[go: up one dir, main page]

WO1998019994A1 - Insecticides a base de benzophenyluree et procedes d'utilisation de certaines benzophenylurees pour la lutte contre les blattes, les fourmis, les mouches et les termites - Google Patents

Insecticides a base de benzophenyluree et procedes d'utilisation de certaines benzophenylurees pour la lutte contre les blattes, les fourmis, les mouches et les termites Download PDF

Info

Publication number
WO1998019994A1
WO1998019994A1 PCT/US1997/019864 US9719864W WO9819994A1 WO 1998019994 A1 WO1998019994 A1 WO 1998019994A1 US 9719864 W US9719864 W US 9719864W WO 9819994 A1 WO9819994 A1 WO 9819994A1
Authority
WO
WIPO (PCT)
Prior art keywords
termites
compound
fleas
ants
cockroaches
Prior art date
Application number
PCT/US1997/019864
Other languages
English (en)
Inventor
Ronald E. Hackler
George W. Johnson
John M. Owen
Original Assignee
Dow Agrosciences Llc
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 Dow Agrosciences Llc filed Critical Dow Agrosciences Llc
Priority to AU51004/98A priority Critical patent/AU5100498A/en
Publication of WO1998019994A1 publication Critical patent/WO1998019994A1/fr

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

  • This invention provides novel benzoylphenylurea insecticides and novel methods of control cockroaches, ants, fleas, and termites.
  • a broad class of benzoylphenylurea insecticides is disclosed in U.S. Patent No. 3,748,356.
  • Hexaflumuron a commercially significant benzoylphenylurea, is disclosed in U.S. Patent No. 4,468,405.
  • Use of hexaflumuron in methods of controlling termites is disclosed in WO 93/24011.
  • Use of hexaflumuron to control cockroaches is disclosed in WO 94/03066.
  • the invention provides new compounds of formula (I) :
  • the invention also provides a method of controlling cockroaches, ants, fleas, or termites which comprises delivering an effective amount of a compound of the formula (I) to a location where control of cockroaches, ants, fleas, or termites is desired.
  • German cockroach 2nd instars (Blattella germanica) Continuous, low-dose ingestion exposure (treated cornmeal) Rates: (0.19), 0.78, 3.12, 12.5, 50, 200 ppm
  • Rates 0.1, 1.0, 10, 100, 1000 ppm
  • RIFA Solenopsis invicta
  • Pharaoh Ant Monomorium pharaonis
  • Compound 1 is significantly more potent than hexaflumuron based on a short exposure study with RIFA.
  • the compound is normally formulated with a carrier and/or a surface-active agent .
  • a carrier in the present context is any material with which the compound of formula (1) (active ingredient) is formulated to facilitate application to the locus, or storage, transport or handling.
  • a carrier may be a solid or a liquid, including a material which is normally gaseous but which has been compressed to form a liquid. Any of the carriers normally used or known to be usable in formulating insecticidal compositions may be used.
  • compositions according to the invention contain 0.0001 to 99.9% by weight active ingredient.
  • compositions according to the invention contain 0.001 to 10.0% by weight of active ingredient though proportions as low as 0.0001% may be useful in some circumstances.
  • Suitable solid carriers include natural and synthetic clays and silicates, for example natural silicas such as diatomaceous earths; magnesium silicates, for example talcs; magnesium aluminium silicates, for example attapulgites and vermiculites; aluminium silicates, for example kaolinites, montmorillonites and micas; calcium carbonate; calcium sulphate; ammonium sulphate; synthetic hydrated silicon oxides and synthetic calcium or aluminium silicates; elements, for example carbon and sulfur; natural and synthetic resins, for example coumaronne resins, polyvinyl chloride, and styrene polymers and copolymers; solid polychlorophenols ; bitumen; waxes; agar; and solid fertilizers, for example superphosphates.
  • natural silicas such as diatomaceous earths
  • magnesium silicates for example talcs
  • magnesium aluminium silicates for example attapulgites and vermiculites
  • aluminium silicates for example kaolinites
  • Cellulose based materials for example wood, sawdust, agar, paper products, cotton linter, or Methocel®, as well as the other solid carriers that are themselves attractive to or at least non-repellant to termites are particularly suitable and preferable. Mixtures of different solids are often suitable. For example, a mixture of wood flour and agar formulated as a moisture containing solid would be preferable.
  • Suitable liquid carriers include water; alcohols, for example isopropanol and glycols; ketones, for example acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone; ethers; aromatic or aliphatic hydrocarbons, for example benzene, toluene and xylene; petroleum fractions, for example kerosene and light mineral oils; chlorinated hydrocarbons, for example carbon tetrachloride, perchloroethylene and trichloroethane; polar organic liquids, such as dimethyl formamide, dimethyl acetamide, dimethyl sulfoxide and N-methylpyrrolidone; oils derived from plants, such as corn oil and peanut oil. Mixtures of different liquids are often suitable, for example a mixture of isophorone with a polar organic solvent such as N-methylpyrrolidone, as are mixtures of solid and liquid carriers.
  • Pesticidal compositions are often formulated and transported in a concentrated form which is subsequently diluted by the user before application.
  • a carrier which is a surface-active agent facilitates this process of dilution.
  • at least one carrier in such a composition which is a surfaceactive agent may contain at least two carriers, at least one of which is a surface-active agent.
  • a surface-active agent may be an emulsifying agent, a dispersing agent or a wetting agent; it may be nonionic or ionic.
  • suitable surface- active agents include the sodium or calcium salts of polyacrylic acids and lignin sufonic acids; the condensation of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitol, sucrose or pentaerythritol; condensates of these with ethylene oxide and/or propylene oxide; condensates of these with ethylene oxide and/or propylene oxide; condensation products of fatty alcohol or alkyl phenols, for example p-octylphenol or p-octylcresol , with ethylene oxide and/or propylene oxide; sulfates or sulfonates of these condensation products; alkali or alkaline earth metal
