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
  • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
  • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
  • A01N31/14—Ethers
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
  • C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen

Definitions

• This invention relates to the control of whitefly and is particularly directed to the control of resistant strains of whitefly.
• the present invention provides a method of combating a resistant strain of whitefly at a locus infested by the resistant strain of whitefly comprising applying to the locus an amount effective to combat the whitefly of at least one compound of formula I.
• Y is CH 2 , CHF or O and Z is CH 2 , or Y is CH or CF and Z is CH, Y and Z forming a double bond, or Y is CH 2 and Z is CO; Rl is optionally substituted phenyl;
• R.2 is hydrogen and R ⁇ is CF3, isopropyl or cyclopropyl, or R ⁇ and R-> are methyl, or R2 and R ⁇ together form a cyclopropyl ring;
• Ar is a phenyl or naphthyl group optionally substituted by one or more halogen, alkoxy, haloalkoxy, methylenedioxy, C j -Cg alkyl or haloalkyl groups.
• Ar in formula I represents a phenyl group, preferably substituted at the para position.
• Preferred substituents are halogen, particularly chlorine and fluorine and alkoxy, especially ethoxy.
• R* is preferably an unsubstituted phenyl group.
• optically active carbon atoms may be present. It is intended to include optically active as well as racemic forms of such compounds.
• the compounds preferably have the two carbon-containing substituents in a trans configuration.
• a particularly preferred group of compounds according to the invention are those of formula II
• a further preferred group of compounds are those of formula III
• W is hydrogen or fluorine and either R ⁇ is hydrogen and R- represents a cyclopropyl group or R* and R ⁇ each represent a methyl group.
• W is hydrogen or fluorine and either R ⁇ is hydrogen and R- represents a cyclopropyl group or R* and R ⁇ each represent a methyl group.
• W is hydrogen
• R ⁇ is hydrogen
• R- represents a cyclopropyl group
• R* and R ⁇ each represent a methyl group.
• Compounds of formula III where W is hydrogen are disclosed in US Patent No. 4975451 and Japanese Patent Publications Nos. 60115545, 60193902 and 60193940.
• W is fluorine
• X is fluorine.
• An additional group of preferred compounds are those of formula IV
• R ⁇ and R J are methyl or R ⁇ is hydrogen and R J is cyclopropyl or R ⁇ and R-* together form a cyclopropyl ring, and W is hydrogen
• the compounds of formula I to VI as described above can be formulated in many ways for use in combating resistant whitefly. They can therefore be employed in a pesticidal composition comprising a compound of formulae I to VI as an active ingredient together with an inert carrier or diluent.
• Suitable diluents include both solid and liquid diluents so as to provide compositions which can be formulated for example as granules, dusts or emulsifiable concentrates.
• diluents suitable for the preparation of granular compositions are porous materials such as pumice, gypsum or corn cob grits.
• Suitable diluents for the preparation of dusts include kaolin, bentonite, kieselguhr or talc.
• various solvents such as ketones and aromatic solvents, may be employed together with one or more known wetting agents, dispersing agents or emulsifying agents.
• compositions especially granules preferably contain from 0.5 to 15% by weight of active ingredient, while liquid compositions, as applied to the crop, may contain as little as from 0.0001 to 1% by weight of active ingredient.
• a composition such as a wettable powder however may contain as much as 75% by weight of active ingredient.
• the compositions may conveniently be applied to the locus of whitefly infestation at an application rate of from 1 to 500 g of active ingredient per hectare.
• compositions may include a mixture of compounds of formula I and/or other ingredients, including another pesticidal material, eg. an insecticide, acaricide or fungicide, or a synergist.
• another pesticidal material eg. an insecticide, acaricide or fungicide, or a synergist.
• compositions may be applicable to foliage soil and/or seeds during cultivation of a wide variety of foliage, horticultural and agricultural crops such as maize, sugar beet, potatoes, tobacco and cotton.
• the compositions are particularly useful in combating resistant strains of
• Bemisia tabaci but are also contemplated for use to combat other resistant whitefly strains such as Trialeurodes vaporariorum and abutilonea.
• Example 4 The method of Example 4 was repeated using a Grignard reagent, prepared from 4-fluoro-3-phenoxyphenyl bromide (0.3 g), tetrahydrofuran (2 ml) and magnesium (28 mg) and 4-(4-chlorophenyl)-2-fluoro-5-methylhex-2-enol (Example 3) (0.96 g).
• a Grignard reagent prepared from 4-fluoro-3-phenoxyphenyl bromide (0.3 g), tetrahydrofuran (2 ml) and magnesium (28 mg) and 4-(4-chlorophenyl)-2-fluoro-5-methylhex-2-enol (Example 3) (0.96 g).
• the compounds 1 to 26 identified in Table 1 were tested against susceptible and resistant strains of whitefly (Bemisia tabaci).
• the susceptible strain "SUD-S” was collected from the Sudan in 1978 by Ciba-Geigy and subsequently laboratory cultured to provide the standard laboratory susceptible strain.
• the resistant strain "BELZ” was collected from broccoli in Caribbean in November 1991. It is an example of this "poinsettia” strain of Bemisia tabaci which is the biotype causing control difficulties in American field crops and glasshouses and in European glasshouses at the time of making the present patent application.
• Acetone solutions (100 ml) ofthe test compounds were placed in glass vials and evaporated with rotation to deposit a film ofthe compound. Thirty adult whiteflies were placed inside the vial, then after 60 minutes, the treated insects were transferred onto untreated cotton leaf discs which were kept moist on a bed of agar gel. The temperature was maintained at 25 °C and mortality assessed after 48 hours. Three replicates were used at each of 5 to 7 dose levels per compound. LC50 values were calculated by using a computer software package ("Polo-PC" available from LeOra Software, Berkeley, California). The LC50 values are given in ppm (i.e. concentration ofthe acetone solution used) in Table 2 below. Several commercially available pyrethroid esters and one organochlorine insecticide (DDT) are included in the Table for reference.
• DDT organochlorine insecticide

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

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• 1995
  • 1995-10-30 GB GBGB9522144.6A patent/GB9522144D0/en active Pending
• 1996
  • 1996-10-28 BR BR9611503A patent/BR9611503A/pt not_active Application Discontinuation
  • 1996-10-28 AU AU73188/96A patent/AU7318896A/en not_active Abandoned
  • 1996-10-28 WO PCT/GB1996/002622 patent/WO1997016067A1/en not_active Application Discontinuation
  • 1996-10-28 JP JP9516114A patent/JPH11514369A/ja active Pending
  • 1996-10-28 EP EP96935094A patent/EP0876099A1/en not_active Withdrawn
  • 1996-10-28 KR KR1019980703160A patent/KR19990067206A/ko not_active Application Discontinuation
  • 1996-10-28 NZ NZ320450A patent/NZ320450A/xx unknown
  • 1996-10-30 ZA ZA969126A patent/ZA969126B/xx unknown

Non-Patent Citations (1)

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