EP3541188A1 - Inhibiteurs de la cellulose synthase efficaces en tant qu'herbicides - Google Patents

Inhibiteurs de la cellulose synthase efficaces en tant qu'herbicides

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Publication number
EP3541188A1
EP3541188A1 EP17825309.2A EP17825309A EP3541188A1 EP 3541188 A1 EP3541188 A1 EP 3541188A1 EP 17825309 A EP17825309 A EP 17825309A EP 3541188 A1 EP3541188 A1 EP 3541188A1
Authority
EP
European Patent Office
Prior art keywords
cellulose synthase
compound
assay
cellulose
herbicidal
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP17825309.2A
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German (de)
English (en)
Inventor
Steven Gutteridge
Il-Ho Kang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
FMC Corp
Original Assignee
FMC Corp
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Filing date
Publication date
Application filed by FMC Corp filed Critical FMC Corp
Publication of EP3541188A1 publication Critical patent/EP3541188A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N43/80—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • This invention relates to identification and production of herbicidal compounds and compositions which inhibit cellulose synthase.
  • Cellulose is the primary structural component and major load bearing polymer of plant cell walls. In growing cells cellulose microfibrils are laid down transversely reinforcing the cell laterally allowing longitudinal expansion. In plants, cellulose synthesis requires a coordinated transport of substrates across membranes and orientation of the membrane- associated synthase complexes. Cellulose is synthesized by a rosette protein complex composed of cellulose synthases (CESAs). It is thought that the rosette complexes in the primary and secondary cell walls each contain at least three different non-redundant cellulose synthases.
  • CESAs rosette protein complex composed of cellulose synthases
  • CESAl CESA3
  • CESA6 CESA6
  • inhibitors of cellulose synthase at CESA3 and CESA6 are known, an inhibitor of plant cellulose synthase specifically at CESAl is a previously undescribed site of action for herbicides of practical application.
  • One aspect of the present invention is a method for producing a herbicidal composition comprising the following steps:
  • step (c) preparing a herbicidal composition comprising the compound identified in step (a) and verified in step (b).
  • Another aspect of the invention is a method for producing a herbicidal compound comprising testing a candidate compound in a cellulose synthase activity inhibition assay wherein the assay utilizes cellulose synthase from a weed to be controlled.
  • Another aspect of the invention is a method of controlling weeds comprising applying a herbicidally effective amount of a cellulose synthase inhibitor produced by the method described herein to a locus in need of such treatment.
  • a further aspect of the invention is a herbicidal composition comprising a cellulose synthase inhibitor produced by the method described herein as the active ingredient in combination with a carrier.
  • Yet another aspect of the invention is a herbicidal composition comprising a cellulose synthase inhibitor produced by the method described herein in combination with another herbicide.
  • compositions, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process, or method.
  • transitional phrase consisting essentially of is used to define a composition, method that includes materials, steps, features, components, or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention.
  • cellulose synthase inhibition assay refers to assays which measure inhibition of enzymatic activity as well as binding assays and in-silico methods of computer aided molecular design.
  • Indirect inhibitors are relatively inactive compounds that inhibit cellulose synthase following metabolism to an active inhibitor in plants.
  • a "herbicidally effective amount of cellulose synthase inhibitor” refers to an amount of cellulose synthase inhibitor sufficient to kill or inhibit the growth of the weed it is desired to control.
  • weed(s) relates to any unwanted vegetation and includes, for example, undesired carry-over or “rogue” or “volunteer” crop plants in a field of desired crop plants.
  • Isoxaben (N-[3-(l-ethyl-l-methylpropyl)-5-isoxazolyl]-2,6,dimethoxybenzamide CAS Registry No. 82558-50-7) is a preemergence, broad leaf herbicide used primarily on small grain, turf and ornamental cro s.
  • This compound is extremely active with an IC50 for oilseed rape ⁇ Bras ska napus) of
  • Isoxaben inhibits the incorporation of glucose into the cellulose-rich, acid-insoluble fraction of isolated walls and is an extremely powerful and specific inhibitor of cell wall biosynthesis.
  • Cell wall-fractionation studies have revealed that the herbicidal action of isoxaben can be explained entirely by its effect on cellulose biosynthesis (Corio-Costet et al., Pest. Biochem. Phys. 1991, 40, 255-265). The probable mode of action is to directly inhibit cellulose synthesis, because resistant cell lines show an unaltered uptake or detoxification of the herbicide (Heim et al., Pest. Biochem. Phys.
