Thiocarboxamides (i.e., Compounds Containing -c(=s)-hnh, Wherein Substitution May Be Made For Hydrogen Only) Patents (Class 564/74)
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Patent number: 5101071Abstract: Pesticidal compositions for use against insects and acarines comprising a compound of Formula (I):R.sup.1 --(CA.dbd.CA').sub.n C(.dbd.S)NR.sup.2 R.sup.3 (I)whereinR.sup.1 is: C.sub.1-14 alkyl optionally substituted by C.sub.1-6 alkoxy, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.2-6 alkenyloxy, C.sub.2-6 alkynyloxy, aryl, aryloxy or aryl (C.sub.1-6) alkoxy; aryloxy or aryl (C.sub.1-6) alkoxy; any of which groups may be substituted by halo,n is 1 or 2,each A and A' is independently hydrogen, halo, C.sub.1-4 alkyl or halo (C.sub.1-4) alkyland R.sup.2 and R.sup.3 are independently hydrogen, C.sub.1-6 alkyl or C.sub.3-6 cycloalkyl, either of which may be substituted by one or more of halo, C.sub.2-6 alkenyl, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkenyl, C.sub.1-6 alkoxy, C.sub.2-6 alkynyl or cyano, except that, when n is 1 and R.sup.2 is alkyl and R.sup.3 is hydrogen and A and A' are both hydrogen then R.sup.1 is not substituted alkyl.Type: GrantFiled: July 22, 1991Date of Patent: March 31, 1992Assignee: Burroughs Wellcome Co.Inventors: Robert J. Blade, Robert J. Peek
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Patent number: 5091420Abstract: Pesticidal compositions for use against insects and acarines comprising a compound of Formula (I):R.sup.1 --(CA.dbd.CA').sub.n C(.dbd.S)NR.sup.2 R.sup.3 (I)wherein R.sup.1 is: C.sub.1-14 alkyl optionally substituted by C.sub.1-6 alkoxy, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.2-6 alkenyloxy, C.sub.2-6 alkynyloxy, aryl, aryloxy or aryl (C.sub.1-6) alkoxy; aryloxy or aryl (C.sub.1-6) alkoxy; any of which groups may be substituted by halo,n is 1 or 2,each A and A' is independently hydrogen, halo, C.sub.1-4 alkyl or halo (C.sub.1-4) alkyl and R.sup.2 and R.sup.3 are independently hydrogen, C.sub.1-6 alkyl or C.sub.3-6 cycloalkyl, either of which may be substituted by one or more of halo, C.sub.2-6 alkenyl, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkenyl, C.sub.1-6 alkoxy, C.sub.2-6 alkynyl or cyano, except that, when n is 1 and R.sup.2 is alkyl and R.sup.3 is hydrogen and A and A' are both hydrogen then R.sup.1 is not substituted alkyl.Most of the compounds of Formula (I) are novel.Type: GrantFiled: July 26, 1990Date of Patent: February 25, 1992Assignee: Burroughs Wellcome Co.Inventors: Robert J. Blade, Robert J. Peek
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Patent number: 5043466Abstract: The preparation of compounds having the formula I ##STR1## where R.sup.1 is --CN, --CO--N(CH.sub.3).sub.2 or --CS--N(CH.sub.3).sub.2 and R.sup.2 is hydrogen, methyl or a removable protecting group is carried out by condensing a compound having the formula ##STR2## where M is lithium, sodium, potassium or halomagnesium and R.sup.3 is methyl or a removable protecting group in a solvent comprising 80-100% of one or more hydrocarbons and 0-20% of one or more ethers.The solvent enables less inconvenient reaction temperatures to be used and higher yields to be obtained. Compounds (I) are new per se where R.sup.1 is --CS--N(CH.sub.3).sub.2. Compounds (I) are chemical intermediates for preparing N,N-dimethyl-2-(1-hydroxycyclohexyl)-2-(4-hydroxyphenyl or 4-methoxyphenyl) ethylamine and pharmaceutically acceptable salts thereof. These end products are antidepressants.Type: GrantFiled: January 26, 1990Date of Patent: August 27, 1991Assignee: John Wyeth & Bro., LimitedInventor: Robin G. Shepard
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Patent number: 5041663Abstract: The invention relates to novel oxime ethers of the formula I ##STR1## wherein R.sub.1 is hydrogen, halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, lower alkylthio, lower haloalkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower haloalkylsulfinyl, lower haloalkylsulfonyl or nitro, each of R.sub.2 and R.sub.3 is hydrogen, halogen, lower alkyl, lower alkoxy or lower haloalkoxy, and Q is an unsubstituted or substituted lower alkyl, lower alkenyl, lower alkynyl or cycloalkyl group, a lower alkanoyl radical, an aliphatic, cycloaliphatic, aromatic or heterocyclic acyl radical which may be substituted or unsubstituted, a carbonyl or thiocarbonyl radical, an aryl or aralkyl radical, an acylimidomethyl radical, a phthalimidomethyl radical or a heterocyclic radical.These compounds are able to act as antidotes or safeners for protecting cultivated plants from the phytotoxic action of aggressive herbicides.Type: GrantFiled: December 11, 1990Date of Patent: August 20, 1991Assignee: Ciba-Geigy CorporationInventors: Henry Martin, Urs Fricker
