EP1109807A1 - Derives de benzoyl, leur procede de production et leur utilisation comme herbicides et regulateurs de croissance des plantes - Google Patents

Derives de benzoyl, leur procede de production et leur utilisation comme herbicides et regulateurs de croissance des plantes

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Publication number
EP1109807A1
EP1109807A1 EP99946028A EP99946028A EP1109807A1 EP 1109807 A1 EP1109807 A1 EP 1109807A1 EP 99946028 A EP99946028 A EP 99946028A EP 99946028 A EP99946028 A EP 99946028A EP 1109807 A1 EP1109807 A1 EP 1109807A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkylamino
halogen
group
alkoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99946028A
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German (de)
English (en)
Inventor
Andreas Van Almsick
Lothar Willms
Thomas Auler
Hermann Bieringer
Christopher Rosinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Aventis CropScience GmbH
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Filing date
Publication date
Application filed by Aventis CropScience GmbH filed Critical Aventis CropScience GmbH
Publication of EP1109807A1 publication Critical patent/EP1109807A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/18—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
    • C07D335/12—Thioxanthenes
    • C07D335/14—Thioxanthenes 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 in position 9
    • C07D335/16—Oxygen atoms, e.g. thioxanthones

Definitions

  • the invention relates to the technical field of herbicides and plant growth regulators, in particular that of herbicides for the selective control of weeds and weeds in crops of useful plants.
  • EP-A 0 712 853 and EP-A 0 841 335 describe condensed benzoyl derivatives which carry an alkyl radical in the ⁇ -position of the condensed ring system.
  • EP-A 0 629 623, EP-A 0 810 227 and EP-A 0 819 691 describe condensed benzoyl derivatives which are substituted by an alkoxy radical in the ⁇ -position of the condensed ring system.
  • WO 97/23135 discloses condensed benzoyl derivatives which carry a radical from the group alkyl, alkenyl, alkynyl, alkoxy and alkoxyimino in the ⁇ -position of the condensed ring system.
  • WO 98/29406 discloses condensed benzoyl derivatives which carry one or two radicals from the group alkyl, alkoxyimino, alkoxy, alkylthio and disubstituted amino in the ⁇ -position of the condensed ring system.
  • the three latter radicals can also be present in cyclic form, so that there is a cycloalkoxy, cycloalkylthio or cycloalkylamino radical in the ⁇ -position of the fused-on ring system.
  • WO 98/29406 mentions a condensed benzoyid derivative in which there is a (2-tetrahydrofuryl) methyloxy radical in said ⁇ position.
  • the object of the present invention is to provide herbicidal and plant growth-regulating compounds which overcome the disadvantages known from the prior art.
  • Q is a radical of the formula (II), (III) or (IV)
  • R 1 , R 2 , R 3 independently of one another are hydrogen, hydroxyl, thio, amino, cyano, nitro, halogen or an optionally substituted hydrocarbon radical which may additionally contain one or more, identical or different heteroatoms from the group consisting of oxygen, sulfur and nitrogen , Contains fluorine, chlorine, bromine and iodine;
  • R 4 is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxycarbonyl, phenyl, the six last-mentioned groups optionally being substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, Alkoxy and alkylthio are substituted;
  • R 5 can also be hydroxy
  • A is a divalent unit from the group O, S, SO, SO 2 , NR a , CHR a and CR a R b ;
  • B is a saturated chain or a chain containing one or more multiple bonds and consisting of one to four carbon atoms, which is optionally substituted by alkyl, haloalkyl, alkoxy, haloalkoxy or by a phenyl radical which is optionally substituted by alkyl, haloalkyl, alkoxy, haloalkoxy, halogen, cyano or nitro is;
  • E is a bond, a saturated chain or a one- to six-membered chain containing one or more multiple bonds, consisting of divalent units from the group C, CR C , CR c R d , N, NR C , S, SO, SO 2 , O and CO;
  • X is a divalent unit from the group O, S and NR e ;
  • R 6 alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, cyanato, thiocyanato, halogen or OR f ;
  • Y is a divalent unit from the group O, S, NH, N-alkyl or CHR 7 ;
  • R 7 is hydrogen, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran- 3-yl, alkyl, cycloalkyl, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylthio, phenyl, the hydrocarbon part of the eight last-mentioned radicals optionally substituted by one or more, identical or different radicals from the group halogen, alkylthio and alkyloxy, or
  • R 7 radicals bonded to directly adjacent carbon atoms form a bond or form an optionally substituted 3- to 6-membered ring with the carbon atoms carrying them;
  • Z is a bond, a divalent unit from the group O, S, SO, SO 2 , NH, N-alkyl or CHR 7 , where Y and Z should not simultaneously mean a divalent unit which is an oxygen, nitrogen or Contains sulfur atom;
  • G 1 -G 2 is a divalent unit from the group OCR 9 , SCR 9 and NR 10 COR 11 , the linkage with the ring system should be such that the carbon atom of this divalent unit is bonded to the carbon atom of the ring system via a double bond;
  • R 8 is hydrogen, alkyl or alkoxycarbonyl
  • R 9 is hydrogen, alkyl, cycloalkyl, haloalkyl or halocycloalkyl
  • R 10 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, benzyl, the six latter groups optionally being substituted by one or more, identical or different radicals from the group consisting of halogen, cyano, nitro and alkoxy;
  • R 11 is hydrogen, formyl, alkyl, haloalkyl, alkoxyalkyl or a group LR 12 ;
  • L is a divalent unit from the group SO 2 , CO, CHR 9 CO or CR 9 R h ;
  • R 12 is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkyl or a phenyl which is optionally substituted by one or more, identical or different radicals from the group consisting of cyano, nitro, alkyl, alkoxy, haloalkyl and haloalkoxy;
  • R a and R independently of one another are hydrogen, halogen, cyano, nitro, formyl, alkyl, cycloalkyl, alkenyl, alkynyl, alkylcarbonyl and alkylsulfonyl, the hydrocarbon part of the six latter radicals optionally being replaced by one or more, identical or different radicals from the group halogen, Nitro, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy and alkylthio;
  • R c and R d independently of one another are hydrogen, halogen, nitro, cyano, alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl , Haloalkylcarbonylamino, alkylcarbonyl-N-alkylamino, alkylsulfonyl, alkylsulfinyl, alkylsulfonylamino, haloalkylsulfonyl, haloalkylsulfinyl, alkylsulfonylamino and alkyl
  • R e is hydrogen, formyl, alkyl, cycloalkyl, alkenyl, alkynyl, alkylcarbonyl and alkylsulfonyl, the hydrocarbon part of the six last-mentioned radicals optionally being replaced by one or more, identical or different radicals from the group halogen, nitro, cyano, alkyl, cycloalkyl, alkenyl, Alkynyl, alkoxy and alkylthio can be substituted;
  • R f is hydrogen, alkyl, haloalkyl, alkoxyalkyl, formyl, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonyl, haloalkylsulfonyl, benzoyl or phenylsulfonyl, the aromatic part of the latter two radicals optionally being replaced by one or more, the same or various residues from the group alkyl, haloalkyl, alkoxy, haloalkoxy, halogen, cyano and nitro are substituted;
  • R 9 and R h are independently hydrogen or alkyl
  • R 'and R k independently of one another are hydrogen or R j ;
  • R 1 and R m are independently hydrogen or by one or more, or different radicals R are identical 1-substituted alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl or haloalkynyl, or R 1 and R m together with the carbon atom to which they are attached , a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated ring which optionally contains one to three heteroatoms from the group consisting of oxygen, sulfur and nitrogen, and which may be one or more of the same or various radicals R 1 is substituted.
