EP2369929A2 - Association d'herbicide(s) et de phytoprotecteur(s) - Google Patents

Association d'herbicide(s) et de phytoprotecteur(s)

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Publication number
EP2369929A2
EP2369929A2 EP09760111A EP09760111A EP2369929A2 EP 2369929 A2 EP2369929 A2 EP 2369929A2 EP 09760111 A EP09760111 A EP 09760111A EP 09760111 A EP09760111 A EP 09760111A EP 2369929 A2 EP2369929 A2 EP 2369929A2
Authority
EP
European Patent Office
Prior art keywords
chloro
compound
amino
pyridine
carboxylic acid
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Withdrawn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
EP09760111A
Other languages
German (de)
English (en)
Inventor
Christopher Hugh Rosinger
Erwin Hacker
Hartmut Ahrens
Hansjörg Dietrich
Frank Ziemer
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 Intellectual Property GmbH
Original Assignee
Bayer CropScience AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP09760111A priority Critical patent/EP2369929A2/fr
Priority to EP15167337.3A priority patent/EP2939541A1/fr
Priority to EP15167336.5A priority patent/EP2939540A1/fr
Publication of EP2369929A2 publication Critical patent/EP2369929A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • the present invention relates to agrochemically active herbicide-safener combinations, to processes for their preparation and to their use for controlling harmful plants.
  • WO 2003/011853, WO 2006/062979 and WO 2007/082098 describe pyridine derivatives which combat a broad spectrum of weeds.
  • WO 2009/029518 a post-published prior art, discloses mixtures of auxin herbicides with other herbicidal active ingredients and, in some cases, safeners. An increase in the selectivity or crop tolerance by the use of safener is not demonstrated, but only synergistic effects of the various herbicidal active ingredients.
  • WO 1999/16744 discloses safeners from the class of
  • WO 2001/035740 discloses mixtures of pyridine herbicides such as propoxycarbazone with other active ingredients. However, the present pyridine herbicides are structurally different from the class of substances disclosed therein.
  • the already disclosed active ingredients or combinations of active ingredients with auxin herbicides are sometimes not fully compatible with some important crops such as various cereals, corn or rice. Therefore, they can not be used in some crops to ensure the desired broad herbicidal activity against harmful plants.
  • the object of the present invention is therefore to find herbicidal agents in which the selectivity of the abovementioned herbicides is increased in relation to important crop plants. This object is surprisingly achieved by the herbicide-safener combination according to the invention.
  • X is hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, aryloxy, nitro, C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, thiocyano or cyano;
  • Y is an aryl group selected from a group consisting of phenyl, indanyl and naphthyl, or a heteroaryl group selected from the group of 5- and 6-membered heteroaromatic rings containing one or more heteroatoms, wherein the heteroaromatic rings optional with another aromatic
  • the aryl group or the heteroaryl group may be unsubstituted or substituted with one or more substituents selected from a group consisting of halogen, hydroxy, nitro, cyano, aryloxy, formyl, Ci-C 6 alkyl, cyclopropyl, C 2 -C 6 Alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, halogenated
  • Ci-C ⁇ alkyl, C 1 -C 4 -Alkoxy-substituiert.es CIC rAlkyl, halogenated CiC 6 alkoxy, CiC 4 alkoxy-substituted CiC 4 alkoxy, C 1 -C 6 - ACyI, fluorinated acetyl, fluorinated propionyl, the two being can last-mentioned groups each contain more fluorine atoms in the alkyl radical, d-Ce-alkylthio, Ci-C 6 alkylsulfinyl, C 1 -C 6 - alkylsulfonyl, halogenated Ci-C 6 alkylthio, aryl, amino, C 1 -C 4 - monoalkylamino , C 2 -C 8 dialkylamino, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylcarbonylamino, (C O
  • Z is halogen, C 6 alkyl, C 1 -C 6 -alkoxy, C r C 6 alkylthio, aryloxy, nitro, -C 6 haloalkyl, C 1 -C 6 -HaIOaIkOXy, thiocyano or cyano;
