US20040029735A1 - Substituted herbicidal phenyluracils - Google Patents

Substituted herbicidal phenyluracils Download PDF

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US20040029735A1
US20040029735A1 US10/629,249 US62924903A US2004029735A1 US 20040029735 A1 US20040029735 A1 US 20040029735A1 US 62924903 A US62924903 A US 62924903A US 2004029735 A1 US2004029735 A1 US 2004029735A1
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cyano
carbamoyl
fluorine
chlorine
carboxyl
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Roland Andree
Hans-Georg Schwarz
Mark Drewes
Peter Dahmen
Dieter Feucht
Rolf Pontzen
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    • 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
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C07C255/59—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/456—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 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 other ring carbon atoms
    • 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
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
    • 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
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid

Definitions

  • the invention relates to novel substituted phenyluracils, to processes and novel intermediates for their preparation and to their use as herbicides.
  • This invention accordingly, provides novel substituted phenyluracils of the general formula (I)
  • m 0, 1, 2 or 3
  • n 0, 1, 2, 3 or 4
  • Q represents O (oxygen), S (sulphur), SO, SO 2 , NH or N(alkyl),
  • R 1 represents hydrogen, amino or optionally substituted alkyl
  • R 2 represents carboxyl, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted alkyl or alkoxycarbonyl,
  • R 3 represents hydrogen, halogen or optionally substituted alkyl
  • R 4 represents hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen
  • R 5 represents cyano, carbamoyl, thiocarbamoyl, halogen or in each case optionally substituted alkyl or alkoxy,
  • x represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, al
  • Y represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulplhonyl, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkiny
  • m preferably represents 0, 1 or 2.
  • n preferably represents 0, 1, 2 or 3.
  • Q preferably represents O (oxygen), S (sulphur), SO, SO 2 , NH or N(C 1 -C 4 -alkyl).
  • R 1 preferably represents hydrogen, amino or represents optionally cyano-, halogen- or C 1 -C 3 -alkoxy-substituted alkyl having 1 to 4 carbon atoms.
  • R 2 preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, halogen- or C 1 -C 3 -alkoxy-substituted alkyl or alkoxycarbonyl having in each case 1 to 4 carbon atoms.
  • R 3 preferably represents hydrogen, halogen or represents optionally cyano-, halogen- or C 1 -C 3 -alkoxy-substituted alkyl having 1 to 4 carbon atoms.
  • R 4 preferably represents hydrogen, cyano, fluorine or chlorine.
  • R 5 preferably represents cyano, carbamoyl, thiocarbamoyl, halogen or represents in each case optionally halogen-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms.
  • X preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -alkylsulphinyl-, C 1 l-C 4 -alkylsulphonyl-, C 1 -C 4 -alkyl-carbonyl-, C 1 -C 4 -alkoxy-carbonyl-, C 2 -C 4 -alkenyloxy-carbonyl-, C 2 -C 4 -alkinyloxy-carbonyl-, C 1 -C 4 -alkylamino-carbonyl-
  • Y preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -alkylsulphinyl-, C 1 -C 4 -alkylsulphonyl-, C 1 -C 4 -alkyl-carbonyl-, C 1 -C 4 -alkoxy-carbonyl-, C 2 -C 4 -alkenyloxy-carbonyl-, C 2 -C 4 -alkinyloxy-carbonyl-, aminocarbonyl-, C 1 -C 4 -alkylamino
  • the invention also preferably provides the sodium, potassium, magnesium, calcium, arnmonium, C 1 -C 4 -alkyl-ammonium, di-(C 1 -C 4 -alkyl)-ammonium, tri-(C 1 -C 4 -alkyl)-ammonium, tetra-(C 1 -C 4 -alkyl)-ammonium, tri-(C 1 -C 4 -alkyl)-sulphonium, C 5 - or C 6 -cycloalkyl-ammonium and di-(C 1 -C 2 -alkyl)-benzyl-ammonium salts of compounds of the formula (I), in which m, n, Q. R 1 , R 2 , R 3 , R 4 , R 5 , X and Y have the preferred meanings given above—insofar as the compounds of the formula (I) contain hydrogen atoms attached to O or S.
  • m particularly preferably represents 0 or 1.
  • n particularly preferably represents 0, 1 or 2.
  • Q particularly preferably represents O (oxygen) or S (sulphur).
  • R 1 particularly preferably represents hydrogen, amino or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl.
  • R 2 particularly preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl.
  • R 3 particularly preferably represents hydrogen, fluorine, chlorine, bromine, or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl.
  • R 4 particularly preferably represents hydrogen, fluorine or chlorine.
  • R 5 particularly preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy.
  • X particularly preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulphonyl, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-, acetyl-
  • Y particularly preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulphonyl, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-, acetyl-
  • m very particularly preferably represents 0.
  • n very particularly preferably represents 0 or 1.
  • Q very particularly preferably represents O (oxygen).
  • R 1 very particularly preferably represents hydrogen, amino or methyl.
  • R 2 very particularly preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, methoxycarbonyl or ethoxycarbonyl.
  • R 3 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, or represents optionally fluorine- and/or chlorine-substituted methyl.
  • R 4 very particularly preferably represents fluorine.
  • R 5 very particularly preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl or methoxy.
  • X very particularly preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulphonyl, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbon
  • Y very particularly preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulpho, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulfonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbony
  • R 2 most preferably represents trifluoromethyl.
  • R 3 most preferably represents hydrogen.
  • R 5 most preferably represents cyano.
  • Y most preferably represents hydroxyl, methoxy, represents in each case methoxycarbonyl-, ethoxycarbonyl-, methylaminocarbonyl-, dimethylaminocarbonyl or phenylaminocarbonyl-substituted methoxy or ethoxy, represents methylaminocarbonyloxy, ethylcarbonyloxy, propinyloxy, butinyloxy or ethoxycarbonyloxy.
  • a very particularly preferred group is the compounds of the general formula (IA)
  • n, Q, R 1 , R 2 , R 3 , R 4 , R 5 and Y each have the meanings given above as being very particularly preferred or most preferred.
  • a further very particularly preferred group is the compounds of the general formula (IB)
  • n, Q, R 1 , R 2 , R 3 , R 4 , R 5 and Y each have the meanings given above as being very particularly preferred or as being most preferred.
  • radical definitions apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another at will, i.e. including combinations between the given preferred ranges.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
  • heteroatoms such as in alkoxy
  • Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitution the substituents can be identical or different.
  • the invention relates in each case to the R enantiomers and the S enantiomers and to any mixures of these enantiomers, in particular the racemates.
  • the invention relates in each case to the possible E and Z isomers and their mixtures.
  • Q, R 1 , R 2 , R 3 , R 4 , R 5 and Y each have the meanings given below in tabular form.
  • Q R 1 R 2 R 3 R 4 R 5 Y O H CF 3 H F CN — O CH 3 CF 3 H F CN — S H CF 3 H F CN — S CH 3 CF 3 H F CN — O H CF 3 Cl F CN — O CH 3 CF 3 Cl F CN — O H CF 3 CH 3 F CN — O CH 3 CF 3 CH 3 F CN — O H CF 3 H F CN OH O CH 3 CF 3 H F CN OH O H CF 3 H F CN OCH 3 O CH 3 CF 3 H F CN OCH 3 O CH 3 CF 3 H F CN OCH 3 O CH 3 CF 3 H F CN OCH 3 O CH 3 CF 3 H F CN OCH 3 O CH 3 CF 3 H F CN OCH 3 O H CN H F CN OCH
  • Q, R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given above in Group 1 in tabular form; X has the meanings given above in Group 1 for Y.
  • novel substituted phenyluracils of the general formula (I) have interesting biological properties. In particular, they have strong herbicidal activity.
  • R 1 , R 2 , R 3 , R 4 and R 5 are each as defined above and
  • X 1 represents halogen
  • n, Q, X und Y are each as defined above,
  • R 2 and R 3 are each as defined above and
  • R represents alkyl, aryl or arylalkyl
  • m, n, Q, R 4 , R 5 , X and Y are as defined above and
  • R represents alkyl, aryl or arylalkyl
  • m, n, Q, R 3 , R 4 , R 5 , X and Y are as defined above and
  • R′ represents alkyl
  • m, n, Q, R 2 , R 3 , R 4 , R 5 , X and Y are as defined above,
  • a 1 represents optionally substituted alkyl
  • X 2 represents halogen or the grouping —O—SO 2 —O—A 1 ,
  • the compounds of the general formula (I) can be converted by customary methods into other compounds of the general formula (I) according to the above definition, for example by etherification or ether cleavage (X,Y: OH ⁇ OC 2 H 5 , OCH 3 ⁇ OH), esterification or hydrolysis (for example X: OCH 2 COOH ⁇ OCH 2 COOC 2 H 5 , OCH(CH 3 )COOCH 3 ⁇ OCH(CH 3 )COOH), reaction with dicyano or hydrogen sulphide (for example R 5 : Br ⁇ CN, CN ⁇ CSNH 2 ), conversion of carboxyl compounds into other carboxylic acid derivatives by customary methods (for example R 2 : COOH ⁇ CN, COOH ⁇ COOCH 3 ), conversion of sulfonic acid derivatives according to customary methods (for example X,Y: SO 3 Na ⁇ SO 2 Cl, SO 2 Cl ⁇ SH), halogenation (for example X,Y: CH 3 ⁇ CH 2 Cl or CH 2 Br)—cf.
  • the formula (II) provides a general definition of the halogenophenyluracils to be used as starting materials in the process (a) according to the invention for preparing compounds of the formula (I).
  • R 1 , R 2 , R 3 , R 4 and R 5 each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for R 1 , R 2 , R 3 , R 4 and R 5 ;
  • X 1 preferably represents fluorine or chlorine, in particular fluorine.
  • the formula (III) provides a general definition of the naphthalene derivatives further to be used as starting materials in the process (a) according to the invention.
  • m, n, Q, X and Y each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for m, n, Q, X and Y.
