EP0449885A1 - Usage insecticide d'une benzoyluree - Google Patents

Usage insecticide d'une benzoyluree

Info

Publication number
EP0449885A1
EP0449885A1 EP19900900671 EP90900671A EP0449885A1 EP 0449885 A1 EP0449885 A1 EP 0449885A1 EP 19900900671 EP19900900671 EP 19900900671 EP 90900671 A EP90900671 A EP 90900671A EP 0449885 A1 EP0449885 A1 EP 0449885A1
Authority
EP
European Patent Office
Prior art keywords
compound
attractant
formula
fluoro
pests
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Withdrawn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
EP19900900671
Other languages
German (de)
English (en)
Inventor
Clyde Allen Roberts
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP0449885A1 publication Critical patent/EP0449885A1/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Withdrawn legal-status Critical Current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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
    • C07C275/48—Y being a hydrogen or a carbon atom
    • C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas

Definitions

  • U.S. 4,666,942 and U.S. 4,698,365 disclose the compound of Formula I and its use as an insecticide.
  • EP 275,132 discloses the compound of Formula I for use against termites.
  • the compound of this invention has been found to have a mode of action as a growth regulant and chitin growth inhibitor in cockroaches and other household pest species.
  • Other household pests against which this compound is particularly effective include flies, ants and carpet beetles.
  • the compound of Formula I can be prepared by reacting a compound of the formula
  • R represents, independently, NH 2 or NCO.
  • the reaction can be carried out in the presence of a solvent.
  • Suitable solvents are aromatic solvents such as benzene, toluene, xylene, or chlorobenzene, hydrocarbons such as petroleum fractions, chlorinated hydrocarbons such as chloroform, methylene chloride or dichloroethane, and ethers such as diethyl ether, dibutyl ether, or dioxan. Mixtures of solvents are also suitable.
  • the reaction is carried out at a temperature from 0°C to 100°C.
  • the molar ratio of isocyanate to amine is from about 1:1 to 2:1.
  • the reaction is carried out under anhydrous conditions.
  • Step A Preparation of 2-fluoro-4-(2-chloro-4- rtrifluoromethylTphenoxy)aniline
  • Step B Preparation of N-(2.6-difluorobenzoyl)-N'- (2-fluoro-4-r2-chloro-4-(trifluoromethyl)- phenoxylphenylurea (Compound of Formula I)
  • a solution of the compound of Step A (0.9 g) in dry toluene (5 ml) was treated with 2,6-difluoro- benzoylisocyanate (0.56 g) and the mixture was stirred at room temperature overnight. The precipitated product was then separated, washed with cold methanol and dried in an oven at 60°C to give 1.15 g of the desired product, melting point 173 to 175°C.
  • the compound of this invention will typically be used in formulation with a pesticidally suitable carrier comprising a liquid or solid diluent or an organic solvent.
  • a pesticidally suitable carrier comprising a liquid or solid diluent or an organic solvent.
  • Useful formulations of Formula I compound can be prepared in conventional ways. They include dusts, granules, baits, pellets, solutions, suspensions, emulsions, wettable powders, aerosols, emulsifiable concentrates, dry flowables and the like. Many of these can be applied directly. Sprayable formulations can be extended in suitable media and used at various spray volumes. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations broadly, contain about 0.01% to 99% by weight of active ingredien (s) and at least one of a) about 0.1% to 20% surfactant(s) and b) about 5% to 99% solid or liquid diluent(s). More specifically, they will contain effective amounts of these ingredients in the following approximate proportions: Percent by Weight
  • Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts.
  • Typical liquid diluents and solvents are described in Marsden, “Solvents Guide,” 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C. "McCutcheon"s Detergents and Emulsifiers Annual", Allured Publ.
  • Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration”, Chemical Engineering. December 4, 1967, pages 147 and following, and "Perry's Chemical Engineer's Handbook", 4th Ed., McGraw-Hill, New York, 1963, pages 8 to 59 and following.
  • the ingredients are combined and stirred with gentle warming to speed solution.
  • a fine screen filter is included in packaging operation to insure the absence of any extraneous undissolved material in the product.
  • the wettable powder and the pyrophyllite diluent are thoroughly blended and then packaged.
  • the product is suitable for use as a dust.
  • the ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 mm (U.S.S. No. 18 to 40 sieves), the gran ⁇ ules are removed, dried, and screened. Oversize material is crushed to produce additional material in the desired range. These granules contain 4.5% active ingredient.
  • the ingredients are combined and stirred to produce a solution suitable for direct, low volume application.
  • the ingredients are mixed in a blender.
  • the ingredients are then ground together in an airmill and compacted in a roll compactor.
  • the sheets are then broken up and sifted.
  • the material that is the proper size is packaged (about 0.15 to 2.0 mm).
  • the ingredients are mixed together in a blender and ground in a hammer-mill.
  • the mixture is then extruded in a ring type extruder to produce pellets.
  • the pellets are then screened to remove fines and . packaged.
  • the polymer acts as a framework that encompasses the toxicant and holds it for ingestion by the insect.
  • the compound of Formula I can also be mixed with one or more other insecticides, acaricides, or other biologically active compounds to form a multi-component pesticide giving broad protection against household pests.
  • insecticides with which the compound of Formula I can be used are: chloropyrifos, methoprene, hydramethylnon, abamectin, fenoxycarb, dichlorvos, diazinon, propetamphos, propoxur, bendiocarb and natural and synthetic pyrethroids.
  • Utility The compound described herein exhibits activity against several species of household pests although those skilled in the art will recognize that it may not be equally effective against all such pests.
  • Household pests are undesirable insect species normally found to inhabit the household environment.
  • the specific species for which control is exemplified hereafter is Blattella germanica .
  • Application Insects are controlled and human health is protected by applying the Formula I compound, in an effective amount, to the locus of infestation, to the area to be protected, to a food source or directly on the pests to be controlled.
  • a preferred method of application is by spraying the compound in the environment of the pests.
  • the compound can be incorporated into baits which are consumed or in devices such as traps and the like which entice the insects to ingest or otherwise contact the toxicant.
  • the compound can be applied in its pure state, but most often application will be of a formulation comprising the compound in a suitable entraining carrier or diluent, possibly in combination with a food.
  • a most preferred method of application involves a bait formulation or spraying a water dispersion of a formulation of the compound.
  • the rate of application required for effective control will depend on such factors as the species of insect to be controlled, the pest's life stage, its size, its location, time of year of application, ambient moisture, temperature conditions, and the like. In general, application rates of 0.1 to 1 mg of active ingredient per square foot are sufficient to provide effective control under normal circumstances, but as little as 0.05 mg/sq ft may be sufficient or as much as 4 mg/sq ft may be required, depending upon the factors listed above.
  • a second method of application is to incorporate the compound into a bait that will be ingested by the pest.
  • application rates of about 2 to 5 ppm of active ingredient, by total weight, are sufficient to provide effective control under normal circumstances, but as little as 0.1 ppm may be sufficient or as much as 20 ppm may be required depending upon the factors listed.
  • Aluminum foil-covered panels (6" x 6") were treated with acetone solution of compound I at the rate of 0.7 mg/sq ft (active ingredient). This was replicated three times. Each was placed in a two gallon glass jar with twenty-five third instar Blattella germanica. Two pieces of lab chow (Wayne Rodent Blox®) was placed in each jar. Mortality was assessed after two weeks.
  • Example 3 Samples of compound I were incorporated into portions of lab chow in varying amounts. These were fed to fifth instar Blatella germanica nymphs which had fasted for twenty-four hours. Mortality was determined seven days after post molting.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Est décrit un procédé pour lutter contre des parasites domestiques choisis, par la mise en contact de ceux-ci ou de leur environnement avec une N-(2,6-difluorobenzoyl)N'-(2-fluoro-4-[2-chloro-4-(trifluorométhyl)phénoxy]phénylurée).
EP19900900671 1988-12-21 1989-12-11 Usage insecticide d'une benzoyluree Withdrawn EP0449885A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US28726788A 1988-12-21 1988-12-21
US287267 1988-12-21

