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
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
• • 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
  • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
  • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
  • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings

Definitions

• This invention relates to compositions and methods for controlling the germination and growth of broadleaf , sedge and grass weeds using compounds comprising thaxtomin, a cyclic dipeptide produced by Streptomyces sp., as an active ingredient.
• Natural products are substances produced by microbes, plants, and other organisms. Microbial natural products offer an abundant source of chemical diversity, and there is a long history of utilizing natural products for pharmaceutical purposes. However, secondary metabolites produced by microbes can also be successfully used for weed and pest control in agricultural applications.
• Thaxtomins (4-nitroindol-3-yl-containing 2,5-dioxopiperazines) are a family of dipeptide phytotoxins produced by plant-pathogenic Streptomyces sp. (S. scabies, S. acidiscabies) that cause scab diseases in potato (Solarium tuberosum) (King, Lawrence et al. 1992).
• Toxin production occurs in diseased tissue and can also be elicited in vitro in an optimal growth medium containing oat bran (Loria, Bukhalid et al. 1995; Beausejour, Goyer et al. 1999). King and her coworkers (King, Lawrence et al. 2001) demonstrated that all plant pathogenic species in the Streptomyces family produce one or more thaxtomins with herbicidal activity.
• Hiltunen et al. Purified four thaxtomin analogs (thaxtomin A, thaxtomin A ortho isomer, thaxtomin B and thaxtomin D) from cultures of S.
• thaxtomin A Figure 1
• thaxtomin D Figure 2
• concentrations of less than 1 uM of thaxtomin A causes cell swelling, necrosis and growth inhibition in mono and dicotyledonous seedlings
• Thaxtomin has been evaluated as an herbicide by Dow Agro Sciences, Inc., and while active, it lacked systemic action (King, Lawrence et al. 2001).
• the presence of the nitro group in the indole ring required for an L, L- configuration of the diketopiperazine appears to be the minimal requirement for phytotoxicity.
• the position of the nitro group in the indole ring is very site specific, and the phenyl portion of the phenylalanine plays a necessary role in structural requirements of phytotoxicity (King, Lawrence et al. 1989; King, Lawrence et al. 1992; King, Lawrence et al. 2003).
• the herbicidal mode of action is based on disruption of cell wall synthesis (Fry and Loria 2002) , with inhibition of cellulose biosynthesis being the main target (King et al., 2001 ; Duval et al., 2005; Johnson et al. 2007).
• Kang et al. Kang, Semones et al. 2008
• a “growth system” may be any ecosystem for growing cereal, pasture grass, Timothy grass and turf grass.
• a "cereal growth system” may be a cereal growth culture or may be a field containing planted cereal crops or cereal seeds.
• a "turf grass growth system” may be a turf grass growth culture or may be a field, lawn or golf course containing planted turf grass or turf grass seeds. It can serve as a safer alternative to synthetic herbicides now on the market.
• a primary object of the invention is to provide novel herbicidal compositions against both broadleaf , sedge and grassy weeds, which include but are not limited to Chenopodium album, Abutilon theophrasti, Helianthus annuus, Ambrosia artemesifolia, Amaranthus retroflexus, Convolvulus arvensis, Brassica kaber, Taraxacum officinale, Solanum nigrum, Malva neglect, Setaria lutescens, Bromus tectorum, Poa annua, Poa pratensis , Lolium perenne L. var. Pace, Festuca arundinaceae Schreb. var.
• Another object is to provide a safe, non-toxic herbicidal composition that does not harm cereal crops, pasture grass, Timothy grass or turf grass and a method that will not harm the environment.
• the present invention is directed to herbicidal compositions containing at least one herbicidal agent, e.g., thaxtomin with optionally certain carriers to control the growth and germination of weeds in the cereal growth system and/or turf grass growth system and/or Timothy grass growth system and/or pasture grass growth system.
• the invention is further directed to an herbicidal composition for use in modulating the germination and growth of monocotyledonous and/or dicotyledenous and/or sedge weeds in a cereal growth system.
• the cereal growth system is a non-rice cereal growth system comprising at least one herbicide in which said herbicide is thaxtomin.
• compositions of the present invention may further comprise a carrier and/or diluent.
• the composition is an aqueous composition.
