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WO2018233869A1 - Formulations insecticides améliorées - Google Patents

Formulations insecticides améliorées Download PDF

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Publication number
WO2018233869A1
WO2018233869A1 PCT/EP2018/000310 EP2018000310W WO2018233869A1 WO 2018233869 A1 WO2018233869 A1 WO 2018233869A1 EP 2018000310 W EP2018000310 W EP 2018000310W WO 2018233869 A1 WO2018233869 A1 WO 2018233869A1
Authority
WO
WIPO (PCT)
Prior art keywords
acids
acid
insecticide formulation
formulation according
insecticide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2018/000310
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English (en)
Inventor
Graham Moores
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
APRESLABS Ltd
Original Assignee
APRESLABS 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
Application filed by APRESLABS Ltd filed Critical APRESLABS Ltd
Priority to EP18752684.3A priority Critical patent/EP3641546A1/fr
Publication of WO2018233869A1 publication Critical patent/WO2018233869A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof

Definitions

  • the present invention relates to improved insecticide formulations and their use.
  • the pyrethrum family has been known for many years as providing useful insecticides.
  • Naturally occurring pyrethroids known as pyrethrins can be obtained from Chrysanthemum plants and other daisies.
  • synthetic pyrethroids There are also a wide range of synthetic pyrethroids.
  • the synthetic pyrethroids are more potent insecticides than the naturally occurring pyrethrins.
  • they tend to be more stable particularly on exposure to ultra-violet light. This combination of properties can have the damaging effect that after application to a crop because of infestation of a particular insect the synthetic pyrethroid may linger around and can be subsequently detrimental to beneficial insects such as bees.
  • Natural pyrethrins are more readily degraded upon exposure to ultra violet light. It would therefore be useful if the insecticidal potency of a natural pyrethrin could be increased to be comparable or superior to that of the synthetic pyrethroids.
  • the formulation it provides comprises an aqueous solution of pH 7.5 to 8.8 containing 30 to 50 parts of an aqueous solution comprising 50 percent by weight of a mixture of monocarboxylic acids and their alkali metal salts, the acid mixture comprising at least 70% oleic acid and its alkali metal salts, together with between 1 .0 and 2.0 parts of a pyrethrum extract comprising about 20% of a mixture of insecticidally active substances selected from pyrethrum I, pyrethrum II, cinerin I, cinerin II, jasmolin I and jasmolin II; 3 to 20 parts of a low molecular weight 2-6 carbon atoms alcohol solvent for the pyrethrum and an antioxidant.
  • the salts are produced by reaction with potassium hydroxide and the pH is controlled with hydrochloric acid and accordingly the formulations are not 100% organic materials and are slightly alkaline.
  • the material is diluted with water so that on application to plants it provides 0.5 wt % of the acid mixture and 0.005 wt % of the pyrethrum extract.
  • the ratio of the acids and their salts to the pyrethrum is of the order of from 80: 1 to 100: 1.
  • United States Patent 5,047,424 discloses that the compositions of US Patent 4,904,645 (resulting from application serial no. 148961 ) are relatively expensive and are susceptible to degradation during storage or use because of the presence of pyrethrums.
  • the present invention therefore provides an insecticide formulation comprising
  • an unsaturated fatty acid or fatty acid mixture containing on average from 16 to 24 carbon atoms and/or their alkali metal salts wherein the unsaturated fatty acids are derived from natural sources
  • the ratio of the weight of unsaturated fatty acid and/or alkali metal salt thereof to the weight of natural pyrethrin is from 3: 1 to 20: 1 and the pH of the formulation is below 7.
  • the unsaturated acids and their derivatives which are used in this invention are mono- and polyunsaturated carboxylic acids having an average of 16 to 24 carbon atoms, or their alkali metal salts. It is preferred to use mixtures of unsaturated acids having an average of 16 to 24 carbon atoms.
  • C16 to C18 average mono- or polyunsaturated acids or their alkali metal salts more preferably we use the acids to provide a formulation having a pH below 7 typically in the range 3 to 7 more typically 5 to 7.
  • the preferred C16 to C24 acids and their mixtures are derived from the production of naturally occurring products such as sunflower oil, palm oil, olive oil, maize oil, canola oil, and other vegetable oils, soya chestnuts and horse chestnuts.
  • the acids may be obtained by extraction and they typically comprise mixtures of mono- or poly- unsaturated acids and where mixtures are used the average number of carbon atoms in the acid mixture should be in the C16 to C24 range.
