WO2011003775A2 - Cyanobutyrates substitués à effet herbicide - Google Patents

Cyanobutyrates substitués à effet herbicide Download PDF

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WO2011003775A2
WO2011003775A2 PCT/EP2010/059184 EP2010059184W WO2011003775A2 WO 2011003775 A2 WO2011003775 A2 WO 2011003775A2 EP 2010059184 W EP2010059184 W EP 2010059184W WO 2011003775 A2 WO2011003775 A2 WO 2011003775A2
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formula
alkyl
compounds
methyl
haloalkyl
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PCT/EP2010/059184
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German (de)
English (en)
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WO2011003775A3 (fr
Inventor
Dschun Song
Julia Major
Johannes Hutzler
Trevor William Newton
Andrea Vescovi
Robert Reinhard
Bernd Sievemich
Cyrill Zagar
Elmar Kibler
Ricarda Niggeweg
Toralf KÜHN
Thomas Ehrhardt
Klaus Kreuz
Klaus Grossmann
Anna Aleksandra Michrowska
Anja Simon
Richard Roger Evans
Eike Hupe
Matthias Witschel
William Karl Moberg
Liliana Parra Rapado
Tao QU
Frank Stelzer
Andree Van Der Kloet
Thomas Seitz
Klaus Reinhard
Matthias Bergtold
Susanne Kolle
Stefan Tresch
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Basf Se
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Publication of WO2011003775A2 publication Critical patent/WO2011003775A2/fr
Publication of WO2011003775A3 publication Critical patent/WO2011003775A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton

Definitions

  • the present invention relates to substituted cyanobutyrates of the formula I.
  • R is halogen, cyano, nitro, Ci -C4 -alkyl, Ci-C 4 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 -alkyl kinyl, CrC 4 -
  • R 1 is C 1 -C 6 -haloalkyl, benzyl, phenyl, where the aromatic groups may be unsubstituted or partially or completely substituted by groups R a and / or R b ,
  • R a is OH, C 1 -C 5 -alkyl, C 1 -C 4 - Haloalkyl, ZC 3 -C 6 -cycloalkyl, C 2 -C 8 -alkenyl, ZC 5 -C 6 -cyclo-alkenyl, C 2 -C 8 -alkynyl, Z-Ci-C 6 -alkoxy, Z-Ci- C 4 haloalkoxy, Z C 3 -C 8 alkenyloxy, Z-
  • R b is independently Z-CN, Z-OH, Z-NO 2, Z is halogen, Ci-C 8 alkyl, Ci-C 4 - haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 -Al kinyl, Z-C 1 -C 8 -alkoxy, Z-C 1 -C 8 -haloalkoxy, ZC 3 -cycloalkyl, O-ZC 3 -cycloalkyl,
  • ZC ( O) -R a , NR 1 R ", Z- (tri-Ci-C 4 -alkyl) silyl, Z-phenyl and S (O) x R bb , wherein R bb Ci-C 8 alkyl and Ci-C 6 haloalkyl means;
  • R b can also form, together with the group R b attached to the adjacent carbon atom, a five- or six-membered saturated, partially or completely unsaturated ring which, in addition to carbon, contains 1, 2 or 3 heteroatoms selected from O, N and S. can;
  • Z is a covalent bond or C 1 -C 6 -alkylene;
  • R 2 is halogen, cyano, nitro, C -C alkyl 4 -alkyl, Ci-C 4 alkoxy, S (O) x R bb, NR 1 R "Ci-C 4 haloalkyl,
  • n are independently 0, 1, 2, 3, 4 or 5;
  • groups R, R 1 and R 2 and their sub-substituents the carbon chains and / or the cyclic groups may be partially or completely substituted by groups R a and / or R b ,
  • R 1 is not unsubstituted benzyl when R n is 4-F and (R 2 ) m is 3-F;
  • the invention relates to processes and intermediates for the preparation of the compounds of formula I and their N-oxides, their agriculturally useful salts, agents containing them and their use as herbicides, i. for controlling harmful plants, and a method for controlling undesired plant growth, comprising allowing a herbicidally effective amount of at least one compound of formula I or an agriculturally useful salt thereof to act on plants, their seeds and / or their habitat.
  • EP-A 5 341, EP-A 266 725, EP-A 270 830, JP 04/297 454, JP 04/297 455 and JP 05/058 979 disclose herbicidal cyanobutyrates, their herbicidal action, in particular at low application rates, However, their compatibility with crops remains in need of improvement.
  • An object of the present invention is to provide compounds having herbicidal activity. In particular, active ingredients should be made available which have a high herbicidal action, in particular even at low application rates, and their compatibility with crop plants for commercial exploitation is sufficient.
