Additional Carbonyl Bonded Directly To Urea Nitrogen Patents (Class 564/44)
  • Patent number: 4861799
    Abstract: 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: Grant
    Filed: September 30, 1987
    Date of Patent: August 29, 1989
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Takahiro Haga, Tadaaki Toki, Toru Koyanagi, Yasuhiro Fujii, Kiyomitsu Yoshida, Osamu Imai
  • Patent number: 4843100
    Abstract: 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: Grant
    Filed: June 19, 1987
    Date of Patent: June 27, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroshi Nagase, Yasuo Sato
  • Patent number: 4798837
    Abstract: 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: Grant
    Filed: June 4, 1987
    Date of Patent: January 17, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Jozef Drabek, Manfred Boger
  • Patent number: 4783485
    Abstract: 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: Grant
    Filed: September 26, 1986
    Date of Patent: November 8, 1988
    Assignee: Duphar International Research B.V.
    Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt, Roelof Van Hes
  • Patent number: 4782090
    Abstract: 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: Grant
    Filed: November 16, 1987
    Date of Patent: November 1, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Benedikt Becker, Wolfgang Behrenz, Ingomar Krehan, Wilhelm Stendel
  • Patent number: 4782091
    Abstract: 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: Grant
    Filed: November 10, 1987
    Date of Patent: November 1, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Benedikt Becker, Wolfgang Behrenz, Ingomar Krehen, Wilhelm Stendel
  • Patent number: 4774260
    Abstract: 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: Grant
    Filed: March 24, 1986
    Date of Patent: September 27, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Erich Klauke, Benedikt Becker, Ingomar Krehan, Wilhelm Stendel
  • Patent number: 4737509
    Abstract: 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: Grant
    Filed: December 4, 1986
    Date of Patent: April 12, 1988
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4734436
    Abstract: 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: Grant
    Filed: December 9, 1985
    Date of Patent: March 29, 1988
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Akira Kurozumi, Satoshi Ototake, Hitoshi Sato, Satoshi Tanabe, Tatsumi Hayaoka, Akio Masui
  • Patent number: 4720450
    Abstract: 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: Grant
    Filed: May 15, 1986
    Date of Patent: January 19, 1988
    Assignee: Polaroid Corporation
    Inventor: Ernest W. Ellis
  • Patent number: 4713396
    Abstract: 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: Grant
    Filed: September 9, 1985
    Date of Patent: December 15, 1987
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Katsuyata Ikura, Kenji Hagiwara, Fumihiko Nagasaki, Tomio Yamada, Hidemitsu Takahashi, Renpei Hatano
  • Patent number: 4711905
    Abstract: 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: Grant
    Filed: June 19, 1985
    Date of Patent: December 8, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Erich Klauke, Ingeborg Hammann, Wilhelm Stendel
  • Patent number: 4698365
    Abstract: 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: Grant
    Filed: November 25, 1986
    Date of Patent: October 6, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Martin Anderson
  • Patent number: 4672058
    Abstract: 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: Grant
    Filed: June 10, 1985
    Date of Patent: June 9, 1987
    Assignee: American Home Products Corporation
    Inventors: Francesco Bellini, Kazimir Sestanj, Michael Kraml
  • Patent number: 4672059
    Abstract: 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: Grant
    Filed: November 18, 1985
    Date of Patent: June 9, 1987
    Assignee: American Home Products Corporation
    Inventors: Kazimir Sestanj, Eckhardt S. Ferdinandi
  • Patent number: 4665235
    Abstract: 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: Grant
    Filed: January 19, 1984
    Date of Patent: May 12, 1987
    Assignee: Duphar International Research B.V.
    Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt
  • Patent number: 4656193
    Abstract: 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: Grant
    Filed: September 20, 1985
    Date of Patent: April 7, 1987
    Assignee: Duphar International Research B.V.
    Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt, Roelof van Hes
  • Patent number: 4638088
    Abstract: 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: Grant
    Filed: November 15, 1984
    Date of Patent: January 20, 1987
    Assignee: Union Carbide Corporation
    Inventors: David T. Chou, Robert C. Ligon
  • Patent number: 4632938
    Abstract: 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: Grant
    Filed: February 27, 1985
    Date of Patent: December 30, 1986
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroshi Nagase, Yasuo Sato
  • Patent number: 4622340
    Abstract: 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: Grant
    Filed: April 26, 1984
    Date of Patent: November 11, 1986
    Assignee: Celamerck GmbH & Co., KG
    Inventors: Heinz-Manfred Becher, Ricarda Prokic-Immel, Walter Wirtz
  • Patent number: 4602109
    Abstract: 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: Grant
    Filed: December 27, 1984
    Date of Patent: July 22, 1986
    Assignee: Union Carbide Corporation
    Inventors: David T. Chou, John A. Durden, Themistocles D. J. D'Silva
  • Patent number: 4596890
    Abstract: 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: Grant
    Filed: September 25, 1984
    Date of Patent: June 24, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hirosi Kisida, Sumio Nishida, Toshihiko Yano
  • Patent number: 4594352
    Abstract: 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: Grant
    Filed: April 19, 1984
    Date of Patent: June 10, 1986
    Assignee: Montedison S.p.A.
    Inventors: Pietro Massardo, Franco Bettarini, Gabriele Giovarruscio, Paolo Piccardi, Franca Reggiori, Vincenzo Caprioli, Angelo Longoni
  • Patent number: 4594451
    Abstract: 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: Grant
    Filed: April 19, 1984
    Date of Patent: June 10, 1986
    Assignee: Montedison S.p.A.
