EP2046781A2 - Furyl-sulfonylamino(thio)carbonyl-triazoline(thi)ones substituées - Google Patents

Furyl-sulfonylamino(thio)carbonyl-triazoline(thi)ones substituées

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Publication number
EP2046781A2
EP2046781A2 EP07765059A EP07765059A EP2046781A2 EP 2046781 A2 EP2046781 A2 EP 2046781A2 EP 07765059 A EP07765059 A EP 07765059A EP 07765059 A EP07765059 A EP 07765059A EP 2046781 A2 EP2046781 A2 EP 2046781A2
Authority
EP
European Patent Office
Prior art keywords
substituted
cyano
alkyl
fluorine
chlorine
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Withdrawn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
EP07765059A
Other languages
German (de)
English (en)
Inventor
Christian Waldraff
Martin Hills
Heinz Kehne
Chris Rosinger
Ernst Gesing
Klaus-Helmut Müller
Dieter Feucht
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP2046781A2 publication Critical patent/EP2046781A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to novel substituted furyl-sulfonylamino (thio) carbonyl-triazolin-(thi) ones, to processes and novel intermediates for their preparation and to their use as herbicides.
  • Q 1 is O (oxygen) or S (sulfur),
  • Q 2 is O (oxygen) or S (sulfur)
  • R a represents hydrogen, cyano, nitro, halogen or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkynyl, alkenyloxy or alkynyloxy,
  • R b is hydrogen, cyano, nitro, halogen or each optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkynyl, alkenyloxy or alkynyloxy,
  • R c is CO-Y
  • R 6 represents hydrogen, hydroxyl, amino, cyano, alkylideneamino or each optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkylamino, alkylcarbonylamino, alkenyloxy, dialkylamino, cycloalkyl, cycloalkylamino, cycloalkylalkyl, aryl or arylalkyl,
  • R 7 is hydrogen, hydroxyl, mercapto, amino, cyano, halogen or in each case optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, alkylcarbonylamino, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino, alkynylamino, dialkylamino, aziridino, pyrrolidino , Piperidino, morpholino, cycloalkyl, cycloalkenyl, cycloalkyloxy,
  • R 7 and R 6 together represent optionally branched alkanediyl
  • Y stands for one of the groupings OR 8 or N (R 9 R 10 ), where
  • R 8 is in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl
  • R 9 is hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl
  • R 9 is hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl
  • R 10 is hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
  • Saturated or unsaturated hydrocarbon moieties such as alkyl, alkanediyl, alkenyl or alkynyl, are also in linkages with heteroatoms, such as in alkoxy
  • Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substitution the substituents may be the same or different.
  • Q 1 is preferably O (oxygen) or S (sulfur).
  • Q 2 is preferably O (oxygen) or S (sulfur).
  • R a is preferably hydrogen, cyano, nitro, halogen, in each case optionally substituted by cyano, halogen or (C 1 -CO-Alkoxy substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl group, or in each case optionally substituted by cyano or halogen alkenyl, alkynyl, alkenyloxy or alkynyloxy each having 2 to 6 carbon atoms in the alkenyl or alkynyl group.
  • R b is preferably hydrogen, cyano, nitro, halogen, in each case optionally cyano, halogen or (Ci-C 4 ) alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl group, or each optionally substituted by cyano or halogen alkenyl, alkynyl, alkenyloxy or alkynyloxy each having 2 to 6 carbon atoms in the alkenyl or alkynyl group.
  • R c is preferably CO-Y
  • R 6 is preferably hydrogen, hydroxy, amino, cyano, for (C 2 -C 10 ) -
  • Alkylideneamino optionally substituted by fluorine, chlorine, bromine, cyano, (C 1 -C 4 ) -alkoxy, or substituted alkyl having 1 to 6 carbon atoms, in each case optionally substituted by fluorine, chlorine and / or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, in each case optionally by fluorine, chlorine, bromine,
  • Cyano (C 1 -CJ -alkoxy or substituted alkoxy, alkylamino or alkyl carbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, for alkenyloxy having 3 to 6 carbon atoms, for dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, in each case optionally by fluorine, chlorine, bromine, cyano and / or (C 1 -C 4 ) -
  • R 7 is preferably hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, optionally substituted by fluorine, chlorine, bromine, cyano, (C 1 -
  • (C r C4) alkyl trifluoromethyl, (C r C 4) -alkoxy and / or (C 1 -C 4) - alkoxycarbonyl, substituted aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino or arylalkylamino having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part.
  • R 6 and R 7 are also preferably together optionally branched alkanediyl having 3 to 6 carbon atoms.
  • Y preferably represents one of the groupings OR 8 or N (R 9 R 10 ), where
  • R 8 is optionally substituted by cyano, halogen or (C- ⁇ -C 4) -alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents optionally cyano- or halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, represents in each case optionally by cyano, halogen or (Ci-C 4 ) -
  • R 9 is hydrogen or optionally cyano, halogen or (Ci-C 4 ) - alkoxy-substituted alkyl having 1 to 6 carbon atoms, each optionally substituted by cyano or halogen alkenyl or alkynyl each having 2 to 6 carbon atoms, each optionally optionally Cyano, halogen or (Ci-C 4 ) alkyl substituted cycloalkyl or
  • Cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by nitro, cyano, halogen, (Ci-C 4 ) alkyl or (C 1 -C 4 ) - alkoxy substituted aryl or Arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4
  • Alkyl part is available, and
  • R 10 is hydrogen or optionally cyano, halogen or (Ci-C 4 ) -
  • Alkyl part is.
  • Q 1 particularly preferably represents O (oxygen) or S (sulfur).
  • Q 2 is particularly preferably O (oxygen) or S (sulfur).
  • R a particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,
  • R b particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, in each case optionally cyano, fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or for in each case optionally cyano, fluorine or chlorine-substituted propenyl, Butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy.
  • R c is particularly preferably CO-Y
  • R 6 particularly preferably represents hydrogen, hydroxyl, amino, in each case optionally fluorine, chlorine, cyano, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for each optionally substituted by fluorine, chlorine and / or bromine substituted ethenyl, propenyl, butenyl, propynyl or butynyl, in each case optionally
  • R 7 particularly preferably represents hydrogen, chlorine, bromine, in each case optionally by fluorine, chlorine, cyano, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, in each case optionally substituted by fluorine, chlorine and / or bromine ethenyl, propenyl, butenyl , Ethynyl, propynyl or butynyl, in each case optionally substituted by fluorine, chlorine, cyano, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n
  • R 6 and R 7 are also particularly preferably together for trimethylene (propane-1, 3-diyl), tetramethylene (butane-1, 4-diyl) or pentamethylene (pentane-1, 5-diyl).