  • the compounds according to the invention differ from those known from the abovementioned publications by the configuration of the group R 1 . They can be prepared analogously to the synthetic routes described in the cited documents by standard methods of organic chemistry, for example according to the following synthesis route: Phenylacetonitrile derivatives of the formula II can be reacted with cinnamate derivatives of the formula III in the sense of a Michael addition to give compounds of the formula I. In formulas II and III, the variables have the meaning given for formula I.
  • This reaction is usually carried out at temperatures of -100 0 C to 150 0 C, preferably -78 ° C to 50 0 C, in a solvent in the presence of a base and / or a catalyst [see. J. Chem. Soc. (1945), p. 438].
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone (MTBE), alcohols such as methanol, ethanol, n-propanol, isopropanol, n Butanol and tert-butanol, and dimethyl sulfox
  • Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal oxides, alkali metal and alkaline earth metal hydrides, alkali metal amides such as lithium bis (trimethylsilyl) amide, lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates and alkali metal hydrogencarbonates, organometallic compounds, especially alkali metal alkyls, alkylmagnesium halides and alkali metal and alkaline earth metal alcoholates such as sodium methoxide, sodium ethoxide, potassium ethanoate, potassium tert-butoxide and dimethoxy magnesium, in addition to organic bases, eg tertiary amines such as trimethylamine, triethylamine, tributylamine, di-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, luti
  • the bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.
  • Acid catalysts include inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid, Lewis acids such as boron trifluoride, aluminum trichloride, ferric chloride, tin IV chloride, titanium IV chloride, scandium III triflate and zinc chloride, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, toluenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid and trifluoroacetic acid.
  • Lewis acids such as boron trifluoride, aluminum trichloride, ferric chloride, tin IV chloride, titanium IV chloride, scandium III triflate and zinc chloride
  • organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, toluenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid
  • the acids are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.
  • the compounds of the formula I can preferably be obtained by transesterification of other cyanobutyrates of the formula IV in which R 'is a radical which is different from R 1 . This can be done by generally known methods, for example according to the following:
  • the transesterification can be carried out in the presence of molecular sieve in an alcohol R 1 -OH, optionally in an aprotic solvent.
  • This reaction is usually carried out at temperatures of 0 0 C to 180 ° C, preferably 20 0 C to 80 0 C in the presence of a Lewis article. Bransted acid [S] or an enzyme [cf. J. Org. Chem. 2002, 67, 431].
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and THF, nitriles such as acetonitrile and propionitrile, ketones such as dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably the alcohol R 1 -OH. It is also possible to use mixtures of the solvents mentioned.
  • the transesterification can be carried out by acidic or basic saponification of other cyanobutyric acid (a), followed by reaction with an alcohol R 1 -OH (b). These reactions are usually carried out at temperatures of 0 0 C to 120 0 C, preferably 20 0 C to 50 0 C in the presence of a base, or an acid and / or a catalyst [see. J. Am. Chem. Soc. 2007, 129 (43), 13321; J. Org. Chem. 1984, 49 (22), 4287.].
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butyl Butanol, and dimethyl sul
  • Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, alkali metal and alkaline earth metal hydrides, alkali metal amides, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate.
  • alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide
  • alkali metal and alkaline earth metal oxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide
  • alkali metal and alkaline earth metal oxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide
  • alkali metal and alkaline earth metal oxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide
  • organometallic compounds in particular alkali metal alkyls, alkylmagnesium halides and also alkali metal and alkaline earth metal alcoholates such as sodium methoxide, sodium ethanolate, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermore organic bases, eg tertiary amines, pyridine, substituted pyridines and bicyclic amines such as 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU). Particularly preferred is lithium hydroxide, potassium carbonate and DBU.
  • the bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.
  • acids and acidic catalysts are inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid,
  • Lewis acids such as boron trifluoride, aluminum trichloride, ferric chloride, tin (IV) chloride, titanium (IV) chloride and zinc (II) chloride, and also organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, toluenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, Citric acid and trifluoroacetic acid use.
  • organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, toluenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, Citric acid and trifluoroacetic acid use.
  • the acids are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.
  • the reaction mixtures are worked up in the usual way, e.g. by mixing with water, separation of the phases and optionally chromatographic purification of the crude products.
  • the intermediate and end products are z.T. in the form of colorless or pale brownish, viscous oils, which are freed or purified under reduced pressure and at moderately elevated temperature from volatile constituents. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.
  • halogenated substituents preferably carry one to five identical or different halogen atoms, in particular fluorine atoms or chlorine atoms.
  • halogen in each case represents fluorine, chlorine, bromine or iodine.
