WO2013037735A1 - Method of controlling parasitic weeds with mixtures comprising herbicidal acetolactate synthase inhibitors and plant growth regulators - Google Patents

Method of controlling parasitic weeds with mixtures comprising herbicidal acetolactate synthase inhibitors and plant growth regulators Download PDF

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Publication number
WO2013037735A1
WO2013037735A1 PCT/EP2012/067652 EP2012067652W WO2013037735A1 WO 2013037735 A1 WO2013037735 A1 WO 2013037735A1 EP 2012067652 W EP2012067652 W EP 2012067652W WO 2013037735 A1 WO2013037735 A1 WO 2013037735A1
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Prior art keywords
mixtures
component
methyl
components
mixture
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English (en)
French (fr)
Inventor
Matthias Pfenning
Hagen Bremer
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BASF Agrochemical Products BV Netherlands
BASF Agrochemical Products BV United States
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BASF Agrochemical Products BV Netherlands
BASF Agrochemical Products BV United States
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Priority to CN201280044695.2A priority Critical patent/CN103841826B/zh
Priority to EP12756223.9A priority patent/EP2755479B1/en
Priority to RS20160893A priority patent/RS55412B1/sr
Priority to US14/343,913 priority patent/US9681661B2/en
Priority to EA201400337A priority patent/EA024816B1/ru
Priority to MDA20140038A priority patent/MD4518C1/ro
Priority to UAA201403624A priority patent/UA115430C2/uk
Priority to CA2845513A priority patent/CA2845513A1/en
Priority to AU2012307557A priority patent/AU2012307557B2/en
Priority to BR112014005714A priority patent/BR112014005714A2/pt
Application filed by BASF Agrochemical Products BV Netherlands, BASF Agrochemical Products BV United States filed Critical BASF Agrochemical Products BV Netherlands
Priority to ES12756223.9T priority patent/ES2600858T3/es
Priority to IN1589CHN2014 priority patent/IN2014CN01589A/en
Publication of WO2013037735A1 publication Critical patent/WO2013037735A1/en
Anticipated expiration legal-status Critical
Priority to ZA2014/02611A priority patent/ZA201402611B/en
Ceased legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/501,3-Diazoles; Hydrogenated 1,3-diazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, 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
    • A01N37/10Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, 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
    • A01N37/42Biocides, 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 containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/561,2-Diazoles; Hydrogenated 1,2-diazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the present invention relates to a method for controlling parasitic weeds, comprising applying to the host plant, the weeds and/or their habitat herbicidal mixtures or compositions comprising one, two or three acetolactate synthase (ALS) inhibitor(s) and one, two or three plant growth regulator(s) (PGR) which act as ethylene modulators.
  • the present invention also relates to a method for improving the yield of the crop plant comprising applying to the host plant, and/or their habitat mixtures comprising components as defined herein.
  • the present invention also relates to herbicidal mixtures comprising one, two or three acetolactate synthase (ALS) inhibitor(s) selected from imazamox or tribenuron-methyl and one, two or three plant growth regulator(s) (PGR) selected from prohexadione, prohexadione-calcium, trinexapac or trinexapac- ethyl, compositions comprising said mixtures and their use for the control of parasitic weeds.
  • ALS acetolactate synthase
  • PGR plant growth regulator
  • Parasitic weeds derive some or all of their sustenance from another plant by
  • Plant growth regulators interact with the hormonal system of the treated plants and regulate the growth of a plant or parts of a plant. They affect developmental processes and differentiation in plants at low dosages without having a nutritive value or being phytotoxic. More specifically, various PGRs can, for example, reduce plant height, stimulate seed germination, induce flowering, darken leaf coloring, minimize lodging of cereals, change the rate of plant growth and modify the timing and efficiency of flowering, fruit formation, ripening, fruit drop, defoliation or quality traits. There are several different classes of plant growth regulators.
  • azoles such as uniconazole and paclobutrazol
  • cyclohexane carboxylates such as trinexapac, trinexapac-ethyl, prohexadione and prohexadione-calcium
  • pyrimidinyl carbinols such as flurprimidol and ancyrnidol
  • quarternary ammoniums such as chlormequat-chloride and mepiquat-chloride
  • sulphonyl-amino phenyl-acetamides such as mefluidide
  • Plant growth regulators operate by various modes of action (W. Rademacher, Ann. Rev. Plant Physiol. Plant Biol. 2000, 51, 501 -531 ).
  • Prohexadione, prohexadione- calcium, trinexapac and trinexapac-ethyl act as inhibitors of aminocyclopropane carboxylic acid (ACC) oxidase and hence inhibit the biosynthesis of ethylene.
  • ACC aminocyclopropane carboxylic acid
  • Ethylene serves as a hormone in plants (http://en.wikipedia.org/wiki/Ethylene, April 201 1 ; Z. Lin et al., "Recent advances in ethylene research", J. Exp. Bot, 2009, 60, 331 1 -3336). It acts at trace levels within the plant by stimulating or regulating the ripening of fruit as well as senescence of vegetative tissues. Ethylene biosynthesis can be induced or inhibited by plant growth regulators (S. F. Yang et al. "Ethylene biosynthesis and its regulation in higher plants”. Ann. Rev. Plant Physiol. 1984, 35, 155-89).