Publications (1)

Publication Number Publication Date
EP0449885A1 true EP0449885A1 (fr) 1991-10-09

Family

ID=23102162

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19900900671 Withdrawn EP0449885A1 (fr) 1988-12-21 1989-12-11 Usage insecticide d'une benzoyluree

Country Status (2)

Country Link
EP (1) EP0449885A1 (fr)
WO (1) WO1990006680A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1046910C (zh) * 1994-05-20 1999-12-01 本田技研工业株式会社 两轮机动车的部件安装结构

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU1243292A (en) * 1991-01-22 1992-08-27 E.I. Du Pont De Nemours And Company A benzoylurea-containing composition for parasite control in animals
CA2176596A1 (fr) * 1993-11-18 1995-05-26 Yoshio Katsuda Utilisation de benzoylurees pour lutter contre les acariens detriticoles
GB2370775A (en) * 2001-01-04 2002-07-10 Nimrod Israely Insecticidal composition based on attractant, insecticide and stabilizer, the outer surface of which expands & loses viscosity on contact with humidity
CN103709048B (zh) * 2013-11-14 2017-11-24 江苏中旗作物保护股份有限公司 氟虫脲中间体2‑氟‑4‑(2‑氯‑4‑三氟甲基苯氧基)苯胺的合成方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1460419A (en) * 1975-02-06 1977-01-06 Bayer Ag Benzoylureido-diphenyl ethers and their use as insecticides
CA1339745C (fr) * 1984-04-10 1998-03-17 Martin Anderson Compose pesticides a base de benzoylurees
DE3603089A1 (de) * 1986-02-01 1987-08-06 Basf Ag N-benzoyl-n'-phenoxyphenylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen
GB8700838D0 (en) * 1987-01-15 1987-02-18 Shell Int Research Termiticides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9006680A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1046910C (zh) * 1994-05-20 1999-12-01 本田技研工业株式会社 两轮机动车的部件安装结构

Also Published As

Publication number Publication date
WO1990006680A1 (fr) 1990-06-28

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