EP1497251A1 - Benzoylcyclohexandiones substitues par 3-ceto ou 3-oxime-ether - Google Patents

Benzoylcyclohexandiones substitues par 3-ceto ou 3-oxime-ether

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Publication number
EP1497251A1
EP1497251A1 EP03714898A EP03714898A EP1497251A1 EP 1497251 A1 EP1497251 A1 EP 1497251A1 EP 03714898 A EP03714898 A EP 03714898A EP 03714898 A EP03714898 A EP 03714898A EP 1497251 A1 EP1497251 A1 EP 1497251A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
halogen
group
radicals
alkenyl
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Withdrawn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
EP03714898A
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German (de)
English (en)
Inventor
Thomas Seitz
Andreas Van Almsick
Lothar Willms
Monika H. Schmitt
Thomas Auler
Hermann Bieringer
Hubert Menne
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
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Bayer CropScience AG
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Publication date
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Publication of EP1497251A1 publication Critical patent/EP1497251A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/36—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/38—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/36—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/40—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
    • C07C323/65—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfone or sulfoxide groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the invention relates to the technical field of herbicides, in particular that of the herbicides from the group of benzoylcyclohexanediones for the selective control of weeds and grasses in crops of useful plants, in particular in rice crops.
  • the object of the present invention is therefore to provide herbicidally active compounds having improved herbicidal properties compared to the compounds disclosed in the prior art.
  • X 1 denotes a divalent unit from the group O, S (0) n , NH, NR 2 ;
  • X 2 denotes a straight-chain or branched, by w radicals from the group
  • X 3 represents oxygen, sulfur or NOR 3 ;
  • R 1a , R 1b and R c independently of one another denote H, mercapto, N0 2 , halogen, cyano, thiocyanato, (CC 6 ) -alkyl-CO-0, (CrC 6 ) -alkyl-S (0) n -0, (dC 6 ) - alkyl-S (0) n , (CrC 6 ) -haloalkyl-S (0) n, (C 3 -C 7 ) cycloalkyl-S (0) n , di- (dC 6 ) alkyl -N- S0 2 , (-C-C 6 ) -alkyl-S0 2 -NH, (C ⁇ -C 6 ) -alky!
  • D represents oxygen or sulfur
  • R 2 , R 3 independently of one another are hydrogen, each substituted by v radicals from the group CN, N0 2 and halogen (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) -Alkynyl, (C 3 -C 9 ) -cycloalkyl, (C 3 -C 9 ) -cycloalkenyl, (d- C 6 ) -alkyl- (C 3 -C 9 ) -cycloalkyl, (C ⁇ -C 6 ) - Alkyl- (C 3 -C 9 ) -cycloalkenyl, (C 2 -C 6 ) -alkenyl- (C 3 - C 9 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl- (C 3 - C 9 ) -cycloalkyl, (C 2 -C 6 ) -al
  • R 4 represents OR 7 , (dC 4 ) alkylthio, halogen (dC 4 ) alkylthio, (C 2 -C 4 ) alkenylthio, halogen (C 2 -C 4 ) alkenylthio, (C 2 -C 4 ) -Alkynylthio, halogen- (C 2 -C 4 ) -alkynylthio, (CC 4 ) -alkyl-SO, halogen- (CC 4 ) -alkyl-SO, (C 2 -C 4 ) -alkenyl-SO, halogen- (C 2 -C 4 ) -alkenyl-SO, (C 2 -C 4 ) -alkynyl-SO, halogen- (C 2 -C 4 ) -alkynyl-SO, (CC 4 ) -alkyl-S0 2 , halogen- (-C-C 4 ) alky
  • R 5 denotes hydrogen, in each case by v radicals from the group halogen, (-CC 4 ) -alkylthio and (-CC 4 ) -alkoxy-substituted tetrahydropyranyl-3, tetrahydropyranyl-4, tetrahydrothiopyranyl-3,
  • R 6 represents H, halogen, CN, N0 2 , (CC 4 ) alkyl or halo (dC 4 ) alkyl;
  • R 7 denotes H, (CC 4 ) -alkyl, halogen- (-C-C 4 ) -alkyl, (dC 4 ) -alkoxy- (C ⁇ -C 4 ) -alkyl, CHO, (CC 4 ) -alkyl-CO, (-C-C 4 ) -alkoxy-CO, (dC 4 ) -alkyl-NH-CO, di- (dC 4 ) - alkyl-N-CO, ( dC 4 ) -Alkyl-S0 2 , Haloge ⁇ - (CC 4 ) -alkyl-S0 2 , each by v radicals from the group (CC 4 ) -alkyl, halogen- (CC 4 ) -alkyl, (dC 4 ) -alkoxy , Halogen- (dC 4 ) - alkoxy, halogen, CN and N0 2 substituted benzoyl or phenyl-S
  • Y is a divalent unit from the group O, S, NH, (-C-C 6 ) alkyl-N,
  • Z denotes a direct bond or a divalent unit from group O
  • n and n each independently represent 0, 1 or 2; p is independently 0 or 1; v represents 0, 1, 2 or 3; w and x each independently represent 0.1, 2, 3 or 4, z means 1, 2, 3 or 4 where w and x should not be zero at the same time.
