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WO2025132160A1 - Compositions herbicides - Google Patents

Compositions herbicides Download PDF

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Publication number
WO2025132160A1
WO2025132160A1 PCT/EP2024/086468 EP2024086468W WO2025132160A1 WO 2025132160 A1 WO2025132160 A1 WO 2025132160A1 EP 2024086468 W EP2024086468 W EP 2024086468W WO 2025132160 A1 WO2025132160 A1 WO 2025132160A1
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methyl
spp
plants
emergence
compounds
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Inventor
Thomas Auler
Udo Bickers
Herve TOSSENS
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Bayer AG
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Bayer AG
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides

Definitions

  • the invention lies in the technical field of crop protection products that can be used to counter unwanted plant growth on uncultivated land, for preparation of seed or in plant crops, and comprise a combination of at least two herbicides as herbicidally active compounds, wherein the compositions comprise herbicidally active compounds (A) and (B), in which (A) represents flumioxazin and (B) represents (Bl) ethofumesate, or (B2) bixlozone.
  • Compound A i.e. flumioxazin
  • WSSA 14/HRAC E the herbicide class of inhibitors of the protoporphyrinogen IX oxidase
  • the compound is effective as herbicide against a broad spectrum of harmful plants when applied by the pre-emergence method or else by the post-emergence method, with the possibility of non-selective use for control of unwanted plant growth or selective use in plant crops.
  • Compound B 1 i.e. ethofumesate, belongs to the herbicide class of inhibitors of very long-chain fatty acid synthesis (WSSA 15/HRAC N).
  • WSSA 15/HRAC N very long-chain fatty acid synthesis
  • the compound is effective as herbicides against a broad spectrum of harmful plants when applied by the pre-emergence method or else by the post-emergence method, with the possibility of non-selective use for control of unwanted plant growth or selective use in plant crops.
  • Compound B2 i.e. bixlozone, belongs to the herbicide class of inhibitors of deoxy-D-xylulose phosphate synthase (WSSA 13/HRAC F4).
  • WSSA 13/HRAC F4 deoxy-D-xylulose phosphate synthase
  • the compound is effective as herbicides against a broad spectrum of harmful plants when applied by the pre-emergence method or else by the post-emergence method, with the possibility of non-selective use for control of unwanted plant growth or selective use in plant crops.
  • the efficacy of these herbicides against harmful plants is at a high level, but generally depends on the application rate, the form of the respective preparation, the spectrum of harmful plants, the harmful plants to be controlled in each case, climate and soil conditions, etc.
  • a further criterion is the duration of action or the rate of degradation of the herbicide.
  • Other considerations, as the case may be, are changes in the susceptibility of harmful plants which may occur on prolonged use of the herbicides or in a geographically restricted manner. Compensation for losses in action in the case of individual plants by higher application rates of the herbicides is only possible to a limited degree, for example because this frequently worsens the selectivity of the herbicides or because there is no improvement in action, even in the case of a higher application rate.
  • a lower application rate not only reduces the amount of active ingredient required for the application but generally also reduces the amount of formulation auxiliaries needed. Both reduce economic expenditure and improve the environmental compatibility of the herbicide treatment.
  • One way of improving the application profile of an herbicide may be to combine the active ingredient with one or more other active ingredients which contribute to the desired additional properties.
  • compositions of the invention interact in a particularly favourable manner, for example when they are used to control unwanted plant growth in crop plants.
  • crop plants In particular preferred are cereal crops.
  • compositions of the invention may contain further components, for example other active ingredients to counter harmful organisms such as harmful plants, plant-damaging animals or plant-damaging fungi, especially active ingredients from the group of the herbicides, fungicides, insecticides, acaricides, nematicides and miticides, and related substances, or else other kinds of active ingredients for crop protection (e.g. resistance inductors), crop plant-protecting active ingredients (safeners, antidotes), plant growth regulators, and/or additions and/or formulation auxiliaries that are customary in crop protection.
  • the components may be formulated together here (ready-to-use formulation) and employed as such, or they may be formulated separately and employed together, for example in a tankmix or in sequential application.
  • An advantageous property of the inventive combination of herbicides (A) and (B) is found to be that active ingredients (A) and (B) are compatible with one another, meaning that they can be employed together without occurrence of significant chemical incompatibility between the active ingredients (A) and/or (B) that leads to destruction of one or more active ingredients. This avoids any reduction in the active ingredient content in formulations or spray liquors.
  • the favourable compatibility also extends to the biological properties of the active ingredients on combined use. For instance, antagonistic effects are generally not observed in the case of control of harmful plants with the active ingredient combinations of the invention.
  • the active ingredients (A) and (B) are thus particularly suitable for employment together with or in addition to further active ingredients for crop protection or agrochemicals.