  • Alkyl and the alkyl moieties for example, in alkoxy, alkylamino, dialkylamino, N-alkylsulfonylamino, alkylaminosulfonylamino, dialkylaminosulfonylamino, N- (alkenyl) -N- (alkyl) -amino, N- (alkynyl) -N- (alkyl) -amino, N- (alkoxy) -N- (alkyl) -amino: saturated, straight-chain or branched hydrocarbon radicals having one or more C atoms, for example 1 to 2, 1 to 4, or 1 to 6 carbon atoms, for example C 1 -C 6 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbut
  • alkyl is a small alkyl group such as C 1 -C 4 -alkyl. In another embodiment of the invention, alkyl is greater alkyl groups such as Cs-C ⁇ -alkyl.
  • Haloalkyl also referred to as haloalkyl: an alkyl radical as mentioned above, the hydrogen atoms of which are partially or completely substituted by halogen atoms such as fluorine, chlorine, bromine and / or iodine, e.g.
  • Cycloalkyl and the cycloalkyl moieties for example, in cycloalkoxy or cycloalkylcarbonyl: monocyclic, saturated hydrocarbon groups having three or more C atoms, e.g. 3 to 6 carbon ring members such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Alkenyl and alkenyl moieties for example, in alkenylamino, alkenyloxy, N- (alkenyl) -N- (alkyl) -amino, N- (alkenyl) -N- (alkoxy) -amino: monounsaturated, straight-chain or branched hydrocarbon radicals having two or more carbon atoms. Atoms, z. 2 to 4, 2 to 6 or 3 to 6 carbon atoms and a double bond in any position, e.g. C 2 -C 6 alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl,
  • Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups having 3 to 6, preferably 5 to 6, carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexyl-1-yl, cyclohexen-3-yl, cyclohexen-4-yl ,
  • Alkynyl and alkynyl moieties for example in alkynyloxy, alkynylamino, N- (alkynyl) -N- (alkyl) -amino or N- (alkynyl) -N- (alkoxy) -amino: straight-chain or branched hydrocarbon groups having two or more carbon atoms , z. B. 2 to 4, 2 to 6, or 3 to 6 carbon atoms and a triple bond in any position, for.
  • C 2 -C 6 -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,
  • Alkoxy alkyl, as defined above, which is bonded via an oxygen atom: z.
  • 5- or 6-membered heterocycle a cyclic group having 5 or 6 ring atoms wherein 1, 2, 3 or 4 ring atoms are heteroatoms selected from O, S and N, the cyclic group being saturated, partially unsaturated or aromatic is. Examples of heterocyclic groups are.
  • the compounds of formula I contain two chiral centers and, depending on the substitution pattern, may contain one or more others.
  • the compounds according to the invention can therefore be present as pure enantiomers or diastereomers or as mixtures of enantiomers or diastereomers.
  • the invention relates to both the pure enantiomers or diastereomers and mixtures thereof.
  • the compounds of the formula I can also be present in the form of the N-oxides and / or their agriculturally useful salts, the type of salt generally not being important.
  • the salts of those cations or the acid addition salts of those acids come into consideration whose cations, or anions, do not adversely affect the herbicidal activity of the compounds I.
  • ions of the alkali metals preferably lithium, sodium or potassium, the alkaline earth metals, preferably calcium or magnesium, and the transition metals, preferably manganese, copper, zinc or iron are suitable as cations.
  • ammonium as the cation, where, if desired, one to four hydrogen atoms are represented by C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkoxy C 1 -C 4 -alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (2-hydroxyeth-1-oxy) eth-1-ylammonium, di (2-hydroxyeth-1 -yl) ammonium
  • the pyridine nitrogen atom of the formula I quaternized by alkylation or arylation is also suitable.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C1-C4 alkanoic acids, preferably formate, acetate, propionate, Butyrate or trifluoroacetate.
  • variables of the compounds of the formula I have the following meanings, these being considered both individually and in combination with one another in particular embodiments of the compounds of the formula I:
  • the subscript n stands for a value of 0 to 3, preferably for 0, 1 or 2, in particular for 1. In another embodiment, it stands for 0. If at least one group R is present, it is preferably in positions 3, 4 and / or 5, in particular 3 or 4. If the index n has the value 2, the groups R are preferably in positions 3, 5 or 3, 4th
  • Preferred embodiments of the group (s) R n concern halogen, in particular chlorine or fluorine, particularly preferably fluorine. Further embodiments of the group (s) R n concern cyano or nitro, in particular cyano. In further preferred embodiments, R n is halomethyl, such as CF 3 or CH F 2. In further preferred embodiments, R n is halomethoxy, such as OCF 3 or OCHF 2. In further preferred embodiments, R n is C 1 -C 4 -alkyl, preferably methyl. In further preferred embodiments, R n is C 2 -C 6 -alkynyl, preferably propargyl.
  • R n is C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy or S (O) x R aa , where R aa is preferably methyl and the index x is preferably 0 or 2.