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Patent number: 5041653Abstract: A method for sensitizing hypoxic tumor cells to radiation using derivatives of benzamide are disclosed. Some of the compounds useful in the method of the invention are novel.Type: GrantFiled: September 24, 1990Date of Patent: August 20, 1991Assignee: SRI InternationalInventors: William W. Lee, Edward W. Grange, J. Martin Brown
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Patent number: 5021414Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyphenyl-ethylene or vinylene nucleus;wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages,wherein R.sup.1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 -- or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --S--, --SO-- or --SO.sub.2 --,wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene;wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro;or a salt thereof when appropriate.Type: GrantFiled: December 18, 1989Date of Patent: June 4, 1991Assignee: Imperial Chemical Industries PLCInventors: William R. Pilgrim, Derek W. Young, Brian S. Tait, Graham C. Crawley, Philip N. Edwards, George B. Hill
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Patent number: 5013759Abstract: Substituted phenylacetic acid amide compounds, and pharmaceutically-acceptable salts thereof, of the formula: ##STR1## wherein X is O or S; R.sub.1 is H, OH or CH.sub.3 ; R.sub.2 is straight chain alkenyl, branched chain or cyclic hydrocarbon having from about 7 to about 24 carbon atoms; R.sub.3 is OH, OSO.sub.3.sup.-, OPO.sub.3.sup.-- or a short chain ester with from about 1 to about 6 carbon atoms.Type: GrantFiled: January 31, 1990Date of Patent: May 7, 1991Assignee: The Procter & Gamble CompanyInventors: Elizabeth F. Berman, Brian L. Buckwalter, Thomas L. Cupps, Joseph H. Gardner
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Patent number: 4997980Abstract: Disclosed are novel compounds of the formula: ##STR1## wherein: X=--NR.sub.5 R.sub.6, or --OR.sub.7 ;R.sub.1 and R.sub.2 are independently hydrogen, substituted or unsubstituted alkyl, haloalkyl, hydroxyalkyl alkoxyalkyl, alkylaminoalkyl or arylalkyl having up to 18 carbons, cycloalkyl; phenyl or naphthyl; alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituents;R.sub.3 is hydrogen, benzyl, alkoxybenzyl, halobenzyl or alkylbenzyl, provided that if neither R.sub.1 nor R.sub.2 is hydrogen, then R.sub.3 is hydrogen;R.sub.4 is a divalent aromatic group which is substituted or unsubstituted;R.sub.5, R.sub.6 and R.sub.7 are independently hydrogen, alkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl, acylaminoalkyl, aminoalkyl or phenylalkyl having up to 12 carbons; a cycloalkyl substitutent; phenyl or naphthyl; an alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituent;Furthermore, either R.sub.1 and R.sub.3 or R.sub.1 and R.sub.Type: GrantFiled: April 17, 1989Date of Patent: March 5, 1991Assignee: Anitec Image CorporationInventors: Bruce M. Resnick, Allan J. Wexler
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Patent number: 4983630Abstract: There are provided new 2,2-difluorocyclopropylethane derivatives of general formula I ##STR1## in which A, B and R.sup.1-5 have the meanings given in the description and processes for their preparation. The compounds of the invention can be used as pesticides, especially against insects and mites.Type: GrantFiled: November 28, 1988Date of Patent: January 8, 1991Assignee: Schering AktiengesellschaftInventors: Peter Wegner, Hartmut Joppien, Gunter Homberger, Arnim Kohn
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Patent number: 4968677Abstract: 1-Aryl-2-naphthoylamines of formula I are described ##STR1## wherein R.sub.1 is halogen, nitro, cyano, C.sub.1 -C.sub.6 alkyl that is unsubstituted or mono- or poly-substituted by halogen and/or C.sub.1 -C.sub.3 alkoxy, or is C.sub.3 -C.sub.6 cycloalkyl, OR.sub.4, NR.sub.5 R.sub.6, CO2R.sub.5, CONR.sub.5 R.sub.6 or NHCOR.sub.7, or wherein two adjacent positions in the nucleus are bridged by a methylenedioxy or ethylenedioxy group that is unsubstituted or mono- or poly-substituted by fluorine, wherein further R.sub.4 is hydrogen or C.sub.1 -C.sub.6 alkyl that is unsubstituted or substituted by C.sub.1 -C.sub.3 alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.4 alkenyl, 2-propynyl, 3-halo-2-propynyl, ##STR2## or COR.sub.7, each of R.sub.5 and R.sub.6, independently of the other, is H or C.sub.1 -C.sub.4 alkyl, R.sub.7 is C.sub.1 -C.sub.Type: GrantFiled: June 14, 1989Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventor: Peter Riebli