  • inhibitors of ethylene perception include compounds that have a similar shape to ethylene, but do not elicit the ethylene response.
  • One example of an ethylene perception inhibitor is 1 - methylcyclopropene (1 -MCP).
  • WO 2008124431 (A1 ) relates to synergistic mixtures comprising 1 -MCP for improving yield, health and/or vigor of plants.
  • US 201 1/0028324 disloses a method of controlling weeds using mixtures of nonselective herbicides and plant growth regulators. It also relates to mixtures of nonselective herbicides and plant growth regulators and compositions comprising them.
  • Acetolactate synthase (ALS) inhibitors are herbicidally active compounds, which inhibit the branched chain amino acid biosynthesis. They belong to the group B of the HRAC classification system.
  • WO 2003/0121 15 (A2) and WO 2008/124431 (A1 ) relate to herbicide-resistant sunflower plants and methods for controlling broomrape comprising applying, inter alia, acetolactate synthase inhibitors such as imidazolinones or sulfonylureas.
  • EP 1088480 (A1 ) relates to the selective use of imazetapyr in varieties of sunflowers that are resistant or tolerant to said herbicide for the control of
  • Orobanche cernua or Orobanche cumana US 2005/44587 (A1 ) relates to sunflower lines and hybrids that are tolerant to sulfonylurea herbicides and to a method for selective control of undesired vegetation, including parasitic weeds, preferably
  • Orobanche spp. by applying sulfonylurea herbicides to sulfonylurea-tolerant sunflower crops.
  • sulfonylurea herbicides to sulfonylurea-tolerant sunflower crops.
  • HRAC Classification of Herbicides According to Mode of Action
  • compositions which are highly active against parasitic weeds, especially root parasitic weeds.
  • the compositions should have good compatibility with useful plants.
  • the compositions according to the invention should have a broad spectrum of activity and ultimately help increase the yield of the crop plant.
  • herbicidally active mixtures or compositions comprising one, two or three acetolactate synthase (ALS) inhibitor(s) and one, two or three plant growth regulator(s) (PGR) which act as ethylene modulators are very useful for controlling parasitic weeds.
  • ALS acetolactate synthase
  • PGR plant growth regulator
  • the mixtures and compositions according to the invention have better herbicidal activity, i.e. better activity against parasitic weeds, than would have been expected based on the herbicidal activity observed for the individual components.
  • the mixtures and compositions according to the present invention also provide for significantly improved yields of the crop plant.
  • the herbicidal activity to be expected for mixtures and compositions based on the individual component can be calculated using Colby's formula (see below). If the observed activity exceeds the expected additive activity of the individual components, this effect is referred to as "synergism”.
  • the present invention relates to a method for controlling parasitic weeds, comprising applying to the host plant, the weeds and/or their habitat a herbicidal mixture comprising components A) one, two or three herbicidally active compound(s) from the group of acetolactate synthase (ALS) inhibitors, and B) one, two or three plant growth regulator(s) (PGR) which act as ethylene modulators selected from L-2-amino-4-alkoxy-trans-3-butenoic acid, L-canaline, Co++ or Ni++ ions in plant-available forms, n-propyl gallate, n-octyl gallate, n- dodecyl gallate, putrescine, spermine or spermidine, a -aminoisobutyric acid, L- aminocyclopropene-1 -carboxylic acid, salicylic acid, acibenzolar-S-methyl, prohexadione, prohexadione-calcium,
  • paclobutrazole metconazole, uniconazole, 1 -methylcyclopropene, 2,5- norbornadiene, 3-amino-1 ,2,4-triazole or Ag++ ions including their agriculturally acceptable salts or derivatives, in a synergistically effective amount or a composition comprising said mixture.
  • the mixtures or compositions comprising said mixtures are preferably applied in a synergistically effective amount, which is defined by a weight ratio of A) to B) from 1 : 300 to 300 : 1 , preferably from 1 : 100 to 100 : 1 , preferably from 1 : 20 to 20 :1 , preferably from 1 : 3 to 3 : 1 , preferably from 1 :2 to 2 : 1 and also preferably 1 : 1 .
  • the inventive method comprises the application of herbicidal mixtures comprising components A) and B) and as a further ingredient a herbicidal, fungicidal or insecticidal component C).
  • the present invention also relates to mixtures comprising components A) one, two or three herbicidally active compounds selected from imazamox,
  • PGR plant growth regulator
  • prohexadione prohexadione-calcium, trinexapac or trinexapac-ethyl including their agriculturally acceptable salts or derivatives.
  • the mixtures comprise components A) and B) in a synergistically effective amount, which is defined by a weight ratio of A) to B) from 1 : 300 to 300 : 1 , preferably from 1 : 100 to 100 :1 , preferably from 1 : 20 to 20 :1 , preferably from 1 : 3 to 3 : 1 , preferably from 1 : 2 to 2 : 1 and also preferably 1 : 1.