  • n 0, 1, 2 or 3;
  • Numerous compounds of the formula (I) according to the invention can occur in different tautomeric structures, depending on external conditions, such as solvent and pH.
  • the compounds of the general formula (I) contain an acidic proton which can be removed by reaction with a base.
  • bases are, for example, alkali metals, such as lithium, sodium and potassium, alkaline earth metals, such as calcium and magnesium, ammonia and organic amines.
  • alkali metals such as lithium, sodium and potassium
  • alkaline earth metals such as calcium and magnesium
  • ammonia and organic amines Such salts are also the subject of the invention.
  • a hydrocarbon radical is a straight-chain, branched or cyclic, saturated, partially saturated, unsaturated or aromatic radical, for example alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl or aryl.
  • Compound terms such as cycloalkylalkenyl, cycloalkynylalkyl and arylalkynyl are also intended to be encompassed by this definition. Still contains this hydrocarbon residue additionally heteroatoms, these can basically be located at any position of the hydrocarbon residue, if the chemical structure allows it.
  • chain-like carbon-containing radicals such as alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and / or substituted radicals in the carbon skeleton such as alkenyl and alkynyl can each be straight-chain or branched.
  • the lower carbon skeletons e.g. with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 4 carbon atoms, preferred.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl, etc., mean e.g.
  • Alkynyl means e.g. Propargyl, but-2-in-1-yl, but-3-in-1-yl, 1-methyl-but-3-in-1-yl.
  • the multiple bond can be in any position of the unsaturated radical.
  • Cycloalkyl means a carbocyclic, saturated ring system with three to eight carbon atoms, e.g. Cyclopropyl, cyclopentyl or cyclohexyl.
  • cycloalkenyl means a monocyclic alkenyl group with three to eight carbon ring members, e.g. Cyclopropenyl, cyclobutenyl, cyclpentyl and cyclohexenyl, where the double bond can be located at any position.
  • composite radicals such as cycloalkylalkenyl
  • the former radical can be in any position of the latter.
  • Halogen means fluorine, chlorine, bromine or iodine.
  • Haloalkyl, -alkenyl and -alkynyl are partly or completely substituted alkyl, alkenyl or alkynyl, for example CF 3 , CHF 2 , CH 2 F, CF by halogen, preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine 3 CF 2 , CH 2 FCHCI, CCI 3 , CHCI 2 , CH 2 CH 2 CI;
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 CI; the same applies to haloalkenyl and other halogen-substituted radicals.
  • heterocyclyl is to be understood as meaning three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur. If chemically possible, the linkage can take place at any position on the heterocycle.
  • Examples of these are oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazoldinyl, 4-isoxazolidinyl, 5-isoxoazolidinyl, 3-isothioazolidiazine -lsothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl , 1, 2,4-oxadiazolidin-3-yl, 1, 2,4-oxadiazolidin-5-yl, 1, 2,4
  • Aryl represents an aromatic mono- or polycyclic hydrocarbon residue, e.g. Phenyl, naphthyl, biphenyi and phenanthryl. If chemically possible, the linkage can take place at any position of aryl.
  • Heteroaryl stands for an aromatic mono-, bi- or tricyclic radical which, in addition to carbon ring members, contains one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom. If chemically possible, the linkage can take place at any position of aryl.
  • 5-membered heteroaryl examples include 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2,4-triazolyl-3-yl , 1, 3,4-triazol-2-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3rd -lsothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl , 1, 2.4- Oxadiazol-3-yl, 1, 2,4-o
  • 6-membered heteroaryl examples include 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimdinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3,5-triazine -2-yl, 1, 2,4-triazin-3-yl and 1, 2,4,5-tetrazin-3-yl.
  • fused 5-membered heteroaryl examples include benzothiazol-2-yl and benzoxazol-2-yl.
  • benzo-fused 6-membered heteroaryl examples include quinoline, isoquinoline, quinazoline and quinoxaline.
  • the definition of a divalent unit is to be understood in such a way that saturation can take place via single, double and / or triple bonds.
  • the divalent unit “O” therefore means an oxygen atom linked via two single bonds.
  • the divalent unit “CR C” means a carbon atom linked via a single and a double bond and carrying a radical R c .
  • the divalent unit “C” stands for a carbon atom which is linked via a single and a triple bond.
  • the compounds of the general formula (I) can be present as stereoisomers.
  • stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation processes. Stereoisomers can also be prepared selectively by using stereoselective reactions using optically active starting materials and / or auxiliary substances.