  • the ratio of the weight of the unsaturated fatty acid or fatty acid mixture or derivative thereof to the weight of pyrethrin is from 3: 1 to 10: 1 more preferably from 3: 1 to 8:1.
  • the C16 to C24 average mono- and polyunsaturated acids used in the invention are typically linear C16 to C24 mono- and polyunsaturated acids and thus have the formula RCOOH wherein R is a linear mono- or polyunsaturated hydrocarbon radical having from 16 to 24 carbons.
  • the G16 to C24 mono- and polyunsaturated acids may be selected from one or more of palmitoleic acid (C16: 1 ) sapienic acid (C16: 1 ), a-linolenic acid (C18:3), stearidonic acid (C18:4), eicosapentaenoic acid (C20:5), docosahexaenoic acid (C22:6), linoleic acid (C18:2), ⁇ -linolenic acid (C18:3), dihomo-Y-linolenic acid (C20:3), arachidonic acid (C20:4), adrenic acid (C22:4), palmitoleic acid (C16: 1 ), vaccenic acid (C18: 1 ), paullinic acid (C20: 1 ), oleic acid (C18: 1 ), elaidic acid (Ctrans-18: 1 ), gondoic acid (C20: 1 ),
  • CM:N fatty (where M and N are integers), as used herein, means that the fatty acid comprises M carbon atoms and N double bonds.
  • the N double bonds may be at any position (cis or trans configuration), although two double bonds are not usually adjacent (i.e. bonded to the same carbon atom).
  • C18:0 (or simply C18) covers only octadecanoic acid (stearic acid) and C18: 1 includes all fatty acids having 18 carbons and one double bond, such as oleic acid ((Z)-octadec-9-enoic acid), vaccenic acid ((E)-octadec-l 1 -enoic acid).
  • an alkali metal salt of an acid is typically a lithium, sodium, potassium or rubidium salt.
  • the preferred C16 to C24 mono- and polyunsaturated acid mixture is preferably predominantly oleic acid, together with linoleic acid optionally with minor amounts of other acids and/or alkali metal salts thereof.
  • Aesculus hippocastanum which is known to contain typically 350 g / Kg oleic and linoleic acids (Zalatonov et al).
  • Other preferred sources are the nut (acorn) of the oak tree (Genus Quercus) and ground coffee beans (the seed of the coffee plant).
  • By-products of olive oil production are another preferred source.
  • the acids may be obtained from triglycerides derived from the natural products.
  • the triglycerides may be hydrolysed to release the fatty acids from the triglyceride ester and then purified typically by fractionation and/or distillation to obtain the fatty acids which can be used in this invention.
  • a typical composition of a fatty acid mixture obtained from a byproduct of olive oil production comprises from 70 to 85 wt % oleic acid and 5 to 20 wt % linoleic acid with the balance being C14 to C20 acids.
  • the formulation is preferably applied to the particular crop as an aqueous solution or emulsion in an amount that delivers from 5 to 1000 g per hectare more preferably from 5 to 500 g per hectare of the unsaturated acid or acids and derivatives.
  • the use of the acid or acids can also reduce the requirement of the amount of the expensive pyrethrin required for a particular performance by at least 50%. It may be necessary to dissolve the acids and/or derivatives thereof in a water soluble solvent such as propylene glycol.
  • the invention is useful with any naturally occurring pyrethrins including pyrethrin I, cinerin I, jasmolin I and pyrethrin II, cinerin II and jasmolin.
  • Piperonyl butoxide is known to enhance the interaction between pyrethrins and ATPase and we have now found that although pyrethrins primarily act on the sodium channels of insects; there is also an interaction with an enzyme (ATPase) that regulates the energy required by ion channels within the insect.
  • ATPase an enzyme that regulates the energy required by ion channels within the insect.
  • Natural compounds that contain the same methylenedioxyphenyl moiety as PBQ also enhance pyrethrin interaction with ATPase. Therefore, in one aspect of this invention a natural compound containing an MDP moiety is included in theiformulation to produce a combination of P450-inhibition acids together with the ATPase enhancement by the MDP containing compound.
  • the preferred amount of the MDP compound when used is from 5 to 500g per hectare.
  • the effective treat rate will depend upon the insect that is to be targeted which may also depend upon the crop that is to be treated. Generally we found that the registered field rate is effective, but the invention may allow a reduction of this rate in some situations.
  • the preferred insecticide formulations of this invention are adapted for spraying onto crops and are typically aqueous emulsions or solutions of the C16 to C24 mono- or polyunsaturated acid or acids and/or alkali metal salts thereof and the pyrethrin and which may be separate solutions for sequential application or as a single formulation.
  • the C16 to C24 mono- or polyunsaturated acid or its alkali metal salt is water soluble.
