Phosphorus Attached Directly Or Indirectly To Morpholine Ring By Nonionic Bonding Patents (Class 544/157)
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Patent number: 4562185Abstract: The present invention relates to combating pests with five-membered nitrogen-containing heterocyclic compounds of the formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, X and Y have the meaning given in the description. Many of the compounds are new.Type: GrantFiled: March 15, 1984Date of Patent: December 31, 1985Assignee: Bayer AktiengesellschaftInventors: Gerhard Jager, Rudolf Fauss, Kurt Findeisen, Benedikt Becker, Bernhard Homeyer
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Patent number: 4552870Abstract: Compounds and compositions containing them, for insecticidal control having the formula ##STR1## in which R.sub.1 is an alkyl group having from 1 to 3 carbon atoms, R.sub.2 is an alkyl group having from 1 to 6 carbon atoms, and R.sub.3 and R.sub.4 are independently alkyl groups having from 1 to 6 carbon atoms, or R.sub.3 and R.sub.4 taken together form a ring having the formula ##STR2## in which m and n are each integers from 1 to 3 and X is oxygen or --CH.sub.2 --, together with insecticidal compositions containing such compounds, and methods for controlling insects.Type: GrantFiled: May 10, 1985Date of Patent: November 12, 1985Assignee: Stauffer Chemical Co.Inventors: William G. Haag, Charles G. Chavdarian
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Patent number: 4549015Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification.The new compounds are useful e.g. as stabilizers in photographic material.Type: GrantFiled: June 14, 1983Date of Patent: October 22, 1985Assignee: Ciba-Geigy AGInventor: Frederick H. Howell
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Patent number: 4542219Abstract: Ethylene glycol derivatives, inclusive of salts thereof, which have the formula: ##STR1## wherein R.sup.1 is C.sub.8-26 aliphatic hydrocarbon residue; R.sup.2, R.sup.3 and R.sup.4 are each hydrogen or lower alkyl which may be substituted, or --N.sup.+ R.sup.2 R.sup.3 R.sup.4 represents cyclic ammonio, exhibit inhibitory activity to multiplication of tumor cells and antimicrobial activity.Type: GrantFiled: March 24, 1982Date of Patent: September 17, 1985Assignee: Takeda Chemical Industries, Ltd.Inventors: Motoo Hozumi, Hiroaki Nomura, Yoshio Yoshioka
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Patent number: 4522735Abstract: Amines are reacted with phosphorous trichloride to form N-dichlorophosphinoamines that are then reacted with a bisphenol in about equimolar amounts to provide polyphosphoramidite oligomers. The polyphosphoramidite oligomers are effective as stabilizers for polymers such as polyolefins, and form even more efficient stabilizer combinations with hydroxyphenylalkyleneyl isocyanurates.Type: GrantFiled: June 17, 1983Date of Patent: June 11, 1985Assignee: The B. F. Goodrich CompanyInventor: Dwight W. Chasar
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Patent number: 4519832Abstract: This invention relates to unsymmetrical aminosulfinamide derivatives of N-phosphonomethyl-glycine triesters which are useful as herbicides. This invention further relates to herbicidal compositions containing such derivatives and to herbicidal methods employing such compounds and compositions.Type: GrantFiled: April 27, 1984Date of Patent: May 28, 1985Assignee: Monsanto CompanyInventors: James A. Sikorski, Mary A. Hoobler
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Patent number: 4517183Abstract: The present invention provides pharmaceutical compositions containing N-substituted aziridine-2-carboxylic acid derivatives of the general formula: ##STR1## wherein X is a carboxyl, a cyano, an alkoxycarbonyl or an optionally substituted carbamoyl radical, R is a hydrogen atom, an aliphatic hydrocarbon radical which is saturated or can contain one or more unsaturations and can be substituted one or more times by halogen, alkoxy, hydroxyl, dialkylamino, dialkylaminoxy, cycloalkylamino, acylamino, acyl, nitro, alkylthio, alkylsulphinyl, alkylsulphonyl, cyano, carboxyl, alkoxycarbonyl or carbamoyl or by cycloalkyl or cycloalkenyl radicals optionally carrying alkyl, alkoxy or alkoxycarbonyl radicals, optionally interrupted by hetero atoms and optionally bridged, or by an aryl, hetaryl, aryloxy, arylthio, acyloxy, alkoxycarbonylamino or isothioureido radical, or R is a cycloalkyl or cycloalkenyl radical optionally substituted by alkyl, alkoxy or oxo groups, optionally interrupted by hetero atoms and optionally briType: GrantFiled: May 17, 1983Date of Patent: May 14, 1985Assignee: Boehringer Mannheim GmbHInventors: Elmar Bosies, Wolfgang Kampe, Max Thiel, Uwe Bicker, Dietmar Boerner