  • the mixture comprises as a further ingredient a fungicidal, herbicidal or insecticidal component C).
  • the term mixture herein relates to combinations of components A), B) and, optionally, C), i.e. active ingredients, which can be applied separately within a time frame that allows simultaneous action of the active ingredients on the plants, preferably within a time-frame of eight weeks, in particular at most 7 days, more particular at most 1 day.
  • ALS inhibitors, or components A) which can be used according to the present invention are sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron,
  • sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron,
  • pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6- dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid-1 -methylethyl ester (CAS 420138-41 -6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]- benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2- pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01 -8); sulfonylaminocarbonyl- triazolinone herbicides
  • PGRs that act as ethylene modulators, herein referred to as components B), which can be used according to the present invention, are ethylene biosynthesis inhibitors, which inhibit the conversion of S-adenosyl-L-methionine into 1 - aminocyclopropane-1 -carboxylic acid (ACC), such as derivatives of vinylglycine, for example L-2-amino-4-alkoxy-frans-3-butenoic acid), hydroxyla mines, for example L- canaline and their structural analogs, for example corresponding oxime ether derivatives, ethylene biosynthesis inhibitors which block the conversion of ACC into ethylene, selected from the group consisting of Co++ or Ni++ ions in plant-available forms or phenolic radical scavengers such as n-propyl gallate, n-octyl gallate, n- dodecyl gallate; polyamines, such as putrescine, spermine or spermidine, structural analogs of ACC, such as
  • monooxygenases whose main action is to block the biosynthesis of gibberellins or structural analogs of ethylene, for example 1 -methylcyclopropene, 2,5-norbornadiene, 3-amino-1 ,2,4-triazole or Ag++ ions.
  • strobilurin fungicides for example, azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, 2-[2-(2,5-dimethyl- phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester and 2-(2-(3-(2,6-di- chlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl- acetamide; or azole fungicides such as tebuconazole, metconazole, prothi
  • succinate dehydrogenase inhibitors such as boscalid, bixafen, fluopyram, penthiopyrad isopyrazam, fluxapyroxad; or carbendazim
  • thiophanatemethyl iprodione, chlorothalonil, mancozeb, procymidone, vinclozolin, famoxadone, triadimenol, fenpropimorph, cymoxanil, prochloraz; or herbicides selected from acetochlor, aclonifen, cycloxydim, tepraloxydim, clethodim, fenoxyaprop, propaquizafop, quizalafop, haloxyfop, pendimethalin, clomazone, metazachlor, Metolachlor, quinmerac, dimethenamid, ethametsulfuron, napropamide, pethoxamide, glyphosate, gluphosinate, sulfentrazone, carfentrazone, trifluralin, flurochloridone, oxadiazone, linuron.
  • component A) is a compound selected from the group of imidazolinones such as imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin and imazethapyr.
  • component A) is a compound selected from the group of imidazolinones consisting of imazamox, imazapyr, imazaquin, imazamethabenz-methyl or mixtures thereof.
  • component A) is a compound selected from the group of imidazolinones consisting of imazamox, imazapyr and imazethapyr or mixtures thereof.
  • component A) is a compound selected from the group of imidazolinones consisting of imazamox and imazapyr or mixtures thereof.
  • component A) is imazamox. According to a preferred embodiment of the invention component A) is a sulfonylurea herbicide.
  • component A) is a compound selected from the group of sulfonylureas such as tribenuron-methyl, flupyrsulfuron, thifensulfuron-methyl, mesosulfuron, imazasulfuron, foramsulfuron, metsulfuron and ethametsulfuron or mixtures thereof.
  • sulfonylureas such as tribenuron-methyl, flupyrsulfuron, thifensulfuron-methyl, mesosulfuron, imazasulfuron, foramsulfuron, metsulfuron and ethametsulfuron or mixtures thereof.
  • component A) is a compound selected from the group of sulfonylureas consisting of tribenuron-methyl, flupyrsulfuron, mesosulfuron, imazasulfuron, foramsulfuron or mixtures thereof.
  • component A) is imazamox, imazapyr or tribenuron-methyl or mixtures thereof. According to a preferred embodiment of the invention component A) is imazamox or tribenuron-methyl or mixtures thereof.
  • component A) is
  • component A) is tribenuron- methyl.
  • component B) is prohexadione, prohexadione-calcium, trinexapac or trinexapac-ethyl or mixtures thereof.
  • component B) is prohexadione or prohexadione-calcium or mixtures thereof.
  • component B) is prohexadione- calcium.
  • component B) is trinexapac.
  • component B) is trinexapac- ethyl.
  • component C) is a fungicidal compound selected from the group of strobilurins such as dimoxystrobin,
  • component C) is a fungicidal compound selected from
  • component C) is a compound selected from the group of pyraclostrobin and kresoxim-methyl.
  • component C) is pyraclostrobin.