  • R 1 and R 2 are independently hydrogen, C- ⁇ -C 6 alkyl, C 3 -C 6 - alkenyl, C 3 -C 6 alkynyl, aryl, heteroaryl, hydroxy, Ci-C 6 alkoxy,
  • Amino, C 1 -C 6 -acyl, CRCE alkoxycarbonyl, C 1 -C 6 - alkylaminocarbonyl, dC 6 alkylsulfonyl, dC 6 trialkylsilyl or CrC 6 are -Dialkylphosphonyl; or
  • R 1 and R 2 together with N represent a five- or six-membered saturated or unsaturated ring which may optionally contain additional O, S or N heteroatoms;
  • R 3 and R 4 are independently hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, aryl or heteroaryl; or
  • compositions which contain the following combinations of further herbicidally active substances and safeners:
  • the present invention furthermore relates to the use of the safeners for increasing the selectivity and / or crop plant compatibility of the herbicides of the formula (I).
  • the herbicide-safener combinations according to the invention may contain additional other components, for example crop protection agents of another type and / or additives customary in plant protection and / or formulation auxiliaries, or be used together with them.
  • the herbicides (A) and the safeners (B) can be applied in a known manner, for example jointly (for example as a co-formulation or as a tank mixture) or also with a time offset (splitting), for example on the plants, plant parts, plant seeds or Surface on which the plants grow. It is possible, for example, the application of the individual active ingredients or herbicide-safener combination in several portions (sequence application), z. After pre-emergence applications, followed by post-emergence applications or early post-emergence applications, followed by mid-late post-emergence applications. Preference is given to the common or timely use of the active ingredients of the respective combination. It is also possible to use the individual active substances or the herbicide-safener combination for seed treatment.
  • the abovementioned formula (I) comprises all stereoisomers and mixtures thereof, in particular also racemic mixtures, and - as far as enantiomers are possible - both enantiomers and in particular the respective biologically active enantiomer.
  • preferred herbicides (A) are compounds of the general formula (I) and salts thereof, wherein the radical
  • X is hydrogen or fluorine
  • preferred herbicides (A) are compounds of the formula (I) and salts thereof, wherein the radical
  • Y is a phenyl group or a pyridinyl, benzofuranyl, benzothienyl, thienyl or thiazolyl group, wherein the phenyl group or the heteroaryl group may be substituted with one or more
  • Substituents selected from the group consisting of halogen, Ci-C 2 - alkyl, CrC 2 -Akoxy, C 1 -C 2 -haloalkyl and Ci-C 2 -haloalkoxy.
  • herbicides (A) in this second embodiment are compounds of the formula (I) and their salts, in which the radical
  • Y represents a phenyl group or a pyridinyl, benzofuranyl, benzothienyl, thienyl or thiazolyl group, wherein the phenyl group or the heteroaryl group is substituted with one or more substituents selected from the group consisting of halogen , C 1 -C 2 -alkyl, C 1 -C 2 -
  • herbicide (A) even more preferred in this second embodiment are compounds of formula (I) and their salts, wherein the radical
  • Y represents a tri- or tetra-substituted phenyl group, where the phenyl group is substituted by substituents independently of one another selected from the group consisting of halogen, C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy, C 2 haloalkyl and C 1 -C 2 haloalkoxy.
  • preferred herbicides (A) are compounds of the formula (I) and salts thereof, wherein the radical
  • herbicides (A) in this third embodiment are compounds of the formula (I) and salts thereof, in which the radical
  • herbicide (A) preferred are compounds of the formula (I) and salts thereof, wherein the radical
  • R 1 and R 2 are hydrogen or C 1 -C 6 -alkyl.
  • the amino group at the 4-position can be unsubstituted or substituted with one or more Ci-C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, aryl, heteroaryl, hydroxy, C -C 6 alkoxy or amino substituents.