  • the combined application enabled permits the utilization of advantageous effects, for example the broadening of the spectrum of harmful plants to be controlled on application, or the reduction of the application rate of the individual herbicides (A) or (B) compared to the respective application rate of the herbicide in question in the case of individual application. It is thus possible to influence the degradation characteristics of the active ingredients and to achieve more favourable conditions for the subsequent growing of crop plants.
  • a further advantage is considered to be that the development of resistances of the harmful plants to the active ingredients can often be significantly reduced or avoided through the combination of active ingredients having different mechanisms of action.
  • the activity in the combination is higher here than the expected sum of the activities of the individual herbicides used.
  • the synergistic effects allow the application rate to be reduced further, a broader spectrum of broadleaved weeds and weed grasses to be controlled, a more rapid onset of the herbicidal action, longer persistence, better control of the harmful plants with only one or a few applications, and extension of the application period possible.
  • the use of the products also reduces the amount of harmful ingredients, such as nitrogen or oleic acid, and their introduction into the soil.
  • the synergistic effects are observed in the case of joint deployment of active ingredients (A) and (B) but can also frequently occur in the case of offset application (splitting). It is also possible to apply the herbicides (A) or (B) or the herbicidal composition (A) and (B) in multiple portions (sequential application). For example, one or more pre-emergence applications may be followed by a postemergence application, or an early post-emergence application may be followed by a moderately late or late post-emergence application. Preference is given to the simultaneous or immediately successive application of the active ingredients of the respective combination, if appropriate in several portions. But application of the individual active ingredients of a combination at different times is also possible and may be advantageous in the individual case.
  • Synergism can be preferably measured by the method described in Examle B. below.
  • herbicidal compositions comprising active ingredient components (A) and (B), as defined above, in a weight ratio of 200:1 to 1:200, preferably 100:1 to 1:100, further preferably 50:1 to 1:50 can be employed. Even further preferred, (A) and (B) are in a weight ratio of 10:1 to 1:10.
  • composition according to the invention may be used in the form of a concentrated formulation or a ready-to-use diluted spray application mixture (tank-mix).
  • a further aspect relates to a method of controlling weed plants in crops of useful plants, characterized in that a composition according to the invention is applied to the weed plants, plants, plant seeds, or to the area on which the weed plants are growing.
  • the herbicidally active compounds of the composition may be applied jointly or separately by the preemergence method, the post-emergence method or by the pre- and post-emergence method to the plants, plant parts, plant seeds or the area under cultivation.
  • the treatment is a pre-emergence treatment.
  • the treatment is a post-emergence treatment.
  • the combination according to the invention can be used for many crop plants, preferably cereals and particularly preferred in wheat and barley.
  • the application rates (indicated as g/ha i.e. grams of active ingredient per hectare), of the herbicide combination are as defined as follows: Flumioxazin may be applied at a rate of between 10 and 200 g ai/ha, preferably between 20 and 100 g ai/ha, more preferably between 30 and 60 g ai/ha.
  • Ethofumesate may be applied at a rate of between 25 and 1000 g ai/ha, preferably between 50 and 500 g ai/ha, more preferably between 100 and 300 g ai/ha.
  • Bixlozone may be applied at a rate of between 50 and 700 g ai/ha, preferably between 100 and 500 g ai/ha, more preferably between 150 and 250 g ai/ha.
  • the combinations of the invention can be used together with other active ingredients such as the active ingredients mentioned (herbicides, fungicides, insecticides, acaricides etc.) and/or plant growth regulators or auxiliaries from the group of additives customary in crop protection, such as adjuvants and formulation aids.
  • active ingredients such as the active ingredients mentioned (herbicides, fungicides, insecticides, acaricides etc.) and/or plant growth regulators or auxiliaries from the group of additives customary in crop protection, such as adjuvants and formulation aids.
  • the combination of the active crop protection ingredients comprising the active ingredients (A) and (B) and optionally further active ingredients are referred to here as “herbicide combination” for short.
  • Their use forms such as formulations or tankmixes are herbicidal products (compositions).
  • the invention therefore also provides the herbicidal products comprising the active ingredient combinations of the invention with additives customary in crop protection, such as adjuvants and formulation aids, and optionally further active crop protection ingredients.
  • the invention also provides for the use of, or the application method using, the active ingredient combinations of the invention as herbicides and plant growth regulators, preferably as herbicides and plant growth regulators having a synergistically active content of the respective active ingredient combination present.
  • required application rates of the respective active ingredient are generally lower compared to individual application.
  • the herbicidal compositions of the invention can also be combined with further herbicides and plant growth regulators, for example to supplement the activity spectrum.