    Inventors: Pietro Massardo, Franco Bettarini, Gabriele Giovarruscio, Paolo Piccardi, Franca Reggiori, Vincenzo Caprioli, Angelo Longoni
  • Patent number: 4567295
    Abstract: 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: Grant
    Filed: January 19, 1984
    Date of Patent: January 28, 1986
    Assignee: Duphar International Research B.V.
    Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt
  • Patent number: 4564639
    Abstract: 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: Grant
    Filed: March 1, 1983
    Date of Patent: January 14, 1986
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroshi Nagase, Yasuo Sato
  • Patent number: 4550202
    Abstract: 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: Grant
    Filed: January 19, 1984
    Date of Patent: October 29, 1985
    Assignee: Duphar International Research B.V.
    Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt
  • Patent number: 4547524
    Abstract: 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: Grant
    Filed: February 14, 1983
    Date of Patent: October 15, 1985
    Assignee: Hokko Chemical Industry Co., Ltd.
    Inventors: Kimiyoshi Kaneko, Hiromichi Ishikawa, Satoru Moriyama, Tsugio Uchiyama
  • Patent number: 4533676
    Abstract: 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: Grant
    Filed: April 22, 1983
    Date of Patent: August 6, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Erich Klauke, Ingeborg Hammann
  • Patent number: 4529819
    Abstract: 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: Grant
    Filed: June 21, 1984
    Date of Patent: July 16, 1985
    Assignee: The Dow Chemical Company
    Inventors: David P. Clifford, Robert A. Sewell
  • Patent number: 4508734
    Abstract: 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: Grant
    Filed: June 29, 1981
    Date of Patent: April 2, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Arno Lange, Karl Kiehs, Heinrich Adolphi
  • Patent number: 4505931
    Abstract: 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: Grant
    Filed: January 24, 1980
    Date of Patent: March 19, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Josef Ehrenfreund
  • Patent number: 4472434
    Abstract: 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: Grant
    Filed: November 30, 1981
    Date of Patent: September 18, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Heinrich Franke, Hartmut Joppien
  • Patent number: 4468405
    Abstract: 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: Grant
    Filed: July 26, 1982
    Date of Patent: August 28, 1984
    Assignee: The Dow Chemical Company
    Inventors: Raymond H. Rigterink, Ronald J. Sbragia
  • Patent number: 4457943
    Abstract: 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: Grant
    Filed: November 16, 1981
    Date of Patent: July 3, 1984
    Assignee: Celamerck GmbH & Co. KG
    Inventors: Heinz-Manfred Becher, Ricarda Prokic-Immel, Walter Wirtz
  • Patent number: 4452631
    Abstract: 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: Grant
    Filed: April 8, 1982
    Date of Patent: June 5, 1984
    Assignee: Eli Lilly and Company
    Inventors: Kenneth W. Burow, Jr., George W. Johnson
  • Patent number: 4440928
    Abstract: 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: Grant
    Filed: August 25, 1982
    Date of Patent: April 3, 1984
    Assignee: Ube Industries, Ltd.
    Inventors: Kanenobu Matsui, Shinichiro Uchiumi, Hideki Asada, Takashi Umezu
  • Patent number: 4431671
    Abstract: 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: Grant
    Filed: December 3, 1981
    Date of Patent: February 14, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Josef Ehrenfreund
  • Patent number: 4426385
    Abstract: 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: Grant
    Filed: September 28, 1981
    Date of Patent: January 17, 1984
    Assignee: Union Carbide Corporation
    Inventor: Paul A. Cain
  • Patent number: 4409015
    Abstract: 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: Grant
    Filed: February 11, 1982
    Date of Patent: October 11, 1983
    Assignee: Borden, Inc.
    Inventor: Thomas T. Grace, Jr.
  • Patent number: 4399152
    Abstract: 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: Grant
    Filed: December 14, 1981
    Date of Patent: August 16, 1983
    Assignee: Duphar International B.V.
    Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt
  • Patent number: 4388312
    Abstract: 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: Grant
    Filed: August 26, 1980
    Date of Patent: June 14, 1983
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Mitsuru Shiraishi, Kaneyoshi Kato
  • Patent number: 4366317
    Abstract: 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: Grant
    Filed: June 22, 1981
    Date of Patent: December 28, 1982
    Assignee: Philip Morris Incorporated
    Inventors: Stephen A. Haut, Roger A. Comes
  • Patent number: 4355178
    Abstract: 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: Grant
    Filed: October 17, 1980
    Date of Patent: October 19, 1982
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.
    Inventors: Laszio Toke, Istvan Bitter, Eva Karpati nee Adam, Todor Pfliegel
  • Patent number: 4353925
    Abstract: 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: Grant
    Filed: July 9, 1981
    Date of Patent: October 12, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Josef Ehrenfreund
  • Patent number: 4350706
    Abstract: 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: Grant
    Filed: June 27, 1979
    Date of Patent: September 21, 1982
    Assignee: Duphar International Research B.V.
    Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt
  • Patent number: 4348412
    Abstract: 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: Grant
    Filed: July 7, 1980
    Date of Patent: September 7, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Josef Ehrenfreund
  • Patent number: 4339460
    Abstract: 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: Grant
    Filed: January 24, 1980
    Date of Patent: July 13, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Josef Ehrenfreund
  • Patent number: 4332724
    Abstract: 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: Grant
    Filed: November 16, 1977
    Date of Patent: June 1, 1982
    Assignee: American Cyanamid Co.
    Inventors: Terence J. Bentley, William H. Gastrock, Goro Asato
  • Patent number: RE32418
    Abstract: 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: Grant
    Filed: February 10, 1981
    Date of Patent: May 12, 1987
    Assignee: The Dow Chemical Company
    Inventor: Raymond H. Rigterink