Thiol Or Thioether Containing Patents (Class 568/29)
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Patent number: 4960903Abstract: An aromatic compound having sulfonyl groups, as an intermediate or raw material of polyimides having a good and well-balanced heat resistance and moldability is effectively produced by reacting a compound represented by the general formula,R--Ar--Rwherein Ar is ##STR1## Y is a bond, oxygen atom, sulfur atom, SO.sub.2, CH.sub.2 or ##STR2## and R is a hydrogen atom or --SO.sub.2 X and X is a halogen atom or alkali metal, with a compound represented by the following general formula, ##STR3## wherein X.sup.1 and X.sup.2 are simultaneously methyl groups or form ##STR4## and Z is a hydrogen atom, alkyl group having 1 to 6 carbon atoms or aryl group having 6 to 8 carbon atoms and R.sup.1 is a hydrogen atom, --SO.sub.2 X, halogen atom or nitro group, X is a halogen atom or alkali metal and R and R.sup.1 are not same simultaneously, either of which contains --SO.sub.2 X group as a necessary group.Type: GrantFiled: December 8, 1986Date of Patent: October 2, 1990Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Yoshio Taguchi, Chichiro Imai, Yoshio Imai
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Patent number: 4959488Abstract: Polyfunctional hexasubstituted benzene derivatives wherein at least three of the substituents are saturated carbon chains having from 1 to 21 carbon atoms and functional groups containing hetero functionalities at the ends of the carbon chains and the remainder of the 6 substituents are either saturated carbon chains containing from 1 to 21 carbon atoms or saturated carbon chains containing from 1 to 21 carbon atoms having a functional group including a hetero functional group containing N, O, S, P, or Si at the end of the chains. These derivatives are made by reacting a disubstituted alkyne wherein one or both of the substituents are saturated carbon chains having 1 to 21 carbon atoms to which hetero functional groups are attached with a palladium catalyst and isolating the resulting hexasubstituted benzene derivative.Type: GrantFiled: May 17, 1989Date of Patent: September 25, 1990Assignee: Henkel Research CorporationInventors: James M. Renga, Alan G. Olivero, Mark Bosse
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Patent number: 4957538Abstract: Herbicidal compounds of the structural formula ##STR1## wherein X is oxygen or sulfur; R is chlorine or bromine; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydroxy, hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together are carbonyl (.dbd.0) with the proviso that R.sup.1 , R.sup.2, R.sup.5 and R.sup.6 are all C.sub.1 -C.sub.4 alkyl; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio, or C.sub.1 -C.sub.4 alkylsulfonyl, with the proviso that when R.sup.6 is C.sub.1 -C.sub.4 alkylthio or C.sub.1 -C.sub.4 alkylsulfonyl, then R.sup.3 and R.sup.4 are not together carbonyl; R.sup.7 is methyl or ethyl; and R.sup.8 is (1) halogen; (2) nitro; or (3) R.sup. b SO.sub.n --wherein n is the integer 0 or 2; and R.sup.b is (a) C.sub.1 -C.sub.3 alkyl; and their salts.Type: GrantFiled: November 18, 1988Date of Patent: September 18, 1990Assignee: ICI Americas Inc.Inventor: William J. Michaely
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Patent number: 4946992Abstract: Heteroatom containing perfluoroalkyl terminated neopentyl glycols of the formulas HO[--CH.sub.2 C(CH.sub.2 X--E--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H or HO[--CH.sub.2 C(CH.sub.2 X--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H are prepared from halogenated neopentyl glycols or oxetanes and thiols of the formula R.sub.f --E--SH, amines of the formuls R.sub.f --E--NH--R, alcohols of the formula R.sub.f --E--OH or perfluoro-amides, wherein R.sub.f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms.The polymeric reaction products of said fluorinated diols, and optionally other diols with isocyanates to prepare polyurethanes; with amines and isocyanated to prepare polyureas/polyurethanes; with acids or derivatives to prepare polyesters or polycarbonates are disclosed. These include polymeric, random or block urethane, and/or urea, and/or ester compositions containing the residue of at least one R.sub.Type: GrantFiled: April 14, 1989Date of Patent: August 7, 1990Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Kirtland P. Clark, Athanasios Karydas, Michael Jacobson