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Patent number: 4505735Abstract: It is found that certain novel tetra-substituted urea derivatives have herbicidal properties. The derivatives bear, on the same nitrogen atom a cyanomethyl group and an esterified methylene phosphonic acid group.Type: GrantFiled: January 20, 1983Date of Patent: March 19, 1985Assignee: Monsanto Co.Inventor: Rajendra K. Singh
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Patent number: 4501684Abstract: 2-naphthyl phosphoramidites are readily and inexpensively prepared by the reaction of N-dichlorophosphinoamines with a 2-naphthol in an alkylamine. The 2-naphthyl phosphoramidites are stabilizers for polymers such as the polyolefins and enhance the stabilizing activity of hydroxyphenylalkyleneyl isocyanurates.Type: GrantFiled: June 17, 1983Date of Patent: February 26, 1985Assignee: The B. F. Goodrich CompanyInventor: Dwight W. Chasar
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Patent number: 4495363Abstract: N-phosphonomethylglycine and novel derivatives thereof useful as phytotoxicants or herbicides.Type: GrantFiled: March 24, 1982Date of Patent: January 22, 1985Assignee: Monsanto Co.Inventor: John E. Franz
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Patent number: 4488894Abstract: This invention relates to unsymmetrical aminosulfinamide derivatives of N-phosphonomethylglycinonitrile which are useful as herbicides. This invention further relates to herbicidal compositions containing such derivatives and to herbicidal methods employing such compounds and compositions.Type: GrantFiled: February 21, 1984Date of Patent: December 18, 1984Assignee: Monsanto CompanyInventors: James A. Sikorski, Mary A. Hoobler
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Patent number: 4445928Abstract: This invention relates to aminosulfenamide derivatives of N-phosphonomethylglycine triesters which are useful as herbicides and a process for preparing these compounds. This invention further relates to herbicidal compositions containing such derivatives and to herbicidal methods employing such compounds and compositions.Type: GrantFiled: October 5, 1981Date of Patent: May 1, 1984Assignee: Monsanto CompanyInventors: James A. Sikorski, Mary A. Hoobler
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Patent number: 4421549Abstract: This invention relates to a new class of organic chemical compounds. More particularly, this invention is concerned with amido and hydrazido derivatives of N-trifluoroacetyl-N-phosphinothioylmethylglycine. This class of compounds has been found to be useful as intermediates in producing amido and hydrazido derivatives of N-phosphinothioylmethylglycine esters which show herbicidal activity. Some of the class of compounds of this invention also show herbicidal activity when applied to certain varieties of weeds or undesired plants.Type: GrantFiled: December 26, 1979Date of Patent: December 20, 1983Assignee: Monsanto CompanyInventors: John E. Franz, Robert J. Kaufman
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Patent number: 4408052Abstract: New carbamic acid esters, inclusive of salts thereof, which have the formula: ##STR1## wherein n is zero or 1; R.sup.1 and R.sup.2 independently represent --H, --OCH.sub.3 or --OCONHR.sup.6 ; in which R.sup.6 is C.sub.8-26 aliphatic hydrocarbon residue provided that at least one of R.sup.1 and R.sup.2 is --OCONHR.sup.6 ; and R.sup.3, R.sup.4 and R.sup.5 independently represent hydrogen or lower alkyl, or ##STR2## represents cyclic ammonio, exhibit inhibitory activity to multiplication of tumor cells and antimicrobial activity.Type: GrantFiled: February 25, 1981Date of Patent: October 4, 1983Assignee: Takeda Chemical Industries, Ltd.Inventors: Motoo Hozumi, Hiroaki Nomura, Yoshio Yoshioka
