Halogen Attached Directly Or Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/302)
  • Patent number: 4826987
    Abstract: The present invention relates to compounds of formula I ##STR1## in which formula I X stands for O, S, ##STR2## R.sub.1 and R.sub.2 which can be the same or different stand for hydrogen, straight or branched, saturated or unsaturated, unsubstituted or substituted C.sub.1 -C.sub.8 -alkyl, or for ar-C.sub.1 -C.sub.4 -alkyl, aryl and ar being unsubstituted or substituted phenyl; R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are the same or different and stand for hydrogen, halogen, pseudo halogen, cyano, nitro, amino, carboxy, hydroxy, alkyl, alkoxy; or R.sub.5 and R.sub.6 form an aromatic ring which is fused to the pyridyl ring, and which aromatic ring may substituted; provided that R.sub.1 and R.sub.2 cannot be hydrogen at the same time, and provided that when R.sub.5 and R.sub.6 both are chlorine and R.sub.1 is hydrogen, then R.sub.2 cannot be n-propyl; and salts and bioreversible derivatives thereof.
    Type: Grant
    Filed: February 28, 1986
    Date of Patent: May 2, 1989
    Assignee: Leo Pharmaceutical Products Ltd.
    Inventors: Ole Bent Iv rmose Nielsen, Ian Ahnfelt-Ronne
  • Patent number: 4826531
    Abstract: Acrylic acid derivatives having the formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, R.sup.1 and R.sup.2 are alkyl or fluoroalkyl groups, and Z is oxygen or sulphur; A, B, D and E are hydrogen, halogen, hydroxy or optionally substituted alkyl, alkoxy, aralkyl, arylalkoxy, alkenyl, alkynyl, aryl, aryloxy, arylthio, heteroaryloxy, heteroarylthio, acyloxy, amino, arylazo or acylamino, nitro, cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 .dbd.NR.sup.4, --N.dbd.CR.sup.3 R.sup.4 or --S(O).sub.n R.sup.3 groups; any two of the groups A, B, D and E, when they are in adjacent positions on the ring, optionally join to form a fused ring, n is 0, 1 or 2; and R.sup.3 and R.sup.4 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl or optionally substituted aryl or aralkyl; and metal complexes thereof. These compounds are useful as fungicides, insecticides, nematicides or plant growth regulators.
    Type: Grant
    Filed: April 17, 1987
    Date of Patent: May 2, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
  • Patent number: 4822806
    Abstract: The invention relates to .alpha.-methyl-(6-phenoxy)-2-picolyl cyclopropanecarboxylates of the formula ##STR1## wherein X.sub.1 is methyl or halogen,R.sub.1 is hydrogen or halogen, andR.sub.2 is hydrogen, halogen, 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, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, nitro or cyano.The invention also relates to the preparation of these esters and to the use thereof in pest control.
    Type: Grant
    Filed: January 12, 1987
    Date of Patent: April 18, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Ackermann
  • Patent number: 4820839
    Abstract: Nitrogen-containing heterocyclic esters of the formula I,R.sup.1 -A.sup.1 -Z.sup.1 -A.sup.2 -[Z.sup.2 -A.sup.3 ].sub.m -R.sup.2 Iin which R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and m have the meaning specified in patent claim 1, are suitable as components of smectic liquid-crystalline phases.
    Type: Grant
    Filed: January 23, 1987
    Date of Patent: April 11, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Joachim Krause, Andreas Wachtler, Volker Reiffenrath, Bernhard Scheuble, Reinhard Hittich
  • Patent number: 4814340
    Abstract: The present invention relates to novel aromatic alkane derivatives represented by the following general formula (I): ##STR1## wherein Ar stands for a substituted or unsubstituted phenyl or naphtyl group, R.sup.1 stands for a methyl, ethyl or isopropyl group and R.sup.2 stands for a hydrogen atom or a methyl group, or R.sup.1 and R.sup.2 together with the carbon to which they are attached jointly represent a substituted or unsubstituted cycloalkyl group, and R.sup.3 stands for a fundamental group of an alcohol which is usually used in a form of R.sup.3 OH as to natural or synthetic pyrethroids, and also to processes for the preparation of these compounds and the uses of these compounds.These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicities of these compounds are very low.
    Type: Grant
    Filed: November 6, 1986
    Date of Patent: March 21, 1989
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Nakatani Kiyoshi, Satoshi Numata, Kenji Kodaka, Kengo Oda, Shiro Shiraishi, Takatoshi Udagawa
  • Patent number: 4808762
    Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; Z is oxygen, sulfur, or methylene; and Ar' is 2-methyl[1,1'-biphenyl]-3-yl, 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, or 6-phenoxy-2-pyridyl exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively harmless to aquatic fauna.