  • Y is particularly preferably one of the groupings OR 8 or N (R 9 R 10 ), where
  • R 8 is in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, in each case optionally substituted by cyano, fluorine or chlorine Propenyl, butenyl, propynyl or butynyl, in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, cyclopropyl, cyclobutyl, cyclopentyl,
  • Cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl in each case optionally by cyano, fluorine, chlorine, Bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, or in each case optionally by cyano, fluorine, chlorine, bromine, methyl , Ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy substituted heterocyclyl or heterocyclylmethyl, wherein the
  • Heterocyclyl group is in each case selected from the series oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl,
  • R 9 is hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, in each case optionally by cyano, fluorine or chlorine-substituted propenyl, butenyl, propynyl or butynyl, in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, in each case optionally by cyano, fluorine, chlorine , Bromo, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy,
  • Heterocyclyl or heterocyclylmethyl wherein the heterocyclyl group is selected in each case from the series oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, and
  • R 10 is hydrogen, in each case optionally by cyano, fluorine, chlorine,
  • Q 1 very particularly preferably represents O (oxygen).
  • Q 2 is most preferably O (oxygen).
  • R a very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine or in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl.
  • R b is very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine or in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl.
  • R c is very particularly preferably CO-Y
  • R 6 is very particularly preferably in each case optionally substituted by fluorine, chlorine,
  • Propinyl for each optionally substituted by fluorine, chlorine, methoxy or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, for dimethylamino, or cyclopropyl.
  • R 7 very particularly preferably represents hydrogen, chlorine, bromine, in each case optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, in each case optionally Ethenyl, propenyl, butenyl, propynyl or butynyl which is fluorine- or chlorine-substituted, methoxy optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, propenyloxy, propynyloxy, propenylthio, propynylthio, propynylthio
  • Y is most preferably the group OR 8 , where
  • R 8 is in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl.
  • the invention preferably also the sodium, potassium,
  • Preferred compounds according to the invention are those compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.
  • Particularly preferred compounds according to the invention are those compounds of the formula (I) in which a combination of the meanings listed above as being particularly preferred is present.
  • a very particularly preferred group are the compounds of the formula (IA)
  • R 2 is R a and R 5 is R b and wherein Q 1 , Q 2 , R a , R b , R 6 , R 7 and Y have the meanings given above as being preferred, particularly preferred or most particularly preferred.
  • R 2 is particularly preferably hydrogen, methyl, trifluoromethyl, ethyl, propyl, isopropyl and R 5 is hydrogen or methyl, and Q 1 , Q 2 , R 6 , R 7 and Y have the meanings given above as very particularly preferred ,
  • R 4 is R a and R 5 is R b and wherein Q 1 , Q 2 , R a , R b , R 6 , R 7 and Y have the meanings given above as being preferred, particularly preferred or very particularly preferred.
  • R 4 is very particularly preferably hydrogen, methyl, trifluoromethyl, ethyl, propyl, isopropyl and R 5 is hydrogen or methyl and Q 1 , Q 2 , R 6 , R 7 and 'have the meanings given above as very particularly preferred.
  • R 4 is R a and R 5 is R b and wherein Q 1 , Q 2 , R a , R b , R 6 , R 7 and Y have the meanings given above as being preferred, particularly preferred or very particularly preferred.
  • R 4 is very particularly preferably hydrogen, methyl, trifluoromethyl, ethyl, propyl, isopropyl and R 5 is hydrogen or methyl, and Q 1 , Q 2 , R 6 , R 7 and Y have the meanings given above as very particularly preferred ,
  • novel substituted furyl-sulfonylamino (thio) carbonyl-triazoline (thi) ones of the general formula (I) have interesting biological properties. They are characterized in particular by strong herbicidal activity.
  • R a , R D and R c are as defined above,
  • Z is halogen, alkoxy, aryloxy or arylalkoxy
  • Q 2 , R 6 and R 7 have the abovementioned meaning, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or if
  • R a , R b and R c have the abovementioned meaning, with triazoline (thi) ones of the general formula (V)
  • R a , R b and R c are as defined above,
  • Q 1 , R a , R b and R c have the abovementioned meaning and Z represents halogen, alkoxy, aryloxy or arylalkoxy,
  • reaction sequence in process (b) according to the invention can be outlined by the following formula scheme:
  • reaction sequence in process (d) according to the invention can be outlined by the following formula scheme:
  • reaction sequence in the process (e) according to the invention can be outlined by the following formula scheme:
  • R a have, R b and R c preferably or in particular have those meanings which (I) above in connection with the description of the compounds of the general formula as preferred or as particularly preferred for R a, R b and R c have been indicated.
  • R a , R b and R c are as defined above,
  • ammonia or with ammonium salts such as ammonium acetate or ammonium carbonate
  • a diluent such as water and / or methylene chloride
  • the starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf., EP-A-341 489, EP-A-422 469, EP-A-425 948, EP-A-431 291, EP-A-507171, EP-A-534 266).
  • the starting materials of the general formula (IV) can be prepared by conventional methods, for example by phosgenation of corresponding furan-sulfonamides of the formula (II) by customary methods.
  • the starting materials of the general formula (V) are known and / or can be prepared by processes known per se (cf., EP-A-341 489, EP-A-422 469, EP-A-425 948, EP-A-431 291, EP-A-507171, EP-A-534 266).
  • R a , R b and R c preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the general formula (I) according to the invention or as being particularly preferred for R a , R b and R c have been indicated.
  • the substituted furan-sulfonic acid chlorides of the general formula (VI) are known and / or can be prepared by processes known per se (cf., WO-A-2003/029245, WO-A-2003/082777, WO-A-2004/100946 ).
  • the in process (d) for the preparation of compounds of general formula (I) as starting materials to be used triazoline (thi) on- (thio) - carboxamides are generally defined by the formula (VIII).
  • Q 1 , Q 2 , R 6 and R 7 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of general formula (I) according to the invention preferably or as particularly preferred Q 1 , Q 2 , R 6 and R 7 have been specified.