  • ixrA i.e. ixrl
  • ixrB i.e. ixr2
  • isoxaben e.g. seed germination, mitosis, respiration, photosynthesis, and lipid and RNA synthesis.
  • Treated cells fail to elongate with high fidelity and consequently grow isodiametrically (Lefebvre et al., Weed Res. 1987, 27, 125-134).
  • Compound 1 i.e. [3-(3,5-dichlorophenyl)-lH-pyrazol-4- yl]phenyl-methanone described as prepared in U.S. Pat. No. 5,939,559, CAS Registry No. 182141-92-0
  • Compound 1 is a potent inhibitor of plant cellulose synthase specifically at CESA1, a previously undescribed site of action for herbicides of practical application.
  • Arabidopsis Landsberg erecta (Ler-0) seeds were sterilized in chlorine gas and plated on 0.5x Murashige and Skoog salts (MS) plant media (containing 0.05% 2-(N-Morpholino)- ethanesulfonic acid (MES), 0.5% sucrose, and 0.8% Phytagar in a 24-well plate.
  • MS Murashige and Skoog salts
  • MES 2-(N-Morpholino)- ethanesulfonic acid
  • sucrose ethanesulfonic acid
  • Phytagar Phytagar
  • Each well contained 0.01, 0.1, 1, 5, 10 and 100 ⁇ of Compound 1, respectively and the IC50 was determined by measuring fresh weights as well as root lengths compared to untreated control seedlings.
  • the concentration of Compound 1 at which 50% of the fresh weights of untreated seedlings was determined to be the IC 50 concentration.
  • the IC 50 was determined to be 0.05 ⁇
  • Ethyl methanesulfonate (EMS)-mutagenized M 2 seeds of Arabidopsis Ler-0 (M2E- 04-07, Lehle Seeds. Round Rock, TX) were screened, in order to screen resistant mutant Arabidopsis plants to Compound 1, about 12,000 sterilized M 2 seeds were plated on MS plates containing 10 times of the IC 50 concentration of Compound 1 (0.5 ⁇ ). Resistant seedlings were selected after seven to 10 d on selective medium and transferred to soil. Soil-transferred plants were grown in growth chambers in 4-inch (10 cm) pots using Metromix 360 potting soil under cool-white fluorescent light using a 16 h day/8 h night photoperiod at 22 °C.
  • Compound 1 resistance was confirmed in the next generation with the same concentration of herbicide used in the selection.
  • PCR-based mapping as well as SNP (Single Nucleotide Polymorphism) analysis was conducted.
  • Crosses of the mutant to a diverged genome are required in order to reduce unlinked genetic background within selected resistant mutants.
  • BC1 Fl seeds and out-cross 1 (OC1) Fl seeds the selected Compound 1 resistant mutant males were crossed with wild-type Ler-0 females and wild-type Columbia (Col-0) females, respectively.
  • BC2 and OC2 were created from BC1 with wild-type Ler-0 and OC1 with wild-type Col-0 plants, respectively.
  • Compound 1-resistant Fl seeds were generated by pollinating emasculated flowers of wild-type plants with pollen from Compound 1-resistant mutant plants.
  • the generated Fl (BC1 and OC1) and F2 (BC2 and OC2) seeds were plated on MS media containing same concentration of Compound 1 as was used in the original screen.
  • Seedlings showing significantly reduced growth in these concentrations of Compound 1 were used to provide samples for PCR mapping of the F2 genome.
  • Using a combination of chromosomal markers the rough position of the allele responsible for resistance to the compound was mapped to a partial segment of chromosome 4 of the Arabidopsis genome.
  • Cellulose synthase 1 (ATCESA1, AT4G324210) was one of 8 genes that harbored single nucleotide polymorphisms (SNPs) in the relevant segment of chromosome 4.
  • SNPs single nucleotide polymorphisms
  • the method for production of potential herbicides does not require use of any particular cellulose synthase inhibition assay. Suitable assays are described hereinafter, but those skilled in the art can readily substitute functionally equivalent test methods. For example, although the in-vitro screening assay described hereinafter uses A. thaliana seedlings, seedlings of other plants may be substituted. For example a commercially significant weed may be used.
