WO2020174498A1 - Composition insecticide synergique comprenant un composé d'avermectine - Google Patents

Composition insecticide synergique comprenant un composé d'avermectine Download PDF

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Publication number
WO2020174498A1
WO2020174498A1 PCT/IN2020/050180 IN2020050180W WO2020174498A1 WO 2020174498 A1 WO2020174498 A1 WO 2020174498A1 IN 2020050180 W IN2020050180 W IN 2020050180W WO 2020174498 A1 WO2020174498 A1 WO 2020174498A1
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WO
WIPO (PCT)
Prior art keywords
insecticidal composition
synergistic insecticidal
composition
present
emulsion
Prior art date
Application number
PCT/IN2020/050180
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English (en)
Inventor
Parikshit MUNDHRA
Jitendra Mohan
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Willowood Chemicals Private 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
Publication date
Application filed by Willowood Chemicals Private Limited filed Critical Willowood Chemicals Private Limited
Priority to BR112021017020A priority Critical patent/BR112021017020A2/pt
Priority to MX2021010382A priority patent/MX2021010382A/es
Publication of WO2020174498A1 publication Critical patent/WO2020174498A1/fr
Priority to ZA2021/06341A priority patent/ZA202106341B/en

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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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • the present invention relates to a synergistic insecticidal composition intended for protecting plants, crops or seeds against insect damages.
  • the present invention relates to a novel synergistic insecticidal composition comprising emamectin benzoate, deltamethrin and lambda-cyhalothrin; formulation comprising the synergistic composition and methods of preparation of said formulation.
  • PCT publication no. WO 00/02453 relates to a pesticidal composition comprising emamectin and at least one other pesticide compound selected from a list of 185 compounds.
  • the listed compounds are: Aldicarb; Azinphos-methyl; Benfuracarb; Bifenthrin; Buprofezin; Carbofuran; Carbosulfan; Cartap; Chlorfluazuron; Chlorpyrifos; Cyfluthrin; Lambda-cy-halothrin; Alpha- cypermethrin; zeta-Cypermethrin; Deltamethrin; Diflubenzuron; Endosulfan; Ethiofencarb; Fenitrothion; Fenobucarb; Fenvalerate; Formothion; Methiocarb; Heptenophos; Imidacloprid; Isoprocarb; Methamidophos; Methomyl; Mevinphos; Parathion; Parathion-methyl; Phosalone; Pirimi- carb; Propoxur; Teflubenzuron; Terbufos; Triazamate; Fenobucarb; Tebufen
  • Chinese patent application CN1524420A relates to an insecticidal compound containing emamectin and at least one pyrethroid compound selected from permethrin, cypermethrin, beta-cypermethrin, cyhalothrin, deltamethrin, bifenthrin, fenvalerate, esfenvalerate, fenpropathrin, b fenpropathrin, etofenprox, flucythrinate, fluvalinate, tefluthrin, tralomethrin and cyfluthrin.
  • pyrethroid compound selected from permethrin, cypermethrin, beta-cypermethrin, cyhalothrin, deltamethrin, bifenthrin, fenvalerate, esfenvalerate, fenpropathrin, b fenpropathrin,
  • composition comprising emamectin benzoate, deltamethrin and lambda-cyhalothrin act synergistically and are suitable for controlling animal pests. Owing to this synergism, markedly lower amounts of active compound can be used, i.e. the activity of the mixture is greater than the activity of the individual components.
  • the present invention provides a synergistic insecticidal composition
  • a synergistic insecticidal composition comprising emamectin benzoate, deltamethrin and lambda-cyhalothrin wherein emamectin benzoate is present in an amount in the range from about 0.1 to 3% w/w, deltamethrin in an amount in the range from about 0.1 to 3% w/w and lambda-cyhalothrin in an amount in the range from about 0.1 to 3% w/w.
  • emamectin benzoate is present in an amount 1.1 % w/w
  • deltamethrin is present in an amount 1.5% w/w
  • lambda-cyhalothrin is present in an amount 1.5% w/w.
  • the synergistic insecticidal composition is formulated as Capsule suspension (CS), Dispersible concentrate (DC), Dustable powder (DP), Powder for dry seed treatment (DS), Emulsifiable concentrate (EC), Emulsifiable granule (EG), Emulsion water-in-oil (EO), Emulsifiable powder (EP), Emulsion for seed treatment (ES), Emulsion oil-in-water (EW), Flowable concentrate for seed treatment (FS), Granules (GR), Micro-emulsion (ME), Oil-dispersion (OD), Oil miscible flowable concentrate (OF), Oil miscible liquid (OL), Oil dispersible powder (OP), Suspension concentrate (SC), Suspension concentrate for direct application (SD), Suspo-emulsion (SE), Water soluble granule (SG), Soluble concentrate (SL), Spreading oil (SO), Water soluble powder (SP), Water soluble tablet (ST), Ultra-low volume (ULV) suspension, Tablet (TB), Ultra-