  • the starting materials of the general formula (III) are known organic chemicals for synthesis.
  • the formula (IV) provides a general definition of the aminoalkenoic acid esters to be used as starting materials in the process (b) according to the invention for preparing compounds of the general formula (I).
  • R 2 and R 3 each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for R 2 and R 3 ;
  • R preferably represents C 1 -C 4 -alkyl, phenyl or benzyl, in particular methyl or ethyl.
  • Formula (V) provides a general definition of the aryl isocyanates further to be used as starting materials in the process (b) according to the invention.
  • m, n, Q, R 4 , R 5 , X and Y each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for m, n, Q, R 4 , R 5 , X and Y.
  • novel aryl isocyanates of the general formula (V) are obtained by reacting aniline derivatives of the general formula (IX)
  • n, Q, R 4 , R 5 , X and Y are each as defined above
  • the formula (VI) provides a general definition of the arylurethanes to be used, if appropriate, as starting materials in the process (b) according to the invention.
  • m, n, Q, R 4 , R 5 , X and Y each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for m, n, Q, R 4 , R 5 , X and Y; R preferably represents C 1 -C 4 -alkyl, phenyl or benzyl, in particular methyl or ethyl.
  • novel arylurethanes of the general formula (VI) are obtained by reacting aniline derivatives of the general formula (IX)
  • n, Q, R 4 , R 5 , X and Y are each as defined above,
  • R is as defined above
  • novel aniline derivatives of the general formula (IX) are obtained by reacting anilines of the general formula (XI)
  • R 4 , R 5 and X 1 are each as defined above,
  • n, Q, X and Y are each as defined above,
  • reaction auxiliary such as, for example, sodium hydride
  • a diluent such as, for example, N-methyl-pyrrolidone
  • the formula (VII) provides a general definition of the N-aryl-1-alkoxycarbonylamino-maleimides to be used as starting materials in the process (c) according to the invention for preparing compounds of the general formula (I).
  • m, n, Q, R 3 , R 4 , R 5 , X and Y each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred, very particulaly preferred or most preferred for m, n, Q, R 3 , R 4 , R 5 , X and Y; R′ preferably represents C 1 -C 4 -alkyl, in particular methyl or ethyl.
  • novel N-aryl-1-alkoxycarbonylamino-maleimides of the general formula (VII) are obtained by reacting alkyl (2,5-dioxo-2,5-dihydro-furan-3-yl)-carbamates of the general formula (XII)
  • R 3 is as defined above and
  • R′ represents alkyl, (in particular methyl or ethyl),
  • n, Q, R 4 , R 5 , X and Y are each as defined above,
  • a diluent such as, for example, acetic acid
  • the formula (Ia) provides a general definition of the substituted phenyluracils to be used as starting materials in the process (d) according to the invention for preparing compounds of the formula (I).
  • m, n, Q, R 2 , R 3 , R 4 , R 5 , X and Y each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for m, n, Q, R 2 , R 3 , R 4 , R 5 , X and Y.
  • the starting materials of the general formula (Ia) for process (b) also form part of the subject-matter of the present application; they can be prepared according to processes (a), (b) and (c) according to the invention.
  • a 1 preferably represents optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl having 1 to 4 carbon atoms and X 2 represents chlorine, bromine, iodine, methylsulphonyloxy or ethylsulphonyloxy;
  • a 1 particularly preferably represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl and
  • X 2 represents chlorine, bromine, iodine, methylsulphonyloxy or ethylsulphonyloxy.
  • the starting materials of the formula (VIII) are known organic chemicals for synthesis.
  • Suitable diluents for carrying out the processes (a), (b), (c) and (d) according to the invention are, in addition to water, especially inert organic solvents.
  • aliphatic, alicyclic or aromatic optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidon
  • Suitable reaction auxiliaries for the processes (a), (b), (c) and (d) according to the invention are, in general, the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, such as, for example, sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide, or potassium methoxide, ethoxide, n
  • phase-transfer catalysts are phase-transfer catalysts. Examples of such catalysts which may be mentioned are:
  • reaction temperatures can be varied within a relatively wide range.
  • the processes are carried out at temperatures between 0° C. and 150° C., preferably between 10° C. and 120° C.
  • the processes according to the invention are generally carried out under atmospheric pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure—in general between 0.1 bar and 10 bar.
  • the starting materials are generally employed in approximately equimolar amounts. However, it is also possible for one of the components to be used in a relatively large excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for several hours. Work-up is carried out by customary methods (cf. the Preparation Examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed killers.
  • weeds in the broadest sense there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can be used, for example, in connection with the following plants:
  • Dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
  • the active compounds according to the invention are suitable for total weed control, for example on industrial terrain and railway tracks and on paths and areas with or without tree growth.
  • the active compounds according to the invention can be employed for controlling weeds in perennial crops, for example forests, ornamental tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns and turf and pastures and for selective weed control in annual crops.
  • the active compounds of the formula (I) according to the invention have strong herbicidal activity and a broad activity spectrum when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both by the pre-emergence and by the post-emergence method.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic substances impregnated with active compound, and microencapsulations in polymeric substances.
  • formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is to say liquid solvents and/or solid carriers, optionally with the use of surfactants, that is to say emulsifiers and/or dispersants and/or foam formers.
  • Liquid solvents which are mainly suitable are: 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 also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or m
  • Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates;
  • suitable solid carriers for granules are: for example crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic meals, and granules of organic material, such as sawdust, coconut shells, maize cobs and tobacco stalks;
  • suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyetliylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, ary
  • Tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other possible additives are mineral and vegetable oils.
  • dyestuffs such as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments for example iron oxide, titanium oxide, Prussian blue
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations generally comprise between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, is also possible.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing.
  • the amount of active compound used can vary within a relatively wide range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.
  • the mixture is concentrated under water-pump vacuum, the residue is shaken with ethyl acetate/1N hydrochloric acid and the organic phase is separated off, washed with saturated aqueous sodium chloride solution, dried with sodium sulphate and filtered. The filtrate is concentrated under water-pump vacuum, the residue is digested with diethyl ether and the resulting crystalline product is isolated by filtration with suction.
  • the lambda-max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • Example 31 The compound listed above in Table 1 as Example 31 can be prepared, for example, as follows:
  • Example 33 The compound listed above in Table 1 as Example 33 can be prepared, for example, as follows:
  • Example 35 The compound listed above in Table 1 as Example 35 can be prepared, for example, as follows:
  • Example (IX-1) Analogously to Example (IX-1), it is also possible to prepare, for example, the compounds of the general formula (IX) listed in Table 3 below. TABLE 3 Examples of the compounds of the formula (IX) Ex. No. Q R 4 R 5 Physical Data IX-2 O F CN 1 H-NMR (D 6 -DMSO, ⁇ ): 8.03, 8.06 ppm IX-3 O F CN m.p.: 130° C. IX-4 O F CN m.p.: 144° C.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the preparation of active compound such that the particular amount of active compound desired is applied per unit area.
  • the concentration of the spray liquor is chosen so that the particular amount of active compound desired is applied in 1000 litres of water per hectare.
  • Post-Emergence Test Solvent 5 parts by weight of acetone
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Test plants of a height of 5-15 cm are sprayed with the preparation of active compound such that the particular amounts of active compound desired are applied per unit area.
  • the concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 1000 1 of water/ha.

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Abstract

The invention relates to novel substituted phenyluracils of the general formula (I)
Figure US20040029735A1-20040212-C00001
in which
m, n, Q, R1, R2, R3, R4, R5, X and Y are each as defined in the description,
to processes for their preparation, to novel intermediates and to their use as herbicides.

Description

  • The invention relates to novel substituted phenyluracils, to processes and novel intermediates for their preparation and to their use as herbicides. [0001]
  • Certain substituted aryluracils are already known from the (patent) literature (cf. EP-A-255 047, EP-A-260 621, EP-A-408 382, EP-A-438 209, EP-A-473 551, EP-A-517 181, EP-A-563 384, WO-A-91/00278, WO-A-91/07393, WO-A-93/14073, U.S. Pat. No. 4,979,982, U.S. Pat. No. 5,084,084, U.S. Pat. No. 5,127,935, U.S. Pat. No. 5,154,755, U.S. Pat. No. 5,169,430, U.S. Pat. No. 5,486,610, U.S. Pat. No. 5,356,863). However, these compounds have hitherto not attained any particular importance. [0002]
  • This invention, accordingly, provides novel substituted phenyluracils of the general formula (I) [0003]
    Figure US20040029735A1-20040212-C00002
  • in which [0004]
  • m represents 0, 1, 2 or 3, [0005]
  • n represents 0, 1, 2, 3 or 4, [0006]
  • Q represents O (oxygen), S (sulphur), SO, SO[0007] 2, NH or N(alkyl),
  • R[0008] 1 represents hydrogen, amino or optionally substituted alkyl,
  • R[0009] 2 represents carboxyl, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted alkyl or alkoxycarbonyl,
  • R[0010] 3 represents hydrogen, halogen or optionally substituted alkyl,
  • R[0011] 4 represents hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,
  • R[0012] 5 represents cyano, carbamoyl, thiocarbamoyl, halogen or in each case optionally substituted alkyl or alkoxy,
  • x represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl, alkinylcarbonyloxy or arylcarbonyloxy, and [0013]
  • Y represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulplhonyl, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl, alkinylcarbonyloxy or arylcarbonyloxy, where, in the case that m and/or are greater than 1, X and Y in the individual compounds possible in each case have identical or different meanings from those given, [0014]
  • and salts of compounds of the formula (I). [0015]
  • Preferred substituents or ranges of the radicals present in the formulae given above and below are defined below. [0016]
  • m preferably represents 0, 1 or 2. [0017]
  • n preferably represents 0, 1, 2 or 3. [0018]
  • Q preferably represents O (oxygen), S (sulphur), SO, SO[0019] 2, NH or N(C1-C4-alkyl).
  • R[0020] 1 preferably represents hydrogen, amino or represents optionally cyano-, halogen- or C1-C3-alkoxy-substituted alkyl having 1 to 4 carbon atoms.