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Patent number: 4931474Abstract: An ether derivative compound of the formula: ##STR1## wherein R.sup.1 is hydrogen, chloro, methyl or (C.sub.1 -C.sub.3)-alkoxy, R.sup.2 is (C.sub.1 -C.sub.6)-alkyl, R.sup.3 is hydrogen, chloro, bromo, fluoro, --CF.sub.3, nitro, (C.sub.1 -C.sub.4)-alkyl, methoxy, phenoxy or (C.sub.1 -C.sub.3)-alkylthio, R.sup.4 is hydrogen, chloro or methyl, Y is oxygen, sulfur, sulfinyl, sulfonyl, or imino, x is 0, 1 or 2, y is 0 or 1, a is 0 or 1, b is an integer of 0 to 6, c is 0 or 1, d is 0, 1 or 2, e is 0 or 1, except that all of a, b and c are zero.Type: GrantFiled: July 27, 1987Date of Patent: June 5, 1990Assignee: Nippon Kayaku Kabushiki KaishaInventors: Shoichi Kato, Tatsumi Hayaoka
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Patent number: 4909835Abstract: The invention relates to novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof with herbicidal and plant growth regulating properties.The novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof are of the formula I ##STR1## wherein A is a 2- or 7-membered alkylene bridge, or a 3- to 7-membered alkenylene bridge which may be mono- or polyunsaturated,n is 0, 1 or 2,R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl,R.sub.2 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; or is C.sub.3 -C.sub.6 cycloalkyl; or phenyl, benzyl or phenylethyl, the phenyl ring of each of which may be substituted by ahlogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, cyano or nitro,X is oxygen or a radical --NOR.sub.3, andR.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.Type: GrantFiled: February 24, 1988Date of Patent: March 20, 1990Assignee: Ciba-Geigy CorporationInventor: Hans Tobler
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Patent number: 4898981Abstract: Heteroatom containing perfluoroalkyl terminated neopentyl glycols of the formula HO[--CH.sub.2 C(CH.sub.2 X--E--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H prepared from halogenated neopentyl glycols and thiols of the formula R.sub.f --E--SH, or amines of the formula R.sub.f --E--NH--R wherein R.sub.f is a hydrophonic, olephobic fluoroaliphatic group of up to 20 carbon atoms, E is alkylene of up to 10 carbon atoms, optionally interrupted by up to three groups including --NR, --O, --S--, --SO.sub.2 --, --O.sub.2 C, CONR, and --SO.sub.2 NR, and X is S,SO.sub.2 or NR.sub.2, where R is independently hydrogen, alkyl, or hydroxyalkyl of 1 to 6 carbon atoms are described.The polymeric reaction products of said fluorinated diols, and optionally other diols with isocyanates to prepare polyurethanes; with amines and isocyanates, to prepare polyureas/polyurethanes; with acids or derivatives, to prepare polyesters or polycarbonates are disclosed.Type: GrantFiled: June 20, 1988Date of Patent: February 6, 1990Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Kirtland P. Clark, Athanasios Karydas
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Patent number: 4898944Abstract: Precursors for the preparation of fiber-reactive triphendioxazine dyestuffs correspond to the general formulas: ##STR1## in which Y' is a vinyl, a beta-hydroxyethyl or an ethyl group which contains in the beta-position a substituent which can be eliminated by an alkali;T is an optionally substituted alkyl (e.g.Type: GrantFiled: October 27, 1988Date of Patent: February 6, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunther Schwaiger, Hartmut Springer, Walter Helmling
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Patent number: 4891448Abstract: Polycyclic aromatic compounds, such as biphenyl, are alkylated with an alkylating agent, such as propylene, in the presence of an acidic mordenite zeolite catalyst under conditions sufficient to produce a mixture of substituted polycyclic aromatic compounds enriched in the para alkylated isomers, such as p,p'-di(isopropyl)biphenyl. The novel acidic mordenite catalyst is characterized by its silica/alumina molar ratio, its porosity, and a Symmetry Index. The p,p'-disubstituted isomers of polycyclic aromatic compounds are useful as monomers in the preparation of thermotropic, liquid crystal polymers.Type: GrantFiled: November 23, 1987Date of Patent: January 2, 1990Assignee: The Dow Chemical CompanyInventors: Juan Garces, Joseph J. Maj, G. John Lee, Stephen C. Rocke