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Patent number: 4962224Abstract: Disclosed herein are N-naphthoylglycines and methods of their preparation. The N-naphthoylglycines are novel aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.Type: GrantFiled: August 22, 1989Date of Patent: October 9, 1990Assignee: American Home Products CorporationInventors: Jay E. Wrobel, Kazimir Sestanj
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Patent number: 4950789Abstract: Aromatic polyalkyleneoxy polyamines which are the reaction products of an aminocarbonyl, a polyalkyleneoxy polyamine, and aromatic diamines are useful in reaction injection molding processes to enhance the physical properties of the products produced. In addition, the polyamines of this invention are also useful as compatiblilizing agents in RIM systems to compatibilize mixtures of high molecular weight and low molecular weight polyols.Type: GrantFiled: January 25, 1989Date of Patent: August 21, 1990Assignee: The Dow Chemical CompanyInventor: Benny G. Barron
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Patent number: 4935513Abstract: An amide is thiated to the corresponding thioamide by reacting it with phosphorus pentasulfide in the presence of a Group IIA metal fluoride as an adjuvant.Type: GrantFiled: June 7, 1989Date of Patent: June 19, 1990Assignee: Ethyl CorporationInventor: Barbara C. Stahly
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Patent number: 4935514Abstract: An amide is thiated to the corresponding thioamide by reacting it with phosphorus pentasulfide in the presence of an adjuvant selected from diatomaceous earth, zeolites, and molecular sieves.Type: GrantFiled: June 6, 1989Date of Patent: June 19, 1990Assignee: Ethyl CorporationInventor: Barbara C. Stahly
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Patent number: 4935510Abstract: Ammonium hydroxide is used in the recovery of a thiono compound prepared by reacting an organic carbonyl compound with phosphorus pentasulfide to improve the product yield.Type: GrantFiled: June 7, 1989Date of Patent: June 19, 1990Assignee: Ethyl CorporationInventor: Barbara C. Stahly
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Patent number: 4904661Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyphenyl-ethylene or vinylene nucleus;wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages,wherein R.sup.1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 -- or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --S--, --SO-- or --SO.sub.2 --, wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene;wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro;or a salt thereof when appropriate.Type: GrantFiled: December 16, 1987Date of Patent: February 27, 1990Assignee: Imperial Chemical Industries PLCInventors: William R. Pilgrim, Derek W. Young, Brian S. Tait, Graham C. Crawley, Philip N. Edwards, George B. Hill
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Patent number: 4885027Abstract: Arylmethylenesulfonamidoacetamide and thioacetamide derivatives and arylmethylenesulfonamidoester intermediates therefor. The compounds are useful as selective herbicides especially with respect to the prevention and elimination of barnyardgrass in grass crops, especially in rice crops.Type: GrantFiled: November 14, 1986Date of Patent: December 5, 1989Assignee: Chevron Research CompanyInventor: Patricia B. Pomidor
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Patent number: 4863966Abstract: Compounds of formula (I) are pesticides having activity against arthropods: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are H, alkyl, alkoxy, halo, cyano or trifluoromethyl, or two of R.sup.1, R.sup.2 and R.sup.3 are linked to form a 3 or 4 carbon atom group;X is O or NA where A is H or alkyl;R is H or alkyl; andR.sup.4 and R.sup.5 are H, alkenyl or haloalkenyl or optionally substituted alkyl, aryl or aralkyl, or NR.sup.4 R.sup.5 represents a heterocyclic ring; or an acid addition salt thereof.The invention further provides methods for the preparation of the compounds, pesticidal formulations containing them, and their use in controlling arthropod pests.Type: GrantFiled: February 17, 1981Date of Patent: September 5, 1989Assignee: Burroughs Wellcome Co.Inventors: Malcolm H. Black, Alexander D. Frenkel, Peter T. Roberts
