1,3-diazines (including Hydrogenated) Patents (Class 504/239)
  • Patent number: 6140270
    Abstract: An improved process for the preparation of 6-(perfluoroalkyl)uracil compounds having the structural formula I ##STR1## from 2-(N,N-disubstituted)amino-4-(perfluoroalkyl)-1,3-oxazin-6-one compounds having the structural formula II ##STR2##
    Type: Grant
    Filed: February 16, 1999
    Date of Patent: October 31, 2000
    Assignee: American Cyanamid Company
    Inventors: Richard Anthony Rampulla, Venkataraman Kameswaran, Peter John Wepplo
  • Patent number: 6048824
    Abstract: Compounds of formula (I), wherein A is an unsubstituted or substituted aromatic or non-aromatic, monocyclic or bicyclic heterocyclic radical wherein a ring nitrogen atom may have been replaced by a group ##STR2## R.sub.1 is hydrogen or C.sub.1 -C.sub.3 alkyl; R.sub.2 is hydrogen or C.sub.1 -C.sub.3 alkyl; R.sub.3 is hydrogen, an unsubstituted or substituted C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 alkynyl group, or C(.dbd.O)--R.sub.5, R.sub.5 is C.sub.1 -C.sub.4 alkyl C.sub.1 -C.sub.4 alkoxy, an unsubstituted or substituted phenyl, phenoxy or benzyloxy group, or N(R.sub.6).sub.2, each R.sub.6, independently of the other, is hydrogen, C.sub.1 -C.sub.4 alkyl or unsubstituted or substituted phenyl, X is CH--NO.sub.2, N--CN or N--NO.sub.2 and n is from 1 to 3, in free form or in salt form, and, where appropriate, tautomers of those compounds and the salts thereof, can be used as agrochemical active ingredients and can be prepared in a manner known per se.
    Type: Grant
    Filed: November 22, 1995
    Date of Patent: April 11, 2000
    Assignee: Novartis Corporation
    Inventors: Peter Maienfisch, Jozef Gonda, Olivier Jacob, Laurenz Gsell
  • Patent number: 6004903
    Abstract: Benzoyl derivatives of the formula I ##STR1## where Z is a 5-membered or 6-membered heterocyclic, saturated or unsaturated radical containing one to three hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen,Q is a cyclohexane-1, 3-dione ring bonded in the 2-position and of the formula II, ##STR2## or conventional agricultural salts of the compounds I.
    Type: Grant
    Filed: August 14, 1997
    Date of Patent: December 21, 1999
    Assignee: Basf Aktiengesellschaft
    Inventors: Wolfgang von Deyn, Regina Luise Hill, Uwe Kardorff, Stefan Engel, Martina Otten, Marcus Vossen, Peter Plath, Harald Rang, Albrecht Harreus, Franz Rohl, Helmut Walter, Karl-Otto Westphalen, Ulf Misslitz
  • Patent number: 5935907
    Abstract: The invention is related to a novel phenylacetylene derivates of formula: ##STR1## wherein X represents hydrogen, halogen, optionally substituted C.sub.1-6 alkyl; Y represents hydrogen, halogen, cyano, nitro, optionally substituted C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.3-8 cycloalkoxy, optionally substituted C.sub.1-6 alkylthio, C.sub.3-8 cycloalkylthio, C.sub.1-6 alkylsulfinyl, optionally substituted C.sub.1-6 alkylsulfonyl, C.sub.3-8 cycloalkylsulfonyl, C.sub.1-6 alkylsulfonyloxy, optionally substituted sulfonamide, optionally substituted carboxamide, etc., or Y may form together with Z which is bonded to the vicinal carbon atom a 5- or 6-membered ring; n is 0 or 1; Z represents hydrogen or halogen; m is 1 or 2; R represents hydrogen, halogen, C.sub.1-6 alkyl, tri(C.sub.1-6 alkyl)silyl, COOR.sup.c or CONR.sup.d R.sup.e ; Q represents a heterocyclic group, and their use as herbicid.
    Type: Grant
    Filed: March 24, 1998
    Date of Patent: August 10, 1999
    Assignee: Nihon Bayer Agrochem K.K.
    Inventors: Akihiko Yanagi, Shin-ichi Narabu, Toshio Goto, Seishi Ito, Natsuko Minegishi, Tatsuya Yamaoka, Chieko Ueno
  • Patent number: 5925596
    Abstract: Substituted aminomethylphenylsulfonylureas, their preparation, and their use as herbicides and plant growth regulatorsCompounds of the formula (I) and salts thereof ##STR1## where R.sup.1 to R.sup.7 and A are as defined in claim 1 and, inter alia, F.sup.5 is an acyl radical or NR.sup.4 R.sup.5 together are a heterocyclic radical, are useful as herbicides and plant growth regulators. They can be prepared by the methods of known processes, using novel intermediates of the formula (II), (IV), (VI) or (VII) (cf. claim 5).