  • the starting materials of the general formula (VIII) can be prepared by processes known per se.
  • the starting materials of the general formula (IX) can be prepared by processes known per se.
  • Suitable diluents are virtually all inert organic solvents. These include preferably aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and Dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone, esters such as methyl acetate and ethyl acetate, nitriles such as acetonitrile
  • reaction auxiliaries in the processes (a), (b), (c), (d) and (e) according to the invention it is possible to use all acid binders customarily used for such reactions.
  • acid binders customarily used for such reactions.
  • alkali metal hydroxides e.g. Sodium and potassium hydroxides
  • alkaline earth hydroxides e.g.
  • reaction temperatures in the processes (a), (b), (c), (d) and (e) according to the invention can be varied within a substantial range. In general, one works at temperatures between -20 0 C and + 15O 0 C, preferably at temperatures between 0 0 C and + 100 ° C.
  • the particular starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the components used in each case in a larger excess.
  • the reactions are generally carried out in a suitable diluent in the presence of a Acid acceptor performed, and the reaction mixture is stirred for several hours at the temperature required.
  • the work-up is carried out in the processes (a), (b), (c), (d) and (e) according to the invention in each case by customary methods (compare the preparation examples).
  • Salts may optionally be prepared from the compounds of the general formula (I) according to the invention.
  • Such salts are obtained in a simple manner by customary salt formation methods, for example by dissolving or dispersing a compound of formula (I) in a suitable solvent, e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base.
  • a suitable solvent e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene
  • the salts can then - be isolated by concentration or suction - optionally after prolonged stirring.
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and especially as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides essentially depends on the amount used.
  • the compounds of the formula (I) according to the invention and their salts, referred to hereinafter together as compounds of the formula (I) according to the invention, have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even difficult to control perennial weeds, which expel from rhizomes, rhizomes or other permanent organs, are well detected by the active ingredients. It does not matter whether the substances are applied in the pre-sowing, pre-emergence or postemergence process.
  • the compounds according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage stage, But then they stop growing and finally die off after three to four weeks.
  • the compounds of the invention have excellent herbicidal activity against mono- and dicotyledonous weeds
  • Crops of economically important crops such as e.g. Wheat, barley, rye, rice, maize, sugar beet, cotton and soya only marginally or not at all damaged.
  • the present compounds are very well suited for the selective control of undesired plant growth in agricultural crops.
  • the substances according to the invention have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant ingredients and facilitate harvesting, eg by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures, as storage can be reduced or completely prevented. Due to their herbicidal and plant growth regulatory properties, the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by 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 z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
  • Preference is given to the use of the compounds of the formula (I) according to the invention or salts thereof in economically important transgenic crops of useful and ornamental plants, eg.
  • Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
  • new plants which have modified properties in comparison to previously occurring plants consist, for example, in classical breeding methods and the production of mutants.
  • new plants with altered properties can be generated by means of genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624).
  • genetic modifications of crop plants have been described for the purpose of modifying the starch synthesized in the plants (for example WO 92/11376, WO 92/14827, US Pat.
  • Glufosinate see, for example, EP-A-0242236, EP-A-242246) or glyphosate (WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A-5013659) are resistant, transgenic crops, for example, cotton, with the ability
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins (Bt toxins) that make the plants resistant to certain pests (E P-A-0142924, EP-A-0193259).
  • Transgenic crops with modified fatty acid composition Bacillus thuringiensis toxins (Bt toxins) that make the plants resistant to certain pests (E P-A-0142924, EP-A-0193259).
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences.
  • z For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • adapters or linkers can be attached to the fragments.
  • Gene product can be obtained, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present 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 are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
  • the compounds (I) according to the invention can be used in transgenic cultures which are resistant to herbicides from the group of sulfonylureas, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active substances.
  • the invention therefore also relates to the use of the compounds of the formula (I) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • 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 provides herbicidal and plant growth-regulating agents which contain 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 predetermined.
  • Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, and elevator Adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW emulsions
  • SC suspension concentrates
  • Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agents, dispersants), eg polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate 2,2'-dinaphthylmethane-6,6 containing 1 disulfonate, sodium dibutylnaphthalene-sulfonate or else sodium oleoylmethyltaurinate.
  • the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or else 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 e.g. Butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents.
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers
  • fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products
  • alkyl polyethers sorbitan esters such as e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g. Polyoxyethylene.
  • Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solids e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding by means of commercially available bead mills and, if appropriate, addition of surfactants, as already listed above, for example, in the other formulation types.
  • Emulsions for example oil-in-water emulsions (EW)
  • EW oil-in-water emulsions
  • Granules can either be prepared by spraying the active ingredient onto adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers. Water-dispersible granules are generally prepared by the usual 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 wt .-%, preferably 0.1 to 95 wt .-%, particularly preferably 0.5 to 90 wt .-% active ingredient of the formula (I).
  • the active ingredient concentration is for example about 10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation components.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • Dusty formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.
  • the content of active ingredient is for example between 1 and 95 wt .-%, preferably between 10 and 80 wt .-%.
  • the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreeze and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent.
  • organic solvents can also be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils , Alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • Suitable solid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Lignin sulphite liquors and methylcellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers may be used in the formulations.
  • Other additives may be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the compounds of the formula (I) or salts thereof can be used as such or in the form of their formulations (formulations) with other pesticidally active substances, such as.
  • pesticidally active substances such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators
  • insecticides e.g. B. as a ready-made formulation or as tank mixes.
  • active compounds As a combination partner for the active compounds according to the invention in mixed formulations or in the tank mix, for example, known active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl-coenzyme A carboxylase, PS I 1 PS II, HPPDO, phytoene desaturase, protoporphyrinogen Oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate-3-phosphate synthetase based, can be used.
  • Such compounds and also other useful compounds with partially unknown or other mechanism of action are, for example, in Weed Research 26, 441-445 (1986), or "The Pesticide Manual", 11th edition 1997 (hereinafter also "PM") and 12.