• the thaxtomin in the composition is dissolved in a diluent comprising an organic solvent such as ethanol, isopropanol, or an aliphatic ketone such as acetone, methyl ethyl ketone, methyl isobutyl ketone.
• the invention is directed to the use of at least one herbicidal agent, e.g., thaxtomin, in formulation of an herbicide for modulating monocotyledonous and/or dicotyledenous and/or sedge weeds a cereal growth system, e.g., a non-rice cereal growth system.
• the invention is directed to the use of at least one herbicidal agent in formulation of an herbicide for modulating monocotyledonous and/or dicotyledenous and/or sedge weeds in a turf grass growth system and/or Timothy grass growth system and/or pasture grass growth system, wherein at least one herbicidal agent is thaxtomin.
• compositions of the present invention may comprise in addition to thaxtomin, at least one or more herbicides.
• the invention may comprise a thaxtomin and a chemical herbicide and/or bioherbicide.
• Compositions comprising thaxtomin and at least a second herbicide may be used in cereal growth systems (e.g., wheat, triticale, barley, oats, rye, corn, sorghum, sugarcane, rice or millet) and/or turf grass growth systems and/or Timothy grass growth systems and/or pasture grass growth systems.
• the invention is directed to a method for selectively modulating germination and growth of monocotyledonous, dicotyledonous and sedge weeds in a cereal crop growth system.
• the cereal growth system is a non-rice cereal crop growth system comprising applying to said weeds or soil in said cereal crop growing system at least one herbicidal agent, wherein said herbicidal agent is thaxtomin, in an amount of effective to modulate germination and growth of said weeds but not modulate growth of cereal crop in said cereal crop growth system.
• the cereal crop may include but is not limited to corn, wheat, triticale, barley, rye, oats, sorghum, sugarcane, and millet.
• the invention is further directed to a method for modulating germination and growth of monocotyledonous, dicotyledonous and sedge weeds in a turf, pasture and/or Timothy grass growth system comprising applying to said weeds or soil in said turf grass growing system at least one herbicidal agent, wherein said herbicidal agent is thaxtomin, in an amount of effective to modulate growth of said weeds but not modulate germination and growth of turf grass in said turf grass growth system, pasture grass in said pasture grass growth system and/or Timothy grass in said Timothy grass growth system.
• the turf grass may be selected from the group consisting of Festuca sp., Poa sp., Bromus sp., Lolium sp., Agrostis sp., Zoysia sp., Cynodon sp.
• the invention is directed to a method for modulating germination and growth of weeds selected from the group consisting of Chenopodium album, Abutilon theophrasti, Helianthus annuus, Ambrosia artemesifolia, Amaranthus retroflexus, Convolvulus arvensis, Brassica kaber, Taraxacum officinale, Solanum nigrum, Malva neglect,, Setaria lutescens, Bromus tectorum, Poa annua, Poa pratensis , Lolium perenne L. var. Pace, Festuca arundinaceae Schreb. var.
• Aztec II, Anthem II, LSI 100, Echinochloa crus-galli comprising applying to said weeds or soil an amount of thaxtomin or salt thereof effective to modulate said germination and growth of said weeds.
• the method of the present invention may also involve the use of at least a second herbicidal agent.
• the two herbicidal agents may be applied together in one formulation or separately in two formulations.
• Control of weeds can be achieved by using thaxtomin A in a tank mix or rotation with other herbicidally active compounds known to have good activity against grass weeds but no or low phytotoxicity against cereal crops and/or turf grass and/or, pasture grass and/or Timothy grasses.
• the invention relates to a method for modulating growth of monocotyledonous , dicotyledonous and sedge weeds comprising applying to said weeds an amount of thaxtomin and amount of at least a second herbicidal agent to modulate growth of said weeds.
• the two herbicidal agents may be applied together in one formulation or separately in two formulations.
• the thaxtomin and second herbicidal agent may be applied in a cereal growth system (e.g., wheat, triticale, barley, oats, rye, corn, sorghum, sugarcane, rice or millet) and/or turf grass growth system and/or pasture grass growth system and/or Timothy grass growth sysem.
• FIGURES Figure 1 shows the structure of Thaxtomin A.