  • the assays to be employed include but are not limited to the group selected from one or more of the following assays: in-vitro activity assays or binding assays.
  • active in the cellulose synthase inhibition assay means that a reduction in cellulose synthase activity is observed.
  • cellulose synthase inhibitor encompasses any compound that: (a) produces measurable inhibition in a cellulose synthase inhibition assay using cellulose synthase from a plant; (b) is not a general enzyme inhibitor, and (c) a compound that was known to have herbicidal activity prior to the filing date of this application. It should be understood that no herbicide was known to have cellulose synthase inhibition at CESA1 as its site of action at the time the present invention was made.
  • step (b) above is "not an inhibitor of CESA3 or CESA6".
  • Preferred cellulose synthase inhibitors are those which produce at least a measurable reduction in cellulose synthase activity when tested at 10 ⁇ g/mL in the A. thaliana seedling assay described hereinafter.
  • Compound 1-treated Arabidopsis seedlings as well as untreated seedlings were incubated in phloroglucinol-HCl staining solution for one day and de-staining step was followed for 1 h with 70% ethanol. Images were taken from stained Arabidopsis roots on a bright-field stereomicroscope (Leica).
  • Example 1 The assay method described in Example 1 was modified to accommodate multiple compounds in microtiter plates by methods well known in the art.
  • the assay was conducted using Falcon® 96- well, flat bottom polystyrene plates having wells arrayed in 12 columns and 8 rows.
  • Preparation of the plates was automated using robotic workstations to dilute the stock compounds and add appropriate volumes of reaction solutions and compounds to the individual wells of the 96-well microtiter plate.
  • Arabidopsis seedings (7-day) were dispensed into wells containing test compounds in MS media and incubated under a 16 h day/8 h night photoperiod at 22 °C.
  • An aqueous solution of phloroglucinol was then added to each well for for 24 h.
  • the stain was removed by washing the wells with 70% ethanol for 1 h and the seedlings inspected under a microscope for staining in the vasculature.
  • ixr isoxaben resistance
  • txr thaxtomin resistance
  • irx irregular xylem
  • rsw radially swollen (effect on root growth)
  • 46R4 CESA1 resistance (line 4).
  • the present invention is directed to herbicidal use of compounds that inhibit cellulose synthase (i.e. at CESA1), as opposed to herbicidal use of compounds that inhibit enzymes generally.
  • An example of a compound that inhibits enzymes generally is diethyl pyrocarbonate, which reacts preferentially with protein thiol and amino groups.
  • the active compound may be tested in a second enzyme assay.
  • a suitable assay for this purpose is, for example, the E. coli alkaline phosphatase assay described by Garen and Levinthal, Biochim. Biophys. ACTA 1960, 38, 470. If the compound is not inhibitory in the second enzyme assay, it may generally be safely concluded that the compound does not inhibit enzymes generally.
  • Biological efficacy of a herbicidal compound in whole organisms is influenced by many factors, including not only intrinsic activity of the compound, i.e. efficiency of its interaction with the target molecule, but also stability of the compound and ability of the compound to be translocated to the target site.
  • the cellulose synthase inhibition assay using seedlings provides a measure of the ability of the compound to translocate and interfere with cellulose synthesis. It will be appreciated by those skilled in the art that once a potential herbicide is detected using the cellulose synthase assay, conventional techniques must be used to determine the usefulness of the compound in various environments.
  • a herbicidally effective amount of the compounds of this invention is determined by a number of factors. The exact concentration of compound required varies with the weed to be controlled, the type formulation employed, the method of application, formulation selected, the particular plant species, climate conditions and the like. Generally, a herbicidally effective amount of compounds of this invention is about 0.005 to 20 kg ha with a preferred range of about 0.01 to 1 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
  • compositions that inhibit cellulose synthase include blackgrass (Alopecurus myosuroides), downy bromegrass (Bromus tectorum), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum), wild oat (Avenafatua), catchweed bedstraw (Galium aparine), bermudagrass (Cynodon dactylon), Surinam grass (Brachiaria decumbens), common cocklebur (Xanthium strumarium), large crabgrass (Digitaria sanguinalis), woolly cupgrass (Eriochloa villosa), giant foxtail (Setaria faberii), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), kochia (Kochia scoparia), lambsquarters (Chenopodium album), morningglory (Ipomoea coccinea), eastern black nights
  • the present invention contemplates the use of other plant cellulose synthase enzymes than that found in A. thaliana. Indeed the skilled artisan is capable of using known plant cellulose synthase sequences to create a consensus sequence useful in the plant cellulose synthase assay employed.
  • the proteins and encoding DNA sequences depicted above are all capable of being used in the present invention.
  • the present invention is not limited to use of sequences such as those exemplified above but rather any plant cellulose synthase protein or encoding nucleic acids are intended.
  • the invention includes the use of any cellulose synthase having at least 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or 99% homology; or having 100% homology to the amino acid identitified as SEQ ID NO: 2 (without taking into account mismatches at the N-terminus). Every integer value in between is intended.
  • amino acid or nucleic acid “identity” is equivalent to amino acid or nucleic acid "homology”).
  • the percent identity between the two sequences is a function of the number of identical positions shared by the sequences, taking into account the number of gaps, and the length of each gap, which need to be introduced for optimal alignment of the two sequences.
  • the comparison of sequences and determination of percent sequence identity between two sequences may be accomplished using a mathematical algorithm.
  • the percent identity between two amino acid sequences is determined using the Needleman and Wunsch (/. Mol. Biol. 1970, 48, 444-53) algorithm, which has been incorporated into the GAP program in the GCG software package (available at www.gcg.com), using either a Blossum 62 matrix or a PAM250 matrix, and a gap weight of 16, 14, 12, 10, 8, 6, or 4 and a length weight of 1, 2, 3, 4, 5, or 6.
  • the percent identity between two nucleotide sequences is determined using the GAP program in the GCG software package (available at www.gcg.com), using a NWSgapdna.CMP matrix and a gap weight of 40, 50, 60, 70, or 80 and a length weight of 1, 2, 3, 4, 5, or 6.
  • a particularly preferred set of parameters is a Blossum 62 scoring matrix with a gap penalty of 12, a gap extend penalty of 4, and a frameshift gap penalty of 5.
  • the percent identity between two amino acid or nucleotide sequences can also be determined using the algorithm of Meyers and Miller (CABIOS 1989, 4, 11-17), which has been incorporated into the ALIGN program (version 2.0), using a PAM120 weight residue table, a gap length penalty of 12 and a gap penalty of 4.
  • the above sequences can be conventionally synthesized by the modified phosphotriester method using fully protected deoxyribonucleotide building blocks. Such synthetic methods are well known in the art and can be carried out in substantial accordance with the procedure of Itakura et al., Science 1977, 198, 1056 and Crea et al, Proc. Nat. Acad. Sci. U.S.A. 1978, 75, 5765. In addition, an especially preferred method is disclosed in Hsiung et al., Nucleic Acid Research 1983, 11, 3227 and Narang et al., Methods in Enzymology 1980, 68, 90. In addition to the manual procedures referenced above, the DNA sequence can be synthesized using automated DNA synthesizers, such as the ABS (Applied Biosystems, 850 Lincoln Centre Drive, Foster City, Calif. 94404) 380B DNA Synthesizer.
  • ABS Applied Biosystems, 850 Lincoln Centre Drive, Foster City, Calif. 94404
  • a compound of this invention will generally be used as a herbicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier.
  • a composition i.e. formulation
  • additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier.
  • the formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
  • Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates and/or suspoemulsions) and the like, which optionally can be thickened into gels.
  • aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion, oil-in-water emulsion, flowable concentrate and suspo-emulsion.
  • nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.
  • compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film- forming solutions or flowable suspensions are particularly useful for seed treatment.
  • Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the active ingredient.
  • An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.
  • Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water, but occasionally another suitable medium like an aromatic or paraffinic hydrocarbon or vegetable oil. Spray volumes can range from about from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting. The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
  • Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.
  • Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g.,
  • Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C6-C22 such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal- sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof.
  • plant seed and fruit oils e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel
  • animal- sourced fats e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil
  • Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation.
  • alkylated fatty acids e.g., methylated, ethylated, butylated
  • Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.
  • the solid and liquid compositions of the present invention often include one or more surfactants.
  • surfactants also known as “surface-active agents”
  • surface-active agents generally modify, most often reduce, the surface tension of the liquid.
  • surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.
  • Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene
  • Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of e
  • Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.
  • amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amine
  • Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon 's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon' s Division, The Manufacturing Confectioner Publishing Co. ; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.
  • compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants).
  • formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes.
  • Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes.
  • formulation auxiliaries and additives include those listed in McCutcheon's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
  • the cellulose synthase inhibitor or indirect inhibitor and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent.
  • Solutions including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water- immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries, with particle diameters of up to 2,000 ⁇ can be wet milled using media mills to obtain particles with average diameters below 3 ⁇ . Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. 3,060,084) or further processed by spray drying to form water-dispersible granules.
  • Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill).
  • Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546.
  • Pellets can be prepared as described in U.S. 4, 172,714.
  • Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5, 180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
  • compositions of this invention can also be mixed with RNA to enhance effectiveness or to confer safening properties.
  • a compositions containing Compound 1 can be mixed with polynucleotides including but not limited to DNA, RNA, and/or chemically modified nucleotides influencing the amount of a particular target through down regulation, interference, suppression or silencing of the genetically derived transcript that render a herbicidal effect.
  • a composition containing a Compound 1 can be mixed with polynucleotides including but not limited to DNA, RNA, and/or chemically modified nucleotides influencing the amount of a particular target through down regulation, interference, suppression or silencing of the genetically derived transcript that render a safening effect.
  • a mixture of one or more of the following herbicides with a compound or composition of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox,
  • herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc, Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.
  • bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc, Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.
  • Compounds of this invention can also be used in combination with plant growth regulators such as aviglycine, N-(phenylmethyl)-lH-purin-6-amine, epocholeone, gibberellic acid, gibberellin A 4 and A 7 , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.
  • plant growth regulators such as aviglycine, N-(phenylmethyl)-lH-purin-6-amine, epocholeone, gibberellic acid, gibberellin A 4 and A 7 , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl
  • plant growth regulators such as aviglycine, N-(phenylmethyl)-lH-purin-6-
  • the weight ratio of these various mixing partners (in total) to the compound or composition of the invention is typically between about 1:3000 and about 3000: 1. Of note are weight ratios between about 1:300 and about 300: 1 (for example ratios between about 1 :30 and about 30: 1).
  • weight ratios between about 1:300 and about 300: 1 for example ratios between about 1 :30 and about 30: 1.
  • One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of weeds controlled beyond the spectrum controlled by the compound or composition of the invention alone.
  • combinations of a compound of this invention with other biologically active (particularly herbicidal) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. synergistic) effect on weeds and/or a less-than-additive effect (i.e. safening) on crops or other desirable plants. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. Ability to use greater amounts of active ingredients to provide more effective weed control without excessive crop injury is also desirable.
  • synergism of herbicidal active ingredients occurs on weeds at application rates giving agronomically satisfactory levels of weed control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load.
  • safening of herbicidal active ingredients occurs on crops, such combinations can be advantageous for increasing crop protection by reducing weed competition.
  • a composition of the present invention can further comprise (in a herbicidally effective amount) at least one additional herbicidal active ingredient having a similar spectrum of control but a different site of action.
  • herbicide safeners such as allidochlor, benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfonamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr- diethyl, mephenate, methoxyphenone naphthalic anhydride (1,8-naphthalic anhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide, N-(aminocarbonyl)- 2-fluorobenzenesulfonamide, l-bromo-4-[(chloromethyl)sulfonyl]benzene
  • herbicide safeners such as allidoch
  • Antidotally effective amounts of the herbicide safeners can be applied at the same time as the compounds of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a compound of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a compound of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener. Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation.
  • composition comprising a compound of the invention (in a herbicidally effective amount), at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners (in an effective amount), and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

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

Abstract

La présente invention concerne l'identification et la production de composés et de compositions herbicides qui inhibent la cellulose synthase.
EP17825309.2A 2016-11-21 2017-11-16 Inhibiteurs de la cellulose synthase efficaces en tant qu'herbicides Withdrawn EP3541188A1 (fr)

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US201662424658P 2016-11-21 2016-11-21
PCT/US2017/061959 WO2018094008A1 (fr) 2016-11-21 2017-11-16 Inhibiteurs de la cellulose synthase efficaces en tant qu'herbicides

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