  • the 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 formula (I) contain an acidic proton which can be removed by reaction with a base.
  • bases are, for example, hydrides, hydroxides and carbonates of alkali and alkaline earth metals, such as lithium, sodium, potassium, magnesium and calcium, and also ammonia and organic amines such as triethylamine and pyridine.
  • Such salts are also the subject of the invention.
  • alkyl radicals having more than two carbon atoms can be straight-chain or branched.
  • Alkyl radicals mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl.
  • the carbon chain X 2 can also, depending on the number of its C- Atoms may be straight or branched.
  • Cycloalkyl means a carbocyclic, saturated ring system with three to nine 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 cycloalkyl-alkenyl
  • the former radical can be located at any position of the latter.
  • Halogen means fluorine, chlorine, bromine or iodine.
  • Haloalkyl, -alkenyl and -alkynyl are partially 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 , CH2CH2CI;
  • Haloalkoxy is, for example, OCF 3 , OCHF 2f OCH 2 F, CF3CF2O, 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.
  • the link can, if chemically possible, to any Position of 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-isothiazolez , 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4th -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, biphenyl and phenanthryl, preferably phenyl.
  • the link can basically be made 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-
  • 6-membered heteroaryl examples include 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimdinyI, 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 compounds of the formula (I) can be present as stereoisomers. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur.
  • Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, e.g. obtained 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.
  • R 2 , R 3 independently of one another are hydrogen, each substituted by v radicals from the group CN, N0 2 and halogen (dC 6 ) -
  • Preferred compounds of the general formula (I) are those in which X 1 is oxygen or S (0) n; R 1a , R 1b independently of one another F, Cl, Br, N0 2 , CF 3 , CH 3 , CH 3 S, CH 3 0, CH 3 S0 2 , EtS0 2 , CF 3 CH 2 S0 2 or CyclopropyI-S0 2 ;
  • R 2 , R 3 independently of one another are hydrogen, in each case substituted by v radicals from the group CN, NO 2 and halogen (C 1 -C 6 ) -
  • Cycloalkyl straight-chain or branched [C (R 6 ) 2 ] z - [OC (R 6 ) 2 ] w - [0-C (R 6 ) 2 ] x -R 6 , each by v radicals from the group CN, N0 2 , halogen, (-C-Ce) -alkyl- (D) P and
  • R 4 OR 7 (CC 4 ) -alkylthio, (C 2 -C 4 ) -alkenylthio, (dC 4 ) -alkyl-S0 2 , halogen, CN,
  • Y, Z each CH 2 ; v, w and x are each independently 0, 1 or 2; z mean 1 or 2.
  • R 4 is alkylsulfinyl, haloalkylsulfinyl, alkenylsulfinyl, haloalkenylsulfinyl, alkynylsulfinyl, halosulfonylsulfonyl, alkylsulfonylsulfyl, alkylsulfonyl Alkenylsulfonyl, haloalkenylsulfonyl, alkynylsulfonyl, optionally substituted phenylthio or haloalkynylsulfonyl.