  • the synergistic insecticidal composition is formulated as micro-emulsion.
  • the synergistic composition further comprises an excipient selected from the group comprising emulsifier, acidifier and solvents.
  • the emulsifier comprises 5 to 20% w/w of one or more non-ionic emulsifying agents; and 2 to 10% w/w of one or more anionic emulsifying agents.
  • the non-ionic emulsifying agent is selected from the group comprising styrenated phenol ethoxylate and castor oil ethoxylate.
  • the anionic emulsifying agent is selected from the group comprising phosphate ester and calcium dodecylbenzene sulfonate.
  • the acidifier is selected from the group comprising citric acid, fumaric acid, trifluoroacetic acid and combinations thereof, and present in an amount in the range from 0.1 to 1% w/w.
  • the solvent is selected from the group comprising C-9, xylene, toluene, 2-ethyl hexanol, dimethyl sulfoxide, N-methyl-2-pyrrolidone, cyclohexanone and combinations thereof.
  • active ingredient (A.I.) or“active agent” used herein refers to that component of the composition responsible for control of insect-pests.
  • the expressions“SL formulation”,“SC formulation”“WDG or WG formulation”“GR formulation”,“DF formulation”,“CG formulation”,“EC formulation”,“EW formulation”,“ME formulation”,“WP formulation” are the international denominations adopted by the FAO (Food and Agricultural Organization of the United Nations) to designate “soluble liquid”, “aqueous suspension concentrate”,“water dispersible granules”,“granular”,“dry flowable”, “capsulated granules”, “emulsion concentrate”, “emulsion”, “micro-emulsion” and“wettable powder” respectively.
  • a synergistic insecticidal composition comprising emamectin benzoate, deltamethrin and lambda-cyhalothrin.
  • the present invention provides a synergistic insecticidal composition comprising emamectin benzoate in an amount in the range from about 0.1 to 3% w/w, deltamethrin in an amount in the range from about 0.1 to 3% w/w and lambda-cyhalothrin in an amount in the range from about 0.1 to 3% w/w.
  • Emamectin benzoate, deltamethrin and lamba-cyhalothrin are prepared by methods known in the art or are commercially obtained.
  • Emamectin benzoate (IUPAC name: A mixture containing 90% of (10£,14£,16£)-(lR,4S,5'S,6S,6'R,8R,12S,13S,20R,21R,24S)-6'-[(S)- «c-butyl]- 21 ,24 -dihydroxy-5 ', 11,13 ,22-tetramethyl-2 -oxo-(3 ,7,19- trioxatetracyclo[15.6.1.1 4 ’ 8 .0 20 ’ 24 ]pentacosa-10,14,16,22-tetraene-6-spiro-2'-(5',6'- dihydro-2 '//-pyran)-12-yl 2,6-dideoxy-3-0-methyl-4-0-(2,4,6-
  • Deltamethrin (IUPAC name: (S)-a-cyano-3-phenoxybenzyl (lR,3R)-3-(2,2- dibromovinyl)-2,2-dimethylcyclopropanecarboxylate; Roth: (S)-a-cyano-3- phenoxybenzyl (lR)-cis-3-(2,2-dibromovinyl)-2,2- dimethylcyclopropanecarboxylate) belongs to pyrethroid group of insecticides. It is represented by the following structure:
  • Lambda-cyhalothrin (IUPAC name: Mixture of (R)-a-cyano-3-phenoxybenzyl (lS,3S)-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2- dimethylcyclopropanecarboxylate and (S)-a-cyano-3-phenoxybenzyl (lR,3R)-3- [(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate;
  • the synergistic insecticidal composition comprises emamectin benzoate in an amount 1.1 % w/w, deltamethrin in an amount 1.5% w/w and lambda-cyhalothrin in an amount 1.5% w/w.
  • composition of the present invention can be converted into the customary formulations, such as Capsule suspension (CS), Dispersible concentrate (DC), Dustable powder (DP), Powder for dry seed treatment (DS), Emulsifiable concentrate (EC), Emulsifiable granule (EG), Emulsion water-in-oil (EO), Emulsifiable powder (EP), Emulsion for seed treatment (ES), Emulsion oil-in- water (EW), Flowable concentrate for seed treatment (FS), Granules (GR), Micro emulsion (ME), Oil-dispersion (OD), Oil miscible flowable concentrate (OF), Oil miscible liquid (OL), Oil dispersible powder (OP), Suspension concentrate (SC), Suspension concentrate for direct application (SD), Suspo-emulsion (SE), Water soluble granule (SG), Soluble concentrate (SL), Spreading oil (SO), Water soluble powder (SP), Water soluble tablet (ST), Ultra-low volume (ULV) suspension, Tablet (TB), Ultra-low
  • composition of the present invention further comprises an excipient.