    Type: Grant
    Filed: April 24, 1997
    Date of Patent: July 20, 1999
    Assignee: Hoechst-Schering AgrEvo GmbH
    Inventors: Klaus Lorenz, Lothar Willms, Klaus Bauer, Hermann Bieringer, Christopher Rosinger
  • Patent number: 5877120
    Abstract: A nicotinic acid derivative represented by general formula (I) or (II), a salt thereof, and a herbicide containing the same as the active ingredient, wherein A represents substituted phenyl, or 5- or 6- membered heterocycle, e.g., thienyl or pyridyl; R represents hydroxy, optionally substituted alkoxy or optionally substituted benzyloxy; R.sup.1 and R.sup.2 represent each independently alkoxy or halogen; R.sup.3 and R.sup.4 represent each independently hydrogen, hydroxy, cyano or alkoxycarbonyl, or they may be combined together to represent oxygen; X represents halogen, alkyl or alkoxy; n represents 0, 1 or 2; and Z represents methine or nitrogen. The compound and salts thereof can control annual or perennial weed growing on the land where various crops such as rice plant, wheat, cotton and corn grow for a wide period ranging from the pre-emergence to growth in a remarkably small dose.
    Type: Grant
    Filed: September 18, 1996
    Date of Patent: March 2, 1999
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masahiro Miyazaki, Sumio Yokota, Yoshihiro Ito, Nobuyuki Ohba, Nobuhide Wada, Shigehiko Tachikawa, Takeshige Miyazawa
  • Patent number: 5856273
    Abstract: A compound of formula (I): ##STR1## where E is oxygen or sulphur; A is CR.sup.3 or N where R.sup.3 is hydrogen or hydrocarbyl; D completes a 5 or 6-membered non-aromatic heterocyclic ring which optionally contains additional heteroatoms selected from oxygen, nitrogen or sulphur and which is optionally substituted by an optionally substituted lower hydrocarbyl group, or an optionally substituted heteroaryl group; R.sup.1 and R.sup.2 are each independently hydrogen; optionally substituted lower hydrocarbyl, or optionally substituted heteroaryl, or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached, form a heterocyclic ring; Z represents halogen optionally substituted lower hydrocarbyl, optionally substituted lower hydocarbyloxy, optionally substituted lower hydrocarbylthio, hydrocarbylsulphinyl or hydrocarbylsulphonyl, cyano, nitro, CHO, NHOH, ONR.sup.7' R.sup.7", SF.sub.5 ; CO (optionally substituted lower hydrocarbyl), acylamino, COOR.sup.7, SO.sub.2 NR.sup.8 R.sup.9, CONR.sup.
    Type: Grant
    Filed: October 6, 1995
    Date of Patent: January 5, 1999
    Assignee: Zeneca Limited
    Inventors: Ian Trevor Kay, John Edward Duncan Barton, David John Collins, Bogdan Kowalczyk, Glynn Mitchell, John Martin Shribbs, John Micheal Cox, Nigel John Barnes, Stephen Christopher Smith
  • Patent number: 5776858
    Abstract: 1-Azinyl-tetraozolinones of the following formulae (I) and (II): ##STR1## wherein R.sup.1 and R.sup.2 are independently represent alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl or optionally substituted phenyl, orR.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, may form a 5- or 6-membered heterocyclic ring which may optionally contain a further heteroatom, and said heterocyclic ring may optionally be benzo-condensed and/or be substituted by one or more of C.sub.1-4 alkyl(s), andR.sup.3 is a 6-membered heterocyclic aromatic group consisting of carbon atoms and 2 or 3 nitrogen atoms, which may optionally be substituted by halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, di(C.sub.1-4 alkyl)amino or phenyl.The compounds of the formula (I) exhibit an excellent herbicidal activity and the compounds of the formula (II) are useful as starting materials in the production of the compounds of the formula (I).
    Type: Grant
    Filed: October 25, 1996
    Date of Patent: July 7, 1998
    Assignee: Nihon Bayer Agrochem K.K.
    Inventors: Toshio Goto, Seishi Ito, Natsuko Minegishi, Tatsuya Yamaoka, Chieko Ueno, Koichi Moriya, Fritz Maurer, Ryo Watanabe
  • Patent number: 5777162
    Abstract: Described herein are compounds of Formula (XX) and Formula (XXIV), shown below, and processes of making same. ##STR1## wherein p is 0 ##STR2## wherein p is 1, and Y is chlorine or bromine.
    Type: Grant
    Filed: November 12, 1996
    Date of Patent: July 7, 1998
    Assignee: Zeneca Limited
    Inventors: Ian Richard Matthews, Christopher Richard Ayles Godfrey, John Martin Clough
  • Patent number: 5773388
    Abstract: Novel pyrimidine derivatives of the formula (I): ##STR1## wherein R1 is a C.sub.1 -C.sub.6 haloalkyl group, a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group or the like, R2 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group or the like, and X is a carbonyl group or --C(R3)OH (wherein R3 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group or the like).
    Type: Grant
    Filed: February 9, 1996
    Date of Patent: June 30, 1998
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Jun Satow, Yasuo Kondo, Yoshihiro Kudo, Takumi Mikashima, Tsutomu Nawamaki, Yoichi Ito, Kazuhisa Sudo, Kunimitsu Nakahira, Shigeomi Watanabe, Kimihiro Ishikawa
  • Patent number: 5763357
    Abstract: Herbicidal 3-substituted pyridine compounds and derivatives thereof of the formula: ##STR1## wherein Ar is a substituted or unsubstituted 5- or 6-membered heteroaryl group having 1, 2 or 3 ring nitrogen atoms with the remainder of the ring atoms being carbon; a substituted or unsubstituted 5-membered heteroaryl group having a ring heteroatom of oxygen or sulfur with the remainder of the ring atoms being carbon; or a substituted or unsubstituted 5-membered heteroaryl group having one ring nitrogen atom and either an oxygen or sulfur ring heteroatom with the remainder of the ring atoms being carbon. Herbicidal compositions containing such 3-substituted pyridine compounds and derivatives thereof and methods of controlling undesirable vegetation employing these compounds and derivatives are also disclosed. The compounds in which XR is hydroxyl are also useful as intermediates for producing the disclosed 3-substituted pyridine derivatives.