  • component C) is a herbicidal compound such as acetochlor, aclonifen, cycloxydim, tepraloxydim, clethodim, fenoxyaprop, propaquizafop, quizalafop, haloxyfop, pendimethalin, clomazone, metazachlor, Metolachlor, quinmerac, dimethenamid, ethametsulfuron, napropamide, pethoxamide, glyphosate, gluphosinate, sulfentrazone, carfentrazone, trifluralin, flurochloridone, oxadiazone, linuron.
  • acetochlor such as acetochlor, aclonifen, cycloxydim, tepraloxydim, clethodim, fenoxyaprop, propaquizafop, quizalafop, haloxyfop,
  • both the pure isomers and mixtures thereof may be used in the compositions according to the invention. If the components A) and/or B) and/or C) have one or more centers of chirality and are thus present as enantiomers or diastereomers, both the pure enantiomers and diastereomers and mixtures thereof may be used in the compositions according to the invention.
  • components A) and/or B) and/or C) have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
  • Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4- alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium or mono-Ci-C4-alkyl, di-Ci- C4-alkyl, tri-Ci-C4-alkyl, tetra-Ci-C4-alkylammonium that can be substituted by hydroxy or phenyl, for example, methylammonium, isopropylammonium, dimethylammonium
  • tetraethylammonium tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyeth- 1 -oxy)eth-1 -ylammonium, di(2-hydroxyeth-1 -yl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
  • Active components A) and/or B) and/or C) having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative in the compositions according to the invention, for example as amides, such as mono- and di-Ci-C6-alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters and also as thioesters, for example as Ci-Cio-alkylthio esters.
  • amides such as mono- and di-Ci-C6-alkylamides or arylamides
  • esters for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters and also as thioesters, for example as Ci-Cio-alkylthio est
  • Preferred mono- and di-Ci-C6-alkylamides are the methyl and the dimethylamides.
  • Preferred arylamides are, for example, the anilides and the 2-chloroanilides.
  • Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1 -methylhexyl) or isooctyl (2-ethylhexyl) esters.
  • Ci-C4-alkoxy-Ci-C4- alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, for example the methoxyethyl, ethoxyethyl or butoxyethyl ester.
  • An example of a straight-chain or branched Ci-Cio-alkylthio ester is the ethylthio ester.
  • the following mixtures as well as the application of said mixtures in the methods according to the invention are particularly preferred.
  • Mixtures comprising exact y one PGR Mixtures comprising exact y two PGRs. Mixtures comprising exact y one ALS inhibitor and exactly one PGR. Mixtures comprising exact y two ALS inhibitors and exactly one PGR. Mixtures comprising exact y three ALS inhibitors and exactly one PGR.
  • Mixtures comprising exact y one ALS inhibitor and exactly two PGRs. Mixtures comprising exact y two ALS inhibitors and exactly two PGRs.
  • Mixtures comprising exactly three ALS inhibitors and exactly two PGRs.
  • binary mixtures includes mixtures comprising 1 , 2 or 3 active herbicidal components A) and either 1 , 2 or 3, PGR components B).
  • ternary compositions includes mixtures comprising 1 , 2 or 3, active components A), one or more, for example 1 , 2 or 3, components B) and one or more, for example 1 , 2 or 3 components C).
  • the weight ratio of the active compounds A:B is generally in the range from 1 :300 to 300:1 , in particular in the range from 1 :100 to 100:1 and preferably in the range from 1 :3 to 3:1 , in particular in the range from 1 :2 to 2:1 and even more preferably 1 :1 .
  • the relative proportions by weight of the components A:B are generally in the range from 1 :300 to 300:1 , preferrably in the range from 1 :100 to 100:1 and preferably in the range from 1 :3 to 3:1 , in particular in the range from 1 :2 to 2:1 and even more preferably 1 :1
  • the weight ratio of the components A:C is generally in the range from 1 :3000 to 3000:1 , preferably in the range from 1 :1000 to 1000:1 , in particular in the range from 1 :100 to 100:1 and particularly preferably in the range from 1 :20 to 20:1 and even more preferably in the range from 1 :3 to 3:1.
  • the weight ratio of the components B:C is generally in the range from 1 :1000 to 1000:1 , preferably in the range from 1 :500 to 500:1 , in particular in the range from 1 :250 to 250:1 and particularly preferably in the range from 1 :75 to 75:1 and even more preferably in the range from 1 :20 to 20:1 .
  • the weight ratio of components A + B to component C is preferably in the range from 1 :1000 to 1000:1 , in particular in the range from 1 :100 to 100:1 and particularly preferably in the range from 1 :5 to 5:1 and even more preferably in the range from 1 :3 to 3:1 .
  • table 1 a The methods applying mixtures compiled in the following tables 1 a to 18a are particularly preferred embodiments of the present invention.