  • R[0021] 2 preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, halogen- or C1-C3-alkoxy-substituted alkyl or alkoxycarbonyl having in each case 1 to 4 carbon atoms.
  • R[0022] 3 preferably represents hydrogen, halogen or represents optionally cyano-, halogen- or C1-C3-alkoxy-substituted alkyl having 1 to 4 carbon atoms.
  • R[0023] 4 preferably represents hydrogen, cyano, fluorine or chlorine.
  • R[0024] 5 preferably represents cyano, carbamoyl, thiocarbamoyl, halogen or represents in each case optionally halogen-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms.
  • X preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C[0025] 1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-, C1l-C4-alkylsulphonyl-, C1-C4-alkyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C2-C4-alkenyloxy-carbonyl-, C2-C4-alkinyloxy-carbonyl-, C1-C4-alkylamino-carbonyl-, di-(C1-C4-alkyl)-amino-carbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6 carbon atoms, represents dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, bis-alkylsulfonyl-amino or N-alkylcarbonyl-N-alkylsulphonyl-amino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C1-C4-alkoxycarbonyl-, C1-C4-alkylamino-carbonyl- or di-(C1-C4-alkyl)-amino-carbonyl-substituted alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl or alkinylcarbonyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups, or represents benzyloxy.
  • Y preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C[0026] 1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-, C1-C4-alkylsulphonyl-, C1-C4-alkyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C2-C4-alkenyloxy-carbonyl-, C2-C4-alkinyloxy-carbonyl-, aminocarbonyl-, C1-C4-alkylaminocarbonyl-, di-(C1-C4-alkyl)-amino-carbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6 carbon atoms, represents dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, bis-alkylsulfonyl-amino or N-alkylcarbonyl-N-alkylsulphonyl-amino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C1-C4-alkoxycarbonyl-, C1-C4-alkylamino-carbonyl- or di-(C1-C4-alkyl)-amino-carbonyl-substituted alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl or alkinylcarbonyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups, or represents benzyloxy.
  • The invention also preferably provides the sodium, potassium, magnesium, calcium, arnmonium, C[0027] 1-C4-alkyl-ammonium, di-(C1-C4-alkyl)-ammonium, tri-(C1-C4-alkyl)-ammonium, tetra-(C1-C4-alkyl)-ammonium, tri-(C1-C4-alkyl)-sulphonium, C5- or C6-cycloalkyl-ammonium and di-(C1-C2-alkyl)-benzyl-ammonium salts of compounds of the formula (I), in which m, n, Q. R1, R2, R3, R4, R5, X and Y have the preferred meanings given above—insofar as the compounds of the formula (I) contain hydrogen atoms attached to O or S.
  • m particularly preferably represents 0 or 1. [0028]
  • n particularly preferably represents 0, 1 or 2. [0029]
  • Q particularly preferably represents O (oxygen) or S (sulphur). [0030]
  • R[0031] 1 particularly preferably represents hydrogen, amino or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl.
  • R[0032] 2 particularly preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl.
  • R[0033] 3 particularly preferably represents hydrogen, fluorine, chlorine, bromine, or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl.
  • R[0034] 4 particularly preferably represents hydrogen, fluorine or chlorine.
  • R[0035] 5 particularly preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy.
  • X particularly preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulphonyl, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, n-, i-, s- or t-butoxycarbonyl-, propenyloxycarbonyl-, butenyloxycarbonyl-, propinyloxycarbonyl-, butinyloxycarbonyl-, methlylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, represents dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-oder i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, n-, i-, s- or t-butoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, n-, i-, s- or t-butylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, acetylamino, propionylamino, n- or i-butyroylamino methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonyl, or represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or diethylaminocarbonyl-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, ethenecarbonyloxy, propenecarbonyloxy, butenecarbonyloxy, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonyl, butinyloxycarbonyl, ethinecarbonyloxy, propinecarbonyloxy or butinecarbonyloxy, or represents benzoyloxy. [0036]
  • Y particularly preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulphonyl, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, n-, i-, s- or t-butoxycarbonyl-, propenyloxycarbonyl-, butenyloxycarbonyl-, propinyloxycarbonyl-, butinyloxycarbonyl-, aminocarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, represents dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methylcarbonyloxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy, n- or i-butyroyloxy, methylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, n-, i-, s- or t-butoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, n-, i-, s- or t-butylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, or represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or diethylaminocarbonyl-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, ethenecarbonyloxy, propenecarbonyloxy, butenecarbonyloxy, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonyl, butinyloxycarbonyl, ethinecarbonyloxy, propinecarbonyloxy or butinecarbonyloxy, or represents benzoyloxy. [0037]
  • m very particularly preferably represents 0. [0038]
  • n very particularly preferably represents 0 or 1. [0039]
  • Q very particularly preferably represents O (oxygen). [0040]
  • R[0041] 1 very particularly preferably represents hydrogen, amino or methyl.
  • R[0042] 2 very particularly preferably represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, methoxycarbonyl or ethoxycarbonyl.
  • R[0043] 3 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, or represents optionally fluorine- and/or chlorine-substituted methyl.
  • R[0044] 4 very particularly preferably represents fluorine.
  • R[0045] 5 very particularly preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl or methoxy.
  • X very particularly preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulphonyl, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, propenyloxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or benzyloxycarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, represents dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-oder i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, or represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or diethylaminocarbonyl-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propenyloxycarbonyl or butinyloxycarbonyl, or represents benzoyloxy. [0046]
  • Y very particularly preferably represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulpho, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulfonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, propenyloxycarbonyl-, aminocarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, phenylaminocarbonyl- or benzyloxycarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n-oder i-propylamino, represents dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy, n- or i-butyroyloxy, methylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonyamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, or represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl-, etboxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or diethylaminocarbonyl-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonyl or butinyloxycarbonyl, or represents benzoyloxy. [0047]
  • R[0048] 2 most preferably represents trifluoromethyl.
  • R[0049] 3 most preferably represents hydrogen.
  • R[0050] 5 most preferably represents cyano.
  • Y most preferably represents hydroxyl, methoxy, represents in each case methoxycarbonyl-, ethoxycarbonyl-, methylaminocarbonyl-, dimethylaminocarbonyl or phenylaminocarbonyl-substituted methoxy or ethoxy, represents methylaminocarbonyloxy, ethylcarbonyloxy, propinyloxy, butinyloxy or ethoxycarbonyloxy. [0051]
  • A very particularly preferred group is the compounds of the general formula (IA) [0052]
    Figure US20040029735A1-20040212-C00003
  • in which [0053]
  • n, Q, R[0054] 1, R2, R3, R4, R5 and Y each have the meanings given above as being very particularly preferred or most preferred.
  • A further very particularly preferred group is the compounds of the general formula (IB) [0055]
    Figure US20040029735A1-20040212-C00004
  • in which [0056]
  • n, Q, R[0057] 1, R2, R3, R4, R5 and Y each have the meanings given above as being very particularly preferred or as being most preferred.
  • The abovementioned or preferred radical definitions apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another at will, i.e. including combinations between the given preferred ranges. [0058]
  • Preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being preferred (“preferably”). [0059]
  • Particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings given above as being particularly preferred. [0060]
  • Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred. [0061]
  • Most preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings given above as being most preferred. [0062]
  • Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, are—including in combination with heteroatoms, such as in alkoxy—in each case straight-chain or branched as far as this is possible. [0063]
  • Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitution the substituents can be identical or different. [0064]
  • If the compounds of the general formula (I) according to the invention contain substituents with asymmetric carbon atoms, the invention relates in each case to the R enantiomers and the S enantiomers and to any mixures of these enantiomers, in particular the racemates. In the case of compounds of the formula (I) having alkenyl substituents, the invention relates in each case to the possible E and Z isomers and their mixtures. [0065]
  • Examples of the compounds of the general formula (I) according to the invention are listed in the groups below. [0066]
  • Group 1 [0067]
    Figure US20040029735A1-20040212-C00005
  • Here, Q, R[0068] 1, R2, R3, R4, R5 and Y each have the meanings given below in tabular form.