    Type: Grant
    Filed: November 1, 1996
    Date of Patent: June 9, 1998
    Assignee: Zeneca Limited
    Inventors: Hsiao-Ling M. Chin, Nhan H. Nguyen, David B. Kanne, David L. Lee
  • Patent number: 5753594
    Abstract: 3-Halo-3-hetarylcarboxylic acid derivatives having the formula I ##STR1## in which R is a formyl group, a group CO.sub.2 H or a radical which can be hydrolyzed to COOH, and the remaining substituents have the following meanings:R.sup.2 and R.sup.3 are halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio;X is nitrogen or CR.sup.13, where R.sup.13 is hydrogen or together with R.sup.3 forms an alkylene or alkenylene chain in which in each case one methylene group is replaced by oxygen;R.sup.4 is an unsubstituted or substituted five- or six-membered heteroaromatic ring which contains one to three nitrogen atoms and/or one sulfur or oxygen atom;R.sup.5 is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl or phenyl;Y is sulfur, oxygen or a single bond; andZ is halogen.The derivatives I having herbicidal and plant-growth regulating properties.
    Type: Grant
    Filed: December 1, 1995
    Date of Patent: May 19, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Baumann, Albrecht Harreus, Matthias Bratz, Joachim Rheinheimer, Uwe Josef Vogelbacher, Hans Theobald, Matthias Gerber, Helmut Walter, Karl-Otto Westphalen, Wilhelm Rademacher
  • Patent number: 5747423
    Abstract: The novel 6-thienyl pyridines and 4-thienyl pyrimidines of formula I: ##STR1## (A, R.sub.1 to R.sub.5 and Z are defined in the specification) show selective herbicidal activity.The new compounds can be prepared according to known methods and can be used as herbicides in agriculture and related fields.
    Type: Grant
    Filed: July 15, 1996
    Date of Patent: May 5, 1998
    Assignee: American Cyanamid Company
    Inventors: Stefan Scheiblich, Thomas Maier, Helmut Siegfried Baltruschat, Joseph Luke Pont
  • Patent number: 5736487
    Abstract: Compounds of formula (I): ##STR1## (wherein: R.sup.1 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy, or optionally substituted alkylthio; R.sup.2 is hydrogen, optionally substituted alkyl, cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl or a group of formula --YR.sup.7 ; R.sup.3 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy group, optionally substituted alkenyl, optionally substituted alkynyl, halogen, nitro or a group of formula --COR.sup.8, wherein R.sup.8 is hydrogen, alkyl, cycloalkyl or alkoxy; R.sup.4 and R.sup.5 are each hydrogen atom or alkyl; R.sup.6 is optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy group, optionally substituted alkenyl, optionally substituted alkynyl, halogen, nitro, or a group of formula --COR.sup.8, as defined above;A, Q and X are each oxygen or sulfur; Y is a group of formula --CO--, --COO--, --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 CH.sub.2 O--, --CH.sub.2 CH.sub.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: April 7, 1998
    Assignee: Sankyo Company, Limited
    Inventors: Soji Sugai, Hiroyuki Komai, Noriaki Kudo, Kazuo Sato, Toyokuni Honma, Junji Kadotani, Kiyoshi Koi, Mitsuru Ito
  • Patent number: 5726127
    Abstract: The present invention relates to a thiophenesulfonylurea derivative represented by general formula (I), the process for preparation thereof, and herbicide using it; and a salt thereof, in which T represents a group T1, T2, or T3 having general formulae (a), wherein E represents a direct bond; R represents hydrogen or C.sub.1-4 acyl; R.sup.1 represents C.sub.1-6 alkyl substituted with 1 to 3 halogen atoms; R.sup.2 represents hydrogen, C.sub.1-3 alkyl, C.sub.1-3 haloalkyl, halogen, cyano, C.sub.1-3 alkoxy, C.sub.1-3 haloalkoxy, amino, methylamino, dimethylamino, or C.sub.1-3 alkyl substituted with C.sub.1-2 alkoxy, C.sub.1-2 haloalkoxy, thiol, methylthio, cyano or hydroxy; A represents a group selected from A1 to A4 having general formulae (b), and a herbicidal composition containing these derivatives.
    Type: Grant
    Filed: July 24, 1996
    Date of Patent: March 10, 1998
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Dae Whang Kim, Kyeong Yeol Yun, Jae Wook Ryu, Yeon Soo Lee, Seung Kyu Kang, In Taek Hwang
  • Patent number: 5716904
    Abstract: A novel 4,5-disubstituted pyrimidine derivative of the formula (I): ##STR1## wherein R1 is CF.sub.2 X (X is Cl or Br), R.sub.2 is a C.sub.1 -C.sub.8 alkyl group, a C.sub.3 -C.sub.8 cycloalkyl group, etc., R3 is a halogen atom, SH, NH.sub.2, etc., and R4 is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, etc., is a herbicide having excellent activities.