  • herbicides which can be combined with the compounds of the formula (I) are the following active compounds (note: the compounds are either with the "common name” according to the International Organization for Standardization (ISO) or with the chemical name , optionally together with a common code number): acetochlor; acifluorfen (-sodium); aclonifen; AKH 7088, ie methyl [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and acetic acid; alachlor; alloxydim (-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; amitrol; AMS, ie ammonium sulfamate; anilofos;
  • BAS 516H i. 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; beflubutamide, benazoline (-ethyl); benfluralin; benfuresate; bensulfuron (-methyl); bensulide; bentazone; benzobicyclone, benzofenap; benzofluor; benzoylprop (-ethyl); benzthiazuron; bialaphos; bifenox; bispyribac (-sodium), bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butafenacil, butamifos; butenachlor; buthidazole; butraline; butroxydim, butylate; cafenstrole (CH-900); carbetamide; carfentrazone (-ethyl); caloxydim, CD
  • Ester derivatives e.g., clodinafop-propargyl); clomazone; clomeprop; cloproxydim; clopyralid; clopyrasulfuron (-methyl), cloransulam (-methyl), cumyluron (JC 940); cyanazine; cycloate; Cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (e.g., butyl ester, DEH-112); cyperquat; cyprazine; cyprazole; daimuron; 2,4-D, 2,4-DB, dalaphone; desmedipham; Desmetryn; di-allate; dicamba; dichlobenil; dichloroprop; diclofop and its esters such as diclofop-methyl; diclosulam, diethatyl (-ethyl); difenoxuron
  • EL 77 i. S-cyano-i, i, i-dimethylethyl, N-methyl-1H-pyrazoles, o-carboxamide; endothal; epoprodan, EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; Ethidimuron; ethiozin; ethofumesate; ethoxyfen and its esters (e.g.
  • n ' is a natural number from 0 to 5, preferably 0 to 3
  • T is a (C 1 or C 2 ) alkanediyl chain which is unsubstituted or substituted by one or two (C 1 -C 4 ) -alkyl radicals or by [(C 1 -C 3 ) -alkoxy] -carbonyl
  • W is an unsubstituted or substituted divalent heterocyclic radical from the group of unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero ring N or O atoms, at least one N atom and at most one O atom in the ring, preferably a radical from the group (W1) to (W4),
  • R 17 , R 19 are identical or different and are halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, nitro or (C 1 -C 4 ) -haloalkyl;
  • R 18 , R 20 are identical or different OR 24 , SR 24 or NR 24 R 25 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S.
  • R 25 is hydrogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6) -alkoxy or substituted or unsubstituted phenyl; R x 'is H1 (Ci-C ⁇ ) alkyl, (Ci-C8) -haloalkyl, (C 1 -C 4) alkoxy (C 1 -C 8) -alkyl, cyano or
  • R 26 is hydrogen, (Ci-C 8) -alkyl, (Ci-C8) -haloalkyl, (C 1 -C 4) - alkoxy- (C 1 -C 4) alkyl, (C 1 - C 6 ) -hydroxyalkyl, (C 3 -C 12 ) -cycloalkyl or Tn- (C 1 -
  • R 27, R 28, R 29 are identical or different hydrogen, (Ci-C 8) -alkyl, (C 1 -C 8) -
  • Haloalkyl (C 3 -C 12 ) cycloalkyl or substituted or unsubstituted phenyl;
  • R 21 is (Ci-C 4) -alkyl, (C r C4) -haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 3 -C 7) cycloalkyl , preferably dichloromethyl;
  • R 22, R 23 is identical or different hydrogen, (dC 4) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, (Ci-C 4) -haloalkyl, (C 2 -C 4) haloalkenyl, (CrC 4) alkylcarbamoyl (Ci-C 4) alkyl, (C 2 -C 4) -Alkenylcarbamoyl- (C 1 -C 4) alkyl, (C 1 -C 4 J -AIkOXy- (C 1 -C 4) - alkyl, dioxolanyl (CrC 4) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R 22 and R 23 together form a substituted or unsubstituted heterocyclic Ring, preferably an ox
  • R 30 is hydrogen, a hydrocarbon radical, a hydrocarbonoxy radical, a hydrocarbylthio radical or a heterocyclyl radical which is preferably bonded via a carbon atom, where each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more identical or different radicals from the group halogen, cyano, nitro , Amino, hydroxy,
  • Carboxy, formyl, carbonamide, sulfonamide and radicals of the formula -Z a -R a is substituted, wherein each hydrocarbon moiety preferably has 1 to 20 carbon atoms and a C-containing radical R 30 including substituents preferably 1 to 30 carbon atoms;
  • R 31 is hydrogen or (C 1 -C 10 -alkyl, preferably hydrogen, or
  • R 30 and R 31 together with the group of the formula -CO-N- denote the radical of a 3- to 8-membered saturated or unsaturated ring;
  • R 32 is identical or different and is halogen, cyano, nitro, amino, hydroxyl, carboxy, formyl, CONH 2 , SO 2 NH 2 or a radical of the formula -Z b -R b ;
  • R 33 is hydrogen or (C 1 -C 4 ) -alkyl, preferably H;
  • R 34 is identical or different and is halogen, cyano, nitro, amino, hydroxyl, carboxy, CHO, CONH 2 , SO 2 NH 2 or a radical of the formula -Z c -R c ;
  • R a is a hydrocarbon radical or a heterocyclyl radical, where each of the latter two radicals is unsubstituted or substituted by one or more identical or different radicals from the group of halogen, cyano, nitro, amino, hydroxyl, mono- and di- [(Ci-C 4 ) - alkyl] -amino, or an alkyl radical in which several, preferably 2 or 3, non-adjacent CH 2 groups are each replaced by an oxygen atom; R b , R C are the same or different or a hydrocarbon radical
