Additional Carbonyl Bonded Directly To Urea Nitrogen Patents (Class 564/44)
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Patent number: 4861799Abstract: A benzoylurea compound having the formula: ##STR1## wherein each of X.sub.1 and X.sub.2 is a hydrogen atom, a halogen atom or a methyl group, provided that X.sub.1 and X.sub.2 are not simultaneously hydrogen atoms, Y is independently a hydrogen atom, a halogen atom, an alkyl group which may be substituted by halogen, a --CO.sub.2 R.sub.1 group wherein R.sub.1 is a hydrogen atom, a cation or an alkyl group, or a --OR.sub.1 group wherein R.sub.1 is as defined above, A.sub.1 is .dbd.N--or ##STR2## wherein Y is as defined above, W is an oxygen atom, a sulfur atom or ##STR3## wherein R.sub.1 is as defined above, k is an integer of from 1 to 3, l is 0 or 1, and Ar is ##STR4## wherein Z is independently a hydrogen atom, a halogen atom, an alkyl group which may be substituted by halogen, an alkoxy group which may be substituted by halogen, a nitro group, a cyano group or a --S(O).sub.n R.sub.2 group wherein R.sub.2 is an alkyl group which may be substituted by halogen and n is 0, 1 or 2, A.sub.Type: GrantFiled: September 30, 1987Date of Patent: August 29, 1989Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Takahiro Haga, Tadaaki Toki, Toru Koyanagi, Yasuhiro Fujii, Kiyomitsu Yoshida, Osamu Imai
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Patent number: 4843100Abstract: This invention relates to a benzoylurea derivative of the formula: ##STR1## wherein X.sup.1 and X.sup.2 are hydrogen, halogen, alkyl or alkoxy; and one of Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4 and Y.sup.5 is halogenoalkylsulfinyl or halogenoalkylsulfonyl, and the others are hydrogen, halogen or alkyl, exhibiting excellent insecticidal and ovicidal activities (particularly, molt inhibitory activity), their production and use.Type: GrantFiled: June 19, 1987Date of Patent: June 27, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroshi Nagase, Yasuo Sato
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Patent number: 4798837Abstract: The invention relates to novel substituted N-benzoyl-N'-2,5-dichloro-4-hexafluoropropyloxyphenylureas of the formula ##STR1## wherein R.sub.1 is hydrogen, fluorine, chlorine or methoxy, and R.sub.2 is fluorine, chlorine or methoxy, and to the salts thereof; to proesses and intermediates for the preparation of these compounds and to compositions containing the novel compounds for controlling insects and representatives of the order Acarina, in particular plant-destructive insects.Type: GrantFiled: June 4, 1987Date of Patent: January 17, 1989Assignee: Ciba-Geigy CorporationInventors: Jozef Drabek, Manfred Boger
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Patent number: 4783485Abstract: The invention relates to new benzoylurea compounds having insecticidal and acaricidal activity, of the general formula ##STR1## wherein R.sub.1 is a hydrogen atom or represents 1 or 2 halogen atoms;Ar is a para-phenylene group or a para-pyridylene group, which groups may be substituted with 1 or 2 substituents selected from the group consisting of chlorine, methyl and trifluoromethyl;B is an oxygen atom or represents a group having the formula ##STR2## wherein R.sub.Type: GrantFiled: September 26, 1986Date of Patent: November 8, 1988Assignee: Duphar International Research B.V.Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt, Roelof Van Hes
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Patent number: 4782090Abstract: Arthropodicidally active novel benzoyl(thio)ureas of the formula ##STR1## in which X is oxygen or sulphur, andR.sup.1 and R.sup.2 each independently is hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl.Type: GrantFiled: November 16, 1987Date of Patent: November 1, 1988Assignee: Bayer AktiengesellschaftInventors: Wilhelm Sirrenberg, Benedikt Becker, Wolfgang Behrenz, Ingomar Krehan, Wilhelm Stendel
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Patent number: 4782091Abstract: Arthropodicidally active novel benzoyl(thio)ureas of the formula ##STR1## in which X is oxygen or sulphur,R.sup.1 is halogen andR.sup.2 is halogen.Type: GrantFiled: November 10, 1987Date of Patent: November 1, 1988Assignee: Bayer AktiengesellschaftInventors: Wilhelm Sirrenberg, Benedikt Becker, Wolfgang Behrenz, Ingomar Krehen, Wilhelm Stendel