    Type: Grant
    Filed: May 1, 1996
    Date of Patent: February 10, 1998
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Jun Satow, Yasuo Kondo, Yoshihiro Kudo, Takumi Mikashima, Tsutomu Nawamaki, Yoichi Ito, Kazuhisa Sudo, Kunimitsu Nakahira, Shigeomi Watanabe, Kimihiro Ishikawa
  • Patent number: 5714438
    Abstract: Herbicidal 5-substituted pyrimidine compounds and derivatives thereof of the formula: ##STR1## Herbicidal compositions containing such 5-substituted pyrimidine compounds and derivatives thereof and methods of controlling undesirable vegetation using these compounds and derivatives are also disclosed. The compounds in which XR is hydroxyl are also useful as intermediates for producing the 5-substituted pyrimidine derivatives of the invention.
    Type: Grant
    Filed: December 5, 1996
    Date of Patent: February 3, 1998
    Assignee: Zeneca Limited
    Inventors: David B. Kanne, Michael P. Prisbylla
  • Patent number: 5707930
    Abstract: Herbicidal 4-cycloalkyl-5-substituted pyrimidine compounds of the formula ##STR1## are described. Herbicidal compositions containing such substituted-pyrimidinyl compounds and methods of controlling undesirable vegetation employing these compounds are also disclosed. The compounds in which XR, is hydroxyl are also useful as intermediates for producing the disclosed substituted-pyrimidinyl derivatives.
    Type: Grant
    Filed: September 16, 1996
    Date of Patent: January 13, 1998
    Assignee: Zeneca Limited
    Inventors: Raymond A. Felix, Hsiao-Ling M. Chin, Frank X. Woolard, David L. Lee, David B. Kanne
  • Patent number: 5703017
    Abstract: 3-(Het)arylcarboxylic acid derivatives of the formula I ##STR1## where R is formyl, CO.sub.2 H or a radical hydrolyzable to COOH and the other substituents have the following meanings:R.sup.2 and R.sup.3 are each halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio;X is nitrogen or CR.sup.14, where R.sup.14 is hydrogen or, together with R.sup.3, forms an alkylene or alkenylene chain, in each of which a methylene group is replaced by oxygen;R.sup.4 is phenyl or naphthyl, each of which is unsubstituted or substituted or an unsubstituted or substituted five-membered or six-membered heteroaromatic structure containing one to three nitrogen atoms or one sulfur or oxygen atom;R.sup.5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl or phenyl;R.sup.6 is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.
    Type: Grant
    Filed: October 19, 1995
    Date of Patent: December 30, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Baumann, Joachim Rheinheimer, Uwe Josef Vogelbacher, Matthias Bratz, Hans Theobald, Matthias Gerber, Karl-Otto Westphalen, Helmut Walter, Wilhelm Rademacher
  • Patent number: 5688745
    Abstract: The invention relates to novel herbicidal and plant growth-regulating compounds of the formula (I) or salts thereof, ##STR1## where Q, W, R, R, R, R, Y and Z are defined as in formula (I) as claimed in claim 1.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: November 18, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Oswald Ort, Klaus Bauer, Hermann Bieringer
  • Patent number: 5674811
    Abstract: A cyanoketone derivatives of the following formula (1) ##STR1## which are characterized by excellent herbicidal activity and effectiveness against a variety of broad leafed weeds, including barnyard grass, green foxtail, velvet leaf, livid amaranth and hairy beggar ticks.
    Type: Grant
    Filed: October 6, 1994
    Date of Patent: October 7, 1997
    Assignee: Tokuyama Corporation
    Inventors: Toshio Kitajima, Tadashi Kobutani, Shozo Kato, Masao Yamaguchi, Masahiko Ishizaki, deceased
  • Patent number: 5672567
    Abstract: Herbicidal substituted hydroxybenzyl-heteroaryl compounds and derivatives thereof of the formula ##STR1## wherein Ar is a substituted or unsubstituted 5- or 6-membered heteroaryl group having 2 or 3 ring nitrogen atoms or a substituted or unsubstituted 5-membered heteroaryl group having two ring heteroatoms, one of the ring heteroatoms being nitrogen and the other being sulfur or oxygen. Herbicidal compositions containing such substituted hydroxybenzyl-heteroaryl compounds and derivatives thereof and methods of controlling undesirable vegetation employing these compounds and derivatives are also disclosed. The compounds in which XR is hydroxyl are also useful as intermediates for producing the disclosed substituted hydroxybenzyl-heteroaryl derivatives.
    Type: Grant
    Filed: March 25, 1996
    Date of Patent: September 30, 1997
    Assignee: Zeneca Limited
    Inventors: Hsiao-Ling M. Chin, Yi-Qiu Wei, Nhan H. Nguyen, David B. Kanne
  • Patent number: 5665680
    Abstract: Provided is a method for increasing yield of soybean by foliar application of a gibberellin biosynthesis inhibiting type compound to soybean plants at the time of formation of pollen, at the time of formation of embryo sac or at the time of flowering.
    Type: Grant
    Filed: August 16, 1995
    Date of Patent: September 9, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kimio Nakaseko, Hideyuki Shibata, Seigo Ouchi, Akira Nishikawa
  • Patent number: 5661106
    Abstract: 3-(Het)aryloxy(thio)carboxylic acid derivatives of the formula I ##STR1## where R.sup.1 is hydrogen, COOH or a radical which can be hydrolyzed to give COOH;R.sup.2 and R.sup.3 are each halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio;X is nitrogen or CR.sup.14, where R.sup.14 is hydrogen or, together with R.sup.3, forms a 3-membered or 4-membered alkylene or alkenylene chain, in each of which a methylene group is replaced by oxygen;R.sup.4 is alkyl, cycloalkyl, cycloalkenyl, alkenyl or alkynyl, each of which is unsubstituted or substituted;an unsubstituted or substituted five-membered or six-membered heteroaromatic structure containing one to three nitrogen atoms or one sulfur or oxygen atom;unsubstituted or substituted phenyl or naphthyl;R.sup.4 and R.sup.5, together with the neighboring carbon atom, form a 3-membered to 8-membered ring which may contain an oxygen or sulfur atom and which is unsubstituted or substituted;R.sup.