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Patent number: 4387060Abstract: In a synergistic pesticidal composition comprising (1) a pesticidally active compound and (2) a synergizing agent in amount sufficient to synergize the pesticidal activity of the pesticidally active compound, the improvement which comprises employing as the synergizing agent a 2-(thi)oxo-1,3,2-oxazaphospholane of the formula ##STR1## in which X represents oxygen or sulphur,R represents an optionally substituted alkyl, alkenyl, alkynyl, phenyl, alkoxy, alkenoxy, alkynoxy, alkylthio, aralkoxy, amino, mono- or di-alkylamino, heterocyclic amino, N-alkyl-N-aryl-amino, phenoxy or phenylthio radical,R.sup.1 represents hydrogen, optionally substituted alkyl, aralkyl, alkenyl, alkynyl or dialkylaminoalkyl,R.sup.2 represents hydrogen, alkylthioalkyl, or optionally substituted alkyl or aralkyl, or R.sup.1 and R.sup.2 together represent alkylene,R.sup.3 represents hydrogen or alkyl andR.sup.4 represents hydrogen, alkyl, or phenyl.Type: GrantFiled: November 3, 1980Date of Patent: June 7, 1983Assignee: Bayer AktiengesellschaftInventors: Hellmut Hoffmann, Bernd-Wieland Kruger, Wolfgang Behrenz
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Patent number: 4380515Abstract: Compounds of the formula I ##STR1## wherein R.sub.1 and R.sub.2 independently of one another are substituted or unsubstituted hydrocarbon radicals, or halogen,x and y independently of one another are 0, 1, 2 or 3, andA is a substituted primary or secondary aliphatic or alicyclic, aromatic or araliphatic amine, in which the substituents are identical or different, a heterocyclic amine or a hydrazine derivative.Type: GrantFiled: March 9, 1981Date of Patent: April 19, 1983Assignee: Ciba-Geigy CorporationInventors: Michael Rasberger, Samuel Evans
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Preparation of novel S-brom-dithiophosphoric, dithiophosphonic and dithiophosphinic acid derivatives
Patent number: 4369147Abstract: A compound of the formula ##STR1## in which R.sup.1 and R.sup.2 each independently is an optionally substituted alkyl, aralkyl, aryl, alkoxy, aryloxy, aralkoxy, alkylthio, arylthio, aralkylthio, alkylamino, arylamino or aralkylamino radical,is produced by reacting a compound of the formula ##STR2## in which X is hydrogen, an alkali metal ion, an optionally alkyl-, aralkyl- and/or aryl-substituted ammonium radical, a trialkylsilyl radical, or ##STR3## with bromine in the presence of an inert diluent at a temperature from about -50.degree. to 20.degree. C.The product can be employed as a flame retardant, a vulcanizing accelerator and/or an intermediate for synthesizing pesticides.Type: GrantFiled: November 24, 1981Date of Patent: January 18, 1983Assignee: Bayer AktiengesellschaftInventors: Jan Michalski, Marek Potrzebowski, Andrzej Lopusinski -
Patent number: 4368196Abstract: Novel phosphoric acid esters of the formula ##STR1## where R.sup.1 is alkoxy of a maximum of 4 carbon atoms or phenyl, R.sup.2 is alkyl of a maximum of 3 carbon atoms, alkoxy or alkylthio of a maximum of 4 carbon atoms, or alkylamino or dialkylamino, each alkyl being of a maximum of 4 carbon atoms, R.sup.3 is methyl, ethyl, hydrogen or chlorine, R.sup.4 and R.sup.5 are phenyl or alkyl of a maximum of 4 carbon atoms, or are, together with the nitrogen atom, a 5- to 7-membered heterocycle, and X is oxygen or sulfur, with the proviso that R.sup.1 is not phenyl when R.sup.2 is alkyl. The compounds are suitable for combating pests.Type: GrantFiled: May 29, 1981Date of Patent: January 11, 1983Assignee: BASF AktiengesellschaftInventors: Karl Kiehs, Heinrich Adolphi
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Patent number: 4359332Abstract: This disclosure relates to alkyl N-trifluoroacetyl-N-phosphonomethylglycine amide and hydrazide derivatives, to herbicidal compositions containing same and to the herbicidal use thereof. These amide and hydrazide derivatives are useful as pre-emergent and/or post-emergent herbicides.Type: GrantFiled: July 10, 1978Date of Patent: November 16, 1982Assignee: Monsanto CompanyInventors: John E. Franz, Robert J. Kaufman
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Patent number: 4357280Abstract: A method of processing photographic silver dye bleach materials which have been exposed imagewise is provided. The process steps are (1) silver developing, (2) dye bleaching, (3) silver bleaching and (4) fixing. The treatment baths for the process steps (2), (3) and (4), or the combined treatment baths useful for process step (3) with at least one the process steps (2) or (4) contain water-soluble tertiary phosphines as silver ligands. These phosphines effect an acceleration of the dye and silver bleaching and they are further suitable stabilizers and optionally antioxidants which yield stable treatment baths.Type: GrantFiled: May 29, 1981Date of Patent: November 2, 1982Assignee: Ciba-Geigy AGInventors: Christoph Chylewski, Gerald Jan, Roland Kurzen, Max Meier, Matthias Schellenberg