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Patent number: 4774260Abstract: 1-Phenyl-3-benzoyl-(thio)ureas of the formula ##STR1## in which X represents oxygen or sulphur,R.sup.1 represents hydrogen, halogen, nitro, alkyl or alkylthio,R.sup.2, R.sup.4 and R.sup.5 are identical or different and represent hydrogen or halogen,R.sup.3 represents hydrogen, halogen or nitro,R.sup.6 and R.sup.7 are identical or different and represent hydrogen, halogen or alkyl,R.sup.8 and R.sup.9 are identical or different and represent hydrogen or halogen andR.sup.10 represents halogenoalkylthio or halogenoalkoxy,with certain exclusions, which possess insecticidal and acaricidal activity.Type: GrantFiled: March 24, 1986Date of Patent: September 27, 1988Assignee: Bayer AktiengesellschaftInventors: Wilhelm Sirrenberg, Erich Klauke, Benedikt Becker, Ingomar Krehan, Wilhelm Stendel
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Patent number: 4737509Abstract: Compounds of the formula ##STR1## wherein Z is ##STR2## compositions containing the compounds, and their utility as dietary and foliar insecticides are disclosed and exemplified.Type: GrantFiled: December 4, 1986Date of Patent: April 12, 1988Assignee: FMC CorporationInventor: Ernest L. Plummer
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Patent number: 4734436Abstract: Disclosed is a compound of the formula: ##STR1## wherein X.sub.1 and X.sub.3 represent chloro or fluoro, X.sub.2 represents hydrogen, chloro or fluoro, X.sub.4 represents hydrogen or halogen, X.sub.5 represents --CF.sub.3 or --OCF.sub.3, Y represents oxygen or sulfur and an insecticidal composition containing said compound, a method for killing insect pests and a process for producing said compound and its use as pesticide.Type: GrantFiled: December 9, 1985Date of Patent: March 29, 1988Assignee: Nippon Kayaku Kabushiki KaishaInventors: Akira Kurozumi, Satoshi Ototake, Hitoshi Sato, Satoshi Tanabe, Tatsumi Hayaoka, Akio Masui
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Patent number: 4720450Abstract: A method of thermal imaging is provided which comprises heating imagewise a layer of a colored di- or triarylmethane compound possessing within its di- or triarylmethane structure an aryl group substituted in the ortho-position to the meso carbon atom with a group comprising a thermally unstable urea moiety which fragments upon heating to provide a new group that bonds to the meso carbon atom whereby the di- or triarylmethane compound is rendered ring-closed and colorless in an imagewise pattern corresponding to said imagewise heating.Type: GrantFiled: May 15, 1986Date of Patent: January 19, 1988Assignee: Polaroid CorporationInventor: Ernest W. Ellis
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Patent number: 4713396Abstract: A compound having the formula ##STR1## wherein R.sub.1 represents halogen or methyl;R.sub.2 represents hydrogen or halogen;each of R.sub.3 and R.sub.4 represents halogen; andeach of X and Y represents oxygen or sulfur.The compound is useful as insecticide.Type: GrantFiled: September 9, 1985Date of Patent: December 15, 1987Assignee: Nippon Soda Co., Ltd.Inventors: Katsuyata Ikura, Kenji Hagiwara, Fumihiko Nagasaki, Tomio Yamada, Hidemitsu Takahashi, Renpei Hatano
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Patent number: 4711905Abstract: A 2,4-dihalogenobenzoyl-(thio)urea of the formula ##STR1## in which X represents sulphur or oxygen,X.sup.1 and X.sup.2 are identical or different and represent fluorine, chlorine, bromine or iodine,R.sup.1 represents hydrogen, halogen or optionally substituted radicals from the series comprising alkyl, alkoxy and alkylthio,R.sup.2 represents hydrogen, halogen, cyano, nitro, or optionally substituted radicals from the series comprising alkyl, alkylthio, alkylsulphonyl, alkoxy, aryloxy, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl and alkoxycarbonylalkylthio, orR.sup.1 and R.sup.2 together represent an optionally substituted alkylenedioxy radical or --CF.sub.2 --O--CF.sub.2 --O--,R.sup.3 represents hydrogen, halogen or an optionally substituted alkyl, alkoxy or aryloxy radical, andR.sup.4 represents hydrogen, halogen, or optionally substituted radicals from the series comprising alkyl, alkylthio and alkoxy, with the exception of those cases in which X represents oxygen, X.sup.1 andX.sup.Type: GrantFiled: June 19, 1985Date of Patent: December 8, 1987Assignee: Bayer AktiengesellschaftInventors: Wilhelm Sirrenberg, Erich Klauke, Ingeborg Hammann, Wilhelm Stendel