  • table 1 a
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is L-2-amino-4-alkoxy-trans-3-butenoic acid (B.1 ) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.1A.1 to B.1A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is L-canaline (B.2) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.2A.1 to B.2A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is Co++ ions (B.3) in plant-available form and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.3A.1 to B.3A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is Ni++ ions (B.4) in plant-available form and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.4A.1 to B.4A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is n-propyl gallate (B.5) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.5A.1 to B.5A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is n-octyl gallate (B.6) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.6A.1 to B.6A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is n-dodecyl gallate (B.7) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.7A.1 to B.7A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is putrescine (B.8) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.8A.1 to B.8A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is spermine (B.9) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.9A.1 to B.9A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is spermidine (B.10) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.10A.1 to B.10A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is oaminoisobutyric acid (B.1 1 ) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.1 1A.1 to B.1 1A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is L-aminocyclopropene-1 -carboxylic acid (B.12) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.12A.1 to B.12A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is prohexadione (B.13) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.13A.1 to B.13A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is prohexadione-calcium (B.14) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.14A.1 to B.14A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is trinexapac (B.15) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.15A.1 to B.15A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is trinexapac-ethyl (B.16) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.16A.1 to B.16A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is paclobutrazole (B.17) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.17A.1 to B.17A.82)
  • a method according to the invention applying a mixture comprising components A) and B), wherein component B) is uniconazole (B.18) and component A) corresponds to one component A) as identified in each line of table I respectively (Mixtures B.18A.1 to B.18A.82)
  • mixture B14.A51 a mixture of, for example, imazamox and prohexadione-calcium is denominated as mixture B14.A51 or, for example, bensulfuron-methyl and trinexapac- ethyl is denominated as mixture B15.A4.
  • Particularly preferred embodiments of the present invention relate to methods comprising applying mixtures according to table III.
  • the mixtures according to the invention are suitable as herbicides. They are suitable as such or as an appropriately formulated composition. They act against broad-leafed weeds and grass weeds, particularly against Orobanche spp. and Striga spp., particularly Orobanche spp. in crops such as sunflower, oilseedrape, wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants.
  • Another preferred embodiment of the invention relates to a method for controlling parasitic weeds in useful vegetation selected from the group of sunflower, oilseed rape, canola, soybeans, corn, peas, beans and alfalfa.
  • Another preferred embodiment of the invention relates to a method for improving the yield of the crop plant in useful vegetation selected from the group of sunflower, oilseed rape, canola, soybeans, corn, peas, beans and alfalfa.
  • the components of the mixtures may be applied either simultaneously or sequentially or as premix. If administered sequentially, the components may be applied in any order and combination in a suitable time scale, for example, with up to 8 weeks between the time of applying the first component or combination and the time of applying the last component or combination. According to one embodiment the components are applied within 24 hours. More suitably, the components are applied within a few hours, preferably within one hour. In a preferred embodiment of the invention, the herbicide is applied first in case of sequential application. Preferably the components are applied simultanesouly or in sequence. Particularly preferred application sequences D.1 to D.28 of components A), B) and, optionally, C) are listed below in table IV.
  • FIG. 1 d represents particularly preferred embodiments: table 1 d
  • a method for controlling parasitic weeds comprising applying to the host plant, the weeds and/or their habitat, in an application sequence as defined in row D.1 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a.
  • a method for controlling parasitic weeds comprising applying to the host plant, the weeds and/or their habitat, in an application sequence as defined in row D.2 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 3d
  • a method for controlling parasitic weeds comprising applying to the host plant, the weeds and/or their habitat, in an application sequence as defined in row D.3 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 4d
  • a method for controlling parasitic weeds comprising applying to the host plant, the weeds and/or their habitat, in an application sequence as defined in row D.4 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 5d
  • a method for controlling parasitic weeds comprising applying to the host plant, the weeds and/or their habitat, in an application sequence as defined in row D.5 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a.
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.6 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 7d
  • a method for controlling parasitic weeds comprising applying to the host plant, the weeds and/or their habitat, in an application sequence as defined in row D.7 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 8d
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.8 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 9d
  • a method for controlling parasitic weeds comprising applying to the host plant, the weeds and/or their habitat, in an application sequence as defined in row D.9 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 10d
  • a method for controlling parasitic weeds comprising applying to the host plant, the weeds and/or their habitat, in an application sequence as defined in row D.10 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 1 1 d herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.1 1 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 12d
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.12 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a.
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.13 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 14d
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.14 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 15d
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.15 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 16d
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.16 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a.
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.17 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 18d
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.18 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a.
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.19 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a.
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.20 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 21 d A method for controlling parasitic weeds, comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.20 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.21 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 22d
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.22 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 23d
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.23 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 24d
  • a method for controlling parasitic weeds comprising applying to the the host plant, weeds and/or their habitat, in an application sequence as defined in row D.24 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 25d
  • a method for controlling parasitic weeds comprising applying to the host plant, the weeds and/or their habitat, in an application sequence as defined in row D.25 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 26d
  • a method for controlling parasitic weeds comprising applying to the host plant, the weeds and/or their habitat, in an application sequence as defined in row D.26 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 27d
  • a method for controlling parasitic weeds comprising applying to the host plant, the weeds and/or their habitat, in an application sequence as defined in row D.27 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • table 28d
  • a method for controlling parasitic weeds comprising applying to the host plant, the weeds and/or their habitat, in an application sequence as defined in row D.28 of table IV above, herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with pyraclostrobin or herbicidal mixtures that comprise components as compiled in tables 1 a to 18a in combination with kresoxim-methyl.