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Patent number: 4341772Abstract: S-(Diarylamino)thiophosphates are useful as miticides, insecticides, fungicides and ovicides.Type: GrantFiled: May 5, 1980Date of Patent: July 27, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Gary D. Grantham
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Patent number: 4336386Abstract: Novel quaternary compounds of the formula ##STR1## wherein R is a tertiary amine radical of from 6 to 40 carbon atoms;Y is alkylene, optionally interrupted by up to 3 oxygen atoms, of up to 12 carbon atoms, optionally containing a substituent selected from lower alkyl, alkoxy, hydroxy or hydroxyalkyl of not more than 10 carbon atoms each;A is selected from OM or OYR.sup.+ wherein Y and R are defined as above andM is an organic radical selected from alkyl or hydroxyalkyl of up to 6 carbon atoms, polyhydroxyalkyl of up to 10 carbon atoms, glyceryl, cycloalkyl of up to 6 carbon atoms, aryl or arylalkyl of up to 10 carbon atoms, or a salt radical selected from alkali metals, alkaline earth metals and mono-, di-, or tri-ethanolamine;X.sup.- is an anion;Z is an integer from 1 to 2, with the proviso that when A is OM, Z is 1 and when A is OYR, Z is 2.Type: GrantFiled: June 13, 1980Date of Patent: June 22, 1982Assignee: Mona Industries, Inc.Inventors: Anthony J. O'Lenick, Jr., Raymond L. Mayhew
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Patent number: 4331680Abstract: Novel compounds are described which are substituted benzophenone hydrazones. They have pesticidal activity, especially against insects and acarids, and pesticidal compositions and methods are described. Methods of making the compounds, and novel intermediates, are also described.Type: GrantFiled: August 25, 1980Date of Patent: May 25, 1982Assignee: The Boots CompanyInventors: David P. Giles, John C. Kerry, Antonin Kozlik, Bryan H. Palmer, Stephen W. Shutler, Robert J. Willis
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Patent number: 4322527Abstract: Compounds of the formula I ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl or C.sub.7 -C.sub.9 phenylalkyl and R.sub.2 is hydrogen or C.sub.1 -C.sub.18 alkyl, or, if R.sub.1 is hydrogen, R.sub.2 is a divalent 1,1,3,3,-tetramethylpropylene radical fused in the 2-position and 3-position or the 9-position and 10-position, and X is sulfur or a group --CH(R).sub.3 --, in which R.sub.3 is hydrogen or a radical of the formula II --CH(R.sub.4)--CH(R.sub.5)SR.sub.6, and each of R.sub.4 and R.sub.5 independently is hydrogen or C.sub.1 -C.sub.6 alkyl and R.sub.6 is C.sub.1 -C.sub.20 alkyl, while the alkyl group can be interrupted by one or more sulfur atoms, and A is a primary or secondary aliphatic or alicyclic, aromatic or araliphatic amine which contains substituents of the same type or mixed substituents, or a heterocyclic amine or a hydrazine derivative. These compounds are useful stabilizers for organic material.Type: GrantFiled: May 5, 1980Date of Patent: March 30, 1982Assignee: Ciba-Geigy CorporationInventor: Michael Rasberger
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Patent number: 4318845Abstract: The title compounds are prepared by reacting alkylated 1,1'-biphenyl-2,2'-diol or alkylated 2,2'-alkylidene-bis-phenol with phosphorus trichloride in an organic solvent and then reacting the intermediate phosphorochlorodite with an alkanolamine. Said phosphites are useful as stabilizers of organic polymers and lubricating oils, especially as processing stabilizers for polyolefins, elastomers, polyesters and polycarbonates.Type: GrantFiled: November 24, 1980Date of Patent: March 9, 1982Assignee: Ciba-Geigy CorporationInventors: John D. Spivack, Martin Dexter, Stephen D. Pastor
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Patent number: 4261727Abstract: This disclosure relates to novel N-substituted triesters of N-phosphonomethylglycine which are useful as herbicides. This disclosure further relates to herbicidal compositions containing such N-substituted N-phosphonomethylglycinates and to herbicidal methods employing such compounds and compositions.Type: GrantFiled: August 2, 1979Date of Patent: April 14, 1981Assignee: Monsanto CompanyInventor: Gerard A. Dutra
