Halogen Attached Directly Or Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/302)
  • Patent number: 5248780
    Abstract: The invention concerns novel, pharmaceutically useful 1,3-dioxane alkenoic acid derivatives of the formula I containing a pyridyl moiety at position 4 of the dioxane ring and in which the groups at positions 2, 4 and 5 have cis-relative stereochemistry, X is hydrogen, alkoxy or hydroxy, Y is vinylene, n is 1 or 2, A.sup.1 is alkylene, R.sup.1 is a variety of substituents defined hereinafter, and R.sup.2 is hydroxy, a physiologically acceptable alcohol residue or alkanesulphonamido, and the pharmaceutically acceptable salts thereof. The invention also includes processes for the manufacture and use of the acid derivatives as well as pharmaceutical compositions for therapeutic use in one or more of a variety of diseases such as ischaemic heart disease, cerebrovascular disease, asthmatic disease and/or inflammatory disease.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: September 28, 1993
    Assignee: Imperial Chemical Industries, Plc
    Inventors: Andrew G. Brewster, George R. Brown, Alan W. Faull, Reginald Jessup, Michael J. Smithers
  • Patent number: 5245040
    Abstract: A process for the preparation of 1,3-disubstituted 2-nitroguanidines of the formula I ##STR1## in which R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl or a radical --CH.sub.2 B; A is an unsubstituted or mono- to tetrasubstituted aromatic or non-aromatic, monocyclic or bicyclic heterocyclic radical, which may contain one or two substituents from the group comprising C.sub.1 -C.sub.3 haloalkyl having 1 to 7 halogen atoms, cyclopropyl, halocyclopropyl having 1 to 3 halogen atoms, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkynyl, C.sub.2 -C.sub.3 haloalkenyl and C.sub.2 -C.sub.3 haloalkynyl having 1 to 4 halogen atoms, C.sub.1 -C.sub.3 haloalkoxy having 1 to 7 halogen atoms, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio having 1 to 7 halogen atoms, allyloxy, propargyloxy, allylthio, propargylthio, haloallyloxy, haloallylthio, cyano and nitro and one to four substituents from the group comprising C.sub.1 -C.sub.3 alkyl, C.sub.
    Type: Grant
    Filed: October 16, 1991
    Date of Patent: September 14, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Maienfisch, Odd Kristiansen, Laurenz Gsell
  • Patent number: 5238908
    Abstract: This invention relates to glutaramic acids and derivatives exhibiting herbicidal activity having the structure ##STR1## wherein A is a carboxylic acid or a derivative thereof, D is CH or N, and R, R.sup.1, R.sup.2, T, X, Y, and Z are as defined within, compositions containing these compounds and methods of controlling weeds with these compounds.
    Type: Grant
    Filed: August 9, 1990
    Date of Patent: August 24, 1993
    Assignee: Rohm and Haas Company
    Inventors: Barry C. Lange, John W. Ashmore, Jane Wissinger-Cornille
  • Patent number: 5234895
    Abstract: Compounds having the formula ##STR1## in which: R.sub.1 is hydrogen or fluoro;R.sub.2 is halo, trihalomethyl, pentahaloethyl, mono- or difluoromethyl, di-, tri- or tetrafluoroethyl, C.sub.1 -C.sub.2 fluoroalkylthio, C.sub.1 -C.sub.2 fluoroalkoxy, methylthio, methylsulfonyl, halomethylsulfonyl, C.sub.1 -C.sub.2 alkyl or methoxy;R.sub.3 is hydrogen or halo;R.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl; C.sub.2 -C.sub.4 alkenyl; C.sub.2 -C.sub.4 alkynyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.2 -C.sub.4 haloalkenyl; C.sub.1 -C.sub.4 alkoxy; C.sub.2 -C.sub.4 alkoxyalkyl, 3-trifluoromethylphenyl, or --(CH.sub.2).sub.n Y;R.sub.5 and R.sub.6 are hydrogen, or R.sub.5 and R.sub.6 together form a bond;R.sub.7 is C.sub.1 -C.sub.4 alkyl;R.sub.8 and R.sub.9 are hydrogen, or R.sub.8 and R.sub.9 together form a bond;Y is cyano; 4-chlorophenyl; C.sub.3 -C.sub.6 cycloalkyl, furyl or tetrahydrofuryl optionally substituted by halo or C.sub.1 -C.sub.4 alkyl; or COR.sub.10 in which R.sub.10 is hydroxy, C.sub.1 -C.sub.5 alkoxy, C.sub.
    Type: Grant
    Filed: June 19, 1992
    Date of Patent: August 10, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventor: Raymond A. Felix
  • Patent number: 5234894
    Abstract: A cyanoketone derivative of the following formula (1) ##STR1## wherein A.sub.1 is a substituted or unsubstituted phenyl or naphthyl group or a substituted or unsubstituted heterocyclic group;each of X.sub.1, X.sub.2 and X.sub.3 is independently an oxygen or sulfur atom;each of B.sub.1, B.sub.2 and B.sub.3 is independently a hydrogen atom or C.sub.1 -C.sub.6 -alkyl group;each of Y.sub.1, Y.sub.2, Y.sub.3 and Y.sub.4 is independently a hydrogen atom, a halogen atom or a C.sub.1 -C.sub.6 -alkyl group; andA.sub.2 is a substituted or unsubstituted group selected from the group consisting of a C.sub.1 -C.sub.6 -alkyl group, a C.sub.2 -C.sub.6 -alkenyl group, a C.sub.2 -C.sub.6 -alkynyl group, a C.sub.1 -C.sub.4 -alkoxy group, a C.sub.1 -C.sub.4 -alkylthio group, a C.sub.1 -C.sub.6 -alkoxycarbonyl group, an unsubstituted benzoyl group, a halogen-substituted benzoyl group, a cyano group or a group as defined in A.sub.1 ;provided that when B.sub.1 is a hydrogen atom and B.sub.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: August 10, 1993
    Assignee: Tokuyama Soda Kabushiki Kaisha
    Inventors: Masahiko Ishizaki, Seiji Nagata, Tadashi Kobutani
  • Patent number: 5232897
    Abstract: Herbicidal pyrimidine compound having the formula ##STR1## wherein the substitutents A, R.sup.1, R.sup.2, X, Y.sup.1, Y.sup.2, Y.sup.3 and Z are as defined herein below.