    Q R1 R2 R3 R4 R5 Y
    O H CF3 H F CN —
    O CH3 CF3 H F CN —
    S H CF3 H F CN —
    S CH3 CF3 H F CN —
    O H CF3 Cl F CN —
    O CH3 CF3 Cl F CN —
    O H CF3 CH3 F CN —
    O CH3 CF3 CH3 F CN —
    O H CF3 H F CN OH
    O CH3 CF3 H F CN OH
    O H CF3 H F CN OCH3
    O CH3 CF3 H F CN OCH3
    O H CN H F CN OCH3
    O CH3 CN H F CN OCH3
    O H CF3 H F Cl OCH3
    O CH3 CF3 H F Cl OCH3
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00006
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00007
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00008
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00009
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00010
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00011
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00012
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00013
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00014
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00015
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00016
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00017
    O H CF3 H F CN Cl
    O CH3 CF3 H F CN Cl
    S H CF3 H F CN Cl
    S CH3 CF3 H F CN Cl
    O H CF3 H F CN SH
    O CH3 CF3 H F CN SH
    O H CF3 H F CN NH2
    O CH3 CF3 H F CN NH2
    O H CF3 H Cl Cl OH
    O CH3 CF3 H Cl Cl OH
    O H CF3 H H CN OH
    O CH3 CF3 H H CN OH
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00018
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00019
    O H CF3 H F CN SCH3
    O CH3 CF3 H F CN SCH3
    O H CF3 H F CN SO3H
    O CH3 CF3 H F CN SO3H
    O H CF3 H F CN SO3Na
    O CH3 CF3 H F CN SO3Na
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00020
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00021
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00022
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00023
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00024
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00025
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00026
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00027
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00028
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00029
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00030
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00031
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00032
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00033
    O H CF3 H F CN COOH
    O CH3 CF3 H F CN COOH
    O H CF3 H F CN COOCH3
    O CH3 CF3 H F CN COOCH3
    O H CF3 H F CN COOC2H5
    O CH3 CF3 H F CN COOC2H5
    O H CF3 H F CN CH3
    O CH3 CF3 H F CN CH3
    O H CF3 H F CN CH2Cl
    O CH3 CF3 H F CN CH2Cl
    O H CF3 H F CN CH2Br
    O CH3 CF3 H F CN CH2Br
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00034
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00035
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00036
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00037
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00038
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00039
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00040
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00041
    O H CF3 H F CN COOC3H7-i
    O CH3 CF3 H F CN COOC3H7-i
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00042
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00043
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00044
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00045
    O H CF3 H F CN
    Figure US20040029735A1-20040212-C00046
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00047
    O H CF3 H F Cl
    Figure US20040029735A1-20040212-C00048
    O CH3 CF3 H F Cl
    Figure US20040029735A1-20040212-C00049
    O H CF3 H F Br
    Figure US20040029735A1-20040212-C00050
    O CH3 CF3 H F Br
    Figure US20040029735A1-20040212-C00051
    O CH3 CF3 H F
    Figure US20040029735A1-20040212-C00052
    Figure US20040029735A1-20040212-C00053
    O CH3 CF3 H F
    Figure US20040029735A1-20040212-C00054
    Figure US20040029735A1-20040212-C00055
    O CH3 CF3 H F
    Figure US20040029735A1-20040212-C00056
    Figure US20040029735A1-20040212-C00057
    O CH3 CF3 H F
    Figure US20040029735A1-20040212-C00058
    Figure US20040029735A1-20040212-C00059
    O CH3 CN H F CN
    Figure US20040029735A1-20040212-C00060
    O CH3 CN H F CN
    Figure US20040029735A1-20040212-C00061
    O CH3 CF3 H Cl Cl
    Figure US20040029735A1-20040212-C00062
    O CH3 CF3 H Cl Cl
    Figure US20040029735A1-20040212-C00063
    O NH2 CF3 H F CN
    Figure US20040029735A1-20040212-C00064
    O NH2 CF3 H F CN
    Figure US20040029735A1-20040212-C00065
    O CH3 CHF2 H F CN OH
    O CH3 CHF2 H F CN
    Figure US20040029735A1-20040212-C00066
    O CH3 CF2Cl H F CN OH
    O CH3 CF2Cl H F CN
    Figure US20040029735A1-20040212-C00067
    O CH3 C2F5 H F CN OH
    O CH3 C2F5 H F CN
    Figure US20040029735A1-20040212-C00068
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00069
    O CH3 CF3 H F CN CHO
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00070
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00071
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00072
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00073
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00074
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00075
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00076
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00077
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00078
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00079
    O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00080
    O CH3 CF3 Cl F CN
    Figure US20040029735A1-20040212-C00081
  • Group 2 [0069]
    Figure US20040029735A1-20040212-C00082
  • Here, Q, R[0070] 1, R2, R3, R4, R5 and Y each have the meanings given above in group 1 in tabular form.
  • Group 3 [0071]
    Figure US20040029735A1-20040212-C00083
  • Here, Q, R[0072] 1, R2, R3, R4, R5 and Y each have the meanings given above in group 1 in tabular form.
  • Group 4 [0073]
    Figure US20040029735A1-20040212-C00084
  • Here, Q, R[0074] 1, R2, R3, R4, R5 and Y each have the meanings given above in group 1 in tabular form.
  • Group 5 [0075]
    Figure US20040029735A1-20040212-C00085
  • Here, Q, R[0076] 1, R2, R3, R4, R5 and Y each have the meanings given above in group 1 in tabular form.
  • Group 6 [0077]
    Figure US20040029735A1-20040212-C00086
  • Here, Q, R[0078] 1, R2, R3, R4, R5 and Y each have the meanings given above in group 1 in tabular form.
  • Group 7 [0079]
    Figure US20040029735A1-20040212-C00087
  • Here, Q, R[0080] 1, R2, R3, R4, R5 and Y each have the meanings given above in group 1 in tabular form.
  • Group 8 [0081]
    Figure US20040029735A1-20040212-C00088
  • Here, Q, R[0082] 1, R2, R3, R4 and R5 have the meanings given above in Group 1 in tabular form; X has the meanings given above in Group 1 for Y.
  • The novel substituted phenyluracils of the general formula (I) have interesting biological properties. In particular, they have strong herbicidal activity. [0083]
  • The novel substituted phenyluracils of the general formula(I) are obtained when [0084]
  • (a) halogenophenyluracils of the general formula (II) [0085]
    Figure US20040029735A1-20040212-C00089
  • in which [0086]
  • R[0087] 1, R2, R3, R4 and R5 are each as defined above and
  • X[0088] 1 represents halogen,
  • are reacted with naphthalene derivatives of the general formula (III) [0089]
    Figure US20040029735A1-20040212-C00090
  • in which [0090]
  • m, n, Q, X und Y are each as defined above, [0091]
  • or with alkali metal salts of compounds of the formula (III)- [0092]
  • if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, [0093]
  • or when [0094]
  • (b) aminoalkenoic acid esters of the general formula (IV) [0095]
    Figure US20040029735A1-20040212-C00091
  • in which [0096]
  • R[0097] 2 and R3 are each as defined above and
  • R represents alkyl, aryl or arylalkyl, [0098]
  • are reacted with aryl isocyanates of the general formula (V) [0099]
    Figure US20040029735A1-20040212-C00092
  • in which [0100]
  • m, n, Q, R[0101] 4, R5, X and Y are as defined above,
  • or with arylurethanes (arylcarbamates) of the general formula (VI) [0102]
    Figure US20040029735A1-20040212-C00093
  • in which [0103]
  • m, n, Q, R[0104] 4, R5, X and Y are as defined above and
  • R represents alkyl, aryl or arylalkyl, [0105]
  • if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, [0106]
  • or when [0107]
  • (c) N-aryl-1-alkoxycarbonylamino-maleimides of the general formula (VII) [0108]
    Figure US20040029735A1-20040212-C00094
  • in which [0109]
  • m, n, Q, R[0110] 3, R4, R5, X and Y are as defined above and
  • R′ represents alkyl, [0111]
  • are reacted with a metal hydride in the presence of water and, if appropriate, in the presence of an organic solvent, [0112]
  • or when [0113]
  • (d) substituted phenyluracils of the general formula (Ia) [0114]
    Figure US20040029735A1-20040212-C00095
  • in which [0115]
  • m, n, Q, R[0116] 2, R3, R4, R5, X and Y are as defined above,
  • are reacted with 1-aminooxy-2,4-dinitro-benzene or with alkylating agents of the general formula (VIII)[0117]
  • X2—A1  (VIII)
  • in which [0118]
  • A[0119] 1 represents optionally substituted alkyl and
  • X[0120] 2 represents halogen or the grouping —O—SO2—O—A1,
  • if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, [0121]
  • and electrophilic or nucleophilic and/or oxidation or reduction reactions within the scope of the definition of the substituents are, if appropriate, subsequently carried out in a customary manner. [0122]
  • The compounds of the general formula (I) can be converted by customary methods into other compounds of the general formula (I) according to the above definition, for example by etherification or ether cleavage (X,Y: OH→OC[0123] 2H5, OCH3→OH), esterification or hydrolysis (for example X: OCH2COOH→OCH2COOC2H5, OCH(CH3)COOCH3→OCH(CH3)COOH), reaction with dicyano or hydrogen sulphide (for example R5: Br→CN, CN→CSNH2), conversion of carboxyl compounds into other carboxylic acid derivatives by customary methods (for example R2: COOH→CN, COOH→COOCH3), conversion of sulfonic acid derivatives according to customary methods (for example X,Y: SO3Na→SO2Cl, SO2Cl→SH), halogenation (for example X,Y: CH3→CH2Cl or CH2Br)—cf. the Preparation Examples.
  • Using, for example, 1-(4-cyano-2,5-difluoro-phenyl)-4-chlorodifluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine and 5-methoxy-1-naphthol as starting materials, the course of the reaction of process (a) according to the invention can be illustrated by the following formula scheme: [0124]
    Figure US20040029735A1-20040212-C00096
  • Using, for example, methyl 3-amino-4,4,4-trifluoro-crotonate and 4-cyano-2-fluoro-5-(2-naphthyloxy)-phenyl isocyanate as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following scheme: [0125]
    Figure US20040029735A1-20040212-C00097
  • Using, for example, methyl [1-(2,4-dichloro-5-(1-naphthylthio)-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-carbamate as starting material, the course of the reaction in the process (c) according to the invention can be illustrated by the following formula scheme: [0126]
    Figure US20040029735A1-20040212-C00098
  • Using, for example, 1-[2-chloro-4-trifluoromethyl-5-(6-methoxycarbonylmethoxy-2-naphthyloxy)-phenyl]-4-difluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine and methyl bromide as starting materials, the course of the reaction in the process (d) according to the invention can be illustrated by the following formula scheme: [0127]
    Figure US20040029735A1-20040212-C00099
  • The formula (II) provides a general definition of the halogenophenyluracils to be used as starting materials in the process (a) according to the invention for preparing compounds of the formula (I). In the formula (II), R[0128] 1, R2, R3, R4 and R5 each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for R1, R2, R3, R4 and R5; X1 preferably represents fluorine or chlorine, in particular fluorine.
  • The starting materials of the general formula (II) are known and/or can be prepared by processes known per se (cf. EP-A-648749). [0129]
  • The formula (III) provides a general definition of the naphthalene derivatives further to be used as starting materials in the process (a) according to the invention. In the formula (III), m, n, Q, X and Y each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for m, n, Q, X and Y. [0130]
  • The starting materials of the general formula (III) are known organic chemicals for synthesis. [0131]
  • The formula (IV) provides a general definition of the aminoalkenoic acid esters to be used as starting materials in the process (b) according to the invention for preparing compounds of the general formula (I). In the general formula (IV), R[0132] 2 and R3 each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for R2 and R3; R preferably represents C1-C4-alkyl, phenyl or benzyl, in particular methyl or ethyl.