  • a preferred embodiment of the group R 1 relates to C 1 -C 4 -haloalkyl, in particular C 2 -C 3 -haloalkyl.
  • the haloalkyl groups preferably contain 1 to 3 halogen atoms, which are selected in particular from chlorine and fluorine. Particularly preferred is haloethyl, such as 2,2-dihaloethyl, wherein the halogen atoms are selected from chlorine and fluorine.
  • halopropyl such as 3,3,3-tri-halopropyl or 2,2,3,3-tetra-halopropyl, in which the halogen atoms are selected from chlorine and fluorine.
  • R 1 include the following: CH 2 CH 2 F, CH 2 CHF 2 , CH 2 CF 3 , CH 2 CH 2 CF 3 , CH 2 CF 2 CHF 2 ,
  • R 1 Another preferred embodiment of the group R 1 relates to phenyl which is unsubstituted or partially or completely substituted. Suitable substituents are in particular halogen atoms, in particular fluorine, in question. Particularly preferred embodiments of these embodiments for R 1 include the following: 2-F-CeH 4 ,
  • a further preferred embodiment of the group R 1 relates to benzyl which is unsubstituted or partially or completely substituted at any position. Suitable substituents are in particular halogen atoms, in particular fluorine, or C 1 -C 4 -alkyl, in particular methyl, in question. Particularly preferred embodiments of these embodiments for R 1 include the following: CH 2 C 6 H 5 , CH (CH 3 ) C 6 H 5 , CH 2 (2-FC 6 H 5 ), CH (CH 3 ) (2-FC 6 H 5 ), CH 2 - (2-FC 6 H 4 ), CH 2 - (3-FC 6 H 4 ), CH 2 - (4-FC 6 H 4 ) and
  • the index m is preferably 2.
  • Advantageous embodiments of the group R 2 relate to halogen, cyano, nitro, Ci-C 4 alkyl, -C 4 - alkoxy, S (O) m R bb, Ci-C 4 haloalkyl, Ci-C4-haloalkoxy.
  • Preferred embodiments of the group R 2 include halogen, CN, NO 2 , CH 3 , CHF 2 , CF 3 , OCHF 2 , OCF 3 .
  • Particularly preferred embodiments of the group R 2 are selected from fluorine, chlorine, bromine and iodine.
  • R 2 is preferably halogen, such as chlorine or fluorine, in particular fluorine. Particular preference is given to the following embodiments of (R 2 ) m : 3-F; 3-Cl; 3-Br; 3-CF 3 and 3-OCHF 2 .
  • At least one group of R and R 2 is fluorine.
  • the compounds I and their agriculturally useful salts are suitable - both as mixtures of isomers and in the form of pure isomers - as herbicides. They are suitable as such or as appropriately formulated agent.
  • the herbicidal compositions containing the compound I, in particular the preferred embodiments thereof control plant growth on non-crop surfaces very well, especially at high application rates. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crops. This effect occurs especially at low application rates.
  • the compounds I, in particular the preferred embodiments thereof, or agents containing them can be used in a further number of crop plants for the removal of undesirable plants. For example, the following cultures may be considered:
  • crops also includes those that have been modified by breeding, mutagenesis or genetic engineering methods.
  • Genetically engineered plants are plants whose genetic material has been altered in a manner that does not occur under natural conditions by crossing, mutations or natural recombination (i.e., rearrangement of genetic information).
  • one or more genes are integrated into the genome of the plant in order to improve the properties of the plant.
  • crops thus also encompasses plants which, by breeding and genetic engineering measures, tolerate certain herbicide classes, such as
  • HPPD Hydroxyphenylpyruvate dioxygenase
  • ALS acetolactate synthase
  • EP-A 257 993, US 5,013,659 As sulfonylureas (EP-A 257 993, US 5,013,659) or imidazolium none (see, eg, US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218,
  • WO 03/13225, WO 03/14356, WO 04/16073), enolpyruvylshikimate-3-phosphate synthase (EPSPS) -inhibitors such. Glyphosate (see, for example, WO 92/00377), glutamine synthetase (GS) inhibitors such as. Glufosinate (see eg EP-A 242 236, EP-A 242 246) or oxynil herbicides (see eg US 5,559,024).
  • crops thus also includes plants that use genetic engineering measures one or more toxins, eg. As those from the bacterial strain Bacillus ssp., Produce.
  • Toxins produced by such genetically engineered plants include e.g. Insecticidal proteins of Bacillus spp., In particular B. thuringiensis such as the endotoxins CrylAb, CrylAc, CrylF, Cry1Fe2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs), e.g.