  • Pesticidal compositions may for example be formulated as wettable powders, dusts, granules, baits, solutions, emulsifiable concentrates, emulsions, suspension concentrates and aerosols.
  • Wettable powders usually contain 25, 50 or 75% weight of active ingredient and usually contain in addition to solid inert carrier, 3-10% weight of a dispersing agent and, where necessary, 0-10% weight of stabilizer (s) and/or other additives such as penetrants or stickers.
  • Dusts are usually formulated as a dust concentrate having a similar composition to that of a wettable powder but without a dispersant, and are diluted in the field with further solid carrier to give a composition usually containing 0.5-10% weight of active ingredient.
  • Granules are usually prepared to have a size between 10 and 100 BS mesh (1.676-0.152 mm), and may be manufactured by, for example, agglomeration or impregnation techniques. Generally, granules will contain 0.01-75% weight active ingredient and 0-10% weight of additives such as stabilizers, surfactants, slow release modifiers and binding agents.
  • the so-called "dry flowable powders" consist of relatively small granules having a relatively high concentration of active ingredient.
  • the water dispersible granular formulations are in the form of dry, hard granules that are essentially dust-free, and are resistant to attrition on handling, thus minimizing the formation of dust.
  • Such formulation contain 90% or more by weight of finely divided active material, 3-7% by weight of a blend of surfactants, which act as wetting dispersing, suspending and binding agents, and 1-3% by weight of a finely divided carrier, which acts as a resuspending agent .
  • Baits are prepared by, for example, combining a mixture of a suitable food source, such as sawdust for termites or grain or meal for cockroaches, with an amount of active ingredient sufficient to provide the desired result; for example, from about 0.001% to about 20% weight active ingredient and forming the mixture into a paste by the addition of about 1% to 5% of a water based binder such as agar.
  • the paste-like mixture may be applied as is or may be packed into a housing such as a hollowed out wooden dowel or a plastic tube or bait station. In other embodiments, sheets of paper or cardboard can be sprayed with or dipped in a diluted formulation containing the active ingredient. Baits are a preferable embodiment of the present invention.
  • Emulsifiable concentrates usually contain, in addition to a solvent and, when necessary, co-solvent, 10-50% weight per volume active ingredient, 2- 20% weight per volume emulsifiers and 0-20% weight per volume of other additives such as stabilizers, penetrants and corrosion inhibitors.
  • Suspension concentrates are usually compounded so as to obtain a stable, non-sedimenting flowable product and usually contain 10-75% weight active ingredient, 0.5-15% weight of dispersing agents, 0.1-10% weight of suspending agents such as protective colloids and thixotropic agents, 0-10% weight of other additives such as defoamers, corrosion inhibitors, stabilizers, penetrants and stickers, and water or an organic liquid in which the active ingredient is substantially insoluble; certain organic solids or inorganic salts may be present dissolved in the formulation to assist in preventing sedimentation or as anti-freeze agents for water.
  • Aqueous dispersions and emulsions are compositions which may be obtained by diluting a wettable powder or a concentrate with water. The said emulsions may be of the water-in-oil or of the oil-in-water type, and may have a thick 'mayonnaise' -like consistency.
  • the method of applying a compound of Formula (I) to combat termites comprises applying the compound, conveniently in a composition comprising the compound of Formula (I) and a carrier as described above, to a locus or area to be treated for the termites, such as soil or timber, already subject to infestation or attack by termites or intended to be protected from infestation by termites.
  • the active ingredient is, of course, applied in an amount sufficient to effect the desired action of combatting termite infestation. This dosage is dependent upon many factors, including the carrier employed, the method and conditions of the application, whether the formulation is present at the locus in the form of a film, or as discrete particles or as a bait, the thickness of film or size of particles, the degree of termite infestation, and the like.
  • the effective dosage of the compound of the invention at the locus to be protected--i . e . is of the order of 0.001 to 1.0% based on the total weight of the composition, though under some circumstances the effective concentration may be as little as 0.0001% or as much as 2%, on the same basis.
  • the active ingredient When used to control cockroaches, it is preferred to use the active ingredient in a treated bait or as a surface treatment.
  • the active ingredient When used to control ants, it is preferred to use the active ingredient in a liquid bait or granular bait.
  • the active ingredient When used to control termites, it is preferred to use the active ingredient in a cellulose based bait.
  • Suitable formulations include granular, paste, or dust cockroach bait, SP or WP cockroach and/or flea sprayables, cellulose-based termite baits, liquid or granular ant baits , feed-through or topical animal treatment for fleas.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • 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 des composés représentés par la formule générale (I). Dans cette formule générale (I), R1 est -CF=CFCF¿3? ou -CF2CF=CFCF3. Ces composés conviennent particulièrement à la lutte contre les blattes, les fourmis, les mouches et les termites.
PCT/US1997/019864 1996-11-08 1997-10-31 Insecticides a base de benzophenyluree et procedes d'utilisation de certaines benzophenylurees pour la lutte contre les blattes, les fourmis, les mouches et les termites WO1998019994A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU51004/98A AU5100498A (en) 1996-11-08 1997-10-31 New benzoylphenylurea insecticides and methods of using them to control cockroaches, ants, fleas, and termites