    Type: Grant
    Filed: October 19, 1995
    Date of Patent: August 26, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Baumann, Joachim Rheinheimer, Uwe Josef Vogelbacher, Matthias Bratz, Norbert Meyer, Matthias Gerber, Karl-Otto Westphalen, Helmut Walter, Wilhelm Rademacher
  • Patent number: 5633256
    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: March 29, 1995
    Date of Patent: May 27, 1997
    Assignee: Zeneca Limited
    Inventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey
  • Patent number: 5629265
    Abstract: Disclosed herein are cyanoketone derivatives of the following formula (1) ##STR1## such as 1-cyano-1-piperidinocarbonyl-3-[4-(2-chloro-4-trifluoromethylphenoxy)pheno xy]-2-butanone, 1-cyano-1-piperidinocarbonyl-3-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy )phenoxy]-2-butanone, 1-cyano-1-(N-methyl-N-dichlorophenyl)aminocarbonyl-3-[4-(2-quinoxalyloxy)p henoxy]-2-butanone, 1-cyano-1-(N,N-dibutyl)aminocarbonyl-3-[4-(3-chloro-5-trifluoromethyl-2-py ridyloxy)phenoxy-2-butanone, and the like, which are characterized by excellent herbicidal activity and effectiveness against a variety of gramineous weeds.
    Type: Grant
    Filed: June 22, 1994
    Date of Patent: May 13, 1997
    Assignee: Tokuyama Corporation
    Inventors: Masahiko Ishizaki, Seiji Nagata, Junji Takenaka
  • Patent number: 5627138
    Abstract: Substituted phthalides and heterocyclic phthalides and derivatives thereof which are useful as herbicides are described.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: May 6, 1997
    Assignee: Sandoz Ltd.
    Inventors: Richard J. Anderson, Ian S. Cloudsdale, Takeo Hokama
  • Patent number: 5627137
    Abstract: Substituted phthalides and heterocyclic phthalides and derivatives thereof which are useful as herbicides are described.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: May 6, 1997
    Assignee: Sandoz Ltd.
    Inventors: Richard J. Anderson, Ian S. Cloudsdale, Takeo Hokama
  • Patent number: 5622917
    Abstract: The invention relates to new 1H-3-aryl-pyrrolidine-2,4-dione derivatives of the formula (I) ##STR1## in which A, B, X, Y and G have the meanings given in the description, to a plurality of processes for their preparation, and to their use as pesticides.
    Type: Grant
    Filed: January 3, 1995
    Date of Patent: April 22, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reiner Fischer, Thomas Bretschneider, Bernd-Wieland Kr uger, Michael Ruther, Christoph Erdelen, Ulrike Wachendorff-Neumann, Hans-Joachim Santel, Markus Dollinger
  • Patent number: 5616537
    Abstract: A condensed heterocyclic derivative of the formula (I): ##STR1## (wherein R is a hydroxyl group, R.sup.3 or R.sup.4 is an alkoxy group, W is an oxygen atom, Yn is a hydrogen atom, Z is a methine group, and A is a 5- or 6-membered heterocyclic ring which may be substituted, and a herbicide, are presented. When used for paddy field treatment, upland soil treatment and foliage treatment, the condensed heterocyclic derivative of the present invention exhibits excellent herbicidal activities against gramineous and non-gramineous weeds without adversely affecting crop plants.
    Type: Grant
    Filed: March 1, 1994
    Date of Patent: April 1, 1997
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Sumio Yokota, Masafumi Matsuzawa, Nobuyuki Ohba, Toshihiro Nagata, Shigehiko Tachikawa, Takeshige Miyazawa, Katsutada Yanagisawa
  • Patent number: 5610121
    Abstract: The invention relates to new heterocyclically disubstituted sulphonylamino(thio)carbonyl compounds of the formula (I) ##STR1## in which Q represents oxygen or sulphur,R.sup.1 and R.sup.2 are identical or different and independently of one another represent a radical from the series comprising heterocyclyl, heterocyclylamino and heterocyclylimino, in each case optionally substituted and bonded via N, with the exception of optionally substituted pyrazolylamino in the meaning of R.sup.1,and salts of the compounds of the formula (I), furthermore to processes for their preparation, and to their use as herbicides.
    Type: Grant
    Filed: November 15, 1994
    Date of Patent: March 11, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Jochem Riebel, Ernst R. F. Gesing, Klaus-Helmut M uller, Peter M uller, Kurt Findeisen, Hans-Joachim Santel, Klaus L urssen, Robert R. Schmidt
  • Patent number: 5604181
    Abstract: Herbicidal compounds of formula (I) and salts thereof, where A is --N.dbd. or --CH.dbd.; X is --OH, --OR.sup.10, --SH, --SR.sup.10, --SCN, NH.sub.2, --NHacyl, --CH.sub.2 OH, --CH.sub.2 OR.sup.9 or --CN; R.sup.1 and R.sup.2, which may be the same or different, each represent alkyl, alkoxy, haloalkyl, haloalkoxy, halo, alkylamino or dialkylamino; R.sup.3 is --CN, --COOR.sup.5, --CONR.sup.6 R.sup.7, --CSNH.sub.2, --CHO, --CH.dbd.Z, --CH(Oalkyl).sub.2, --CH.sub.2 OH, --CH.sub.2 OR.sup.9, --COSR.sup.4a, --CS.sub.2 R.sup.4a, or a substituted or unsubstituted 5- or 6-membered heterocyclic group linked via a ring carbon atom which is between two ring heteroatoms; R.sup.4 and R.sup.4a, which may be the same or different, are each H, or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl or heteroaryl group; R.sup.