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Patent number: 4853484Abstract: Disclosed herein are N-[[6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]thioxomethyl]-N-methylgly cine S-oxide (tolrestat S-oxide) and the amide thereof and methods of their preparation. The S-oxides are new aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.Type: GrantFiled: October 28, 1987Date of Patent: August 1, 1989Assignee: American Home Products CorporationInventors: Eckhardt S. Ferdinandi, Michael S. Malamas, Kazimir Sestanj, Surendra N. Sehgal
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Patent number: 4808628Abstract: An amide derivative of the formula (I): ##STR1## or a tautomeric form thereof, wherein R is a phenyl group substituted in the 4-position by a group of R.sup.1 XCH.sub.2--, where R.sup.1 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.1 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 alkylcarbonyl, or H, and X is oxygen or sulphur; E is CN, or CSNH.sub.2, or CONH.sub.2 ; and Y is C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, 1-pyrazolyl or 2-furyl. Compositions and processes for using these derivatives to combat plant fungi are also disclosed.Type: GrantFiled: November 12, 1987Date of Patent: February 28, 1989Assignee: Imperial Chemical Industries PLCInventors: Margaret C. Shephard, Patrick J. Crowley
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Patent number: 4795487Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: the substituent X is chosen from cyano, carbamoyl and thiocarbamoyl;Z is selected from hydrogen, methyl, C.sub.1 to C.sub.4 alkanoyl, sulfamoyl, dimethylsulfamoyl and trifluoroacetylamino;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl and alkynyl;R.sup.3 is selected from alkyl; andR.sup.4 is selected from hydrogen, alkyl, and alkoxycarbonyl.The compounds of the invention show herbicidal properties and plant growth regulating properties and in further embodiments and the invention provides processes for the preparation of compounds of formula I, intermediates useful in the preparation of the compounds of formula I, compositions containing as active ingredient a compound of formula I, and herbicidal and plant growth regulating processes utilizing compounds of formula I.Type: GrantFiled: July 16, 1986Date of Patent: January 3, 1989Assignee: ICI Australia LimitedInventors: Keith G. Watson, Craig G. Lovel
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Patent number: 4753934Abstract: Compounds of the formula ##STR1## wherein A, B, R.sub.1, X and Q are substituents of various types, and acid addition salts thereof. The compounds are useful as fungicides.Type: GrantFiled: September 29, 1986Date of Patent: June 28, 1988Assignee: Celamerck GmbH & Co. KGInventors: Josef Nickl, Helmut Pieper, Jurgen Curtze, Christo Drandarevski, Sigmund Lust
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Patent number: 4752615Abstract: A compound of the formula: ##STR1## useful as a fungicidal agent against phytopathogenic fungi, particularly their strains resistant to benzimidazole, thiophanate and/or cyclic imide fungicides.Type: GrantFiled: November 13, 1986Date of Patent: June 21, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Junya Takahashi, Toshiro Kato, Hiroshi Noguchi, Yukio Oguri, Shigeo Yamamoto, Katsuzo Kamoshita
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Patent number: 4752321Abstract: A compound of the general formula (I): ##STR1## wherein R is C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl, both optionally substituted by lower alkyl, halogen or trialkylsilyl; E is CN or CSHN.sub.2 ; and Y is C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, 1-pyrazolyl or 2-furyl. The compounds have fungicidal and plant growth regulating activity.Type: GrantFiled: November 18, 1986Date of Patent: June 21, 1988Assignee: Imperial Chemical Industries PLCInventors: Stephen P. Heaney, Patrick J. Crowley, Laurence G. Reynolds
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Patent number: 4741897Abstract: The present invention relates to new compounds of the general formula: ##STR1## where X is iodine or hydrogen; A is a linking portion; and R is an iodinatable aryl or heteroaryl group having electron donating substituents. These compounds are useful precursors to the iodinated thyroid hormones for radioimmunoassay determination of thyroid hormones in biological fluids.Type: GrantFiled: July 8, 1986Date of Patent: May 3, 1988Assignee: Baxter TravenolInventors: Judith Andrews, Christine Burns, James Quick