  • VIPs vegetative insecticidal proteins
  • VIP1, VIP2, VIP3, or VIP3A insecticidal proteins of nematode-colonizing bacteria, e.g. B. Photorhabdus spp. or Xenorhabdus spp .; Toxins from animal organisms, eg. B. Wepsen, spider or scorpion toxins; fungal toxins, e.g. B. from streptomycetes; herbal lectins, e.g. From pea or barley; agglutinins; Proteinase inhibitors, e.g. Trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; Ribosome Inactivating Proteins (RIPs), e.g. Ricin, corn RIP, abrin, luffin, saporin or bryodin; Steroid metabolizing
  • RIPs Ribosome Inactivating Proteins
  • Enzymes e.g. 3-hydroxysteroid oxidase, ecdysteroid IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitors or HMG-CoA reductase; ion channel blocker, e.g. B. inhibitors of sodium or calcium channels; Juvenile hormone esterase; Receptors for the diuretic hormone (helicokinin receptors); Stilbene synthase, bibenzyl synthase, chitinases and glucanases. These toxins can also be produced in the plants as proteoxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a novel combination of different protein domains (see, for example, WO 2002/015701). Further examples of such toxins or genetically modified plants which produce these toxins are described in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878,
  • the methods for producing these genetically modified plants are known in the art and z. As set forth in the publications mentioned above. Many of the aforementioned toxins confer on the plants that produce them a tolerance to pests of all taxonomic arthropod classes, in particular to beetles (Coeleropta), diptera (Diptera) and butterflies (Lepidoptera) and nematodes (Nematoda). Genetically engineered plants that produce one or more genes encoding insecticidal toxins, e.g. As described in the publications mentioned above and partly commercially available, such as. B.
  • YieldGard ® (corn cultivars producing the toxin CrylAb), YieldGard ® Plus (corn cultivars producing the toxins CrylAb and Cry3Bb1), StarLink ® (corn cultivars producing the toxin Cry9c), Herculex ® RW (corn cultivars toxins which Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin N-acetyltransferase [PAT] produce); NuCOTN ® 33B (cotton varieties that produce the toxin CrylAc), Bollgard ® I (cotton varieties that produce the toxin CrylAc), Bollgard ® II (cotton varieties that contain the toxins CrylAc and
  • Agrisure ® CB and Bt176 from Syngenta Seeds SAS, France corn varieties which produce the toxin CrylAb and the PAT enzyme
  • MIR604 from Syngenta Seeds SAS, France
  • MON 863 from Monsanto Europe SA, Belgium
  • IPC 531 from Monsanto Europe SA, Belgium
  • cottons producing a modified version of the toxin CrylAc 1507 from Pioneer Overseas Corporation, Belgium (maize varieties producing the toxin Cryl F and the PAT enzyme).
  • crops thus also includes plants that produce by genetic engineering measures one or more proteins that cause increased resistance or resistance to bacterial, viral or fungal pathogens, such as.
  • PR proteins pathogenesis-related proteins
  • resistance proteins eg, potato varieties that produce two resistance genes against Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum
  • T4 lysozyme z. Potato varieties resistant to bacteria such as Erwinia amylvora by the production of this protein).
  • crops thus also includes plants whose productivity has been improved by means of genetic engineering methods by z.
  • yield eg biomass, grain yield, starch, oil or protein content
  • tolerance to drought salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens may be increased.
  • crops also includes plants whose ingredients have been modified in particular to improve the human or animal diet using genetic engineering methods by z.
  • oil plants can produce health-promoting long-chain omega-3 fatty acids or monounsaturated omega-9 fatty acids (eg Nexera ® oilseed rape).
  • crops also includes plants that have been modified for the improved production of raw materials by means of genetic engineering methods by z.
  • the amylopectin content of potatoes (Amflora ® potato) was increased.
  • the compounds of the formula I are also suitable for the defoliation and / or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, come into consideration.
  • compositions for the desiccation and / or defoliation of plants, processes for the preparation of these agents and methods for the desiccation and / or defoliation of plants with the compounds of formula I have been found.
  • the compounds of formula I are particularly suitable for dehydration of the aerial parts of crop plants such as potato, oilseed rape, sunflower and soybean but also cereals. This enables a completely mechanical harvesting of these important crops.
  • harvest facilitation which is made possible by the time-concentrated dropping or reducing the adhesion of the tree to citrus fruit, olives or other types and varieties of pome, stone and peel fruit.
  • the same mechanism i.e. promoting the formation of release webs between fruit or leaf and shoot part of the plants, is also essential for a well controllable defoliation of crops, especially cotton.
  • shortening the time interval in which each cotton plant ripens leads to increased fiber quality after harvest.
  • the compounds I or the herbicidal compositions containing them for example in the form of directly sprayable aqueous solutions, powders, suspensions, even high-percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules by spraying , Misting, dusting, scattering, pouring or treatment of the seed or mixing with the seed.
  • the forms of application depend on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • the herbicidal compositions contain a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries customary for the formulation of pesticides.