  • Combination partners usable for the compounds according to the invention in mixed formulations or in a tankmix are, for example, known active ingredients based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p- hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as known, for example, from Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 14th edition, The British Crop Protection Council and the Royal Soc.
  • Examples of known herbicides which can be combined with the compounds of the invention include the active ingredients which follow (N.B.: the compounds are designated either by the common name according to the International Organization for Standardization (ISO) or by the chemical name, in some cases together with a standard code number) and always encompass all use forms, such as acids, salts, esters and isomers, such as stereoisomers and optical isomers.
  • ISO International Organization for Standardization
  • the list includes one, and in some cases, also more than one herbicide selected from: acetochlor, acifluorfen, acifluorfen-methyl, acifluorfen-sodium, aclonifen alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, aminopyralid- dimethylammonium, aminopyralid- tripromine, amitrole, ammoniumsulfamate, anilofos, asulam, asulam-potassium, asulam sodium, atrazine, azafenidin, azimsulfuron, beflu
  • dicamba-biproamine dicamba-N,N-Bis(3-aminopropyl)methylamine, dicamba-butotyl, dicamba-choline, dicamba-digly colamine, dicamba-dimethylammonium, dicamba- diethanolamine ammonium, dicamba-diethylammonium, dicamba-isopropylammonium, dicamba- methyl, dicamba-monoethanolamine, dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba- triethanolamine, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl- 1 ,2-oxazolidin-3-one, 2-(2,5- dichlorobenzyl)-4,4-dimethyl- 1 ,2-oxazolidin-3-one, dichlorprop, dichlorprop-butotyl, dichlorpropdimethylammonium, dichhlor
  • the name preferably defines the commercially available form.
  • the combinations can be applied both by the pre-emergence method and by the post-emergence method. This applies both to pre- and post-emergence with respect to the harmful plants and, in the case of selective control of the harmful plants, to pre- or post-emergence of the crop plants.
  • Mixed forms are also possible, for example control of the harmful plants at their pre- or post-emergence stage after emergence of the crop plants.
  • herbicides (A) and (B) have already demonstrated very good to adequate selectivity in a large number of crops, it is possible in principle for phytotoxicities on the crop plants to occur in some crops, and in particular also in the case of mixtures with other, less selective herbicides.
  • combinations of herbicides (A) and (B) comprising the active herbicidal ingredients combined in accordance with the invention and one or more safeners are of particular interest.
  • the safeners which are used in an antidotically effective amount, reduce the phytotoxic side effects of the herbicides/pesticides employed, for example in economically important crops, such as cereals (wheat, barley, rye, maize, rice, millet), sugarbeet, sugarcane, oilseed rape, cotton and soybeans, preferably cereals.
  • nA is an integer value in the range of 0 to 5, preferably 0 to 3;
  • RA 1 is halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, nitro or (Ci-C4)-haloalkyl;
  • WA is an unsubstituted or substituted divalent heterocyclic moiety selected from the group of partially unsaturated or aromatic five-membered heterocycles carrying 1 to 3 hetero ring atoms selected from the group of nitrogen (N) und oxygen (O), and carrying at least one N-atom and not more than one O-atom in the ring, preferably a five-membered heterocyclic moiety selected from the group (WA 1 ) to (WA 4 ),
  • RA 2 is ORA 3 , SRA 3 or NRA 3 RA 4 or a saturated or unsaturated 3- to 7-membered heterocycle containing at least one N-atom and up to 3 heteroatoms, preferably combined with other heteroatoms from the group of O (oxygen) and S (sulfur), and which is linked to the carbonyl group in (SI) via a nitrogen atom, and which ist unsubstituted or substituted by moieties selected from the group of (Ci-C ⁇ -alkyl, (Ci-C4)-alkoxy or possibly substituted phenyl, preferably ORA 3 , NHRA 4 oder NlCHih, particularly ORA 3
  • RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon moiety, preferably containing 1 to 18 C-atoms;
  • RA 4 is hydrogen, (Ci-Ce)-alkyl, (Ci-Ce)-alkoxy or substituted or unsubstituted phenyl;
