Carbonyl, Sulfur, Or Cyano Attached Directly To Thiourea Nitrogen By Nonionic Bonding Patents (Class 564/23)
  • Patent number: 5096928
    Abstract: Insecticidal substituted benzoyl(thio) ureas of the formula ##STR1## in which Q stands for oxygen or sulphur,R.sup.1 stands for hydrogen, halogen, nitro, methyl or trifluoromethyl,R.sup.2 stands for hydrogen, fluorine or chlorine,R.sup.3 stands for hydrogen, fluorine or chlorine,R.sup.4 stands for hydrogen or fluorine,R.sup.5 stands for hydrogen or halogen andn stands for the numbers 2, 3 or 4.Intermediates of the formula ##STR2## are also new.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: March 17, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Albrecht Marhold, Benedikt Becker, Wilhelm Stendel
  • Patent number: 5001157
    Abstract: New substituted N-[[2-(aminocarbonyl)phenylamino]-thioxomethyl]benzamides which are useful as congnition stimulators in mammals.
    Type: Grant
    Filed: February 2, 1989
    Date of Patent: March 19, 1991
    Assignee: American Cyanamid Company
    Inventors: William J. Fanshawe, Joseph W. Epstein
  • Patent number: 4971994
    Abstract: Novel N-phenyl-N-carbonylthioureas of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.10 alkyl, phenyl-C.sub.1 -C.sub.7 alkyl; C.sub.1 -C.sub.10 alkyl or phenyl-C.sub.1 -C.sub.7 alkyl each of which is monohalogenated or polyhalogenated or interrupted once or more than once by oxygen and/or sulfur; C.sub.3 -C.sub.8 cycloalkyl; C hd 3-C.sub.8 cycloalkyl which is monosubstituted or polysubstituted by halogen or C.sub.1 -C.sub.5 alkyl; or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl,R.sub.2 is C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, phenyl, phenyl-C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.8 cycloalkyl; C.sub.1 14 C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl or phenyl-C.sub.1 -C.sub.7 alkyl each of which is monohalogenated or polyhalogenated or interrupted once or more than once by oxygen and/or sulfur; C.sub.3 -C.sub.8 cycloalkyl; phenyl or C.sub.3 -C.sub.8 cycloalkyl each of which is monosubstituted or polysubstituted by halogen or C.
    Type: Grant
    Filed: April 11, 1989
    Date of Patent: November 20, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Jozef Drabek, Manfred Boger, Josef Ehrenfreund
  • Patent number: 4954529
    Abstract: Compounds of the general formula I ##STR1## in which A denotes a radical of the formula A.sup.1, A.sup.2 or A.sup.3 ##STR2## R.sup.1 to R.sup.3 in each case independently of one another denote hydrogen or halogen,the radicals R.sup.4 in each case independently of one another denote halogen, (C.sub.1 -C.sub.3)halogenoalkyl or nitro,R.sup.5 denotes (C.sub.1 -C.sub.5)alkyl, which can be halogenated,X denotes oxygen or sulfur,n denotes a number from 0 to 2 andm denotes a number from 1 to 4 with the proviso that (R.sup.4).sub.m does not by itself denote halogen or by itself denote nitro, and where A=A.sup.1, salts thereof which can be used in agriculture, have advantageous acaricidal and insecticidal properties.Processes for the preparation of the compounds of the formula I are furthermore described.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: September 4, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Volker Koch, Stefan Schnatterer, Werner Bonin, Manfred Kern, Werner Knauf, Anna Waltersdorfer
  • Patent number: 4873264
    Abstract: Novel 1-(alkylphenoxyphenyl)-3-benzoyl ureas and a process for their preparation are provided. The novel ureas are useful as the active toxicant in pesticidal composition.
    Type: Grant
    Filed: March 7, 1988
    Date of Patent: October 10, 1989
    Assignee: Rhone-Poulenc Nederlands B.V.