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US2974296P 1996-11-08 1996-11-08
US60/029,742 1996-11-08

Publications (1)

Publication Number Publication Date
WO1998019994A1 true WO1998019994A1 (fr) 1998-05-14

Family

ID=21850640

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1997/019864 WO1998019994A1 (fr) 1996-11-08 1997-10-31 Insecticides a base de benzophenyluree et procedes d'utilisation de certaines benzophenylurees pour la lutte contre les blattes, les fourmis, les mouches et les termites

Country Status (2)

Country Link
AU (1) AU5100498A (fr)
WO (1) WO1998019994A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1080722A1 (fr) * 1999-08-31 2001-03-07 Novartis AG Compositions antimycotiques
CN112279748A (zh) * 2020-12-24 2021-01-29 浙江巨化技术中心有限公司 一种1,1,2,2-四氟乙烷的制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0004030A2 (fr) * 1978-03-13 1979-09-19 Ciba-Geigy Ag N-phényl-N'-fluorobenzoyl urées substituées, leurs procédés de préparation et leur utilisation comme pesticides
US4468405A (en) * 1981-07-30 1984-08-28 The Dow Chemical Company Substituted N-aroyl N'-phenyl urea compounds
WO1993024011A1 (fr) * 1992-06-01 1993-12-09 Dowelanco Nouvelle utilisation de l'hexaflumuron et de composes derives en tant que termiticides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0004030A2 (fr) * 1978-03-13 1979-09-19 Ciba-Geigy Ag N-phényl-N'-fluorobenzoyl urées substituées, leurs procédés de préparation et leur utilisation comme pesticides
US4468405A (en) * 1981-07-30 1984-08-28 The Dow Chemical Company Substituted N-aroyl N'-phenyl urea compounds
WO1993024011A1 (fr) * 1992-06-01 1993-12-09 Dowelanco Nouvelle utilisation de l'hexaflumuron et de composes derives en tant que termiticides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1080722A1 (fr) * 1999-08-31 2001-03-07 Novartis AG Compositions antimycotiques
WO2001015684A3 (fr) * 1999-08-31 2001-09-27 Novartis Ag Medicament antimycosique
CN112279748A (zh) * 2020-12-24 2021-01-29 浙江巨化技术中心有限公司 一种1,1,2,2-四氟乙烷的制备方法