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Patent number: 4877899Abstract: Sulfur-substituted alkenyl compounds, synthesis thereof, intermediates therefor, and the use of the compounds to control pests.Type: GrantFiled: November 23, 1983Date of Patent: October 31, 1989Assignee: Sandoz Ltd.Inventors: Robert L. Carney, Thomas L. Brown
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Patent number: 4869748Abstract: Herbicidal compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n - wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; andR.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n - wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)- wherein R.sup.Type: GrantFiled: December 2, 1988Date of Patent: September 26, 1989Assignee: ICI Americas Inc.Inventor: Christopher G. Knudsen
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Patent number: 4867784Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1, R.sup.2, A, m, n, x and y have the meanings given in the disclosure, a process for their manufacture, herbicidal and plant growth-regulating agents containing the novel active ingredients, and processes for combating unwanted plant growth and for regulating plant growth.Type: GrantFiled: January 14, 1987Date of Patent: September 19, 1989Assignee: BASF AktiengesellschaftInventors: Michael Keil, Wolfgang Spiegler, Dieter Jahn, Dieter Kolassa, Ulrich Schirmer, Bruno Wuerzer, Norbert Meyer, Wilhelm Rademacher, Johann Jung
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Patent number: 4845129Abstract: The invention discloses certain diaryl substituted cyclopentane and cyclopentene derivatives useful as PAF inhibitors, pharmaceutical compositions containing said compounds as an active ingredient thereof and a method of using such compositions for inhibiting PAF-induced blood platelet aggregation, PAF-mediated broncho-constriction and extravasation, PAF-induced hypotension, PAF-induced ischemic bowel disease and PAF-mediated, endotoxin induced lug injury.Type: GrantFiled: March 14, 1988Date of Patent: July 4, 1989Assignee: Sandoz Pharm. Corp.Inventors: Robert C. Anderson, William J. Houlihan, Howard C. Smith, Edwin B. Villhauer
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Patent number: 4837352Abstract: An intermediate compound having the structural formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n - wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together can be oxo; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms; R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub. 1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n - wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.Type: GrantFiled: March 21, 1988Date of Patent: June 6, 1989Assignee: Stauffer Chemical CompanyInventor: Christopher G. Knudsen
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Patent number: 4792634Abstract: A method for preparing aryl sulfides by heating an iodoaromatic compound with elemental sulfur at a temperature above about 150.degree. C.Type: GrantFiled: August 20, 1987Date of Patent: December 20, 1988Assignee: Eastman Kodak CompanyInventor: Mark Rule
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Patent number: 4783213Abstract: Compounds of the formula ##STR1## wherein X is oxy, thio, sulfinyl or sulfonyl;R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, or phenyl;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.Type: GrantFiled: August 20, 1987Date of Patent: November 8, 1988Assignee: Stauffer Chemical CompanyInventor: David L. Lee
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Patent number: 4781751Abstract: Compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, halogen, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl, with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.5 is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is halogen, cyano, nitro, trifluoromethyl, --C(O)--OR.sup.f wherein R.sup.f is C.sub.1 -C.sub.4 alkyl, or --C(O)NR.sub.2.sup.b wherein R.sup.b is hydrogen or C.sub.1 -C.sub.2 alkyl;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.Type: GrantFiled: October 2, 1987Date of Patent: November 1, 1988Assignee: Stauffer Chemical CompanyInventor: Hsiao-Ling M. Chin