  • Heterocyclylrest wherein each of the last two radicals unsubstituted or by one or more identical or different radicals selected from the group halogen, cyano, nitro, amino, hydroxyl, phosphoryl, halogeno (Ci-C 4 ) alkoxy, mono- and di- (Ci-C 4 ) -alkyl] -amino, or an alkyl radical in which several, preferably 2 or 3, not adjacent
  • CH 2 groups are each replaced by an oxygen atom;
  • Z a is a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-,
  • Z b , Z C independently of one another are a direct bond or a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-, -O-CO-, -S-CO-, -SO-, -SO 2 -, -NR * -, -SO 2 -NR * -, -NR * -SO 2 -, -CO-NR * - or -NR * -CO-, wherein the bond of the respective divalent group indicated on the right is the bond to the radical R b or R c and wherein the R * in the last-mentioned 5 radicals independently of one another are H, (C 1 -C 6 -alkyl or halo (C 1 -C 4 ) -alkyl; n is an integer from 0 to 4, preferably 0, 1 or 2, in particular O or 1, and m is an integer from 0 to 5, preferably 0, 1, 2 or 3, in
  • X 3 is CH or N;
  • R 35 is hydrogen, heterocyclyl or a hydrocarbon radical, where the latter two radicals are optionally substituted by one or more, identical or different radicals from the group halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH 2 , SO 2 NH 2 and Z a ' -R a' are substituted;
  • R 36 is hydrogen, hydroxy, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) - alkoxy, (C 2 -C 6 ) -Alkenyloxy, where the last five radicals mentioned optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, hydroxy, (Ci-C 4 ) alkyl, (CrC 4 ) alkoxy and (Ci-C 4 ) - alkylthio substitute
  • R 37 is halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH 2 , SO 2 NH 2 or Z b ' -R b' ;
  • R 38 is hydrogen, (C r C4) alkyl, (C 2 -C 4) -alkenyl or (C 2 -C 4) alkynyl;
  • R 39 is halogen, cyano, nitro, amino, hydroxy, carboxy, phosphoryl, CHO, CONH 2 ,
  • R a is a (C 2 -C 2 0) -alkyl radical whose carbon chain is interrupted one or more times by oxygen atoms, heterocyclyl or a
  • Hydrocarbon radical wherein the last two radicals are optionally substituted by one or more identical or different radicals from the group halogen, cyano, nitro, amino, hydroxy, mono- and di - [(CrC 4 ) alkyl] amino;
  • R b, R c are identical or different and are a (C 2 -C 2 o) -alkyl radical whose carbon chain one or more times interrupted by oxygen atoms, is heterocyclyl or a hydrocarbon radical, where the last two radicals optionally substituted by one or more identical or different radicals from the group halogen, cyano, nitro, amino, hydroxyl, phosphoryl, (Ci-C 4 ) -
  • Z a is a divalent unit from the group O, S, CO, CS, C (O) O, C (O) S, SO, SO 2 ,
  • Z b , Z C denote, identically or differently, a direct bond or a divalent unit from the group O, S, CO, CS, C (O) O, C (O) S, SO, SO 2 , NR d , SO 2 NR d or
  • R d ' is hydrogen, (C r C 4 ) -alkyl or (Ci-C 4 ) -haloalkyl;
  • n is an integer from 0 to 4, and in the case where X is CH, an integer of 0 to 5, and in the case where X is N, an integer of 0 to 4;
  • A is a radical from the group
  • R ⁇ and R ß independently hydrogen, (C 1 -Ce) -Al ky I, (C 3 -C 8) cycloalkyl, (C 3 -C 6) -alkenyl, (C 3 -C 6) alkynyl .
  • R ⁇ ' is hydrogen or (C r C 4 ) -alkyl
  • R a and R b independently represent hydrogen, halogen, cyano, nitro, trifluoromethyl, (C 1 -C 4) alkyl, (dC 4) -alkoxy, (C r C4) alkylthio, (Ci-C 4) -
  • R x and R ⁇ independently represent hydrogen, halogen, (C r C4) alkyl, (Ci-C 4) -
  • R n is (C 1 -C 4 ) -alkyl, phenyl or by halogen, (C 1 -C 4 ) -alkyl, methoxy, nitro or
  • R 101 is methyl, methoxy or trifluoromethoxy;
  • R 102 is hydrogen, chlorine or methyl;
  • R 103 is hydrogen, ethyl or propargyl;
  • R 104 is ethyl, cyclopropyl, isopropyl or propargyl, or R 103 and R 104 together form the group (CH 2 ) -!
  • Preferred herbicide-safener combinations comprising (A) a herbicidally effective amount of one or more compounds of formula (I) or their salts, and (B) an antidote effective amount of one or more safeners.
  • herbicidally effective amount means an amount of one or more herbicides which is suitable for negatively influencing plant growth.
  • Antidote effective amount in the context of the invention means an amount of one or more safeners, which is suitable to reduce the phytotoxic effect of crop protection agents (eg of herbicides) on crop plants.
  • crop protection agents eg of herbicides
  • EP-A-0 346 620 (AU-A 89/34951), EP-AO 174 562, EP-AO 346 620 (WO-A-91/08 202), WO-A-91/07 874 or WO-A 95/07 897 (ZA 94/7120) and the literature cited therein or can be prepared according to or analogously to the methods described therein.
  • the compounds of the formula (S-III) are described in EP-A-0 086 750, EP-A-0 94349 (US-A-4,902,340), EP-A-0,917,336 (US-A-4,881,966) and EP-A-0 492 366 and there cited literature or can be prepared according to or analogously to the methods described therein. Some compounds are further described in EP-A-0 582 198 and WO 2002/34048.
  • the compounds of formula (S-IV) are known from numerous patent applications, for example US-A-4,021,224 and US-A-4,021,229.
  • Group B (b) compounds are further described in CN-A-87 / 102,789, EP-A-365484 and The Pesticide Manual, The British Crop Protection Council and the Royal Society of Chemistry, 11th edition, Farnham 1997, known.
  • the compounds of group B (c) are described in WO-A-97/45016, those of group B (d) in WO-A-99/16744, those of group B (e) in EP-A-365484 and those of group B (g) described in EP-A-1019368.