  • the invention also relates to all stereoisomers and mixtures thereof which are encompassed by the general formula (I) but are not specifically defined.
  • the expression "partially or fully halogenated” is intended to express that the hydrogen atoms in the groups characterized in this way can be replaced in part or in full by the same or different halogen atoms as mentioned above.
  • R 1 , R 2 , R 3 independently of one another are hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarycylcylllyl, heterocarylcylllyl, heterocarylcylllyl, heterocarylcylllyl, heterocarylcylllyl, heteroarylcyllyl, heterocyclylalkynyl, hydroxy, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkylalkoxy, Cycloalkylalkenyloxy, Cycloalkylalkinyloxy, Cycloa
  • Heteroarylalkinylsulfonyloxy Heterocyclylsulfonyloxy, Heterocyclylalkylsulfonyloxy, Heterocyclylalkenylsulfonyloxy, Heterocyclylalkinylsulfonyloxy, alkylsulfonylamino, Alkenylsuifonylamino, Alkinylsulfonylamino, cycloalkylsulfonylamino, Cycloalkylalkylsulfonylamino, Cycloalkylalkenylsulfonylamino, Cycloalkylalkinylsulfonylamino, arylsulfonylamino, Arylalkylsulfonylamino, Arylalkenylsulfonoamino, Arylalkinylsulfonylamino, Heteroarylsulfon
  • R 5 is optionally one or more, the same or different, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarycylllyllyl, heteroarylcylllyl, heteroarylcylllyl, heteroarylcylllyl, heteroarylcylllyl, heteroarylcylllyl, heteroarylcylllyl, heteroarylcylllyl, heteroarylcylllyl, heteroarylcylllyl, heteroaryllcyllyl, heteroarylcylllyl, heteroarylcylllyl, heteroarylcylllyl, heteroarylcy
  • R 5 can also be hydroxy.
  • R 1 , R 2 , R 3 independently of one another are hydrogen, halogen, nitro, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy, alkylsulfonylamino, alkylsulfonyl-N-alkylamino, phenyl, benzyl, where the thirteen last-mentioned groups are optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy and alkylthio;
  • R 4 is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, the four last-mentioned groups optionally being substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, alkyl, cycloalkyl, alkynyl, alkoxy, alkylthio;
  • R 5 is an optionally mono- or polysubstituted by identical or different halogen, nitro, cyano, formyl, amino, phenyl, benzyl, (C ⁇ -C6) alkyl, (C 2 -C 6) - alkenyl, (C 2 - C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (CC 6 ) alkoxy, (CC 6 ) alkylamino, di- (Ci-C ⁇ J-alkylamino, (CrC ⁇ J-alkoxycarbonyl, (d-C
  • R 5 can also be hydroxy
  • A is a divalent unit from the group S, SO, SO 2l and NR a ;
  • B is a saturated chain or a chain containing one or two carbon atoms and is optionally substituted by alkyl, haloalkyl, alkoxy or haloalkoxy;
  • E is a bond, CR c R d , NR C , S, SO, SO 2 , O and CO;
  • R 6 (-C -C 6 ) alkylthio, (CrC 6 ) alkylsulfinyl, (dC 6 ) alkylsulfonyl, cyano, cyanato, thiocyanato, halogen or OR f ;
  • Y is a divalent unit from the group O, S, N- (dC 6 ) -alkyl or CHR 7 ;
  • R 7 is hydrogen, (dC 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (dC 6 ) -alkoxy, (CC 6 ) -alkoxy- (d-CeJ-alkyl, (-C-C 6 ) -alkylcarbonyl , (dC 6 ) -alkoxycarbonyl, (dC 6 ) -alkylthio, phenyl, the hydrocarbon part of the eight last-mentioned radicals optionally being substituted by one or more, identical or different radicals from the group halogen, (d-dJ-alkylthio and (C ⁇ -C 3 ) alkyloxy is substituted;
  • Z is a bond, CH 2 or CHR 7 ;
  • R 8 is hydrogen, (dC 6 ) alkyl or (dC 6 ) alkoxycarbonyl
  • R 9 is hydrogen, (CrC 6 ) alkyl, (C 3 -C 8 ) cycloalkyl or halo (CC 6 ) alkyl;
  • R 10 is hydrogen, (d-CeJ-alkyl, (C 2 -C 6 ) alkenyl, (CC 6 ) alkynyl, (C 3 -C 8 ) cycloalkyl, phenyl, benzyl, the six latter radicals being optionally groups one or more, identical or different radicals from the group halogen, cyano, nitro and (d-C ⁇ J-alkoxy are substituted;
  • R 11 is hydrogen, formyl, (CC 6 ) -alkyl, halogen- (CC 6 ) -alkyl, (dC 6 ) -alkoxy- (C ⁇ - C ⁇ J-alkyl or a group LR 12 ;
  • L is a divalent unit from the group SO 2 , CO and CHR 9 CO;
  • R 12 (-CC 6 ) alkyl, halogen (CrC 6 ) alkyl, or if necessary by one or more, identical or different radicals from the group cyano, nitro, (C 1 -C 3 ) - Alkyl, (CC 3 ) alkoxy, halogen (CC 3 ) alkyl and halogen (CC 3 ) alkoxy substituted phenyl;
  • R a is hydrogen, halogen, cyano, nitro, formyl, (d-Ce ⁇ alkyl, (C 3 -C 8 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, ( CC 6 ) -alkylcarbonyl and (dC 6 ) -alkylsulfonyl, the hydrocarbon part of the six last-mentioned radicals optionally being replaced by one or more, identical or different radicals from the group halogen, nitro, cyano, (CC 6 ) -alkyl, (C 3 - C 8 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C C ⁇ ) alkoxy and (CrC ⁇ J alkylthio);
  • R c and R d independently of one another hydrogen, halogen, nitro, cyano, (d-C ⁇ ) - alkyl, halogen- (dC 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 2 -C 6 ) - Alkenyl, halogen (C 2 -C 6 ) aikenyl, (C 2 -C 6 ) alkynyl, halogen (C 2 -C 6 ) alkynyl, (dC 6 ) alkoxy, halogen (CC 6 ) - alkoxy, (dC 6 ) -alkylthio, halogen- (dC 6 ) -alkylthio, (d-C ⁇ J-alkylcarbonyl, halogen- (CrC 6 ) -alkylcarbonyl, (C ⁇ -C 6 ) -alkoxycarbonyl, halogen- (CrC 6
  • R ⁇ is hydrogen, formyl, (CC 6 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 - C ⁇ J-alkynyl, (d-C ⁇ J-alkylcarbonyl and (CrC 6) -alkylsulfonyl, where the hydrocarbon moiety of the six last-mentioned radicals optionally substituted by one or more identical or different radicals from the group halogen, nitro, cyano, (C ⁇ -C6) alkyl, cycloalkyl, (C 2 -C 6) - Alkenyl, (C 2 -C 6 ) - (CC 6 ) alkynyl, (dC 6 ) alkoxy and (CrC ⁇ J-alkylthio) may be substituted;