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Patent number: 4762551Abstract: A compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 can be oxo; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms; and R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.Type: GrantFiled: June 9, 1986Date of Patent: August 9, 1988Assignee: Stauffer Chemical CompanyInventor: Christopher G. Knudsen
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Patent number: 4751240Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined phenolic nucleus including a phenyl-hydroxynaphthyl; hydroxyphenyl-naphthyl; phenyl-hydroxyindanyl, phenyl-hydroxybenzothienyl or mono-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, alkynyl, cycloalkyl, halogenoalkyl, alkoxyalkyl, halogenoalkoxyalkyl, 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--, --(PO)R.sup.2 13 , --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: April 24, 1985Date of Patent: June 14, 1988Assignee: Imperial Chemical Industries PLCInventors: Jean Bowler, Graham C. Crawley, Philip N. Edwards, Alasdair T. Glen, Michael S. Large, Brian S. Tait
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Patent number: 4744812Abstract: Substituted diphenyl ethers of the formula ##STR1## where Z.sub.1, Z.sub.2 and Z.sub.3 are hydrogen, halogen, nitro, cyano, carboxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylmercapto, haloalkylmercapto, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl or haloalkylsulfonyl, Z.sub.4 is hydrogen, cyano, alkyl, alkoxy, acetoxy or alkylmercapto, Y is hydrogen, halogen, cyano or nitro, X is oxygen, sulfur, sulfinyl or sulfonyl, and A is hydrogen, unsubstituted or substituted alkyl ##STR2## and can also be sulfonyl ##STR3## when X is oxygen, and, when Z.sub.4 is alkoxy or alkylmercapto, can also be a methylene chain --(CH.sub.2).sub.m -- by which the radicals Z.sub.4 --CH--X-- are bonded to form a ring, R.sub.1 is hydrogen, methyl, ethyl or n-propyl, R.sub.2 is cyano, methoxy, ethoxy or ##STR4## where B is OH, ONa, O--alkyl, unsubstituted or substituted phenoxy, --NH.sub.2, --NH--alkyl or --N(alkyl).sub.2, n is 1, 2 or 3, R.sub.3 and R.sub.Type: GrantFiled: March 4, 1985Date of Patent: May 17, 1988Assignee: BASF AktiengesellschaftInventors: Adolf Parg, Bruno Wuerzer, Gerhard Hamprecht
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Patent number: 4732912Abstract: 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: April 27, 1984Date of Patent: March 22, 1988Assignee: 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: 4724267Abstract: Bis(haloacylaromatic) compounds have been made by a new process in which monohaloacylated aromatic compounds have been reacted by a coupling reaction. These bis(haloacylaromatic) compounds can be employed as monomers in the preparation of polyesters and polyamides which have easy processability. The monohaloacylated compound is coupled by reacting two moles of the monomer with a carbon or sulfur compound containing at least two halogen atoms in the presence of a Friedel-Crafts catalyst.Type: GrantFiled: May 23, 1986Date of Patent: February 9, 1988Assignee: The Dow Chemical CompanyInventors: George M. St. George, Marlin E. Walters
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Patent number: 4724263Abstract: Compounds of the formula ##STR1## wherein R is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.m --wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are methyl or ethyl;R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)--wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.Type: GrantFiled: June 9, 1986Date of Patent: February 9, 1988Assignee: Stauffer Chemical CompanyInventor: Charles G. Carter