  • the invention further relates to methods for improving the yield of the crop plant comprising applying herbicidal mixtures in application sequences as described in tables 1 d to 28d. If the components are administered simultaneously, they may be administered as a tank mix or as a pre-formulated mixture of all components or as a pre-formulated mixture of some components tank mixed with the remaining components. The simultaneous or sequential application of components according to the invention can be done repeatedly.
  • a preferred embodiment of the invention is a single
  • Another preferred embodiment of the invention is a double application. Another preferred embodiment of the invention is a triple application. Another preferred embodiment of the invention is a quadruple application.
  • the mixtures and compositions according to the invention can also be used in genetically modified plants.
  • genetically modified plants herein referred to are plants whose genetic material has been modified by the use of recombinant DNA techniques to include an inserted sequence of DNA that is not native to that plant species' genome or to exhibit a deletion of DNA that was native to that species' genome, wherein the modification(s) cannot readily be obtained by cross breeding, mutagenesis or natural recombination alone.
  • a particular genetically modified plant will be one that has obtained its genetic modification(s) by inheritance through a natural breeding or propagation process from an ancestral plant whose genome was the one directly treated by use of a recombinant DNA technique.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides, e. g., by inclusion therein of amino acid mutation(s) that permit, decrease, or promote glycosylation or polymer additions such as prenylation, acetylation farnesylation, or PEG moiety attachment.
  • auxinic herbicides such as dicamba or 2,4-D
  • bleacher herbicides such as 4- hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors
  • ALS acetolactate synthase
  • imidazolinones enolpyruvyl shikimate 3-phosphate synthase (EPSP) inhibitors such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate;
  • EPP enolpyruvyl shikimate 3-phosphate synthase
  • GS glutamine synthetase
  • protoporphyrinogen-IX oxidase inhibitors lipid biosynthesis inhibitors such as acetylCoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering; furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxinic herbicides, or ACCase inhibitors.
  • ACCase acetylCoA carboxylase
  • oxynil i. e. bromoxynil or ioxynil
  • herbicide resistance technologies are, for example, described in Pest Management Science 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian Journal of Agricultural Research 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein.
  • Several cultivated plants have been rendered tolerant to herbicides by mutgenesis and conventional methods of breeding, e. g., Clearfield® oil seed rape (summer rape or winter rape) or Clearfield® sunflower (BASF SE, Germany) being tolerant to imidazolinones, e.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as delta-endotoxins, e. g., CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA,
  • delta-endotoxins e. g., CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA,
  • VIP vegetative insecticidal proteins
  • VIP1 e.g., VIP1 , VIP2, VIP3 or VIP3A
  • insecticidal proteins of bacteria colonizing nematodes e. g., Photorhabdus spp. or Xenorhabdus spp.
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea or barley lectins
  • agglutinins e.g., insecticidal proteins of bacteria colonizing nematodes
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea or barley lectins
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize- RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3- hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases.
  • RIP ribosome-inactivating proteins
  • these insecticidal proteins or toxins are to be understood expressly also as including pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, e. g., WO 02/015701 ).
  • Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073.
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g., in the publications mentioned above.
  • These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles
  • YieldGard® corn cultivars producing the Cry1 Ab toxin
  • YieldGard® Plus corn cultivars producing CrylAb and Cry3Bb1 toxins
  • Starlink® corn cultivars producing the Cry9c toxin
  • Herculex® RW corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]
  • NuCOTN® 33B cotton cultivars producing the Cry1 Ac toxin
  • NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt1 1 (e. g., Agrisure® CB) and Bt176 from
  • Syngenta Seeds SAS, France (corn cultivars producing the CrylAb toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens.
  • proteins are the so-called " pathogenesis-related proteins" (PR proteins, see, e.g., EP-A 392 225), plant disease resistance genes (e. g., potato culti-vars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato, Solanum bulbocastanum) or T4-lyso-zym (e.g., potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylovora).
  • PR proteins pathogenesis-related proteins
  • plant disease resistance genes e. g., potato culti-vars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato, Solanum bulbocastanum
  • T4-lyso-zym
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g., bio-mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve human or animal nutrition, e. g., oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g., Nexera® rape, Dow AgroSciences, Canada).
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
  • a modified amount of ingredients or new ingredients specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
  • seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms.
  • seed describes corns and seeds.
  • the seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
  • the components A), B) and C) according to the present invention, their N-oxides and salts can be converted into customary types of agrochemical compositions, e. g.
  • composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g.
  • compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
  • the compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • the invention relates in particular to herbicidally active mixtures comprising a component A) and component B) and, optionally, a component C), as defined above, and also, in case of compositions, at least one liquid and/or solid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for crop protection compositions.