  • the amino group may be further derivatized as an amide, a carbamate, a urea, a sulfonamide, a silylamine, a phosphoramidate, an imine or a hydrazone. These derivatives can be cleaved to the amine. Preference is given to an unsubstituted or substituted by one or two alkyl substituents amino group.
  • carboxylic acids of general formula (I) are the compounds that actually kill or control the undesired vegetation, and these are usually preferred.
  • Analogs of these compounds in which the acidic group of picolinic acid has been derivatized to form a related substituent which can be converted into an acid in the plants or in the environment have substantially the same herbicidal activity and are within the scope of the invention.
  • a "herbicidally active derivative” is any salt, ester, acylhydrazide, imidate, thioimidate, amidine, amide, orthoester, acyl cyanide, acyl halide, thioester, thionester, dithiol ester, nitrile, or any other acid derivative known to those skilled in the art which (a ) the herbicidal action of the active ingredient, namely 6-aryl- or heteroaryl-4-aminopicolinic acid, is not substantially impaired, and (b) hydrolyzed, oxidized or metabolized in plants or in the soil to the picolinic acid of general formula (I) which may be in the dissociated or undissociated form, depending on the pH.
  • the preferred herbicidally active derivatives of the carboxylic acid are agriculturally acceptable salts, esters and amides.
  • a "herbicidally active derivative" with respect to the amine functionality at the 4-position is any salt, silylamine, phosphorylamine, phosphinimine, phosphoramidate, sulfonamide, sulfilimine, sulfoximine, aminal, hemiaminal, amide, thioamide, carbamate, thiocarbamate, amidine , Urea, imine, nitro, nitroso, azide, or any other nitrogen-containing derivative known to those skilled in the art which (a) does not substantially affect the herbicidal activity of the active ingredient, namely 6-aryl or heteroaryl-4-aminopicolinic acid; (b) is or can be hydrolyzed in plants or in soil to a free amine of formula general formula (I).
  • N-oxides which may also be cleaved to the starting pyridine of formula
  • Suitable salts include those derived from alkali or alkaline earth metals and those derived from ammonia and amines.
  • Preferred cations include sodium, potassium, magnesium, and ammonium cations of the formula:
  • R 5, R 6 and R 7 are each independently hydrogen or Ci-Ci 2 -alkyl, C 3 -C 2 -alkenyl or C 3 -C 12 alkynyl, each optionally substituted with one or more hydroxy, C 1 -C 4 -AIkOXy-, Ci-C 4 alkylthio or substituted phenyl groups, with the proviso that R 5, R 6 and R 7 are sterically compatible.
  • any two may be selected from R 5, R 6 and R 7 together represent an aliphatic difunctional moiety containing 1 to 12 carbon atoms and up to two oxygen 'or sulfur atoms.
  • Salts of the compounds of the general formula (I) can be obtained by treating the compounds of the general formula (I) with a metal hydroxide, for example sodium hydroxide, or an amine, for example ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisallylamine, 2-butoxyethylamine, Morpholine, cyclododecylamine, or benzylamine are produced.
  • a metal hydroxide for example sodium hydroxide
  • an amine for example ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisallylamine, 2-butoxyethylamine, Morpholine, cyclododecylamine, or benzylamine are produced.
  • the amine salts are often the preferred forms of the compounds of general formula (I) because they are water-soluble and are suitable for the preparation of the desired water-based herbicidal compositions.
  • Suitable esters include those derived from C 3 -C 2 alkenyl or C 3 -C 12 - alkynyl alcohols, such as methanol, iso-propanol, butanol, 2-ethylhexanol, butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol or cyclohexanol, are derived.
  • Esters can be prepared by coupling the picolinic acid to the alcohol using any number of suitable activating agents, such as those used in the peptide couplings, such as dicyclohexylcarbodiimide (DCC) or carbonyldiimidazole (CDI), by reacting the corresponding acid chloride of a picolinic acid of the general formula ( I) with a suitable alcohol or by reacting the corresponding picolinic acid of general formula (I) with a suitable alcohol in the presence of an acid catalyst become.
  • suitable activating agents such as those used in the peptide couplings, such as dicyclohexylcarbodiimide (DCC) or carbonyldiimidazole (CDI)
  • Suitable amides include those derived from ammonia or Ci-Ci 2 -alkyl, C 3 -C 2 -alkenyl or C 3 -C 2 alkynyl mono- or di-substituted amines, such as, but not limited to dimethylamine, diethanolamine, 2-methylthiopropylamine, bisallylamine, 2-butoxyethylamine, cyclododecylamine, benzylamine or cyclic or aromatic amines with or without additional heteroatoms such as, but not limited to, aziridine, azetidine, pyrrolidine, pyrrole, imidazole, tetrazole or morpholine.
  • Amides can be prepared by reacting the corresponding picolinic acid chloride, mixed anhydride, or carboxylic acid ester of general formula (I) with ammonia or a suitable amine.
  • the compounds of the general formula (I) may furthermore be salts by addition of a suitable inorganic or organic acid, such as, for example, HCl, HBr, H 2 SO 4 or HNO 3 , but also oxalic acid or sulfonic acids to a basic group, for example amino or alkylamino form.
  • a suitable substituents which are present in deprotonated form such as, for example, sulfonic acids or carboxylic acids, can form internal salts with groups which can themselves be protonated, such as amino groups.
  • Salts can also be formed by replacing the hydrogen with a suitable cation for agriculture with suitable substituents, such as, for example, sulfonic acids or carboxylic acids.
  • Metal salts in particular alkali metal salts or alkaline earth metal salts, especially sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts with cations of the formula [NRR'R "R '"] + > wherein R to R 1 "are each independently each represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • the compounds of the general formula (I) may also comprise N-oxides.
  • Corresponding pyridine-N-oxides are accessible via oxidation of the corresponding pyridines. Suitable oxidation methods are, for example, in Houben-Weyl, Methods of Organic Chemistry, Extension and follow-up volumes to the 4th edition, Volume E 7b, p 565 f. described. Unless defined otherwise in detail, the following definitions generally apply to the radicals of the formula (I).
  • radicals alkyl, alkoxyalkyl, hydroxyalkyl and alkoxyalkoxyalkyl can each be straight-chain or branched.
  • alkyl is understood to mean, in particular, the radicals methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, or the various isomers of pentyl or hexyl.
  • alkoxyalkyl is understood to mean alkyl having an alkoxy substituent.
  • examples of the radical “alkoxyalkyl” include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 21 CH 3 CH 2 OCH 2 CH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 CH 2 or CH 3 CH 2 CH 2 CH 2 OCH 2 CHMe.
  • alkoxyalkoxy is understood as meaning alkoxy provided with an alkoxy substituent.
  • Alkoxyalkoxyalkyl means a radical in which an alkoxyalkoxy substituent is attached to an alkyl radical.
  • alkoxyalkoxyalkyl include CH 3 OCH 2 OCH 2 , CH 3 OCH 2 OCH 2 CH 2 , CH 3 CH 2 OCH 3 OCH 2 and CH 3 OCH 3 CH 2 OCH 2 CH 2 .
  • hydroxyalkyl examples include HOCH 2 CH 2 , HOCH 2 CH 2 CH 2 and HOCH 2 CH 2 CH 2 CH 2 .
  • radicals with carbon atoms those having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are generally preferred.
  • the present invention also provides mixtures comprising stereoisomers which are encompassed by formula (I) or by the formulas of component B (safener).
  • Such compounds of the formula (I) or of the formulas of the component B (safener) contain, for example, one or more asymmetrically substituted carbon atoms or sulfoxides.