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Patent number: 4736056Abstract: This invention relates to a process for preparing a malonic acid derivative compound of formula (i) depicted herein in high yield and high purity by reacting a malonic acid derivative compound of formula (ii) depicted herein with an alkylating agent of formula (iii) depicted herein in the presence of a solvent and a base.Type: GrantFiled: December 15, 1986Date of Patent: April 5, 1988Inventors: Oliver W. Smith, Russell J. Outcalt
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Patent number: 4690708Abstract: A herbicide of the formula: ##STR1## in which: Z is N or CX',W, Y, Y', X, Z' and X' represent H, a halogen atom, NO.sub.2, CN or a polyhalogenoalkyl, alkyl or alkoxy group,R.sup.2 represents H, halogen, substituted alkyl, allyl, propargyl, CN, NR.sup.4 R.sup.5, C(X.sup.2)R.sup.7, C(X.sup.2)X.sup.3 R.sup.8, C(X.sup.2)NR.sup.4 R.sup.5, SO.sub.2 F, SO.sub.2 OR.sup.8, SO.sub.2 NR.sup.4 R.sup.5 or P(X.sup.2)R.sup.9 R.sup.10,R.sup.1 is halogen, X.sup.2 R.sup.3 or NR.sup.4 R.sup.5,R.sup.3 is optionally substituted alkyl or is allyl or propargyl,R.sup.4, R.sup.7 and R.sup.8 represent H, alkyl, cycloalkyl, phenyl, allyl, propargyl or the like,R.sup.5 represents R.sup.4, a cation or OR.sup.6, R.sup.6 being H, a cation or alkyl,X.sup.2 and X.sup.3 are O or S,R.sup.9 and R.sup.10 are H, alkyl, OH, OM or R.sup.1, andM is a cation.Type: GrantFiled: July 11, 1984Date of Patent: September 1, 1987Assignee: Rhone-Poulenc AgrochimieInventors: Alain Chene, Guy Borrod
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Patent number: 4686232Abstract: A compound of the formula: ##STR1## useful as a fungicidal agent against phytopathogenic fungi, particularly strains thereof which are resistant to benzimidazole or thiophanate fungicides and/or cyclic imide fungicides.Type: GrantFiled: February 6, 1984Date of Patent: August 11, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Junya Takahashi, Mitsuru Sasaki, Hiroshi Noguchi, Toshiro Kato
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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: 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: 4652303Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: W are selected from the group consisting of:the groups R.sup.5 --CO-- and R.sup.5 --CS-- wherein: R.sup.5 is selected from alkenyl, alkynyl, benzyl, phenyl, substituted alkyl, substituted alkenyl, substituted alkynyl, substituted benzyl, substituted phenyl and the acetal, hemiacetal, oxime, imine and Schiff base derivatives of the group R.sup.5 --CO--;the groups Y--CO-- and Y--CS-- wherein Y is selected from hydroxy, mercapto, alkylthio and the groups MO-- and MS-- wherein M is an organic or an inorganic cation;the groups R.sup.6 R.sup.7 NCO-- and R.sup.6 R.sup.7 NCS-- wherein R.sup.6 and R.sup.7 are independently selected from hydrogen, alkyl, substituted alkyl, alkanoyl, carboxy, alkoxycarbonyl, alkylsulfonyl, benzoyl, benzenesulfonyl, substituted benzoyl, substituted benzenesulfonyl, or R.sup.6 and R.sup.Type: GrantFiled: July 2, 1984Date of Patent: March 24, 1987Assignee: ICI Australia LimitedInventors: Keith G. Watson, Graham J. Bird, Graeme J. Farquharson
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Patent number: 4643763Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: m is an integer selected from 1 to 4;n is zero or an integer selected from 1 to 4;x are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, alkylthio, sulfamoyl, substituted sulfamoyl, amino, substituted amino, the group --(CH.sub.2).sub.p C(.dbd.A)Z in which p is zero or one A is oxygen or sulfur, and Z is hydrogen, hydroxy, alkoxy, alkylthio, alkyl, substituted alkyl, amino or substituted amino; the group --NHC(.dbd.B(NR.sup.7 R.sup.8 in which B is oxygen or sulfur and R.sup.7 and R.sup.8 are hydrogen or alkyl;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; andR.sup.4 is selected from hydrogen, halogen, alkyl, cyano and alkoxycarbonyl.Type: GrantFiled: September 10, 1985Date of Patent: February 17, 1987Assignee: ICI Australia LimitedInventors: Graeme J. Farquharson, Keith G. Watson, Graham J. Bird