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Patent number: 4721814Abstract: Compounds of formula I or II ##STR1## in which formulae R.sup.1 and R.sup.2 are each independently of the other hydrogen, alkyl, alkenylmethyl, cyclohexyl, phenyl, benzyl or tolyl, or are a --CH.sub.2 CHR.sup.3 --CH.sub.2 --S--H group, R.sup.3 and R.sup.4 are each independently of the other hydrogen or methyl, X is alkylene, --S--, --SO--, --SO.sub.2 -- or substituted alkylene, R.sup.5 and R.sup.6 are each independently of the other hydrogen or alkyl, R.sup.8 is hydrogen, alkyl, alkenylmethyl or phenyl, and wherein n is an integer from 1 to 10, can be used as hardeners for epoxy resins.The compositions containing epoxy resins and these hardeners are particularly suitable for use as adhesive formulations. The cured products have good moisture resistance.Type: GrantFiled: January 16, 1987Date of Patent: January 26, 1988Assignee: Ciba-Geigy CorporationInventors: Sheik A. Zahir, Karl Mechera
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Patent number: 4681621Abstract: Compounds of the formula ##STR1## wherein R is halogen, preferably chlorine or bromine; C.sub.1 -C.sub.4 alkoxy, preferably methoxy; nitro; cyano; --S(O).sub.n R' wherein n is the integer 0, 1 or 2, preferably 2 and R' is C.sub.1 -C.sub.4 alkyl, preferably methyl; or R is C.sub.1 -C.sub.4 alkyl or methyl and most preferably R is chlorine, bromine, methoxy, nitro, methyl or CF.sub.3 ; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or ##STR2## wherein R.sup.a is C.sub.1 -C.sub.4 alkyl; R.sup.1 and R.sup.2 together are alkylene having 3 to 6 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; and R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) OCF.sub.3 ; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1, or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.Type: GrantFiled: December 3, 1985Date of Patent: July 21, 1987Assignee: Stauffer Chemical CompanyInventors: David L. Lee, William J. Michaely
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Patent number: 4642383Abstract: Substituted 2,2'-dihydroxydiphenyl sulfide, sulfoxide, and sulfone compounds, and their use as azo coupling components in light-sensitive diazo compositions. The novel compounds couple with rapidly developing diazonium compounds to provide lemon-yellow dyes, and can be used in combination with blue and violet couplers to provide a green-black diazo image in higher density areas with a neutral black in lower density areas.Type: GrantFiled: September 30, 1982Date of Patent: February 10, 1987Assignee: James River Graphics, Inc.Inventor: Robert C. Desjarlais
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Patent number: 4625066Abstract: Novel substituted acetylene-ketones of the formulaR.sup.2 --C.tbd.C--CO--R.sup.1 (I)in whichR.sup.1 represents optionally substituted cycloalkyl with 4 to 7 carbon atoms or the groupings ##STR1## or represents optionally substituted aryl, if R.sup.2 represents optionally substituted cycloalkenyl or optionally substituted cycloalkylalkyl;R.sup.2 represents alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkylalkyl, optionally substituted aryl or optionally substituted aralkyl;R.sup.3 represents halogen;R.sup.4 represents hydrogen or halogen;R.sup.5 represents alkyl with more than 1 carbon atom, alkenyl, alkinyl or the CHO group or a derivative thereof, or represents methyl, if R.sup.2 represents optionally substituted cycloalkenyl or optionally substituted cycloalkylalkyl;R.sup.6 represents cyano, optionally substituted aryl or the groupings --XR.sup.7 or --CONR.sup.8 R.sup.9 ;R.sup.Type: GrantFiled: November 29, 1984Date of Patent: November 25, 1986Assignee: Bayer AktiengesellschaftInventor: Hans-Ludwig Elbe
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Patent number: 4621098Abstract: The present invention provides thioethers of the general formula: ##STR1## wherein Ar is a phenyl radical which is optionally substituted one, two or three times by alkyl, alkenyl, alkoxy, alkylthio, alkanoyl, hydroxyl, hydroxyalkyl, carboxyl, alkoxycarbonyl, carbamoyl, nitro, amino or halogen, Q is an oxygen or sulphur atom or an NH group, A is a straight-chained or branched C.sub.2 -C.sub.8 alkylene radical which is optionally substituted by a hydroxyl group or can be interrupted by an ethenylene or ethynylene group, n is 0, 1 or 2, and R is a hydrogen atom or a straight-chained or branched alkyl radical which is optionally substituted one or more times by the same or different radicals selected from alkoxycarbonyl, alkoxy, hydroxyl, carboxyl or optionally substituted carbamoyl or amino; as well as the pharmacologically acceptable salts thereof, with the proviso that A cannot be ethylene when Ar is a phenyl radical, Q is an oxygen atom and R is the group --CH.sub.2 COOH.Type: GrantFiled: July 2, 1984Date of Patent: November 4, 1986Assignee: Boehringer Mannheim GmbHInventors: Robert Umminger, Walter-Gunar Friebe, Wolfgang Kampe, Androniki Roesch, Otto-Henning Wilhelms