  • Preferred aqueous formulations for agricultural spraying contain from 5 to 500 g per hectare of the C16 to C24 mono- or poly unsaturated acid or its derivatives optionally together with a solubiliser to improve the solubility of the acid or acids in water with the balance being water.
  • Other additives such as antioxidants and viscosity modifiers may be included as may emulsifiers if the aqueous formulation is an emulsion. Any other materials are preferably naturally occurring products or are derived therefrom.
  • the amount of the formulation that should be employed depends upon the target but typically we have found that formulations that provide from 50 to 250 grams of the C16 to C24 carboxylic acid or acids or alkali metal salts thereof per hectare, preferably 75 to 150 grams per hectare are effective.
  • the invention can be used against a variety of insects including, but not limited to, the following families of mites:
  • Tetranychidae Examples: Tetranychus urticae (two-spotted mite), T. pacificus ( Pacific mite), T. mcdanieli (McDaniel mite), T. turkestani (strawberry mite), Panonychus ulni (European red mite), P. citri (citrus red mite), Oligonychus pratensis (Banks grass mite), O. punicae (avocado brown mite), Eutetranychus hicoriae (pecan leaf scorch mite), Byrobia praetiosa (clover mite).
  • Eriophyidae rust and blister mites: Examples: Phyllocoptruta oleivora (citrus rust mite), Eriophyes sheldoni (citrus bud mite), E. erinea (walnut blister mite), Epitrimerus pyri (pear rust mite), Aculops lycopersici (tomato russet mite).
  • Tenuipalpidae Examples: Brevipalpus lewisi (citrus flat mite), B. phoenicis (red and black flat mite), Dolichotetranychus floridanus (pineapple false spider mite).
  • Tarsenomidae Examples: Steneotarsonemus bancrofti (sugarcane stalk mite), S. ananas (pineapple tarsenomid), S. pallidus (cyclamen Acarapis woodi (honeybee mite).
  • the invention can be used against the following families of sucking insects:
  • Aleyrodidae (whiteflies): Examples: Bemisia tabaci (sweetpotato whitefly), Trialeurodes vaporariorum (greenhouse whitefly), Siphoninus phillyreae (ash whitefly), Dialeurodes citrifolii (cloudywinged whitefly), Aleurocanthus woglumi (citrus blackfly). Aphids, including peach-potato aphid (Myzus persicae), cotton aphid (Aphis gossypii).
  • Nitidulidae examples Meligethes aeneus (pollen beetle).
  • Psyllidae examples: Psylla pyricol (pear psylla), Paratrioza cockerelli (potato/tomato psyllid).
  • the invention can be used against leaf mining flies of the order Dipte . ra and family Agromyzidae.
  • these flies are Liriomyza complex (serpentine leafminers), Phytomyza syngenesiae (chrysanthemum leafminer), Agromyza frohtella (alfalfa blotch leafminer), Ophiomyia phaseoli (bean fly).
  • Diptera mosquitoes, subfamily Anophelinae and subfamily Culicinae.
  • target pests include, but are not limited to, Thysanoptera (thrips), Hymenoptera (wasps), Hemiptera , (bugs), Cicadellidae (leafhoppers), Membracidae (treehoppers), Coccidae (scales), Pseudococcidae (mealybugs),- Diaspididae (scales), and Solenopsis (fire ants).
  • the invention is also useful against mosquitos particularly in tropical and sub-tropical climates.
  • the invention is illustrated by reference to the following example in which the insecticide performance of mixtures of natural pyrethrins and acid mixtures obtained as a by-product from the pressing in olive oil production by fractionation and distillation was determined.
  • the In vivo bioassay method used was based on IRAC method 01 1.
  • a single concentration of the synthetic pyrethrum Alpha-cypermethrin which also gave approximately 25% mortality (0.00003%, 0.3 ppm) dissolved in acetone (0.5 mL) again in the presence or in the absence of the acid mixture (ratio of 1 part pyrethrum to 3.3 parts synergist) were pipetted into glass vials and allowed to evaporate whilst the vials were rotated on a roller mixer to produce Mixture B.
  • the pH of the acid containing formulations was about 5.0.
  • a single concentration of technical grade naturally occurring pyrethrin (1 ppm) dissolved in acetone (0.5 mL) both with and without 0.001 % of the acid combination used in Example 1 were pipetted into glass vials.
  • the formulation containing the acid had a pH of 5.
  • the formulations were allowed to evaporate whilst the vials were rotated on a roller mixer.
  • Meligethes aeneus (pollen beetle) were collected from field mustard plants (Sinapsis arvensis bordering a field crop outside of Datchworth, Herts.
  • a single concentration of technical grade pyrethrin (3 ppm) dissolved in acetone (0.5 mL) in the presence/absence of 0.003% of the acid mixture used in Example 1 together with 0.001 % myristicin or 0.001 % piperine were pipetted into glass vials. Further aliquots of 0.5 mL acetone containing 0.003% of the acid mixture used in Example 1 with 0.001 % myristicin or 0.001 % piperine were also assayed as controls.
  • the formulation containing the acid had a pH of 5. The formulations were allowed to evaporate whilst the vials were rotated on a roller mixer.