  • the synergistic insecticidal composition is formulated as micro -emulsion (ME).
  • ME micro -emulsion
  • the excipients that are used to formulate a micro emulsion include but not limited to emulsifier, acidifier and solvents.
  • Micro-emulsions are regarded as one of the most promising pesticide formulations.
  • formulation of pesticide micro-emulsions is not simple. Obtaining efficient, scientific and inexpensive formulation is challenging.
  • Micro-emulsion is defined as a solution of a pesticide with emulsifying agents in a water insoluble organic solvent which will form a solution/emulsion when added to water.
  • Micro-emulsions are thermodynamically stable water-based systems containing a water-insoluble component. This means that within a given set of conditions, the oil phase is stable and will never separate out.
  • micro emulsions are composed of extremely tiny particles (similar to micelles) that can be as small as 0.01 micron. This makes the diluted product transparent because light scattering is reduced. By comparison, most coarse emulsions can have average particle sizes in the order of 1 to 5 microns.
  • Micro-emulsion formulations offer a number of practical advantages, one of the most important being that they typically remain homogeneous without agitation for long periods of time. In this respect, to the agricultural technician or other user, a micro-emulsion formulation can be handled with the same ease and convenience as a simple aqueous solution.
  • An emulsifier is a substance that stabilizes an emulsion by increasing its kinetic stability.
  • the emulsifiers can be anionic or non-ionic in character.
  • a combination of non- ionic and anionic emulsifying agents is used in the composition of the present invention.
  • One or more non-ionic emulsifying agents and one or more anionic emulsifying agents may be used in the composition of the present invention.
  • the emulsifier comprises 5 to 20% w/w of one or more non-ionic emulsifying agents; and 2 to 10% w/w of one or more anionic emulsifying agents.
  • Non limiting examples of non-ionic emulsifying agent that can be employed in present invention are styrenated phenol ethoxylate and castor oil ethoxylate.
  • Non limiting examples of anionic emulsifying agent that can be employed in present invention are phosphate ester and calcium dodecylbenzene sulfonate.
  • Commercially available emulsifiers such as UNITOX-30 and UNITOX-50 may be used in the composition of the present invention.
  • An acidifier is added to the composition of the present invention to enhance the stability of the formulation and also for standardization of pH.
  • the pH of the composition of the present invention formulated as ME is maintained in the range from 2 to 6.
  • Non limiting examples of acidifier that can be employed in present invention are citric acid, fumaric acid, trifluoroacetic acid and is present in an amount in the range from 1 to 2% w/w.
  • Suitable solvents useful in accordance with the invention are C9 aromatic solvents, xylene, toluene, 2-ethyl hexanol, dimethyl sulfoxide (DMSO), cyclohexanone, N-methylpyrrolidone (NMP), butanol and combinations thereof.
  • DMSO dimethyl sulfoxide
  • NMP N-methylpyrrolidone
  • a combination of two or more solvents are used in the composition of the present invention.
  • the synergistic composition of the present invention is used to control wide variety of insects, by way of example, Helicoverpa armigera, pink bollworm and Spodoptera litura, lepidoptera, coleoptera, heteroptera, homoptera, thysanoptera, acrididae, locusts, aphids, Colorado beetles, thrips, jassids and whitefly in vegetables, brassicas, fruit, maize, tea, grapes, cotton, cereals, citrus, oilseed rape, soybeans and other crops.
  • the present invention provides a process for the preparation of micro-emulsion formulation comprising the synergistic composition.
  • the formulation may be prepared by any method known in the art.
  • composition of the present invention is synergetic in nature.
  • the synergetic composition of the present invention is more effective than their individual counterparts or when two actives are taken together.
  • the synergetic composition of the present invention also makes it possible to use markedly smaller quantities of the active ingredients as compared to their individual counterparts.
  • composition of the present invention is effective in controlling wide spectrum of insect pests, delays the emergence of the resistant strains of the insect -pests and achieves effective and economic control of undesired insect-pests.