  • herbicide-safener combinations comprising safeners of the formula (S-II) and / or (S-III) in which the symbols and indices have the following meanings:
  • R 24 is hydrogen, (C 1 -C 8 ) -alkyl, (C 3 -C 12 ) -cycloalkyl, (C 2 -C 8 ) -alkenyl and (C 2 -C 8 ) -alkynyl, where the C-containing groups may be substituted by one or more, preferably up to three, radicals R 50 ; R 50 is identical or different halogen, hydroxy, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -
  • Alkylaminocarbonyl di - ((Ci-C 6) alkyl) aminocarbonyl, (C 2 -C ⁇ ) - alkenylaminocarbonyl, (C 2 -C 6) -Alkinylaminocarbonyl, (CrC 8) - alkoxycarbonylamino, (dC ⁇ alkylaminocarbonylamino, ( CRCE) - alkylcarbonyloxy, which is unsubstituted or substituted by R 51, (C 2 -C ⁇ ) - alkenylcarbonyloxy, (C 2 -C 6) -Alkinylcarbonyloxy, (CRCs) alkylsulfonyl, phenyl,
  • R 51 is identical or different halogen, nitro, (C 1 -C 4 ) -alkoxy and unsubstituted or substituted with one or more, preferably up to three radicals R 52 phenyl;
  • R 52 is identical or different halogen, (dC 4) alkyl, (Ci-C 4) alkoxy, (Ci-C4) - haloalkyl, (Ci-C 4) haloalkoxy or nitro;
  • R ' is identical or different hydrogen, (C 1 -C 4 ) -alkyl, phenyl which is unsubstituted or substituted by one or more, preferably up to three, radicals R 52 or two radicals R' together form a (C 2 -C 6 ) - alkanediyl chain;
  • R '" is hydrogen or (C r C 4 ) alkyl; m is O, 1, 2, 3, 4, 5 or 6.
  • herbicide-safener combinations according to the invention containing safeners of the formula (S-II) and / or (S-III) in which the symbols and
  • R 24 is hydrogen, (C 1 -C 5) -alkyl or (C 3 -C 7 ) -cycloalkyl, where the above C-containing radicals are unsubstituted or mono- or polysubstituted by halogen or one or two times, preferably simply, by radicals R 50 are substituted,
  • R x ' is hydrogen or COOR 26 wherein R 26 is hydrogen, (Ci-C ⁇ ) alkyl, (CrC 8) - haloalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (C -C 6 ) -hydroxyalkyl, (C 3 -C 7 ) -cycloalkyl or tri (Ci-C 4 ) -alkylsilyl, R 17 , R 19 are identical or different halogen, methyl, ethyl, methoxy, ethoxy, (Ci or C 2 ) -haloalkyl, preferably hydrogen, halogen or (Ci or C 2 ) - haloalkyl.
  • Formula (S-II) have the following meanings: R 17 is halogen, nitro or (Ci-C 4 ) haloalkyl; n 'is O, 1, 2 or 3;
  • R 18 is a radical of the formula OR 24 ,
  • R 24 is hydrogen, (Ci-C ⁇ J-alkyl or (C 3 -C 7 ) -cycloalkyl, wherein the above
  • R 27 , R 28 , R 29 are identical or different hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 3 -C 7 ) -cycloalkyl or phenyl, which is unsubstituted or substituted by one or more of Radicals from the group halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, nitro, (C 1 -C 4 ) -haloalkyl and (C 1 -C 4 ) -haloalkoxy, and R x is hydrogen or COOR 26 , wherein R 26 is hydrogen, (C 1 -C 8 ) alkyl, (C 1 -C 8 ) haloalkyl, (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl, (i.e. CeJ-hydroxyalkyl, (C 3 -
  • R 19 is halogen or (C 1 -C 4 ) -haloalkyl
  • n ' is 0, 1, 2 or 3, wherein (R 19 J n 1 is preferably 5-Cl
  • R 20 is a radical of the formula OR 24
  • T is CH 2 or CH (COO - ((C 1 -C 3 ) alkyl)) and R 24 is hydrogen, (CrC 8) -alkyl, (C r -C 8) -haloalkyl or (C 1 -C 4 J-AIkOXy- (C 1 -C 4) - alkyl, preferably hydrogen or (C 1 -C 8 ) -alkyl.
  • W is (W1); R 17 is halogen or (C 1 -C 6 haloalkyl; n 'is 0, 1, 2 or 3, wherein (R 17 V is preferably 2,4-Cl 2 ;
  • R 18 is a radical of the formula OR 24 ;
  • R 24 is hydrogen, (CrC 8) -alkyl, (C r C4) -haloalkyl, (Ci-C 4) hydroxyalkyl, (C 3 -
  • R 27 is hydrogen, (C r C 8 ) -alkyl, (C r C 4 ) -haloalkyl or (C 3 -C 7 ) -cycloalkyl, preferably hydrogen or (C 1 -C 4 ) -alkyl, and R x ' COOR 26 wherein R 26 is hydrogen, (Ci-C 8) -alkyl, (Ci-C 4) -haloalkyl, (C 1 -C 4) -
  • Hydroxyalkyl (C 3 -C 7 ) -cycloalkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl or Tn- (C 1 -C 2 ) -alkylsilyl, preferably hydrogen or ( C 4 ) alkyl.
  • herbicidal compositions comprising a safener of the formula (S-II) 1 in which the symbols and indices have the following meanings: W is (W 2 );
  • R 17 is halogen or (C 1 -C 6 haloalkyl; n 'is 0, 1, 2 or 3, wherein (R 17 V is preferably 2,4-Cl 2 ; R 18 is a radical of the formula OR 24 ; R 24 is hydrogen, (d-C ⁇ ) -alkyl, (dd) -haloalkyl, (dC 4 ) -hydroxyalkyl,
  • R 27 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 3 -C 7 ) -cycloalkyl or unsubstituted or substituted phenyl, preferably hydrogen, (d-)
  • Radicals from the group halogen, (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkyl, nitro, cyano or (Ci-C 4 ) -alkoxy is substituted.
  • R 17 is halogen or (C 1 -C 2 ) haloalkyl; n 'is 0, 1, 2 or 3, wherein (R 17 ) n ' is preferably 2,4-Cl 2 ; R 18 is a radical of the formula OR 24 ; R 24 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -hydroxyalkyl,
  • safeners of the formula (S-II) in which the symbols and indices have the following meanings: W is (W4); R 17 is halogen, nitro, (C 1 -C 4 ) -alkyl, (C 1 -C 2 ) -haloalkyl, preferably CF 3 , or
  • R 18 is a radical of the formula OR 24 ;
  • R 24 is hydrogen, (dd) -alkyl, carboxy (dC 4 ) -alkyl, (dC 4 ) -alkoxycarbonyl-
  • (C 1 -C 4 ) -alkyl preferably (C 1 -C 4 ) -alkoxy-CO-CH 2 -, (C 1 -C 4 ) -alkoxy-CO-C (CH 3 ) H-, HO-CO-CH 2 - or HO-CO- C (CH 3 ) H-, and
  • R 29 is hydrogen, (dC 4) -alkyl, (dC 4) -Ha! Oalkyl, (C 3 -C 7) -cycloalkyl or
  • Phenyl which is unsubstituted or substituted by one or more of the radicals Group halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, nitro, cyano and (C 1 -C 4 ) - alkoxy substituted.