  • the invention also relates to a mixture formulated as a 1 -component composition
  • a mixture formulated as a 1 -component composition
  • at least one solid or liquid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for crop protection compositions are also formulated as a 1 -component composition.
  • the invention also relates to a mixture formulated as a 2-component composition
  • a mixture formulated as a 2-component composition
  • a first component A a solid or liquid carrier and/or one or more surfactants
  • a second component B and, optionally, a component C
  • a solid or liquid carrier and/or one or more surfactants where additionally both components may also comprise further auxiliaries customary for crop protection compositions.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti- foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g.
  • toluene paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • alcohols e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol
  • glycols DMSO
  • ketones e.g. cyclohexanone
  • esters e.g. lactates, carbonates, fatty acid esters,
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharide powders e.g. cellulose, starch
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof.
  • Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in
  • McCutcheon's, Vol.1 Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes,
  • sulfosuccinates or sulfosuccinamates examples include sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • phosphates are phosphate esters.
  • carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • citric acid is used as an adjuvant.
  • ammonium sulfate is used as an adjuvant.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as
  • alkylisothiazolinones and benzisothiazolinones are alkylisothiazolinones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water-soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • compositions of the invention can for example be formulated as follows:
  • active components A) and/or B) and, optionally, component C) according to the invention and 5-15 wt% wetting agent e.g. alcohol alkoxylates
  • a wetting agent e.g. alcohol alkoxylates
  • the active substances dissolve upon dilution with water.
  • dispersant e. g. polyvinylpyrrolidone
  • organic solvent e.g. cyclohexanone
  • emulsifiers e.g. calcium
  • dodecylbenzenesulfonate and castor oil ethoxylate are dissolved in up to 100 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). Dilution with water gives an emulsion.
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • Emulsions (EW, EO, ES)
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • 20-40 wt% water-insoluble organic solvent e.g. aromatic hydrocarbon
  • This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
  • Suspensions SC, OD, FS
  • 20-60 wt% of active components A) and/or B) and, optionally, component C) according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1 -2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substances.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 0,1 -2 wt% thickener e.g. xanthan gum
  • 50-80 wt% of active components A) and/or B) and, optionally, component C) according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substances.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • active components A) and/or B) and, optionally, component C) according to the invention are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substances.
  • dispersants e.g. sodium lignosulfonate
  • 1 -3 wt% wetting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • active components A) and/or B) and, optionally, component C) according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g.
  • dispersants e.g. sodium lignosulfonate
  • 1 -5 wt% thickener e.g.
  • An oil phase comprising 5-50 wt% of active components A) and/or B) and, optionally, component C) according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g.
  • an isocyanate monomer e.g. diphenylmethene-4,4'-diisocyanatae
  • a protective colloid e.g. polyvinyl alcohol
  • the addition of a polyamine results in the formation of a polyurea microcapsules.
  • the monomers amount to 1 -10 wt%. The wt% relate to the total CS composition.
  • Dustable powders (DP, DS)
  • active components A) and/or B) and, optionally, component C) according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
  • 0.5-30 wt% of active components A) and/or B) and, optionally, component C) according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate).
  • solid carrier e.g. silicate
  • active components A) and/or B) and, optionally, component C) according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
  • organic solvent e.g. aromatic hydrocarbon.
  • compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • Water-soluble concentrates (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds.
  • the compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing.
  • Methods for applying or treating compound I and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material.
  • compound I or the compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, in particular from 0.1 to 0.75 kg per ha.
  • amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seed) are generally required.
  • the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per per hectare.
  • the required application rates of components A) according to the present invention are generally in the range from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/ha of active substance.
  • the required application rates of components B) according to the present invention are generally in the range from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/ha of active substance.
  • the required application rates of components C) according to the present invention are generally in the range from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/ha of active substance.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1 and 1 :1 .
  • the user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components, e. g. comprising components A) and/or components B) and/or components C) may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components, e. g. comprising components A) and/or components B) and/or components C), can be applied jointly (e.g. after tank mix) or consecutively.
  • herbicidal compositions according to the present invention can be done before, during and/or after, preferably during and/or after, the emergence or pennetration to the host roots by the undesirable plants.
  • the herbicidal compositions according to the present invention can be applied pre- or post-emergence or together with the seed of a crop plant. It is also possible to apply the compounds and compositions by applying to seeds of the host plant, pretreated with a composition of the invention.
  • mixtures of the present invention on their own or jointly in combination with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria or with groups of active compounds which regulate growth.
  • other crop protection agents for example with agents for controlling pests or phytopathogenic fungi or bacteria or with groups of active compounds which regulate growth.
  • miscibility with mineral salt solutions which are employed for treating nutritional and trace element
  • Non-phytotoxic oils and oil concentrates can also be added.
  • Postemergence treatments where performed with up to 4 application timings regarding the growth stage of the host plant.
