1,2-oxazoles (including Hydrogenated) Patents (Class 504/271)
  • Patent number: 6239076
    Abstract: The present invention relates to 2-(5-isoxazolinylmethyloxyphenyl)-4,5,6,7-tetrahydro-2H-indazole derivatives of formula 1, their preparation method and their use as herbicides. As the compounds have excellent herbicidal activity against paddy weeds comprising ECHOR, SCPJU, MOOVA, CYPSE and SAGPY, and better selectivity, the compounds of the present invention are typically useful as herbicides for control of paddy weeds in conditions with seeded rice and transferred rice.
    Type: Grant
    Filed: October 6, 2000
    Date of Patent: May 29, 2001
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Eung Kul Ryu, Dong Ju Jeon, Jong Hwan Song, Hyoung Rae Kim, Jung No Lee, Kyoung Mahn Kim, Kwang Yun Cho
  • Patent number: 6235682
    Abstract: Compositions comprising a herbicide wherein it is desired that the compound not be retained by the plant foliage, and a repellant adjuvant, wherein the repellant modifies the surface properties of the composition so that retention of the composition on foliage of a cultivated plant is reduced are described. In particular, the herbicide composition comprises a repellant adjuvant that is an aqueous solution of an alkyltrialkoxysilane such as methyltrimethoxysilane and a water soluble silane coupling agent such as N-(2-aminoethyl)-3-aminopropyltrimethoxysilane or an aqueous solution of an organosiliconate such as sodium methyl siliconate. Methods are described for using these compositions to prevent weeds without injury to cultivated plants, which plants include crop plants, food plants, turfgrass, ornamental plants, and garden plants.
    Type: Grant
    Filed: July 15, 1999
    Date of Patent: May 22, 2001
    Assignees: Board of Trustees operating Michigan State University, Dow Corning Corporation
    Inventors: Donald Penner, Christy L. Sprague, Richard F. Burow
  • Patent number: 6165944
    Abstract: 4-(3-Heterocyclyl-1-benzoyl)pyrazoles of the formula I ##STR1## where: R.sup.1 and R.sup.3 are each hydrogen, nitro, halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, aminosulfonyl, N-alkylaminosulfonyl, N,N-dialkyl)aminosulfonyl, N-alkylsulfonylamino, N-haloalkylsulfonylamino, N-alkyl-N-alkylsulfonylamino or N-alkyl-N-haloalkylsulfonylamino;R.sup.2 is a 5- or 6-membered heterocyclyl radical with or without substitution which comprises 1 to 4 identical or different hetero atoms from the following group: oxygen, sulfur or nitrogen;R.sup.4 is hydrogen, halogen or alkyl;R.sup.5 is substituted pyrazole which is attached in position 4;and agriculturally useful salts thereof; processes for preparing the 4-(3-heterocyclyl-1-benzoyl)pyrazoles; compositions comprising them; and the use of these derivatives or these compositions comprising them for controlling undesirable plants.
    Type: Grant
    Filed: June 16, 1998
    Date of Patent: December 26, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang von Deyn, Regina Luise Hill, Ernst Baumann, Stefan Engel, Guido Mayer, Joachim Rheinheimer, Matthias Witschel, Ulf Misslitz, Oliver Wagner, Martina Otten, Helmut Walter, Karl-Otto Westphalen
  • Patent number: 6156701
    Abstract: This invention is directed to a method of selectively controlling undesirable vegetation in corn, comprising application of an herbicidally effective amount of an isoxazole having the formula ##STR1## wherein R is a straight- or branched-chain alkyl having up to six carbon atoms, to the locus of such vegetation.