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Patent number: 4259330Abstract: This invention relates to novel phosphoramidates of the formula: ##STR1## wherein R.sup.1 is hydrogen, alkyl, cycloalkyl, or optionally substituted aralkyl, aryl, pyridyl, pyridylmethyl, pyridylethyl or pyrazinyl;R.sup.2 is hydrogen provided R.sup.1 is other than optionally substituted aryl; alkyl; cycloalkyl; alkoxyalkyl; alkylthioalkyl; cyanoalkyl; alkenyl; optionally substituted aralylky; or optionally substituted aryl, provided R.sup.1 is other than hydrogen;R.sup.1 and R.sup.2 taken together with the nitrogen to which they are attached form an optionally substituted morpholino or piperidino group;R.sup.3 is hydrogen, alkyl, cycloalkyl, alkenyl, or optionally substituted aralkyl or aryl;R.sup.4 is (C.sub.1 -C.sub.6) alkyl;R.sup.5 is (C.sub.3 -C.sub.4) alkyl; andX, Y and Z are independently oxygen or sulfur;the agronomically acceptable metal salts and metal salt complexes thereof; and to methods of using them to control nematodes.Type: GrantFiled: March 1, 1976Date of Patent: March 31, 1981Assignee: Rohm and Haas CompanyInventors: Harold E. Aller, Edward E. Kilbourn, Ernest D. Weiler, William D. Weir
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Patent number: 4259492Abstract: Compounds of the formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.18 alkyl,R.sub.2 is hydrogen or C.sub.1 -C.sub.18 alkyl, andA is a substituted primary or secondary aliphatic or alicyclic, aromatic or araliphatic amine, in which the substituents are identical or different, a heterocyclic amine or a hydrazine derivative.Type: GrantFiled: May 18, 1979Date of Patent: March 31, 1981Assignee: Ciba-Geigy CorporationInventor: Michael Rasberger
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Patent number: 4228109Abstract: This invention relates to aliphatic phosphorous containing compounds which are useful as herbicides. Additionally, they demonstrate tolerance towards desired, crops, e.g. wheat and rice.Type: GrantFiled: August 1, 1978Date of Patent: October 14, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: Richard F. Sauers
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Patent number: 4225521Abstract: This invention relates to phosphorus containing compounds which are useful as herbicides.Additionally, they demonstrate tolerance towards desired crops, e.g., cotton, soybeans and sugarbeets.Type: GrantFiled: August 1, 1978Date of Patent: September 30, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: Richard F. Sauers
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Patent number: 4217312Abstract: This invention relates to phosphorus containing compounds which are useful as herbicides.Additionally, they demonstrate tolerance towards desired crops, e.g., cotton, soybeans and sugarbeets.Type: GrantFiled: August 1, 1978Date of Patent: August 12, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: Richard F. Sauers
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Patent number: 4215064Abstract: Phosphobetaine Compounds of the formula ##STR1## wherein A is selected from O.sup.-, OM and --O--Y--R+B is selected from O.sup.- and OM.sup.-X.sup.- is an anionZ is an integer from 0 to 2 with the proviso that only one of A and B can be O.sup.- and Z is of a value necessary for charge balance and R is an amidoamine reactant moiety.Type: GrantFiled: November 30, 1978Date of Patent: July 29, 1980Assignees: Johnson & Johnson, Mona Industries, Inc.Inventors: Martin K. O. Lindemann, Raymond L. Mayhew, Anthony J. O'Lenick, Jr., Robert J. Verdicchio
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Patent number: 4209449Abstract: Novel phosphate quaternary compound of the formula ##STR1## wherein R is a tertiary amine radical of from 6 to 40 carbon atoms; andX is an anion.Type: GrantFiled: November 30, 1978Date of Patent: June 24, 1980Assignee: Mona IndustriesInventors: Raymond L. Mayhew, Anthony J. O'Lenick