Also Published As

Publication number Publication date
AU5100498A (en) 1998-05-29

Similar Documents

Publication Publication Date Title
AU742557B2 (en) Synergistic juvenoid/chitin synthesis inhibitor termiticide compositions
EP0161019B1 (fr) Composés benzoylurées pesticides
CA1337327C (fr) Methode de lutte contre les termites
US4833151A (en) Insecticidal Ureas and thioureas
US6303657B1 (en) Benzoylphenylurea insecticides and methods of using certain benzoylphenylureas to control ants
US4572914A (en) Insecticidal 4-substituted-3-chlorophenyl-1-(fluoroalkoxyphenylcarbamoyl)pyrazolines
US5811461A (en) Benzoylphenylurea insecticides and methods of using them to control cockroaches, ants, fleas, and termites
CA1244471A (fr) Composes actif contre les acariens, les aleurodes et les thrips et nouveau compose de benzoyluree
EP0936867B1 (fr) Insecticides de benzoylphenyl uree et procedes d&#39;utilisation de certains benzoylphenyl urees dans la lutte contre les cafards, les fourmis, les puces et les termites
EP0065334B1 (fr) Dérivés de pyrazoline, leur procédé de préparation, et les préparations insecticides les contenant
US6040345A (en) Benzoylphenylurea insecticides and methods of using them to control cockroaches
WO1998019994A1 (fr) Insecticides a base de benzophenyluree et procedes d&#39;utilisation de certaines benzophenylurees pour la lutte contre les blattes, les fourmis, les mouches et les termites
US5945453A (en) Benzoylphenylurea insecticides to control cockroaches
WO1995016354A1 (fr) Procede pour lutter contre les termites et d&#39;autres insectes destructeurs du bois
EP0008474B1 (fr) Compositions pesticides contenant un sulfure d&#39;acide carbamique et un insecticide pyréthroide synthétique et leur utilisation
US4501742A (en) Insecticidal 3-formyl-2-nitromethylene-2H-1,3-thiazine
AU750562B2 (en) New benzoylphenylurea insecticides and methods of using certain benzoylphenylureas to control cockroaches, ants, fleas, and termites
GB1594261A (en) Benzyloxime ethers
US4783485A (en) Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same
US4234573A (en) 1-Trimethylsilylphenyl-3-mono- and -di-halobenzoyl-ureas, insecticidal compositions containing them and their use in controlling insect pests
US4758570A (en) Pesticidal nitromethylene derivatives
EP0171853A2 (fr) Dérivés de benzoylurées à activité pesticide
CA2271821A1 (fr) Nouveaux insecticides de benzoylphenyl uree et procedes d&#39;utilisation de certains benzoylphenyl urees dans la lutte contre les cafards, les fourmis, les puces et les termites
MXPA99004980A (en) New benzoylphenylurea insecticides and methods of using certain benzoylphenylureas to control cockroaches, ants, fleas, and termites
EP0031974A2 (fr) Composés d&#39;urée et de thiourée, leur méthode de préparation et compositions insecticides les contenant

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE GH HU IL IS JP KE KG KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG UZ YU ZW AM AZ BY KG KZ MD RU TJ TM

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH KE LS MW SD SZ UG ZW AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF

121 Ep: the epo has been informed by wipo that ep was designated in this application
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

NENP Non-entry into the national phase

Ref country code: JP

Ref document number: 1998521613

Format of ref document f/p: F

122 Ep: pct application non-entry in european phase