    Type: Grant
    Filed: November 24, 1999
    Date of Patent: December 5, 2000
    Assignee: Rhone-Poulenc Agro
    Inventors: Alan Gamblin, Ashley Slater
  • Patent number: 6150303
    Abstract: Substituted 3-phenylisoxazolines I, and their salts and enol ethers, are described as herbicides ##STR1## where X.dbd.--O--, --S--, --N(R.sup.9)--;R.sup.1 .dbd.CN, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylsulfonyl;R.sup.2 .dbd.H or unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkyl)carbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.2 -C.sub.6 -alkenyl, (C.sub.2 -C.sub.6 -alkenyl)carbonyl, C.sub.2 -C.sub.6 -alkynyl, (C.sub.2 -C.sub.6 -alkynyl)carbonyl;R.sup.3 .dbd.H, halogen;R.sup.4 .dbd.CN, halogen, C.sub.1 -C.sub.3 -haloalkyl;R.sup.5 .dbd.H, CN, halogen, C.sub.1 -C.sub.3 -haloalkyl;R.sup.6 .dbd.H, CN, halogen, C.sub.1 -C.sub.3 -haloalkyl or unsubstituted or substituted C.sub.1 -C.sub.6 -alkoxy;R.sup.7 .dbd.CN, halogen;R.sup.8 in position .alpha., R.sup.7 in this case being in position .beta., or in position .beta., R.sup.7 in this case being in position .alpha., is1) H, OH, SH, CN, NO.sub.2, halogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: January 21, 2000
    Date of Patent: November 21, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Olaf Menke, Markus Menges, Gerhard Hamprecht, Robert Reinhard, Peter Schafer, Cyrill Zagar, Karl-Otto Westphalen, Ulf Misslitz, Helmut Walter
  • Patent number: 6147031
    Abstract: A compound represented by the general formula [I] ##STR1## (wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group; R.sup.2 is a C.sub.1 -C.sub.6 alkylsulfonyl group and the like; R.sup.3 and R.sup.4 are each independently hydrogen or a C.sub.1 -C.sub. 6 alkyl group; R.sup.5 is hydrogen or a benzyl group or the like; R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are each independently hydrogen or a C.sub.1 -C.sub.6 alkyl group.) or a herbicide containing a salt thereof, intermediate preparing therefor, and the said compound.
    Type: Grant
    Filed: December 8, 1998
    Date of Patent: November 14, 2000
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Hiroyuki Adachi, Katsunori Tanaka, Akihiro Takahashi, Masami Koguchi
  • Patent number: 6037312
    Abstract: Isoxazole derivatives of the formula (I), ##STR1## and herbicides containing the above isoxazole derivatives as active ingredients, which can selectively control grass weeds and broad-leaved weeds simultaneously at a low dosage as a single herbicide, without causing phytotoxicity on corn, sorgo, cotton, wheat and barley.
    Type: Grant
    Filed: February 3, 1999
    Date of Patent: March 14, 2000
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Yoriyuki Takashima, Hideki Kamano, Masashi Sakamoto
  • Patent number: 6017853
    Abstract: Novel 1-substituted methyltetrazolinones of the formula (I) ##STR1## wherein R.sup.1 represents a 5-membered heterocyclic radical which has 1 to 3 heteroatoms selected arbitrarily from the group consisting of N, O and S and which is optionally substituted by halogen and/or C.sub.1-4 alkyl, or represents oxiran-2-yl, optionally chloro-substituted pyridyl or C.sub.1-4 alkyl-S(O).sub.m --wherein m represents 0, 1 or 2, or represents a C.sub.3-6 alicyclic hydrocarbon radical; R.sup.2 and R.sup.3 represent, independently of one another, C.sub.1-4 alkyl, C.sub.3-7 cycloalkyl or optionally substituted phenyl, or R.sup.2 and R.sup.3 may form, together with the N-atom to which they are bonded, an optionally substituted ring; R.sup.4 represents a hydrogen atom or methyl; and n represents 0 or 1; as well as for their preparation processes and novel intermediates in their production. The inventive compounds of formula (I) are used as herbicides.
    Type: Grant
    Filed: July 9, 1997
    Date of Patent: January 25, 2000
    Assignee: Nihon Bayer Agrochem K.K.
    Inventors: Toshio Goto, Yoshinori Kitagawa, Seishi Ito, Katsuhiko Shibuya, Chieko Ueno, Yoshiko Kyo
  • Patent number: 6013805
    Abstract: The invention relates to intermediates to herbicidal compounds of formulae (Ia), (Ib) or (Ic): ##STR1##
    Type: Grant
    Filed: September 29, 1998
    Date of Patent: January 11, 2000
    Assignee: Rhone-Poulenc Agriculture Ltd
    Inventor: David William Hawkins
  • Patent number: 6004904
    Abstract: The invention relates to a method for the protection of a turfgrass at a locus which comprises applying to said locus an isoxazole derivative of formula (I), wherein R is hydrogen or --CO.sub.2 R.sup.3, wherein R.sup.3 is as defined below; R.sup.1 is cyclopropyl; R.sup.2 is selected from halogen, --S(O).sub.p R.sup.4 and C.sub.1-4 alkyl or haloalkyl; n is two or three; p is zero, one or two; R.sup.3 is C.sub.1-4 alkyl and R.sup.4 is C.sub.1-4 alkyl; and to compositions containing the same.
    Type: Grant
    Filed: April 10, 1998
    Date of Patent: December 21, 1999
    Assignee: Rhone-Poulenc Inc.
    Inventors: Thomas Edward Vrabel, Wilbur Fell Evans
  • Patent number: 5985799
    Abstract: Compounds of Formula (I), and their N-oxides and agriculturally-suitable salts, are disclosed which are useful in controlling undesired vegetation, wherein J is Formula (II), Q is represented by Q-1 through Q-4 and X, Y, Z, R.sup.1-19, m, n, p, q, and r are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (I) and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula (I).