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Patent number: 4698365Abstract: Compounds of the formula ##STR1## in which "halogen" represents chlorine or fluorine and n is zero, one, two or three, that have useful pesticidal activity.Type: GrantFiled: November 25, 1986Date of Patent: October 6, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Martin Anderson
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Patent number: 4672058Abstract: Disclosed herein are tolrestat amides and methods of preparation. The amides are new aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.Type: GrantFiled: June 10, 1985Date of Patent: June 9, 1987Assignee: American Home Products CorporationInventors: Francesco Bellini, Kazimir Sestanj, Michael Kraml
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Patent number: 4672059Abstract: Disclosed herein are tolrestat and oxotolrestat amides and methods of preparation. The amides are new aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.Type: GrantFiled: November 18, 1985Date of Patent: June 9, 1987Assignee: American Home Products CorporationInventors: Kazimir Sestanj, Eckhardt S. Ferdinandi
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Patent number: 4665235Abstract: The invention relates to new benzoylurea compounds of the general formula ##STR1## wherein R.sub.1 is a halogen atom,R.sub.2 is a hydrogen atom or a halogen atom,R.sub.3 is a hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of chlorine, methyl and trifluormethyl,R.sub.4 is a hydrogen atom or represents 1-3 substituents which are selected from the group consisting of halogen, and alkyl, alkoxy, haloalkyl and haloalkoxy, having 1-4 carbon atoms,X is N or CH,n is 0 or 1, andR.sub.5 is a hydrogen atom, an alkyl group having 1-6 carbon atoms, an alkenyl group having 2-6 carbon atoms, or a cycloalkyl group having 3-6 carbon atoms, with the proviso, that, if n is 0 and R.sub.5 is a hydrogen atom, R.sub.3 is a hydrogen atom.The compounds have an insecticidal and acaricidal activity. After having been processed to compositions, the compounds may be used for the control of insects and/or mites in a dosage of 1 to 5000 grams of active substance per hectare.Type: GrantFiled: January 19, 1984Date of Patent: May 12, 1987Assignee: Duphar International Research B.V.Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt
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Patent number: 4656193Abstract: The invention relates to new benzoylurea compounds of the general formula ##STR1## wherein R.sub.1 is a hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of halogen and alkyl and haloalkyl having 1-4 carbon atoms,R.sub.2 is a hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of chlorine, methyl and trifluoromethyl, andR.sub.3 is a hydrogen atom or represents 1-3 alkyl and/or alkenyl groups each having 1-6 and/or 2-6 carbon atoms respectively,or wherein R.sub.3 together with the cyclohexyl ring to which it is attached forms a bi- or polycyclic hydrocarbyl group having 8-14 carbon atoms and, if desired, substituted with 1-3 alkyl groups each having 1-4 carbon atoms.The compounds have an insecticidal and acaricidal activity. After having been processed to compositions, the compounds may be used for the control of insects and/or mites in a dosage from 1 to 5000 g of active substance per hectare.Type: GrantFiled: September 20, 1985Date of Patent: April 7, 1987Assignee: Duphar International Research B.V.Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt, Roelof van Hes
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Patent number: 4638088Abstract: Novel biphenylyloxy and biphenylylalkoxy aryl acyl urea compounds are provided together with methods for their preparation and the use of said compounds as the active toxicant in pesticidal compositions.Type: GrantFiled: November 15, 1984Date of Patent: January 20, 1987Assignee: Union Carbide CorporationInventors: David T. Chou, Robert C. Ligon
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Patent number: 4632938Abstract: New insecticidal or/and ovicidal benzoylurea derivatives of the formula: ##STR1## wherein X.sup.1 is hydrogen or halogen; X.sup.2 is halogen; Y.sup.1, Y.sup.2 and Y.sup.3 are hydrogen, halogen or alkyl, whereby at least one of Y.sup.1, Y.sup.2 and Y.sup.3 is other than hydrogen; and R is hydrogen or a group represented by the formula --CF.sub.a Z.sub.b H.sub.(3-a-b) wherein a and b are 0, 1, 2 or 3, with a+b.ltoreq.3 and Z is halogen, their production and use.Type: GrantFiled: February 27, 1985Date of Patent: December 30, 1986Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroshi Nagase, Yasuo Sato
