EP0215056A1 - Composes pesticides a base d'uree de 1-(4-phenoxyphenyl)-3-benzoyle, et procede de preparation - Google Patents

Composes pesticides a base d'uree de 1-(4-phenoxyphenyl)-3-benzoyle, et procede de preparation

Info

Publication number
EP0215056A1
EP0215056A1 EP86901632A EP86901632A EP0215056A1 EP 0215056 A1 EP0215056 A1 EP 0215056A1 EP 86901632 A EP86901632 A EP 86901632A EP 86901632 A EP86901632 A EP 86901632A EP 0215056 A1 EP0215056 A1 EP 0215056A1
Authority
EP
European Patent Office
Prior art keywords
compound
chlorine
bromine
effective amount
pesticidally effective
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Withdrawn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
EP86901632A
Other languages
German (de)
English (en)
Inventor
David Teh-Wei Chou
Paul Alfred Cain
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.)
Union Carbide Corp
Original Assignee
Union Carbide Corp
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 Union Carbide Corp filed Critical Union Carbide Corp
Publication of EP0215056A1 publication Critical patent/EP0215056A1/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Withdrawn legal-status Critical Current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

Definitions

  • This invention relates to novel 1-(4-phenoxyphenyl)-3-benzoyl urea compounds which are useful as the active toxicant in pesticidal compositions.
  • This invention also relates to a method for the preparation of the novel 1-(4-phenoxyphenyl)-3-benzoyl urea compounds.
  • This invention further relates to pesticidal compositions and to a method for their use.
  • a further object is to provide novel pesticidal compositions containing the novel benzoyl urea compounds as the active toxicant.
  • Another object of the invention is to provide a method for controlling pests by the application of the novel pesticidal compositions.
  • the invention relates to novel 1-(4-phenoxyphenyl)-3-benzoyl urea compounds, pesticidal compositions containing the same, and processes for their preparation and use.
  • the benzoyl urea compounds of this invention can be represented by the following formula:
  • X represents halogen
  • X' represents hydrogen or halogen
  • X' ' represents fluorine or hydrogen with the proviso that when X' is halogen then X' ' is hydrogen;
  • R 1 , R 2 and R 3 are independently methyl, chlorine or bromine with the proviso that one of R 1 and R 3 is other than chlorine or bromine;
  • R' , R' ' and R' ' ' are independently hydrogen, methyl, chlorine, fluorine or bromine provided that at least one of R', R' ' and R' ' ' is other than hydrogen.
  • the invention relates to novel 1-(4-phenoxyphenyl)-3-benzoyl urea compounds, pesticidal compositions containing the same, and processes for their preparation and use.
  • Preferred benzoyl urea compounds within the broad generic Formula (1) are those having the formulas:
  • novel benzoyl urea compounds of this invention can be conveniently prepared by one or more methods.
  • the compounds of this invention may be prepared by reacting a substituted phenoxyaniline 2 with a benzoyl isocyanate 3 according to Scheme I as follows:
  • the subject compounds may also be prepared by the reaction of a benzoyl chloride 6 with a substituted urea 7 according to Scheme III as follows :
  • the reduction of nitro ether 10 to phenoxyaniline 2 can be achieved by hydrogenation using a catalytic amount of platinum or palladium on carbon or a Raney Nickel catalyst under an atmosphere of hydrogen at a pressure ranging from 40-200 psi at ambient temperature.
  • Suitable solvents for hydrogenation include aromatic hydrocarbons or alcohols.
  • the reduction can also be achieved by a chemical method using hydrazine and a metal catalyst as disclosed in Chem. Rev. , Vol. 65, pp. 51-68 (1965).
  • R 1 or R 3 is chlorine or bromine are obtained upon halogenation of 4-phenoxyanilines 11 and 12 as depicted in Scheme VII below as follows:
  • R, R', R' ' and R' ' ' have the meaning given in
  • R 3 , R, R'. R' ' and R' ' ' have the meaning given in Formula (1) for the transformation of 12 to 2.
  • Suitable solvents for these transformations include aromatic hydrocarbons, such as benzene, or polar protic solvents, such as acetic acid.
  • Halogenation of anilines 1 1 and 12 may be effected by their exposure to chlorine or bromine in a suitable solvent at low temperature or preferably treatment with a N-halosuccinimide in benzene or acetic acid.
  • Temperatures required for the reaction vary according to the identity of substituents R 2 , R 1 and R 3 but generally fall in the range of 20°C-80°C.
  • R 1 , R 2 , R 3 , R and R" have the meaning given in Formula (1) and R' ' is chlorine or bromine.
  • This reaction involves the coupling of an aminophenol 15 with a 4-chloronitrobenzene 16 in the pr esence of a base to af f ord 4-ni trophenoxyaniline 17 as described in Schramm et al., Ann. , 740. 169 (1970). Reaction of the amino group in 17 with trif luoroacetic anhydride affords amide 18. Nitro group reduction. Sandmeyer halogenation and deprotection of the amino function afford aniline 19. The details of these transformations are given in the experimental section hereinbelow.