  • R f is hydrogen, (CrC 6 ) alkyl, halo (dC 6 ) alkyl, (d-CeJ alkylcarbonyl, (d- C 6 ) alkoxycarbonyl, (CrC 6 ) alkylsulfonyl, halo (C 1 -C 6 ) -alkylsulfonyl, benzoyl or phenylsulfonyl, the aromatic part of the latter two radicals optionally being replaced by one or more, identical or different radicals from the group (d-C ⁇ ) -alkyl, halogen- (dC 6 ) -alkyl, (dC 6 ) Alkoxy, halogen (dC 6 ) alkoxy, halogen, cyano and nitro;
  • R 9 and R h independently of one another hydrogen or (-CC 6 ) alkyl, and w 0, 1, 2 or 3
  • Preferred compounds of the general formula I are those in which
  • R 1 , R 2 , R 3 independently of one another are hydrogen, halogen, nitro, cyano, (dC 6 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) -alkynyl, (dC 6 ) -alkoxy, (CC 6 ) -alkylthio, (CC 6 ) -alkylsulfinyl, (dC 6 ) -alkylsulfonyl, (dC 6 ) -alkylsulfonyloxy, (d- C ⁇ J-alkylsulfonylamino, (C ⁇ - C6) -Alkylsulfonyl-N- (dC 6 ) -alkylamino, phenyl, benzyl, the thirteen last-mentioned groups optionally being substituted by one or more, identical or different radicals from the
  • R 5 is optionally one or more, identical or different, by halogen, nitro, cyano, formyl, amino, phenyl, benzyl, (dC 4 ) alkyl, (C 2 -C) alkenyl, (C 2 -C) - Alkynyl, (C 3 -C 6 ) -cycloalkyl, (dC 4 ) -alkoxy, (dC 4 ) -alkylamino, di- (-C-C 4 ) -alkylamino, (dC) -alkoxycarbonyl, (Ci-dJ-alkylaminocarbonyl, Di- (-C-C 4 ) - alkylaminocarbonyl, (dC) -alkylcarbonyl, (dC 4 ) -alkylcarbonylamino, (dd) - alkylthio, (dC 4 ) -alkylsulfinyl, (CC) -
  • R 5 can also be hydroxy
  • A is a divalent unit from the group S, SO, and SO 2 ;
  • B contains a saturated or a double bond and consists of one or two carbon atoms, which may be replaced by one or two identical or different radicals from the group (-C-C 3 ) -alkyl, halogen- (dC 3 ) -alkyl, (C ⁇ - C 3 ) alkoxy or halogen (dC 3 ) alkoxy is substituted;
  • E is a bond, CR c R d , SO 2 and CO;
  • R 6 (CrC 3 ) alkylthio, (dC 3 ) alkylsulfonyl, cyano, cyanato, thiocyanato, halogen or OR f ;
  • Y is a divalent unit from group O or CHR 7 ;
  • R 7 is hydrogen, (dC 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (dC 6 ) -alkoxy- (-C-C 6 ) -alkyl, (d-C ⁇ J-alkylcarbonyl, (Ci-C ⁇ J-alkoxycarbonyl , Phenyl, the six latter radicals optionally being substituted by one or more, identical or different halogen atoms;
  • R 9 (-C -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl or halogen (dC 6 ) alkyl;
  • R 10 (dC 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 3 -C 8 ) cycloalkyl, phenyl or benzyl;
  • R 11 is hydrogen, (CC 6 ) alkyl or a group LR 12 ;
  • R c and R d independently of one another are hydrogen, (d-dJ-alkyl, halogen (dC 3 ) alkyl, (C 2 -C 6 ) alkenyl, halogen (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) -alkynyl, halogen- (C 2 -C 6 ) -alkynyl, (-C-C 3 ) -alkoxy, halogen- (CrC 3 ) -alkoxy, (CC 3 ) -alkylthio, halogen- (dC 3 ) - alkylthio and (d-C3) alkylcarbonyl;
  • R f is hydrogen, (dC 6 ) -alkyl, (-C-C 6 ) alkylcarbonyl, (dC 6 ) -alkoxycarbonyl, (C C ⁇ J-alkylsulfonyl, benzoyl or phenylsulfonyl, the aromatic part of the latter two radicals optionally being replaced by one or more , identical or different radicals from the group (dC 6 ) alkyl, halogen (d-C6) alkyl, (C-rC ⁇ ) alkoxy, halogen (-C-C 6 ) alkoxy, halogen, cyano and nitro substituted is and
  • R 1 and R 2 independently of one another are hydrogen, (CrC 4 ) -alkyl, halogen or nitro;
  • R 3 and R 4 are hydrogen
  • E is a bond or a divalent unit from the group CH 2 , CO and SO 2 ;
  • G 1 -G 2 is a divalent unit from the group OCR 9 and NR 0 COR 11 ;
  • R 7 is hydrogen or (CC 6 ) alkyl
  • R 8 is hydrogen
  • R 9 (C 3 -C 6 ) cycloalkyl
  • R 11 is hydrogen or a group LR 12 ;
  • L is a divalent unit from the group SO 2 , CO and CH 2 CO;
  • R 12 optionally by one or more, identical or different radicals from the group halogen, cyano, nitro, (CrC 6 ) alkyl, (C ⁇ -C 6 ) alkoxy, (CC 6 ) - haloalkyl and (C ⁇ -C 6 ) -Halogena! Koxy substituted phenyl;
  • R e is hydrogen, formyl, (CC 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (dC 6 ) - alkylcarbonyl and (-C-C 6 ) alkylsulfonyl;
  • R f is hydrogen, (-CC 6 ) alkylsulfonyl, benzoyl, phenylsulfonyl, the latter two radicals optionally being substituted by one or more, identical or different radicals from the group (dC 6 ) -alkyl, (Ci-C ⁇ J-haloalkyl , (dC 6 ) - alkoxy, (dC ⁇ J-haloalkoxy, halogen, cyano and nitro are substituted, and
  • R 5 is optionally one or more, the same or different, halogen, nitro, cyano, formyl, amino, phenyl, benzyl, (dC) -alkyl, (C 2 -C 4 ) - alkenyl, (C 2 -C 4 ) -Alkynyl, (C 3 -C 6 ) -cycloalkyl, (dC 4 ) -alkoxy, (dC 4 ) -alkylamino, di- (CrC) -alkylamino, (CrC 4 ) -alkoxycarbonyl, (C-C 4 ) -alkylaminocarbonyl , Di- (dd) - alkylaminocarbonyl, (C ⁇ -C 4 ) alkylcarbonyl, (C 1 -C 4 ) -alkylcarbonylamino, (dd) - alkylthio, (C ⁇
  • the compounds according to the invention can be prepared, for example, starting from the known compound or the compound of the general formula (Ia) which can be prepared by known methods by one or more of the processes given in the following schemes.
  • Scheme 1 shows the acid-catalyzed reaction of the compound of formula (Ic) with ethanediol, which leads to the compound of formula (Id).
  • the subsequent reaction with n-butyllithium or magnesium, carbon dioxide and subsequent acid treatment provides compound of the formula (le) in which R represents OH.
  • R represents OH.
  • Such reactions are known for example from J. Org. Chem. 55, 773 (1990).
  • This compound can be converted into the corresponding esters of the formula (Ie) in which R is alkoxy by conventional esterification methods.
  • the substituents should have the same meanings as given for formula (I).