  • the composition of the present invention is relatively safer to human beings, animals and is non-phytotoxic.
  • the synergistic composition of the present invention provides a number of other advantages-
  • the synergistic insecticidal composition of the present invention comprising emamectin benzoate, deltamethrin and lambda-cyhalothrin in the form of micro- emulsion is provided in Table 1.
  • the unit of each component of the composition are expressed in“% w/w” i.e. the percentage by weight, relative to the weight of the total solution or composition.
  • Table 1 Synergistic insecticidal composition comprising emamectin benzoate, deltamethrin and lambda-cyhalothrin in the form of micro- emulsion (ME)
  • Table 2 provides quantities of active ingredients and raw material charged to prepare the synergistic composition of the present invention in ME form.
  • the active ingredients are in technical grade.
  • the entries for active ingredients, emamectin benzoate, deltamethrin and lambda-cyhalothrin in table 2 varies from that of table 1 , as the entries in table 1 are for 100% pure compounds whereas the entries in Table 2 are for technical ones with certain percentage of impurities.
  • emamectin benzoate 1.1 % w/w, deltamethrin 1.5% w/w and lambda- cyhalothrin 1.5% w/w of 100% purity of Table 1 corresponds to emamectin benzoate 1.16 g of 95% purity, deltamethrin 1.54 g of 98% purity and lambda- cyhalothrin 1.57 g of 96% purity of Table 2.
  • Example 1 Process of preparing synergistic insecticidal composition comprising emamectin benzoate, deltamethrin and lambda-cyhalothrin in ME form
  • Trials were performed in different agro climatic zones of the country to evaluate the biological efficacy of the synergistic insecticidal composition of present invention (Tl) and reference products (T2 - T7) against borers ( Helicoverpa armigera, Pink Bollworm and Spodoptera liturd) and sucking pests (Aphids, Jassids and Whitefly) of cotton.
  • Table 3 provides treatment details of insecticidal compositions for evaluation of bio-efficacy in cotton against borer complex and sucking pests complex. The evaluation was performed by comparing the synergistic insecticidal composition of the present invention (emamectin benzoate 1.1% + deltamethrin 1.5% + lambda-cyhalothrin 1.5% ME) against the reference products, such as, emamectin benzoate and deltamethrin; deltamethrin and lambda-cyhalothrin; emamectin benzoate and lambda-cyhalothrin; solo formulations of emamectin benzoate, deltamethrin and lambda-cyhalothrin.
  • the synergistic insecticidal composition of the present invention emamectin benzoate 1.1% + deltamethrin 1.5% + lambda-cyhalothrin 1.5% ME
  • the reference products such as,
  • the experiment was laid out in Randomized Block Design (RBD) with three replications.
  • the plot size was 100 sq. mts. All the recommended agronomic practices were followed throughout the cropping period.
  • the various insecticidal compositions as per Table 3 were sprayed on cotton crop to evaluate the control of borers ( Helicoverpa armigera, Pink Bollworm and Spodoptera litura ) and sucking Pests (Aphids, Jassids and Whitefly). Hollow cone nozzle was used for spraying.
  • the spray volume used was 500 litres per hectare. Based on various doses, weighed quantity of test products were dissolved in 5 litres of water/treatment and sprayed uniformly twice at an interval of 10 days.
  • synergistic effect exists whenever the action of an active ingredient combination is greater than the sum of the actions of the individual components. Synergism was calculated by using Colby’s method, Weeds, vol 15 No. l(Jan 1967), pp 20-2. The synergistic action expected for a given combination of three active components can be calculated as follows:
  • E represents expected percentage of insecticidal control for the combination of the three insecticides at defined doses (for example equal to x, y and z respectively)
  • X is the percentage of insecticidal control observed by the compound (I) at a defined dose (equal to x)
  • Y is the percentage of insecticidal control observed by the compound (II) at a defined dose (equal to y)
  • Z is the percentage of insecticidal control observed by the compound (III) at a defined dose (equal to z).
  • the synergistic insecticidal composition of the present invention gave good control of insects and better economics to farmers as compared to the reference products. Further, the use of the synergistic insecticidal composition resulted in better crop condition, i.e. fresh green leaves and did not produce any phytotoxic symptoms on the plants.