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Patent number: 4622340Abstract: This invention relates to compounds of the formula ##STR1## Z' is chlorine or fluorine, with the proviso that Z' is chlorine when Q is the moiety of Formula III. The invention also relates to the preparation of the compounds, their use in controlling animal pests in plant protection, and pesticidal agents comprising the compounds as active ingredients.Type: GrantFiled: April 26, 1984Date of Patent: November 11, 1986Assignee: Celamerck GmbH & Co., KGInventors: Heinz-Manfred Becher, Ricarda Prokic-Immel, Walter Wirtz
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Patent number: 4602109Abstract: Novel phenoxyphenyl and phenoxypyridyl benzoyl ureas and a process for their preparation are provided. The novel ureas are useful as the active toxicant in pesticidal compositions.Type: GrantFiled: December 27, 1984Date of Patent: July 22, 1986Assignee: Union Carbide CorporationInventors: David T. Chou, John A. Durden, Themistocles D. J. D'Silva
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Patent number: 4596890Abstract: A benzoylurea compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom or a halogen atom, R.sub.2 is a halogen atom, R.sub.3 is a halogen atom or a lower alkyl group and R.sub.4 is a 3,5-difluorophenyl group, a pentafluorophenyl group or a pentachlorophenyl group, which is useful as an insecticidal agent.Type: GrantFiled: September 25, 1984Date of Patent: June 24, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Hirosi Kisida, Sumio Nishida, Toshihiko Yano
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Patent number: 4594352Abstract: There are described compounds of formula: ##STR1## in which one of R and R.sup.1 is F or Cl and the other is H, F or Cl;X is a 1,4-phenylene or pyridyl bound in positions 2 and 5, optionally substituted;Y is a phenyl, 2- or 3-pyridyl, optionally substituted.The compounds of formula I are endowed with a high insecticide activity which is mainly directed against insect larvae and eggs.Type: GrantFiled: April 19, 1984Date of Patent: June 10, 1986Assignee: Montedison S.p.A.Inventors: Pietro Massardo, Franco Bettarini, Gabriele Giovarruscio, Paolo Piccardi, Franca Reggiori, Vincenzo Caprioli, Angelo Longoni
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Patent number: 4594451Abstract: There are described compounds of formula: ##STR1## in which X (or X')=H, F, Cl and X' (or X)=F, Cl; ##STR2## with R.sup.2 =H, Cl, Br, F an optionally halogen-substituted alkyl C.sub.1 -C.sub.3 ;R.sup.3 =halogen, an optionally halogen-substituted alkyl C.sub.1 -C.sub.3 ;R.sup.4 =H or R.sup.3 ;R.sup.1 =H, halogen, an optionally halogen-substituted alkyl C.sub.1 -C.sub.3, OCH.sub.3, SCH.sub.3, OCF.sub.3 ;n=an integer from 1 to 4.The compounds of formula I are endowed with a high insecticide activity which is mainly exerted against insects' larvae and eggs.Type: GrantFiled: April 19, 1984Date of Patent: June 10, 1986Assignee: Montedison S.p.A.Inventors: Pietro Massardo, Franco Bettarini, Gabriele Giovarruscio, Paolo Piccardi, Franca Reggiori, Vincenzo Caprioli, Angelo Longoni
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Patent number: 4567295Abstract: The invention relates to a composition active against mites, whitefly and thrips, which comprises, in addition to a liquid or solid inert carrier material, a benzoylurea compound of the general formula ##STR1## wherein R.sub.1 is hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of chlorine, methyl and trifluoromethyl,R.sub.2 is an alkyl group having 2-4 carbon atoms or a cycloalkyl group having 3 or 4 carbon atoms,R.sub.3 is a hydrogen atom or represents 1-3 substituents which are selected from the group consisting of halogen, and alkyl, alkoxy, haloalkyl and haloalkoxy having 1-4 carbon atoms,R.sub.4 and R.sub.5 are both fluorine atoms, or whereinR.sub.4 is a chlorine atom and R.sub.5 is a hydrogen atom, andX is an oxygen or sulphur atom.The composition may be used in a dosage of 10 to 5000 g of active substance per hectare.The invention further relates to pharmaceutical compositions comprising the above compounds.Type: GrantFiled: January 19, 1984Date of Patent: January 28, 1986Assignee: Duphar International Research B.V.Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt
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Patent number: 4564639Abstract: A urea derivative of the general formula, ##STR1## (wherein X is a halogen), which has higher insecticidal activity than known similar compounds, with lowered toxicity to mammals and fishes. The derivative can be produced by reacting 2-fluoro-4-haloaniline with 2,6-difluorobenzoyl isocyanate or reacting 2-fluoro-4-halo-phenylisocyanate with 2,6-difluorobenzamide.Type: GrantFiled: March 1, 1983Date of Patent: January 14, 1986Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroshi Nagase, Yasuo Sato
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Patent number: 4550202Abstract: The invention relates to new benzoylurea compounds of the general formula ##STR1## wherein R.sub.1 is a halogen atom,R.sub.2 is a hydrogen atom or a halogen atom,R.sub.3 is a hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of chlorine, methyl and trifluoromethyl,R.sub.4 is a hydrogen atom, an alkyl group having 1-6 carbon atoms or a cycloalkyl group having 3-6 carbon atoms,R.sub.5 is a hydrogen atom or an alkyl group having 1-4 carbon atoms, andA is a phenyl group or a heteroaryl group having 1 or 2 nitrogen atoms, which groups may be substituted with 1-3 substituents which are selected from the group consisting of halogen, and alkyl, alkoxy, haloalkyl and haloalkoxy having 1-4 carbon atoms.The compounds have an insecticidal and acaricidal activity. After having been processed to compositions, the compounds may be used for control of insects and/or mites in a dosage from 1 to 5000 g of active substance per hectare.Type: GrantFiled: January 19, 1984Date of Patent: October 29, 1985Assignee: Duphar International Research B.V.Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt
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Patent number: 4547524Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as herein defined useful as insecticides, is described.Type: GrantFiled: February 14, 1983Date of Patent: October 15, 1985Assignee: Hokko Chemical Industry Co., Ltd.Inventors: Kimiyoshi Kaneko, Hiromichi Ishikawa, Satoru Moriyama, Tsugio Uchiyama
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Patent number: 4533676Abstract: A 2,5-dihalogenobenzoyl-(thio)urea of the formula ##STR1## in which X represents sulphur or oxygen,X.sup.1 and X.sup.2 are identical or different and represent fluorine, chlorine, bromine or iodine,R.sup.1 represents hydrogen, halogen, or optionally substituted radicals from the series comprising alkyl, alkoxy and alkylthio,R.sup.2 represents hydrogen, halogen, cyano, nitro or optionally substituted radicals from the series comprising alkyl, alkylthio, alkylsulphonyl, alkoxy, aryloxy, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl and alkoxycarbonylalkylthio,R.sup.1 and R.sup.2 together represent an optionally substituted alkylenedioxy radical or represent --CF.sub.2 --O--CF.sub.2 --O--,R.sup.3 represents hydrogen, halogen, or an optionally substituted alkyl, alkoxy or aryloxy radical, andR.sup.4 represents hydrogen, halogen, or optionally substituted radicals from the series comprising alkyl, alkylthio and alkoxy, with the exception of those cases in which X represents oxygen, X.sup.1 and X.sup.Type: GrantFiled: April 22, 1983Date of Patent: August 6, 1985Assignee: Bayer AktiengesellschaftInventors: Wilhelm Sirrenberg, Erich Klauke, Ingeborg Hammann
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Patent number: 4529819Abstract: A process for preparing a benzoylphenylurea which comprises reacting a benzoyl chloride with an alkali metal cyanate in the presence of a catalyst and an inert solvent to prepare a benzoyl isocyanate which is treated in situ with an appropriate aniline compound.Type: GrantFiled: June 21, 1984Date of Patent: July 16, 1985Assignee: The Dow Chemical CompanyInventors: David P. Clifford, Robert A. Sewell
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Patent number: 4508734Abstract: N-benzoyl-N'-phenoxyphenylureas of the formula ##STR1## where X, Y and R have the meanings given in the disclosure. The compounds are suitable as adulticides and ovicides for combating insects.Type: GrantFiled: June 29, 1981Date of Patent: April 2, 1985Assignee: BASF AktiengesellschaftInventors: Arno Lange, Karl Kiehs, Heinrich Adolphi