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Patent number: 4633014Abstract: Substituted 3-hydrazinopropionates comprising compounds of the general fola: ##STR1## wherein R.sup.1, R.sup.2 =H, an alkyl, a substituted alkyl, hydroxycarbonyl, alkoxycarbonyl, an aryl, an aralkyl, an unsaturated alkyl, a substituted aryl or a substituted aralkyl: ##STR2## wherein R.sup.7, R.sup.8 =H, an alkyl, an unsaturated alkyl, an aralkyl, an aryl, a substituted alkyl,R.sup.9 =OH, an alkoxy, an aralkoxy, an alkyl, an unsaturated alkyl, an aryl, a substituted aryl, an aralkyl;R.sup.4 is --C.tbd.N, --COR.sup.10, wherein R.sup.10 =OR.sup.11, NR.sup.12 R.sup.13, where R.sup.11 is H, an alkyl, an aralkyl and an alkali metal, R.sup.11 and R.sup.12 are each H, an alkyl, an aralkyl, an aryl;R.sup.5, R.sup.6 = an alkyl, an aryl, an aralkyl.Type: GrantFiled: July 6, 1984Date of Patent: December 30, 1986Assignee: Institut Organicheskogo Sinteza Akademii Nauk Latviiskoi SsrInventors: Gunar A. Bremanis, Ivars Y. Kalvinsh, Irene B. Antsena, Edmund Y. Lukevits, Maris M. Veveris, Valeryans Y. Kauss, Peter T. Trapentsier, Edvards E. Liepinsh
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Patent number: 4629498Abstract: Phenoxyphenoxyalkanoylthioamides of the formula I ##STR1## wherein X.sub.1 is chlorine or trifluoromethyl, X.sub.2 is chlorine or nitro, R.sub.1 is C.sub.1 -C.sub.4 alkyl, and R.sub.2 is the amino group or an amidino group ##STR2## wherein each of R.sub.3 and R.sub.4 independently is hydrogen or C.sub.1 --C.sub.4 alkyl or taken together they form a C.sub.4 --C.sub.5 alkylene chain, have herbicidal and growth regulating properties. They are suitable for selectively controlling weeds in crops of useful plants, especially in cereals and rice.Type: GrantFiled: May 2, 1985Date of Patent: December 16, 1986Assignee: Ciba-Geigy CorporationInventors: Otto Rohr, Georg Pissiotas
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Patent number: 4628061Abstract: Novel compounds have a formula (I) ##STR1## wherein ##STR2## represents a bicyclo [2,2,1] hept-2Z-ene, bicyclo [2,2,1] heptane, 7-oxa-bicyclo [2,2,1] hept-2Z-ene, 7-oxa-bicyclo [2,2,1] heptane, bicyclo [2,2,2] oct-2Z-ene or bicyclo [2,2,2] octane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group ANR.sup.2 R, a 6,6-dimethyl-bicyclo [3,1,1] heptane substituted at the 2-position by the group R.sup.1 and at the 3-position by the group ANR.sup.2 R or at the 2-position by the group ANR.sup.2 R and at the 3-position by the group R.sup.1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R.sup.1 and at the 5-position by the group ANR.sup.2 R or a 1-hydroxycyclopentane substituted at the 2-position by the group R.sup.1 and at the 2-position by the group ANR.sup.2 R, R.sup.Type: GrantFiled: August 23, 1983Date of Patent: December 9, 1986Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 4625048Abstract: Carbamic acid esters of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, X, and Y are as defined hereinafter, process for their preparation, as well as pesticidal compositions containing these compounds as the active ingredient and methods for using the pesticidal compositions for the control of pests are described.Type: GrantFiled: December 20, 1984Date of Patent: November 25, 1986Assignee: Hoffmann-La Roche Inc.Inventor: Rene Zurfluh
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Patent number: 4604128Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: m is an integer selected from 1 to 4;n is zero or an integer selected from 1 to 4;X are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, alkylthio, sulfamoyl, substituted sulfamoyl, amino, substituted amino, the group --(CH.sub.2).sub.p C(.dbd.A)Z in which p is zero or one A is oxygen or sulfur, and Z is hydrogen, hydroxy, alkoxy, alkylthio, alkyl, substituted alkyl, amino or substituted amino, the group --NHC(.dbd.B)NR.sup.7 R.sup.8 in which B is oxygen or sulfur and R.sup.7 and R.sup.8 are hydrogen or alkyl;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; andR.sup.4 is selected from hydrogen, halogen, alkyl, cyano and alkoxycarbonyl.Type: GrantFiled: September 10, 1985Date of Patent: August 5, 1986Assignee: ICI Australia LimitedInventors: Keith G. Watson, John D. Wishart, Graeme J. Farquharson, Graham J. Bird, Lindsay E. Cross
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Patent number: 4581375Abstract: The present invention relates to new substituted hydroxy-malonic acid amide-thioamides of the formula (I) ##STR1## in which R represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heteroaryl,and a process for their preparation and their use as agents for combating pests, in particular insecticides and acaricides.Type: GrantFiled: February 24, 1984Date of Patent: April 8, 1986Assignee: Bayer AktiengesellschaftInventors: Rudolf Fauss, Kurt Findeisen, Benedikt Becker, Ingeborg Hammann, Bernhard Homeyer