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Patent number: 4595721Abstract: Additives for rubber compositions, giving vulcanizates having improved retention of optimum physical properties, are compounds having the formula R-S-B-S-R where B is an organic bridging group and R is an electron-withdrawing group, for example CN, CCl.sub.3, a radical containing an activated methylene group linked to the sulphur atom or the enolic tautomer of a keto-activated methylene group. Also useful as stabilizing agents are oligomeric analogues of such compounds.Type: GrantFiled: June 4, 1984Date of Patent: June 17, 1986Assignee: Monsanto Europe, S.A.Inventors: Albert F. L. G. Devaux, Philippe G. Moniotte
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Patent number: 4588433Abstract: Phenoxymethane derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, halogen, alkoxycarbonyl, cycloalkoxycarbonyl or nitro,R.sup.2 represents hydrogen, alkyl or halogen,R.sup.3 represents hydrogen, alkyl, alkenyl, alkinyl, phenyl which is optionally substituted by alkyl and/or halogen, phenylalkyl which is optionally substituted by alkyl and/or halogen, alkoxy, phenoxy, halogenoalkyl, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphonyl, phenylthio, phenylsulphonyl, nitro or halogen,R.sup.Type: GrantFiled: February 21, 1984Date of Patent: May 13, 1986Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Schmitt, Klaus Lurssen, Karlfried Wedemeyer
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Patent number: 4552984Abstract: A process for the preparation of .alpha.,.alpha.-difluoroalkoxy or .alpha.,.alpha.-difluoroalkylthiophenyl sulfones, in which a polyhaloalkoxybenzene or a polyhaloalkylthiobenzene is reacted with a sulfonic acid, a derivative or a precursor of this acid, in the presence of boron trifluoride in an amount such that the absolute pressure of the boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent. The resultant products are useful as intermediates in the synthesis of compounds having a phytosanitary (e.g., herbicidal) or pharmaceutical activity.Type: GrantFiled: June 28, 1982Date of Patent: November 12, 1985Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4547592Abstract: Arylether compounds containing terminal phenylethynyl groups are provided. Also provided is a process for producing these compounds. The following compounds are claimed; 4,4'-bis(3-phenylethynyl-phenoxy) diphenylsulfone; 2,2-bis[([([3-phenoxy]-3-phenoxy)-3-phenylethynyl]-3-phenoxy)-4-phenyl]-pr opane and 2,2-bis[([([3-phenoxy]-3-phenoxy)-3-phenyl ethynyl]-3-phenoxy)-4-phenyl]-hexafluoropropane.Type: GrantFiled: July 25, 1984Date of Patent: October 15, 1985Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Bruce A. Reinhardt, Fred E. Arnold, Marilyn R. Unroe
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Patent number: 4539159Abstract: An improved process for preparing derivatives of mercaptophenols containing nitrile, carbonyl, sulphone or ester groups characterized by reacting the components in a polar solvent with an amine catalyst. The catalyst can be removed from the product by co-distillation with the solvent to leave a relatively pure product free of contaminant without the need for further purification steps. The preferred amine catalysts are tertiary amines.Type: GrantFiled: April 23, 1984Date of Patent: September 3, 1985Assignee: The Dow Chemical CompanyInventor: Mark R. Johnson
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Patent number: 4433183Abstract: Multistep process for preparing (+)-p-mentha-2,8-dien-1-ol from (+)-(R)-limonene. New compounds useful as intermediates in said process.Type: GrantFiled: April 8, 1982Date of Patent: February 21, 1984Assignee: Firmenich SAInventors: Charles Fehr, Gunther Ochloff