  • auxiliaries are preferred auxiliaries, solid carriers, surface-active substances (such as dispersants, protective colloids, emulsifiers, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, if necessary, dyes and for seed formulations adhesives.
  • surface-active substances such as dispersants, protective colloids, emulsifiers, wetting agents and adhesives
  • organic and inorganic thickeners such as bactericides, antifreeze agents, defoamers, if necessary, dyes and for seed formulations adhesives.
  • thickeners ie, compounds which impart modified flowability to the formulation, ie, high-level at low viscosity and low viscosity in the agitated state
  • polysaccharides such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum ® (RT Vanderbilt) and organic and inorganic layer minerals such as Attaclay® (Engelhardt).
  • antifoams are silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
  • Bactericides may be added to stabilize the aqueous herbicidal formulation.
  • bactericides are bactericides based on diclorophene and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS der Fa. Thor Chemie)
  • antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.
  • colorants are both water-insoluble pigments and water-soluble dyes. Examples which may be mentioned under the names rhodamine B, Cl. Pigment Red 112 and Cl. Solvent Red 1 known dyes, and pigment blue 15: 4, pigment blue 15: 3, pigment blue 15: 2, pigment blue 15: 1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 1 12, pigment red 48: 1, pigment red 48: 1, pigment red 57: 1, pigment red 53: 1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • adhesives examples include polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • Suitable inert additives are, for example:
  • Mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, eg. As amines such as N-methylpyrrolidone or water.
  • amines such as N-methylpyrrolidone or water.
  • Solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour
  • alkali alkaline earth
  • ammonium salts of aromatic sulfonic acids eg lignosulfonic acids (eg Borrespers types, Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types , Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE)
  • fatty acids alkyl and alkylaryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octa- decanols and also of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of na
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules e.g. Coating, impregnation and homogeneous granules can be prepared by binding the active compounds to solid carriers.
  • Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • emulsions, pastes or oil dispersions the compounds of the formula I or Ia, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers.
  • concentrates consisting of active substance, wetting, adhesion, dispersing or emulsifying agent and possibly solvent or oil, which are suitable for dilution with water.
  • the concentrations of the compounds of the formula I in the ready-to-use formulations can be varied within wide limits.
  • the formulations generally contain from 0.001 to 98% by weight, preferably from 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • the compounds I according to the invention can be formulated, for example, as follows:
  • active compound 15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (for example alkylaromatics) with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion.
  • the formulation has 15% by weight active ingredient content.
  • active compound 25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (for example alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • organic solvent for example alkylaromatics
  • calcium dodecylbenzenesulfonate and castor oil ethoxylate in each case 5 parts by weight.
  • This mixture is added to water by means of an emulsifying machine (e.g., Ultraturax) in 30 parts by weight and made into a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • active compound 20 parts by weight of active compound are comminuted with the addition of 10 parts by weight dispersing and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • active compound 50 parts by weight are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and prepared by means of industrial equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the formulation has an active ingredient content of 50% by weight.
  • active compound 75 parts by weight of active compound are ground with the addition of 25 parts by weight of dispersing and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • 0.5 parts by weight of active compound are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or the fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.
  • the application of the compounds I or the herbicidal compositions containing them can take place in the pre-emergence, post-emergence or together with the seed of a crop. It is also possible to apply the herbicidal compositions or active ingredients characterized in that with the herbicidal agents or active ingredients pretreated seed of a crop plant is applied. If the active ingredients are less compatible with certain crops, then application techniques may be employed whereby the herbicidal agents are sprayed by the sprayers so as not to hit the leaves of the sensitive crop if possible, while the active ingredients affect the leaves underneath growing undesirable plants or the uncovered floor surface (post-directed, lay-by).
  • the application of the compounds of the formula I or of the herbicidal compositions can be carried out by treating seed.
  • the treatment of seed comprises essentially all techniques familiar to the skilled worker (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of the formula according to the invention I or funds produced therefrom.
  • the herbicidal agents can be diluted or applied undiluted.
  • seed includes seeds of all kinds, e.g. Grains, seeds, fruits, tubers, cuttings and similar forms.
  • seed preferably describes grains and seeds here.
  • Seeds of the abovementioned crops but also the seeds of transgenic or obtained by conventional breeding methods plants can be used as seeds.
  • the application rates of active ingredient are from 0.001 to 3.0, preferably from 0.01 to 1.0, kg / ha of active substance (see above).
  • the compounds I are usually used in amounts of 0.001 to 10 kg per 100 kg of seed.
  • Safeners are chemical compounds that prevent or reduce damage to crops without significantly affecting the herbicidal activity of the compounds of formula I on undesirable plants. You can probably before sowing (for example in seed treatments, cuttings or seedlings) as well as in the pre or postemergence of the crop can be used.
  • the safeners and the compounds of formula I can be used simultaneously or sequentially.