    Type: Grant
    Filed: September 9, 1987
    Date of Patent: February 28, 1989
    Assignee: FMC Corporation
    Inventors: Gary A. Meier, Scott M. Sieburth, Thomas G. Cullen, John F. Engel
  • Patent number: 4806553
    Abstract: There are provided insecticidally active alkylenediamines of the formula ##STR1## wherein W.sup.1 stands for a 5- or 6-membered heterocyclic group which may be substituted, containing at least one hetero atom selected from, O, S and N, R.sup.1, R.sup.2 and R.sup.3 are hydrogen or alkyl and R.sup.4, X, Y and Z have the meanings as given in the specification.The new alkylenediamines can be prepared according to different preparation methods and exhibit a strong insecticidal activity.
    Type: Grant
    Filed: June 18, 1987
    Date of Patent: February 21, 1989
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Shoko Sasaki, Koichi Moriya, Yumi Hattori
  • Patent number: 4797409
    Abstract: New 1-hydroxy-2-pyridones of the general formula I ##STR1## in which R.sup.1, R.sup.2 and R.sup.3, which are identical or different, denote hydrogen or lower alkyl having 1-4 carbon atoms, R.sup.1 and R.sup.3 preferably being hydrogen, and R.sup.2 preferably being methyl,X denotes S or, preferably, O,Y denotes hydrogen or up to 2 halogen atoms, namely chlorine and/or bromine,Z denotes a single bond or the bivalent radicals O, S, --CR.sub.2 -- (R=H or C.sub.1 -C.sub.4 -alkyl) or other 2-valent radicals with 2-10 carbon and, optionally, oxygen and/or sulfur atoms linked to form a chain, it being obligatory when the radicals contain 2 or more oxygen and/or sulfur atoms for the latter to be separated by at least 2 carbon atoms, and it being possible for 2 adjacent carbon atoms also to be linked together by a double bond, and the free valencies of the carbon atoms being saturated by H and/or C.sub.1 -C.sub.
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: January 10, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Lohaus, Walter Dittmar, Heinz Hanel, Wolfgang Raether, Dieter Reuschling, Bengt-Thomas Grobel
  • Patent number: 4792616
    Abstract: Novel diaryl ethers of the formula ##STR1## wherein A is CR.sup.3 or N and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, n and R.sup.6 are as defined hereinafter, processes for their preparation, herbicidal compositions which contain these compounds as the active ingredient as well as the use of these compounds or compositions for the control of weeds is disclosed.
    Type: Grant
    Filed: April 17, 1986
    Date of Patent: December 20, 1988
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Paul Winternitz, Ren/e/ Zurfl/u/ h
  • Patent number: 4792606
    Abstract: A process for the preparation of a dimeric aromatic acyl cyanide of the formula ##STR1## in which Ar is optionally substituted phenyl, naphthyl or hetaryl,comprising reaction an acyl halide of the formulaAr--CO--Halin whichHal is fluorine, chlorine or bromine, with an alkali metal cyanide in a two-phase system comprising water and a water-immiscible or only sparingly water-miscible aliphatic ketone, and in the presence of a phase-transfer catalyst. The products are known intermediates for pesticides.
    Type: Grant
    Filed: July 16, 1987
    Date of Patent: December 20, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Hermann-Dieter Krall
  • Patent number: 4792563
    Abstract: Insecticidally active compounds of the formula (I): ##STR1## wherein R.sup.4 represents a group selected from those groups represented by R.sup.5 in insecticidally active compounds of formula: ##STR2## R.sup.3 is selected from fluoromethyl and difluoromethyl, and either (a) R.sup.1 and R.sup.2 represent alkyl of one, two, three or four carbon atoms, or (b) R.sup.1 and R.sup.2 taken together with the adjacent carbon atom form a cycloalkyl ring of four, five or six carbon atoms.
    Type: Grant
    Filed: October 6, 1987
    Date of Patent: December 20, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventor: Alan J. Whittle
  • Patent number: 4790870
    Abstract: This invention relates to aryloxy optionally oxo-substituted indane or tetralin derivatives having herbicidal activity and to the use of such compounds to control the growth of noxious plants, i.e., weeds.
    Type: Grant
    Filed: May 1, 1987
    Date of Patent: December 13, 1988
    Assignee: PPG Industries, Inc.
    Inventors: David A. Hunt, James A. Schwindeman
  • Patent number: 4791123
    Abstract: There are provided new alkane and alkoxyalkane derivatives of the general formula I ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and A have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.
    Type: Grant
    Filed: January 22, 1987
    Date of Patent: December 13, 1988
    Assignee: Schering Akt.
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien, Dietrich Baumert, David Giles
  • Patent number: 4788206
    Abstract: Compounds of the formula ##STR1## Y is O ir S, *A is paraphenylene or *----(CH.sub.2)n----(X).sub.m --(CH.sub.2).sub.r ----, X is O, S or --CH.dbd.CH--, n or r, independently, are integers from 0 to 3, s is an integer from 0 to 1, m is an integer from 0 to 1, provided that when m is 1, n+s must be at least 2, R.sub.1 and R.sub.2, independently, are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, Het, aryl, R.sub.3, R.sub.4 and R.sub.8, independently, are hydrogen, lower alkyl, aryl, R.sub.5 and R.sub.6, independently, are hydrogen or lower alkyl, R.sub.7 is hydrogen, lower alkyl, cycloalkyl, Het-lower alkyl or aryl, Het is a monocyclic 5- or 6-membered hetero aromatic or a bicyclic heteroaromatic radical containing one or two hetero atoms selected from nitrogen, oxygen and sulfur, which radical may be substituted by lower alkyl, halogen or aryl, and the asterisk denotes the point of attachment,and when R.sub.6 and R.sub.7 are different, their enantiomers and racemic mixtures thereof, when R.sub.1 and R.sub.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: November 29, 1988
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
  • Patent number: 4786317
    Abstract: Compounds of the formula ##STR1## wherein W and X, which may be identical to or different from each other, are each hydrogen, fluorine, chlorine, bromine, iodine, nitro, alkyl of 1 to 4 carbon atoms, fluoro-substituted alkyl of 1 to 4 carbon atoms or chloro-substituted alkyl of 1 to 4 carbon atoms;Y is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, fluoro-substituted alkyl of 1 to 4 carbon atoms or chloro-substituted alkyl of 1 to 4 carbon atoms;Z is fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, fluoro-substituted alkyl of 1 to 4 carbon atoms, chloro-substituted alkyl of 1 to 4 carbon atoms, --COOH or --COO-(alkyl of 1 to 4 carbon atoms); andn is 0 or 1;and, when Z is COOH, salts thereof, especially their alkali metal salts. The compunds as well as the salts are useful as selective herbicides.
    Type: Grant
    Filed: September 5, 1986
    Date of Patent: November 22, 1988
    Assignee: Celamerck GmbH & Co. KG
    Inventors: Rudolf Mengel, Ludwig Schroder, Werner Stransky, Gerbert Linden, Sigmund Lust
  • Patent number: 4786646
    Abstract: The invention relates to compounds of the formula ##STR1## Y is O or S, *A is paraphenylene or *--(CH.sub.2).sub.n --(X).sub.m --(CH.sub.2).sub.r --, X is O, S or --CH.dbd.CH--, n or r, independently, are integers from 0 to 3, s is an integer from 0 to 1, m is an integer from 0 to 1, provided that when m is 1, n+s must be at least 2, R.sub.1 and R.sub.2, independently, are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, Het or aryl, *E is ##STR2## or --(CH.sub.2).sub.k -- wherein k is an integer from 0 to 4, R.sub.3, R.sub.4 and R.sub.8 are independently hydrogen or lower alkyl, R.sub.5 and R.sub.6, independently are hydrogen or lower alkyl, R.sub.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: November 22, 1988
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
  • Patent number: 4778895
    Abstract: The invention relates to enantiomers of 1-(6-phenoxy-2-pyridyl)ethanols of the formula ##STR1## wherein * is (+) or (-) and X and Y are each independently of the other hydrogen, halogen, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.2 -C.sub.5 alkynyl.The invention also relates to the preparation of these enantiomers and to their use for the preparation of biocidal compounds.
    Type: Grant
    Filed: April 6, 1987
    Date of Patent: October 18, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Eric Francotte, Peter Ackermann
  • Patent number: 4776880
    Abstract: Disclosed are diphenoxymethylpyridines, their preparation and their use as herbicides.
    Type: Grant
    Filed: February 1, 1988
    Date of Patent: October 11, 1988
    Assignee: The Dow Chemical Company
    Inventors: Sudarshan K. Malhotra, Ingrid L. Knox
  • Patent number: 4772633
    Abstract: This invention relates to a novel compound represented by the following general formula (I), its production, and an insecticidal and acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, are a hydrogen atom, a halogen atom, a lower alkyl group, a trifluoromethyl group, a lower alkoxyl group, a lower alkenyloxy group or a halogenated lower alkoxyl group or are, taken together, a methylenedioxy group; R.sub.3 is a vinyl group or a ethynyl group; R.sub.4 is a hydrogen atom or a lower alkyl group; R.sub.5 is a hydrogen atom or a fluorine atom; R.sub.6 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxyl group or a trifluoromethyl group; Z is a nitrogen atom or a group represented by the formula --CH.dbd.; when Z is a nitrogen atom, Y is an oxygen atom; and when Z is a group of the formula --CH.dbd., Y is an oxygen atom, a sulfur atom, a methylene group or a group represented by the formula --NH--.
    Type: Grant
    Filed: February 20, 1986
    Date of Patent: September 20, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritada Matsuo, Kazunori Tsushima, Sumio Nishida, Toshihiko Yano, Masachika Hirano
  • Patent number: 4771059
    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## X.sup.-, wherein X.sup.- is the anion of a non-toxic pharmaceutically acceptable acid, are also disclosed.
    Type: Grant
    Filed: August 29, 1985
    Date of Patent: September 13, 1988
    Assignee: University of Florida
    Inventor: Nicholas S. Bodor
  • Patent number: 4765825
    Abstract: The invention relates to new aryloxy phenoxy acyl malonates of the general Formula I ##STR1## a process for the preparation thereof and herbicidal compositions comprising the same.In the general Formula IR.sup.1 stands for hydrogen, halogen, trifluoromethyl, trifluoromethoxy or cyano;R.sup.2 represents hydrogen, halogen or methyl;R.sup.3 is C.sub.1-4 alkyl; and the R.sup.3 substituents may be the same or different,X stands for --N.dbd. or --CH.dbd. andn is 0 or 1.The compounds of the general Formula I may be prepared by reacting a compound of the general Formula II ##STR2## with a metal derivative of a malonate of the general Formula III ##STR3## or in the presence of a metal compound with a malonate of the general Formula III; or reacting a compound of the general Formula IV ##STR4## with a compound of the general Formula V; ##STR5## or reacting a compound of the general Formula VI ##STR6## with a compound of the general Formula VII ##STR7## (in which Formulae R.sup.1, R.sup.2, R.sup.
    Type: Grant
    Filed: September 23, 1986
    Date of Patent: August 23, 1988
    Assignees: Budapesti Vegyimuvek, MTA Kozponti Kemiai Kutato Intezet
    Inventors: Tamas Komives, Ferenc Dutka, Istvan Barta, Istvan Jablonkai, Agnes Hulesch, Ferenc Bihari, Gyula Eifert, Peter Bohus, Katalin Tromfos, Agnes Meszaros nee Szekrenyesi, Istvan Kuronya
  • Patent number: 4766220
    Abstract: The invention relates to the preparation of optically active aryloxyalkanoic acid derivatives of the formula ##STR1## in which Ar represents an optionally substituted phenyl, naphthyl, phenoxy or pyridyloxy radical, R represents a C.sub.1 -C.sub.4 -alkyl radical and A represents a --COOR.sub.1, ##STR2## or --CO--Z radical, Z being halogen. It consists in reacting an aqueous or aqueous-organic solution of an optically active alkali metal salt of a 2-halogeno-alkanoic acid with an aqueous solution of an alkali metal salt of the phenol of the formula Ar-OH at an elevated temperature under a pressure less than the vapor pressure of water at the chosen temperature.It permits the preparation of aryloxyalkanoic acid derivatives with a very high content of the isomer having the D configuration, which can be used as herbicides.
    Type: Grant
    Filed: July 30, 1985
    Date of Patent: August 23, 1988
    Assignee: Rhone-Poulenc Agrochimie
    Inventor: Georges Gras
  • Patent number: 4759796
    Abstract: 2-Phenoxypropionic acid cyanamides of the formula ##STR1## have a useful selective herbicidal activity against weeds, preferably grass weeds, in crops of useful plants.In this formulaR is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl or C.sub.2 -C.sub.4 alkoxyalkyl, andT is a radical ##STR2## wherein A is oxygen or sulfur,X is fluorine, chlorine, bromine, iodine or trifluoromethyl,Y is hydrogen, fluorine, chlorine, bromine or trifluoromethyl, andZ is nitrogen or the methine bridge.
    Type: Grant
    Filed: October 16, 1986
    Date of Patent: July 26, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Beat Bohner, Hermann Rempfler, Rolf Schurter
  • Patent number: 4756739
    Abstract: The compounds of the formula I ##STR1## in which A denotes N or N.fwdarw.O, Z denotes O or NH, R denotes H, (halo)alkyl, (halo)alkenyl, (halo)alkynyl or alkoxycarbonyl, R.sup.1 denotes hydrogen, halogen, amino, --NHOH, hydroxyl, (substituted) phenylazo or a radical of the formulae Y=C=N--, Y.sup.1 Y.sup.2 C.dbd.N--, Y.sup.3 NH-- or ##STR2## K denotes 0 or 1, and m and n, independently of one another, denote a number from 1 to 4, with the proviso that, when Z-R denotes OH or NH.sub.2, (R.sup.1).sub.n denotes at least one radical of the formula ##STR3## or represents two radicals, in the 5 or 6 position of the heterocyclic ring, which, in the 5 position, denote halogen and, in the 6 position, denote a radical of the group comprising halogen, amino, hydroxyl or phenylazo, which may be substituted as specified above, are valuable intermediates in the synthesis of plant protection agents.
    Type: Grant
    Filed: December 19, 1986
    Date of Patent: July 12, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Fuss, Volker Koch
  • Patent number: 4757081
    Abstract: New substituted derivatives of 1,2,6-triphenyl-4(1H)-pyridinone are now provided, which are useful as fungicidal agent having practically valuable and improved fungicidal activities against a variety of phyto-pathogenic microorganisms, especially fungi and which show low toxicity to animals, including humans. These new compounds may be produced by different processes.
    Type: Grant
    Filed: March 26, 1987
    Date of Patent: July 12, 1988
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Norihisa Yonekura, Takashi Yumita, Yukio Nezu, Yoshiyuki Kojima, Shin-ichiro Maeno, Shigeharu Yaguchi
  • Patent number: 4753673
    Abstract: Compounds according to the following formula are useful as herbicidal agents: ##STR1## wherein the various substituents are defined hereinbelow.
    Type: Grant
    Filed: June 23, 1978
    Date of Patent: June 28, 1988
    Assignee: The Dow Chemical Company
    Inventors: Howard Johnston, Lillian H. Troxell
  • Patent number: 4751225
    Abstract: A nitrogen-containing heterocyclic compound of the formula: ##STR1## wherein R.sub.1 is either one of the following groups: ##STR2## (in which R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15, R.sub.16 and R.sub.17 are, 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 alkoxy group, a C.sub.1 -C.sub.4 alkylthio group, a trifluoromethyl group or a nitro group, R.sub.18, R.sub.19, R.sub.20 and R.sub.21 are, the same or different, each a hydrogen atom or a methyl group, k is an integer of 0 to 1 and l is an integer of 0 to 3);R.sub.2 and R.sub.3 are, the same or different, each a hydrogen atom, a halogen atom or a methyl group;R.sub.4 is a halogen atom or a methyl group;R.sub.5 and R.sub.6 are, 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 alkoxy group, a C.sub.1 -C.sub.4 haloalkyl group or a C.sub.1 -C.sub.
    Type: Grant
    Filed: April 21, 1987
    Date of Patent: June 14, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Sumio Nishida, Noritada Matsuo, Makoto Hatakoshi, Hirosi Kisida
  • Patent number: 4750931
    Abstract: Certain novel fluorophenoxy compounds, principally aryloxyfluorophenoxyalkanoic acids and derivatives thereof, are described. More specifically, these novel compounds bear 1 to 4 fluorine substituents on the phenyl ring. These novel compounds exhibit surprising preemergent and postemergent activity when used according to the method of the invention in the control of grassy weeds.
    Type: Grant
    Filed: October 15, 1985
    Date of Patent: June 14, 1988
    Assignee: The Dow Chemical Company
    Inventor: Richard B. Rogers
  • Patent number: 4743622
    Abstract: The invention relates to new aromatic alkane derivatives of the general formula ##STR1## in which R.sub.1 is aryl or aryl substituted by C.sub.1-4 alkyl, halo-C.sub.1-4 alkyl, phenyl-C.sub.1-4 alkyl, C.sub.2-4 alkenyl, halo-C.sub.2-4 alkenyl, phenyl-C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, halo-C.sub.2-4 alkynyl, phenyl-C.sub.2-4 alkynyl, C.sub.1-4 alkoxy, halo-C.sub.1-4 alkoxy, phenyl-C.sub.1-4 alkoxy, C.sub.2-4 alkenyloxy, halo-C.sub.2-4 alkenyloxy, phenyl-C.sub.2-4 alkenyloxy, C.sub.2-4 alkynyloxy, halo-C.sub.2-4 alkynyloxy, phenyl-C.sub.2-4 alkynyloxy, alkylsulphonyloxy, haloalkylsulphonyloxy, arylsulphonyloxy, halo, cyano, nitro, aryloxy, haloaryloxy, C.sub.1-4 alkyl-aryloxy, or nitroaryloxy,R.sub.2 is hydrogen or C.sub.1-4 alkyl,R.sub.3 is hydrogen, cyano or ethynyl,R.sub.4 is phenyl or pyridyl or these groups substituted by one or more of C.sub.1-6 alkyl, halo-C.sub.1-6 alkyl, phenyl-C.sub.1-6 alkyl, C.sub.1-6 alkyl interrupted by an O-, N- or S- atom, C.sub.2-4 alkenyl, halo-C.sub.2-4 alkenyl, phenyl-C.
    Type: Grant
    Filed: February 11, 1986
    Date of Patent: May 10, 1988
    Assignee: Schering Aktiengesellschaft
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien
  • Patent number: 4740235
    Abstract: There are described novel 3-fluoropyridyl-2-oxy derivatives having a herbicidal action and an action reducing the growth of grasses, which compounds correspond to the formula I ##STR1## wherein X is halogen or the trifluoromethyl group, andZ is an alkanoic acid derivative which is more precisely described in the specification.These compounds are suitable for the selective control of weeds in crops of cultivated plants, or for the reduction of the growth of grasses.
    Type: Grant
    Filed: March 26, 1986
    Date of Patent: April 26, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Schurter, Peter J. Diel
  • Patent number: 4731108
    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: March 7, 1986
    Date of Patent: March 15, 1988
    Assignee: The Dow Chemical Company
    Inventors: James A. Turner, Wendy S. Jacks, Paul S. Zorner
  • Patent number: 4731107
    Abstract: Disclosed are diphenoxymethyl pyridines, their preparation and their use as herbicides.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: March 15, 1988
    Assignee: The Dow Chemical Company
    Inventors: Sudarshan K. Malhotra, Ingrid L. Evoy
  • Patent number: 4723013
    Abstract: Certain 4,8-disubstituted-2,6-naphthalene dicarboxylic acid monomers and a method for their preparation. These monomers are useful for the preparation of polymers, which polymers may be used to prepare high strength fibers.
    Type: Grant
    Filed: April 7, 1987
    Date of Patent: February 2, 1988
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Tsu-Tzu Tsai, Fred E. Arnold
  • Patent number: 4717417
    Abstract: New dextrorotatory enantiomers of phenoxy propionic acid derivatives of the formula ##STR1## in which R.sup.1 represents a radical of the formula ##STR2## wherein X.sup.1 represents hydrogen or halogen,X.sup.2 represents halogen or trifluoromethyl,X.sup.3 represents halogen or trifluoromethyl,X.sup.4 represents hydrogen or halogen andX.sup.5 represents hydrogen or halogen,Y represents oxygen or the radical SO.sub.m,whereinm represents 0, 1 or 2,R.sup.2 represents hydrogen or methyl,n represents 1 or 2 andR.sup.3 and R.sup.4 independently of one another represent hydrogen, halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, nitro, cyano or alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy group, and their use as herbicides.
    Type: Grant
    Filed: March 14, 1986
    Date of Patent: January 5, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Koichi Moriya, Uwe Priesnitz, Hans-Jochem Riebel, Ludwig Eue, Robert R. Schmidt
  • Patent number: 4717726
    Abstract: 3,5-Dichloro-2,4-dimethoxy-6-(trichloromethyl)-pyridine, which can be prepared from 2,3,4,5-tetrachloro-6-(trichloromethyl)pyridine and an alkali metal methoxide, is an anticancer agent especially useful for the treatment of leukemias, lymphomas, mammary carcinomas, and ovarian sarcomas.
    Type: Grant
    Filed: September 10, 1986
    Date of Patent: January 5, 1988
    Assignee: The Dow Chemical Company
    Inventor: Helen K. Tobol
  • Patent number: 4714706
    Abstract: Nitrogen-containing heterocyclic compounds are represented by the formula: ##STR1## wherein R.sub.1 is either one of the following groups: ##STR2## (in which R.sub.4 is a hydrogen atom, a halogen atom or a methyl group and l is an integer of 1 or 2);R.sub.2 is a hydrogen atom or a methyl group;R.sub.3 is an alkyl group, an alkoxy group, an alkenyl group or an alkenyloxy group, all of which may have optionally one or more substituents;A is either one of the following groups: ##STR3## (in which R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are, the same or different, each a hydrogen atom or a methyl group,R.sub.10 is a hydrogen atom, a halogen atom or a lower alkyl group and m is an integer of 1 to 4); andX is an oxygen atom or a sulfur atom,which is useful as an insecticidal agent.
    Type: Grant
    Filed: May 30, 1986
    Date of Patent: December 22, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hirosi Kisida, Sumio Nishida, Makoto Hatakoshi
  • Patent number: 4713109
    Abstract: There is described the 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)-phenoxy]-propionic acid propynyl ester and its (R)-enantiomer of formula I ##STR1## These compounds are suitable for selectively controlling weeds in crops of cultivated plants, or for reducing the growth of grasses.
    Type: Grant
    Filed: May 2, 1986
    Date of Patent: December 15, 1987
    Assignee: Ciba Geigy Corporation
    Inventors: Rolf Schurter, Hermann Rempfler
  • Patent number: 4708733
    Abstract: The invention relates to new 4-chloro-aryloxy-acetyl- or 4-chloro-aryloxy-propionyl-malonates of the general Formula I, ##STR1## a process for the preparation thereof and herbicidal compositions comprising the same.In the general Formula IR.sup.1 stands for chlorine or methyl;R.sup.2 represents hydrogen or chlorine;R.sup.3 stands for hydrogen or methyl;R.sup.4 represents C.sub.1-4 alkyl and the two R.sup.4 groups may be identical or different; andX is --N.dbd. or --CH.dbd..The compounds of the general Formula I may be prepared by reacting a compound of the general Formula II ##STR2## with a metal derivative of a malonate of the general Formula III; ##STR3## or in the presence of an metal compound with a malonate of the general Formula III; or by reacting a compound of the general Formula IV ##STR4## with a compound of the general Formula V ##STR5## (in which Formulae R.sup.1, R.sup.2, R.sup.3, R.sup.4 and X are as stated above; Z stands for halogen and Y represents halogen, cyano or alkylcarbonyloxy).
    Type: Grant
    Filed: September 23, 1986
    Date of Patent: November 24, 1987
    Assignees: Budapesti Vegyimuvek, MTA Kozponti Kemiai I Kutato Intezet
    Inventors: Tamas Komives, Ferenc Dutka, Istvan Barta, Istvan Jablonkai, Agnes Hulesch, Ferenc Bihari, Gyula Eifert, Peter Bohus, Mihaly Nagy, Gyorgy Bacskai, Istvan Kuronya
  • Patent number: 4709077
    Abstract: Novel 7-(Aryloxy)-2-naphthoxyalkanecarboxylic acid derivatives of the formula I ##STR1## in racemic or separated isomeric form, have herbicidal activity.
    Type: Grant
    Filed: September 17, 1985
    Date of Patent: November 24, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Michael Harre, Hans-Rudolf Kruger, Friedrich Arndt, Reinhart Rusch
  • Patent number: 4701531
    Abstract: A process for preparing O-alkylated halopyridinate compounds is described. The process does not require the use of added organic solvents.
    Type: Grant
    Filed: December 1, 1986
    Date of Patent: October 20, 1987
    Assignee: The Dow Chemical Company
    Inventor: Timothy J. Adaway
  • Patent number: 4701464
    Abstract: Insecticidal compounds of the formula ##STR1## formulations thereof, their use for control of foliar or soil-borne insects, their method of preparation and certain novel intermediates for their preparation are disclosed and exemplified.
    Type: Grant
    Filed: June 3, 1985
    Date of Patent: October 20, 1987
    Assignee: FMC Corporation
    Inventors: Richard B. Phillips, Ernest L. Plummer, John F. Engel
  • Patent number: 4694013
    Abstract: Insecticidal and acaricidal organic esters formed from pyrethroid carboxylic acids and phenoxypyridinyltrifluoroethanols, agricultural compositions containing said esters and their use against anthropod pests including soil-dwelling species; also, intermediates for these insecticides and acaricides and a process for the preparation of said intermediates.
    Type: Grant
    Filed: September 26, 1986
    Date of Patent: September 15, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: George P. Lahm
  • Patent number: 4692183
    Abstract: Disclosed are diphenoxymethyl pyridines, their preparation and their use as herbicides.
    Type: Grant
    Filed: December 30, 1985
    Date of Patent: September 8, 1987
    Assignee: The Dow Chemical Company
    Inventors: Sudarshan K. Malhotra, Ingrid L. Evoy
  • Patent number: 4691020
    Abstract: Optically active carboxylic acids ##STR1## where R.sup.1 is an organic radical which is linked to the asymmetric C' atom via a carbon atom and R.sup.2 is one of the radicals R.sup.1 (but not the same radical), halogen or an organic radical which is bonded to the asymmetric C' atom via an oxygen atom, are prepared by reacting a ketene II ##STR2## with an alcohol in a homogeneous liquid phase in the presence of a tertiary amine III and then converting the resulting ester into the acid, using an optically active alcohol IV.
    Type: Grant
    Filed: July 23, 1984
    Date of Patent: September 1, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Christoph Ruechardt, Joachim Jaehme, Ulrich Salz
  • Patent number: 4689342
    Abstract: Novel esters in all possible isomeric forms or a mixture thereof having the formula ##STR1## wherein Y is selected from the group consisting of hydrogen, halogen, --OAlK and ##STR2## AlK is alkyl of 1 to 6 carbon atoms, n is 0, 1 or 2, Z is selected from the group consisting of --O-- and --S--, R.sub.1 is selected from the group consisting of (a) optionally unsaturated alkyl of 1 to 8 carbon atoms and optionally unsaturated cycloalkyl or cycloalkylalkyl of 3 to 8 carbon atoms optionally substituted with at least one member of the group consisting of halogen, --OH, --SH, --OR', --SR', ##STR3## --SO.sub.2 AlK.sub.2, --SO.sub.3 AlK.sub.3, aryl optionally substtuted with at least one member of the group consisting of --OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, --CF.sub.3, --OCF.sub.3, --SCF.sub.3 and ##STR4## R' is alkyl of 1 to 8 carbon atoms, R" and R'" are individually selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, AlK.sub.1, AlK.sub.2 and AlK.
    Type: Grant
    Filed: November 21, 1983
    Date of Patent: August 25, 1987
    Assignee: Roussel Uclaf
    Inventors: Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4685959
    Abstract: Novel pyridyloxyphenoxyalkanoates, alkenoates, R-enantiomers and derivatives thereof possess herbicidal activity selectively in the presence of broadleaf crops with preemergent or postemergent applications.
    Type: Grant
    Filed: December 17, 1985
    Date of Patent: August 11, 1987
    Assignee: The Dow Chemical Company
    Inventors: Richard B. Rogers, Cleve A. I. Goring
  • Patent number: 4685953
    Abstract: Disclosed are diphenoxymethylpyridines, their preparation and their use as herbicides.
    Type: Grant
    Filed: December 30, 1985
    Date of Patent: August 11, 1987
    Assignee: The Dow Chemical Company
    Inventors: Sudarshan K. Malhotra, Ingrid L. Evoy
  • Patent number: 4684477
    Abstract: A novel pyridine derivative which, when added to liquid crystal substances, can improve various specific features required for the resulting liquid crystal compositions, and a liquid crystal composition containing the same are provided, which pyridine derivative is expressed by the formula ##STR1## wherein W represents H or F; X, F, Cl or alkyl or alkoxy of 1.about.10 C; ##STR2## n, 0 or 1; Y, CN or alkyl or alkoxy of 1.about.10 C; Z, F, Cl or H; and when Z is F or Cl, Y is limited to CN, excluding certain identified compounds.
    Type: Grant
    Filed: February 27, 1986
    Date of Patent: August 4, 1987
    Assignee: Chisso Corporation
    Inventors: Shigeru Sugimori, Kazunori Nigorikawa, Tetsuya Ogawa
  • Patent number: 4684394
    Abstract: Novel aryloxyphenoxyalkanoates, alkenoates, R-enantiomers and derivatives thereof possess herbicidal activity selectively in the presence of broadleaf crops with preemergent or postemergent applications.
    Type: Grant
    Filed: October 29, 1985
    Date of Patent: August 4, 1987
    Assignee: The Dow Chemical Company
    Inventors: Richard B. Rogers, Cleve A. I. Goring
  • Patent number: 4681941
    Abstract: An improved method of preparing aryloxyphenoxy propanoic acid esters is disclosed. Low-water levels and low temperatures increase the yield and decrease by-product formation. A hindered non-nucleophilic phenol, which is converted in situ to the phenate form, is added to the reaction mixture to drive the reaction to 99+% conversion.
    Type: Grant
    Filed: April 11, 1985
    Date of Patent: July 21, 1987
    Assignee: The Dow Chemical Company
    Inventor: Timothy J. Adaway