  • The starting materials of the general formula (IV) are known and/or can be prepared by processes known per se (cf. J. Heterocycl. Chem. 9 (1972), 513-522). [0133]
  • Formula (V) provides a general definition of the aryl isocyanates further to be used as starting materials in the process (b) according to the invention. In the general formula (V), m, n, Q, R[0134] 4, R5, X and Y each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for m, n, Q, R4, R5, X and Y.
  • The starting materials of the general formula (V) have hitherto not been disclosed in the literature; as novel compounds, they also form part of the subject-matter of the present application. [0135]
  • The novel aryl isocyanates of the general formula (V) are obtained by reacting aniline derivatives of the general formula (IX) [0136]
    Figure US20040029735A1-20040212-C00100
  • in which [0137]
  • m, n, Q, R[0138] 4, R5, X and Y are each as defined above
  • with phosgene in the presence of a diluent, such as, for example, chlorobenzene, at temperatures between −20° C. and +150° C. (cf., for example, also EP-A-648749). [0139]
  • The formula (VI) provides a general definition of the arylurethanes to be used, if appropriate, as starting materials in the process (b) according to the invention. In the general formula (VI), m, n, Q, R[0140] 4, R5, X and Y each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for m, n, Q, R4, R5, X and Y; R preferably represents C1-C4-alkyl, phenyl or benzyl, in particular methyl or ethyl.
  • The starting materials of the general formula (VI) have hitherto not been disclosed in the literature; as novel compounds, they also form part of the subject-matter of the present application. [0141]
  • The novel arylurethanes of the general formula (VI) are obtained by reacting aniline derivatives of the general formula (IX) [0142]
    Figure US20040029735A1-20040212-C00101
  • in which [0143]
  • m, n, Q, R[0144] 4, R5, X and Y are each as defined above,
  • with chlorocarbonyl compounds of the general formula (X)[0145]
  • RO—CO—Cl  (X)
  • in which [0146]
  • R is as defined above, [0147]
  • if appropriate in the presence of an acid acceptor, such as, for example, pyridine, and if appropriate in the presence of a diluent, such as, for example, methylene chloride, at temperatures between −20° C. and +100° C. (cf. the Preparation Examples). [0148]
  • The aniline derivatives of the general formula (IX) required as precursors have hitherto not been disclosed in the literature; as novel compounds, they also form part of the subject-matter of the present application. [0149]
  • The novel aniline derivatives of the general formula (IX) are obtained by reacting anilines of the general formula (XI) [0150]
    Figure US20040029735A1-20040212-C00102
  • in which [0151]
  • R[0152] 4, R5 and X1 are each as defined above,
  • with naphthalene derivatives of the general formula (III) [0153]
    Figure US20040029735A1-20040212-C00103
  • in which [0154]
  • m, n, Q, X and Y are each as defined above, [0155]
  • or with alkali metal salts of compounds of the formula (III)- [0156]
  • if appropriate in the presence of a reaction auxiliary, such as, for example, sodium hydride, and if appropriate in the presence of a diluent, such as, for example, N-methyl-pyrrolidone, at temperatures between 0° C. and 150° C. (cf. the Preparation Examples). [0157]
  • The formula (VII) provides a general definition of the N-aryl-1-alkoxycarbonylamino-maleimides to be used as starting materials in the process (c) according to the invention for preparing compounds of the general formula (I). In the general formula (VII), m, n, Q, R[0158] 3, R4, R5, X and Y each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred, very particulaly preferred or most preferred for m, n, Q, R3, R4, R5, X and Y; R′ preferably represents C1-C4-alkyl, in particular methyl or ethyl.
  • The novel N-aryl-1-alkoxycarbonylamino-maleimides of the general formula (VII) are obtained by reacting alkyl (2,5-dioxo-2,5-dihydro-furan-3-yl)-carbamates of the general formula (XII) [0159]
    Figure US20040029735A1-20040212-C00104
  • in which [0160]
  • R[0161] 3 is as defined above and
  • R′ represents alkyl, (in particular methyl or ethyl), [0162]
  • with aniline derivatives of the general formula (IX) [0163]
    Figure US20040029735A1-20040212-C00105
  • in which [0164]
  • m, n, Q, R[0165] 4, R5, X and Y are each as defined above,
  • if appropriate in the presence of a diluent, such as, for example, acetic acid, at temperatures between 0° C. and 200° C., preferably between 50° C. and 150° C. [0166]
  • The precursors of the general formula (XII) are known and/or can be prepared by processes known per se (cf. DE 19604229). [0167]
  • The formula (Ia) provides a general definition of the substituted phenyluracils to be used as starting materials in the process (d) according to the invention for preparing compounds of the formula (I). In the formula (Ia), m, n, Q, R[0168] 2, R3, R4, R5, X and Y each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for m, n, Q, R2, R3, R4, R5, X and Y.
  • As novel substances, the starting materials of the general formula (Ia) for process (b) also form part of the subject-matter of the present application; they can be prepared according to processes (a), (b) and (c) according to the invention. [0169]
  • The formula (VIII) provides a general definition of the alkylating agents further to be used as starting materials in the process (d) according to the invention. In the formula (VIII), A[0170] 1 preferably represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl having 1 to 4 carbon atoms and X2 represents chlorine, bromine, iodine, methylsulphonyloxy or ethylsulphonyloxy; A1 particularly preferably represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl and X2 represents chlorine, bromine, iodine, methylsulphonyloxy or ethylsulphonyloxy.
  • The starting materials of the formula (VIII) are known organic chemicals for synthesis. [0171]
  • The processes according to the invention for preparing the compounds of the general formula (I) are preferably carried out using diluents. Suitable diluents for carrying out the processes (a), (b), (c) and (d) according to the invention are, in addition to water, especially inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate, sulphoxides, such as dimethyl sulphoxide, alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water or pure water. [0172]
  • Suitable reaction auxiliaries for the processes (a), (b), (c) and (d) according to the invention are, in general, the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, such as, for example, sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide, or potassium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N,N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N,N-dimethyl-aniline, N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo[2.2.2]-octane (DABCO), 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU). [0173]
  • Other suitable reaction auxiliaries for the processes according to the invention are phase-transfer catalysts. Examples of such catalysts which may be mentioned are: [0174]
  • Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulphate, methyl-trioctylammonium chloride, hexadecyl-trimethylammonium chloride, hexadecyl-trimethylammonium bromide, benzyl-trimethylammonium chloride, benzyl-triethylammonium chloride, benzyl-trimethylammonium hydroxide, benzyl-triethylammonium hydroxide, benzyl-tributylammonium chloride, benzyl-tributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributyl-hexadecylphosphonium bromide, butyl-triphenylphosphonium chloride, ethyl-trioctylphosphonium bromide, tetraphenylphosphonium bromide. [0175]
  • When carrying out the processes (a), (b), (c) and (d) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the processes are carried out at temperatures between 0° C. and 150° C., preferably between 10° C. and 120° C. [0176]
  • The processes according to the invention are generally carried out under atmospheric pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure—in general between 0.1 bar and 10 bar. [0177]
  • For carrying out the process according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible for one of the components to be used in a relatively large excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for several hours. Work-up is carried out by customary methods (cf. the Preparation Examples). [0178]
  • The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed killers. By weeds in the broadest sense there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used. [0179]
  • The active compounds according to the invention can be used, for example, in connection with the following plants: [0180]
  • Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. [0181]
  • Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia. [0182]
  • Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. [0183]
  • Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea. [0184]
  • However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants. [0185]
  • Depending on the concentration, the active compounds according to the invention are suitable for total weed control, for example on industrial terrain and railway tracks and on paths and areas with or without tree growth. Equally, the active compounds according to the invention can be employed for controlling weeds in perennial crops, for example forests, ornamental tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns and turf and pastures and for selective weed control in annual crops. [0186]
  • The active compounds of the formula (I) according to the invention have strong herbicidal activity and a broad activity spectrum when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both by the pre-emergence and by the post-emergence method. [0187]
  • The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic substances impregnated with active compound, and microencapsulations in polymeric substances. [0188]
  • These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is to say liquid solvents and/or solid carriers, optionally with the use of surfactants, that is to say emulsifiers and/or dispersants and/or foam formers. [0189]
  • If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Liquid solvents which are mainly suitable are: 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 also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and water. [0190]
  • Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic meals, and granules of organic material, such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyetliylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates and protein hydrolysates; suitable dispersants are: for example lignosulphite waste liquors and methylcellulose. [0191]
  • Tackifiers, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils. [0192]
  • It is possible to use dyestuffs, such as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. [0193]
  • The formulations generally comprise between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%. [0194]
  • For controlling weeds, the active compounds according to the invention, as such or in their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible. [0195]
  • Possible components for the mixtures are known herbicides, for example [0196]
  • acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl), benfuresate, bensulfuron(-methyl), bentazone, benzobicyclon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl), chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlorotoluron, cinidon(-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron; cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-(-P-ethyl), fentrazamide, flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl), flazasulfron, florasulam, fluazifop(-P-butyl), fluazolate, flucarbazone, flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam, flupropacil, flurpyrsulfuron(-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr(-meptyl), flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen, glufosinate(-ammonium), glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl), haloxyfop(-P-methyl), hexazinone, imazamethabenz-(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron(-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor, metosulam, metoxuron, metribuzin, metsulfuron(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac-(-methyl), pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron. [0197]
  • A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, is also possible. [0198]
  • The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering. [0199]
  • The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing. [0200]
  • The amount of active compound used can vary within a relatively wide range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha. [0201]
  • The preparation and the use of the active compounds according to the invention can be seen from the examples below. [0202]
    • PREPARATION EXAMPLES Example 1
  • [0203]
    Figure US20040029735A1-20040212-C00106
  • (Process (a)) [0204]
  • 4.04 g (25 mmol) of 1,5-dihydroxy-naphthalene are initially charged in 100 ml of dimethyl sulphoxide and admixed with 2.5 g (25 mmol) of sodium hydride (60%), and the mixture is stirred for 30 minutes. 8.0 g (25 mmol) of 1-(4-cyano-2,5-difluoro-phenyl)-4-trifluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine are then added and the reaction mixture is stirred at from 60° C. to 70° C. for 20 hours and then poured into about the same amount of 2N hydrochloric acid. The resulting crystalline product is isolated by filtration with suction and purified by column chromatography (silica gel, chloroform/ethyl acetate, vol. 1:1). [0205]
  • This gives (as second fraction) 2.9 g (25% of theory) of 4-(2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-5-fluoro-2-(5-hydroxy-1-naphthyloxy)-benzonitrile of melting point 168° C. [0206]
    • Example 2
  • [0207]
    Figure US20040029735A1-20040212-C00107
  • (Process (d) with Subsequent Reaction) [0208]
  • A mixture of 32.6 g (71 mmol) of 4-(2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-5-fluoro-2-(5-hydroxy-1-naphthyloxy)-benzonitrile (cf. Example 1), 19.8 g (71 mmol) of dimethyl sulphate, 21.7 g (71 mmol) of potassium carbonate and 200 ml of acetone is stirred and heated under reflux for 20 hours. After cooling to room temperature, the mixture is concentrated under water-pump vacuum, the residue is shaken with ethyl acetate/1N hydrochloric acid and the organic phase is separated off, washed with water, dried with sodium sulphate and filtered. The filtrate is concentrated under water-pump vacuum, the residue is digested with diethyl ether/petroleum ether and the resulting crystalline product is isolated by filtration with suction and purified by column chromatography (silica gel, chloroform/ethyl acetate, vol. 3:1). [0209]
  • This gives (as first fraction) 5-fluoro-2-(5-methoxy-1-naphthyloxy)-4-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-benzonitrile of melting point 109° C. [0210]
    • Example 3
  • [0211]
    Figure US20040029735A1-20040212-C00108
  • (Process (a)) [0212]
  • 3.63 g (25 mmol) of 2-naphthol are initially charged in 100 ml of dimethyl sulphoxide and admixed with 2.5 g (25 mmol) of sodium hydride (60%), and the mixture is stirred for 30 minutes. 8.0 g (25 mmol) of 1-(4-cyano-2,5-difluorophenyl)-4-trifluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine are then added and the reaction mixture is stirred at from 60° C. to 70° C. for 20 hours and then poured into about the same amount of 2N hydrochloric acid. The resulting crystalline product is isolated by filtration with suction. [0213]
  • This gives 9.6 g (86% of theory) of 4-(2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-5-fluoro-2-(2-naphthyloxy)benzonitrile of melting point 92° C. [0214]
    • Example 4
  • [0215]
    Figure US20040029735A1-20040212-C00109
  • (Subsequent Reaction) [0216]
  • A mixture of 2.7 g (5.91 mmol) of 4-(2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-5-fluoro-2-(6-hydroxy-2-naphthyloxy)benzonitrile, 0.89 g (5.91 mmol) of dimethyl sulphate, 0.98 g (5.91 mmol) of potassium carbonate and 100 ml of acetone is stirred and heated under reflux for 20 hours. After cooling to room temperature, the mixture is concentrated under water-pump vacuum, the residue is shaken with ethyl acetate/1N hydrochloric acid and the organic phase is separated off, washed with water, dried with sodium sulphate and filtered. The residue is digested with diethyl ether/petroleum ether and the resulting crystalline product is isolated by filtration with suction and purified by column chromatography (silica gel, chloroform/ethyl acetate, vol. 2:1). [0217]
  • This gives (as second fraction) 0.8 g (29% of theory) of 5-fluoro-2-(6-hydroxy-2-naphthyloxy)-4-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-benzonitrile of melting point 174° C. [0218]
    • Example 5
  • [0219]
    Figure US20040029735A1-20040212-C00110
  • (Subsequent Reaction) [0220]
  • A mixture of 0.25 g (0.53 mmol) of 5-fluoro-2-(7-hydroxy-2-naphthyloxy)-4-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-benzonitrile, 0.11 g (0.53 mmol) of ethyl 2-bromo-propanoate (racemic), 0.10 g (0.53 mmol) of potassium carbonate and 30 ml of acetonitrile is stirred and heated under reflux for 18 hours. After cooling to room temperature, the mixture is concentrated under water-pump vacuum, the residue is shaken with ethyl acetate/1N hydrochloric acid and the organic phase is separated off, washed with saturated aqueous sodium chloride solution, dried with sodium sulphate and filtered. The filtrate is concentrated under water-pump vacuum, the residue is digested with diethyl ether and the resulting crystalline product is isolated by filtration with suction. [0221]
  • This gives 0.15 g (50% of theory) of ethyl 2-[7-(2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl]-phenoxy)-2-naphthyloxy]-propanoate (racemate) of melting point 133° C. [0222]
    • Example 6
  • [0223]
    Figure US20040029735A1-20040212-C00111
  • (Subsequent Reaction) [0224]
  • A mixture of 0.35 g (0.74 mmol) of 5-fluoro-2-(6-hydroxy-2-naphthyloxy)-4-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl)-benzonitrile, 0.22 g (0.74 mmol) of ethyl (R)-2-(p-tolyl-sulphonyloxy)-propanoate, 0.13 g (0.74 mmol) of potassium carbonate and 30 ml of acetonitrile is stirred and heated under reflux for 20 hours. After cooling to room temperature, the mixture is concentrated under water-pump vacuum, the residue is shaken with ethyl acetate/1N hydrochloric acid and the organic phase is separated off, washed with saturated aqueous sodium chloride solution, dried with sodium sulphate and filtered. The filtrate is concentrated under water-pump vacuum and the residue is purified by column chromatography (silica gel, chloroform/ethyl acetate, vol. 2:1). [0225]
  • This gives 0.06 g (14% of theory) of ethyl (R)-2-[6-(2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-1(2H)-pyrimidinyl]-phenoxy)-2-naphthyloxy]-propanoate as an amorphous product (logP: 3.99 at pH 2.3) [0226]
  • Analogously to Examples 1 to 6 and in accordance with the general description of the preparation process according to the invention, it is also possible to prepare, for example, the compounds of the general formula (I) listed in the tables below. [0227]
    Figure US20040029735A1-20040212-C00112
    TABLE 1
    Examples of the compounds of the formula (I)
    All examples in Table 1 refer to compounds in which Q represents
    O (oxygen) and R3 represents H (hydrogen).
    Ex. No. Q R1 R2 R3 R4 R5
    Figure US20040029735A1-20040212-C00113
         		Physical Data
    7 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00114
         		m.p: 114° C.
    8 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00115
         		m.p.: 126° C. (racemate)
    9 O H CF3 H F CN
    Figure US20040029735A1-20040212-C00116
         		m.p.: 76° C.
    10 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00117
         		m.p.: 168° C.
    11 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00118
         		m.p.: 205° C.
    12 O H CF3 H F CN
    Figure US20040029735A1-20040212-C00119
         		m.p.: 275° C.
    13 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00120
         		m.p.: 161° C.
    14 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00121
         		m.p.: 136° C.
    15 O H CF3 H F CN
    Figure US20040029735A1-20040212-C00122
         		(amorphous)
    16 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00123
         		m.p. 152° C.
    17 O H CF3 H F CN
    Figure US20040029735A1-20040212-C00124
         		m.p.: 158° C.
    18 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00125
         		m.p.: 142° C.
    19 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00126
         		m.p.: 130° C.
    20 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00127
         		m.p.: 152° C.
    21 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00128
    22 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00129
    23 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00130
         		m.p.: 164° C.
    24 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00131
    25 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00132
    26 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00133
         		m.p.: 225° C.
    27 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00134
         		m.p.: 151° C. (racemate)
    28 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00135
    29 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00136
         		(R enantiomer)
    30 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00137
         		m.p.: 155° C.
    31 O H
    Figure US20040029735A1-20040212-C00138
         		H F CN
    Figure US20040029735A1-20040212-C00139
         		logP = 2.11a)
    32 O H
    Figure US20040029735A1-20040212-C00140
         		H F CN
    Figure US20040029735A1-20040212-C00141
         		logP = 2.13a)
    33 O CH3
    Figure US20040029735A1-20040212-C00142
         		H F CN
    Figure US20040029735A1-20040212-C00143
         		logP = 3.22a)
    34 O CH3
    Figure US20040029735A1-20040212-C00144
         		H F CN
    Figure US20040029735A1-20040212-C00145
         		logP = 3.26a)
    35 O CH3
    Figure US20040029735A1-20040212-C00146
         		H F CN
    Figure US20040029735A1-20040212-C00147
         		logP = 2.06a)
    36 O H CF3 H F CN
    Figure US20040029735A1-20040212-C00148
         		m.p.: 156° C.
    37 O H CF3 H F CN
    Figure US20040029735A1-20040212-C00149
         		m.p.: 118° C.
    38 O H CF3 H F CN
    Figure US20040029735A1-20040212-C00150
         		m.p.: 96° C.
    39 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00151
         		m.p.: 144° C.
    40 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00152
         		m.p.: 131° C.
    41 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00153
         		m.p.: 134° C.
    42 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00154
         		m.p.: 164° C.
    43 O CH3 CF3 H F CN
    Figure US20040029735A1-20040212-C00155
         		m.p.: 118° C.