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Patent number: 4429153Abstract: This invention relates to novel cyclopropane derivatives useful as insecticides, to processes for their preparation, to compositions comprising them and to methods of combatting insect and similar invertebrate pests using them.Type: GrantFiled: January 15, 1982Date of Patent: January 31, 1984Assignee: Imperial Chemical Industries PLCInventor: Nazim Punja
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Patent number: 4429162Abstract: The instant invention relates to compounds of the formula ##STR1## wherein each R.sub.f is independently straight or branched chain perfluoroalkyl of 2 to 18 carbon atoms or perfluoroalkoxy-perfluoroalkyl of 4 to 18 carbon atoms;each R.sub.1 is independently straight or branched chain alkylene of 1 to 12 carbon atoms, alkylenethioalkylene of 2 to 12 carbon atoms, alkyleneoxyalkylene of 2 to 12 carbon atoms, or alkyleneiminoalkylene of 2 to 12 carbon atoms where the imino nitrogen atom contains as a third substituent, hydrogen or alkyl of 1 to 6 carbon atoms;R.sub.2, R.sub.3 and R.sub.4 are independently hydrogen, chloro, bromo, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, hydroxyalkyl of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms, and R.sub.2 and R.sub.3 additionally may, together with the carbon atoms to which they are attached, form a fused benzo ring;R.sub.Type: GrantFiled: February 1, 1982Date of Patent: January 31, 1984Assignee: Ciba-Geigy CorporationInventors: Thomas W. Cooke, Robert A. Falk
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Patent number: 4399313Abstract: Non-ionic products of the formula:R--X--[C.sub.2 H.sub.3 (OCH.sub.2 CH.sub.2).sub.n (OH)--CH.sub.2 --Y--R'in which R and R' denote alkyl or alkenyl radicals having from 6 to 20 carbon atoms, the sum of the numbers of carbon atoms in R and R' being 24 to 32; X denotes an oxygen atom, a sulphur atom or a sulphoxide group; Y denotes a sulphur atom, a sulphoxide group or a methylene group (if Y denotes methylene, the sum of the numbers of carbon atoms in R and R' is 22 to 30); and n denotes an integer or decimal number from 1 to 40 are disclosed. These non-ionic compounds are suitable for use in pharmaceutical or cosmetic applications, in particular for the care of the skin or hair.Type: GrantFiled: October 14, 1980Date of Patent: August 16, 1983Assignee: Societe Anonyme dite: L'OrealInventors: Guy Vanlerberghe, Henri Sebag
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Patent number: 4393079Abstract: Anti-inflammatory compositions are prepared which comprise a therapeutically effective amount of a compound of the formula ##STR1## wherein X is CO or CHOH; Y is CO; the dotted line represents a double bond which is present or absent; R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxyl, hydroxyl, acetoxyl, nitro or amino; R.sub.3 is alkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms, cycloalkenyl of 5 to 8 carbon atoms or phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxyl, ethoxyl, benzyloyl, hydroxyl, acetoxyl, trifluoromethyl, nitro, amino, acetyl, methylthiol, methylsulphonyl, methylamino and dimethylamino. Compounds of formula I above are also novel.Type: GrantFiled: December 15, 1976Date of Patent: July 12, 1983Assignee: Beecham Group LimitedInventors: William G. Cole, Alexander C. Goudie, Carl J. Rose
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Patent number: 4358308Abstract: The 4-perfluoroacetyl-, 4-perfluoromethylthio-, 4-perfluoromethylsulfinyl-, and 4-perfluoromethylsulfonyl-4'-nitrodiphenyl ethers comprise a class of compounds that are highly effective herbicides.Type: GrantFiled: October 19, 1981Date of Patent: November 9, 1982Assignee: Rohm and Haas CompanyInventor: Colin Swithenbank
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Patent number: 4349568Abstract: Novel compounds exhibiting antiviral activity are disclosed, such compounds are represented by the formula: ##STR1## wherein m represents the integer 0, 1 or 2; R represents trihalomethyl, alkyl or phenyl; R.sub.1 represents hydrogen, bromo, chloro, fluoro, cyano, nitro, amino, alkyl, alkoxy or trifluoromethyl; R.sub.2 represents hydroxyl, bromo, chloro, fluoro, cyano, acetyl, benzoyl, substituted benzoyl, alkyl, alkoxy, substituted alkoxy, benzyl, substituted benzyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, or the radical --O(CH.sub.2).sub.n R.sub.4 wherein n represents the integer 1, 2 or 3 and R.sub.4 represents cyano or dialkylamino; R.sub.3 represents hydrogen, hydroxyl, bromo, chloro, fluoro, cyano, acetyl, benzoyl, substituted benzoyl, alkyl, alkoxy, substituted alkoxy, benzyl, substituted benzyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, or the radical --O(CH.sub.2).sub.n R.sub.Type: GrantFiled: June 12, 1980Date of Patent: September 14, 1982Assignee: The Dow Chemical CompanyInventors: Lowell D. Markley, Yulan C. Tong, Steven G. Wood