  • RA 5 is hydrogen, (Ci-Cs)-alkyl, (Ci-Cs)-haloalkyl, (Ci-C4)-alkoxy-(Ci-Cs)-alkyl, cyano or COORA 9 , wherein RA 9 is hydrogen, (Ci-Cs)-alkyl, (Ci-Cs)-haloalkyl, (Ci-C4)-alkoxy-(Ci-C4)-alkyl, (Ci-Ce)-hydroxyalkyl, (C3-Ci2)-cycloalkyl oder tris-(Ci-C4)-alkylsilyl;
  • RA 6 , RA 7 , RA 8 are independently hydrogen, (Ci-Cs)-alkyl, (Ci-Cs)-haloalkyl, (C3-Ci2)-cycloalkyl or substituted or unsubstituted phenyl;
  • RA 10 is hydrogen, (C3-Ci2)-cycloalkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted heteroaryl;
  • Sl b Derivatives of dichlorophenylpyrazolecarboxylic acid (Sl b ), preferably compounds such as ethyl l-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (SI -2), ethyl l-(2,4- dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (Sl-3), ethyl l-(2,4-dichlorophenyl)-5-(l,l- dimethylethyl)pyrazole-3-carboxylate (SI -4) and related compounds as described in EP-A- 333131 and EP-A-269806;
  • Sl c Derivatives of l,5-diphenylpyrazole-3-carboxylic acid (Sl c ), preferably compounds such as ethyl l-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (Sl-5), methyl l-(2- chlorophenyl)-5-phenylpyrazole-3-carboxylate (SI -6) and related compounds as described, for example, in EP-A-268554;
  • Sl d Compounds of the triazolecarboxylic acid type (Sl d ), preferably compounds such as fenchlorazole(-ethyl ester), i.e. ethyl l-(2,4-dichlorophenyl)-5-trichloromethyl-lH-l,2,4- triazole-3-carboxylate (Sl-7), and related compounds, as described in EP-A-174562 and EP-A- 346620;
  • Sl f compounds of the triazolyloxy acetic acid type (Sl f ), preferably compounds such as methyl- ⁇ [l,5-bis(4-chloro-2-fluorophenyl)-lH-l,2,4-triazol-3-yl]oxy ⁇ acetate (Sl-14) or ⁇ [1,5-Bis(4- chloro-2-fluorophenyl)-lH-l,2,4-triazol-3-yl]oxy ⁇ acetic acid (Sl-15) or methyl- ⁇ [5-(4-chloro- 2-fluorophenyl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy ⁇ acetate (Sl-16) or ⁇ [5-(4- chloro-2-fhiorphenyl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy ⁇
  • S2 a Compounds of the 8-quinolinoxy acetic acid type (S2 a ), preferably 1 -methylhexyl (5-chloro-8- quinolinoxy)acetate ("cloquintocet-mexyl") (S2-1), 1,3-dimethylbut-l-yl (5-chloro-8- quinolinoxy)acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3), 1- allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4), ethyl (5-chloro-8-quinolinoxy)acetate (S2-5), methyl (5-chloro-8-quinolinoxy)acetate (S2-6), allyl (5 -chloro- 8-quinolinoxy) acetate (S2-7), 2-(2-propylideneiminoxy)-l -ethyl (5-chloro-8-quinolinoxy)
  • S2 b Compounds of the (5-chloro-8-quinolinoxy)malonic acid type (S2 b ), preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl (5-chloro-8-quinolinoxy)malonate and related compounds, as described in EP-A-0 582 198.
  • R-29148 (3-dichloroacetyl-2,2,5-trimethyl-l,3-oxazolidine) from Stauffer (S3-2),
  • R-28725" (3-dichloroacetyl-2,2-dimethyl-l,3-oxazolidine) from Stauffer (S3-3),
  • PPG-1292 N-allyl-N-[(l,3-dioxolan-2-yl)methyl]dichloroacetamide
  • TI-35 (1-dichloroacetylazepane) from TRI-Chemical RT (S3-8),
  • RA 1 is (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, where the 2 latter radicals are substituted by VA substituents from the group of halogen, (Ci-C4)-alkoxy, (Ci-Ce) -haloalkoxy and (C1-C4)- alkylthio and, in the case of cyclic radicals, also by (Ci-C4)-alkyl and (Ci-C4)-haloalkyl;
  • RA 2 is halogen, (Ci-C -alkyl, (Ci-C4)-alkoxy, CF3; mA is 1 or 2;
  • VA is 0, 1, 2 or 3;
  • RB 3 is halogen, (Ci-C ⁇ -alkyl, (Ci-C4)-haloalkyl or (Ci-C4)-alkoxy and ms is 1 or 2, e.g. those in which
  • RB 1 cyclopropyl
  • RB 2 hydrogen
  • (RB 3 ) 2-OMe
  • RB 1 cyclopropyl
  • RB 2 hydrogen
  • (RB 3 ) 5-Cl-2-OMe (S4-2)
  • RB 1 isopropyl
  • RB 2 hydrogen
  • (RB 3 ) 5-Cl-2-OMe (S4-4) and
  • RB 1 isopropyl
  • RB 2 hydrogen
  • (RB 3 ) 2-OMe (S4-5);
  • Rc 1 , Rc 2 are independently hydrogen, (Ci-Cs)-alkyl, (C3-Cs)-cycloalkyl, (C3-Ce)-alkenyl,
  • Rc 3 is halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, CF3, and me is 1 or 2; for example l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, l-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; S4 d ) Compounds of the N-phenylsulfonylterephthalamide type of the formula (S4 d ) and salts thereof, which are known, for example, from CN 101838227, in which
  • RD 4 is halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, CF3; mo is 1 or 2;
  • RD 5 is hydrogen, (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, (C2-Ce)-alkenyl, (C2-Ce)-alkynyl, (C5-C6)-cycloalkenyl.
  • Active ingredients from the class of the hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives (S5) for example ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4- hydroxybenzoic acid, 3, 5 -dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxy cinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO- A-2005/015994, WO- A-2005/016001.
  • Active ingredients from the class of the 1 ,2-dihydroquinoxalin-2-ones for example 1- methyl-3-(2-thienyl)- 1 ,2-dihydroquinoxalin-2-one, 1 -methyl-3-(2-thienyl)- 1 ,2- dihydroquinoxaline-2-thione, 1 -(2-aminoethyl)-3-(2-thienyl)- 1 ,2-dihydroquinoxalin-2-one hydrochloride, 1 -(2-methylsulfonylaminoethyl)-3-(2-thienyl)- 1 ,2-dihydroquinoxalin-2-one, as described in WO- A-2005/112630.
  • RD 2 is hydrogen or (Ci-C4)-alkyl
  • RD 3 is hydrogen, (Ci-Cs)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or aryl, where each of the aforementioned carbon-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; or salts thereof, no is an integer from 0 to 2.
  • Active ingredients from the class of the 3-(5-tetrazolylcarbonyl)-2-quinolones for example l,2-dihydro-4-hydroxy-l-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No.: 219479- 18-2), l,2-dihydro-4-hydroxy-l-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A- 1999/000020.
  • RE 1 is halogen, (Ci-C4)-alkyl, methoxy, nitro, cyano, CF3, OCF3,
  • YE, ZE are independently O or S,
  • HE is an integer from 0 to 4,
  • RE 2 is (Ci-Cie)-alkyl, (C2-Ce)-alkenyl, (C3-Ce)-cycloalkyl, aryl; benzyl, halobenzyl,
  • RE 3 is hydrogen or (Ci-Ce)-alkyl.
  • Si l Active ingredients of the oxyimino compounds type (Si l), which are known as seed-dressing agents, for example "oxabetrinil” ((Z)-l,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (SI 1-1), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage,
  • luxofenim (l-(4-chlorophenyl)-2,2,2-trifluoro-l -ethanone O-(l,3-dioxolan-2-ylmethyl)- oxime) (SI 1-2), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage, and
  • naphthalic anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed-dressing safener for maize against thiocarbamate herbicide damage,
  • flurazole (benzyl 2-chloro-4-trifluoromethyl-l,3-thiazole-5-carboxylate) (S13-3), which is known as a seed-dressing safener for millet/sorghum against alachlor and metolachlor damage,
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl- 1,3 -dioxolane) (S13-5) from Nitrokemia, which is known as a safener for maize,
  • RH 2 is hydrogen or halogen
  • RH 3 , RH 4 are independently hydrogen, (Ci-Cie)-alkyl, (Cz-Ci6)-alkenyl or (C2-Cie)-alkynyl, where each of the 3 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy, (Ci- C4)-alkylthio, (Ci-C4)-alkylamino, di[(Ci-C4)-alkyl]amino, [(Ci-C4)-alkoxy]carbonyl, [(Ci-C4)-haloalkoxy]carbonyl, (C3-C6)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or (C3
  • RH 3 is (Ci-C4)-alkoxy, (Ci-Crl-alkcnyloxy, (C2-Ce)-alkynyloxy or (C2-C4)-haloalkoxy and
  • RH 4 is hydrogen or (Ci-C4)-alkyl or
  • RH 3 and RH 4 together with the directly attached nitrogen atom represent a four- to eightmembered heterocyclic ring which, as well as the nitrogen atom, may also contain further ring heteroatoms, preferably up to two further ring heteroatoms from the group of N, O and S, and which is unsubstituted or substituted by one or more radicals from the group of halogen, cyano, nitro, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C4)-alkoxy, (C1-C4) -haloalkoxy and (Ci-C4)-alkylthio.
  • Active ingredients which are used primarily as herbicides but also have safener action on crop plants, for example
  • Preferred safeners in combination with the herbicide combinations of the invention are: cloquintocet- mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.
  • the combination comprises mefenpyr-diethyl and cloquintocet-mexyl.
  • the active ingredient combinations can be deployed onto the plants (e.g. harmful plants such as mono- or dicotyledonous weeds or unwanted crop plants), the seed (e.g. grains, seeds or vegetative propagation organs such as tubers or parts of shoots having buds), or the area in which the plants grow (e.g. the growing area).