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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

L'invention concerne des formulations insecticides comportant des mélanges de pyréthrines d'origine naturelle et d'acides gras insaturés en C16 à C24 qui augmentent la puissance de la pyréthrine d'origine naturelle.
PCT/EP2018/000310 2017-06-19 2018-06-19 Formulations insecticides améliorées Ceased WO2018233869A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP18752684.3A EP3641546A1 (fr) 2017-06-19 2018-06-19 Formulations insecticides améliorées

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1709736.1A GB2563597B (en) 2017-06-19 2017-06-19 Improved Insecticide Formulations
GB1709736.1 2017-06-19

Publications (1)

Publication Number Publication Date
WO2018233869A1 true WO2018233869A1 (fr) 2018-12-27

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ID=59462383

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PCT/EP2018/000310 Ceased WO2018233869A1 (fr) 2017-06-19 2018-06-19 Formulations insecticides améliorées

Country Status (3)

Country Link
EP (1) EP3641546A1 (fr)
GB (1) GB2563597B (fr)
WO (1) WO2018233869A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024089230A1 (fr) 2022-10-28 2024-05-02 Vebi Istituto Biochimico S.r.l. Alcools hydrocarbonés et leurs dérivés en tant qu'agents synergiques dans l'activité pesticide

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2425530A (en) * 1942-12-26 1947-08-12 Thompson Boyce Plant Res Insecticide
DE3717467A1 (de) * 1987-05-23 1988-12-01 Pearson & Co Gmbh & Co Biologisches insektizidspray
FR2634103A1 (fr) * 1988-07-13 1990-01-19 Sogard Services Sarl Procede et produit permettant l'elimination des insectes nuisibles et accelerant le developpement des plantes traitees
US4904645A (en) * 1988-01-27 1990-02-27 Safer, Ltd. Environmentally safe, broad spectrum insecticide
WO2005022167A2 (fr) * 2003-08-29 2005-03-10 The University Of North Carolina At Greensboro Composes a action modulatrice de la croissance d'insectes et procedes et systemes d'identification de tels composes
JP2011251922A (ja) * 2010-06-01 2011-12-15 Dainippon Jochugiku Co Ltd コバエ防除用スプレー剤
ES2444991A1 (es) * 2012-08-27 2014-02-27 Seipasa S.A. Un insecticida ecológico, procedimiento de producción del insecticida y utilización del mismo
WO2017005728A1 (fr) * 2015-07-09 2017-01-12 Apreslabs Ltd Inhibiteurs enzymatiques qui confèrent une résistance aux pesticides

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5700473A (en) * 1995-08-24 1997-12-23 W. Neudorff Gmbh Kg Triglyceride enhanced pyrethrin-based arthropodicidal composition
US20050244445A1 (en) * 2004-04-15 2005-11-03 Anderson David L Insecticidal compositions and methods of using same
US8404260B2 (en) * 2008-04-02 2013-03-26 Bayer Cropscience Lp Synergistic pesticide compositions

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2425530A (en) * 1942-12-26 1947-08-12 Thompson Boyce Plant Res Insecticide
DE3717467A1 (de) * 1987-05-23 1988-12-01 Pearson & Co Gmbh & Co Biologisches insektizidspray
US4904645A (en) * 1988-01-27 1990-02-27 Safer, Ltd. Environmentally safe, broad spectrum insecticide
FR2634103A1 (fr) * 1988-07-13 1990-01-19 Sogard Services Sarl Procede et produit permettant l'elimination des insectes nuisibles et accelerant le developpement des plantes traitees
WO2005022167A2 (fr) * 2003-08-29 2005-03-10 The University Of North Carolina At Greensboro Composes a action modulatrice de la croissance d'insectes et procedes et systemes d'identification de tels composes
JP2011251922A (ja) * 2010-06-01 2011-12-15 Dainippon Jochugiku Co Ltd コバエ防除用スプレー剤
ES2444991A1 (es) * 2012-08-27 2014-02-27 Seipasa S.A. Un insecticida ecológico, procedimiento de producción del insecticida y utilización del mismo
WO2017005728A1 (fr) * 2015-07-09 2017-01-12 Apreslabs Ltd Inhibiteurs enzymatiques qui confèrent une résistance aux pesticides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 201427, Derwent World Patents Index; AN 2014-F57733, XP002784887 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024089230A1 (fr) 2022-10-28 2024-05-02 Vebi Istituto Biochimico S.r.l. Alcools hydrocarbonés et leurs dérivés en tant qu'agents synergiques dans l'activité pesticide

Also Published As

Publication number Publication date
GB2563597B (en) 2023-05-17
GB201709736D0 (en) 2017-08-02
GB2563597A (en) 2018-12-26
EP3641546A1 (fr) 2020-04-29

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