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Patent number: 4203977Abstract: Phosphoric (phosphonic) acid esters of the formula ##STR1## where R.sup.1 denotes linear or branched alkyl of up to 4 carbon atoms, R.sup.2 denotes linear or branched alkyl, alkoxy or alkylthio, each of up to 4 carbon atoms, mono- or dialkylamino of up to 4 carbon atoms in each alkyl, or phenyl, R.sup.3 denotes linear or branched alkoxy or alkylthio of up to 4 carbon atoms, amino, mono- or dialkylamino of up to 4 carbon atoms in each alkyl, alkylalkoxyalkylamino of up to 4 carbon atoms in each alkyl or alkoxyalkyl, dialkoxyalkylamino of up to 4 carbon atoms in each alkoxyalkyl, alkylalkenylamino of up to 4 carbon atoms in each alkyl or alkenyl, alkylalkynylamino of up to 4 carbon atoms in each alkyl or alkynyl, N-methyl-N-methoxyamino, N-(2-methoxyethyl)-N-(2-cyanoethyl), a 5- or 6-membered nitrogenous heterocyclic ring which may contain several nitrogen atoms and optionally oxygen as ring members, R.sup.Type: GrantFiled: October 3, 1978Date of Patent: May 20, 1980Assignee: BASF AktiengesellschaftInventors: Karl Kiehs, Heinrich Adolphi
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Patent number: 4198510Abstract: A process for the preparation of carboxylic acids represented by a formula ##STR1## wherein R.sub.1 represents hydrogen atom or a lower alkyl radical, R.sub.2 represents hydrogen atom, lower alkyl or allyl radical and R.sub.3 represents phenyl, substituted phenyl, substituted naphthyl, dibenzofuranyl or substituted biphenyl. Following novel enamine and amidine compounds as intermediates for manufacturing the carboxylic acids and processes for the manufacture of said enamine and amidine compounds ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 represent the meanings as referred to and R.sub.4 represents dimethylamino, pyrrolidyl, piperidyl or morpholyl.Type: GrantFiled: July 7, 1978Date of Patent: April 15, 1980Assignees: Sanwa Kagaku Kenkyusho Co., Ltd., Takayuki ShioiriInventors: Takayuki Shioiri, Nobutaka Kawai, Masatoshi Ban
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Patent number: 4196090Abstract: Hydrocarbylpoly(oxyalkylene) aminophosphorylamido esters are monoesters and diesters of polyether alcohols and phosphoramidic acids. The esters find use as lubricating oil additives which impart lubricity to the oil.Type: GrantFiled: September 5, 1978Date of Patent: April 1, 1980Assignee: Chevron Research CompanyInventor: Jennifer E. Lilburn
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Patent number: 4185037Abstract: The subject of the invention is a process for the manufacture of polycondensation products of hydroxymethylphosphonium compounds and an amine, characterized in that (a) 1 mol of a tetrakis-(hydroxymethyl)-phosphonium compound is condensed with 0.02 to 0.3 mol, preferably 0.02 to 0.25 mol, of an amine at 100.degree. to 150.degree. C., optionally in the presence of an inert organic solvent, if appropriate free hydroxyl groups are at least partially etherified with at least one alkanol with 1 to 4 carbon atoms and if appropriate the salts of the polycondensation products are converted into the corresponding hydroxides.The condensation products are used for flameproofing organic fiber material, especially textiles.Type: GrantFiled: November 24, 1978Date of Patent: January 22, 1980Assignee: Ciba-Geigy CorporationInventors: Hermann Nachbur, Arthur Maeder
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Patent number: 4180394Abstract: This disclosure relates to derivatives of N-trifluoroacetyl-N-phosphonomethylglycinates wherein different moieties are attached to the phosphorus atom, to herbicidal compositions containing same and to the herbicidal use thereof.Type: GrantFiled: July 10, 1978Date of Patent: December 25, 1979Assignee: Monsanto CompanyInventors: John E. Franz, Robert J. Kaufman
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Patent number: 4162280Abstract: Preparation of a phosphorylated amidine of the formula ##STR1## wherein X is oxygen or sulfur and R, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are various organic radicals, which comprises reacting a phosphoric acid ester-amide of the formula ##STR2## with a carboxamide of the formula ##STR3## at a temperature between about 0.degree. and 50.degree. C., and then reacting the mixture with a base. Advantageously the reaction is effected at about 0.degree. to 15.degree. C. in the presence of an aliphatic or aromatic optionally chlorinated hydrocarbon or an alcohol as an inert solvent, and in the presence of a catalyst.Type: GrantFiled: March 17, 1978Date of Patent: July 24, 1979Assignee: Bayer AktiengesellschaftInventor: Eckart Kranz