  • harmful plants such as mono- or dicotyledonous weeds or unwanted crop plants
  • the seed e.g. grains, seeds or vegetative propagation organs such as tubers or parts of shoots having buds
  • the area in which the plants grow e.g. the growing area.
  • the substances can be deployed prior to sowing (if appropriate also by incorporation into the soil), prior to emergence or after emergence. Preference is given to use by the early post-seeding pre-emergence method or by the post-emergence method in plantation crops against harmful plants that have not yet emerged or have already emerged.
  • the application can also be integrated into weed management systems with divided repeated applications (sequentials).
  • examples may be mentioned of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the herbicide combination/composition according to the present invention, without the enumeration being a restriction to certain species.
  • Examples of dicotyledonous harmful plants on which the herbicide combination/composition according to the present invention act efficiently are from amongst the genera Amaranthus spp., Polygonum spp., Medicago spp., Mollugo spp., Cyclospermum spp., Stellaria spp., Gnaphalium spp., Taraxacum spp., Oenothera spp., Amsinckia spp., Erodium spp., Erigeron spp., Senecio spp., Lamium spp., Kochia spp., Chenopodium spp., Lactuca spp., Malva spp., Ipomoea spp., Brassica spp., Sinapis spp., Urtica spp., Sida spp, Portulaca spp., Richardia spp., Ambrosia spp.,
  • dicotyledonous harmful plants species on which the herbicide combination/composition according to the present invention act efficiently are selected from amongst the species Amaranthus spinosus, Amaranthus palmer, Amaranthis rudis, Polygonum convolvulus, Medicago polymorpha, Mollugo verticillata, Cyclospermum leptophyllum, Stellaria media, Gnaphalium purpureum, Taraxacum offi cinale, Oenothera laciniata, Amsinckia intermedia, Erodium cicutarium, Erodium moschatum, Erigeron bonariensis, Senecio vulgaris, Lamium sp., Erigeron canadensis, Polygonum aviculare, Kochia scoparia, Chenopodium album, Lactuca serriola, Malva parviflora, Malva neglecta, Ipomoea hederacea, Ipomoea lacunose, Brassica nigra
  • the herbicidal products of the invention are notable for a rapid onset and long duration of herbicidal action.
  • the rainfastness of the active ingredients in the combinations of the invention is favourable.
  • a particular advantage is that the effective dosages of compounds (A) and (B) that are used in the combinations can be adjusted to such a low level that their soil action is optimally low. Therefore, the use thereof in sensitive crops is not just enabled, but groundwater contamination is also virtually prevented.
  • the inventive combination of active ingredients allows the required application rate of the active ingredients to be reduced considerably.
  • herbicides (A) and (B) achieves performance properties extending beyond what was to be expected on account of the known properties of the individual herbicides for the combination thereof.
  • the herbicidal effects for a particular harmful plant species exceed the expected value as can be estimated by standard methods, for example according to Colby or other extrapolation methods.
  • the expected activity for a given combination of two active ingredients can be calculated according to S.R. Colby (“Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”, Weeds 15 (1967), 20-22) (see below).
  • the synergistic effects therefore permit, for example, a reduction in the application rates of the individual active ingredients, a higher efficacy at the same application rate, the control of species of harmful plants which are as yet uncovered (gaps), elevated residual action, an extended period of efficacy, an elevated speed of action, an extension of the period of application and/or a reduction in the number of individual applications required and - as a result for the user - weed control systems which are more advantageous economically and ecologically.
  • the active ingredient combinations of the invention can preferably be used as herbicides in crops of useful plants that are resistant, or have been made resistant by genetic engineering, to the phytotoxic effects of the herbicides.
  • the active ingredient combinations of the invention can preferably also be used in transgenic crops that are resistant to protoporphyrinogen oxidase (PPO) inhibitors and which are further resistant (a) to one or more growth regulators, for example dicamba, or (b) to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS), hydroxyphenyl-pyruvate dioxygenases (HPPD), or to herbicides from the group of the sulfonylureas, the glyphosates, glufosinates or benzoylisoxazoles and analogous active ingredients.
  • PPO protoporphyrinogen oxidase
  • ALS acetolactate synthases
  • the invention therefore also provides a method of controlling unwanted plant growth, optionally in crops of useful plants, preferably on uncultivated land or in plantation crops, characterized in that herbicide (A) is applied with one or more herbicides of type (B), i.e. Bl, B2 and/or B3, to the harmful plants, parts of plants or plant seeds (seed) or to the growing area.
  • herbicide A
  • B herbicides of type
  • the invention also provides for the use of the combinations of compounds (A)+(B) for control of harmful plants, optionally in crops of useful plants, preferably on uncultivated land and plantation crops, but also for control of harmful plants before the sowing of the subsequent useful plant, such as, in particular, for preparation for seeding ("burn-down application").