    Type: Grant
    Filed: May 12, 1998
    Date of Patent: November 16, 1999
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Chi-Ping Tseng
  • Patent number: 5939360
    Abstract: The present invention is directed to a compound of formula ?I!: ##STR1## or a salt thereof in which R.sub.1 is a a C.sub.1-6 alkyl group, R.sup.2 is a halogen atom, a C.sub.1-6 alkylthio group, a C.sub.1-6 alkylsulfinyl group or a C.sub.1-6 alkylsulfonyl group, R.sup.3 and R.sup.4 are each independently hydrogen, a C.sub.1-6 alkyl group or a C.sub.1-6 haloalkyl group, and R is hydrogen or a C.sub.1-6 alkyl group. The present invention is further directed to a compound of formula ?1! or a salt thereof, as described above and in which R.sup.1 and R.sup.3 are methyl, R.sup.2 is chlorine or methylsulfonyl, R.sup.4 is hydrogen, and R is methyl or ethyl. In addition, the present invention is directed to a herbicidal composition, characterized in that it contains as active agent one or more compounds of formula ?I! or salt thereof in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 are as described above.
    Type: Grant
    Filed: December 15, 1998
    Date of Patent: August 17, 1999
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Hiroyuki Adachi, Masao Yamaguchi, Masami Koguchi, Akihiro Takahashi, Takashi Kawana, Katsunori Tanaka, Osamu Miyahara
  • Patent number: 5905057
    Abstract: The invention relates to a liquid composition comprising:(a) a herbicidally effective amount of at least one alkyl 4-benzoylisoxazole-3-carboxylate derivative; and(b) at least one N-alkylpyrrolidinone derivative,said composition being substantially stable.
    Type: Grant
    Filed: November 6, 1997
    Date of Patent: May 18, 1999
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Jacqueline Forget, David Alan Long, Gilbert Antoine Perez
  • Patent number: 5888941
    Abstract: Compounds of general formula I and their salts and solvates are antifungal agents and as such are useful in the treatment of various fungal infections. Pharmaceutical compositions including these compounds and processes for their preparation are also provided.
    Type: Grant
    Filed: March 31, 1997
    Date of Patent: March 30, 1999
    Assignee: J. Uriach & Cia. S.A.
    Inventors: Javier Bartroli, Enric Turmo, Manuel Anguita
  • Patent number: 5863865
    Abstract: This invention relates to 4-benzoylisoxazoles of formula (I) ##STR1## as well as herbicide compositions containing them and their use as herbicides.
    Type: Grant
    Filed: October 28, 1997
    Date of Patent: January 26, 1999
    Assignee: Zeneca Limited
    Inventors: David L. Lee, Nigel Barnes
  • Patent number: 5856274
    Abstract: The invention relates to 4-benzoylisoxazoles having the formula: ##STR1## wherein: R is hydrogen or --CO.sub.2 R.sup.5 ;R.sup.1 is alkyl, cyclopropyl or 1-methylcyclopropyl;R.sup.2 is chlorine, bromine, optionally substituted alkyl, alkoxy, haloalkoxy, --S(O).sub.p R.sup.61, nitro or cyano;R.sup.3 is --S(O).sub.n R.sup.6 ;R.sup.4 is hydrogen, fluorine, chlorine, bromine, optionally substituted alkyl, alkoxy, S(O).sub.q R.sup.61, nitro, cyano or --CO.sub.2 R.sup.52 ;R.sup.5 and R.sup.61, which are the same or different, are each alkyl or haloalkyl;R.sup.52 is alkyl;R.sup.6 is alkyl, alkenyl or alkynyl optionally substituted by one or more halogen; andn, p and q, which are the same or different, are each zero, one or two;and their use as herbicides.
    Type: Grant
    Filed: September 14, 1995
    Date of Patent: January 5, 1999
    Assignee: Rhone-Poulenc Agriculture Limited
    Inventors: Susan Mary Cramp, Claude Lambert, Derek Ian Wallis, Thomas Yarwood
  • Patent number: 5849928
    Abstract: The invention relates to compounds of formulae (Ia), (Ib) or (Ic): ##STR1## and to their use as herbicides.