    Type: Grant
    Filed: November 2, 1992
    Date of Patent: August 3, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsunori Hiratsuka, Naonori Hirata, Kazuo Saitoh, Hideyuki Shibata
  • Patent number: 5229393
    Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein V is an oxygen or a sulphur atom; X and Y, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, nitrile, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, or --COR.sup.6 groups; or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and Z is optionally substituted methylene, optionally substituted amino, oxygen or sulphur and when Z is a substituted methylene group, the substituent may join the 2-position of the phenyl ring to form a non-aromatic fused ring; R.sup.1 and R.
    Type: Grant
    Filed: April 6, 1992
    Date of Patent: July 20, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey
  • Patent number: 5225550
    Abstract: It is possible, by using symmetrical formaldehyde acetals of the formula ##STR1## in which the substituents R.sup.1 -R.sup.3 have the specified meanings, advantageously to introduce the substituent ##STR2## into nitrogen-containing heterocyclic systems to form acyclic nucleoside analogs.
    Type: Grant
    Filed: June 25, 1991
    Date of Patent: July 6, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Gerhard Jahne
  • Patent number: 5223518
    Abstract: This invention relates to 1-phenyl-3-aryl-2-propyne-1-ones, the use of these compounds as calcium uptake inhibitors in leukocytes and thrombocytes, and pharmaceutical compositions containing these compounds as active ingredients, and the process of their preparation.
    Type: Grant
    Filed: June 1, 1992
    Date of Patent: June 29, 1993
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Robert J. Dinerstein, Jeffrey S. Sabol, Keith A. Diekema
  • Patent number: 5216169
    Abstract: A 3-hydroxypyridineazomethine dye represented by general formula (I) ##STR1## wherein R.sub.1 represents an aliphatic group, an aromatic group, or a heterocyclic group; R.sub.2 represents an aliphatic group, an aromatic group, a heterocyclic group, an alkoxy group, an aryloxy group, an alkenyloxy group, an amino group, an acyl group, an ester group, an amido group, a carbamoylamino group, a sulfamoylamino group, a sulfamido group, an imido group, a ureido group, an aliphatic or an aromatic sulfonyl group, an aliphatic or an aromatic thio group, a hydroxyl group, a cyano group, a carboxy group, or a halogen atom; R.sub.3 represents an aryl group; Y represents a bivalent linking group containing at least one of amide bond and ester bond; n represents 0, 1 or 2; where n is 2, the two R.sub.2 groups may be the same group or atom or may be mutually different groups or atoms, or the two R.sub.2 groups may form a ring; where n is 1 or more, R.sub.1 and R.sub.2 may form a ring; and at least one of R.sub.1 and R.sub.
    Type: Grant
    Filed: September 18, 1990
    Date of Patent: June 1, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Shigeru Yamazaki
  • Patent number: 5212317
    Abstract: Processes for making compounds of Formulae XIV, XV, and XVII ##STR1## wherein R.sub.6 is lower alkyl, R.sub.7 is lower alkyl, R is lower alkyl, Y is H, F or Cl, R.sub.8 is a moiety of Formula XVIII ##STR2## wherein n is 1, 2, or 3, R.sub.11 is C.sub.1 -C.sub.4 alkyl and R.sub.12 is the same as R.sub.11, or R.sub.11 and R.sub.12 together form cyclopentane or cyclohexane, and R.sub.13 is:(a) phenyl substituted 1 to 5 times with C.sub.3 -C.sub.7 secondary alkyl or C.sub.4 -C.sub.7 tertiary alkyl, or(b) selected from the group consisting of naphthyl, anthryl, and phenanthryl optionally substituted 1 to 5 times with C.sub.3 -C.sub.7 secondary alkyl or C.sub.4 -C.sub.7 tertiary alkyl groups,R.sub.10 is C.sub.6 -C.sub.10 alkyl, aryl or alkyl aryl,and Y is H, F or Cl,are disclosed. These processes can be used to make optically enhanced and optically pure forms of the compounds, which are useful in the making of camptothecin and analogs thereof.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: May 18, 1993
    Assignee: North Carolina State University
    Inventors: Daniel L. Comins, Matthew F. Baevsky
  • Patent number: 5207819
    Abstract: Disclosed is a novel compound of the formula [I]: ##STR1## (wherein R.sup.1 is H or CH.sub.3, R.sup.2 is H or C.sub.1 -C.sub.4 alkyl), furylmethyl group, tetrahydrofuryl group 2-tetrahydropyranylmethyl group or tetrahydrofurfuryl group which may be substituted with methyl group. The compound has strong herbicidal effect against the weeds belonging to the Family Gramineae.