    Inventors: David T. Chou, Paul A. Cain
  • Patent number: 4868215
    Abstract: N-aroyl N'-phenyl ureas having the formula ##STR1## wherein: Ar is a substituted phenyl, pyridyl or pyrimidinyl radical wherein the substituents are chloro, bromo, fluoro C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, with the proviso that at least one substituent is positioned ortho to the carbonyl group; R.sub.3 and R.sub.4 are individually H or C.sub.1 -C.sub.4 alkyl or together they form the group ##STR2## Y is O or S; X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are individually H, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, alkylcarbonyl, alkoxycarbonyl, C.sub.1 -C.sub.3 alkylthio, NO.sub.2, CN or NR.sub.5 R.sub.6 wherein R.sub.5 and R.sub.6 are H or C.sub.1 -C.sub.3 alkyl with the provisos that at least one of X.sub.1, X.sub.2, X.sub.3 or X.sub.4 is other than H and (a) when three of X.sub.1, X.sub.2, X.sub.3 or X.sub.4 are H, the fourth substitution cannot be halogen or alkyl, (b) when X.sub.1 and X.sub.3 are H, X.sub.2 and X.sub.4 cannot both be halogen, (c) when X.sub.2 and X.sub.
    Type: Grant
    Filed: September 24, 1984
    Date of Patent: September 19, 1989
    Assignee: The Dow Chemical Company
    Inventors: Barat Bisabri-Ershadi, Raymond H. Rigterink
  • 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: 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: 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: 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: 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: 4665097
    Abstract: Novel bicyclooxyaryl thioureas are provided together with methods for their preparation and use as the active toxicant in pesticidal compositions.
    Type: Grant
    Filed: March 31, 1983
    Date of Patent: May 12, 1987
    Assignee: Union Carbide Corporation
    Inventor: Paul A. Cain
  • 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: 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: 4613356
    Abstract: Substituted aryloxyphenoxy propionyl thiourea compounds useful as herbicides, and their methods of use, a representative one of which has the structural formula ##STR1## The method comprises applying the above referenced compound to the locus where control is desired.
    Type: Grant
    Filed: August 6, 1984
    Date of Patent: September 23, 1986
    Assignee: Stauffer Chemical Company
    Inventor: Ferenc M. Pallos
  • 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: 4571266
    Abstract: There is described a process for the separation and purification of the platinum group metals from base metal out of acidic aqueous solutions. For this purpose there is used a substituted thiourea of the formulaR.sub.1 R.sub.2 N--CS--NH--CO--R.sub.3orR.sub.1 R.sub.2 N--CS--NH--COOR.sub.3as the extraction agent. Preferably there are employed N,N-dialkyl-N'-benzoylthiourea wherein R.sub.1 and R.sub.2 are methyl, n-butyl, or n-hexyl.
    Type: Grant
    Filed: November 2, 1984
    Date of Patent: February 18, 1986
    Assignee: Degussa Aktiengesellschaft
    Inventors: Karl-Heinz Konig, Michael Schuster, Gerd Schneeweis, Bernd Steinbrech, Rainer Schlodder
  • Patent number: 4571265
    Abstract: There is described a process for the separation and purification of the platinum group metals from base metal out of acidic aqueous solutions. For this purpose there is used a substituted thiourea of the formulaR.sub.1 R.sub.2 N--CS--NH--CO--R.sub.3orR.sub.1 R.sub.2 N--CS--NH--COOR.sub.3as the precipitation agent. Preferably there are employed N,N-diaklyl-N'-benzoylthiourea wherein R.sub.1 and R.sub.2 are methyl, n-butyl, or n-hexyl.
    Type: Grant
    Filed: November 2, 1984
    Date of Patent: February 18, 1986
    Assignee: Degussa Aktiengesellschaft
    Inventors: Karl-Heinz Konig, Michael Schuster, Dieter Hollmann, Rainer Schlodder
  • Patent number: 4562210
    Abstract: Novel N-[2-(1,2-dichlorovinyloxy)phenylsulfonyl]-(thio)ureas of the general formula I ##STR1## in which X is oxygen or sulfur, R.sub.1 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkinyl; and R.sub.2 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkinyl or C.sub.1 -C.sub.6 -alkoxy; and the salts of these compounds are described.These compounds have pronounced bactericidal properties and can be used without problems against bacteria which damage plants, especially in the agricultural sector.