  • Application timings are specified with M, N, O, and P and related to the following growth stages of the host test plants according to the BBCH-scale" Lancashire, P. D., H. Bleiholder, P. Langeluddecke, R. Stauss, T. van den Boom, E. Weber and A. Witzenberger, 1991 : A uniform decimal code for growth stages of crops and weeds. Ann. appl. Biol.
  • Sequential application were performed with the solo active components and compared to the respective mixture.
  • the respectively stated components A) and B) were used as commercially available formulations and, with addition of a solvent system, introduced into the spray medium used for applying the active composition.
  • the spray medium used was water.
  • Imazamox was used as commercial aqueous solution (SL) having an active ingredient concentration of 40 g/liter (Pulsar 40 ®).
  • Prohexadione- calcium was used as commercial water dispersible granules (WG) having an active ingredient concentration of 100 g/kg (Regalis ®).
  • test period extended over 1 to 4 month. During this time, the plants were tended, and their response to the individual treatments was evaluated.
  • Evaluation was carried out using a scale from 0 to 100 to express activity (in %). 100% means no emergence of the parasitic plants, or complete destruction of at least the above-ground parts, and 0% means no damage or normal course of growth of the parasitic plants. Good herbicidal activity is given at values of at least 70, and very good herbicidal activity is given at values of at least 85.
  • X percent activity using active component A) at an application rate a;
  • E expected activity (in %) by A) + B) at application rates a + b. If the value found experimentally is higher than the value E calculated according to Colby, a synergistic effect is present.

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PCT/EP2012/067652 2011-09-13 2012-09-10 Method of controlling parasitic weeds with mixtures comprising herbicidal acetolactate synthase inhibitors and plant growth regulators Ceased WO2013037735A1 (en)

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AU2012307557A AU2012307557B2 (en) 2011-09-13 2012-09-10 Method of controlling parasitic weeds with mixtures comprising herbicidal acetolactate synthase inhibitors and plant growth regulators
RS20160893A RS55412B1 (sr) 2011-09-13 2012-09-10 Postupak za kontrolu parazitskih korova sa smešom koja sadrži imazamoks i regulatore rasta biljaka
US14/343,913 US9681661B2 (en) 2011-09-13 2012-09-10 Method of controlling parasitic weeds with mixtures comprising herbicidal acetolactate synthase inhibitors and plant growth regulators
EA201400337A EA024816B1 (ru) 2011-09-13 2012-09-10 Способы борьбы с паразитными сорняками при помощи смесей, включающих гербицидные ингибиторы ацетолактатсинтазы и регуляторы роста растений
MDA20140038A MD4518C1 (ro) 2011-09-13 2012-09-10 Procedeu de combatere a buruienilor parazite cu amestecuri erbicide ce conţin inhibitori ai acetolactat sintazei şi regulatori de creştere a plantelor
UAA201403624A UA115430C2 (uk) 2011-09-13 2012-09-10 Спосіб боротьби з паразитними бур'янами за допомогою сумішей, що включають гербіцидні інгібітори ацетолактатсинтази й регулятори росту рослин
CA2845513A CA2845513A1 (en) 2011-09-13 2012-09-10 Method of controlling parasitic weeds with mixtures comprising herbicidal acetolactate synthase inhibitors and plant growth regulators
CN201280044695.2A CN103841826B (zh) 2011-09-13 2012-09-10 用包含除草的乙酰乳酸合酶抑制剂和植物生长调节剂的混合物控制寄生杂草的方法
EP12756223.9A EP2755479B1 (en) 2011-09-13 2012-09-10 Method of controlling parasitic weeds with mixtures comprising imazamox and plant growth regulators
BR112014005714A BR112014005714A2 (pt) 2011-09-13 2012-09-10 método para o controle das ervas daninhas parasitas, método para aumentar o rendimento do vegetal de cultura, mistura, utilização e composições
ES12756223.9T ES2600858T3 (es) 2011-09-13 2012-09-10 Método de control de malezas parásitas con mezclas que comprenden imazamox y reguladores del crecimiento de las plantas
IN1589CHN2014 IN2014CN01589A (https=) 2011-09-13 2012-09-10
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WO2014201326A1 (en) * 2013-06-13 2014-12-18 Monsanto Technology Llc Acetyl-coa carboxylase modulators
WO2014199295A1 (en) * 2013-06-14 2014-12-18 Upl Limited Weed control
WO2015197831A1 (en) * 2014-06-26 2015-12-30 Basf Agrochemical Products B.V. Seed treatment with acetolactate synthase (als) inhibitors
US10207995B2 (en) 2013-06-13 2019-02-19 Monsanto Technology Llc Acetyl CoA carboxylase modulators
WO2020126584A1 (en) 2018-12-18 2020-06-25 Basf Agrochemical Products B.V. Herbicidal combinations
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CN105454271A (zh) * 2016-02-06 2016-04-06 江苏省农用激素工程技术研究中心有限公司 用于防除甘蔗田杂草的除草组合物
CN105532703B (zh) * 2016-02-06 2018-03-27 江苏省农用激素工程技术研究中心有限公司 用于防治甘蔗田杂草的除草组合物
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