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Patent number: 4338122Abstract: 2-Aryl-1,3-cyclopentanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal and acaricidal activity.Type: GrantFiled: October 16, 1980Date of Patent: July 6, 1982Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4335142Abstract: A microbicide having the general formula ##STR1## wherein R is a halomethyl radical, or a methylene radical; W is cyclohexyl, phenyl or meta or para substituted phenyl wherein the substituents are C.sub.1 -C.sub.4 alkyl, halogen or nitro; X and Y is hydrogen, C.sub.1 -C.sub.4 alkyl, halogen or nitro; provided that when R is halomethyl n is 1 and when R is methylene n is 0.Type: GrantFiled: September 11, 1979Date of Patent: June 15, 1982Assignee: Uniroyal, Inc.Inventors: Douglas I. Relyea, Robert A. Davis
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Patent number: 4331814Abstract: Sulphones useful for preparing polyenes have the formula: ##STR1## where the sulphonyl group replaces a hydrogen atom on carbon atom (a) or (b), R represents alkyl, aralkyl or aryl, optionally substituted, A and Q represent an optionally substituted hydrocarbon of 5n+1 carbon atoms (n is 1-5), methyl, optionally substituted by halogen, sulphide or sulphone, CH.sub.2 OH (or an ether or ester thereof), CHO (optionally protected), COOH (or an acid chloride, ester or nitrile thereof), with the proviso that when A represents a 2-(2,6,6-trimethylcyclohex-1-enyl) ethenyl radical, Q cannot represent --COOH or an ester thereof.Type: GrantFiled: February 1, 1973Date of Patent: May 25, 1982Assignee: Rhone Poulenc S.A.Inventors: Pierre Chabardes, Marc Julia, Albert Menet
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Patent number: 4321080Abstract: 1-Halo-2-alkylthioethyl and 1-halo-2-arylthioethyl sulfones, having algicidal and fungicidal activity, are prepared by the addition of arylsulfenyl or alkylsulfenyl halides to alkyl or aryl vinyl sulfones. The thioethyl sulfone products are treated with a base to produce 2-alkylthiovinyl or 2-arylthiovinyl sulfones, which also have algicidal and fungicidal activity. The vinyl sulfones are halogenated to produce 1,2-dihalothioethyl sulfones, which have superior fungicidal activity, especially for tomato and celery late blight.Type: GrantFiled: August 11, 1980Date of Patent: March 23, 1982Assignee: Chevron Research CompanyInventor: Philip S. Magee
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Patent number: 4283348Abstract: 2-Aryl-1,3-cyclopentanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal and acaricidal activity.Type: GrantFiled: September 26, 1979Date of Patent: August 11, 1981Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4256659Abstract: 2-Aryl-1,3-cyclohexanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal, miticidal and mite ovicidal activity.Type: GrantFiled: January 22, 1980Date of Patent: March 17, 1981Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4256657Abstract: 2-Aryl-1,3-cyclohexanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal, miticidal and mite ovicidal activity.Type: GrantFiled: January 22, 1980Date of Patent: March 17, 1981Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4256658Abstract: 2-Aryl-1,3-cyclohexanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal, miticidal and mite ovicidal activity.Type: GrantFiled: January 22, 1980Date of Patent: March 17, 1981Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4209532Abstract: 2-Aryl-1,3-cyclohexanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal, miticidal and mite ovicidal activity.Type: GrantFiled: March 28, 1977Date of Patent: June 24, 1980Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler