EP0474722A1 - Compositions pesticides - Google Patents

Compositions pesticides

Info

Publication number
EP0474722A1
EP0474722A1 EP90908594A EP90908594A EP0474722A1 EP 0474722 A1 EP0474722 A1 EP 0474722A1 EP 90908594 A EP90908594 A EP 90908594A EP 90908594 A EP90908594 A EP 90908594A EP 0474722 A1 EP0474722 A1 EP 0474722A1
Authority
EP
European Patent Office
Prior art keywords
piperonyl butoxide
control
acid ester
composition
gallic acid
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.)
Withdrawn
Application number
EP90908594A
Other languages
German (de)
English (en)
Inventor
Mary Mooney
John Wyatt
Robert Martin
Karen Salisbury
David Peter Hyslop
George Raymond Cayley
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
Wellcome Foundation 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 Roussel Uclaf SA, Wellcome Foundation Ltd filed Critical Roussel Uclaf SA
Publication of EP0474722A1 publication Critical patent/EP0474722A1/fr
Withdrawn legal-status Critical Current

Links

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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
    • 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 novel compositions, their preparation, formulations containing them and to their use for the control of insect pests.
  • Insecticides have been increasingly used in agriculture over the past thirty years to control insect pests, thereby increasing the yield per acre that land under cultivation can provide.
  • the insect population modifies its susceptibility to the insecticide and resistance to that insecticide may occur.
  • resistance to the organochlorine and organophosphorous insecticides was common and, by 1988, resistance to the pyrethroids in certain insect species was becoming widespread.
  • pyrethroid resistance in heliothis species in Australia, Thailand, Turkey and the Americas is becoming a major problem in the cotton growing industry in these countries.
  • Piperonyl butoxide is a potentiator that has been commonly used to potentiate the activity of the pyrethrins and the pyrethroids against susceptible and resistant insect species.
  • Piperonyl butoxide (5-[2-(2-butoxyethoxy)ethoxymethyl]-6-propyl-l,3-benxodioxole) acts by inhibiting enzymes, mixed function oxidases, which are present in susceptible and more so in pyrethrin/pyrethroid and some carbamate resistant insects and degrades these insecticides.
  • n-Propyl- allate is an antioxidant that is commonly used in the food industry as a preservative. It has also been used in insecticide formulations, for example, Hungarian Patent Application No 34100 discloses insecticidal compositions containing inter alia permethrin, piperonyl butoxide and an antioxidant such as n-propyl gallate. We have discovered that BHT and BHA can potentiate the activity of insecticides, such as the pyrethrins, the pyrethroids and the organophosphorus series of insecticides, against susceptible and resistant insect species including Musca domestica and heliothis spp.
  • piperonyl butoxide appears to be adversely effected by light, i.e. piperonyl butoxide is photosensitive; the addition of gallic acid esters to piperonyl butoxide protects piperonyl butoxide against light induced degradation.
  • the present invention provides a composition which comprises piperonyl butoxide a gallic acid ester in a ratio of 3:1 to 1:10 by weight.
  • Suitable gallic acid esters include alkyl esters, most suitably those formed from straight chain alkyl esters where the alkyl substituent contains up to 12 carbon atoms, in particular propyl, octyl and dodecyl gallate esters.
  • the gallic acid ester is n-propyl gallate.
  • the present invention provides an insecticidal composition which comprises an insecticide, piperonyl butoxide and n-propyl gallate, wherein piperonyl butoxide and n-propyl gallate are in a ratio of 3:1 to 1:10 by weight, suitably in a ratio of 2.5:1 to 1:7 and are preferably in a ratio of 2:1 to 1:5 by weight.
  • Suitable insecticides include organophosphorous, pyrethroid, pyrethrin and lipid amide pesticides.
  • Suitable organophosphorous insecticides include:-
  • Suitable pyrethroid insecticides include those of the formula (I)
  • n 0 or 1
  • R is halo, CFmony or CHF ⁇ O, R is hydrogen or halo, and Z and Z are each independently selected from halo, CF_ and methyl, X is halo, and
  • X 1 is H, CN or OCH
  • Preferred pyrethroids for inclusion within the present invention include: -