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Patent number: 4505931Abstract: Novel N-(4-alkenylthio)-phenyl-N'-benzoylureas of the formula ##STR1## wherein R.sub.1 is a C.sub.3 -alkenyl group, or a C.sub.3 -alkenyl group which is mono- or disubstituted with chlorine or bromine, R.sub.2 and R.sub.3 independently of one another are each hydrogen or chlorine, R.sub.4 is hydrogen, fluorine or chlorine, and R.sub.5 is fluorine or chlorine; processes for producing these compounds, and also compositions containing the compounds, for use in combating pests, particularly in combating insect pests in the field of plant protection, and combating ectoparasites. The compounds have high ovicidal activity.Type: GrantFiled: January 24, 1980Date of Patent: March 19, 1985Assignee: Ciba-Geigy CorporationInventor: Josef Ehrenfreund
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Patent number: 4472434Abstract: New acyl urea of the general formula ##STR1## in which R.sub.1 is halogen or C.sub.1 -C.sub.6 -alkyl,R.sub.2 is hydrogen or halogen,R.sub.3 is hydrogen, halogen or methyl,R.sub.4 is hydrogen, halogen or methyl, andR.sub.5, R.sub.6 and R.sub.7 are the same or different and are hydrogen, C.sub.1 -C.sub.6 -alkyl or aryl,insecticidal agents containing these compounds as well as methods for their production. The compounds are effective in particular for the control of insect pests belonging to the classes Diptera, Coleoptera, as well as Lepidoptera.Type: GrantFiled: November 30, 1981Date of Patent: September 18, 1984Assignee: Schering AktiengesellschaftInventors: Heinrich Franke, Hartmut Joppien
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Patent number: 4468405Abstract: Novel N-aroyl N'-phenyl ureas having halogen substituents in the 3- and 5-positions and haloalkyl, haloalkoxy or haloalkylthio in the 4-position of the N'-phenyl are more active and have a broader spectrum of effectiveness than the known benzoylurea insecticides.Type: GrantFiled: July 26, 1982Date of Patent: August 28, 1984Assignee: The Dow Chemical CompanyInventors: Raymond H. Rigterink, Ronald J. Sbragia
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Patent number: 4457943Abstract: This invention relates to compounds of the formula ##STR1## wherein ##STR2## X is oxygen or sulfur; Y is chlorine or fluorine; andZ is hydrogen, chlorine, or fluorine,as well as to the preparation thereof, their use in controlling animal pests in plant protection, and pesticidal agents comprising the compounds of Formula I as active ingredients.Type: GrantFiled: November 16, 1981Date of Patent: July 3, 1984Assignee: Celamerck GmbH & Co. KGInventors: Heinz-Manfred Becher, Ricarda Prokic-Immel, Walter Wirtz
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Patent number: 4452631Abstract: Novel 1-(2,6-dialkoxybenzoyl)-3-(substituted phenyl)ureas are disclosed in the present invention. These compounds are useful both alone and in combination with other herbicides for controlling the growth of undesired plants.Type: GrantFiled: April 8, 1982Date of Patent: June 5, 1984Assignee: Eli Lilly and CompanyInventors: Kenneth W. Burow, Jr., George W. Johnson
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Patent number: 4440928Abstract: Uracil or 5-alkyluracil is prepared by a process wherein a 3,3-dialkoxypropionic acid ester of the formula:(R.sup.2 O).sub.2 CHCH(R.sup.1)COOR.sup.3wherein R.sup.1 =H or (C.sub.1-6) alkyl, and R.sup.2 and R.sup.3 are (C.sub.1-8) alkyl or (C.sub.7-9) aralkyl, is reacted with urea in liquid ammonia in the presence of an alkali metal amide, and then, the reaction product is cyclized in the presence of an acid catalyst.Type: GrantFiled: August 25, 1982Date of Patent: April 3, 1984Assignee: Ube Industries, Ltd.Inventors: Kanenobu Matsui, Shinichiro Uchiumi, Hideki Asada, Takashi Umezu
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Patent number: 4431671Abstract: Substituted N-(p-aminophenyl)-N'-benzoylureas of the formula ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl or propargyl; R.sub.2 and R.sub.3 are each hydrogen or halogen; R.sub.4 is methyl or halogen; and R.sub.5 is hydrogen or halogen. Processes for producing these compounds and their use for combating pests, particularly their use as insecticides, are described.Type: GrantFiled: December 3, 1981Date of Patent: February 14, 1984Assignee: Ciba-Geigy CorporationInventor: Josef Ehrenfreund