    Type: Grant
    Filed: December 21, 1983
    Date of Patent: December 31, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Willy Meyer, Werner Topfl, Haukur Kristinsson, Wolfgang Eckhardt
  • Patent number: 4560751
    Abstract: Compounds of the general formula I ##STR1## where R is unsubstituted or substituted alkyl, alkenyl, aryl or hetaryl and R.sup.1 and R.sup.2 independently of one another are each unsubstituted or substituted alkyl or aryl, or, together with the nitrogen, form a heterocyclic ring, are prepared by a process wherein a compound of the general formula II ##STR2## is reacted with a water-soluble monohaloacetate in an aqueous alkaline medium. They are very useful coupling components for the preparation of azo dyes.
    Type: Grant
    Filed: June 30, 1983
    Date of Patent: December 24, 1985
    Assignee: BASF Aktiengesellschaft
    Inventor: Guenther Seybold
  • 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: 4537620
    Abstract: Substituted aryloxyphenoxy acylisothioureas useful as herbicides having the formula ##STR1## wherein R is CF.sub.3 or halogen; X is hydrogen or halogen; A is CH or nitrogen; R.sub.1 is hydrogen, lower alkyl, alkenyl, alkynyl, phenyl, cyanoalkyl, alkoxyalkyl, or alkoxycarbonylalkyl; R.sub.2 is hydrogen, lower alkyl, phenyl, or substituted phenyl; and R.sub.3 is acyl or halogen substituted acyl selected from the group consisting of propionyl, dichloro bromoacetyl, propionaminocarbonyl and phenylaminocarbonyl.
    Type: Grant
    Filed: July 2, 1984
    Date of Patent: August 27, 1985
    Assignee: Stauffer Chemical Company
    Inventor: Ferenc M. Pallos
  • 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: 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: 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: 4321083
    Abstract: Compounds having the formula ##STR1## in which R is alkyl having 1-4 carbon atoms and have utility for the protection of crops from herbicidal injury.
    Type: Grant
    Filed: April 21, 1980
    Date of Patent: March 23, 1982
    Assignee: Stauffer Chemical Company
    Inventor: Ferenc M. Pallos
  • Patent number: 4288454
    Abstract: The present invention relates to 1-adamantyl-3-(phenylsulfonyl)thioureas of the formula ##STR1## wherein R is lower alkyl, amino or lower alkanoylamino to methods of preparation thereof and to their use in the treatment and prevention of viral infections in mammalian and avian hosts.
    Type: Grant
    Filed: December 13, 1979
    Date of Patent: September 8, 1981
    Assignee: Hoffman-La Roche Inc.
    Inventors: Michael J. Kramer, Jefferson W. Tilley
  • Patent number: 4276310
    Abstract: N-(4-Substituted-phenyl)-N'-(2-substituted-benzoyl)-thioureas of the formula ##STR1## in which R.sup.1 represents halogen,R.sup.2 represents hydrogen or halogen,R.sup.3 represents hydrogen, halogen or halogenoalkyl,R.sup.4 represents halogen, halogenoalkyl, halogenoalkoxy, halogenoalkylthio or halogenoalkylsulphonyl, with the proviso that R.sup.3 represents halogenoalkyl if R.sup.4 represents halogen, andR.sup.5 represents hydrogen or halogen,which possess arthropodicidal, fungicidal and bactericidal properties.
    Type: Grant
    Filed: August 16, 1979
    Date of Patent: June 30, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Erich Klauke, Ingeborg Hammann, Ingomar Krehan, Peter Kraus, Wilhelm Stendel
  • Patent number: 4233302
    Abstract: The invention relates to compounds of the general formula (I) ##STR1## and physiologically acceptable salts, N-oxides, hydrates and bioprecursors thereof, in whichY represents .dbd.O, .dbd.S, .dbd.CHNO.sub.2 or .dbd.NR.sub.3 where R.sub.3 represents hydrogen, nitro, cyano, lower alkyl, aryl, lower alkylsulphonyl or arylsulphonyl;R.sub.1 and R.sub.2, which may be the same or different, each represent hydrogen lower alkyl, cycloalkyl, lower alkenyl, aralkyl, hydroxy, lower trifluoroalkyl, lower alkyl substituted by hydroxy, lower alkoxy, amine, lower alkylamino or dialkylamino, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a 5 to 7 membered heterocyclic ring which may contain other heteroatoms or the group ##STR2## where R.sub.
    Type: Grant
    Filed: December 18, 1978
    Date of Patent: November 11, 1980
    Assignee: Glaxo Group Limited
    Inventors: Michael Martin-Smith, Barry J. Price, John Bradshaw, John W. Clitherow