    Type: Grant
    Filed: March 21, 1997
    Date of Patent: December 15, 1998
    Assignee: Rhone-Poulenc Agriculture Limited
    Inventor: David William Hawkins
  • Patent number: 5846906
    Abstract: Herbicidally active phenyldiketone compounds of the formula I ##STR1## in which the substituents have the following meanings: L and M are hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, it being possible for these groups to be unsubstituted or substituted by one to five halogen atoms or C.sub.1 -C.sub.4 -alkoxy, or halogen, cyano, nitro, a group --(Y).sub.n --S(O).sub.m R.sup.7 or a group --(Y).sub.n --CO--R.sup.8,Z is a 5- or 6-membered heterocyclic saturated or unsaturated radical which has one to three hetero atoms selected from the group consisting of oxygen, sulfur or nitrogen and which is unsubstituted or substituted by halogen, cyano, nitro, a group --CO--R.sup.8, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, di-C.sub.1 -C.sub.
    Type: Grant
    Filed: July 30, 1997
    Date of Patent: December 8, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang von Deyn, Regina Luise Hill, Uwe Kardorff, Stefan Engel, Martina Otten, Marcus Vossen, Peter Plath, Harald Rang, Albrecht Harreus, Hartmann Konig, Helmut Walter, Karl-Otto Westphalen, Ulf Misslitz
  • Patent number: 5834402
    Abstract: Isoxazol-4-ylbenzoyl derivatives of the formula I ##STR1## where the substituents have the meanings described in the specification; and agriculturally customary salts thereof.
    Type: Grant
    Filed: August 22, 1997
    Date of Patent: November 10, 1998
    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: 5827799
    Abstract: An object of the invention is to provide herbicides which are completely selective to crops such as paddy rice, soybeans and cotton and have an excellent herbicidal activity on weeds.The invention relates to ether compounds of the general formula (I) ##STR1## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the same meanings as defined in the text and herbicides containing said compounds as active components.
    Type: Grant
    Filed: July 19, 1996
    Date of Patent: October 27, 1998
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Kiyoshi Arai, Fumiaki Koizumi, Hiroyuki Suzuki, Takeshi Kakimoto, Sadafumi Koda
  • Patent number: 5783520
    Abstract: There is provided an aqueous dispersion of microcapsules containing the herbicide clomazone dissolved in an inert high boiling organic solvent which is an edible oil. Vapor transfer of the herbicide outside the targeted area is controlled without substantial sacrifice of the efficacy of the herbicide.
    Type: Grant
    Filed: December 4, 1996
    Date of Patent: July 21, 1998
    Assignee: Monsanto Company
    Inventors: Helen L. Anderson, Salim M. Hakimi, Alan P. Lundstedt, Tracy A. Powers, Sudabathula Rao, Alan J. Stern
  • Patent number: 5780393
    Abstract: There are provided isoxazole- and isothiazole-5-carboxamide compounds of formula I ##STR1## which are useful for the control of undesirable monocotyledenous and dicotyledenous plant species in the presence of crops such as cereal and leguminous crops. Also provided are herbicidal compositions and methods of using same.
    Type: Grant
    Filed: August 23, 1996
    Date of Patent: July 14, 1998
    Assignee: American Cyanamid Company
    Inventor: Trevor W. Newton
  • Patent number: 5756423
    Abstract: A method of controlling the growth of plants comprising applying to the locus of such plants an herbicidally effective amount of a compound exhibiting an IC.sub.50 value of less than about 300 nM in the inhibition of farnesyl pyrophosphate synthase in daffodil chromoplasts.
    Type: Grant
    Filed: July 10, 1997
    Date of Patent: May 26, 1998
    Assignee: Zeneca Limited
    Inventors: Thomas H. Cromartie, Karl J. Fisher
  • Patent number: 5747424
    Abstract: The invention relates to 4-substituted isoxazole derivatives of formula I: ##STR1## wherein R, R.sup.1, R.sup.2, Q and n have the meanings defined in the description, which possess valuable herbicidal properties.
    Type: Grant
    Filed: May 1, 1997
    Date of Patent: May 5, 1998
    Assignee: Rhone-Poulenc Agriculture Ltd.
    Inventors: David Alan Roberts, Susan Mary Cramp, Derek Ian Wallis, Jean-Paul Bulot
  • Patent number: 5739085
    Abstract: O-(Oximino)ethylcyclohexenone oxime ethers I ##STR1## (R.sup.1 and R.sup.2 =C.sub.1 -C.sub.6 -alkyl; R.sup.3 =unsubstituted or substituted phenyl, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkenyl or C.sub.3 -C.sub.4 -alkynyl, which in each case can be substituted by halogen, C.sub.1 -C.sub.3 -alkyl, unsubstituted or substituted phenyl or unsubstituted or substituted phenoxy;R.sup.4 =C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, unsubstituted or substituted phenylthio-C.sub.1 -C.sub.6 -alkyl, N-(C.sub.1 -C.sub.4 -alkylsulfonyl)-N-(C.sub.1 -C.sub.4 -alkyl)aminomethyl, unsubstituted or substituted C.sub.3 -C.sub.7 -cycloalkyl or C.sub.5 -C.sub.