  • the active ingredient combinations of the invention may either take the form of mixed formulations of the two components, if appropriate with further active ingredients, additives and/or customary formulation auxiliaries, which are then applied in a customary manner diluted with water or can be prepared as what are called tankmixes by joint dilution of the separately formulated or partially separately formulated components with water.
  • the compounds (A) and (B) or their combinations can be formulated in various ways according to which biological and/or physicochemical parameters are required.
  • general formulation options are: wettable powders (WP), water-soluble powders (SP), emulsifiable concentrates (EC), water- soluble concentrates, aqueous solutions (SL), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, dispersions based on oil or water, oil dispersions (OD), suspoemulsions, suspension concentrates (SC), oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for soil application or scattering, granules (GR) in the form of microgranules, spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV
  • pesticidally active substances such as other herbicides, fungicides, insecticides or other pesticides (for example acaricides, nematicides, molluscicides, rodenticides, aphicides, avicides, larvicides, ovicides, bactericides, viricides etc.), and also with safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or as a tank mix.
  • pesticidally active substances such as other herbicides, fungicides, insecticides or other pesticides (for example acaricides, nematicides, molluscicides, rodenticides, aphicides, avicides, larvicides, ovicides, bactericides, viricides etc.)
  • safeners for example in the form of a finished formulation or as a tank mix.
  • Wettable powders are preparations which can be dispersed uniformly in water and, in addition to the active ingredient, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example poly oxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'- disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate.
  • the active herbicidal ingredients are finely ground, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills
  • Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers).
  • organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents.
  • emulsifiers which may be used are: calcium alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or for example polyoxyethylene sorbitan fatty acid esters.
  • calcium alkylarylsulfonate salts such as calcium dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or for example
  • Dusting products are obtained by grinding the active ingredient with finely distributed solids, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water- or oil-based. They may be produced, for example, by wetgrinding by means of commercial bead mills and optional addition of surfactants as already listed above, for example, for the other formulation types.
  • Emulsions for example oil-in-water emulsions (EW)
  • EW oil-in-water emulsions
  • Granules can be produced either by spraying the active ingredient onto granular inert material capable of adsorption or by applying active ingredient concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium poly acrylate or else mineral oils.
  • Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules - if desired as a mixture with fertilizers.
  • Water-dispersible granules are produced generally by processes such as spray-drying, fluidized bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain 0.1 to 99 per cent by weight, especially 0.2% to 95% by weight, of active ingredients of types (A) and/or (B), the following concentrations being customary, depending on the type of formulation:
  • the active ingredient concentration is, for example, about 10% to 95% by weight, the remainder to 100% by weight consisting of customary formulation constituents.
  • the active ingredient concentration may be about 1% to 90% by weight, preferably 5 to 80 per cent by weight.
  • Formulations in the form of dusts usually contain 5% to 20% by weight of active ingredient; sprayable solutions contain about 0.05 to 80, preferably 2 to 50, per cent by weight (% by weight) of active ingredient.
  • the active ingredient content depends partly on whether the active ingredient is in liquid or solid form and on which granulation auxiliaries and fillers are used.
  • the content in the water-dispersible granules is between 1% and 95% by weight, preferably between 10% and 80% by weight.
  • the active ingredient formulations mentioned optionally comprise the respectively customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, antifoams, evaporation inhibitors and pH- or viscosity-modifying agents.
  • the formulations in the commercial form are diluted if appropriate in a customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Dust-type preparations, granules for soil application or broadcasting and sprayable solutions are not normally diluted further with other inert substances prior to application.
  • the active ingredients can be deployed onto the plants, plant parts, plant seeds or the area under cultivation (soil), preferably on the green plants and plant parts, and optionally additionally onto the soil.
  • One possible use is the joint application of the active ingredients in the form of tankmixes, where the optimally formulated concentrated formulations of the individual active ingredients together are mixed in a tank with water, and the spray liquor obtained is deployed.
  • a joint herbicidal formulation of the inventive combination of active ingredients (A) and (B) has the advantage that it can be applied more easily since the quantities of the components are already set at the correct ratio to one another. Moreover, the auxiliaries in the formulation can be adjusted optimally to one another, whereas a tank mix of different formulations may result in unwanted combinations of auxiliaries.
  • a dusting product is obtained by mixing 10 parts by weight of an active ingredient (A) or (B) or an active ingredient mixture (A) + (B) (and optionally further active ingredient components) and/or salts thereof and 90 parts by weight of talc as inert substance, and comminuting in a beater mill.
  • a wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of an active ingredient/active ingredient mixture, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetting agent and dispersant and grinding the mixture in a pinned-disk mill.