  • Suitable safeners are, for example, (quinoline- ⁇ -oxy) acetic acids, 1-phenyl-5-haloalkyl-1H-1, 2,4-triazole-3-carboxylic acids, 1-phenyl-4,5-dihydro-5 alkyl-1H-pyrazole-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N- [ [4- (aminocarbonyl) phenyl] sulfonyl] -2-benzoic acid amides, 1,8-naphthalic anhydride, 2-halo-4- (haloalkyl) -5-thiazolecarboxylic acids, phosphorothiolates and N-alkyl-O-phenylcarba
  • the compounds of formula I can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups or with safeners and applied together.
  • herbicides which can be used in combination with the pyridine compounds of the formula I according to the present invention are:
  • Bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium; b8) from the group of DHP synthase inhibitors: asulam;
  • Y is phenyl or 5- or 6-membered heteroaryl as defined above, which may be substituted by one to three groups R aa ; R 21 , R 22 , R 23 , R 24 are H, halogen, or C 1 -C 4 -alkyl; X is O or NH; n 0 or 1.
  • R 25 is halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;
  • R 26 is C 1 -C 4 -alkyl;
  • R 27 is halogen, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy;
  • R 28 is H, halogen, Ci-C 4 - alkyl, Ci-C 4 haloalkyl or Ci-C4-haloalkoxy;
  • m is 0, 1, 2 or 3;
  • Particularly preferred compounds of the formula 2 are:
  • 2,4-D and its salts and esters 2,4-DB and its salts and esters, aminopyralid and its salts, such as aminopyralid tris (2-hydroxypropyl) ammonium and its esters,
  • auxin transport inhibitors diflufenzopyr, diflufenzopyrsodium, naptalam and naptalam sodium;
  • MSMA oleic acid, oxaziclomefon, pelargonic acid, pyributicarb, quinoclamin, triaziflam, tridiphan and 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol (B-10; CAS 499223-49-3 ) and its salts and esters.
  • Examples of preferred safeners C are Benoxacor, Cloquintocet, Cyometrinil, Cyprusulfamide, Dichlormid, Dicyclonon, Dietholate, Fenchlorazole, Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen, Mefenpyr, Mephenate, Naphthalic Anhydride, Oxabetrinile, 4- (Dichloroacetyl ) -1-oxa-4-azaspiro [4.5] decane (B-1 1, MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (B -12; R-29148, CAS 52836-31-4).
  • the active compounds of groups b1) to b15) and the safeners C are known herbicides and safeners, see, for example, US Pat. B. The Compendium of Pesticide Common Names
  • herbicidal active compounds are known from WO 96/26202, WO 97/411 16, WO 97/41 117, WO 97/411 18, WO 01 / 83459 and WO
  • the compounds I and the compositions according to the invention may also have a plant-strengthening effect. They are therefore suitable for mobilizing plant-own defenses against infestation by undesirable microorganisms, such as harmful fungi, but also viruses and bacteria.
  • plant-strengthening (resistance-inducing) substances are to be understood as meaning substances which are capable of stimulating the defense system of treated plants in such a way that they develop extensive resistance to these microorganisms during subsequent inoculation with undesired microorganisms.
  • the compounds I can be used to protect plants against attack by undesired microorganisms within a certain period of time after the treatment.
  • the period within which protection is provided generally extends from 1 to 28 days, preferably 1 to 14 days after treatment of the plants with the compounds I or after treatment of the seed, up to 9 months after sowing.
  • the compounds I and the compositions according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
  • HPLC-MS High Performance Liquid Chromatography combined with mass spectrometry
  • Step 1 3- (3-Chlorophenyl) -4-cyano-4- (4-fluorophenyl) butyric acid methyl ester
  • Step 2 3- (3-Chlorophenyl) -4-cyano-4- (4-fluorophenyl) -butyric acid
  • Step 3 3- (3-Chlorophenyl) -4-cyano-4- (4-fluorophenyl) -butyric acid 2,2-difluoroethyl ester
  • the culture vessels used were plastic pots with loamy sand with about 3.0% humus as substrate.
  • the seeds of the test plants were sown separately by species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing by means of finely distributing nozzles.
  • the jars were lightly rained to promote germination and growth and then covered with clear plastic hoods until the plants had grown. This cover causes a uniform germination of the test plants, if it was not affected by the active ingredients.
  • test plants were grown depending on the growth form only to a height of from 3 to 15 cm and then treated with the suspended or emulsified in water agents.
  • the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the plants were kept species-specific at temperatures of 10 - 25 ° C and 20 - 35 ° C, respectively.
  • the trial period lasted for 2 to 4 weeks. During this time, the plants were cared for, and their response to each treatment was evaluated.