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Patent number: 4426385Abstract: Novel bicyclooxyphenyl ureas, such as 1-(bicyclooxyphenyl)-benzoyl ureas, are provided which exhibit pesticidal activity. The compositions are conveniently prepared by reacting an isocyanate with either an amide or a bicyclooxyaniline.Type: GrantFiled: September 28, 1981Date of Patent: January 17, 1984Assignee: Union Carbide CorporationInventor: Paul A. Cain
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Patent number: 4409015Abstract: A two stage process for preparing an aqueous dispersion of a urea-formaldehyde condensation product comprising: in a first stage, reacting together formaldehyde and urea in a molar ratio of formaldehyde to urea in the ratio from about 2.5 to 1 to about 4.7 to 1 in the presence of a condensation catalyst until the methanol tolerance is in a range such that the condensate is clear and will remain clear, substantially free from precipitated reaction material, upon storage for one year at room temperature, to form an intermediate reaction product, then in a second stage, reacting said intermediate reaction product with an additional amount of urea such that the overall molar ratio of urea to formaldehyde is in the range from 0.8 to 1 to about 1.7 to 1, at an acid pH and at an elevated temperature not above about 70.degree.C., until the amount of water insoluble nitrogen present in the reaction mixture is in the range from about 15% to about 35% based on the total amount of nitrogen in the system.Type: GrantFiled: February 11, 1982Date of Patent: October 11, 1983Assignee: Borden, Inc.Inventor: Thomas T. Grace, Jr.
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Patent number: 4399152Abstract: The invention relates to new benzoyl ureas of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hereafter defined. The invention also includes insecticidal compositions and the use thereof which contain the above compounds.Type: GrantFiled: December 14, 1981Date of Patent: August 16, 1983Assignee: Duphar International B.V.Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt
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Patent number: 4388312Abstract: New quinone derivatives of the formula: ##STR1## wherein R.sup.1 is methyl or methoxy, or two of R.sup.1 combine to represent --CH.dbd.CH--CH.dbd.CH--, R is amino which may be substituted or --OR.sup.4 wherein R.sup.4 is hydrogen, C.sub.1-4 alkyl or --CH.sub.2 --CH.dbd.C(CH.sub.3 --CH.sub.2 --.sub.m H (wherein m is an integer of 1 to 10), and n is an integer of 1 to 10 when R is amino which may be substituted, or n is an integer of 2 to 10 when R is --OR.sup.4, and their hydroquinone forms, have useful physiological activities such as blood-pressure decreasing and antiallergic activities.Type: GrantFiled: August 26, 1980Date of Patent: June 14, 1983Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Mitsuru Shiraishi, Kaneyoshi Kato
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Patent number: 4366317Abstract: This invention provides an improved process for synthesizing carboxamides which involves reacting 3-p-menthyl halide with magnesium to form 3-p-menthylmagnesium halide Grignard reagent, and reacting the Grignard reagent with hydrocarbyl isocyanate at a temperature below about -20.degree. C. to form N-hydrocarbyl-p-menthane-3-carboxamide product.The product comprises a mixture of geometric isomers in which the 3-p-menthyl:3-p-neomenthyl weight ratio is at least 4:1 and can be as high as 9:1 under optimal conditions.This invention also provides a novel process for producing acylurea compounds such as N-(3-p-menthylcarbonyl)-N-t-butyl-N'-t-butylurea.Type: GrantFiled: June 22, 1981Date of Patent: December 28, 1982Assignee: Philip Morris IncorporatedInventors: Stephen A. Haut, Roger A. Comes
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Patent number: 4355178Abstract: The invention relates to a process for the preparation of acyl ureas of formula (I) ##STR1## wherein R.sub.1 and R.sub.2 are the same of different and each is halogen atom, preferably fluorine or chlorine atom, andR.sub.3 is a substituted aryl group.The compounds of the invention can be prepared by reacting an urea of formula (II):R.sub.3 NHCONH.sub.2 (II)wherein R.sub.3 is as defined above, with an acid chloride of formula (III): ##STR2## wherein R.sub.1 and R.sub.2 are as defined above, in an inert organic solvent at a temperature of from 20.degree. C. to 100.degree. C.Type: GrantFiled: October 17, 1980Date of Patent: October 19, 1982Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.Inventors: Laszio Toke, Istvan Bitter, Eva Karpati nee Adam, Todor Pfliegel