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of an active ingredient/active ingredient mixture with 6 parts by weight of alkylphenol polyglycol ether (Triton® X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example approximately 255 to 277°C) and grinding the mixture in a friction ball mill to a fineness of below 5 microns.
  • alkylphenol polyglycol ether Triton® X 207
  • isotridecanol polyglycol ether (8 EO) 8 EO
  • paraffinic mineral oil oil
  • An emulsifiable concentrate is obtained from 15 parts by weight of an active ingredient/active ingredient mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
  • Water-dispersible granules are obtained by mixing
  • the herbicide application was done with a track sprayer at a spray volume of 300 1 water/ha using a flat fan nozzle XR 8001 at a pressure of 1.8 bar.
  • the formulations shown in the table 2 were used.
  • the methylated rape seed oil adjuvant Mero® was added to each application liquid with 1 1/ha. After the application and air drying the pots were placed back into the glasshouse and allowed to grow on. The pots were irrigated as required for good plant growth.
  • Visual percent of weed control (2 replicates) was rated in intervals after application, indicated in the result tables as days after herbicide application (DAA) on a scale of 0-100. A rating of 0 is defined as no control and 100 as complete control.
  • A efficacy of the active ingredient (A) in % at an application rate of a [g a.i./ha] ;
  • B efficacy of the active ingredient (B) in % at an application rate of b [g a.i./ha] ;
  • E c expected value of the effect of the combination (A)+(B) in % at the combined application rate a+b [g a.i./ha] .

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  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Chemical & Material Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne des compositions comprenant des composés à activité herbicide (A) et (B), (A) représentant la flumioxazine, et (B) représentant l'éthofumesate ou la bixlozone. L'invention concerne en outre un procédé et l'utilisation de la composition herbicide de l'invention pour lutter contre des plantes nuisibles ou pour réguler la croissance.
PCT/EP2024/086468 2023-12-19 2024-12-16 Compositions herbicides Pending WO2025132160A1 (fr)

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EP0094349A2 (fr) 1982-05-07 1983-11-16 Ciba-Geigy Ag Utilisation de dérivés de quinoléine pour protéger des plantes cultivées
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WO1991007874A1 (fr) 1989-11-30 1991-06-13 Hoechst Aktiengesellschaft Pyrazoline pour la protection de plantes cultivees contre les herbicides
EP0492366A2 (fr) 1990-12-21 1992-07-01 Hoechst Schering AgrEvo GmbH Nouveaux dérivés de chloro-5-quinoline-8-acide oxyalkanecarboniques, procédé pour leur préparation et leur utilisation comme antidote d'herbicides
EP0582198A2 (fr) 1992-08-01 1994-02-09 Hoechst Schering AgrEvo GmbH Composés (hétéro-)aryliques substitués, procédé pour leur préparation, compositions les contenant et leur utilisation comme agents de protection
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WO1998027049A1 (fr) 1996-12-19 1998-06-25 Hoechst Schering Agrevo Gmbh Nouveaux derives d'acide 2-fluoroacrylique, nouveaux melanges d'herbicides et d'antidotes et leur utilisation
WO1998038856A1 (fr) 1997-03-04 1998-09-11 Zeneca Limited Compositions pour proteger du riz contre l'acetochlore
WO1999000020A1 (fr) 1997-06-27 1999-01-07 Hoechst Schering Agrevo Gmbh 3-(5-tetrazolylcarbonyle)-2-quinolones et produits phytosanitaires pour plantes utiles les contenant
WO1999016744A1 (fr) 1997-09-29 1999-04-08 Aventis Cropscience Gmbh Amides d'acide benzoique d'acylsulfamoyle, agents phytosanitaires les contenant et procede permettant de les preparer
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WO2002034048A1 (fr) 2000-10-23 2002-05-02 Syngenta Participations Ag Compositions agrochimiques avec des phytoprotecteurs a base de quinoline
WO2004084631A1 (fr) 2003-03-26 2004-10-07 Bayer Cropscience Gmbh Utilisation de composés aromatiques hydroxy comme phytoprotecteurs
WO2005015994A1 (fr) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Utilisation d'aromates hydroxy comme phytoprotecteurs
WO2005016001A1 (fr) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Agents phytoprotecteurs a base de derives d'acide carboxylique aromatiques-aliphatiques
WO2005112630A1 (fr) 2004-05-12 2005-12-01 Bayer Cropscience Gmbh Derives de quinoxalin-2-one, phytoprotecteurs pour plantes utiles contenant ces derives, procede de production et utilisation desdits derives
WO2007023719A1 (fr) 2005-08-22 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent servant à réduire l'attaque chimique et composition herbicide produisant une attaque chimique réduite
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