Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
  • C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
  • C07D239/10—Oxygen or sulfur atoms
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—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
• • 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
  • A01N47/20—N-Aryl derivatives thereof
• • 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
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
  • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D233/30—Oxygen or sulfur atoms
  • C07D233/32—One oxygen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
  • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D233/30—Oxygen or sulfur atoms
  • C07D233/32—One oxygen atom
  • C07D233/36—One oxygen atom with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
  • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D233/30—Oxygen or sulfur atoms
  • C07D233/42—Sulfur atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
  • C07D243/04—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 3
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
  • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
• • 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
  • C07D413/06—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 only aliphatic carbon atoms

Definitions

• n 1, 2 or 3
• Q oxygen or sulfur
• R.1 represents hydrogen, formyl or optionally substituted alkyl, alkoxy, alkylamino, dialkylamino, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl, and
• R2 represents an optionally substituted, optionally heterocyclically fused, monocyclic or bicyclic aromatic group.
• hydrocarbon chains such as alkyl
• heteroatoms such as in alkoxy.
• n is preferably 1, 2 or 3;
• Q preferably represents oxygen or sulfur
• Rl preferably represents hydrogen, formyl or for alkyl, alkoxy, alkylamino, dialkylamino, each substituted by cyano, halogen, C1-C4-alkoxy, C 1 -C 4 -alkylcarbonyl, C [-C4-alkoxycarbonyl or morpholinyl 1 to 6 carbon atoms in the alkyl groups, for alkenyl or alkynyl, each optionally substituted by cyano, halogen or C 1 -C 4 -alkoxycarbonyl, or each having 2 to 6 carbon atoms, or for each optionally substituted by cyano, halogen or C 1 -C 4 -alkyl Cycloalkyl or cycloalkylalkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part;
• R 2 preferably represents the aromatic group defined below
• R3 for hydrogen, nitro, amino, cyano, formylamino, halogen, or for each optionally by cyano, halogen or Cj-C4-alkoxy substituted alkyl, alkoxy, alkylcarbonylamino, alkoxycarbonylamino, alkylaminocarbonylamino each having 1 to 6 carbon atoms in the alkyl groups, or for cycloalkylcarbonylamino having 3 to 6 carbon atoms optionally substituted by cyano, halogen, Cj-C4-A_kyl or Cj-C4-haloalkyl in the cycloalkyl part, or phenylcarbonylamino which is optionally substituted by cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 halooxy;
• R5 represents nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, fluorine, chlorine, bromine or alkyl, alkoxy, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by fluorine and / or chlorine, each having up to 4 carbon atoms;
• A represents a single bond, represents oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -NA ⁇ -, where A ⁇ represents hydrogen, hydroxy, C1-C4-alkyl, C3-C4-alkenyl, C3-C -alkynyl, C1-C4-
• a 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO2-, -CO- or the group -NA ⁇ -, where A ⁇ represents hydrogen,
• R preferably represents hydrogen, fluorine or chlorine
• R5 preferably represents cyano, thiocarbamoyl, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy;
• R6 particularly preferably stands for the following grouping:
• a 2 represents a single bond, represents oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -NA 4 -, wherein A 4 represents hydrogen,
• a 2 also for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2- diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl,
• R ⁇ preferably represents hydrogen, fluorine or chlorine.
• Q 3 , Q 4 and Q ⁇ are the same or different and each represents oxygen or sulfur
• Q very particularly preferably represents oxygen or sulfur
• Rl very particularly preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy;
• R 7 particularly preferably represents hydrogen.
• n 1 or 2
• R 1 represents in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, and
• R 3 represents hydrogen, fluorine or chlorine
• n 1 or 2
• Rl is in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, and
• R 2 represents the aromatic group defined below
• R 3 represents hydrogen, fluorine or chlorine
• R 4 represents hydrogen
• R5 represents cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl
• a 2 stands for -SO 2 -
• R 7 represents hydrogen
• the new substituted 1,3-diaza-2- (thi) oxo-cycloalkanes of the general formula (I) are notable for strong and selective herbicidal activity.
• the new substituted 1,3-diaza-2- (thi) oxo-cycloalkanes of the general formula (I) are obtained if
• Y 1 and Y 2 are identical or different and each represent halogen (in particular chlorine), alkoxy (in particular methoxy or ethoxy), alkoxyalkoxy (in particular (methoxyethoxy or ethoxyethoxy), phenoxy or imidazolyl,
• reaction auxiliary e.g. Pyridine
• a diluent e.g. Toluene
• reaction auxiliary such as e.g. Ethyl diisopropyl amine
• diluent such as e.g. Acetonitrile
• the starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. J. Am. Chem. Soc. 80 (1958), 6409-6412; J. Chem. Soc. Perkin Trans. 1, 1981, 2499-2503; J. Org. Chem. 22 (1957), 1581; J. Org. Chem. 28 (1992), 7339-7342; Synth. Commun. 27 (1997), 3565-3571).
• EP-A-431373, EP-A-441004, EP-A-597360 The process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out using a diluent.
• Inert organic solvents are particularly suitable as diluents.
• Formula (I) is preferably carried out using a reaction auxiliary.
• the usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as, for example
• Phosphate buffer solution acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with b) .
• the calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).
• Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amounts of active ingredient are applied per unit area.
• the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.
• the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Plural Heterocyclic Compounds (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)
• Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

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• 1998
  • 1998-05-20 DE DE19822678A patent/DE19822678A1/de not_active Withdrawn
• 1999
  • 1999-05-18 JP JP2000549596A patent/JP2002515492A/ja active Pending
  • 1999-05-18 KR KR1020007012595A patent/KR20010043505A/ko not_active Application Discontinuation
  • 1999-05-18 EP EP99952091A patent/EP1080077A1/de not_active Withdrawn
  • 1999-05-18 AU AU42639/99A patent/AU4263999A/en not_active Abandoned
  • 1999-05-18 BR BR9910610-8A patent/BR9910610A/pt not_active Application Discontinuation
  • 1999-05-18 WO PCT/EP1999/003422 patent/WO1999059977A1/de not_active Application Discontinuation
  • 1999-05-18 CA CA002332443A patent/CA2332443A1/en not_active Abandoned
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