  • the invention also relates to compounds of the formula (Ig)
  • the compounds of formula (I) according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants.
  • Perennial weeds that are difficult to control and that sprout from rhizomes, rootstock or other permanent organs are also well captured by the active ingredients. It is usually irrelevant whether the substances are applied by pre-sowing, pre-emergence or post-emergence.
  • Some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned in detail, which can be controlled by the compounds according to the invention without the name being intended to restrict them to certain species.
  • weed species for example, Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria as well as Cyperus species from the annual group and on the part of the perennial species Agropyron, Cynodon, imperata as well as sorghum and perennial Cyperus species are well recorded.
  • the spectrum of action extends to species such as Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Sida on the annual side as well as Convolvulus, Cirsium, Rumex and Artemisia for the perennial weeds.
  • Harmful plants occurring in the rice under the specific culture conditions such as, for example, Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus, are also superbly combated by the active compounds according to the invention. If the compounds according to the invention are applied to the surface of the earth before germination, either the weed seedlings emerge completely or the weeds grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.
  • the compounds of the invention have excellent herbicidal activity against monocotyledonous and dicotyledon weeds, crop plants of economically important crops such as e.g. Wheat, barley, rye, rice, corn, sugar beet, cotton and soy are only slightly or not at all damaged. For these reasons, the present compounds are very suitable for the selective control of undesired plant growth in agricultural crops or in ornamental crops.
  • the active compounds can also be used to control harmful plants in crops of known or still to be developed genetically modified plants.
  • the transgenic plants are generally distinguished by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. B. the crop in terms of quantity, quality, storability, composition and special ingredients.
  • Transgenic plants with an increased starch content or altered starch quality or with a different fatty acid composition of the crop are known.
  • the compounds of the formula (I) can preferably be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made resistant to genetic engineering.
  • new plants which have modified properties in comparison to previously occurring plants are, for example, classic breeding methods and the generation of mutants.
  • new plants with modified properties can be produced using genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624).
  • genetic engineering changes in crop plants have been described in order to modify the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827,
  • Glufosinate see e.g. EP-A-0242236, EP-A-242246) or glyphosate
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP-A-0142924,
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of the above standard procedures such. B. base exchanges, partial sequences removed or natural or synthetic sequences added. To connect the DNA fragments to one another, adapters or linkers can be attached to the fragments.
  • the production of plant lines with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense-RNA, a sense-RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme which specifically cleaves transcripts of the above-mentioned gene product .
  • DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
  • the synthesized protein When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a particular compartment, z. B. the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219- 3227; Wolter et al., Proc. Natl. Acad. Be. USA 85: 846-850 (1988); Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the transgenic plant cells can be regenerated into whole plants using known techniques.
  • the transgenic plants can in principle be plants of any plant species, i.e. both monocot and dicot plants.
  • the compounds according to the invention can preferably be used in transgenic crops which are resistant to herbicides from the group of the sulfonylureas, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active compounds.
  • the active compounds according to the invention are used in transgenic crops, in addition to the effects on harmful plants which can be observed in other crops, there are often effects which are specific to the application in the respective transgenic culture, for example a changed or specially expanded weed spectrum which can be controlled changed Application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing the growth and yield of the transgenic crop plants.
  • the invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the substances according to the invention have excellent growth-regulating properties in crop plants. They intervene regulating the plant's own metabolism and can therefore be used to influence plant constituents in a targeted manner and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesired vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as this can reduce or completely prevent storage.
  • the compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
  • the invention therefore also relates to herbicidal and plant growth-regulating compositions which comprise compounds of the formula (I).
  • the compounds of formula (I) can be formulated in different ways, depending on which biological and / or chemical-physical parameters are specified. Possible formulation options are, for example: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusts (DP), pickling agents, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and Adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powder
  • EC emulsifiable concentrates
  • EW emulsion
  • combinations with other pesticidally active substances e.g. Manufacture insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a finished formulation or as a tank mix.
  • pesticidally active substances e.g. Manufacture insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water and, in addition to the active ingredient, in addition to a diluent or inert substance, are also surfactants of an ionic and / or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonatesulfonates, alkylbenzene sulfonates, alkylbenzene sulfonates, alkylbenzene sulfonates, alkyl benzene sulfonates, alkyl benzene sulfonates, alkyl benzene sulfonates, alkyl benzene sulfonates, alkyl benzene sulfonates, alkyl benzene
  • the herbicidal active ingredients are finely ground, for example in conventional apparatus such as hammer mills, fan mills and air jet mills, and mixed at the same time or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, for example butanoi, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
  • emulsifiers may be used, for example: calcium alkylarylsulfonates such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan fatty acid such as Polyoxethylensorbitanester.
  • calcium alkylarylsulfonates such as Ca dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solid substances e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates can be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally adding surfactants, such as those e.g. already listed above for the other types of formulation.
  • Emulsions e.g. Oil-in-water emulsions (EW) can be used, for example, using stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, such as those e.g. already listed above for the other formulation types.
  • EW Oil-in-water emulsions
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, for example polyvinyl alcohol, polyacrylic acid sodium or mineral oils, to the surface of carriers such as sand, kaolinite or granulated inert material.
  • active ingredients can also in the usual manner for the production of fertilizer granules - if desired in a mixture with fertilizers - granulated.
  • Water-dispersible granules are generally produced using the customary methods, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active ingredient of the formula (I).
  • the active ingredient concentration in wettable powders is, for example, about 10 to 90% by weight, the remainder to 100% by weight consists of customary formulation components.
  • the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight.
  • Dust-like formulations contain 1 to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
  • the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating aids, fillers, etc. are used.
  • the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersing agents, emulsifying agents, penetration agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity.
  • active ingredients such as those described, for example, in Weed Research 26, 441-445 (1986) or "The Pesticide Manual", 11th edition, The British Crop Protection Council and the, can be used as combination partners for the active ingredients according to the invention in mixture formulations or in the tank mix Royal Soc. of Chemistry, 1997 and the literature cited therein.
  • Known herbicides which can be combined with the compounds of the formula (I) are, for example, the following active substances (note: the compounds are either with the "common name” according to the International Organization for Standardization (ISO) or with the chemical name , possibly together with a usual code number): acetochlor; acifluorfen; aclonifen; AKH 7088, ie [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and methyl acetate; alachlor; alloxydim; ametryn; amidosulfuron; amitrole; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; azimsulfurone (DPX-A8947); aziprotryn; barban; BAS 516 H, ie 5-fluoro-2-
  • the formulations present in commercial form are optionally diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, using water. Dust-like preparations, ground or scatter granules as well as sprayable Solutions are usually no longer diluted with other inert substances before use.
  • the required application rate of the compounds of formula (I) varies with the external conditions, such as temperature, humidity, the type of herbicide used, and others. It can vary within wide limits, for example between 0.001 and 10.0 kg / ha or more of active substance, but is preferably between 0.005 and 5 kg / ha.
  • Step 1 3 - [(2,5-Dimethylphenyl) thio] propanoic acid
  • Step 4 6-bromo-5,8-dimethyl-spiro [thiochroman-4,2 ' - [1, 3] dioxolane]
  • Crystals which had precipitated overnight were filtered off with suction, washed with cold heptane and dried.
  • Step 5 5,8-dimethyl-4-oxo-6-thiochromanecarboxylic acid 46.38 g (0.15 mol) of 6-bromo-5,8-dimethyl-spiro [thiochroman-4,2 ' - [1, 3] dioxolane] were added 500 ml of tetrahydrofuran dissolved and cooled to -65 ° C. 80 ml (0.2 mol) of 2.5 M n-butyllithium in hexane were then allowed to drip in slowly enough that the temperature did not rise above -55.degree. The mixture was left to stir for 1 h and then poured add 90 g dry ice in portions. The solution was then left on
  • Step 8 methyl 5,8-dimethyl-4-hydroxy-1, 1-dioxo-1, 2,3,4-tetrahydro-1 ⁇ 6 -thio-chromene-6-carboxylate
  • Step 9 Methyl 4 - ⁇ [3-chloro-5- (trifluoromethyl) -2-pyridyl] oxy ⁇ -5,8-dimethyl-1, 1-dioxo-1, 2,3,4-tetrahydro-1 ⁇ 6 -thiochromene-6-carboxylate
  • Step 10 4 - ⁇ [3-chloro-5- (trifluoromethyl) -2-pyridyl] oxy ⁇ -5,8-dimethyl-1, 1-dioxo-1, 2,3,4-tetrahydro-1 ⁇ 6 - thiochrome-6-carboxylic acid
  • Step 11 3-Oxo-1-cyclohexenyl 4 - ⁇ [3-chloro-5- (trifluoromethyl) -2-pyridyl] oxy ⁇ -5,8-dimethyl-1, 1 -dioxo-1, 2,3 , 4-tetrahydro-1 ⁇ 6 -thiochromene-6-carboxylate 0.56 g (1.2 mmol) 4 - ⁇ [3-chloro-5- (trifluoromethyl) -2-pyridyl] oxy ⁇ -5,8-dimethyl-1, 1 - Dioxo-1, 2,3,4-tetrahydro-1 ⁇ 6 -thiochromene-6-carboxylic acid were added in 30 ml of methylene chloride with 2 drops of N, N-dimethylformamide and 0.48 g (3.8 mmol) of oxalyl chloride and the mixture was boiled under reflux for 3.5 h.