  • an oxidation reagent such as m-chloroperoxybenzoic acid, peroxyacetic acid, hydrogen peroxide and potassium peroxymonosulfate
  • Compounds of the formula (IVa) can, for example, according to Scheme 5, from compounds of the formula (VII) in which L 2 represents a group such as chlorine and L 1 represents a group such as chlorine, bromine, mesyl or tosyl, with organometallic reagents of the formula ( VIII, in which Met stands for a metal such as magnesium, cadmium or zinc, can be produced according to methods known per se, such methods being, for example, from Organic Reactions 8 (1954) 28; J. Org. Chem. 28 (1963) 630; Zh Org. Khim. 27 (1991) 7, 1431.
  • 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, rhizomes 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 and Sorghum as well as perennial Cyperus species are well recorded.
  • the spectrum of activity extends to species such as Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria and Abutilon 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 used by the inventive Active ingredients are also superbly combated. 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 according to the invention show an excellent action against Amaranthus retroflexus, Avena sp., Echinochloa sp., Cyperus serotinus, Lolium multiflorum, Setaria viridis, Sagittaria pygmaea, Scirpus juncoides, Sinapis sp. and Stellaria media.
  • 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. They are particularly well tolerated in wheat, corn and rice. 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 relate to 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.
  • B. of cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • 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,
  • transgenic crops with modified fatty acid composition in principle, numerous molecular biological techniques with which new transgenic plants with modified properties can be produced are known; see, e.g., Sambrook et al., 1989, Molecular Cloning, A LaboratoiN Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker “Gene and Clones”, VCH Weinheim 2nd edition 1996 or Christou, "Trends in Plant Science” 1 (1996) 423-431).
  • 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 cells 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 gene product mentioned above.
  • 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 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.
  • 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 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 modified or specially expanded one.
  • 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. You grab regulate the plant's own metabolism and can thus be used to influence plant constituents in a targeted manner and to facilitate the harvest, such as 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 compositions which comprise compounds of the formula (I).
  • the compounds of the formula (I) can be formulated in various 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 emulsions
  • SC Suspension concentrates
  • SC dispersions based on oil or
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or inert substance, but also ionic and / or nonionic surfactants (wetting agents, dispersing agents), e.g.
  • the herbicidal active ingredients are, for example, finely ground in customary equipment, 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 butanol, 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).
  • organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents.
  • ionic and / or nonionic surfactants emulsifiers
  • emulsifiers which can be used: calcium alkylarylsulfonates such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid, alkyl aryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensate sations occur, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene such as polyoxyethylene -sorbitanfettklaer. Dusts are obtained by grinding the active ingredient with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solid substances for example 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, with 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, e.g. Polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
  • adhesives e.g. Polyvinyl alcohol, sodium polyacrylic acid or mineral oils
  • 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 substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, 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.
  • 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.
  • 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; amitrol; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; azimsulfurone (DPX-A8947); aziprotryn; barban; BAS 516 H, ie 5-fluoro-2-phen
  • the formulations present in the commercial form are diluted in the usual way, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water. Preparations in the form of dust, ground granules or scattering granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the required application rate of the compounds of formula (I) varies. It can fluctuate within wide limits, e.g. between 0.001 and 1.0 kg / ha or more active substance, but is preferably between 0.005 and 750 g / ha.
  • the starting compound ethyl 2,4-dibromo-3-hydroxy-benzoate was prepared in accordance with US Pat. No. 5,026,896, and 2-chloro-3-hydroxy-4-ethylsulfonyl-benzoic acid was prepared in accordance with EP-A 0 195 247.
  • RT room temperature.
  • R f retention value.