    44 O CH3 CN H F CN
    Figure US20040029735A1-20040212-C00156
         		logP = 3.21a)
    45 O CH3
    Figure US20040029735A1-20040212-C00157
         		H F CN
    Figure US20040029735A1-20040212-C00158
         		logP = 2.43a)
    46 O CH3 CN H F CN
    Figure US20040029735A1-20040212-C00159
         		logP = 2.24a)
  • The logP values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using a reversed-phase column (C 18). Temperature: 43° C. [0228]
  • (a) Mobile phases for the determination in the acidic range: 0.1% aqeuous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile—the corresponding test results in Table 1 are labelled a). [0229]
  • (b) Mobile phases for the determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile—the corresponding test results in Table 1 are labelled b). [0230]
  • Calibration was carried out using unbranched alkan-2-ones (having 3 to 16 carbon atoms) with known logP values (determination of the logP values by the retention times using linear interpolation between two successive alkanones). [0231]
  • The lambda-max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals. [0232]
  • The compound listed above in Table 1 as Example 31 can be prepared, for example, as follows: [0233]
    Figure US20040029735A1-20040212-C00160
  • 13.0 g (27.4 mmol) of ethyl [1-(4-cyano-2-fluoro-5-(6-methoxy-naphthalen-2-yl-oxy)-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-carbamate are dissolved in 200 ml of 1,4-dioxane, and a solution of 1.2 g (30 mmol) of sodium hydroxide in 40 ml of water is added dropwise with stirring at room temperature (about 20° C.). The reaction mixture is then stirred at 90° C. for 4 hours and subsequently concentrated under water-pump vacuum. The residue is taken up in 800 ml of water and acidified using conc. hydrochloric acid. The resulting crystalline product is isolated by filtration with suction. [0234]
  • This gives 11.8 g (96% of theory) of 1-[4-cyano-2-fluoro-5-(6-methoxy-naphthalen-2-yl-oxy)-phenyl]-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid. [0235]
  • The compound listed above in Table 1 as Example 33 can be prepared, for example, as follows: [0236]
    Figure US20040029735A1-20040212-C00161
  • 11.5 g (25.7 mmol) of 1-[4-cyano-2-fluoro-5-(6-methoxy-naphthalen-2-yl-oxy)-phenyl]-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid are initially charged in 200 ml of acetone and admixed with 7.8 g (56 mmol) of potassium carbonate. At room temperature (about 20° C.), a solution of 8.1 g (64 mmol) of dimethyl sulphate in 20 ml of acetone is then added dropwise with stirring, and the reaction mixture is heated under reflux for 4 hours. The mixture is subsequently concentrated under water-pump vacuum, the residue is taken up in 600 ml of water and acidified with conc. hydrochloric acid and the resulting crystalline product is isolated by filtration with suction. [0237]
  • This gives 11 g (90% of theory) of methyl 1-[4-cyano-2-fluoro-5-(6-methoxy-naphthalen-2-yl-oxy)-phenyl]-2,6-dioxo-3-methyl-1,2,3,6-tetrahydro-pyrimidine-4-carboxylate. [0238]
  • The compound listed above in Table 1 as Example 35 can be prepared, for example, as follows: [0239]
    Figure US20040029735A1-20040212-C00162
  • 10.7 g (22.5 mmol) of methyl 1-[4-cyano-2-fluoro-5-(6-methoxy-naphthalen-2-yl-oxy)-phenyl]-2,6-dioxo-3-methyl-1,2,3,6-tetrahydro-pyrimidine-4-carboxylate are dissolved in 200 ml of tetrahydrofuran and admixed successively with 10.3 g of ammonium chloride and a 25% strength aqueous ammonia solution. The reaction mixture is stirred at room temperature (about 20° C.) for 12 hours and subsequently concentrated under water-pump vacuum. The residue is stirred with hexane and the crystalline product is isolated by filtration with suction. [0240]
  • This gives 9.4 g (91% of theory) of 1-[4-cyano-2-fluoro-5-(6-methoxy-naphthalen-2-yl-oxy)-phenyl]-2,6-dioxo-3-methyl-1,2,3,6-tetrahydro-pyrimidine-4-carboxamide. [0241]
  • Precursors of the Formula (VI): [0242]
    • Example (VI-1)
  • [0243]
    Figure US20040029735A1-20040212-C00163
  • 2.0 g (7.2 mmol) of 4-amino-5-fluoro-2-(2-naphthyloxy)-benzonitrile are initially charged in 100 ml of acetone and, at 40° C., admixed dropwise with stirring with 1.78 g (7.2 mmol) of trichloromethyl chloroformate (“diphosgene”). The reaction mixture is stirred at 40° C. for 4 hours and then added dropwise with stirring to 100 ml of ethanol. The mixture is then stirred at room temperature (about 20° C.) for 15 minutes and subsequently concentrated under water-pump vacuum. The residue is stirred with diethyl ether/petroleum ether and the resulting crystalline product is isolated by filtration with suction. [0244]
  • This gives 0.4 g (16% of theory) of O-ethyl N-[4-cyano-2-fluoro-5-(2-naphthyloxy)-phenyl]-carbamate of melting point 132° C. [0245]
  • Precursors of the Formula (VII): [0246]
    • Example (VII-1)
  • [0247]
    Figure US20040029735A1-20040212-C00164
  • A mixture of 15.0 g (48.7 mmol) of 4-amino-5-fluoro-2-(6-methoxy-naphthalen-2-yl-oxy)-benzonitrile, 10.8 g (58 mmol) of ethyl (2,5-dioxo-2,5-dihydro-furan-3-yl)-carbamate and 200 ml of acetic acid is heated under reflux for 4 hours and subsequently concentrated under water-pump vacuum. The residue is stirred with water and the crystalline product is isolated by filtration with suction and purified by column chromatography (silica gel, methylene chloride/ethyl acetate, vol. 95/5). [0248]
  • This gives 13.5 g (58% of theory) of ethyl [1-(4-cyano-2-fluoro-5-(6-methoxy-naphthalen-2-yl-oxy)-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-carbamate. logP=3.63[0249] a)
  • Analogously to Example (VII-I), it is also possible to prepare, for example, the compounds of the general formula (VII) listed in Table 2 below. [0250]
    Figure US20040029735A1-20040212-C00165
    TABLE 2
    Examples of the compounds of the formula (VII)
    Ex. No. Q R′ R3 R4 R5
    Figure US20040029735A1-20040212-C00166
         		Physical Data
    VII-2 O C2H5 H F CN
    Figure US20040029735A1-20040212-C00167
         		logP = 3.67a)
    VII-2 O C2H5 H F CN
    Figure US20040029735A1-20040212-C00168
    VII-3 O C2H5 H F CN
    Figure US20040029735A1-20040212-C00169
    VII-4 O C2H5 H F CN
    Figure US20040029735A1-20040212-C00170
  • Precursors of the formula (IX): [0251]
    • Example (IX-1)
  • [0252]
    Figure US20040029735A1-20040212-C00171
  • 3.93 g (26 mmol) of 2-naphthol are initially charged in 150 ml of N-methyl-pyrrolidone and mixed with 1.25 g (26 mmol) of sodium hydride (60%), and the mixture is stirred at room temperature (about 20° C.) for 30 minutes and then admixed with 4.0 g (26 mmol) of 4-amino-2,5-difluoro-benzonitrile and stirred at from 105° C. to 115° C. for two days. After cooling to room temperature, the mixture is poured into about the same amount of 2N hydrochloric acid, stirred for 15 minutes and extracted with ethyl acetate. The organic phase is washed with water, dried with sodium sulphate and filtered. The filtrate is concentrated under water-pump vacuum, the residue is digested with diethyl ether/petroleum ether and the crystalline product is isolated by filtration with suction and purified by column chromatography (silica gel, chloroform/ethyl acetate, vol. 4:1). [0253]
  • This gives 1.0 g (14% of theory) of 4-amino-5-fluoro-2-(2-naphthyloxy)-benzonitnile of melting point 89° C. [0254]
  • Analogously to Example (IX-1), it is also possible to prepare, for example, the compounds of the general formula (IX) listed in Table 3 below. [0255]
    Figure US20040029735A1-20040212-C00172
    TABLE 3
    Examples of the compounds of the formula (IX)
    Ex. No. Q R4 R5
    Figure US20040029735A1-20040212-C00173
         		Physical Data
    IX-2 O F CN
    Figure US20040029735A1-20040212-C00174
         		1H-NMR (D6-DMSO, δ): 8.03, 8.06 ppm
    IX-3 O F CN
    Figure US20040029735A1-20040212-C00175
         		m.p.: 130° C.
    IX-4 O F CN
    Figure US20040029735A1-20040212-C00176
         		m.p.: 144° C.
    • Use Examples Example A
  • Pre-Emergence Test [0256]
  • Solvent: 5 parts by weight of acetone [0257]
  • Emulsifier: 1 part by weight of alkylaryl polyglycol ether [0258]
  • To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration. [0259]
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the preparation of active compound such that the particular amount of active compound desired is applied per unit area. The concentration of the spray liquor is chosen so that the particular amount of active compound desired is applied in 1000 litres of water per hectare. [0260]
  • After three weeks the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. [0261]
  • The figures denote: [0262]
  • 0%=no effect (like untreated control) [0263]
  • 100%=total destruction [0264]
  • In this test, for example, the compounds of Preparation Examples 7, 8, 10, 11 and 13 exhibit strong activity against weeds, and some of them are tolerated well by crop plants, such as, for example, maize. [0265]
    • Example B
  • Post-Emergence Test [0266]
    Solvent: 5 parts by weight of acetone
    Emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration. [0267]
  • Test plants of a height of 5-15 cm are sprayed with the preparation of active compound such that the particular amounts of active compound desired are applied per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 1000 1 of water/ha. [0268]
  • After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. [0269]
  • The figures denote: [0270]
  • 0%=no effect (like untreated control) [0271]
  • 100%=total destruction [0272]
  • In this test, for example, the compounds of Preparation Examples 7, 8, 10, 11 and 13 exhibit strong activity against weeds. [0273]

Claims (15)

1. Substituted phenyluracils of the general formula (I)
Figure US20040029735A1-20040212-C00177
in which
m represents 0, 1, 2 or 3,
n represents 0, 1, 2, 3 or 4,
Q represents O (oxygen), S (sulphur), SO, SO2, NH or N(alkyl),
R1 represents hydrogen, amino or optionally substituted alkyl,
R2 represents carboxyl, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted alkyl or alkoxycarbonyl,
R3 represents hydrogen, halogen or optionally substituted alkyl,
R4 represents hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,
R5 represents cyano, carbamoyl, thiocarbamoyl, halogen or in each case optionally substituted alkyl or alkoxy,
X represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaininocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl, alkinylcarbonyloxy or arylcarbonyloxy, and
Y represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsuipholnylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl, alkinylcarbonyloxy or arylcarbonyloxy,
where, in the case that m and/or are greater than 1, X and Y in the individual compounds possible in each case have identical or different meanings from those given,
and salts of compounds of the formula (I).