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Patent number: 4159324Abstract: O-(1-Fluoro-2-halo-ethyl)(thiono)phosphoric(phosphonic) acid ester-amides of the formula ##STR1## in which R and R.sup.1 independently represent hydrogen, alkyl, haloalkyl or cyanoalkyl, orR and R.sup.1 conjointly with the nitrogen atom form a heterocyclic ring which can optionally be interrupted by further hetero-atoms,R.sup.2 represents ##STR2## alkoxy, halogenalkoxy or alkyl, Hal represents chlorine or bromine, andX represents oxygen or sulphur, which possess insecticidal acaricidal and nematocidal properties.Type: GrantFiled: June 15, 1977Date of Patent: June 26, 1979Assignee: Bayer AktiengesellschaftInventors: Dieter Arlt, Hellmut Hoffmann, Bernhard Homeyer, Wolfgang Behrenz, Ingeborg Hammann
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Patent number: 4144394Abstract: Compounds of the formulas ##STR1## WHEREIN: X represents oxygen or sulfur;Z represents the residue of a hydroxyl-containing moiety;R.sub.1 and R.sub.2 in formula (1) may be the same or different and individually represent alkyl, cycloalkyl or aryl and, together with the common nitrogen atom, represent a 5 or 6-member ring containing oxygen, sulfur or nitrogen or combination thereof;Nr.sub.1 r.sub.2 in formula (2) represent a 5 or 6-member ring containing oxygen, sulfur or nitrogen or combination thereof;N represents an integer having a value of 2 or greater and is equal to the number of hydroxyl groups on the original hydroxyl-containing moiety,Are prepared by reacting a phosphorohalidate with an amine in an organic solvent containing aqueous alkali metal or ammonium hydroxide.The compounds are useful as flame retardants for natural and synthetic materials.Type: GrantFiled: December 19, 1977Date of Patent: March 13, 1979Assignee: Monsanto CompanyInventors: Albert W. Morgan, Ignatius Schumacher, William Vanderlinde
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Patent number: 4140774Abstract: Compounds of the formula ##STR1## in which R represents halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.2 alkoxy, NO.sub.2 or S-CH.sub.3, R.sub.1 represents hydrogen or C.sub.1 -C.sub.6 -alkyl, R.sub.2 represents C.sub.1 -C.sub.6 -alkylamino, C.sub.3 -C.sub.8 -alkenylamino, N,N-di-(C.sub.1 -C.sub.6 -alkylamino), C.sub.5 -C.sub.8 -cycloalkylamino or a saturated N-heterocycle having from 4 to 8 C-atoms altogether of which 1 or 2 may stand in the side chain and in which one CH.sub.2 group of the cycle may be replaced by oxygen or sulfur, R.sub.3 represents C.sub.1 -C.sub.6 -alkyl, X is oxygen or sulfur and n is zero or a whole number in the range of from 1 to 3 exhibit a good herbicidal effect on some economically important weed grasses and dicotyledonous weeds and simultaneously they have excellent insecticidal and acaricidal properties.Type: GrantFiled: February 2, 1977Date of Patent: February 20, 1979Assignee: Hoechst AktiengesellschaftInventors: Gerhard Salbeck, Hubert Schonowsky, Gerhard Horlein, Hermann Bieringer, Peter Langeluddeke, Ludwig Emmel, Anna Waltersdorfer
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Patent number: 4126442Abstract: o-Phosphoroamidophenylmorpholines of the structure ##STR1## wherein Y represents a branched chain alkyl group of 3 to about 6 carbon atoms and z represents the group ##STR2## in which R.sub.1 is lower alkyl, lower alkenyl, aralkyl or aryl, R.sub.2 is hydrogen, lower alkyl, lower alkenyl, aralkyl or aryl, and X is O or S. The compounds are useful as herbicides and may be applied as a pre-emergence or post-emergence treatment to control unwanted plants.Type: GrantFiled: March 23, 1978Date of Patent: November 21, 1978Assignee: United States Borax & Chemical Corp.Inventors: Kelvin K. Shen, Thomas S. Griffin
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Patent number: 4115556Abstract: Compounds having the formula ##STR1## in which R.sub.1 is lower alkyl or lower alkoxy, R.sub.2 is lower alkoxy or methylthio-substituted lower alkoxy, and R.sub.3 is ##STR2## R.sub.4 and R.sub.5 are lower alkyl, m is 1 or 2 and n is 0 or an integer from 1 to 4. The compounds have utility as insecticides and acaricides.Type: GrantFiled: July 25, 1977Date of Patent: September 19, 1978Assignee: Stauffer Chemical CompanyInventors: Hsiao Ling Lam, Eugene G. Teach