  • Step 1 2-chloro-3-hydroxy-4-ethylsulfonyl-benzoic acid methyl ester 33.0 g (124.7 mmol) of 2-chloro-3-hydroxy-4-ethylsulfonyl-benzoic acid were dissolved in 1300 ml of methanol. 174 ml (3263 mmol) of conc. H 2 S0 4 was added dropwise, and the mixture was heated under hindfoot for 5 h. The reaction mixture was concentrated and the residue was taken up in CH 2 CI 2 . It was washed with water, dried over Na 2 S0 4 and concentrated completely.
  • Step 2 2-chloro-3- (methylcarbonyl-methoxy) -4-ethylsulfonyl-benzoic acid methyl ester 0.922 g (7.2 mmol) K 2 CO 3 , 0.179 g (1.10 mmol) Kl and 0.454 g (4.7 mmol) chloroacetone were added 30 ml DMF submitted.
  • 1,000 g (3.6 mmol) of methyl 2-chloro-3-hydroxy-4-ethylsulfonylbenzoate were added, and the mixture was heated at 80 ° C. for 4 h. The mixture was then poured onto water and extracted with diisopropyl ether.
  • Step 3 2-chloro-3- (methylcarbonyl-methoxy) -4-ethylsulfonyl-benzoic acid 0.870 g (2.60 mmol) of 2-chloro-3- (methylcarbonyl-methoxy) -4-ethylsulfonyl-benzoic acid methyl ester were mixed in a mixture of 10 ml Dissolved THF and 10 ml of water and mixed with 0.114 g (2.90 mmol) NaOH. The mixture was stirred at RT for 12 h and concentrated completely. The residue was taken up in water and treated with 6 N HCl and extracted with CH 2 CI 2 .
  • Step 4 ((3-oxo-1-cyclohexenyl) -2-chloro-3- (methylcarbonyl-methoxy) -4-ethylsulfonyl) -benzoate 0.295 g (0.9 mmol) 2-chloro-3- (methylcarbonyl-methoxy) - 4-ethylsulfonylbenzoic acid, 0.113 g (1.0 mmol) cyclohexane-1, 3-dione, 0.180 g (0.9 mmol) N ' - (3-dimethylaminopropyl) -N-ethylcarbodiimide hydrochloride and 0.001 g dimethylaminopyridine were in 25 ml CH 2 CI 2 2 h at RT stirred.
  • Step 5 (2-chloro-3- (methylcarbonyl-methoxy) -4-ethylsulfonyl-benzoyl) - cyclohexane-1,3-dione 0.290 g (approx. 0.70 mmol) ((3-oxo-1-cyclohexenyl) -2 -Chlor-3- (methylcarbonyl-methoxy) -4-ethyl! Sulfonyl benzoate was dissolved in 10 ml of acetonitrile. 3 drops of acetone cyanohydrin and 0.120 g (1.20 mmol) of triethylamine were added.
  • Step 1 ethyl 2,4-dibromo-3- (ethylcarbonyl-methoxy) -benzoate 0.853 g (6.20 mmol) K 2 C0 3 , 0.154g (0.90 mmol) Kl and 1,000 g (3.10 mmol) 2,4-dibromo-3 Hydroxy-benzoic acid ethyl ester were placed in 10 ml of DMF. At RT, 0.621 g (3.70 mmol) of 1-bromo-2-butanone were added and then heated to 80 ° C. for 4 h. The mixture was then poured onto water and extracted with diisopropyl ether.
  • Step 2 2,4-dibromo-3- (ethylcarbonyl-methoxy) -benzoic acid 1,280 g (3.20 mmol) ethyl 2,4-dibromo-3- (ethylcarbonyl-methoxy) -benzoate were dissolved in 15 ml of THF and 15 ml of water and 0.143 g (3.6 mmol) of NaOH were added. The mixture was stirred at RT for 12 h and concentrated completely. The residue was taken up in water and treated with 6 N HCl. The precipitate was filtered off and dried. 2,4-Dibromo-3- (ethylcarbonyl-methoxy) benzoic acid was obtained in the form of a white solid. Yield: 0.86g (69% of theory)
  • Step 3 (3-Oxo-1-cyclohexenyl) - 2,4-dibromo-3- (ethylcarbonyl-methoxy) - benzoate 0.415 (1.10 mmol) 2,4-dibromo-3- (ethylcarbonyl-methoxy) -benzoic acid, 0.140 g (1.20 mmol) of cyclohexane-1,3-dione, 0.222 g (1.10 mmol) of N ' - (3-dimethylaminopropyl) - N-ethylcarbodiimide hydrochloride and 0.001 g of dimethylaminopyridine were stirred in 30 ml of CH 2 Cl 2 for 3 h at room temperature.