    Type: Grant
    Filed: May 5, 1995
    Date of Patent: April 14, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulf Misslitz, Albrecht Harreus, Hartmann Konig, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
  • Patent number: 5723414
    Abstract: A class of 5-aryl-isoxazolinones and compositions thereof which are useful in the control of weeds is of the general formula ##STR1## wherein Ar is a substituted or unsubstituted aryl or heteroaryl;R.sup.2 is alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl or alkoxyalkyl, all of which may be substituted with one or more halogen atoms;R.sup.4 is alkynyl or alkoxyalkyl, both of which may be substituted with one or more halogen atoms; andX is an oxygen or a sulfur atom.
    Type: Grant
    Filed: January 21, 1997
    Date of Patent: March 3, 1998
    Assignee: Rohm and Haas Company
    Inventor: Colin Michael Tice
  • Patent number: 5679341
    Abstract: A novel organic compound, designated botcinol, has been isolated which possesses significant phytotoxic activity and which may be used as a biodegradable contact herbicide. The compound is a hydroxylated nonalactone that is esterified with 4-hydroxy-2-decenoic acid, and has the following structure: ##STR1## Botcinol is produced by culture of a novel strain of the fungus Botrytis cinerea, designated UK 185, and may be subsequently recovered from the culture medium and purified.
    Type: Grant
    Filed: July 6, 1995
    Date of Patent: October 21, 1997
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Horace G. Cutler, Stephen R. Parker
  • 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: 5658858
    Abstract: The invention relates to 4-benzoylisoxazole compounds, compositions containing them, a process for preparation, and their use as herbicides.
    Type: Grant
    Filed: September 6, 1996
    Date of Patent: August 19, 1997
    Assignee: Rhone-Poulenc Argriculture Limited
    Inventors: Angela Jacqueline Bailey, Michael Gingell, David William Hawkins
  • Patent number: 5656573
    Abstract: The invention relates to 4-substituted isoxazole derivatives of formula I: ##STR1## wherein R, R.sup.1, R.sup.2, Q and n have the meanings defined in the description, which possess valuable herbicidal properties.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: August 12, 1997
    Assignee: Rhone-Poulenc Agriculture Ltd.
    Inventors: David Alan Roberts, Susan Mary Cramp, Paul Alfred Cain, Derek Ian Wallis, Jean-Paul Bulot, Gillian Mary Little, Brian Malcolm Luscombe
  • Patent number: 5635447
    Abstract: A herbicide composition which comprises a herbicide and a small but herbicide absorption enhancing effective amount of a water soluble, non-aromatic polyorganic acid or a salt or copolymer thereof such as polyaspartic acid.
    Type: Grant
    Filed: March 22, 1996
    Date of Patent: June 3, 1997
    Assignee: Donlar Corporation
    Inventor: J. Larry Sanders
  • 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: 5618775
    Abstract: Mixtures of optically active cyclohexenone oxime ethers having R- and S-configuration in the oxime ether moiety of the formula I ##STR1## (R.sup.1 =C.sub.1 -C.sub.6 -alkyl; ##STR2## X=C.sub.1-C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl; m=0-3 or 1-4 where all X's are halogen;n=0-3 or 1-5 where all X's are halogen;R.sup.2 =C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, substituted or unsubstituted C.sub.3 -C.sub.7 -cycloalkyl, substituted or unsubstituted C.sub.5 -C.sub.7 -cycloalkenyl, substituted or unsubstituted 5-membered saturated heterocyclic structure, substituted or unsubstituted 6- or 7-membered heterocyclic structure, substituted or unsubstituted 5-membered heteroaromatic structure, substituted or unsubstituted phenyl or pyridyl)and their agriculturally useful salts and esters with C.sub.1 -C.sub.10 -carboxylic acids and inorganic acids.
    Type: Grant
    Filed: August 11, 1994
    Date of Patent: April 8, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Wolfgang Ladner, Helmut Walter, Karl-Otto Westphalen, Uwe Kardorff, Matthias Gerber
  • Patent number: 5597780
    Abstract: An herbicidal composition containing from 1 to 4 pounds of clomazone per gallon of formulation and having a clomazone volatility less than fifty percent of that of an emulsifiable concentrate containing four pounds of clomazone per gallon of formulation is prepared by the interfacial reaction of polymethylene polyphenyl isocyanate with a polyfunctional amine selected from ethylenediamine, diethylenetriamine, triethylenetetramine, 1,6-hexanediamine, and their mixtures in an aqueous phase optionally containing from 0.05 to 0.25 weight percent of a xanthan gum viscosity modified/stabilizer. Several such formulations and the method of their preparation are described.