  • Suitable liquid diluents or carriers include water, petrolium distillates, or other liquid carriers with or without surface active agents.
  • Liquid concentrates may be prepared by dissolving one of these compounds with a nonphytotoxic solvent such as acetone, xylene, nitrobenzene, cyclohexanone or dimethyl formamide and dispersing the toxicants in water with the aid of suitable surface active emulsifying and dispersing agents.
  • dispersing and emulsifying agents and the amount employed is dictated by the nature of the composition and the ability of the agent to facilitate the dispersion of the toxicant. Generally, it is desirable to use as little of the agent as is possible, consistent with the desired dispersion of the toxicant in the spray so that rain does not re-emulsify the toxicant after it is applied to the plant and wash it off the plant.
  • Nonionic. anionic, or cationic dispersing and emulsifying agents may be employed, for example, the condensation products of alkylene oxides with phenol and organic acids, alkyl aryl sulfonates. complex ether alcohols, quaternary ammonium compounds, and the like.
  • the active ingredient is dispersed in and on an appropriately divided solid carrier such as clay, talc, bentonite, diatomaceous earth, fullers earth, and the like.
  • an appropriately divided solid carrier such as clay, talc, bentonite, diatomaceous earth, fullers earth, and the like.
  • the aforementioned dispersing agents as well as lignosulfonates can be included.
  • the required amount of the toxicants contemplated herein may be applied per acre treated in from 1 to 200 gallons or more of liquid carrier and/or diluent or in from about 5 to 500 pounds of inert solid carrier and/or diluent.
  • concentration in the liquid concentrate will usually vary from about 10 to 95 percent by weight and in the solid formulations from about 0.5 to about 90 percent by weight. Satisfactory sprays, dusts, or granules for general use contain from about 1/4 to 15 pounds of active toxicant per acre.
  • the pesticides contemplated herein prevent attack by insects upon plants or other material to which the pesticides are applied, and they have relatively high residual toxicity. With respect to plants, they have a high margin of safety in that when used in sufficient amount to kill or repel the insects, they do not burn or injure the plant, and they resist weathering which includes wash-off caused by rain, decomposition by ultraviolet light, oxidation, or hydrolysis in the presence of moisture or. at least, such decomposition, oxidation, and hydrolysis as would materially decrease the desirable pesticidal characteristic of the toxicants or impart undesirable characteristics, for instance, phytotoxicity, to the toxicants.
  • the toxicants are so chemically inert that they are now compatible with substantially any other constituents of the spray schedule, and they may be used in the soil, upon the seed, or the roots of plants without injuring either the seeds or roots of plants. Mixtures of the active compounds may be employed if desired as well as combinations of the active compounds of this invention with other biologically active compounds or ingredients.
  • reaction mixture was refluxed and stirred for 5.5 hours, allowed to cool, diluted with water and then extracted with toluene.
  • the mixture was stirred at ambient temperature for
  • Certain representative examples of the new compounds were evaluated to determine their pesticidal activity against certain insects, including a caterpillar and a beetle. The new compounds were also tested for phytotoxicity on important economic crops including snap bean, cucumber and sorghum. The new compounds were further evaluated for mammalian toxicity.
  • Suspensions of the test compounds were prepared by dissolving 100 milligrams of compound in 1.5 milliliters of dimethylforamide and then adding 8.5 milliliters of an acetone solution containing 0.25 percent of an alkylphenoxy polyethoxyethanol surfactant, as an emulsifying or dispersing agent. The resulting solution was mixed into 30 milliliters of water to give roughly 40 milliliters of a suspension containing the compound in finely divided form. The thus-prepared stock suspension contained 2.5 percent by weight of compound. The test concentrations in parts per million by weight employed in the tests described hereinbelow were obtained by appropriate dilutions of the stock suspension with water. Sonication was used where necessary to obtain a homogeneous suspension. The test procedures were as follows:
  • treated and dried cotton leaves were introduced into 9 cm Petri dishes which were organized in to groups of 10-dish sets. One randomly selected larvae was introduced into each dish of a ten dish set and the dishes were closed. The closed dishes were labelled and held at 80° ⁇ 5° F. for five days. Larvae which were unable to move the length of the body, even upon stimulation, were considered dead. Percent mortality was recorded for various concentration levels.