2. Compounds according to claim 1 characterized in that
m represents 0, 1 or 2,
n represents 0, 1, 2 or 3,
Q represents O (oxygen), S (sulphur), SO, SO2, NH or N(C1-C4-alkyl),
R1 represents hydrogen, amino or represents optionally cyano-, halogen- or C1-C3-alkoxy-substituted alkyl having 1 to 4 carbon atoms,
R2 represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, halogen- or C1-C3-alkoxy-substituted alkyl or alkoxycarbonyl having in each case 1 to 4 carbon atoms,
R3 represents hydrogen, halogen or represents optionally cyano-, halogen- or C1-C3-alkoxy-substituted alkyl having 1 to 4 carbon atoms,
R4 represents hydrogen, cyano, fluorine or chlorine,
R5 represents cyano, carbamoyl, thiocarbamoyl, halogen or represents in each case optionally halogen-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms,
X represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-, C1-C4-alkylsulphonyl-, C1-C4-alkyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C2-C4-alkenyloxy-carbonyl-, C2-C4-alkinyloxy-carbonyl-, C1-C4-alkylaminocarbonyl-, di-(C1-C4-alkyl)-amino-carbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6 carbon atoms, represents dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylamino-carbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, bis-alkylsulfonyl-amino or N-alkylcarbonyl-N-alkylsulphonyl-amino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C1-C4-alkoxy-carbonyl-, C1-C4-alkylamino-carbonyl- or di-(C1-C4-alkyl)-amino-carbonyl-substituted alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl or alkinylcarbonyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups, or represents benzyloxy, and
Y represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-, C1-C4-alkylsulphonyl-, C1-C4-alkyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C2-C4-alkenyloxy-carbonyl-, C2-C4-alkinyloxy-carbonyl-, aminocarbonyl-, C1-C4-alkylaminocarbonyl-, di-(C1-C4-alkyl)-aminocarbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6 carbon atoms, represents dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, bis-alkylsulfonyl-amino or N-alkylcarbonyl-N-alkylsulphonyl-amino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C1-C4-alkoxycarbonyl-, C1-C4-alkylaminocarbonyl- or di-(C1-C4-alkyl)-amino-carbonyl-substituted alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl or alkinylcarbonyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups, or represents benzyloxy.
3. Compounds according to claim 1 or 2, characterized in that
m represents 0 or 1,
n represents 0, 1 or 2,
Q represents O (oxygen) or S (sulphur),
R1 represents hydrogen, amino or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,
R2 represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,
R3 represents hydrogen, fluorine, chlorine, bromine, or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,
R4 represents hydrogen, fluorine or chlorine,
R5 represents cyano, carbarnoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,
X represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulphonyl, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbanoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, n-, i-, s- or t-butoxycarbonyl-, propenyloxycarbonyl-, butenyloxycarbonyl-, propinyloxycarbonyl-, butinyloxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsuliphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, represents dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-oder i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, n-, i-, s- or t-butoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, n-, i-, s- or t-butylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, or represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or diethylaminocarbonyl-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, ethenecarbonyloxy, propenecarbonyloxy, butenecarbonyloxy, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonyl, butinyloxycarbonyl, ethinecarbonyloxy, propinecarbonyloxy or butinecarbonyloxy, or represents benzoyloxy,
Y represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulphonyl, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, n-, i-, s- or t-butoxycarbonyl-, propenyloxycarbonyl-, butenyloxycarbonyl-, propinyloxycarbonyl-, butinyloxycarbonyl-, aminocarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, represents dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methylcarbonyloxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy, n- or i-butyroyloxy, methylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, n-, i-, s- or t-butoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, n-, i-, s- or t-butylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonyl amino, n- or i-propylsulphonylamino, or represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or diethylaminocarbonyl-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, ethenecarbonyloxy, propenecarbonyloxy, butenecarbonyloxy, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonyl, butinyloxycarbonyl, ethinecarbonyloxy, propinecarbonyloxy or butinecarbonyloxy, or represents benzoyloxy.
4. Compounds according to any of claims 1 to 3, characterized in that
m represents 0,
n represents 0 or 1,
Q represents O (oxygen),
R1 represents hydrogen, amino or methyl,
R2 represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, methoxycarbonyl or ethoxycarbonyl,
R3 represents hydrogen, fluorine, chlorine, bromine, or represents optionally fluorine- and/or chlorine-substituted methyl,
R4 represents fluorine,
R5 represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl or methoxy,
X represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulphonyl, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, propenyloxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or benzyloxycarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, represents dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-oder i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, or represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or diethylaminocarbonyl-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonyl or butinyloxycarbonyl, or represents benzoyloxy, and
Y represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulpho, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulfonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, propenyloxycarbonyl-, aminocarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, phenylaminocarbonyl- or benzyloxycarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n-oder i-propylamino, represents dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy, n- or i-butyroyloxy, methylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, or represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or diethylaminocarbonyl-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonyl or butinyloxycarbonyl, or represents benzoyloxy.
5. Compounds according to any of claims 1 to 4, characterized in that
R2 represents trifluoromethyl,
R3 represents hydrogen, and
R5 represents cyano.
6. Compounds according to any of claims 1 to 5, characterized in that
Q represents oxygen (O).
7. Compounds according to any of claims 1 to 5, characterized in that
Y represents hydroxyl, methoxy, represents in each case methoxycarbonyl-, ethoxycarbonyl-, methylaminocarbonyl-, dimethylaminocarbonyl- and phenylaminocarbonyl-substituted methoxy and ethoxy, represents methylaminocarbonyloxy, methylcarbonyloxy, propinyloxy, butinyloxy and ethoxycarbonyloxy.
8. Process for preparing compounds according to any of claims 1 to 7, characterized in that
(a) halogenophenyluracils of the general formula (II)
Figure US20040029735A1-20040212-C00178
in which
R1, R2, R3, R4 and R5 are each as defined in any of claims 1 to 5 and
X1 represents halogen,
are reacted with naphthalene derivatives of the general formula (III)
Figure US20040029735A1-20040212-C00179
in which
m, n, Q, X and Y are each as defined in any of claims 1 to 4, 6 and 7,
or with alkali metal salts of compounds of the formula (III)
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or that
(b) aminoalkenoic acid esters of the general formula (IV)
Figure US20040029735A1-20040212-C00180
in which
R2 and R3 are each as defined in any of claims 1 to 5 and
R represents alkyl, aryl or arylalkyl,
are reacted with aryl isocyanates of the general formula (V)
Figure US20040029735A1-20040212-C00181
in which
m, n, Q, R4, R5, X and Y are each as defined in any of claims 1 to 7
or with arylurethanes (arylcarbamates) of the general formula (VI)
Figure US20040029735A1-20040212-C00182
in which
m, n, Q, R4, R5, X and Y are each as defined in any of claims 1 to 7 and
R represents alkyl, aryl or arylalkyl,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or that
(c) N-aryl-1-alkoxycarbonylamino-maleimides of the general formula (VII)
Figure US20040029735A1-20040212-C00183
in which
m, n, Q, R3, R4, R5, X and Y are each as defined in any of claims 1 to 7 and
R′ represents alkyl
are reacted with a metal hydride in the presence of water and, if appropriate, in the presence of an organic solvent,
or that
(d) substituted phenyluracils of the general formula (Ia)
Figure US20040029735A1-20040212-C00184
in which
m, n, Q, R2, R3, R4, R5, X and Y are each as defined in any of claims 1 to 7
are reacted with 1-aminooxy-2,4-dinitro-benzene or with alkylating agents of the general formula (VIII)
X2—A1  (VIII)
in which
A1 represents optionally substituted alkyl and
X2 represents halogen or the grouping —O—SO2—O—A1
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and electrophilic or nucleophilic and/or oxidation or reduction reactions within the scope of the definition of the substituents are, if appropriate, subsequently carried out in a customary manner.
9. Compounds of the general formula (Ia)
Figure US20040029735A1-20040212-C00185
in which
m, n, Q, R2, R3, R4, R5, X and Y are each as defined in any of claims 1 to 7.
10. Compounds of the general formula (V)
Figure US20040029735A1-20040212-C00186
in which
m, n, Q, R4, R5, X and Y are each as defined in any of claims 1 to 7.
11. Compounds of the general formula (VI)
Figure US20040029735A1-20040212-C00187
in which
m, n, Q, R4, R5, X and Y are each as defined in any of claims 1 to 7 and
R represents alkyl, aryl or arylalkyl.
12. Compounds of the general formula (VII)
Figure US20040029735A1-20040212-C00188
in which
m, n, Q, R3, R4, R5, X and Y are each as defined in any of claims 1 to 7 and
R′ represents alkyl.
13. Compounds of the general formula (IX)
Figure US20040029735A1-20040212-C00189
in which
m, n, Q, R4, R5, X and Y are each as defined in any of claims 1 to 7.
14. Herbicidal compositions, characterized in that they comprise at least one compound according to any of claims 1 to 7 and 9 to 13 and customary extenders.
15. Use of at least one compound according to any of claims 1 to 7 and 9 to 12 for controlling undesirable plants.
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HK1045993A1 (en) 2002-12-20
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PL352284A1 (en) 2003-08-11
WO2000078734A1 (en) 2000-12-28
KR20020011989A (en) 2002-02-09
AU766978B2 (en) 2003-10-30
DE19927612A1 (en) 2000-12-21
US6624120B1 (en) 2003-09-23
AU5401700A (en) 2001-01-09
MXPA01012983A (en) 2002-09-02
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EP1192140A1 (en) 2002-04-03
CA2375243A1 (en) 2000-12-28

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