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Patent number: 4579581Abstract: Herbicidal and fungicidal benzamide derivatives of the formula (I) ##STR1## wherein R.sup.1 is an optionally substituted alkyl, alkenyl, aryl, heterocyclyl, benzyl, or heterocyclylmethyl radical;R.sup.2 is hydrogen, or an optionally substituted alkyl, alkenyl, benzyl, or heterocyclylmethyl, radical;X is oxygen, sulphur, or an --NH-- group;R.sup.3 is an optionally substituted alkyl or alkenyl radical when X is oxygen or sulphur, or is an optionally substituted alkanoyl radical when X is --NH--;and E is a --CN, --CONH.sub.2, --CSNH.sub.2, or --CONR.sup.4 R.sup.5 group wherein each R.sup.4 and R.sup.5 is an optionally substituted alkyl or alkenyl group.Type: GrantFiled: February 22, 1984Date of Patent: April 1, 1986Assignee: Imperial Chemical Industries PLCInventors: Ian T. Kay, David Bartholomew, Emyr G. Williams, Robert A. Noon
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Patent number: 4551169Abstract: Carbamate derivatives having the formula: ##STR1## wherein X represents an oxygen atom or a sulfur atom and Y represents a --CH-- group or a nitrogen atom; and herbicides utilizing the same.Type: GrantFiled: March 17, 1983Date of Patent: November 5, 1985Assignee: Toyo Soda Manufacturing Company, LimitedInventors: Tetsuo Takematsu, Makoto Konnai, Hideo Morinaka, Yunji Nonaka, Akira Nakanishi
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Patent number: 4532139Abstract: Alkynamide compounds, and pharmaceutically-acceptable salts thereof, of the formula: ##STR1## wherein X is O or S; R is straight or branched alkyne having from 11 to 23 carbon atoms; R.sub.1 is H, OH, or OCH.sub.3 ; R.sub.2 is OH or a short-chain ester; and wherein at least one of R.sub.1 and R.sub.2 is OH or OCH.sub.3. Compositions, useful for producing analgesia in humans or lower animals, comprise a safe and effective amount of: an alkynamide, pharmaceutically-acceptable salts thereof, or mixtures thereof; and a pharmaceutically-acceptable carrier. Preferably, these alkynamides are N-vanillyl-alkynamides. Methods of treatment, comprising administering a safe and effective amount of these alkynamides, pharmaceutically-acceptable salts thereof, or mixtures thereof, include methods of parenteral, oral, and topical administration.Type: GrantFiled: July 14, 1983Date of Patent: July 30, 1985Assignee: The Procter & Gamble CompanyInventors: John M. Janusz, Thomas R. LaHann
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Patent number: 4531968Abstract: Halothiopyruvic amides, which have viricidal and/or fungicidal activity of the formula: ##STR1## wherein X is chloro, fluoro, bromo or iodo; andR is cyclohexyl substituted with 0, 1 or 2 lower alkyl groups, or phenyl substituted with 0, 1 or 2 lower alkyl groups.Type: GrantFiled: March 30, 1984Date of Patent: July 30, 1985Assignee: Chevron Research CompanyInventors: William L. Schinski, Raymond J. Lukens
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Patent number: 4512997Abstract: Novel 4H-1,2,4-triazoles of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be in different positions of the benzene rings and are individually selected from the group consisting of hydrogen, --OH, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, --CF.sub.3, --NO.sub.2, --NH.sub.2 and --NH--AlK and ##STR2## and AlK, AlK.sub.1 and AlK.sub.2 are alkyl of 1 to 4 carbon atoms or R.sub.1 and R.sub.2 together and/or R.sub.3 and R.sub.4 together are methylenedioxy, R is selected from the group consisting hydrogen, alkyl of 1 to 4 carbon atoms, --CH.sub.2 --COOH and --CH.sub.2 --COOAlK.sub.3 and AlK.sub.3 is alkyl of 1 to 4 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having a remarkable analgesic activity and a novel method for their preparation.Type: GrantFiled: November 17, 1983Date of Patent: April 23, 1985Assignee: Roussel UclafInventors: Jean Meier, Francois Clemence
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Patent number: 4460603Abstract: N-[1-(2'-substituted-alkyl)-amidomethyl and carboalkoxymethyl]-substituted-N-acylanilines have fungicidal activity.Type: GrantFiled: July 6, 1981Date of Patent: July 17, 1984Assignee: Chevron Research CompanyInventor: David C. K. Chan