Landscapes

  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Nouveaux composés à base d'urée de 1-(4-phénoxyphényl)-3-benzoyle, ainsi que leurs procédés de préparation et l'utilisation desdits composés en tant qu'agent actif dans des compositions pesticides.
EP86901632A 1985-03-29 1986-02-20 Composes pesticides a base d'uree de 1-(4-phenoxyphenyl)-3-benzoyle, et procede de preparation Withdrawn EP0215056A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US71778585A 1985-03-29 1985-03-29
US717785 1985-03-29

Publications (1)

Publication Number Publication Date
EP0215056A1 true EP0215056A1 (fr) 1987-03-25

Family

ID=24883493

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86901632A Withdrawn EP0215056A1 (fr) 1985-03-29 1986-02-20 Composes pesticides a base d'uree de 1-(4-phenoxyphenyl)-3-benzoyle, et procede de preparation

Country Status (7)

Country Link
EP (1) EP0215056A1 (fr)
JP (1) JPS62502333A (fr)
AU (2) AU5455586A (fr)
BR (1) BR8606563A (fr)
FI (1) FI864873A0 (fr)
WO (1) WO1986005781A1 (fr)
ZA (1) ZA861766B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4965389A (en) * 1987-03-10 1990-10-23 Ciba-Geigy Corporation Phenoxyphenylthioureas phenoxyphenylisothioureas and phenoxyphenylcarbodiimides and use thereof for controlling pests
US5026730A (en) * 1987-08-21 1991-06-25 Ciba-Geigy Corporation Anilinophenylthioureas, compositions containing them, and the use thereof in pest control
DE3731561A1 (de) * 1987-09-19 1989-04-06 Basf Ag N-benzoyl-n'-(2,3-dichlor-4-phenoxy)phenyl- harnstoffe

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2531202C2 (de) * 1975-07-12 1982-12-09 Bayer Ag, 5090 Leverkusen 2',4-Dichlor-4'-benzoylureido- diphenyläther, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide
JPS5538357A (en) * 1978-09-13 1980-03-17 Ishihara Sangyo Kaisha Ltd Insecticide
DE3026825A1 (de) * 1980-07-16 1982-02-18 Basf Ag, 6700 Ludwigshafen Substituierte n-benzoyl-n'-phenoxyphenylharnstoffe, ihre herstellung, ihre verwendung zur bekaempfung von bekaempfung von insekten und mittel dafuer
DE3104407A1 (de) * 1981-02-07 1982-08-19 Basf Ag, 6700 Ludwigshafen N-benzoyl-n'-phenoxyphenylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen
CA1205483A (fr) * 1982-06-30 1986-06-03 David T. Chou 1-(alcoylphenoxyaryl)-3-benzoylurees pesticides et methode de preparation
SU1340569A3 (ru) * 1982-06-30 1987-09-23 Юнион Карбид Корпорейшн (Фирма) Инсектицидна композици
JPH08192857A (ja) * 1990-08-10 1996-07-30 Masayoshi Matsumoto 手提袋

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8605781A1 *

Also Published As

Publication number Publication date
BR8606563A (pt) 1987-08-04
FI864873A (fi) 1986-11-28
AU6191590A (en) 1991-01-03
FI864873A0 (fi) 1986-11-28
JPS62502333A (ja) 1987-09-10
AU5455586A (en) 1986-10-23
WO1986005781A1 (fr) 1986-10-09
ZA861766B (en) 1986-10-29

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Inventor name: CAIN, PAUL, ALFRED

Inventor name: CHOU, DAVID, TEH-WEI