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Patent number: 4353925Abstract: Novel substituted N-(p-aminophenyl)-N'-benzoylureas of the formula I ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -alkenyl, C.sub.3 -alkenyl substituted by a chlorine or bromine atom, or R.sub.1 is C.sub.3 -C.sub.6 -cycloalkyl, R.sub.2 and R.sub.3 are each hydrogen or halogen, R.sub.4 is methyl or halogen, R.sub.5 is hydrogen or halogen, and X is chlorine or bromine, the salts of these compounds, processes for producing these compounds, as well as compositions containing them, for use in combating pests, particularly for combating insects which infest plants and animals. The novel compounds are especially effective against larval stages and eggs of insects which damage plants by eating.Type: GrantFiled: July 9, 1981Date of Patent: October 12, 1982Assignee: Ciba-Geigy CorporationInventor: Josef Ehrenfreund
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Patent number: 4350706Abstract: The invention relates to new urea and thiourea compounds as insecticides.The compounds, after having been processed to compositions, can successfully be used to control insects in a dosage from 10 to 5000 g of active substance per hectare.Type: GrantFiled: June 27, 1979Date of Patent: September 21, 1982Assignee: Duphar International Research B.V.Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt
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Patent number: 4348412Abstract: Novel halogen-substituted N-(3-trifluoromethyl-4-halogenoalkoxyphenyl)-N'-benzoylureas of the formula ##STR1## wherein R.sub.1 is a C.sub.1 -C.sub.4 -alkyl group which is substituted at least twice by fluorine, chlorine or bromine, R.sub.2 is fluorine or chlorine, and R.sub.3 is hydrogen, fluorine or chlorine; processes for producing these compounds, as well as compositions containing them, for use in combating pests, particularly for combating insects which infest plants and animals. The novel compounds are especially effective against larval stages of insects which damage plants by eating.Type: GrantFiled: July 7, 1980Date of Patent: September 7, 1982Assignee: Ciba-Geigy CorporationInventor: Josef Ehrenfreund
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Patent number: 4339460Abstract: Novel substituted N-4-(3-bromoallyloxy)-phenyl-N'-benzoylureas of the formula ##STR1## wherein R.sub.1 and R.sub.2 independently of one another are each hydrogen, chlorine or bromine, R.sub.3 is fluorine or chlorine, and R.sub.4 is hydrogen, fluorine or chlorine; processes for producing these compounds, as well as compositions containing them, for use in combating pests, particularly in combating insects which infest plants and animals. The novel compounds have a strong toxic and/or development-inhibiting action in particular against larval stages of insects which damage plants.Type: GrantFiled: January 24, 1980Date of Patent: July 13, 1982Assignee: Ciba-Geigy CorporationInventor: Josef Ehrenfreund
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Patent number: 4332724Abstract: There is provided a process for the preparation of an amido or an ureido derivative of certain 4,5,6,7-tetrahydro-7-oxobenzo[b]thiophenes or certain 1,2,3,4-tetrahydro-4-oxonaphthalenes which can be employed as an animal growth regulant. The process comprises: oxidizing in the presence of a cobalt catalyst a compound having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each a substituent selected from the group consisting of alkanoyl C.sub.1 -C.sub.7, halogen-substituted alkanoyl C.sub.1 -C.sub.7, carboalkoxy C.sub.1 -C.sub.4, ##STR2## and ##STR3## R.sub.3 is selected from the group consisting of hydrogen and alkyl C.sub.1 -C.sub.4 ; R.sub.4 is selected from the group consisting of hydr ogen, alkyl C.sub.1 -C.sub.8, alkanoyl C.sub.2 -C.sub.4, halogen-substituted alkanoyl (C.sub.2 -C.sub.Type: GrantFiled: November 16, 1977Date of Patent: June 1, 1982Assignee: American Cyanamid Co.Inventors: Terence J. Bentley, William H. Gastrock, Goro Asato
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Patent number: RE32418Abstract: Novel alkoxy or alkylthio substituted(((phenyl)amino)carbonyl)-benzamides are disclosed. The compounds of the instant invention are useful as insecticides and can be formulated to provide insecticidal compositions.Type: GrantFiled: February 10, 1981Date of Patent: May 12, 1987Assignee: The Dow Chemical CompanyInventor: Raymond H. Rigterink