    Type: Grant
    Filed: June 11, 1990
    Date of Patent: May 4, 1993
    Assignees: Agro-Kanesho Co., Ltd, Tosoh Corporation
    Inventors: Sinzo Someya, Seigo Koura, Mikio Ito, Yoichi Kitamura, Hiroyuki Watanabe, Kenji Tsuzuki
  • Patent number: 5208246
    Abstract: The present invention relates to new tetralones having the formula I: ##STR1## wherein: R.sup.1 and R.sup.2 represent hydrogen, halogen, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, trifluoromethyl, pentafluoroethyl, ethynyl, trimethylsilylethynyl, C.sub.1-4 alkylcarbonylamino being the amino optionally substituted by a C.sub.1-4 alkyl group; R.sup.3 is hydrogen or C.sub.1-4 alkyl, and R.sup.4 is C.sub.1-4 alkyl, or R.sup.3 and R.sup.4 together form a C.sub.2-5 polymethylene chain; either R.sup.5 represents hydroxyl, acetoxy or formyloxy and R.sup.6 and R.sup.7 are both hydrogen, or R.sup.5 together with R.sup.6 form a carbonyl group and R.sup.7 is hydrogen, or R.sup.5 and R.sup.7 together form a bond and R.sup.6 is hydrogen; R.sup.8 is, among others, 1,2-dihydro-2-oxo-1-pyridyl, 2,3-dihydro-1-oxo-1H-isoindol-2-yl, 2-oxo-1-pyrrolidinyl, 2-oxo-1-pyperidinyl. The invention also relates to a procedure for their preparation and to pharmaceutical compositions containing them.
    Type: Grant
    Filed: December 2, 1991
    Date of Patent: May 4, 1993
    Assignee: J. Uriach & Cia.
    Inventors: Carmen Almansa, Carmen Torres, Concepcion Gonzpalez, Elena Carceller, Javier Bartroli
  • Patent number: 5205855
    Abstract: A compound of the formula: ##STR1## wherein Q.sup.1 is CH or N; R is H or C.sub.1 -C.sub.5 alkyl; X is H, halogen, CF.sub.3, or NO.sub.2 ; Y is H or halogen; Z is --O-- or --NH--; A is ##STR2## wherein Q.sup.2, and Q.sup.3 are each CH or N; R.sup.1 and R.sup.2 are each H, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, or C.sub.2 -C.sub.6 alkoxycarbonyl; R.sup.3, R.sup.4, and R.sup.5 are each H or C.sub.1 -C.sub.5 alkyl; R.sup.6 is H, halogen, or C.sub.1 -C.sub.5 alkyl; R.sup.7, R.sup.8, R.sup.9, and R.sup.10 are each H or C.sub.1 -C.sub.5 alkyl; R.sup.11 is H, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.2 -C.sub.6 alkenyl, C.sub.6 -C.sub.10 aryl, C.sub.7 -C.sub.15 aryloxyalkyl, or C.sub.7 -C.sub.15 aralkyl; R.sup.12 and R.sup.13 are each H or C.sub.1 -C.sub.5 alkyl; R.sup.14 is C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.5 -C.sub.10 aryl, or C.sub.7 -C.sub.15 aralkyl; or R.sup.13 and R.sup.14 taken together form C.sub.3 -C.sub.4 alkylene, V.sup.1 and V.sup.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: April 27, 1993
    Assignees: Suntory Limited, Shionogi & Co., Ltd.
    Inventors: Harukazu Fukami, Naoki Higuchi, Naoko Kawaguchi, Masaki Hashimoto, Kinya Ide, Toshio Takahashi
  • Patent number: 5204477
    Abstract: The invention relates to pyridine derivatives of the formula I ##STR1## wherein R.sup.1, A, Z, r, X, s and R.sup.2 have the meaning given in claim 1, and their use as components for liquid crystal media for electrooptical display elements based on the ECB effect.
    Type: Grant
    Filed: November 21, 1990
    Date of Patent: April 20, 1993
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Volker Reiffenrath, Eike Poetsch, Volker Meyer, Herbert Plach
  • Patent number: 5204476
    Abstract: The invention relates to fluorophenylpyridines of the formula I: ##STR1## where R.sup.1 and R.sup.2 are substituted and unsubstituted monovalent organic radicals.
    Type: Grant
    Filed: December 18, 1990
    Date of Patent: April 20, 1993
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Andreas Wachtler, Eike Poetsch, Thomas Geelhaar, Reinhard Hittich, Volker Reiffenrath, Hans-Michael Kompter
  • Patent number: 5200524
    Abstract: Compounds of Formula I ##STR1## are made in accordance with the following scheme: ##STR2## wherein R may be loweralkyl; R.sub.1 may be H, loweralkyl, loweralkoxy, or halo; R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may each independently be H, amino, hydroxy, loweralkyl, loweralkoxy, loweralkylthio, di(loweralkyl)amino, cyano, methylenedioxy, formyl, nitro, halo, trifluormethyl, aminomethyl, azido, amido, hydrazino, or any of the twenty standard amino acids bonded to the A ring via the amino-nitrogen atom; Y is H and W and X are halogen. Also disclosed are novel processes for making starting materials for the scheme given above, and novel intermediate employed in these processes.
    Type: Grant
    Filed: August 10, 1992
    Date of Patent: April 6, 1993
    Assignee: North Carolina State University
    Inventors: Daniel L. Comins, Matthew F. Baevsky
  • Patent number: 5198444
    Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2, CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.dbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1, S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH, ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.
    Type: Grant
    Filed: October 15, 1990
    Date of Patent: March 30, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
  • Patent number: 5198439
    Abstract: The invention concerns pharmaceutically useful novel compounds of the formula I, in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, X and Z have the various meanings defined herein, and their non-toxic salts, and pharmaceutical compositions containing them. The novel compounds are of value in treating conditions such as hypertension and congestive heart failure. The invention further concerns processes for the manufacture of the novel compounds and the use of the compounds in medical treatment.
    Type: Grant
    Filed: April 27, 1992
    Date of Patent: March 30, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: David A. Roberts, Arnold H. Ratcliffe, Robert H. Bradbury
  • Patent number: 5189165
    Abstract: A process for preparing a compound I ##STR1## with A=t-butyl, aryl andR=alkyl, alkenyl, alkynyl, alkenynyl, cycloalkyl(alkyl), aryl, arylalkyl, alkyl-S-(-O)-arylby reacting a compound III ##STR2## with a compound IV ##STR3## under the conditions of a phase-transfer reaction, is described. The process gives excellent yields and is not associated with the unpleasant odor of mercaptans.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: February 23, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Burdinski, Reinhard Kirsch, Hariolf Kottmann
  • Patent number: 5187176
    Abstract: Phenyl substituted heterocyclic compounds having insecticidal activity have the formula (I): ##STR1## wherein R.sup.1 is an optionally substituted pyridone, thiopyridone, pyrimidinthione, pyrimidinone, pyrazole, imidazole or triazole group; R.sup.2 is hydrogen, halogen, haloalkyl, nitro, cyano or a group --CX--NY.sup.1 Y.sup.2 ; R.sup.3 and R.sup.5 are hydrogen, halogen, alkyl or cycloalkyl; R.sup.4 is halogen, haloalkyl, haloalkoxy or S(O).sub.n R.sup.6 ; and Y.sup.1 and Y.sup.2 are independently selected from hydrogen, nitro, amino or optionally substituted alkyl or Y.sup.1 and Y.sup.2 together with the nitrogen to which they are attached form an aliphatic heterocyclic group or form the group .dbd.CHY.sup.3 or Y.sup.1 is hydrogen and Y.sup.2 is alkoxycarbonyl, alkylcarbonyl, optionally substituted aralkyl or --S(O).sub.n R.sup.6.
    Type: Grant
    Filed: October 9, 1991
    Date of Patent: February 16, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Roger Salmon, Raymond L. Sunley, Alan J. Whittle
  • Patent number: 5160662
    Abstract: Optically active compounds having the following formulae (1), (2) or (3) ##STR1## wherein R and R' are C.sub.1-20 alkyl groups; X and Y.sub.1 are --, O, S, or divalent groups such as COO, OOC and OCOO; m is 0 or 1; n is 0 to 5; A.sub.2 is a cyclic group, such as p,p'-biphenylene, 2,6-naphthylene, 2,5-pyrimidinylene-1,4-phenylene, A.sub.1 -Y.sub.2 -pyridylene or A.sub.4 -Y.sub.2 -A.sub.5 ; Y.sub.2 is CH.sub.2 CH.sub.2 or C.tbd.C; A.sub.3 is 2,6-naphthylene, A.sub.1 -Y.sub.2 -pyridylene or A.sub.6 -CH.sub.2 CH.sub.2 -A.sub.7 ; and A.sub.1, A.sub.4, A.sub.5, A.sub.6 and A.sub.7 are cyclic groups, such as 1,4-phenylene and/or 4,4'-biphenylene.
    Type: Grant
    Filed: February 27, 1990
    Date of Patent: November 3, 1992
    Assignee: Sanyo Chemical Industries, Ltd.
    Inventors: Masahiro Satoh, Tetsuya Watanabe, Kunikiyo Yoshio, Hiroshi Kishiki
  • Patent number: 5151428
    Abstract: A pyridine derivative of the formula: ##STR1## wherein R.sup.1 is, the same or different, each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.3 alkoxy gorup, a C.sub.1 -C.sub.3 haloalkoxy group, a cyano group or a nitro group; R.sup.2 is, the same or different, each a hydrogen atom, a halogen atom or a methyl group; R.sup.3 is a halogen atom or a C.sub.1 -C.sub.3 alkyl group; R.sub.4 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group; R.sup.5 is, the same or different, each a halogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.3 haloalkyl group, a C.sub.1 -C.sub.3 alkoxy group or a C.sub.1 -C.sub.3 haloalkoxy group; X is an oxygen atom, a sulfur atom, a carbonyl group, a sulfinyl group, a sulfonyl group, an imino group or a methylene group; Y is an oxygen atom or a sulfur atom; l is an integer of 1 to 5; m is an integer of 1 to 3; and n is an integer of 1 to 4, which is useful for control of insect pest.
    Type: Grant
    Filed: May 24, 1991
    Date of Patent: September 29, 1992
    Inventors: Noriyasu Sakamoto, Hirosi Kisida, Hiroaki Fujimoto, Kimitoshi Umeda, Noritada Matsuo
  • Patent number: 5151436
    Abstract: Therapeutically useful thioformamide derivatives of the formula: ##STR1## wherein R represents alkyl, Het represents pyrid-3-yl, isoquinolin-4-yl, tetrahydroquinolin-3-yl, quinolin-3-yl, pyridazin-4-yl, pyrimid-5-yl, thiazol-5-yl, thieno[2,3-b]-pyridin-5-yl, pyrazin-2-yl, indol-3-yl and thieno[3,2-b]-pyridin-6-yl, Y represents ethylene, methylene or a valency bond, and X represents carbonyl, hydroxymethylene, >C.dbd.NOR.sup.1, >C.dbd.NN(R.sup.1).sub.2 or >C.dbd.NN(R.sup.1)CON(R.sup.1).sub.2 in which R.sup.1 represents hydrogen or optionally substituted alkyl, benzyl, phenethyl, 1-naphthylmethyl, 2-naphthylmethyl or pyrid-3-ylmethyl, or two R.sup.1 substituents on the same nitrogen atom may together form an optionally substituted alkylene radical chain and salts thereof, processes for their preparation and compositions containing them are described.
    Type: Grant
    Filed: August 23, 1990
    Date of Patent: September 29, 1992
    Assignee: Rhone-Poulenc Sante
    Inventors: David C. Cook, Terance W. Hart, Iain M. Mc Lay, Malcolm N. Palfreyman, Brian W. Sharp, Roger J. A. Walsh
  • Patent number: 5149359
    Abstract: The present invention relates to derivatives of 3,4-dehydropiperidin-5-one having herbicidal activity. The derivatives have the formula ##STR1## as defined in the claims. The present invention further relates to a herbicidal composition and a method for controlling weeds which grow among agricultural crops.
    Type: Grant
    Filed: February 21, 1990
    Date of Patent: September 22, 1992
    Assignee: Agrimont S.p.A.
    Inventors: Giovanni Camaggi, Giovanni Meazza, Ciro Preziuso
  • Patent number: 5134066
    Abstract: The deazauracil containing probes of the invention are able to withstand higher temperatures, thereby allowing unmatched probes and mismatched probes to be washed off at higher hybridization stringency, thereby eliminating background readings and improving ease and accuracy of probe use.
    Type: Grant
    Filed: August 29, 1989
    Date of Patent: July 28, 1992
    Assignee: Monsanto Company
    Inventors: Thomas E. Rogers, Steven H. Gray, Balekudru Devadas, Steven P. Adams
  • Patent number: 5132312
    Abstract: Disclosed are novel 3-hydroxy-3-methylglutarylcoenzyme A reductase inhibitors useful as antihypercholesterolemic agents represented by the formula ##STR1## and the corresponding ring-opened hydroxy acids derived therefrom and pharmaceutically acceptable salts thereof.Pharmaceutical compositions containing said compounds and method of inhibiting the biosynthesis of cholesterol therewith are also disclosed.
    Type: Grant
    Filed: November 27, 1990
    Date of Patent: July 21, 1992
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: John R. Regan, Kent E. Neuenschwander
  • Patent number: 5120869
    Abstract: A herbicidal compound of formula (I): ##STR1## wherein X is O, S(O).sub.n or NR.sup.a where R.sup.a is H or alkyl and n is 0, 1 or 2;R.sup.1 is H or halo;R.sup.2 is N or CR.sup.3 where R.sup.3 is halo or NO.sub.2 ;R.sup.4 is H, halo, NO.sub.2, alkyl, haloalkyl, CN, CO.sub.2 alkyl, cycloalkyl, phenyl, COalkyl, COphenyl, CHO,OH, NH.sub.2, NHCOalkyl or alkoxyR.sup.5 is H, halo or optionally substituted alkyl;R.sup.6 is H, halo or optionally substituted alkyl; provided that at least one of R.sup.5 and R.sup.6 is halo;R.sup.7 is CN, CHO, COOR.sup.8, CONR.sup.8 R.sup.9, where R.sup.8 is H, optionally substituted alkyl, alkenyl, alkynyl or aryl and R.sup.9 is a group R.sup.8, SO.sub.2 alkyl, NR.sup.10 R.sup.11 or N.sup.+ R.sup.10 R.sup.11 R.sup.12 Z.sup.- where Z is an agriculturally acceptable anion e.g. chloride and R.sup.10, R.sup.11 and R.sup.12 are independently selected from hydrogen and alkyl. Processes for the preparation of these compounds and compositions containing them are also described.
    Type: Grant
    Filed: November 7, 1989
    Date of Patent: June 9, 1992
    Assignee: Imperial Chemical Industries plc
    Inventor: David Cartwright
  • Patent number: 5110943
    Abstract: The R-enantiomer of a compound of formula I: ##STR1## where Z is an optionally substituted cyclic organic moiety and C* represents an optically active carbon atom, may be prepared by supplying a substrate of formula II ##STR2## to a culture of a microorganism capable of oxidation of compound II into the R-enantiomer of I.
    Type: Grant
    Filed: May 24, 1991
    Date of Patent: May 5, 1992
    Assignee: Shell Internationale Research Maatschappij B.V.
    Inventors: Kenneth H. Clifford, Gareth T. Phillips, Arthur F. Marx
  • Patent number: 5100460
    Abstract: Herbicides of formula: ##STR1## in which: n=0,1, 2f=0,1A is chosen from the groups ##STR2## in which: Ar is chosen from the groups ##STR3## B is chosen from optionally substituted C.sub.1 -C.sub.10 alkyl and C.sub.3 -C.sub.
    Type: Grant
    Filed: July 13, 1989
    Date of Patent: March 31, 1992
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Philippe Desbordes, Michel Euvrard
  • Patent number: 5093373
    Abstract: An ether compound represented by the following formula (I), it production and insecticidal compositions containing it as an active ingredient: ##STR1## wherein R.sub.1, represents a halogen atom or a methyl group; R.sub.2 represents a hydrogen atom or a fluorine atom; R.sub.3 represents a hydrogen atom, a halogen atom or a methyl group; R.sub.4 represents a (C.sub.1 -C.sub.3)alkyl group; Y represents an oxygen atom, a sulfur atom, a methylene group or --NH--; and Z represents a nitrogen atom or --CH.dbd..
    Type: Grant
    Filed: January 22, 1991
    Date of Patent: March 3, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Noritada Matsuo, Hirosi Kisida, Toshihiko Yano
  • Patent number: 5089168
    Abstract: Optically active nitrogen-containing heterocycles of the formula I according to claim 1 are suitable as components for ferroelectric liquid crystalline materials.
    Type: Grant
    Filed: May 16, 1989
    Date of Patent: February 18, 1992
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Joachim Krause, Rudolf Eidenschink, Klaus Bofinger, Reinhard Hopf, Volker Reiffenrath, Eike Poetsch, Bernhard Scheuble, Thomas Geelhaar
  • Patent number: 5089511
    Abstract: A process for the preparation of trifluoromethylvinyl compounds in all their possible steroisomeric forms and mixtures thereof comprising reacting a salt of trifluoroacetic acid with a halovinyl compound in the presence of a cuprous salt to obtain the same stero-specific compound and all possible stero-isomeric forms and mixtures thereof of 1R, trans compounds of the formula ##STR1## wherein R is an alcohol residue used in pyrethrinoid series, or an alcohol residue capable of blocking the acid function, and Z is aryl or haloaryl and the double bond has Z geometry having pesticide activity.
    Type: Grant
    Filed: January 18, 1990
    Date of Patent: February 18, 1992
    Assignee: Roussel Uclaf
    Inventors: Werner Bonin, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 5082853
    Abstract: The subject compounds, which are adapted for the site-specific/sustained delivery of centrally acting drug species to the brain, are compounds of the formula ##STR1## and the non-toxic pharmaceutically acceptable salts thereof, wherein D is the residue of a centrally acting primary, secondary or tertiary amine and ##STR2## is an unsubstituted or substituted dihydropyridyl, dihydroquinolyl or dihydroisoquinolyl radical. The corresponding ionic pyridinium, quinolinium and isoquinolinium salts ##STR3## wherein X.sup.- is the anion of a non-toxic pharmaceutically acceptable acid, are also disclosed.
    Type: Grant
    Filed: April 4, 1990
    Date of Patent: January 21, 1992
    Inventor: Nicholas S. Bodor
  • Patent number: 5079361
    Abstract: Cross-linking reagents which are highly specific for sulphydryl groups and react with thiols at an excellent rate. The essential feature of the reagents is at least one vinyl group conjugated with an armoatic nitrogen heterocycle. Particular examples include vinyl pyridines, vinyl pyrimidines and vinyl triazines.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: January 7, 1992
    Assignee: Celltech Limited
    Inventors: Rikki P. Alexander, Michael A. W. Eaton, Thomas A. Millican, Richard C. D. Titmas
  • Patent number: 5076834
    Abstract: A cyclic amide compound of the formula: ##STR1## wherein X is a hydrogen atom, a halogen atom, a lower alkyl group, a haloalkyl group, a lower alkoxy group, a haloalkoxy group, a lower alkylthio group or a nitro group; Y is a hydrogen atom, a halogen atom, an alkykl roup, a cycloalkyl group, an alkenyl group, an alkylnyl group, a haloalkyl group, a phenyl group, an alkoxy group, a cycloalkoxy group, a cycloalkylalkoxy group, an alkenyloxy group, an alkynloxy group, a benzyloxy group, a phenoxy group, a haloalkoxy group, a lower alkoxy-lower alkoxy group, a cyanoalkoxy group, an alkylthio group, an alkenylthio group, an alkynylthio group, a benzylthio group, a phenylthio group, ##STR2## (wherein W is an oxygen atom or a sulfuratom, R.sup.3 is a hydrogen atom or an alkyl group and R.sup.4 is an alkyl group), ##STR3## (wherein each of R.sup.5 and R.sup.6 is a hydrogen atom or a lower alkyl group), an alkylsulfonyl group, ##STR4## (wherein R.sup.5 and R.sup.
    Type: Grant
    Filed: October 5, 1990
    Date of Patent: December 31, 1991
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuyuki Ohba, Atsuhiko Ikeda, Kenji Matsunari, Yuji Yamada, Michiya Hirata, Yasuo Nakamura, Akira Takeuchi, Hiroyuki Karino
  • Patent number: 5076830
    Abstract: The present invention provides indan-1,3-dione derivatives, including derivatives represented by the following formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents a group represented by ##STR2## wherein E represents a (substituted) phenyl group or a (substituted) pyridyl group; Y represents a hydroxyl group; and Z represents a halogen atom, a (substituted) alkylsulfonyloxy group or a (substituted) phenylsulfonyloxy group, or Y and Z are bonded to represent --O--; and A represents a (substituted) 1,3-butadienylene group or a (substituted) 1,3-azabutadienylene group, and a herbicidal composition containing the same as an active ingredient.The compound of the formula (I) shows high herbicidal activity against gramineous weeds, cyperaceous weeds, etc. but shows markedly low phytotoxicity against crops.