  • the rating was based on a scale of 0 to 100. 100 means no emergence of the plants or complete destruction of at least the above-ground parts and 0 no damage or normal growth course. Good herbicidal activity is at least 70% and very good herbicidal activity is at least 85%.
  • the plants used in the greenhouse experiments were composed of the following species:
  • the active ingredient 1-109 showed at a rate of 0.125 kg / ha postemergence against AVEFA a good and the active ingredients I-37, I-68, and I-97 a very good herbicidal activity.
  • the active compounds 1-1 11, 1-121, and 1-124 showed at 0.25 kg / ha post-emergence against POLCO a good and the active ingredients I-46, I-70, I-76, 1-103 , 1-110, 1-116, 1-117, 1-1 18, 1-1 19, 1-120, 1-122, 1-123, 1-125, 1-126, 1-127, I-206 , I-207, I-208, 1-210, 1-21 1, I-214, 1-218, 1-219, I-220, 1-221, and I-222 a very good herbicidal activity.
  • the active ingredients I-68, I-94, I-95, I-96, 1-107, and 1-108 showed at a rate of 0.125 kg / ha postemergence against SETVI a very good herbicidal activity.
  • the active compounds 1-104, or 1-113 showed a good at 0.25 kg / ha post-emergence against SETVI and the active ingredients I-33, I-39, I-50, I-54, I-65, I-67, 1-103, 1-1 10, 1-1 14, I-207, I-208, 1-210, 1-211, 1-216, 1-218, 1-219, I-220, or I-222 a very good herbicidal activity.

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Abstract

L'invention concerne des cyanobutyrates substitués de formule (I) dans laquelle les variables sont définies conformément à la description. L'invention concerne également des procédés et des produits intermédiaires pour la production des composés de formule (I), de leurs N-oxydes et de leurs sels à usage agricole, ainsi que des produits les contenant et leur utilisation comme herbicides. L'invention concerne en outre des procédés pour lutter contre la croissance indésirable de végétaux.
PCT/EP2010/059184 2009-07-09 2010-06-29 Cyanobutyrates substitués à effet herbicide WO2011003775A2 (fr)

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EP2474226A1 (fr) * 2011-01-07 2012-07-11 Basf Se Composition active herbicide comportant des cyanobutyrates
WO2012126765A1 (fr) 2011-03-18 2012-09-27 Bayer Cropscience Ag (3r,4r)-4-cyan-3,4-diphénylbutanoates substitués, procédé de préparation desdits composés et leur utilisation en tant qu'herbicides et régulateurs de la croissance des plantes
WO2012126764A1 (fr) 2011-03-18 2012-09-27 Bayer Cropscience Ag 4-cyan-3-(2,6-difluorophényl)-4-phénylbutanoates substitués, procédé de préparation desdits composés et leur utilisation en tant qu'herbicides et régulateurs de la croissance des plantes
WO2013010882A2 (fr) 2011-07-15 2013-01-24 Bayer Intellectual Property Gmbh Dérivés de 2,3-diphényl-valéronitrile, leurs procédés de préparation et leur utilisation comme herbicides et régulateurs de croissance de plantes
WO2013064462A1 (fr) 2011-10-31 2013-05-10 Bayer Intellectual Property Gmbh 4-cyan-3-phényl-4-(pyridin-3-yl)butanoates substitués, procédé de production desdits composés, et utilisation desdits composés comme herbicides et régulateurs de la croissance des plantes
WO2013092500A1 (fr) 2011-12-19 2013-06-27 Bayer Intellectual Property Gmbh 4-cyan-3-phényl-4-(pyridine-3-yl)butanoates substitués, procédé de production desdits composés et utilisation desdits composés comme herbicides et régulateurs de la croissance des plantes
WO2014195253A1 (fr) 2013-06-07 2014-12-11 Bayer Cropscience Ag Dérivés 5-hydroxy-2,3-diphénylpentanonitrile substitués, procédés pour leur préparation et leur utilisation comme herbicides et/ou régulateurs de croissance des végétaux
WO2016001204A1 (fr) 2014-07-04 2016-01-07 Bayer Cropscience Ag Dérivés 5-hydroxy-2-hétéroaryl-3-phénylpentanonitrile substitués, leur procédé de fabrication et leur utilisation comme herbicides et/ou régulateurs de croissance végétale
US9661848B2 (en) 2012-12-21 2017-05-30 Bayer Cropscience Ag Substituted 4-cyan-3-(pyridyl)-4-phenylbutanoates, method for the production thereof and uses as herbicides and plant growth regulators
US10172350B2 (en) 2014-10-08 2019-01-08 Bayer Cropscience Aktiengesellschaft Substituted 5-hydroxy-2-phenyl-3-heteroaryl pentanenitrile derivatives, method for the production thereof and use thereof as herbicides and/or plant growth regulators

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