter la tolérance au stress des plantes
EP2510786A1 (fr) Dérivés de prop-2-yn-1-ol et prop-2-en-1-ol substitués
JP2014515746A (ja) 非生物的植物ストレスに対する活性化合物としての置換５−（ビシクロ［４．１．０］ヘプト−３−エン−２−イル）ペンタ−２，４−ジエン類および５−（ビシクロ［４．１．０］ヘプト−３−エン−２−イル）ペント−２−エン−４−イン類
EP2892343A1 (fr) Utilisation d&#39;acide 2,3-dihydro-1-benzofurane-4-carboxylique substitué ou de ses sels comme principes actifs contre le stress abiotique des plantes
EP2740356A1 (fr) Dérivés d&#39;acides (2Z)-5(1-hydroxycyclohexyl)pent-2-en-4-ines substitués
EP2740720A1 (fr) Dérivés d&#39;acides pent-2-en-4-ines bicycliques et tricycliques substitués et leur utilisation pour augmenter la tolérance au stress chez les plantes
EP2555626A2 (fr) Utilisation de dérivés de l&#39;acide (1-cyanocyclopropyl)phényl phosphinique, de leurs esters et/ou de leurs sels pour augmenter la tolérance de végétaux au stress abiotique

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: 20151124