  • Suitable lipid amide pesticides include those described in European Patent Application nos. Ill 105, 164 187, 194764, 209 289, 225 011, 251472, 269457 and 317 188.
  • insecticide to be applied will depend on the Inherent activity of the insecticide against the insect species to be controlled, the method of application and the nature of the formulation to be applied and whether or not piperonyl butoxide is included In the formulation but in general the following quantities will be applied.
  • Organophophorous insecticides between 50 and 100 g/hectare (0.125 and 2.5 lbs/acre)
  • Lipid amides between 5 and 150 g hectare (0.0125 and 0.4 libs/acre) .
  • Piperonyl butoxide between 100 and 1200 g/hectare (0.25 and 3.0 lbs/acre) .
  • n-Propyl gallate between 33 and 6000 g/hectare (0.08 - 15 lbs/acre) .
  • the formulation for agrochemical use which comprises n-propyl gallate and piperonyl butoxide and/or one or more insecticides from the organophosphorous, pyrethroid, pyrethrin or lipid amide classes of insecticides may contain a suitable carrier.
  • the carrier may be liquid, solid or gaseous or comprise a mixture of such substances, and the composition of the present invention may be present in a concentration of from 0.025 to 99% w/v depending upon whether the formulation requires further dilution.
  • Dusts, powders and granules and other solid formulations comprise the compositions of the present invention in intimate admixture with a powdered solid inert carrier for example suitable clays, kaolin, bentonite, attapulgite, absorbent carbon black, talc, mica, chalk, gypsum, tricalcium phosphate, powdered cork, magnesium siliate, vegetable carriers, starch and diatomaceous earths.
  • a powdered solid inert carrier for example suitable clays, kaolin, bentonite, attapulgite, absorbent carbon black, talc, mica, chalk, gypsum, tricalcium phosphate, powdered cork, magnesium siliate, vegetable carriers, starch and diatomaceous earths.
  • Such solid formulations are generally prepared by impregnating the solid diluents with solutions of the combinations of the present invention in volatile solvents, evaporating the solvents and, if desired grinding the products so as to obtain powders and,
  • Sprays of the compositions of the present invention may comprise a solution in an organic solvent (e.g. those listed below) or an emulsion in water (dip wash or spray wash) prepared in the field from an emulsifiable concentrate (otherwise known as a water miscible oil) which may also be used for dipping purposes.
  • the concentrate preferably comprises a mixture of the active ingredients, with or without an organic solvent and one or more emulsifiers.
  • Solvents may be present within wide limits but preferably in an amount of from 0 to 90% w/v of the composition and may be selected from kerosene, ketones, alcohols, xylene, aromatic naphtha, and other solvents known in the formulating art.
  • the concentration of emulsifiers may be varied within wide limits but is preferably in the range of 5 to 25% w/v and the emulsifiers are conveniently non-ionic surface active agents including polyoxyalkylene esters of alkyl phenols and polyoxyethylene derivatives of hexitol anhydrides and anionic surface active agents including Na lauryl sulphate, fatty alcohol ether sulphates, Na and Ca salts of alkyl aryl sulphonates and alkyl sulphosuccinates, soaps, leuthrins, hydrolysed glues, etc.
  • Cationic emulsifiers include benzalkonium chloride and quaternary ammonium ethosulphates.
  • Amphoteric emulsifiers include carboxymethylated oleic imidazoline and alkyl dimethyl betain.
  • Wettable powders comprise an inert solid carrier(s) , one or more surface active agents, and optionally stabilisers and/or anti-oxidants.
  • Emulsifiable concentrates comprise emulsifying agents, and often an organic solvent, such as kerosene, ketones, alcohols, xylenes, aromatic naphtha, and other solvents known in the art.
  • organic solvent such as kerosene, ketones, alcohols, xylenes, aromatic naphtha, and other solvents known in the art.
  • Wettable powders and emulsifiable concentrates will normally contain from 5 to 95% by weight of the active ingredient, and are diluted, for example with water, before use.
  • Aqueous suspensions of a compound of Formula (I) may comprise a suspension in water together with suspending, stabilising or other agents.