• Thaxtomin utilized in this invention may be derived in fermentation of the following actinomycetes cultures: S. scabies - ATCC 49173 , S. acidiscabies - ATCC 49003 and BL37-EQ-010 - or it can be purchased from commercial sources.
• the thaxtomin utilized in the invention include but are not limited to agents described as cyclic dipeptides having the basic structure cyclo-(L-4-nitrotryptophyl-L-phenylalanyl).
• suitable diketopiperazne moieties may be N-methylated, and include congeners carrying phenylalanyl alpha andring-carbon hydroxyl groups.
• the chemical in a particular embodiment comprises:
• R 1 is methyl or H
• R 2 is hydroxy or H
• R 3 is methyl or H
• R 4 is hydroxy or H
• R 5 is hydroxy or H
• R 6 is hydroxy or H
• Non limiting examples of suitable thaxtomin is for use in accordance with the present invention include but are not limited to thaxtomin A, thaxtomin A ortho isomer, thaxtomin B, thaxtomin C , hydroxy thaxtomin C, thaxtomin A p-isomer, hydroxythaxtomin A and des-N-methylthaxtomin C and derivatives of any of these (See Figure 1).
• the compositions of the present invention may be sprayed on the plant or applied to soil. Particular embodiments are described in the Examples, infra.
• compositions may be in the form of dust, coarse dust, micro granules, granules, wettable powder, emulsifiable concentrate, liquid preparation, suspension concentrate, water degradable granules or oil suspension.
• the compositions of the invention do comprise a carrier and/or diluent.
• 'carrier' as used herein means an inert, organic or inorganic material, with which the active ingredient is mixed or formulated to facilitate its application to plant or other object to be treated, or its storage, transport and/or handling.
• diluents or carriers for the pre- and post-emergence herbicides include, but are not limited to, water, milk, ethanol, mineral oil, glycerol.
• compositions of the present invention may comprise at least two herbicidal agents.
• One herbicidal agent is thaxtomin set forth above. It may be present in one embodiment thaxtomin is present in an amount ranging from about 0.01 to about 5.0 mg/mL.
• the other herbicidal agent may be a bioherbicide and/or a chemical herbicide.
• the bioherbicide may be selected from the group consisting of clove, cinnamon, lemongrass, citrus oils, orange peel oil, tentoxin, cornexistin, AAL-toxin, leptospermone, sarmentine, momilactone B, sorgoleone, ascaulatoxin and ascaulatoxin aglycone.
• the composition may comprise thaxtomin, lemongrass oil and optionally a surfactant and/or vegetable oil.
• the composition may comprise thaxtomin, sarmentine and optionally a nonionic surfactant and/or vegetable oil.
• the bioherbicide such as lemongrass oil or sarmentine may be present in an amount ranging from about 0.1 mg/mL to about 50 mg/mL and more preferably between about 0.5 mg/mL to about 10 mg/mL
• the chemical herbicide may be selected from the group consisting diflufenzopyr and salts thereof, dicamba and salts thereof, topramezone, tembotrione, S-metolachlor, atrazine, mesotrione, primisulfuron-methyl, 2,4- dichlorophenoxy acetic acid, nicosulfuron, thifensulfuron-methyl, asulam, metribuzin, diclofop-methyl, fluazifop, fenoxaprop-p-ethyl, asulam, oxyfluorfen, rimsulfuron, mecoprop, and quinclorac, thiobencarb, clomazone, cyhalofop, propanil, bensul
• the chemical herbicide such as pendimethalin or clomazone may be present in a pre-emergent weed control application in an amount ranging from about 0.5 mg/mL to 15 mg/mL and a chemical herbicide such as cyhalofop, S-metolachlor, bispyribac-sodium, penoxsulam in a post-emergent application from about 1 mg/mL to about 40 mg/mL and more particularly between about 15 mg/ml to about 35 mg/mL.
• the composition may further comprise an adjuvant which may be vegetable oil comprising ethyl oleate, polyethylene dialkyl ester and ethoxylated nonylphenol.
• the composition may additionally comprise a surfactant to be used for the purpose of emulsification, dispersion, wetting, spreading, integration, disintegration control, stabilization of active ingredients, improvement of fluidity or rust inhibition.
• a surfactant to be used for the purpose of emulsification, dispersion, wetting, spreading, integration, disintegration control, stabilization of active ingredients, improvement of fluidity or rust inhibition.
• dispersing and emulsifying agents such as non-ionic, anionic, amphoteric and cationic dispersing and emulsifying agents, and the amount employed is determined by the nature of the composition and the ability of the agent to facilitate the dispersion of the herbicidal compositions of the present invention.
• the formulation components used may contain smectite clays, attapulgite clays and similar swelling clays, thickeners such as xanthan gums, gum Arabic and other polysaccharide thickeners as well as dispersion stabilizers such as nonionic surfactants (for example polyoxyethylene (20) monolaurate or polysorbate 60 POE (20) sorbitan monostearate, ethylene glycol monostearate).
• concentration of the clays may vary between about 0-2.5% w/w of the total formulation
• the polysaccharide thickeners may range between about 0-0.5% w/w of the total formulation
• the surfactants may range from about 0-5% w/w of the total formulation.
• composition and method of the present invention will be further illustrated in the following, non-limiting Examples.
• the examples are illustrative of various embodiments only and do not limit the claimed invention regarding the materials, conditions, weight ratios, process parameters and the like recited herein.
• a pot study is conducted to test the phytotoxicity of thaxtomin A on corn ⁇ Zea mays var. Early Sunglow) and wheat (Triticum aestivum var. PR 1404).
• pigweed Amaranthus sp.
• pigweed is planted in the same pot with either three corn or five wheat seeds, and sprayed simultaneously with the cereal test plants.
• the less than 3-inch tall plants grown under growth lights (12-h light/ 12-h dark) at 28°C are sprayed with thaxtomin A solutions derived from a liquid culture of S.
• thaxtomin A 1.0 mg/mL
• thaxtomin A is planted in each 4"x 4" plastic pot filled with soil. Plants were grown under optimal conditions in a greenhouse before and after treatment with solutions containing 0.5 and 1.0 mg thaxtomin A /mL. At the time of the treatment, the plants are about 3 inches tall. Each treatment is applied in three replicates, and a control treatment included plants treated with just the carrier (4% EtOH, 0.02 % polysorbate 60 POE (20) sorbitan monostearate) . Evaluations for phytotoxicity are performed at 7-day intervals starting one week after treatment. The last evaluation is performed three weeks after the treatment at which point, no phytotoxicity is observed in the treated plants in any treatment concentration.
• EXAMPLE 4 A strain of S. acidiscabies (ATCC-49003) is grown in oat bran broth for 5 days (25°C,
• the extract from a bacterial culture of S. acidiscabies with a thaxtomin A concentration of 0.5 mg/mL or higher showed good efficacy (>50%) against at least three of the most common broadleaf weed species (dandelion, mustard and pigweed) in both cereal and turf growing systems. Control of some weeds such as Black nightshade and Common lambsquarter was not complete but thaxtomin A even at the lower concentration (0.5 mg/mL) results in severe stunting of these weeds. In this same study, no adverse effects are observed in grass species treated with either 0.5 or 1.0 mg/mL thaxtomin A. In all tested grass species, no phytotoxic effects were visible at even the higher thaxtomin A concentration.
• lemongrass oil at 1.25% weight does not improve the efficacy of thaxtomin A (at 0.25 mg/mL) on sedge but it significantly increases the efficacy on grass weeds such as watergrass (field test) and sprangletop (greenhouse test).
• lemongrass oil at 1.25% does not improve the efficacy of thaxtomin A (at 0.25 mg/mL) on sedge but it significantly increases the efficacy on grass weeds such as watergrass (field test) and sprangletop.
• Thaxtomin A (at 0.5 mg/mL) improves the efficacy of an ALS inhibitor, bipyribac sodium; used at half label rate on both sedge and grasses.
• EXAMPLE 6 The efficacy of thaxtomin A derived from a liquid culture of S. acidiscabies is tested in a field study on rice using 4.9 sq-ft plots surrounded by a metal ring. Treatments with either thaxtomin A or thaxtomin A in combination with lemongrass oil (formulated as GreenMatch EX) or cyhalofop (formulated as Clincher CA) were done using a hand-held sprayer with a water volume corresponding to 57 gallons per acre. Rice (variety M209) was grown until maturity and harvested by hand for yield and weed count assessment. Results of yield (kg/ha), and numbers of redstem, small-flower umbrella sedge, and sprangletop in each plot are presented in Table 3 below.
• Means in each column marked with the same letter are not statistically different from each other at p ⁇ 0.05.
• Results indicate that thaxtomin at 180 g/acre significantly reduced the number of sedges but had no effect on sprangletop or yield.
• thaxtomin A 90 g/acre a combination with lemongrass oil had better effect on sedges than a combination with cyhalofop (used at half label rate 52 g/acre).
• Good grass weed (sprangletop) control is achieved when thaxtomin (90 g/acre) is combined with cyhalofop at half the label rate - this combination also improves the yield significantly.
• Cyhalofop (2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propanoic acid, butyl ester) is also mixed together with adjuvant containing ethyl oleate, polyethylene dialky ester and ethoxylated nonylphenol (2.5 % v/v) and increasing concentrations of thaxtomin A (purified from the ATCC strain 49003) at concentrations 0.1 , 0.2 and 0.4 mg/ml.
• the concentrations of the 2-[4-(4-cyano- -fluorophenoxy)phenoxy]propanoic acid, butyl ester before dilution are 29.6% (2.38 lb/gal) and 21.7% (2 lb/gal), respectively.
• the effect of these mixtures on the growth of common water plantain, red stem, smallflower sedge and sprangletop is determined in the greenhouse.
• rice plants of variety M 104 are grown and tested for phytotoxic effects, and all plants are evaluated 7, 14, and 21 days after treatment. Results of from the study with cyhalofop formulated as Clincher CA at the 21 -day evaluation point are presented in Table 4 below.
• Clincher CA 29.6% cyhalofop by weight applied at half label rate (6.5 oz/acre) has good efficacy against grass weeds - not so good on broadleaves and poor on sedges.
• a combination of Clincher CA (cyhalofop) and thaxtomin A provides good control of all rice weeds tested in this study. Efficacy of thaxtomin A against grass weeds is substantially improved if combined with Clincher. Combination of thaxtomin A with Clincher CA did not cause phytotoxicity on rice at any tested concentration.
• Penoxsulam (2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy[l ,2,4]triazolo[l ,5c]pyrimidin-2-yl )-6-trifluoromethyl)benzenesulfonamide) is mixed together with adjuvant containing ethyl oleate, polyethylene dialky ester and ethoxylated nonylphenol (2.5 % v/v) and increasing concentrations of thaxtomin A (purified from the ATCC strain 49003) at concentrations 0.1 , 0.2 and 0.4 mg/ml.
• the concentrations of the 2-[4-(4-cyano- -fluorophenoxy)phenoxy]propanoic acid, butyl ester or 2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy[l ,2,4]triazolo[l ,5c]pyrimidin-2-yl)-6-trifluoromethyl)b enzenesulfonamide before dilution are 29.6% (2.38 lb/gal) and 21.7% (2 lb/gal), respectively.
• the effect of these mixtures on the growth of common water plantain, red stem, smallflower sedge and sprangletop is determined in the greenhouse.
• rice plants of variety M 104 are grown and tested for phytotoxic effects, and all plants are evaluated 7, 14, and 21 days after treatment.
• a strain of S. acidiscabies was grown in oat bran broth for 5 days (25°C, 200 rpm). The whole cell broth was extracted using XAD resin, and the dried crude extract was resuspended in 4% ethanol and 0.2 % non-ionic surfactant at a concentration of 10 mg/mL. The diluted extracts containing 0.2 and 0.4 mg thaxtomin A per mL were tested on three weed species (redstem; Ammania spp., smallflower umbrella sedge; Cyperus difformis and sprangletop: Leptochloa uninervia) .
• Thaxtomin A 0.2 mg/mL 5.0b 48.3b 8.3ab Thaxtomin A 0.4 mg/mL 11.7c* 91.7d 10.0b
• Thaxtomin A at the highest concentration of 0.4 mg/mL provides excellent control of sedge but poor control of the grass weed (sprangletop).
• the efficacy against grass weeds improves significantly.
• efficacy against sedge is improved with the combination treatment compared with the single application of thaxtomin A alone at the corresponding concentration.
• the control of the broadleaf weed (redstem) is poor with all treatments .

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