  • Step 4 2,4-dibromo-3- (ethylcarbonyl-methoxy) -cyclohexane-1,3-dione 0.280 g (approx. 0.60 mmol) ((3-oxo-1-cyclohexenyl) -2,4-dibromo-3 - (ethylcarbonyl methoxy) benzoate was dissolved in 5 ml of acetonitrile and 3 drops were added Acetone cyanohydrin, 0.012 g (0.2 mmol) KCN and 0.105 g (1.00 mmol) triethylamine were added.
  • Ketone-cyanhodrin R f (ethyl acetate): 0.29 1 H-NMR: ⁇ [CDCI 3 ] 1.16 (t, 3H), 2.05 (m, 2H), 2.45 (m, 2H), 2.75-2.89 (m, 4H),
  • Step 1 ethyl 2,4-dibromo-3- (2-ethoxyimino-propyloxy) benzoate 1.00 g (2.60 mmol) ethyl 2,4-dibromo-3- (methylcarbonyl-methoxy) benzoate (made from 2,4-dibromo- 3-hydroxy-benzoic acid ethyl ester and chloroacetone) analogous to preparation a) above, step 1) and 0.614 g (5.80 mmol) of Na 2 CO were placed in 10 ml of methanol.
  • Step 3 ((3-Oxo-1-cyclohexenyl) -2,4-dibromo-3- (2-ethoxyimino-propyloxy) benzoate 0.280 (0.70 mmol) 2,4-dibromo-3- (2-ethoxyimino-propyloxy) ) -benzoic acid, 0.087 g (0.80 mmol) cyclohexane-1, 3-dione, 0.139 g (0.70 mmol) N ' - (3-dimethylaminopropyl) - N-ethylcarbodiimide hydrochloride and 0.001 g dimethylaminopyridine were added in 15 ml CHCl 2 for 3 hours RT.
  • Step 4 2,4-dibromo-3- (2-ethoxyimino-propyloxy) cyclohexane-1,3-dione
  • Step 1 2-chloro-3- (2-allyloxyimino-propyloxy) -4-ethanesulfonyl-benzoic acid, methyl ester
  • Step 2 2-chloro-3- (2-allyloxyimino-propyloxy) -4-ethanesulfonyl-benzoic acid 0.540 g (approx. 1.40 mmol) of 2-chloro-3- (2-allyloxyimino-propyloxy) -4-ethanesulfonyl-benzoic acid methyl ester were reacted with 0.061 g (1.50 mmol) NaOH analogously to preparation c). Yield: 0.526 g (approx.
  • Step 3 ((3-Oxo-1-cyclohexenyl) -2-chloro-3- (2-allyloxyimino-propyloxy) -4-ethanesulfonyl-benzoate 0.526 (1.40 mmol) of 2-chloro-3- (2-allyloxyimino-propyloxy ) -4-ethanesulfonyl-benzoic acid were prepared analogously to 0.173 g (1.50 mmol) cyclohexane-1,3-dione, 0.274 g (1.40 mmol) N '- (3-dimethylaminopropyl) -N-ethylcarbodiimide hydrochloride and 0.002 g dimethylaminopyridine c) implemented.
  • Step 4 2-chloro-3- (2-allyloxyimino-propyloxy) -4-ethylsulfonyl-cyclohexane-1,3-dione 0.510 g (approx. 1.10 mmol) ((3-oxo-1-cyclohexenyl) -2-chloro -3- (2-allyloxyimino-propyloxy) -4-ethanesulfonyl benzoate were reacted with 3 drops of acetone cyanohydrin, 0.022 g (0.3 mmol) of KCN and 0.187 g (1.80 mmol) of NEt 3 analogously to preparation c).