    Type: Grant
    Filed: March 8, 1995
    Date of Patent: February 18, 1997
    Assignee: Agrevo UK Limited
    Inventors: Thomas L. Hough, Peter S. Gates
  • Patent number: 5602076
    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: March 29, 1995
    Date of Patent: February 11, 1997
    Assignee: Zeneca Limited
    Inventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey
  • Patent number: 5595958
    Abstract: Herbicidal 3-substituted pyridine compounds and derivatives thereof of the formula: ##STR1## wherein Ar is a substituted or unsubstituted 5- or 6-membered heteroaryl group having 1, 2 or 3 ring nitrogen atoms with the remainder of the ring atoms being carbon; a substituted or unsubstituted 5-membered heteroaryl group having a ring heteroatom of oxygen or sulfur with the remainder of the ring atoms being carbon; or a substituted or unsubstituted 5-membered heteroaryl group having one ring nitrogen atom and either an oxygen or sulfur ring heteroatom with the remainder of the ring atoms being carbon. Herbicidal compositions containing such 3-substituted pyridine compounds and derivatives thereof and methods of controlling undesirable vegetation employing these compounds and derivatives are also disclosed. The compounds in which XR is hydroxyl are also useful as intermediates for producing the disclosed 3-substituted pyridine derivatives.
    Type: Grant
    Filed: May 2, 1994
    Date of Patent: January 21, 1997
    Assignee: Zeneca Limited
    Inventors: Hsiao-Ling M. Chin, Nhan H. Nguyen, David B. Kanne, David L. Lee
  • Patent number: 5585384
    Abstract: There have been discovered new bicyclic pyrrolidone compounds such as: ##STR1## which are useful as insecticides, ascaricides and herbicides.
    Type: Grant
    Filed: August 17, 1994
    Date of Patent: December 17, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans J. Santel, Robert R. Schmidt, Ulrike Wachendorff-Neumann, Christoph Erdelen, Thomas Bretschneider, Reiner Fischer, Hermann Hagemann, Bernd-Wieland Kr uger, Klaus L urssen
  • Patent number: 5559081
    Abstract: Herbicidal sulfonamides of the formula: ##STR1## and salts thereof, where: A represents a substituted or unsubstituted benzene ring, or a 5- or 6-membered substituted or unsubstituted heteroaromatic ring; Q is --O--, --S-- or a group --CXX'--; X and X', which may be the same or different, are each hydrogen, halogen, cyano, an optionally-substituted alkyl group, or a group --OR.sup.a, --SR.sup.a, or --COR.sup.b ; or one of X and X' represents hydroxy and the other is as defined above; or X and X' together represent .dbd.O or .dbd.S; R.sup.a is an optionally-substituted alkyl, aryl or acyl group; R.sup.b is an optionally-substituted alkyl or aryl group, or a group --OR.sup.c or --NR.sup.c R.sup.d ; R.sup.c and R.sup.d, which may be the same or different, are each hydrogen, or an optionally-substituted alkyl or aryl group; Y is nitrogen or a group CR.sup.9 ; R.sup.1 is an optionally-substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, benzoheterocyclyl or amino group; R.sup.
    Type: Grant
    Filed: May 6, 1994
    Date of Patent: September 24, 1996
    Assignee: Agrevo UK Limited
    Inventors: Peter S. Gates, Graham P. Jones, David E. Saunders
  • Patent number: 5556829
    Abstract: Compounds of formula ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and X have the meanings reported in the description, can be used in compositions for agricultural use in particular as herbicides in the defense of useful crops from weeds.
    Type: Grant
    Filed: May 27, 1994
    Date of Patent: September 17, 1996
    Assignees: Zambon Group S.p.A., Agrimont S.p.A.
    Inventors: Giovanni Camaggi, Dario Chiarino, Mario Fantucci, Giovanni Meazza
  • Patent number: 5532208
    Abstract: There are disclosed novel pyrimidone derivatives of the formula I: ##STR1## wherein X is hydrogen, chlorine, methyl or ethyl, R.sup.2 is hydrogen or methyl, and Q is ##STR2## A is fluorine, chlorine or bromine; and R.sup.1 is alkyl, alkenyl, alkynyl, alkoxyalkyl or haloalkyl.Also disclosed are a herbicidal composition containing a herbicidally effective amount of the compound (I) as an active ingredient and a method for exterminating undesired weeds by applying a herbicidally effective amount of the compound (I) to an area where the undesired weeds grow or will grow.
    Type: Grant
    Filed: August 17, 1994
    Date of Patent: July 2, 1996
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Eiki Nagano, Susumu Takemura, Masayuki Enomoto, Masaharu Sakaki, Satoru Kizawa
  • Patent number: 5527763
    Abstract: A herbicide containing a pyrimidine or triazine derivative of the formula (I): ##STR1## [wherein A is a furan ring, a pyrimidine ring, a 1,2,4-triazine ring or the like which may suitably be substituted, R is a hydroxyl group or a lower alkoxy group, each of R.sup.1 and R.sup.2 which may be the same or different, is a halogen atom, a lower alkyl group or a lower alkoxy group, W is an oxygen atom or a sulfur atom, and Z is nitrogen or a methine group] and its salt, as an active ingredient, is presented. The pyrimidine or triazine derivative of the present invention has excellent herbicidal effects against noxious weeds in paddy fields, upland fields and non-agricultural fields.
    Type: Grant
    Filed: December 8, 1993
    Date of Patent: June 18, 1996
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masahiro Miyazaki, Masafumi Matsuzawa, Takumi Yoshimura, Kuniaki Shimizu, Shigehiko Tachikawa
  • Patent number: 5506192
    Abstract: Substituted phthalides and heterocyclic phthalides and derivatives thereof which are useful as herbicides are described.
    Type: Grant
    Filed: February 23, 1994
    Date of Patent: April 9, 1996
    Assignee: Sandoz Ltd.
    Inventors: Richard J. Anderson, Ian S. Cloudsdale, Takeo Hokama
  • Patent number: 5480857
    Abstract: 4-heteroaroylisoxazole derivatives of formula I: ##STR1## wherein: Ar represents an optionally substituted group Het, wherein Het represents a first heterocyclic ring containing from one to four heteroatoms in the ring selected from oxygen, nitrogen and sulphur, which is optionally fused with a benzene, or carbocyclic or second heterocyclic ring (which is optionally saturated or partially saturated) to form a bicyclic system, wherein the first heterocyclic ring of the group Het is attached to the carbonyl group in the 4-position of the isoxazole ring;R represents hydrogen or --CO.sub.2 R.sup.3 ;R.sup.1 represents alkyl or haloalkyl or a cycloalkyl group optionally substituted by one or more groups R.sup.4 ;R.sup.3 and R.sup.4 independently represent alkyl or haloalkyl;agriculturally acceptable salts thereof and their use in weed control is described.
    Type: Grant
    Filed: September 17, 1993
    Date of Patent: January 2, 1996
    Assignee: Rhone-Poulenc Agriculture Limited
    Inventors: Susan M. Cramp, Philip H. G. Smith
  • Patent number: 5478799
    Abstract: The present invention provides an N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring represented by formula [I]: ##STR1## wherein R.sup.1 represents an alkyl group, an alkenyl group, or the like, R.sup.2 represents a hydrogen atom, an alkyl group, or the like. R.sup.3 and R.sup.4 represent independently an alkyl group or a nitrogen atom; or the salt of the same, a method for producing the same, and a biocide containing the same as an active ingredient. The N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring according to the present invention exhibits superior effects against blight caused by plant pathogenic fungi belonging to Oomycetes such as downy mildew, late blight, or the like in a low concentration as well as controls weeds occurring in paddy fields and plowed fields.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: December 26, 1995
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Ikumi Urushibata, Takumi Yoshimura, Takeshi Deguchi, Norihisa Yonekura, Junetsu Sakai, Shigeru Hayashi
  • Patent number: 5461824
    Abstract: Tree growth is suppressed by placing an implant below the bark layer of the tree at each of a plurality of sites spaced around the circumference of the trunk of the tree, each implant containing a unit dose of active ingredient selected from flurprimidol, paclobutrazol, and uniconazole.
    Type: Grant
    Filed: August 2, 1994
    Date of Patent: October 31, 1995
    Assignee: DowElanco
    Inventor: Ronald L. Cassell
  • Patent number: 5451563
    Abstract: Fungicidal heterocyclic silyl compounds of the general formula ##STR1## have been discovered wherein Het is a six membered heterocyclic moiety; R is hydrogen or a trisubstituted silyl group; R.sup.1, R.sup.2 and R.sup.3 are independently selected from substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, arylalkyl or pyridyl groups; m is 0 or 1 and n is zero, one or two.
    Type: Grant
    Filed: March 16, 1994
    Date of Patent: September 19, 1995
    Assignee: Rohm and Haas Company
    Inventors: Steven H. Shaber, Edward M. Szapacs, Reynolds Charles H.
  • Patent number: 5439874
    Abstract: The invention relates to novel substituted bicyclo[3.1.0]hexanes of the formula ##STR1## in which R.sup.1 represents, e. g., hydroxyl or alkoxy,R.sup.2 to R.sup.8 represent, e. g., hydrogen or alkyl,R.sup.9 and R.sup.10 represent, e.g., methyl or methoxy,X represents, e.g., oxygen,Y represents, e.g., oxygen or sulphur andZ represents, e.g., CH or N,as well as salts of the free acid (R.sup.1 =OH) and their further functional derivatives, and furthermore to processes and novel intermediates for their preparation, and to their use as herbicides.In addition, a novel process is described for preparing certain 2-keto-bicyclo[3.1.0]hexanes, which are required as intermediates, starting from correspondingly substituted .alpha.,.beta.-unsaturated carbonyl compounds (of the methacrolein type) and .beta.-keto acid esters (of the acetoacetic acid ester type).
    Type: Grant
    Filed: July 21, 1993
    Date of Patent: August 8, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Mark W. Drewes, Rolf Kirsten, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
  • Patent number: 5411934
    Abstract: The present invention provides a novel alkanoic acid amide derivative of the formula, ##STR1## (wherein R.sup.1 is a hydrogen atom, an alkyl group or an alkoxyalkoxy group, R.sup.2 is a group of -SO.sub.2 R or a hydroxyl group, R.sup.5 is an alkyl group, R.sup.3 is an alkyl group, a cycloalkyl group, a cycloalkenyl group or a phenyl group, R.sup.4 is a hydrogen atom or an alkyl group, X and Y may be the same or different and are an alkoxy group, an alkylamino group or a dialkylamino group, and Z is a methine group or a nitrogen atom) and its salt, a process for preparing the same and a herbicidal composition containing the same as an effective ingredient.This compound kills annual and perennial weeds grown in paddy fields and upland fields at a small dose, and is safe to a useful crop plant.
    Type: Grant
    Filed: July 30, 1992
    Date of Patent: May 2, 1995
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Takumi Yoshimura, Keiji Toriyabe, Katsumi Masuda, Ryo Hanai
  • Patent number: 5401710
    Abstract: Herbicidal compositions which comprise one or more compounds of the formula: ##STR1## or salts thereof, where: A is --CH.dbd. or --N.dbd.;R.sup.1 is alkyl, alkoxy, halo or --NR.sup.7 R.sup.8 ;R.sup.2 is alkyl or alkoxy;R.sup.3 is hydrogen, alkenyl or alkynyl, or substituted or unsubstituted alkyl, alkanoyl or alkoxycarbonyl;R.sup.4 is hydrogen or substituted or unsubstituted alkyl;R.sup.5 is halo or substituted or unsubstituted alkyl or aryl; andX is --CO.sub.2 R.sup.6, --CONR.sup.7 R.sup.8 or --CN;in which R.sup.6, R.sup.7 and R.sup.8, which may be the same or different, each represent hydrogen, substituted or unsubstituted alkyl, or one of R.sup.7 and R.sup.8 represents substituted amino;in association with a suitable carrier and/or surface active agent, together with the compounds of formula I per se where R.sup.5 represents isopropyl, and/or X represents methoxycarbonyl, and salts thereof.
    Type: Grant
    Filed: July 9, 1993
    Date of Patent: March 28, 1995
    Assignee: Schering Agrochemicals Limited
    Inventor: Peter S. Gates
  • Patent number: 5391537
    Abstract: The present invention is to provide a novel picolinic acid derivative having the formula, ##STR1## (wherein R is a hydrogen atom, an alkyl group or others, R.sup.1 and R.sup.2 are the same or different, and are an alkyl group, an alkoxy group or others, X is a cyano group, a phenoxy group or others, Y is an oxygen atom or others, and n is 0 or 1) or a salt thereof; a method for preparing the same; and a herbicidal composition containing the same as an active ingredient.The picolinic acid derivative or the salt thereof of the present invention achieves an excellent herbicidal effect at a low dosage, and is effective for controlling the growth of various weeds in a wide range.The picolinic acid derivative or the salt thereof of the present invention can be applied to a paddy field, a cultivated field, a non-agricultural land and the like as a herbicidal composition.
    Type: Grant
    Filed: October 14, 1992
    Date of Patent: February 21, 1995
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Fumiaki Takabe, Yoshihiro Saito, Masatoshi Tamaru, Shigehiko Tachikawa, Ryo Hanai
  • Patent number: 5380700
    Abstract: The present invention provides a novel pyridine derivative having the following general formula and its salt: ##STR1## wherein R is a hydrogen atom, a hydroxyl group, an alkoxy group, an alkoxyalkoxy group, and derivatives;R.sup.1 and R.sup.2 may be the same or different, and are a hydrogen atom, an alkoxy group, a halogen atom, an alkylamino group, a dialkylamino group;Z is a methine group or a nitrogen atom;X.sup.1 is an acylamino group, a cycloalkyl group, a halogen-substituted alkoxy group, an alkenyloxy group, an alkynyloxy group, an alkoxycarbonyl group, an alkylamino group, a dialkylamino group, a phenyl group.The pyridine derivative and its salt of the present invention achieve an excellent herbicidal effect on annual and perennial weeds growing in paddy fields and upland fields at a very small dosage.The pyridine derivative and its salt of the present invention have safety to rice, wheat, cotton and corn, and can be suitably applied as a herbicide to a field where these plants are cultivated.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: January 10, 1995
    Assignees: Kumiai Chemical Industries Co., Ltd., Ihara Chemical Industries Co., Ltd.
    Inventors: Masahiro Miyazaki, Masafumi Matsuzawa, Keiji Toriyabe, Michiya Hirata
  • Patent number: 5360576
    Abstract: Compounds of the formula (I) in which the symbols have the following meanings: R.sup.1 is straight-chain or branched (C.sub.3 -C.sub.2)alkenyl containing a terminal double bond, it being possible for one or two non-adjacent CH.sub.2 groups to be replaced by O and/or S atoms, A and B, independently of one another, are phenyl, diazine-2,5-diyl or diazine-3,6-diyl, with the proviso that one of the groups A or B is phenyl and the other is diazine, X is O or S, R.sup.2, R.sup.3 and R.sup.4, independently of one another, are H, straight-chain (C.sub.1 -C.sub.10)alkyl or branched (C.sub.3 -C.sub.10 )alkyl, R.sup.2, R.sup.3 and R.sup.4 not simultaneously being H, have the property of increasing the phase width in CC mixtures or depressing the melting point.
    Type: Grant
    Filed: January 21, 1993
    Date of Patent: November 1, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karsten Blatter, Claus Escher, Takamasa Harada, Peter Harnischfeger, Wolfgang Hemmerling