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Patent number: 4459347Abstract: The use of oxythioamido substituted arylhydrazides in producing images in silver halide photographic elements is disclosed. The oxythioamido substituted arylhydrazide can be incorporated in photographic silver halide emulsions. The oxythioamido substituent is capable of promoting adsorption of the arylhydrazide to silver halide grain surfaces. In negative working surface latent image forming emulsions the oxythioamido substituted arylhydrazides permit higher speeds to be achieved. In direct positive internal latent image forming emulsions increased nucleation activity can be achieved.Type: GrantFiled: May 11, 1983Date of Patent: July 10, 1984Assignee: Eastman Kodak CompanyInventors: Richard L. Parton, James A. Friday
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Patent number: 4414221Abstract: The compounds of the formula: ##STR1## wherein R.sup.1 represents phenyl substituted in at least the 2-position by fluorine, chlorine, bromine or iodine, R.sup.2 represents a group R.sup.3, --OR.sup.3, --SR.sup.3 or --NR.sup.3 R.sup.4 where R.sup.3 represents hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, alkenyl of 2 to 6 carbon atoms, cycloalkenyl of 3 to 7 carbon atoms, alkynyl of 2 to 6 carbon atoms, phenyl, phenylalkyl of 7 to 10 carbon atoms or naphthyl, each of which may be unsubstituted or substituted by one or more halogen atoms, alkyl or alkoxy or alkylthio groups of 1 to 6 carbon atoms, nitro groups, cyano groups or mercapto groups, R.sup.4 represents a group as defined for R.sup.Type: GrantFiled: March 20, 1981Date of Patent: November 8, 1983Assignee: FBC LimitedInventors: John H. Parsons, Peter J. West
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Patent number: 4377532Abstract: The invention relates to 3-phenoxybenzyl compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, cyano, --CSNH.sub.2, C.sub.2 -C.sub.3 alkenyl or C.sub.2 -C.sub.3 alkynyl and R.sub.2 is alkenyl or alkynyl, as intermediates for the production of biocides.The preparation of the 3-phenoxybenzaldehydes employed as intermediates is described. Novel 3-phenoxybenzaldehydes used as starting materials and the production thereof are also disclosed.Type: GrantFiled: February 19, 1982Date of Patent: March 22, 1983Assignee: Ciba-Geigy CorporationInventors: Peter Ackermann, Laurenz Gsell, Rudolf Wehrli
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Patent number: 4348523Abstract: Useful thionamide compounds are prepared by reacting sulfur with imines of the structural formula: ##STR1## where R is an alkyl group of 1 to 18 carbon atoms and is other than a phenyl or cyclohexyl group, R.sub.1 and R.sub.2 are alkyl or phenyl groups of 1 to 18 carbon atoms, and R.sub.3 is a phenyl group of 6 to 18 carbon atoms or is hydrogen, in the presence of a diol or triol compound. The total number of carbons in R, R.sub.1, R.sub.2, and R.sub.3 does not exceed 36 in number.Type: GrantFiled: September 8, 1980Date of Patent: September 7, 1982Assignee: Ashland Oil, Inc.Inventor: Theodore C. Shields
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Patent number: 4320142Abstract: Compounds of formula (I) are pesticides active against arthropods. ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 are H, alkyl, alkoxy, halo, CN or CF.sub.3 or two are linked to form a 3 or 4 carbon atom group;X is O or NA where A is H or alkyl;R is H or alkyl;R.sup.4 is H or optionally substituted alkyl, aryl, aralkyl, alkenyl or alkynyl; andR.sup.5 is --CB. R.sup.6 where B is O, S or NR.sup.7 where R.sup.7 is H, alkyl, alkoxy, or optionally substituted aryl or aralkyl;R.sup.6 is H, R.sup.8, OR.sup.8, SR.sup.8 or NR.sup.9 R.sup.10 where R.sup.8 is alkyl, alkenyl or optionally substituted aryl, aralkyl or aryloxyalkyl; and R.sup.9 and R.sup.10 are H, alkyl or optionally substituted aryl or aralkyl;The invention also comprises processes for the preparation of compounds (I), formulations containing them, and their use as pesticides.Type: GrantFiled: May 15, 1980Date of Patent: March 16, 1982Inventors: Malcolm H. Black, Alexander D. Frenkel, Peter T. Roberts
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Patent number: 4282169Abstract: Disclosed are selected 2-acyl- or 2-thioacyl-1-trichloroacetimidoylhydrazines having the formula: ##STR1## wherein X is an atom selected from the group consisting of oxygen and sulfur; and R is a hydrogen, lower alkyl or lower alkoxy group having 1 to 4 carbon atoms, or an unsubstituted or substituted phenyl group. These compounds are disclosed to be agricultural fungicides.Type: GrantFiled: February 19, 1980Date of Patent: August 4, 1981Assignee: Olin CorporationInventors: Eugene F. Rothgery, Lawrence E. Katz