  • stereoisomers defined by their specific spatial form such as enantiomers and diastereomers, are all encompassed by the formula (I) or by the formulas of component B (safener) and can be obtained by conventional methods from mixtures of stereoisomers or also by stereoselective reactions in combination be prepared with the use of stereochemically pure starting or auxiliary materials.
  • Methyl 4-amino-3-chloro-6- (5-bromo-2-thiazolyl) pyridine-2-carboxylate (Compound 1-1) Methyl 4-amino-3,5-dichloro-6- (5-chloro -2-furanyl) pyridine-2-carboxylate (Compound I-2) Methyl 4-amino-3-chloro-6- (1-methyl-1H-pyrazol-3-yl) pyridine-2-carboxylate (Compound I -3) Methyl 4-amino-3-chloro-6- (1-methyl-1H-pyrazol-5-yl) pyridine-2-carboxylate (Compound I-4)
  • Methyl 4-amino-3-chloro-6- (3-pyrazolyl) pyridine-2-carboxylate (Compound I-5) Methyl 4-amino-3-chloro-6- (4-triazolyl) pyridine-2-carboxylate (Compound I-6) Methyl 4-amino-3-chloro-6- (5-oxazolyl) pyridine-2-carboxylate (Compound I-7) Methyl 4-amino-3-chloro-6- (2- 5-methyl-1, 3,4-thiadiazolyl)) pyridine-2-carboxylate (Compound I-8)
  • Methyl 4-amino-3-chloro-6- (2-benzthiazolyl) pyridine-2-carboxylate (Compound I-9) MethyM-amino-S-chloro- ⁇ -i-methyl-1H-tetrazol- ⁇ -yl-pyridine ⁇ -carboxylate (Compound 1-10) Methyl 4-amino-3-chloro-6- (2-methyl-2H-tetrazol-5-yl) pyridine-2-carboxylate (Compound 1-11)
  • Methyl 4-amino-3-chloro-6- (3,4-dimethylphenyl) pyridine-2-carboxylate (Compound 1-12) Methyl 4-amino-3-chloro-6- (2,4-dichlorophenyl) pyhdine -2-carboxylate (compound 1-13) Methyl 4-amino-3-chloro-5-fluoro-6- (4-chlorophenyl) pyridine-2-carboxylate (Compound I
  • Methyl-4-amino-3-chloro-6- (5-bromo-2-methoxyphenyl) pyridine-2-carboxylate.
  • Methyl-4-amino-3-chloro-6- (5-bromo-2-methoxyphenyl) -pyridine-2-carboxylate.
  • the application rates are generally lower, z.
  • 0.1 g to 800 g a.i./ha preferably 1 g to 500 g a.i./ha, more preferably 10 g to 400 g a.i./ha.
  • the herbicides of the general formula (I) are suitable for controlling harmful plants, for example in plant crops, for example in economically significant ones Arable farming eg monocotyledonous crops such as cereals (eg wheat, barley, rye, oats), rice, maize, millet or dicotyledonous crops such as sugarbeet, oilseed rape, cotton, sunflower and legumes eg of the genera Glycine (eg Glycine max.
  • monocotyledonous crops such as cereals (eg wheat, barley, rye, oats), rice, maize, millet or dicotyledonous crops such as sugarbeet, oilseed rape, cotton, sunflower and legumes eg of the genera Glycine (eg Glycine max.
  • transgenic glycines max eg conventional varieties such as STS varieties
  • transgenic glycines max eg RR soy or LL soy
  • Phaseolus, Pisum, Vicia and Arachis or vegetable crops from various botanical groups such as potato Leek, cabbage, carrot, tomato, onion, as well as permanent and plantation crops such as pome and stone fruits, soft fruit, wine, hevea, bananas, sugar cane, coffee, tea, citrus, nut orchards, turf, palm tree and forest crops.
  • the herbicide-safener combinations (A) + (B) are also preferred, the use in cereals (eg wheat, barley, rye, oats), rice, corn, millet, sugar beet, sugar cane is particularly preferred , Sunflower, rapeseed and cotton.
  • the herbicide-safener combinations (A) + (B) are also useful in tolerant and non-tolerant mutant cultures and tolerant and intolerant transgenic cultures, preferably of corn, rice, corn, oilseed rape and soy, for example, those directed against imidazolinone herbicides. Atrazine, glufosinate or glyphosate are resistant.
  • the safeners contained as component (B) are compounds which are suitable for reducing phytotoxic effects of crop protection active ingredients such as herbicides on crop plants.
  • S1 a Compounds of the group of heterocyclic carboxylic acid derivatives: S1 a ) compounds of the type dichlorophenylpyrazoline-3-carboxylic acid (S1 a ), preferably compounds such as
  • S1 b dichlorophenylpyrazolecarboxylic acid derivatives (S1 b), preferably compounds such as 1 - (2,4-dichlorophenyl) -5-methylpyrazole-3-carboxylate (S1-2), 1- (2,4-dichlorophenyl) -5-isopropylpyrazol -3-carboxylate