  • Step 1 4-benzoyloxy-5,8-dimethyl-1, 1-dioxo-1, 2,3,4-tetrahydro-1 ⁇ 6 -thiochromene-6-carboxylic acid 1.0 g (4.1 mmol) of 5,8-dimethyl-4-hydroxy-1, 1-dioxo-1, 2,3,4-tetrahydro-1 ⁇ 6 -thiochromen-6-carboxylic acid, 0.58 g (4.1 mmol) of benzoyl chloride and a spatula tip of NN-4-dimethylaminopyridine were stirred in 10 ml of pyrides overnight. It was then poured onto 5 M HCl on crushed ice and extracted with ethyl acetate.
  • Step 2 3-oxo-1-cyclohexenyl 4-benzoyloxy-5,8-dimethyl-1, 1-dioxo-1, 2,3,4-tetrahydro-1 ⁇ 6 -thiochromene-6-carboxylate
  • Residue was taken up in 100 ml of methylene chloride and 0.25 g (2.2 mmol) of cyclohexanedione and 0.44 g (7.4 mmol) of triethylamine were added at 0 ° C. It was left for 4 hours
  • Step 3 6 - [(2,6-dioxocyclohexyl) carbonyl] -4-benzoyloxy-5,8-dimethyl-1, 2,3,4-tetrahydro-1 ⁇ 6 -thiochromen-1, 1-dione
  • Table 1 a precursors of the compounds in Table 1
  • Table 1b precursors of the compounds in Table 1a
  • Table 1c precursors of the compounds in Table 1 b
  • R 7 R A , R B , R c , R D Q : remainder of formula (II)
  • A SO 2 B - CH -CH 2
  • R 1 CH 3
  • a dusting agent is obtained by mixing 10 parts by weight of a compound of the general formula (I) and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of a compound of the general formula (I), 64 parts by weight of quartz containing kaolin as an inert substance, 10 parts by weight of potassium lignosulfonic acid and 1 Mixes parts by weight of oleoylmethyl tauric acid sodium as a wetting and dispersing agent and grinds in a pin mill.
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the general formula (I), 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight. Mixes parts of paraffinic mineral oil (boiling range approx. 255 to above 277 ° C) and grinds to a fineness of less than 5 microns in a friction ball mill.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the general formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emuigator.
  • a water-dispersible granulate is obtained by:
  • a water-dispersible granulate is also obtained by adding 25 parts by weight of a compound of the general formula (I),
  • Seeds of monocotyledonous and dicotyledonous weed plants are laid out in sandy loam in cardboard pots and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders or emulsion concentrates are then applied to the surface of the covering earth as an aqueous suspension or emulsion with a water application rate of the equivalent of 600 to 800 l / ha in a dosage of the equivalent of 1 kg of active substance or less per hectare.
  • the pots are placed in the greenhouse and kept under good growth conditions for the weeds.
  • the optical damage to the plants or the emergence damage is assessed after a test period of 3 to 4 weeks in comparison to untreated controls.
  • Examples 7 and 11 show an at least 80% activity against Stellaria media, Avena fatua, Lolium multiflorum and Setaria viridis.
  • the compounds of Examples Nos. 2, 3, 4, 7, 11 and 12 show an at least 90% activity against Amaranthus retroflexus, Sinapis arvensis and Setaria viridis.
  • the compounds of Examples Nos. 1, 2, 6, and 7 show a 100% activity against Amaranthus retroflexus and Stellaria media.
  • Seeds of monocotyledonous and dicotyledonous weeds are placed in cardboard pots in sandy loam soil, covered with soil and grown in the greenhouse under good growing conditions.
  • the test plants are treated three to three weeks after sowing.
  • the compounds according to the invention formulated as wettable powder or as emulsion concentrates are sprayed onto the green parts of the plant in a dosage of the equivalent of 1 kg of active substance or less per hectare with a water application rate of the equivalent of 600 to 800 l / ha. After the test plants have stood in the greenhouse for 3 to 4 weeks under optimal growth conditions, the effect of the preparations is assessed in comparison with untreated controls.
  • the agents according to the invention also have good herbicidal activity against a broad spectrum of economically important grasses and weeds, even after emergence.
  • the compounds of Examples 3, 9, 10, 11 and 12 show an at least 90% activity against Sinapis arvensis.
  • the compounds of Examples Nos. 1, 4, 7 and 10 show an activity of at least 80% against Stellaria media and Setaria viridis.
  • the compounds of Examples Nos. 6 and 9 show an at least 80% activity against Avena fatua and Amaranthus retroflexus.
  • Typical harmful plants in rice crops are grown in the greenhouse under paddy rice conditions (water retention level: 2 - 3 cm). After the treatment with the formulated compounds according to the invention in a dosage of the equivalent of 1 kg of active substance or less per hectare, the test plants are placed in the greenhouse under optimal growth conditions and are kept for the entire test period. About three weeks after application, the evaluation of the plant damage is carried out visually in comparison to untreated controls.
  • the compounds according to the invention have very good herbicidal activity against harmful plants.
  • the compounds of Examples Nos. 2, 4, 7, 11 and 12 show at least 80% activity against Cyperus iria and Echinocloa crus-galli.

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Abstract

L'invention concerne des dérivés de benzoyl de la formule générale (I), leur procédé de production et leur utilisation comme herbicides et régulateurs de croissance des plantes. Dans la formule générale (I), R?1, R2, R3, R4 et R5¿ représentent différents restes organiques, Q représente de l'isothiazol, de l'isoxazol, un reste cyclohexandion ou β-cétonitrile et A, B, E ainsi que X représentent des unités divalentes monoatomiques ou polyatomiques.