  • R 1a _ Cl
  • R 1b SO 2 Me
  • R 1c H
  • R 1a Cl
  • R 1b SO 2 Me
  • 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 it in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the general formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as a wetting and dispersing agent 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 attritor.
  • 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 emulsifier.
  • a water-dispersible granulate is obtained by mixing 75 parts by weight of a compound of the general formula (I), 10 "calcium lignosulfonic acid,
  • polyvinyl alcohol and 7 kaolin mixes, grinds on a pin mill and granulates the powder in a fluidized bed by spraying water as granulating liquid.
  • a water-dispersible granulate is also obtained by adding 25 parts by weight of a compound of the general formula (I), 5 "2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium,
  • the compounds of Examples Nos. 3.3 and 1.8 at a dosage of 320 g / ha show a 90-100% activity against Chenopodium album, Echinocloa crus galli and Veronica persica.
  • the compounds of examples Nos. 4.19 and 4.98 show a 90- at 80 g / ha 100% activity against Stellaria media, Chenopodium album and Matricaria inodora.

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Abstract

L'invention concerne des dérivés de benzoylcyclohexanediones de formule (I) et leur utilisation en tant qu'herbicides. Dans cette formule générale (I), R<1a>, R<1b>, R<1c>, R<2>, R<3>, R<4> et R<5> représentent différents groupes, X<1> est un atome ponté, X<2> une chaîne carbonée et X<3> un atome de chalcogène ou un groupe oximino.
EP03714898A 2002-04-10 2003-03-28 Benzoylcyclohexandiones substitues par 3-ceto ou 3-oxime-ether Withdrawn EP1497251A1 (fr)

Applications Claiming Priority (3)

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DE10215723A DE10215723A1 (de) 2002-04-10 2002-04-10 3-Keto oder 3-Oximether substituierte Benzoylcyclohexandione
DE10215723 2002-04-10
PCT/EP2003/003250 WO2003084912A1 (fr) 2002-04-10 2003-03-28 Benzoylcyclohexandiones substitues par 3-ceto ou 3-oxime-ether

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BR112012001940B1 (pt) 2009-07-29 2018-06-19 Bayer Intellectual Property Gmbh 2-(3-alquiltiobenzoil) ciclohexanodionas, produtos herbicidas e sua utilização como herbicidas
WO2012010575A1 (fr) 2010-07-21 2012-01-26 Bayer Cropscience Ag (4-halogénoalkyle-3-thiobenzoyle) cyclohexandiones et leur utilisation comme herbicides
WO2012010574A1 (fr) 2010-07-21 2012-01-26 Bayer Cropscience Ag (4-trifluorométhyle-3-thiobenzoyle) cyclohexandiones et leur utilisation comme herbicides
US8455657B2 (en) * 2010-12-28 2013-06-04 Bayer Cropscience Ag Process for the preparation of 3-alkylsulfinylbenzoyl derivatives
BR112019014962A2 (pt) 2017-01-20 2020-04-28 Hokko Chem Ind Co herbicida e derivado de isoxazolina-5-ona contendo o mesmo como ingrediente ativo
CN115232039B (zh) * 2022-09-21 2023-01-13 启农生物科技(北京)有限公司 一种3-甲基-2-氯-4-甲基磺酰基苯甲酸甲酯的制备方法
WO2024153074A1 (fr) * 2023-01-16 2024-07-25 沈阳万菱生物技术有限公司 Composés de thioéther cyclohexényl(phényltétra-substitué), leur procédé de préparation et leur utilisation

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DE10215723A1 (de) 2003-10-30
AR039397A1 (es) 2005-02-16
CA2481808A1 (fr) 2003-10-16
TW200307504A (en) 2003-12-16
BR0309092A (pt) 2005-02-09
AU2003219112A1 (en) 2003-10-20
US6930208B2 (en) 2005-08-16

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