  • S1 d compounds of the type of triazolecarboxylic acids (S1 d ), preferably compounds such as fenchlorazole (ethyl ester), ie 1- (2,4-dichlorophenyl) -5-trichloromethyl- (1H) -1, 2,4-thazole- 3-carboxylic acid ethyl ester (S1-7), and related compounds as described in EP-A-174 562 and US Pat
  • EP-A-346 620 are described;
  • S2 a compounds of the 8-quinolinoxyacetic acid type (S2 a ), preferably (5-chloro-8-quinolinoxy) acetic acid (1-methylhexyl) ester ("cloquintocetmexyl") (S2-1), (5- Chloro-8-quinolinoxy) acetic acid (1, 3-dimethyl-but-1-yl) ester
  • S2 b compounds of the (5-chloro-8-quinolinoxy) malonic acid type (S2 b ), preferably compounds such as (5-chloro-8-quinolinoxy) malonic acid diethyl ester, (5-chloro-8-quinolinoxy) malonic acid diallyl ester, ( 5-chloro-8-quinolinoxy) malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198.
  • R-28725" (3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine) from Stauffer (S3-3),
  • Benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine)
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide
  • AD-67 or "MON 4660” (S-dichloroacetyl-i-oxa-S-aza-spiroK. ⁇ ldecan) of
  • TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8), "diclonone” (dicyclonone) (synonym: “BAS145138” or “LAB 145138”) (RS) -I-
  • R B 1 , RB 2 independently of one another hydrogen, ( C 1 -C 6 ) alkyl,
  • R B 1 cyclopropyl
  • R B 2 hydrogen
  • (R B 3 ) 2-OMe (S4-1, "Cyprosulfamide”)
  • Rc 1 , Rc 2 independently of one another are hydrogen, (C 1 -C 8 ) -alkyl
  • R D 1 is halogen, (dC 4) alkyl, (Ci-C 4) haloalkyl, (C 1 -C 4) AI koxy, (Ci-C 4) haloalkoxy,
  • RD 2 is hydrogen or (Ci-C 4 ) alkyl
  • R D 3 is hydrogen, (C 1 -C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, where each of the abovementioned C-containing radicals is unsubstituted or substituted by one or more preferably up to three identical or different radicals from the group consisting of halogen and alkoxy substituted; or their salts no is an integer from 0 to 2.
  • S9 Agents from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g. i ⁇ -dihydro-hydroxy-i-ethyl-S- ⁇ -tetrazolylcarbonyl-quinolone (CAS Regno: 219479-18-2), 1, 2-dihydro-4-hydroxy-1-methyl-3- (5 tetrazolylcarbonyl) -2-quinolone (CAS No. 95855-00-8), as described in WO-A-1999/000020.
  • S11) oxyimino compound type compounds known as seed dressings, such as those described in US Pat.
  • Oxabetrinil ((Z) -1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (S1 1-1), which is known as millet safener for millet against damage by metolachlor,
  • Fluorofenim (1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-O- (1,3-dioxolan-2-ylmethyl) -oxime) (S1 1-2) used as seed dressing -Safener for millet is known against damage from metolachlor, and
  • Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (S1 1-3), which is known as a seed dressing safener for millet against damage by metolachlor.
  • S12 Isothiochromanone (S12) class agents, e.g. Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS No. 205121-04-6) (S12-1) and related compounds of WO-A -1998 / 13361.
  • S12 Isothiochromanone (S12) class agents, e.g. Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS No. 205121-04-6) (S12-1) and related compounds of WO-A -1998 / 13361.
  • Seed pickling safener for maize known for damage from thiocarbamate herbicides
  • Pretilachlor is known in seeded rice, "flurazole” (benzyl-2-chloro-4-trifluoromethyl-1, 3-thiazole-5-carboxylate) (S13-3), which is used as a seed dressing safener for millet against damage by alachlor and
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, known as safener for corn, "MG-838” (CAS Reg. No. 133993-74-5)
  • Examples of preferred combinations of herbicidal active ingredients (A) and safeners (B) are shown in the following table: (1-1) + (S1-1); (1-1) + (S1-2); (1-1) + (S1-3); (1-1) + (S1-4); (1-1) + (S1-5); (1-1) + (S1-6); (1-1) + (S1-7); (1-1) + (S1-8); (1-1) + (S1-9); (1-1) + (S1-10); (1-1) + (S1-11); (1-1) + (S1-12); (1-1) + (S1-13); (1-1) + (S2-1); (1-1) + (S2-2); (1-1) + (S2-3); (1-1) + (S2-4); (1-1) + (S2-5); (1-1) + (S2-6); (1-1) + (S2-7); (1-1) + (S2-8); (1-1) + (S2-9); (1-1) + (S2-10); (1-1) + (S3-1); (1-1) + (S3-2); (1-1) + (S3-3);