EP99946028A 1998-09-04 1999-08-26 Derives de benzoyl, leur procede de production et leur utilisation comme herbicides et regulateurs de croissance des plantes Withdrawn EP1109807A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19840337 1998-09-04
DE19840337A DE19840337A1 (de) 1998-09-04 1998-09-04 Benzoylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
PCT/EP1999/006259 WO2000014087A1 (fr) 1998-09-04 1999-08-26 Derives de benzoyl, leur procede de production et leur utilisation comme herbicides et regulateurs de croissance des plantes

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EP (1) EP1109807A1 (fr)
JP (1) JP2002524459A (fr)
KR (1) KR20010085762A (fr)
CN (1) CN1149211C (fr)
AR (1) AR020376A1 (fr)
AU (1) AU752786B2 (fr)
BR (1) BR9913461A (fr)
CA (1) CA2343151A1 (fr)
CO (1) CO5210935A1 (fr)
CZ (1) CZ2001796A3 (fr)
DE (1) DE19840337A1 (fr)
HU (1) HUP0104201A3 (fr)
ID (1) ID29626A (fr)
IL (1) IL141374A0 (fr)
MY (1) MY130252A (fr)
PL (1) PL346496A1 (fr)
RU (1) RU2223271C2 (fr)
SK (1) SK2962001A3 (fr)
TR (1) TR200100695T2 (fr)
TW (1) TW585863B (fr)
UA (1) UA68395C2 (fr)
WO (1) WO2000014087A1 (fr)
ZA (1) ZA200101563B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000035835A1 (fr) 1998-12-11 2000-06-22 Daicel Chemical Industries, Ltd. Procede de preparation de composes organiques au moyen de catalyseurs imide
DE19950943A1 (de) 1999-10-22 2001-05-17 Aventis Cropscience Gmbh Synergistische herbizide Mittel enthaltend Herbizide aus der Gruppe der Hemmstoffe der Hydroxyphenylpyruvat-Dioxygenase
WO2007079346A2 (fr) * 2005-12-30 2007-07-12 Olsen Christopher J Ensembles roue articulée et véhicules qui en sont équipés
JP2010504281A (ja) * 2006-07-27 2010-02-12 エミスフェアー・テクノロジーズ・インク アリールスルファニル化合物、および活性薬剤を送達するための組成物
EP2394995B1 (fr) * 2009-02-03 2014-01-15 Kumiai Chemical Industry CO., LTD. Dérivés de 2-pyridone à cycles condensés et herbicides
US9035067B2 (en) 2011-03-15 2015-05-19 Bayer Intellectual Property Gmbh N-(1,2,5-Oxadiazol-3-yl)-, N-(tetrazol-5-yl)- and N-(triazol-5-yl)bicycloarylcarboxamides and their use as herbicides
CN103992301B (zh) * 2014-05-09 2016-01-13 上海大学 2-羟基-5-氧代-4-芳基-2-三氟甲基-3,4,5，6，7,8-六氢-2h-色烯-3-羧酸乙酯化合物的制备方法
BR112017028600A2 (pt) 2015-07-01 2018-08-28 Syngenta Participations Ag derivados policíclicos ativos com substituintes contendo enxofre ativos em termos pesticidas
AU2016299728A1 (en) * 2015-07-24 2018-02-15 Bayer Cropscience Aktiengesellschaft Substituierted Furano-/Thienocycloalkylamino-2-Pyrimidine derivatives and use thereof for controlling undesired plant growth
CN107398300B (zh) * 2017-07-24 2020-08-21 中国科学院化学研究所 芳香族酰胺芳环c-h键直接氨基化反应的方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2134257T3 (es) 1992-03-03 1999-10-01 Idemitsu Kosan Co Derivado de pirazol.
CA2117413C (fr) * 1993-07-30 2006-11-21 Neil Geach Derives herbicides isoxazole-4-yl-methanone
CA2175675A1 (fr) 1993-11-09 1995-05-18 Mitsuru Shibata Derives de pyrazole et herbicide les contenant
GB9405229D0 (en) * 1994-03-17 1994-04-27 Rhone Poulenc Agriculture Compositions of matter
EP0768033B1 (fr) 1994-06-27 1999-12-08 Idemitsu Kosan Company Limited Composition herbicide
WO1996025413A1 (fr) * 1995-02-15 1996-08-22 Idemitsu Kosan Co., Ltd. Derives d'isoxazole
US5863866A (en) 1995-04-05 1999-01-26 Idemitsu Kosan Co., Ltd. Pyrazole derivatives
WO1997008164A1 (fr) * 1995-08-25 1997-03-06 E.I. Du Pont De Nemours And Company Herbicides bicycliques
AU7145296A (en) * 1995-10-04 1997-04-28 Idemitsu Kosan Co. Ltd Pyrazole derivatives
AU7227296A (en) * 1995-10-09 1997-04-30 Idemitsu Kosan Co. Ltd 2-cyano-1,3-dione derivatives and herbicides containing the same as active ingredient
WO1997023135A1 (fr) * 1995-12-25 1997-07-03 Idemitsu Kosan Co., Ltd. Composition herbicide
US6297198B1 (en) * 1996-05-14 2001-10-02 Syngenta Participations Ag Isoxazole derivatives and their use as herbicides
US6037312A (en) * 1996-05-23 2000-03-14 Idemitsu Kosan Co., Ltd. Isoxazole derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0014087A1 *

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CN1149211C (zh) 2004-05-12
CN1317004A (zh) 2001-10-10
JP2002524459A (ja) 2002-08-06
AU752786B2 (en) 2002-10-03
TR200100695T2 (tr) 2001-07-23
PL346496A1 (en) 2002-02-11
MY130252A (en) 2007-06-29
CZ2001796A3 (cs) 2001-08-15
ID29626A (id) 2001-09-06
US6297196B1 (en) 2001-10-02
RU2223271C2 (ru) 2004-02-10
CA2343151A1 (fr) 2000-03-16
CO5210935A1 (es) 2002-10-30
SK2962001A3 (en) 2001-11-06
WO2000014087A1 (fr) 2000-03-16
DE19840337A1 (de) 2000-03-09
BR9913461A (pt) 2001-07-24
HUP0104201A3 (en) 2002-04-29
UA68395C2 (en) 2004-08-16
AU5855199A (en) 2000-03-27
HUP0104201A2 (hu) 2002-03-28
TW585863B (en) 2004-05-01
KR20010085762A (ko) 2001-09-07
ZA200101563B (en) 2002-05-10
IL141374A0 (en) 2002-03-10
AR020376A1 (es) 2002-05-08

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