    Type: Grant
    Filed: May 15, 1990
    Date of Patent: December 31, 1991
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tetsuo Jikihara, Toyohiko Shike, Manabu Katsurada, Hisao Watanabe, Osamu Ikeda
  • Patent number: 5071860
    Abstract: Insecticidally active substituted heteroaryl phenyl ethers of the formula ##STR1## in which Het represents an optionally substituted heteroaromatic radical,X represents O, S, --CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 --, --CH.sub.2 --O--, ##STR2## Y represents O, --O--CH.sub.2 -- or S, Z represents an optionally substituted aromatic or heteroaromatic radical;m represents integers from 1-4n represents 0, 1, 2, 3, 4O represents 0, 1, 2, 3, 4, provided than n and o do not simultaneously represent 0p represents integers from 1-4,R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently of one another represent hydrogen, C.sub.1 -C.sub.6 -alkyl which is optionally substituted; two radicals adjacent to one another can also, together with the C atoms to which they are bonded, form a saturated carbocyclic 5- or 6-ring,R.sup.1 represents identical or different radicals hydrogen, halogen, CN, C.sub.1-4 -alkyl, 1-5-halogeno-C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylthio, 1-5-halogeno-C.sub.
    Type: Grant
    Filed: March 7, 1990
    Date of Patent: December 10, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Alig, Wilhelm Stendel, Michael Londershausen
  • Patent number: 5068394
    Abstract: Herbicidal (hetero)aryloxynaphthalene derivatives of the formula ##STR1## in which X is N or --C--R.sup.5,R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are hydrogen or halogen or R.sup.1 may be cyano or trifluoromethyl,R.sup.3 is halogen, trifluoromethyl, trifluoromethoxy, trifluoromethylthio or trifluoromethylsulphonyl,Y is optionally halogen-substituted alkanediyl or alkenediyl, andZ is CN or --CC--Z', whereZ' is halogen, hydroxyl, amine, alkoxy, or the like.Intermediates of the formula ##STR2## are also new.
    Type: Grant
    Filed: October 19, 1989
    Date of Patent: November 26, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roland Andree, Michael Haug, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
  • Patent number: 5068336
    Abstract: A process of producing 2-(4'-hydroxyphenoxy)-3-chloro-5-trifluoromethylpyridine with high efficiency, which is suited for industrial scale production is disclosed. In the process of the present invention, hydroquinone, a dehydrohalogenating agent in the amount of 0.10-0.70 equivalent of the hydroquinone, and a mixed solvent of a polar aprotic solvent and an aromatic hydrocarbon solvent are mixed. The resulting mixture is then heated to reflux at atmospheric pressure to dehydrate the mixture. Then 2,3-dichloro-5-trifluoromethylpyridine in the amount of 0.20-0.95 equivalent of the dehydrohalogenating agent is added to the mixture, and the resulting mixture is allowed to react at a temperature of 100.degree.-170.degree. C.
    Type: Grant
    Filed: February 26, 1990
    Date of Patent: November 26, 1991
    Assignee: Tosoh Corporation
    Inventors: Takumi Kagawa, Takashi Morooka, Kenji Tsuzuki
  • Patent number: 5057527
    Abstract: The present invention relates to the use of substituted alkoxydiphenyl ethers or alkoxydiphenylmethanes of the general formula I ##STR1## in which R.sup.1 represents hydrogen, halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, dioxalkylene, dioxyhalogenoalkylene, CN, NO.sub.2, alkenyl, alkinyl, alkoxyalkyl, alkoxyalkoxy or hydroxyalkoxy,R.sup.2 represents the radicals indicated for R.sup.1,R.sup.3 represents the radicals indicated for R.sup.1,R.sup.4 represents hydrogen, alkyl, halogenoalkyl or halogen,R.sup.5 represents the radicals indicated for R.sup.4,Het represents optionally substituted heteroaryl which is not linked to the remaining radical via the hetero atom,X, Y independently of one another represent --O-- or --S--Z represents --O--, --S--, --CH.sub.2 --, --CHCH.sub.3 -- or --C(CH.sub.3).sub.2 --,m and n independently of one another represent 0, 1, 2 or 3 but their total is equal to, or more than, 2are exceedingly suitable for controlling fleas.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: October 15, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Alig, Wilhelm Stendel, Michael Londershausen
  • Patent number: 5057146
    Abstract: This invention relates to derivatives of acrylic acid useful in agriculture (especially as fungicides but also as plant growth regulators, insecticides and nematocides), to processes for preparing them, to agricultural (especially fungicidal) compositions containing them, and to methods of using them to combat fungi, especially fungal infections in plants, to regulate plant growth and to kill or control insect or nematode pests.The invention provides a compound having the formula (I): ##STR1## and stereoisomers thereof, wherein W is a substituted pyridinyl or substituted pyrimidinyl group linked to A by any of its ring carbon atoms; A is either an oxygen atom or S(O).sub.
    Type: Grant
    Filed: January 17, 1990
    Date of Patent: October 15, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Ian Ferguson, Patrick J. Crowley, Michael G. Hutchings
  • Patent number: 5049673
    Abstract: The present invention discloses a new class of calcium specific fluorescent indicator dyes having visible excitation and emission wavelengths. The new fluorescent indicator dyes combine at least one tricyclic chromophore with a tetracarboxylate parent CA.sup.2+ chelating compound having the octacoordinate pattern of liganding groups characteristic of BAPTA to give a rhodamine-like or fluorescein-like fluorophore. Binding of calcium.sup.2+ increases the fluorescence of the new compounds by up to 40-fold. The calcium.sup.2+ dissociation constants are in the range 0.37-2.3 microM, so that the new indicators give better resolution of high [CA.sup.2+ ] levels than were previously obtainable with predecessor compounds such as quin-2 or fluo-2. The visible excitation wavelengths of the new compounds are more convenient for fluorescent microscopy and flow cytometry than the UV required by previous indicators.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: September 17, 1991
    Assignee: The Regents of the University of California
    Inventors: Roger Y. Tsien, Akwasi Minta
  • Patent number: 5049676
    Abstract: A process for the preparation of optically active esters of 2-chloropropionic acid of the formula: ##STR1## from an optically active lactate of the formula: ##STR2## with inversion of configuration. COOR.sub.1 in formula I and formula II is a hydrolyzable group. The lactate of formula II is brought into contact with SOCl.sub.2, followed by decomposition of the chlorosulfite formed, the process being one in which at least the decomposition stage is carried out in the presence of an ether.