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Catching Or Destruction (AREA)

Abstract

L'invention concerne une composition contenant (A) un ou plusieurs composés de formule (I) ou leurs sels, les indices individuels étant tels que définis dans la description, et (B) un ou plusieurs phytoprotecteurs.
EP09760111A 2008-11-29 2009-11-21 Association d'herbicide(s) et de phytoprotecteur(s) Withdrawn EP2369929A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP09760111A EP2369929A2 (fr) 2008-11-29 2009-11-21 Association d'herbicide(s) et de phytoprotecteur(s)
EP15167337.3A EP2939541A1 (fr) 2008-11-29 2009-11-21 Combinaison d'herbicide-phytoprotecteur
EP15167336.5A EP2939540A1 (fr) 2008-11-29 2009-11-21 Combinaison d'herbicide-phytoprotecteur

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP08020782A EP2191719A1 (fr) 2008-11-29 2008-11-29 Combinaison d'herbicide-phytoprotecteur
PCT/EP2009/008304 WO2010060581A2 (fr) 2008-11-29 2009-11-21 Association d'herbicide(s) et de phytoprotecteur(s)
EP09760111A EP2369929A2 (fr) 2008-11-29 2009-11-21 Association d'herbicide(s) et de phytoprotecteur(s)

Related Child Applications (2)

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EP15167337.3A Division EP2939541A1 (fr) 2008-11-29 2009-11-21 Combinaison d'herbicide-phytoprotecteur
EP15167336.5A Division EP2939540A1 (fr) 2008-11-29 2009-11-21 Combinaison d'herbicide-phytoprotecteur

Publications (1)

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EP2369929A2 true EP2369929A2 (fr) 2011-10-05

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Family Applications (4)

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EP08020782A Withdrawn EP2191719A1 (fr) 2008-11-29 2008-11-29 Combinaison d'herbicide-phytoprotecteur
EP15167336.5A Withdrawn EP2939540A1 (fr) 2008-11-29 2009-11-21 Combinaison d'herbicide-phytoprotecteur
EP09760111A Withdrawn EP2369929A2 (fr) 2008-11-29 2009-11-21 Association d'herbicide(s) et de phytoprotecteur(s)
EP15167337.3A Withdrawn EP2939541A1 (fr) 2008-11-29 2009-11-21 Combinaison d'herbicide-phytoprotecteur

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EP08020782A Withdrawn EP2191719A1 (fr) 2008-11-29 2008-11-29 Combinaison d'herbicide-phytoprotecteur
EP15167336.5A Withdrawn EP2939540A1 (fr) 2008-11-29 2009-11-21 Combinaison d'herbicide-phytoprotecteur

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EP15167337.3A Withdrawn EP2939541A1 (fr) 2008-11-29 2009-11-21 Combinaison d'herbicide-phytoprotecteur

Country Status (7)

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US (2) US8962523B2 (fr)
EP (4) EP2191719A1 (fr)
CN (2) CN102300459A (fr)
AR (1) AR075481A1 (fr)
BR (2) BRPI0921327A8 (fr)
MX (1) MX2011005415A (fr)
WO (1) WO2010060581A2 (fr)

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US8962523B2 (en) 2015-02-24
US20100137137A1 (en) 2010-06-03
BR122015010918A2 (pt) 2015-10-27
EP2191719A1 (fr) 2010-06-02
EP2939540A1 (fr) 2015-11-04
WO2010060581A3 (fr) 2011-09-15
WO2010060581A2 (fr) 2010-06-03
CN105028414A (zh) 2015-11-11
US20150051074A1 (en) 2015-02-19
MX2011005415A (es) 2011-06-16
BRPI0921327A2 (pt) 2015-08-25

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