  • N1, N2-diallyl-N2-dichloroacetylglycine amide (DKA-24 (IV-3), from HU 2143821),
  • Preferred safeners are compounds of the formula (S-V) or theirs
  • R 30 is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, furanyl or thienyl, where each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more substituents from the group consisting of halogen, (C 1 -C 4 ) -alkoxy, Halogen-
  • R 32 is halogen, halo (Ci-C 4) alkyl, halo (Ci-C 4) alkoxy, (dC 4) alkyl, (Ci-C 4) alkoxy, (dC 4) alkylsulfonyl, ( C r C 4 ) -alkoxycarbonyl or (CrC 4 ) -
  • Alkylcarbonyl preferably halogen, (Ci-C 4) -haloalkyl such as trifluoromethyl, (CrC 4) - alkoxy, halo (dC 4) alkoxy, (Ci-C 4) alkoxycarbonyl or (CrC 4) - alkylsulfonyl, R 33 hydrogen,
  • R 34 is halogen, (Ci-C 4) alkyl, halo (Ci-C 4) alkyl, halo (CrC 4) alkoxy,
  • R 35 is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 5 -C 6 ) -cycloalkenyl, phenyl or 3 to 6 hetero-cyclic heterocyclyl having up to three heteroatoms from the group consisting of nitrogen, oxygen and sulfur, where the six last-mentioned radicals are optionally substituted by one or more identical or different substituents from the group halogen, (C 1 -C 6 ) -alkoxy, (C 1 - Ce) -HaIOaIkOXy, (CrC 2 ) alkylsulfinyl, (CrC 2 ) alkylsulfonyl, (C 3 -C 6 ) -cycloalkyl, (Ci-C 4 ) alkoxycarbonyl, (dC ⁇ alkylcarbonyl and pheny
  • R 36 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, where the last three radicals mentioned are optionally substituted by one or more, identical or different substituents from the group halogen , hydroxy, (C 1 -C 4) - alkyl, (dC 4) -alkoxy and (dC 4) -alkylthio;
  • R 37 is halogen, (Ci-C 4) -haloalkyl, (Ci-C 4) -haloalkoxy, nitro, (Ci-C 4) alkyl, (Ci-C 4) - alkoxy, (Ci-C 4) -alkylsulfonyl , (C 1 -C 4 ) -alkoxycarbonyl or (C 1 -C 4 ) -alkylcarbonyl;
  • R 38 is hydrogen;
  • R 39 is halogen, nitro, (C 1 -C 4 ) -alkyl, (dC 4) -haloalkoxy, (C 3 -C 6) - cycloalkyl, phenyl, (Ci-C 4) -alkoxy, cyano, (dC ⁇ alkylthio, (C r C 4) - alkylsulfinyl, (Ci-C 4 ) Alkylsulfonyl, (C 1 -C 4 ) -alkoxycarbonyl or (C 1 -C 4 ) -alkylcarbonyl; n is 0, 1 or 2 and m is 1 or 2.
  • Preferred safeners of the formula (S-VII) are (S-3-1), (S-3-2), (S-3-3), (S-3-4) and (S-3-5).
  • Preferred safeners of the formula S-IX are compounds of the formulas S-IX-A1 to S-IX-A4,
  • herbicidal active compounds (A) as named in Table (I) and safeners (B) are those in which the safener (B) is selected from the group of safeners consisting of the compounds of the formulas S-II-1 ( Mefenpyr-diethyl), S-ll-9 (isoxadifen-ethyl), S-III-I (chloquintocet-mexyl), Sb-11 (fenclorim), Sb-14 (dymron), S-IX-A3 (4-cyclopropylaminocarbonyl N- (2-methoxybenzoyl) benzenesulfonamide N - ( ⁇ 4-
  • [(cyclopropylamino) carbonyl] phenyl ⁇ sulfonyl) -2-methoxybenzamides are compounds S-ll-1 and S-IX-A3). Isoxadifen-ethyl is particularly preferred for use in rice.
  • Particularly preferred for use in cereals are mefenpyr-diethyl, cloquintocetmexyl and 4-cyclopropylaminocarbonyl-N- (2-methoxybenzoyl) benzenesulfonamide N- ( ⁇ 4 - [(cyclopropylamino) carbonyl] phenyl ⁇ sulfonyl) -2-methoxybenzamide, in Corn, in particular, isoxadifen-ethyl and 4-cyclopropylaminocarbonyl-N- (2-methoxybenzoyl) benzenesulfonamide N - ( ⁇ 4 - [(cyclopropylamino) carbonyl] phenyl ⁇ sulfonyl) -2-methoxybenzamide.
  • Isoxadifen ethyl is preferred for use in sugar cane.
  • a mixture with other known active ingredients such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil conditioners is also possible.
  • the weight ratio of herbicide (mixture) to safener generally depends on the application rate of herbicide and the effectiveness of the particular safener and can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20.
  • the safeners can be formulated analogously to the compounds of the formula (I) or mixtures thereof with further herbicides / pesticides and provided and used as finished formulation or tank mixture with the herbicides.
  • Compounds of the formula (I) can vary within wide limits, e.g. between 0.001 and 10.0 kg / ha or more of active substance, but is preferably between 0.005 and 5 kg / ha.
  • the active compounds of the invention may e.g. used in the following plants:
  • the active compounds according to the invention are suitable for total weed control, depending on the concentration, e.g. on industrial and railway tracks and on paths and squares with and without tree cover.
  • the active compounds of the present invention may be used for weed control in permanent crops, e.g. Forestry, ornamental, fruit, wine, citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports lawns and grazing land and selective Weed control in one-year crops.
  • the compounds of the formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when applied to the soil and above-ground parts of plants. They also lend themselves, to some extent, to the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both preemergence and postemergence.
  • the residue is taken up in 100 ml of methylene chloride, washed twice with 5% hydrochloric acid and once with water.
  • the organic phase is filtered over sodium sulfate and filtered.
  • the filtrate is concentrated in a water-jet vacuum and the remaining residue is crystallized from isopropanol.
  • the resulting colorless solid is filtered off with suction, washed with diethyl ether and dried in air.
  • Table 2b Examples of the compounds of the formula (IIB)
  • Table 2c Examples of the compounds of the formula (HC)
  • Sulfonyl isocyanates are prepared by known methods from a corresponding sulfonamide of the formula (II), an alkyl isocyanate such as n-butyl isocyanate, phosgene and a catalytic amount of 1, 4-diaza [2.2.2] bicyclooctane (DABCO) in XyIoI or other inert Solvent prepared with a sufficiently high boiling point (> 135 0 C), cf. H. Ulrich and AAY Sayigh, Newer Methods of Preparative Organic Chemistry, Vol. VI, p. 223-241, Academic Press, New York and London, W. Foerst Ed. also WO 2003/033459.
  • an alkyl isocyanate such as n-butyl isocyanate
  • phosgene and a catalytic amount of 1, 4-diaza [2.2.2] bicyclooctane (DABCO) in XyIoI or other inert Solvent prepared with
  • Test compounds formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then treated as an aqueous suspension with a
  • the pots are placed in the greenhouse and kept under good growth conditions for the test plants.
  • the visual assessment of the damage to the test plants takes place after a test time of 3
  • Test plants of monocotyledonous or dicotyledonous crops are laid out in sandy loam soil in wood fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage.
  • the test compounds formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then sprayed onto the green parts of plants as an aqueous suspension with an application rate of 800 l / ha with the addition of 0.2% wetting agent.
  • WP wettable powders
  • EC emulsion concentrates
  • the compounds according to Preparation IA-1, IA-2, IA-3, IA-5, IA-6, IA-7, IA-8 and IA-9 exhibit, with partially good compatibility with crop plants, e.g. Corn and wheat, very strong against weeds.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne de nouvelles furyl-sulfonylamino(thio)carbonyl-triazoline-(thi)ones substituées, de formule générale (I) dans laquelle Q<SUP>1</SUP> désigne O (oxygène) ou S (soufre), Q<SUP>2</SUP> désigne O (oxygène) ou S (soufre), R<SUP>a</SUP> désigne un hydrogène, cyano, nitro, halogène ou un alkyle, alcoxy, alkylthio, alkylsulfinyle, alkylsulfonyle, alcényle, alcinyle, alcényloxy ou alcinyloxy, respectivement, éventuellement substitués, R<SUP>b</SUP> désigne un hydrogène, cyano, nitro, halogène ou un alkyle, alcoxy, alkylthio, alkylsulfinyle, alkylsulfonyle, alcényle, alcinyle, alcényloxy ou alcinyloxy, respectivement, éventuellement substitués, R<SUP>c</SUP> désigne CO-Y, R<SUP>6</SUP> désigne un hydrogène, hydroxy, amino, cyano, alkylidèneamino, ou un alkyle, alcényle, alcinyle, alcoxy, alkylamino, alkylcarbonylamino, alcényloxy, dialkylamino, cycloalkyle, cycloalkylamino, cycloalkylalkyle, aryle ou arylalkyle, respectivement, éventuellement substitués, R<SUP>7</SUP>désigne un hydrogène, hydroxy, mercapto, amino, cyano, halogène ou un alkyle, alcényle, alcinyle, alcoxy, alkylthio, alkylamino, alkylcarbonylamino, alcényloxy, alcinyloxy, alcénylthio, alkinylthio, alcénylamino, alcinylamino, dialkylamino, aziridino, pyrrolidino, pipéridino, morpholino, cycloalkyle, cycloacényle, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyle, cycloalkylalcoxy, cycloalkylalkylthio, cycloalkylalkylamino, aryle, arylalkyle, aryloxy, arylalcoxy, arylthio, arylalkylthio, arylamino ou arylalkylamino, respectivement, éventuellement substitués, ou R<SUP>7</SUP>et R<SUP>6</SUP> désignent tous deux un alcanediyle éventuellement ramifié, et Y désigne l'un des groupements OR<SUP>8</SUP> ou N(R<SUP>9</SUP>R<SUP>10</SUP>), dans lesquels R<SUP>8</SUP>désigne un alkyle, alcényle, alcinyle, cycloalkyle, cycloalkylalkyle, aryle, arylalkyle, hétérocyclyle ou hétérocyclylalkyle, respectivement, éventuellement substitués, R<SUP>9</SUP> désigne un hydrogène ou un alkyle, alcényle, alcinyle, cycloalkyle, cycloalkylalkyle, aryle, arylalkyle, hétérocyclyle ou hétérocyclylalkyle, respectivement, éventuellement substitués, et R<SUP>10</SUP> désigne un hydrogène ou un alkyle, alcényle, alcinyle, cycloalkyle, cycloalkylalkyle, aryle, arylalkyle, hétérocyclyle ou hétérocyclylalkyle, respectivement, éventuellement substitués, ainsi que des sels des composés de formules (I). L'invention concerne en outre des procédés de production desdits composés, ainsi que leur utilisation comme herbicides.
EP07765059A 2006-07-12 2007-07-05 Furyl-sulfonylamino(thio)carbonyl-triazoline(thi)ones substituées Withdrawn EP2046781A2 (fr)

Applications Claiming Priority (2)

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DE200610032164 DE102006032164A1 (de) 2006-07-12 2006-07-12 Substituierte Furyl-sulfonylamino(thio)carbonyl-triazolin(thi)one
PCT/EP2007/005935 WO2008006499A2 (fr) 2006-07-12 2007-07-05 Furyl-sulfonylamino(thio)carbonyl-triazoline(thi)ones substituées

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WO2013134562A1 (fr) 2012-03-09 2013-09-12 Inception 2, Inc. Composés de triazolone et leurs utilisations
CA2894281C (fr) 2012-12-20 2021-04-20 Inception 2, Inc. Composes de triazolone et leurs utilisations
PE20160880A1 (es) 2013-09-06 2016-09-22 Inception 2 Inc Compuestos de triazolona y usos de los mismos

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DE19540737A1 (de) * 1995-11-02 1997-05-07 Bayer Ag Substituierte Sulfonylamino(thio)carbonylverbindungen
DE10146591A1 (de) * 2001-09-21 2003-04-10 Bayer Cropscience Ag Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen

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CA2657598A1 (fr) 2008-01-17
BRPI0715451A2 (pt) 2013-02-26
WO2008006499A8 (fr) 2008-03-06
DE102006032164A1 (de) 2008-01-24

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