    Type: Grant
    Filed: May 30, 1990
    Date of Patent: September 17, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Pascal Metivier, Harivelo Rajoharisson
  • Patent number: 5049585
    Abstract: Insecticidal compounds with effective knockdown activity against public health pests and having the general formula: ##STR1## wherein Z is selected from 3-allyl-2-methyl-4-oxocyclopent-2-en-1-yl; 3-propargyl-2-methyl-4-oxocyclopent-2-en-1-yl; 1-ethynyl-2-methylpent-2-en-1-yl; 3,4,5,6-tetrahydrophthalimidomethyl; (6-phenoxypyrid-2-yl)methyl; 1-cyano-1-(6-phenoxypyrid-2-yl)methyl; 1-propargylimidazolin-2,4-dione-3-ylmethyl; 5-benzylfur-3-ylmethyl; and a group of formula: ##STR2## wherein X represents hydrogen, hydroxy, methoxy or ethynyl. The invention also provides processes for the preparation of, and insecticidal compositions comprising, the compounds of formula (I).
    Type: Grant
    Filed: October 6, 1989
    Date of Patent: September 17, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Robson, Mark A. Spinney
  • Patent number: 5049675
    Abstract: A solvent-free process for the preparation of herbicidal 2-(4-(pyridinyl-2-oxy)phenoxy)propionate esters is disclosed. The process involves the coupling of a 2-fluoropyridine and an ester of 2-(4-hydroxyphenoxy)propionic acid in the presence of an anhydrous base and in the absence of an added solvent.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: September 17, 1991
    Assignee: DowElanco
    Inventors: Jim Love, Charles B. Grant, Sterling Gatling
  • Patent number: 5034050
    Abstract: Derivatives of 4-((aryloxy)phenoxy)alkenols, their preparation and use as active herbicides for the postemergent control of grassy weeds and especially the control of said weeds in the presence of corn plants are disclosed.
    Type: Grant
    Filed: June 16, 1989
    Date of Patent: July 23, 1991
    Assignee: DowElanco
    Inventors: James A. Turner, Paul S. Zorner, Wendy S. Jacks
  • Patent number: 5032602
    Abstract: For inhibiting HMG-CoA reductase and cholesterol synthesis, the novel 2-pyridones and pyrid-2-thiones of the formula ##STR1## in which A is optionally substituted aryl or heterocyclic,B is optionally substituted alkyl, cycloalkyl or aryl,D and E independently are optionally substituted aryl or heterocyclic, H, nitro, cyano, optionally substituted alkyl, alkenyl or imino, amino, alkoxy or acyl, or forms a ring with B,G is O or S,X is --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--, andR represents a group of the formula ##STR2## and salts thereof.
    Type: Grant
    Filed: November 27, 1989
    Date of Patent: July 16, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Fey, Rolf Angerbauer, Walter Hubsch, Thomas Philipps, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt, Gunter Thomas
  • Patent number: 5032168
    Abstract: Disclosed herein are derivatives of 4-((aryloxy)phenoxy)fluoroalkanoic acid and their use as active herbicides for the pre- and postemergent control of grassy weeds, especially in the presence of broadleaf crops.
    Type: Grant
    Filed: July 10, 1989
    Date of Patent: July 16, 1991
    Assignee: DowElanco
    Inventor: James A. Turner
  • Patent number: 5028732
    Abstract: Compounds having the formula ##STR1## wherein Q is substituted phenyl or substituted pyridyl; Y is nitro, cyano, or halogen; R is a group of the formula --(CHR.sup.1).sub.m --A--(CH.sup.2)--.sub.n --R.sup.3 wherein R.sup.1 and R.sup.2, independently of each other and in each (CHR.sup.1) and (CHR.sup.2) group, are hydrogen, unsubstituted or substituted alkyl, alkoxy, or alkylthio; A is --N(R.sup.1)--, --N(O)--, --O--, --S--, --S(O)--, --S(O).sub.2 --, --C(O)--, --C(O)B--, or --N(H)S(O).sub.2 --; B is alkylene, --O--, --S--, or --N(R.sup.4)--; R.sup.3 is cyano, halogen, or C(O)Z; R.sup.4 is hydrogen or unsubstituted or substituted alkyl; Z is hydrogen, unsubstituted or substituted alkyl, --N(R.sup.4).sub.2, --OR.sup.5, --SR.sup.5, or --N(R.sup.4)SO.sub.2 R.sup.6 ; R.sup.5 is hydrogen, unsubstituted or substituted alkyl, or an agronomically-acceptable cation; R.sup.
    Type: Grant
    Filed: March 13, 1986
    Date of Patent: July 2, 1991
    Assignee: Rohm and Haas Company
    Inventors: Ann H. Beaulieu, Roy Y. Yih