WO2007051249A1 - Enrobage de graine - Google Patents

Enrobage de graine Download PDF

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Publication number
WO2007051249A1
WO2007051249A1 PCT/AU2006/001642 AU2006001642W WO2007051249A1 WO 2007051249 A1 WO2007051249 A1 WO 2007051249A1 AU 2006001642 W AU2006001642 W AU 2006001642W WO 2007051249 A1 WO2007051249 A1 WO 2007051249A1
Authority
WO
WIPO (PCT)
Prior art keywords
seed dressing
thiosemicarbazone
antifungal
formulation
amount
Prior art date
Application number
PCT/AU2006/001642
Other languages
English (en)
Inventor
Roger Palmerston Heath
Original Assignee
A & C Chemicals Pty Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from AU2005906084A external-priority patent/AU2005906084A0/en
Application filed by A & C Chemicals Pty Ltd filed Critical A & C Chemicals Pty Ltd
Publication of WO2007051249A1 publication Critical patent/WO2007051249A1/fr

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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
    • A01N47/00—Biocides, 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
    • A01N47/08—Biocides, 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products

Definitions

  • This invention is concerned with an antifungal seed dressing. BACKGROUND OF THE INVENTION
  • Such fungal diseases may be controlled by the application of antifungal seed dressing compositions to the seeds of the crops comprising an effective amount of an antifungal compound.
  • antifungal seed dressing compositions to the seeds of the crops comprising an effective amount of an antifungal compound.
  • some species of fungi for example, fungus Tilletia, have developed resistance to the antifungal compounds on the market.
  • Aromatic thiosemicarbazones are effective antifungal agents against bunt (Tilletia spp.), smut (Ustilago spp.), and rice blast (Magnaporthe spp.) and resistant species of the fungus Tilletia.
  • most aromatic thiosemicarbazones are unsuitable for use in seed dressings because the compounds have an extremely unpleasant taste and can act as an irritant if inhaled by a user.
  • Australian Patent No. 498467 describes thiosemicarbazone compounds which have high fungicidal activity, and seed dressing formulations comprising such thiosemicarbazones.
  • Thiosemicarbazone seed dressing formulations of 498467 and the prior art in general are formulated as a powder or suspension concentrate, or
  • the inventor has discovered a method of formulating a thiosemicarbazone in a liquid formulation for use as a seed dressing or mixing a suspension concentration of a thiosemicarbazone with an emulsified oil for use as a seed dressing.
  • the liquid formulation or mixture does not generate dust nor act as an irritant to persons in contact with the formulation and therefore alleviates the problems of the prior art.
  • the invention therefore provides an antifungal seed dressing (i) in the form of a liquid formulation including a thiosemicarbazone of general formula 2 herein and a solvent having the following general formula (Formula 1):
  • the inventor has devised a new liquid thiosemicarbazone formulation that can be used as a seed dressing.
  • the new liquid formulation reduces or eliminates dust generation from treated seeds, thus making the seed dressing commercially acceptable.
  • the liquid formulation is a true solution and comprises a thiosemicarbazone dissolved in the solvent referred to above.
  • the solvents must have the following properties: (i) be non reactive with thiosemicarbazones;
  • the formulation is stable in temperatures that range from -5 degrees to 50 degrees Celsius.
  • thiosemicarbazone any compound with the general formula (Formula 2):
  • R 1 , R 2 and R 3 which may be the same or different, are selected from the group consisting of hydrogen, iodo, bromo, chloro, fluoro, cyano, alkyl or substituted alkyl group containing 1 to 5 carbons, alkoxy group containing 1 to 15 carbons, phenyl or substituted phenyl and naphthyl or substituted naphthyl.