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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 une composition insecticide synergique comprenant du benzoate d'emamectine, de la deltaméthrine et de la lambda-cyhalothrine. La composition de la présente invention réduit les taux d'application de chacun de ces principes actifs, réduit le coût de traitement pour les agriculteurs et n'est pas phytotoxique.
PCT/IN2020/050180 2019-02-28 2020-02-27 Composition insecticide synergique comprenant un composé d'avermectine WO2020174498A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
BR112021017020A BR112021017020A2 (pt) 2019-02-28 2020-02-27 Composição insecticida sinergética que compreende composto de avermectina
MX2021010382A MX2021010382A (es) 2019-02-28 2020-02-27 Composicion insecticida sinergica que comprende un compuesto de avermectina.
ZA2021/06341A ZA202106341B (en) 2019-02-28 2021-08-31 Synergistic insecticidal composition comprising avermectin compound

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN201911007935 2019-02-28
IN201911007935 2019-02-28

Publications (1)

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WO2020174498A1 true WO2020174498A1 (fr) 2020-09-03

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PCT/IN2020/050180 WO2020174498A1 (fr) 2019-02-28 2020-02-27 Composition insecticide synergique comprenant un composé d'avermectine

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BR (1) BR112021017020A2 (fr)
MX (1) MX2021010382A (fr)
WO (1) WO2020174498A1 (fr)
ZA (1) ZA202106341B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023095100A1 (fr) * 2021-11-29 2023-06-01 Rallis India Limited Composition insecticide, formulations et procédé de préparation associé

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1524420A (zh) * 2003-02-24 2004-09-01 李建中 一种含有甲胺基阿维菌素和拟除虫菊酯化合物的杀虫组合物
WO2010095151A2 (fr) * 2009-02-20 2010-08-26 Deepak Pranjivandas Shah Composition granulaire hydro-dispersible

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1524420A (zh) * 2003-02-24 2004-09-01 李建中 一种含有甲胺基阿维菌素和拟除虫菊酯化合物的杀虫组合物
WO2010095151A2 (fr) * 2009-02-20 2010-08-26 Deepak Pranjivandas Shah Composition granulaire hydro-dispersible

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023095100A1 (fr) * 2021-11-29 2023-06-01 Rallis India Limited Composition insecticide, formulations et procédé de préparation associé

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BR112021017020A2 (pt) 2022-01-11
MX2021010382A (es) 2022-01-18
ZA202106341B (en) 2022-07-27

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