  • the suspensions or solution may be applied per se or in a diluted form in known fashion.
  • Aerosol sprays may be prepared as a simple solution or suspension of the active ingredient in the aerosol propellant and co-solvent such as halogenated alkanes and the solvents referred to above, respectively.
  • Pour-on formulations may be made as a solution or suspension of a combination of the present invention in a liquid medium.
  • Suitably-moulded, shaped plastics articles impregnated with a combination of the present invention including impregnated collars, tags, bands, sheets and strips are also useful formulations.
  • the plastics material is a polyvinyl chloride (PVC) .
  • composition of the present invention may be used to control insect and acarine pests.
  • the present invention provides a method for the control of arthropods and which comprises administering to the arthropod or to its environment an arthropodically effective amount of an insecticidal composition of the present invention.
  • the present invention also provides a method for the control and/or eradication of arthropod infestations of animals and/or of plants, (including trees), and/or stored products which comprises administering to the animal or locus an effective amount of an insecticidal composition of the present invention.
  • the present invention further provides for the insecticidal compositions of the present invention for use in human and veterinary medicine, in public health control and in agriculture for the control of arthropod and/or helminth pests.
  • insectsicidal compositions of the present invention are of particular value in the protection of field, forage, plantation, glasshouse, orchard and vineyard crops, of ornamentals and of plantation and forest trees, for example, cereals (such as maize, wheat, rice, sorghum), cotton, tobacco, vegetables and salads (such as beans, cole crops, curcurbits, lettuce, onions, tomatoes and peppers), field crops (such as potato, sugar beet, ground nuts, soyabean, oil seed rape), sugar cane, grassland and forage (such as maize, sorghum, lucerne), plantations (such as of tea, coffee, cocoa, banana, oil palm, coconut, rubber, spices), orchards and groves (such as of stone and pip fruit, citrus, kiwifruit, avocado, mango, olives and walnuts), vineyards, ornamental plants, flowers and shrubs under glass and in gardens and parks, forest trees (both deciduous and evergreen) in forests, plantations and nurseries.
  • cereals such
  • insecticidal compositions of the present invention are thus useful in the control of arthropods e.g. insects and acarines in any environment where these constitute pests, e.g. in agriculture, in animal husbandry, in public health control and in domestic situations.
  • arthropods e.g. insects and acarines
  • any environment where these constitute pests e.g. in agriculture, in animal husbandry, in public health control and in domestic situations.
  • Insect pests include members of the orders Coleoptera (e.g. Anobium. Geutorhynchus. Rhynchophorus. Cosmopolites. Lissorhoptrus. Meligethes. Hvpothenemus. Hylesinus. Acalvmma. Lema. Psylliodes. Leptinotarsa. Gonocephalum. Agriotes., Dermolepida. Heteronvchus. Phaedon. Triboliu ⁇ t. Sitophilus. Diabrotica. Anthonomus or Anthrenus spp.), Lepidoptera (e.g. Ephestia. Mamestra, Earias. Pectinophora.
  • Coleoptera e.g. Anobium. Geutorhynchus. Rhynchophorus. Cosmopolites. Lissorhoptrus. Meligethes. Hvpothenemus. Hylesinus. Acalvmma. Lema. Ps
  • Diptera e.g. Musca. Aedes. Anopheles. Cule . Glossina. Simuliu . Sto oxys. Haematobia. Tabanus. Hydrotaea. Lucilia. Chrvsomia
  • Acarine pests include ticks, e.g. members of the genera Boophilus. Ornithodorus. Rhipicephalus. Amblyomma. Hvalomma. Ixodes. Haemaphvsalis. Dermacentor and Anocentor. and mites and manges such as Ac rus. Tetranychus. Psoroptes. Notoednes. Sarcoptes. Psorergates. Chorioptes. Eutro bicula. Demodex. Panonychus. Brvobia. Eriophves. Blaniulus. Polyphagotarsonemus. Scutigerella. and Oniscus spp.
  • compositions were measured using standard methods.
  • compositions were applied as a thin film onto glass plates at a
  • Cotton plants were sprayed according to the three treatments below. Insects (Heliothis ar ⁇ gra) were caged onto the foliage at intervals up to 6 days after spraying and the % control results were as follows:
  • Potato plants were treated as indicated and the number of insects present per ive plants recorded at intervals as follows:

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Des compositions insecticides comprenant un organophosphore, un pyréthroïde, une pyréthrine, et/ou un insecticide amide lipide en combinaison avec du pipéronyl butoxyde et un ester d'acide gallique à un taux de 3:1 à 1:10 sont utiles dans le cadre du contrôle des parasites nuisibles.
EP90908594A 1989-05-26 1990-05-25 Compositions pesticides Withdrawn EP0474722A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB898912188A GB8912188D0 (en) 1989-05-26 1989-05-26 Pesticidal compositions
GB8912188 1989-05-26

Publications (1)

Publication Number Publication Date
EP0474722A1 true EP0474722A1 (fr) 1992-03-18

Family

ID=10657436

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90908594A Withdrawn EP0474722A1 (fr) 1989-05-26 1990-05-25 Compositions pesticides

Country Status (10)

Country Link
EP (1) EP0474722A1 (fr)
JP (1) JPH04505453A (fr)
KR (1) KR920700534A (fr)
AU (1) AU635747B2 (fr)
CA (1) CA2046932A1 (fr)
FI (1) FI915330A0 (fr)
GB (1) GB8912188D0 (fr)
HU (1) HU210160B (fr)
MC (1) MC2183A1 (fr)
WO (1) WO1990014006A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU677162B2 (en) * 1991-12-23 1997-04-17 Charles Morgan Jr. Rechargeable dispenser
FR2696318B1 (fr) * 1992-10-01 1995-12-22 Daniel Sincholle Nouvelles preparations medicamenteuses ou d'hygiene corporelle pour l'elimination des parasites du corps, des cheveux et du cuir chevelu et des poils, contenant une association d'insecticides et de substances anti-oxydantes.
GB9927812D0 (en) * 1999-11-25 2000-01-26 Mohammed Al Qubaisi Enterprise Improved pesticide formulation
AP2835A (en) 2007-06-29 2014-02-28 Vestergaard Frandsen Sa Insecticidal barrier partly with synergist
AP2010005113A0 (en) 2007-06-29 2010-02-28 Vestergaard Frandsen Sa Insecticidal thread
WO2009059603A1 (fr) 2007-11-05 2009-05-14 Vestergaard Frandsen Sa Salle avec deux objets insecticides à contre-résistance
KR101960994B1 (ko) * 2011-08-22 2019-03-21 로마노 나투어 게엠베하 붉은야자나무바구미에 대한 고활성 항기생충 조성물

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1274205A (fr) * 1960-11-24 1961-10-20 Kenya Pyrethrum Board Insecticides à base d'extraits de pyrèthre
HU205839B (en) * 1987-11-18 1992-07-28 Chinoin Gyogyszer Es Vegyeszet Synergetic artropodicide composition containining pirethroides and phosphate-esters as active components
HU198830B (en) * 1988-02-05 1989-12-28 Chinoin Gyogyszer Es Vegyeszet Arthropodicides comprising cypermethrin trans-isomers and tetramethrin

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9014006A1 *

Also Published As

Publication number Publication date
JPH04505453A (ja) 1992-09-24
MC2183A1 (fr) 1992-09-16
HU210160B (en) 1995-02-28
CA2046932A1 (fr) 1990-11-27
WO1990014006A1 (fr) 1990-11-29
FI915330A0 (fi) 1991-11-12
AU5720990A (en) 1990-12-18
HUT57980A (en) 1992-01-28
HU905253D0 (en) 1991-12-30
GB8912188D0 (en) 1989-07-12
AU635747B2 (en) 1993-04-01
KR920700534A (ko) 1992-08-10

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