  • suitable substituents for alkyl in the case of Formula 1 and 2 are given in Australian Patent 498467 which is herein incorporated into the specification by reference.
  • the thiosemicarbazone used in the liquid formulation of the invention is selected from the group consisting of para-tolualdehyde thiosemicarbazone (PTT), benzaldehyde thiosemicarbazone, 4- ethylbenzaldehyde thiosemicarbazone, 4-chlorobenzaIdehyde thiosemicarbazone, 4-iso-propylbenzaldehyde thiosemicarbazone, ortho- tolualdehyde thiosemicarbazone, 4-fluorobenzaldehyde thiosemicarbazone.
  • PTT para-tolualdehyde thiosemicarbazone
  • benzaldehyde thiosemicarbazone 4- ethylbenzaldehyde thiosemicarbazone
  • 4-chlorobenzaIdehyde thiosemicarbazone 4-iso-propylbenzaldehyde
  • the amount of thiosemicarbazone included in the formulation and required for effective control of fungi depends on the nature of the thiosemicarbazone, the solubility of the thiosemicarbazone, the strain of fungi to be treated, the degree of control required, the type of medium infected and the conditions under which the formulation is applied to seeds.
  • the amount of thiosemicarbazone included in the liquid formulation falls within the range of 10 to 500 g/L. More preferably, the amount falls within the range 50 to 300 g/L. More preferably, the solvent is diethylene glycol methyl ether.
  • Solvency of the solvent to thiosemicarbazone decreases as the alkyl group R increases in size and also when R 4 or R 5 is CH 3 .
  • High solvency of the solvent to thiosemicarbazone is important, particularly when formulations are stored commercially in a low temperature environment (for example, less than 5 0 C).
  • the liquid formulation may further comprise additives.
  • the additives may be selected from the group consisting of pigments or dyes, insecticides, and
  • the insecticide protects treated seeds and grain from insect attack.
  • Suitable insecticides are selected from, but not limited to, the group consisting of cypermethrin, triflumuron, permethrin, bio-resmethrin, maldison, bifenthrin, imidacloprid, fipronil, alpha-cypermethrin, lambda-cyhalothrin, pirimiphos-methyl and organo-chlorines, such as lindane. More than one insecticide may be included in the formulation to protect the treated seeds or grain from attack by different insect species.
  • the amount of insecticide used in the formulation will depend on the efficacy of the insecticide. Preferably, the amount of insecticide added to the formulation falls within the range of 0.1 to 20 g/L. More preferably, the amount falls within the range of 1 to 10 g/L.
  • the type of pigment or dye included in the formulation depends on the colour and intensity of colour required on the grain or seeds. Suitable dyes and pigments include tartrazine, blue FCF, rhodamine B, phthalocyanine blue, phthalocyanine green, pigment red 57.1 and methyl lake violet.
  • the amount of dye included in the formulation falls within the range 5 to 50 g/L which relates to approximately a 30% solution of dye, or 1.5 to 15 g/L dye solids.
  • the amount of pigments included in the formulation falls within the range 1 to 50 g/L pigment solids.
  • Adhesion agents help improve adhesion of the seed dressing to the grain or seeds.
  • Suitable adhesion agents include, but are not limited to, soluble polymers and/or low vapour pressure solvents, for example, polyvinyl
  • Additional fungicide(s) may be used to control fungal pathogens not affected by thiosemicarbazones.
  • the amount and type of fungicide used depends on the solubility, stability and activity of the fungicide and their effect on thiosemicarbazone solubility and stability.
  • Suitable fungicides may be selected from, but not limited to, the group consisting of thiram, fluazinam, mancozeb, flutriafol, carbendazim, thiabendazole, triadimefon, captan, imazalil, difenoconazole.
  • Co-solvents may increase solubility of the thiosemicarbazone to create a more concentrated formulation and to reduce raw material costs.
  • co-solvent included in the formulation depends on the solubility and efficacy of the thiosemicarbazone included in the formulation.
  • Suitable co-solvents may be selected from, but not limited to, the group consisting of aromatic hydrocarbons (Solvesso®), cyclohexanol, ethylene glycol, propylene glycol, alkylene carbonates (Jeffsol®), glycerol and aliphatic alcohols (n-hexanol).
  • the formulation of the second embodiment of the invention can be prepared using the following detailed procedure.
  • An amount of thiosemicarbazone is slurried in water, using a suitable dispersing agent.
  • the slurry is then milled to the required particle size using standard milling techniques such as ball-milling or bead-milling.
  • a preferred particle size as determined by laser particle size analyzer e.g. Malvern Mastersizer is that 90% of particles are below 30 micrometers and more preferably 90% of particles are below 10 micrometres.
  • the amount of thiosemicarbazone in the slurry is from 10 to 60% by weight, preferably 30 to 50% by weight, but sufficient to enable the desired amount of thiosemicarbazone to be formulated into the final product.
  • the dispersant may be any suitable dispersant known to the art. Such dispersants may be anionic, non-ionic or cationic, such as, but not limited to, lignin sulphonates, naphthalene formaldehyde condensates, alkylphenol alkoxylates, tristyrylphenol alkoxylates, tristyrylphenol alkoxylate phosphates and their salts, fatty alcohol alkoxylates and fatty amine alkoxylates.
  • the amount of dispersant used may be from 1 -10% by weight of the slurry and more preferably 4% by weight of the slurry.
  • a preferred formulation is:
  • Oils suitable for this purpose may be petroleum derived. They may be paraffinic (Recosol®) or isoparaffinic (Isopar®) and have low vapour pressure.
  • suitable oils may be vegetable oils such as, but not limited to, canola, soy and cotton seed.
  • suitable emulsifiers are known to the art and may be anionic, non- ionic or cationic and are added in sufficient amount to enable formulation of a fine emulsion when oil is added to water.
  • the amount of emulsifier used may be from 2-10% of the weight of the oil and more preferably 5.0% of the weight of oil.
  • emulsifiers examples include alkyl-aryl alkoxylates, fatty alcohol alkoxylates, fatty amine alkoxylates, vegetable oil alkoxylates, alkyl- aryl sulphonates, sorbitan esters, alkoxylated sorbitan esters.
  • An especially preferred emulsifier is a mixture of ceto/stearyl alcohol ethoxylate and calcium alkylbenzene sulphonate.
  • a preferred formulation is: Recosol P212 95%
  • Example of pH buffers are ortho- phosphoric acid, potassium dihydrogen phosphate and ammonium dihydrogen phosphate.
  • protective biocides are benzisothiazolone solution (e.g. Proxel® GXL20 and triazine solution (e.g. Glokill® 77).
  • examples of clays are bentonite, attapulgite, diatomaceous earth, and examples of stabilizers arexanthan gum, carboxymethyl cellulose, polyvinyl pyrrolidone, polyethylene glycol and acrylic polymers.
  • the amount of thiosemicarbazone suspension concentrate in the combined formulation may be varied according to the amount of thiosemicarbazone in the suspension concentrate and the desired amount of thiosemicarbazone in the combined formulation.
  • the preferred amount of thiosemicarbazone in the suspension concentrate is from 10 to 60% by weight, more preferably 30 to 50% by weight.
  • the preferred amount of thiosemicarbazone in the combined formulation is from 50 to 500g/L, more preferably 100 to 400g/L.
  • the preferred amount of oil in the combined formulation is 50 to 400g/L, more preferably 150 to 350g/L.
  • seeds which have the dressings of the invention applied thereto may be selected from wheat, barley, oats,
  • FIG 1 shows a schematic representation of a dust measurement apparatus as described herein and FIG 2 shows a plan view of the apparatus shown in FIG 1.
  • Formulations according to this invention are prepared by mixing the required quantity of solvent, thiosemicarbazone and optional ingredients in a glass beaker or other suitable container and stirring at ambient temperature until all ingredients are dissolved. Dressing of seeds
  • seeds may be dressed in several ways: A quantity of seed is placed in a glass jar such that the jar contains approximately 50% bulk volume of seed.
  • a powder seed dressing is used, the required amount of seed dressing is added directly to the jar, which is then capped and shaken or tumbled until there is an even coating of seed dressing on the seed. If a liquid seed dressing is used, the liquid dressing is dribbled down the side of the jar, which is immediately capped and shaken or tumbled until there is an even coating of dressing on the seeds.
  • a partially inflated and sealed plastic bag may be used instead of a glass jar.
  • Seed dressing formulation A preferred formulation is:
  • Solubility of thiosemicarbazones is influenced by the type of substituent on the benzene ring. For example, halogen (Cl, Br) and CN reduce solubility, and ethyl and methoxy increase solubility of thiosemicarbazones.
  • the purpose of this invention was to develop a formulation which would overcome the problems directly associated with the bitter taste of dust emitted from treated grain during commercial use.
  • the inventor designed a device which collects and measures dust emitted from treated grain. A preferred embodiment of the device is shown in FIGS 1 and 2.
  • the apparatus 1 comprises a stainless steel tube 2, which is 1300 mm in length and 100 mm in diameter.
  • One end 3 of the tube may be sealed during use (the bottom end) with a removable, air-tight closure, such as a rubber gasket 4.
  • the tube has four horizontal baffles 5, each in the shape of an inverted "V", placed at 400, 500, 600 and 700 mm from the top of the tube and at 60° angles to each other.
  • Located approximately 350 mm from the bottom of the tube is a 30 mm diameter dust extraction tube 7, leading outside the apparatus, from which air, containing dust, may be extracted and collected by means of a dust filter 8 and pump (not shown).
  • the inlet of the dust extraction tube 9 is centrally placed and angled down to prevent grain from entering the inlet.
  • the type of dust filter used is a commercially available "pro2000" dust mask filter cartridge manufactured by
  • air is drawn through the filter using a standard electrical vacuum pump at a velocity of approximately 15 litres per minute.
  • Dust emission measurement of the seed dressings of the invention was carried out as follows.
  • a weighed quantity of treated grain or seeds is poured centrally into the top 11 of the steel tube of the apparatus, hitting the baffles on the way down and creating dust. After a set time, the vacuum pump is stopped, the filter cartridge is removed and re-weighed, yielding a weight of dust collected.
  • Raxil ⁇ T is a powder seed dressing manufactured by Bayer Cropscience, incorporating the fungicide "tebuconazole”. It was used here for comparison purposes.
  • Germination trials were conducted of seeds treated with a formulation of the invention.
  • the seeds were treated with standard (1 ml/Kg) and double (2 ml/Kg) amounts of formulation. Part of each group of treated seeds was stored at 4O 0 C for 2 weeks.
  • Formulations in accordance with the second embodiment are prepared by mixing a suspension concentrate of the thiosemicarbazone and an emulsified oil together with any optional ingredients in a suitable container and stirring at ambient temperature until the mixture is homogeneous. Dressing of seeds is carried out as described in the example concerning the first embodiment. The measurement of dust emission from the seeds is also
  • P212 emulsifiable oil at a concentration of 312g/L; Red pigment (solids) and pH buffer, stabilizers and water to required volume; and
  • results described above are similar to those obtained in the example of the first embodiment and show that the new formulation (2) reduces the dust omitted in comparison to the untreated grain.
  • the amount of dust emitted from Raxil T treated grain is far greater than the dust emitted from grain or seeds coated with formulation (2) above.

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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 a pour objet un enrobage de graine antifongique de formule (I) sous forme d'un liquide incluant une thiosemicarbazone et un solvant de formule générale suivante HO-[CH(R4)-CH(R5)-O]n-R où R1 représente un groupement alkyle éventuellement substitué en C1-C6, R4 et R5 représentent un atome d'hydrogène ou un groupement méthyle et n=1-4, ou de formule (II) incluant une thiosemicarbazone sous forme d'une suspension concentrée associée à une huile émulsifiée.
PCT/AU2006/001642 2005-11-03 2006-11-02 Enrobage de graine WO2007051249A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU2005906084 2005-11-03
AU2005906084A AU2005906084A0 (en) 2005-11-03 Seed dressing

Publications (1)

Publication Number Publication Date
WO2007051249A1 true WO2007051249A1 (fr) 2007-05-10

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ID=38005358

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/AU2006/001642 WO2007051249A1 (fr) 2005-11-03 2006-11-02 Enrobage de graine

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WO (1) WO2007051249A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104351231A (zh) * 2014-10-11 2015-02-18 中国农业大学 4-氯肉桂醛缩氨基硫脲在防治植物病害中的应用
WO2014146144A3 (fr) * 2013-03-15 2015-02-19 Bayer Cropscience Lp Compositions, additifs, et procédés pour atténuer ou contrôler la poussière des semences
CN104402771A (zh) * 2014-11-26 2015-03-11 玉林师范学院 对羟基苯甲醛缩氨基脲的合成及其在防治植物病害中的应用
US10321677B2 (en) 2013-03-15 2019-06-18 Bayer Cropscience Lp Compositions, additives, and methods for mitigating or controlling seed dust

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB681904A (en) * 1949-04-26 1952-10-29 Bayer Ag Solutions of thiosemicarbazones
GB681905A (en) * 1949-04-29 1952-10-29 Bayer Ag Solutions of thiosemicarbazones
GB854433A (en) * 1957-04-04 1960-11-16 Upjohn Co Cycloheximide thiosemicarbazone and pesticidal compositions containing same
GB1268632A (en) * 1968-03-26 1972-03-29 Wellcome Found Thiosemicarbazones
US4339443A (en) * 1978-09-22 1982-07-13 Fbc Limited Compounds and compositions
US6329378B1 (en) * 1999-02-10 2001-12-11 Anadys Pharmaceuticals, Inc. Hydrazone, hydrazine and thiosemicarbazone derivatives as antifungal agents

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB681904A (en) * 1949-04-26 1952-10-29 Bayer Ag Solutions of thiosemicarbazones
GB681905A (en) * 1949-04-29 1952-10-29 Bayer Ag Solutions of thiosemicarbazones
GB854433A (en) * 1957-04-04 1960-11-16 Upjohn Co Cycloheximide thiosemicarbazone and pesticidal compositions containing same
GB1268632A (en) * 1968-03-26 1972-03-29 Wellcome Found Thiosemicarbazones
US4339443A (en) * 1978-09-22 1982-07-13 Fbc Limited Compounds and compositions
US6329378B1 (en) * 1999-02-10 2001-12-11 Anadys Pharmaceuticals, Inc. Hydrazone, hydrazine and thiosemicarbazone derivatives as antifungal agents

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014146144A3 (fr) * 2013-03-15 2015-02-19 Bayer Cropscience Lp Compositions, additifs, et procédés pour atténuer ou contrôler la poussière des semences
US10321677B2 (en) 2013-03-15 2019-06-18 Bayer Cropscience Lp Compositions, additives, and methods for mitigating or controlling seed dust
CN104351231A (zh) * 2014-10-11 2015-02-18 中国农业大学 4-氯肉桂醛缩氨基硫脲在防治植物病害中的应用
CN104351231B (zh) * 2014-10-11 2016-06-22 中国农业大学 4-氯肉桂醛缩氨基硫脲在防治植物病害中的应用
CN104402771A (zh) * 2014-11-26 2015-03-11 玉林师范学院 对羟基苯甲醛缩氨基脲的合成及其在防治植物病害中的应用
CN104402771B (zh) * 2014-11-26 2016-09-28 玉林师范学院 对羟基苯甲醛缩氨基脲的合成及在防治植物病害中的应用

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