    Type: Grant
    Filed: September 21, 1995
    Date of Patent: January 28, 1997
    Assignee: FMC Corporation
    Inventors: Fui-Tseng H. Lee, Paul Nicholson
  • Patent number: 5589439
    Abstract: Herbicidal novel tetrazolinone derivatives of the formula: ##STR1## wherein R.sup.1 is alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy or phenyl which is optionally substituted, andR.sup.2 is alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy or phenyl which is optionally substituted, orR.sup.1 and R.sup.2 form, together with the nitrogen atom to which R.sup.1 and R.sup.2 are bonded, a 5- or 6-membered heterocyclic ring, optionally fused to a carbocyclic ring optionally and independently substituted by C.sub.1-4 alkyl, andR.sup.3 is a 5-membered heterocyclic radical containing at least one hereto atom selected from the group consisting of nitrogen, oxygen, and sulfur, optionally substituted by at least one substitutent selected from the group consisting of halogen, benzyl, phenyl, halogen-substituted phenyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylthio, C.sub.1-4 alkyl-sulfonyl and C.sub.
    Type: Grant
    Filed: July 28, 1995
    Date of Patent: December 31, 1996
    Assignee: Nihon Bayer Agrochem K.K.
    Inventors: Toshio Goto, Koichi Moriya, Fritz Maurer, Seishi Ito, Katsuaki Wada, Kazuhiro Ukawa, Ryo Watanabe, Asami Ito, Natsuko Minegishi
  • Patent number: 5583090
    Abstract: There is provided an aqueous dispersion of microcapsules containing the herbicide clomazone dissolved in an inert high boiling organic solvent. Vapor transfer of the herbicide outside the targeted area is controlled without substantial sacrifice of the efficacy of the herbicide.
    Type: Grant
    Filed: June 26, 1995
    Date of Patent: December 10, 1996
    Assignee: Monsanto Company
    Inventors: Alan J. Stern, Alan P. Lundstedt, Salim M. Hakimi, Sudabathula Rao
  • Patent number: 5576270
    Abstract: The invention pertains to isoxazolecarboxamides of the formula I ##STR1## where R.sup.1 is alkyl, cycloalkyl, alkoxyalkyl, alkenyl, alkynyl, phenyl or unsubstituted or substituted benzyl,R.sup.2 is hydrogen or alkyl andR.sup.3 is alkyl, cycloalkyl, alkenyl, alkynyl, phenyl or unsubstituted or substituted benzyl,and the plant-tolerated salts of those compounds in which R.sup.2 is hydrogen, their preparation and their use.
    Type: Grant
    Filed: September 29, 1994
    Date of Patent: November 19, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Maywald, Thomas Kuekenhoehner, Peter Muenster, Wolfgang von Deyn, Helmut Walter, Matthias Gerber, Karl-Otto Westphalen, Uwe Kardorff
  • Patent number: 5573999
    Abstract: .beta.-Substituted cinnamic acid derivatives of the formula 1, ##STR1## where R.sup.1 is alkyl, chlorine or bromine, --X-- is --O--, --S--, ##STR2## m is 0 or 1, --Y is --OR.sup.4, --O--N.dbd.CR.sup.5 R.sup.6, --NR.sup.7 R.sup.8, --N(OR.sup.9)R.sup.10 or --SR.sup.11, where the above-mentioned substituents R.sup.2 to R.sup.11 are alkyl, and R.sup.2, and R.sup.3 and R.sup.5 to R.sup.11 can also be hydrogen,Z is halogen, nitro, cyano, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, arylthioalkyl, hetarylalkyl, hetaryloxyalkyl, hetarylthioalkyl, alkenyl, aralkenyl, aryloxyalkenyl, arylthioalkenyl, hetarylalkenyl, hetaryloxyalkenyl, hetarylthioalkenyl, alkynyl, arylalkynyl, hetarylalkynyl, aryl, hetaryl, arylazo, acylamino, --OR.sup.12, --SR.sup.13, --SOR.sup.14, --SO.sub.2 R.sup.15, --COOR.sup.16, --CONR.sup.17 R.sup.18, --COR.sup.19, --CR.sup.20 .dbd.NR.sup.21, --N.dbd.CR.sup.22, R.sup.23, --CR.sup.24 .dbd.N--OR.sup.25, --CR.sup.25 R.sup.26 --O--, N.dbd.CR.sup.27 R.sup.28, --CH.sub.2 --OCOR.sup.39 or --NR.sup.37 R.
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: November 12, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Hubert Sauter, Herbert Bayer, Klaus Oberdorf, Horst Wingert, Wolfgang von Deyn, Wassilios Grammenos, Hartmann Koenig, Harald Rang, Franz Roehl, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5543416
    Abstract: Cyanoisoxazoles of the formula Ia or Ib ##STR1## where R.sup.1 is hydrogen, alkyl, cycloalkyl, phenyl; R.sup.2 is hydrogen, alkyl, cycloalkyl and R.sup.3 is alkoxy, alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl or phenyl, it being possible for the organic radicals mentioned under R.sup.1, R.sup.2 and R.sup.3 to be substituted in each case. The compounds of the Formula Ia or Ib are useful as herbicides.
    Type: Grant
    Filed: February 22, 1995
    Date of Patent: August 6, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter M unster, Klaus Ditrich, Gerhard Hamprecht, Matthias Gerber, Karl-Otto Westphalen, Helmut Walter, Rudolf Karl
  • Patent number: 5538940
    Abstract: .beta.-Substituted cinnamic acid derivatives of the formula 1, ##STR1## where R.sup.1 is substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, and R.sup.1 can also be chlorine or bromine,--X-- is --O--, --S--, ##STR2## m is 0 or 1, --Y is --OR.sup.4, --O--N.dbd.CR.sup.5 R.sup.6, --NR.sup.7 R.sup.8, --NR.sup.7 R.sup.8, --N(OR.sup.9)R.sup.10 or SR.sup.11, where the abovementioned substitutes R.sup.2 to R.sup.11 are substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, and R.sup.2, R.sup.3 and R.sup.5 to R.sup.11 can be hydrogen and Z, U, V, W are defined in the specification.
    Type: Grant
    Filed: May 12, 1995
    Date of Patent: July 23, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Hubert Sauter, Herbert Bayer, Klaus Oberdorf, Horst Wingert, Wolfgang Von Deyn, Wassilios Grammenos, Hartmann Koenig, Harald Rang, Franz Roehl, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5523278
    Abstract: There are provided substituted benzisoxazole and benzisothiazole compounds having the structural formula I ##STR1## Further provided are compositions and methods comprising those compounds for the control of undesirable plant species.
    Type: Grant
    Filed: September 12, 1995
    Date of Patent: June 4, 1996
    Assignee: American Cyanamid Company
    Inventor: Peter J. Wepplo
  • Patent number: 5521143
    Abstract: Isoxazolines or isothiazolines having the formula (I), or their salts, in which (Z).sub.n, X and R have the definition given in the first claim, are useful as safeners against the phytotoxic side effects of herbicides, preferably in cereal crops.
    Type: Grant
    Filed: January 29, 1993
    Date of Patent: May 28, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz-Josef Loher, Klaus Bauer, Hermann Bieringer
  • Patent number: 5516750
    Abstract: Substituted isoxazolines, process for their preparation, compositions containing them, and their use as safeners.Compounds of the formula (I) and salts thereof, ##STR1## in which R.sup.1 is carboxyl, formyl or another acyl radical or a derivative of the last-mentioned 3 groups,R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.18 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.2 -C.sub.8 -alkynyl, C.sub.1 -C.sub.18 -alkoxy, C.sub.2 -C.sub.8 -alkenyloxy, C.sub.2 -C.sub.8 -alkynyloxy, C.sub.1 -C.sub.18 -alkylthio, C.sub.2 -C.sub.8 -alkenylthio, each of the last-mentioned 9 radicals in each case being unsubstituted or substituted, or (C.sub.1 -C.sub.8 -alkoxy)carbonyl, andR.sup.3 and R.sup.
    Type: Grant
    Filed: September 14, 1994
    Date of Patent: May 14, 1996
    Assignee: Hoechst Schering AgrEvo GmbH
    Inventors: Lothar Willms, Klaus Bauer, Hermann Bieringer
  • Patent number: 5496792
    Abstract: Cyclohexenone oxime ethers I ##STR1## R.sup.1 =C.sub.1 -C.sub.6 -alkyl; W=unsubstituted or C.sub.1 -C.sub.3 -alkyl-substituted C.sub.2 -C.sub.4 -alkylene chain;X=NO.sub.2, CN, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl; n=0-3 or 1-5 if all X's are halogen;R.sup.2 =C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, substituted or unsubstituted C.sub.3 -C.sub.7 -cycloalkyl, substituted or unsubstituted C.sub.5 -C.sub.7 -cycloalkenyl, a substituted or unsubstituted 5-membered saturated heterocycle containing 1 or 2 oxygen and/or sulfur atoms, substituted or unsubstituted 6- or 7-membered heterocycle having 1 or 2 non-adjacent oxygen and/or sulfur atoms and which is saturated or mono- or diunsaturated, substituted or unsubstituted 5-membered heteroaromatic containing 1 or 2N atoms and one O or S atom, phenyl or pyridyl, both of which are unsubstituted or bear 1-3 halogen, NO.sub.
    Type: Grant
    Filed: August 11, 1994
    Date of Patent: March 5, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Kaspar Bott, Helmut Walter, Karl-Otto Westphalen, Uwe Kardorff, Matthias Gerber
  • Patent number: 5489562
    Abstract: A herbicidal composition having acivicin, its derivatives or salts or combinations thereof as its active component.A process for controlling unwanted plants comprising applying a herbicidally effective amount of acivicin, its derivatives or salts or combinations thereof to the unwanted plant.
    Type: Grant
    Filed: July 13, 1994
    Date of Patent: February 6, 1996
    Assignee: Rohm and Haas Company
    Inventors: Ernest L. Burdge, Lori A. Spangler
  • Patent number: 5489570
    Abstract: The invention relates to isoxazole derivatives of formula (I): ##STR1## wherein: Ar represents phenyl optionally substituted by from one to three groups and wherein two substituents on adjacent positions of the phenyl ring, together with the two atoms to which they are attached, form a 5- to 7-membered ring which is optionally substituted;R represents the hydrogen atom or a group --CO.sub.2 R.sup.3 ;R.sup.1 represents alkyl, haloalkyl or optionally substituted cycloalkyl;R.sup.3 represents alkyl, alkenyl or alkynyl containing up to six carbon atoms which is optionally substituted by one or more halogen atoms;and their use as herbicides.
    Type: Grant
    Filed: July 29, 1994
    Date of Patent: February 6, 1996
    Assignee: Rhone-Poulenc Agriculture Limited
    Inventors: Neil Geach, David W. Hawkins, Christopher J. Pearson, Philip H. G. Smith, Nicolas White
  • 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: 5407901
    Abstract: This patent application relates to Certain tricyclic ether herbicidal compounds and their use to control a broad spectrum of undesirable plant growth.
    Type: Grant
    Filed: November 16, 1993
    Date of Patent: April 18, 1995
    Assignee: E. I. Du Pont de Nemours
    Inventor: Eric de G. Taylor
  • Patent number: 5399544
    Abstract: Isoxazole- and isothiazole-5-carboxamides of the formula ##STR1## where X is oxygen or sulfur, R.sup.1 is hydrogen, substituted or unsubstituted alkyl, cycloalkyl, cycloalkenyl, alkenyl (may be epoxidized at the double bond), alkynyl, alkoxy, a heterocyclic radical or phenyl, R.sup.2 is a derivative carboxylic acid function and R.sup.3 and R.sup.4 have the meanings given in the disclosure, and herbicidal agents containing compounds I.
    Type: Grant
    Filed: September 14, 1993
    Date of Patent: March 21, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Maywald, Peter Muenster, Hartmann Koenig, Gerhard Hamprecht, Thomas Kuekenhoehner, Wolfgang Rohr, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
  • Patent number: 5389602
    Abstract: Tetrahydropyran-2,4-diones of the formula ##STR1## where R.sup.1 is hydrogen; C.sub.1 -C.sub.6 -alkyl; C.sub.2 -C.sub.6 -alkenyl; C.sub.2 -C.sub.6 -alkynyl; substituted or unsubstituted phenyl; C.sub.1 -C.sub.6 -alkylsulfonyl; substituted or unsubstituted benzenesulfonyl; C.sub.3 -C.sub.6 -alkenylcarbonyl; or substituted or unsubstituted benzoyl;R.sup.2 is C.sub.1 -C.sub.6 -alkyl; C.sub.2 -C.sub.6 -alkenyl; C.sub.2 -C.sub.6 -alkynyl; C.sub.1 -C.sub.6 -haloalkyl; or C.sub.3 -C.sub.6 -cycloalkyl;A, B and D are each .dbd.CH-- or .dbd.N--;E is oxygen, sulfur or --NR.sup.7 --.R.sup.7 is hydrogen; C.sub.1 -C.sub.6 -alkyl; C.sub.2 -C.sub.6 -alkenyl; C.sub.2 -C.sub.6 -alkanoyl; substituted or unsubstituted benzoyl; benzyl; or substituted or unsubstituted phenyl;X is halogen; C.sub.1 -C.sub.6 -alkyl; substituted or unsubstituted C.sub.3 -C.sub.6 -cycloalkyl; C.sub.2 -C.sub.6 -alkenyl; C.sub.2 -C.sub.6 -alkynyl; C.sub.1 -C.sub.6 -alkoxy; C.sub.2 -C.sub.6 -alkenyloxy; C.sub.1 -C.sub.6 -alkylthio; C.sub.1 -C.sub.
    Type: Grant
    Filed: June 15, 1993
    Date of Patent: February 14, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Kast, Dieter Kolassa, Norbert Meyer, Bruno Wuerzer, Karl-Otto Westphalen, Wilhelm Rademacher, Johann Jung