WO2016087971A1 - Composition pesticide liquide stabilisée à base d'acéphate - Google Patents

Composition pesticide liquide stabilisée à base d'acéphate Download PDF

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Publication number
WO2016087971A1
WO2016087971A1 PCT/IB2015/058862 IB2015058862W WO2016087971A1 WO 2016087971 A1 WO2016087971 A1 WO 2016087971A1 IB 2015058862 W IB2015058862 W IB 2015058862W WO 2016087971 A1 WO2016087971 A1 WO 2016087971A1
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WO
WIPO (PCT)
Prior art keywords
formulation
concentration
stem
citrus
application
Prior art date
Application number
PCT/IB2015/058862
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English (en)
Inventor
Johannes Jacobus Lodewicus Pretorius
Ian Francois BRINK
Original Assignee
Bitrad Trust
Spectrum Research Services (Proprietary) Limited
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
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Application filed by Bitrad Trust, Spectrum Research Services (Proprietary) Limited filed Critical Bitrad Trust
Publication of WO2016087971A1 publication Critical patent/WO2016087971A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
    • A01N57/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing acyclic or cycloaliphatic radicals

Definitions

  • This invention relates to a stabilized liquid pesticide formulation comprising 0,S-dimethyl acetylphosphoramidothioate, commonly known as acephate, and the use of the undiluted formulation in a method of crop treatment, in particular, but not exclusively, in a method of treating citrus and other tree crops.
  • Acephate is an insecticidal active compound described in, for example, The Pesticide Manual, 8 th edition, page 1 (1987, The British Crop Protection Council). Acephate has the ula:
  • acephate is not very stable in conventional non-solid pesticidal formulations, such that a vigorous decomposition of acephate in these conventional formulations takes place depending on storage conditions and, as a result of this instability, the insecticidal activity of acephate cannot be fully utilized.
  • methamidophos Plants and crops grown with the use of methamidophos include ornamentals, potatoes, pome fruit, stone fruit, citrus fruit, subtropical tree crops, vines, hops, brassicas, beet, cotton, maize, tobacco and others.
  • Methamidophos is classified as a WHO Toxicity Class "Class 1b, Highly Hazardous” compound, while acephate is classified as "Class III, Slightly Hazardous”. Methamidophos is regarded as toxic and the high mammalian toxicity necessitates extra precautions and care by the operators in the handling and application procedures. It is rapidly absorbed through the stomach, lungs, and skin in humans.
  • the acute oral LD 50 for methamidophos in male rats has been reported as 15.6 mg/kg, while the LD 5 o for acephate in male rats has been reported as 1447 mg/kg.
  • US Patent no. 5,698,540 to Sumitomo Chemical Company discloses a stabilized pesticidal composition comprising acephate and one or more N- alkyl-2-pyrrolidones. It is reported here that the storage stability of acephate bulk or acephate in acephate containing liquid formulations is improved by the addition of N-alkyl-2-pyrrolidone(s).
  • the liquid pesticidal compositions of this invention may further include an emulsifier, a solvent, and/or other pesticidal ingredients.
  • US Patent no. 5,488,043 also to Sumitomo Chemical Company discloses a method for stabilizing acephate by adding a sodium salt of condensed phosphate and/or a modified synthetic silicic acid to a dry pesticidal formulation.
  • the dry formulation may further include a solid carrier, selected from a list given in the specification of the patent.
  • the dry formulation may further comprise certain other auxiliaries, for example, surface active agents, colouring agents, perfume compounds, and other known stabilizers.
  • US Patent no. 6,335,026 also to Sumitomo Chemical Company discloses stabilized solid pesticidal compositions containing acephate and at least one of a further stabilizer compound selected from the group consisting of boron oxide, metaboric acid, aluminium oxide, and the calcined product of synthetic silicon dioxide.
  • the composition may further comprise certain other auxiliaries, for example, surface active agents, colouring agents, perfume compounds, and other known stabilizers.
  • the stabilized acephate compositions disclosed in the prior art each suffers from certain disadvantages including the increased cost of manufacture, the necessity of further processing steps for certain applications, and the suitability of the compositions for use in certain applications.
  • a stabilized liquid pesticidal formulation suitable for use as an undiluted concentrate stem application pesticide, the formulation comprising a pesticidally effective amount of 0,S-dimethyl acetyiphosphoramidothioate in methyl alcohol.
  • formulation comprises 0,S-dimethyl acetyiphosphoramidothioate at a concentration of between about 100 mg/mL to about 600 mg/mL.
  • the formulation comprises 0,S-dimethyl acetyiphosphoramidothioate at a concentration of between about 250 mg/mL to about 450 mg/mL.
  • the formulation comprises 0,S-dimethyl acetyiphosphoramidothioate at a concentration of between about 300 mg/mL to about 400 mg/mL.
  • the formulation comprises 0,S-dimethyl acetyiphosphoramidothioate at a concentration of about 350 mg/mL.
  • the formulation comprises no further auxiliary agents including surface active agents and stabilizers.
  • a method of treating trees or plants against pests including the step of applying an undiluted concentrate stabilized liquid pesticidal formulation comprising a pesticidally effective amount of 0,S-dimethyl acetylphosphoramidothioate in methyl alcohol directly to the trunk or stem of the tree or plant.
  • more than one application of the undiluted concentrate pesticide formulation is made to the tree or plant.
  • the applications are made at intervals ranging between 7 days and 28 days.
  • the applications are made at intervals ranging between 14 days and 28 days.
  • the applications are made at 21 or 28 day intervals.
  • the formulation comprises 0,S-dimethyl acetylphosphoramidothioate at a concentration of between about 100 mg/mL to about 600 mg/mL.
  • the formulation comprises 0,S-dimethyl acetylphosphoramidothioate at a concentration of between about 250 mg/mL to about 450 mg/mL.
  • the formulation comprises 0,S-dimethyl acetylphosphoramidothioate at a concentration of between about 300 mg/mL to about 400 mg/mL.
  • the formulation comprises 0,S-dimethyl acetylphosphoramidothioate at a concentration of about 350 mg/mL.
  • the plants or trees may be citrus varieties, deciduous fruit including stone fruit and pome fruit, vines, subtropical crops including avocado, mango and nut crops including macadamia and pecans.
  • the pests may be selected from the group consisting of Aphid (Toxoptera citricidus), Psylla ⁇ Trioza erytreae), Thrip (Scirtothrips aurantii), Orange dog (Papillio spp.), and bud mite (Aceria sheldoni).
  • the use of the pesticide formulation is not limited to the aforementioned species. It is envisaged for use against not only those species, but may also include all representatives of that particular group of insect, for example: fam: Psyllidae, (i) Genus: Diaphorina, Species D. citri ; (ii) Genus: Trioza, Species: T erytreae; and
  • Genus Aphis
  • Species gossypii
  • Genus Toxoptera
  • T. citricidus Genus: T. citricidus
  • the undiluted concentrate pesticide formulation is applied at an application rate of between about 0.1 mL per 10 mm trunk or stem diameter to 25 mL per 150 mm trunk or stem diameter.
  • the undiluted concentrate pesticide formulation is applied at an application rate of between about 0.1 mL per 10 mm trunk or stem diameter to 1 mL per 50 mm mm trunk or stem diameter.
  • residue analysis results for 0,S-dimethyl phosphoramidothioate is below 0.05 ppm after 7 days, 14 days, 21 days, and 28 days after application.
  • residue analysis results for 0,S- dimethyl phosphoramidothioate is below 0.01 ppm after 7 days, 14 days, 21 days, and 28 days after application.
  • this invention relates to a stabilized liquid pesticide formulation including O.S-dimethyl acetylphosphoramidothioate, commonly known as acephate, and the use of the undiluted formulation in a method of crop treatment, in particular, but not exclusively, in a method of treating citrus crops.
  • the stabilized liquid pesticide formulation comprises the active ingredient 0,S-dimethyI acetylphosphoramidothioate (acephate) at a concentration of between about 100 mg/mL to about 600 mg/mL, preferably at a concentration of between about 250 mg/mL to about 450 mg/mL, more preferably at a concentration of between about 300 mg/mL to about 400 mg/mL, and most preferably at a concentration of about 350 mg/mL of methyl alcohol (methanol).
  • acephate acephate
  • the method of the present invention for treating trees or plants against pests includes the step of applying an undiluted concentrate stabilized liquid pesticide formulation comprising the active ingredient 0,S- dimethyl acetylphosphoramidothioate (acephate) in methyl alcohol directly to the trunk or stem of a tree or plant.
  • an undiluted concentrate stabilized liquid pesticide formulation comprising the active ingredient 0,S- dimethyl acetylphosphoramidothioate (acephate) in methyl alcohol directly to the trunk or stem of a tree or plant.
  • the concentration of 0,S-dimethyl acetylphosphoramidothioate (acephate) in methyl alcohol is between about 100 mg/mL to about 600 mg/mL, preferably at a concentration of between about 250 mg/mL to about 450 mg/mL, more preferably at a concentration of between about 300 mg/mL to about 400 mg/mL, and most preferably at a concentration of about 350 mg/mL of methyl alcohol (methanol).
  • the stabilized liquid pesticide formulation of the present invention is a systemic insecticide formulated as an undiluted concentrate stem paint-on or stem spray-on treatment, for the control of insect pests.
  • the insect pests positively shown to be controlled by stabilized liquid pesticide formulation of the present invention include: Orange dog (Papillio spp.), Citrus aphid (Toxoptera citricidus), Citrus thrip (Scirtothrips aurantii), Citrus bud mite (/Acer/a sheldoni) and Citrus psylla (Trioza erytreae).
  • the use of the pesticide formulation is not limited to the aforementioned species. It is envisaged for use against not only those species, but may also include all representatives of that particular group of insect, for example: fern: Psyllidae, (i) Genus: Diaphorina, Species D. citri ; (ii) Genus: Trioza, Species: T erytreae; and
  • Genus Aphis
  • Species gossypii
  • Genus Toxoptera
  • T. citricidus Genus: T. citricidus
  • a stabilized liquid pesticide formulation according to the present invention comprising 350 g/L of the active ingredient 0,S-dimethyl acetylphosphoramidothioate in methyl alcohol, was used in the trials shown below.
  • Citrimet 500 AL (Reg. No. L4361 ) which is registered for use in inter alia citrus and mango crops.
  • Citrimet 500 AL comprises the undesirable active ingredient methamidophos.
  • UTC refers to an untreated control
  • UTC infested flushes refers to the percentage of insect pest infested flushes, giving an indication of the level of infestation and confirming that the levels of pest infestation are significant.
  • Spectra Stem 350 AL and SS refers to the pesticide formulation according to the present invention.
  • Figure 1 shows the rate of uptake in citrus through its efficacy against Orange dog (PapHlio spp.) and Citrus aphid (Toxoptera citricidus).
  • the rate of uptake of the pesticide formulation as a horizontal band stem treatment in citrus occurred between 48 and 72 hours following the application, as determined by mortality in orange dog larvae.
  • Figure 2 shows the efficacy of the pesticide formulation against citrus aphid (Toxoptera citricidus).
  • the efficacy of the pesticide formulation with horizontal band application and vertical spray application compared well with the standard Citrimet 500 AL horizontal band application on citrus aphid.
  • Figure 2 further shows that the difference in efficacy on citrus aphid was achieved irrespective of the application method used (vertical spray application or horizontal band application) in the 4 trails conducted.
  • Figure 3 shows the efficacy of the pesticide formulation against citrus thrip (Scirtothrips aurantii). It is clear from Figure 3 that the efficacy of the pesticide formulation with vertical spray, vertical band, and horizontal band compares well with the standard Citrimet 500 AL horizontal band application on citrus thrip. Figure 3 further shows that the difference in efficacy on citrus thrip was achieved irrespective of the application method used in the 7 trials conducted.
  • Figure 4 shows the efficacy of the pesticide formulation against citrus bud mite (Aceria sheldoni). The efficacy of the pesticide formulation with vertical spray, vertical band, and horizontal band compares well with the standard Citrimet 500 AL horizontal band application on citrus bud mite. Again, similar to the results obtained for citrus thrip and citrus aphid, Figure 4 shows that there was no application dependent statistical difference in efficacy on citrus bud mite for the various application methods tested in the 4 trials conducted.
  • Figure 5 shows the efficacy of the pesticide formulation against citrus psylla (Trioza erytreae).
  • the efficacy of the pesticide formulation with vertical spray, vertical band, and horizontal band compares well with the standard Citrimet 500 AL horizontal band application on citrus psylla.
  • Figure 5 shows that there was no application dependent statistical difference in efficacy on citrus bud mite for the various application methods tested in the 6 trials conducted.
  • Crop safety of the products used as stem treatments on tree crops is largely dependent on the formulation, as these treatments are usually undiluted applications directly onto the bark of the tree trunk.
  • Instances have been cited in the literature of incompatible formulations that have been used as undiluted stem applications in the past that have resulted in severe phytotoxicity.
  • Cases have been documented where insecticide formulations containing similar active ingredients, but registered for use as diluted spray applications on other types of agricultural crops, have caused widespread phytotoxicity in the form of bark split, seedling mortality and branch die back when applied as undiluted stem applications in citrus.
  • certain rootstocks used on commercial varieties of citrus have shown incompatibility to certain insecticide formulations used as stem applications.
  • Trial results were obtained for the pesticide formulation according to the present invention at between 0.5 - 3 times a proposed recommended rate, to ascertain any phytotoxicity.
  • the results obtained were for tests conducted on 6 citrus varieties: 4 orange, and 2 lemon, with the sample set including the common navel (2), soft citrus (2) and Turkey citrus varieties, and on 4 of the most commonly used rootstocks.
  • the parameters used to determine phytotoxicity were those typically used in such tests and included: bark split, branch discoloration, branch die back. No visual symptoms of phytotoxicity were observed in the treated trees from the single, double (8 trials) or triple dosage rates (2 trials) applied, supporting the position of an absence of any subsequent phytotoxicity from the treatment of the trees with the pesticide formulation of the present invention.
  • the pesticide formulation of the present invention used as an undiluted stem treatment formulation exhibited consistently high levels of efficacy on all target insect species, with good commercial control, and comparable efficacy obtained to that recorded for the commercially available and registered product Citrimet 500 AL.
  • the pesticide formulation of the present invention applied in the undiluted form was shown to be safe for use on both oranges and lemons on the widely grown and common varieties of citrus when applied at the tested 0.5 - 3 times the recommended dosage rates, with no phytotoxicity noted during the evaluations.
  • Residues in citrus fruit were tested for the Minneola, Turkey and Lemon cultivars. Residue sampling methods were conducted according to Good Agricultural Practice (GAP), where representative fruit samples were collected from the treated trees and placed directly into impermeable bags, avoiding any physical contact or contamination, at the specified intervals following application (0 days; 7 days; 14 days; 21 days and 28 days after application).
  • GAP Good Agricultural Practice
  • the impermeable plastic bags specifically used for the storage of residue samples) containing the fruit residue samples were then sealed and placed in frozen storage within two hours of collection.
  • the frozen samples were then delivered to the accredited laboratory (South African Bureau of Standards) by suitably qualified personnel, within 2 months of collection, for subsequent residue analysis according to the methods as described.
  • FIG. 7 shows the results of tests conducted at the University of Florida to determine the level and residual activity of a stem application of a pesticide formulation according to the present invention ("Spectra Stem") on young non- bearing citrus plants on the Asian Citrus Psylla, Diaphorina citri.
  • Spectra Stem a pesticide formulation according to the present invention
  • CropA ariety Sweet Orange cv "Hamlin"
  • a 20 cm diameter paper bowl was placed around the trunks for collection of the psyllids.
  • a fabric cover was placed over the plants extending below the base of the bowl.
  • Mortality was evaluated at 3, 7, 14, 21 , 28, 35 and 46 days post-treatment. At each evaluation period, the covers were removed from the plants and the number of live and dead psyllids counted and removed. Another set of 50 psyllids were then introduced.
  • the formulation according to the present invention is effective as undiluted concentrate stem application pesticide against Asian Citrus Psylla, Diaphorina citri.
  • the above description of some of the illustrative embodiments of the invention is to indicate how the invention can be made and carried out. Those of ordinary skill in the art will know that various details may be modified thereby arriving at further embodiments, but that many of these embodiments will remain within the scope of the invention.
  • the stabilized liquid pesticide formulation described may be altered by including minor auxiliary compounds such perfumes, colouring agents, alternatively the formulation may be altered by including a further pesticidal agent.

Abstract

L'invention concerne une composition pesticide liquide stabilisée qui est appropriée à une utilisation en tant que pesticide concentré non dilué à appliquer sur les tiges. Cette composition comprend une quantité efficace sur le plan pesticide d'acétylphosphoramidothioate de O,S-diméthyle dans de l'alcool méthylique. L'invention concerne également un procédé permettant de traiter des arbres ou des plantes contre les organismes nuisibles et comprenant une étape consistant à appliquer une composition pesticide liquide concentrée, non diluée et stabilisée comprenant une quantité efficace sur le plan pesticide d'acétylphosphoramidothioate de O,S-diméthyle dans de l'alcool méthylique directement sur le tronc ou la tige de l'arbre ou de la plante.
PCT/IB2015/058862 2014-12-03 2015-11-17 Composition pesticide liquide stabilisée à base d'acéphate WO2016087971A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ZA2014/08874 2014-12-03
ZA201408874 2014-12-03

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WO2016087971A1 true WO2016087971A1 (fr) 2016-06-09

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114901068A (zh) * 2019-11-18 2022-08-12 海怡弥私人有限公司 受控释放的树干植入物制剂和包含该植入物制剂的树干植入物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5698540A (en) * 1994-02-10 1997-12-16 Sumitomo Chemical Company, Limited Stabilized pesticidal composition containing acephate
WO2001005225A1 (fr) * 1999-07-19 2001-01-25 Monsanto Technology Llc Compositions aqueuses concentrees de pesticide moins nocives pour les yeux et la peau
WO2014019983A1 (fr) * 2012-07-31 2014-02-06 Bayer Cropscience Ag Compositions contenant un mélange terpénique pesticide et un insecticide
US20140256687A1 (en) * 2011-06-29 2014-09-11 Nihon Nohyaku Co., Ltd. Agricultural and Horticultural Insecticide Composition and Method for Using the Same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5698540A (en) * 1994-02-10 1997-12-16 Sumitomo Chemical Company, Limited Stabilized pesticidal composition containing acephate
WO2001005225A1 (fr) * 1999-07-19 2001-01-25 Monsanto Technology Llc Compositions aqueuses concentrees de pesticide moins nocives pour les yeux et la peau
US20140256687A1 (en) * 2011-06-29 2014-09-11 Nihon Nohyaku Co., Ltd. Agricultural and Horticultural Insecticide Composition and Method for Using the Same
WO2014019983A1 (fr) * 2012-07-31 2014-02-06 Bayer Cropscience Ag Compositions contenant un mélange terpénique pesticide et un insecticide

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114901068A (zh) * 2019-11-18 2022-08-12 海怡弥私人有限公司 受控释放的树干植入物制剂和包含该植入物制剂的树干植入物

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