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Patent number: 4105432Abstract: Lactones prepared by cyclizing certain N-(2-hydroxyalkyl)-N-phosphonomethylglycine compounds are useful as post-emergent herbicides for the treatment of undesired plants.Type: GrantFiled: July 18, 1977Date of Patent: August 8, 1978Assignee: Monsanto CompanyInventor: Van R. Gaertner
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Patent number: 4105790Abstract: The invention concerns .alpha.-aminoacyl derivatives of phenyl-, phenoxy-, thiophenoxy- and phenylsulphinylalkanoic acids together with their amides, esters and pharmaceutically acceptable salts; processes for their preparation; and pharmaceutical compositions for therapeutic use in inhibiting the formation of thrombi and also in reducing the persistence of thrombi formed in the blood of warm blooded animals. Representative compounds of the invention are methyl 4-(aminoacetyl)phenoxyacetate, 4-(aminoacetyl)phenoxyacetic acid and methyl 4-(aminoacetyl)-thiophenoxyacetate, preferably as their hydrochlorides.Type: GrantFiled: November 9, 1976Date of Patent: August 8, 1978Assignee: Imperial Chemical Industries LimitedInventors: Clifford R. Hughes, Stephen J. Jackson, John Preston, Peter L. Walton
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Patent number: 4099954Abstract: The present invention relates to new herbicidal phosphorothioate (phosphorodithioate) derivatives and to preparation thereof.Type: GrantFiled: August 11, 1976Date of Patent: July 11, 1978Assignee: Sumitomo Chemical Company, LimitedInventors: Shunichi Hashimoto, Kunio Mukai
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Patent number: 4086302Abstract: Compounds of the formulas ##STR1## WHEREIN: X represents oxygen or sulfur;Z represents the residue of a hydroxyl-containing moiety;R.sub.1 and R.sub.2 in formula (1) may be the same or different and individually represent alkyl, cycloalkyl or aryl and, together with the common nitrogen atom, represent a 5 or 6 member ring containing oxygen, sulfur or nitrogen or combination thereof;Nr.sub.1 r.sub.2 in formula (2) represents a 5 or 6 member ring containing oxygen, sulfur or nitrogen or combination thereof;n represents an integer having a value of 2 or greater and is equal to the number of hydroxyl groups on the orginal hydroxyl-containing moiety, the residue of which is now represented by Z.are prepared by reacting a phosphorohalidate with an amine in an organic solvent containing aqueous alkali metal or ammonium hydroxide.The compounds are useful as flame retardants for natural and synthetic materials.Type: GrantFiled: September 29, 1976Date of Patent: April 25, 1978Assignee: Monsanto CompanyInventors: Albert W. Morgan, Ignatius Schumacher, William Vanderlinde
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Patent number: 4062909Abstract: Compounds of the formulas ##STR1## WHEREIN: X represents oxygen or sulfur;Z represents the residue of a hydroxyl-containing moiety;R.sub.1 and R.sub.2 in formula (1) may be the same or different and individually represent alkyl, cycloalkyl or aryl and, together with the common nitrogen atom, represent a 5 or 6-member ring containing oxygen, sulfur or nitrogen or combination thereof;Nr.sub.1 r.sub.2 in formula (2) represent a 5 or 6-member ring containing oxygen, sulfur or nitrogen or combination thereof;n represents an integer having a value of 2 or greater and is equal to the number of hydroxyl groups on the original hydroxyl-containing moiety;Are prepared by reacting a phosphorohalidate with an amine in an organic solvent containing aqueous alkali metal or ammonium hydroxide.The compounds are useful as flame retardants for natural and synthetic materials.Type: GrantFiled: July 28, 1975Date of Patent: December 13, 1977Assignee: Monsanto CompanyInventors: Albert W. Morgan, Ignatius Schumacher, William Vanderlinde
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Patent number: 4059432Abstract: A plant growth regulator comprising as an active ingredient a compound having a novel 2-sulfonyloxyethylphosphonic or -thionophosphonic acid skeleton of the formula ##STR1## and a process for the production of the above compound. A method for regulating the growth of plants which comprises applying the above regulator to plants or to the locus in which the plants are growing or will be grown.Type: GrantFiled: May 23, 1975Date of Patent: November 22, 1977Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Tetsuo Takematsu, Makoto Konnai, Makoto Takeda, Nobuhiko Fuga, Kaoru Ikeda, Kiyoshi Shugaya