Patents by Inventor Josef Ehrenfreund

Josef Ehrenfreund has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 6034083
    Abstract: Compounds of formula ##STR1## wherein n and Z are as defined in claim 1, and, where appropriate, tautomers thereof, in each case in free form or in salt form, can be used as agrochemical active ingredients and can be prepared in a manner known per se.
    Type: Grant
    Filed: July 20, 1998
    Date of Patent: March 7, 2000
    Assignee: Novartis Corp.
    Inventors: Henry Szczepanski, Haukur Kristinsson, Peter Maienfisch, Josef Ehrenfreund
  • Patent number: 5783704
    Abstract: Compounds of formu (I) wherein n and Z are as defined in claim 1, and, where appropriate, tautomers thereof, in each case in free form, or in salt form, can be used as agrochemical active ingredients and can be prepared in a manner known per se.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: July 21, 1998
    Assignee: Novartis Corporation
    Inventors: Henry Szczepanski, Haukur Kristinsson, Peter Maienfisch, Josef Ehrenfreund
  • Patent number: 5457095
    Abstract: The compounds of the formula ##STR1## in which one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen, C.sub.1-8 -alkyl, C.sub.3-6 -cycloalkyl, phenyl optionally substituted by halogeno, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy and/or trifluoromethyl, or C.sub.7-10 -phenylalkyl optionally substituted in the phenyl moiety by halogeno, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy and/or trifluormethyl, and the other two are hydrogen, or salts thereof.These compounds have valuable pharmaceutical properties.
    Type: Grant
    Filed: June 7, 1994
    Date of Patent: October 10, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: John G. Dingwall, Josef Ehrenfreund, Roger G. Hall, James Jack
  • Patent number: 5243062
    Abstract: The compounds of the formula ##STR1## in which one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen, C.sub.1 -.sub.8 -alkyl, C.sub.3 -.sub.6 -cycloalkyl, phenyl optionally substituted by halogeno, C.sub.1 -.sub.4 -alkyl, C.sub.1 -.sub.4 -alkoxy and/or trifluoromethyl, or C.sub.7 -.sub.10 -phenylalkyl optionally substituted in the phenyl moiety by halogeno, C.sub.1 -.sub.4 -alkyl, C.sub.1 -.sub.4 -alkoxy and/or trifluormethyl, and the other two are hydrogen, or salts thereof.These compounds have valuable pharmaceutical properties.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: September 7, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: John Gray Dingwall, Josef Ehrenfreund, Roger Graham Hall, James Jack
  • Patent number: 5210100
    Abstract: The invention relates to novel N-[3-halo-4-(hexafluoropropoxy)-5-trifluoromethyl]phenyl-N'-benzoylureas of the formula ##STR1## wherein R.sub.1 is hydrogen or halogen and R.sub.2 and R.sub.3 are halogen, to a process and intermediate for the preparation of these compounds, and to compositions containing them for use in pest control, in particular for controlling insects and representatives of the order Acarina that attack plants and animals. The novel compounds exhibit in particular larvicidal activity.
    Type: Grant
    Filed: October 25, 1989
    Date of Patent: May 11, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Josef Ehrenfreund
  • Patent number: 5196563
    Abstract: Novel N-phenyl-N-carboxythioureas of the formula I ##STR1## in which R.sub.1 and R.sub.2 each represents C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.7 cycloalkyl or C.sub.5 -C.sub.6 cycloalkenyl,R.sub.3 represents hydrogen, halogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy or C.sub.1 -C.sub.10 alkylthio,R.sub.4 represents C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl or phenyl-C.sub.1-C.sub.7 alkyl; C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl or phenyl-C.sub.1 -C.sub.7 alkyl each mono- or poly-substituted by halogen or interrupted one or several times by oxygen and/or sulphur; C.sub.3 -C.sub.8 cycloalkyl; or C.sub.3 -C.sub.8 cycloalkyl mono- or poly-substituted by halogen or by C.sub.1 -C.sub.5 alkyl, andR.sub.5 represents C.sub.1 -C.sub.10 alkyl; phenyl-C.sub.1 -C.sub.7 alkyl; C.sub.1 -C.sub.10 alkyl or phenyl-C.sub.1 -C.sub.7 alkyl each mono- or poly-substituted by halogen or interrupted one or several times by oxygen and/or sulphur; C.
    Type: Grant
    Filed: November 14, 1989
    Date of Patent: March 23, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Jozef Drabek, Josef Ehrenfreund
  • Patent number: 5187197
    Abstract: Novel substituted phenyl-thioureas, -isothioureas and -carbodiimides of formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkyl mono- or poly-substituted by halogen and/or by C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyl mono- or poly-substituted by C.sub.1 -C.sub.3 alkyl, or is C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 C.sub.4 alkyl; each of R.sub.2 and R.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkenyl; each of R.sub.4 and R.sub.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; each R.sub.6 is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 C.sub.4 haloalkoxy or a --CH.dbd.CH, --CH.sub.2 or --CH.sub.2 bridge in the 2,3-or 3,4-position; n is 0, 1 or 2; Z is --NH--CS--NH--, --N.dbd.C(SR.sub.7) --NH--or --N.dbd.C.dbd.N--, and R.sub.7 is C.sub.1 -C.sub.10 alkyl or C.sub.3 -C.sub.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: February 16, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Josef Ehrenfreund
  • Patent number: 5138068
    Abstract: Novel 1-phenyl-5-oxo-2-tetrazolines of formula I ##STR1## in which R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.1 -C.sub.4 alkyl- or halo-substituted C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkyl- or halo-substituted C.sub.5 -C.sub.6 cycloalkenyl, halo-, C.sub.1 -C.sub.4 alkoxy- or phenyl-substituted C.sub.3 -C.sub.6 alkenyl, halo-, C.sub.1 -C.sub.4 alkoxy- or phenyl-substituted C.sub.3 -C.sub.8 alkynyl, or C.sub.1 -C.sub.8 alkyl that is substituted by halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl, cyano, hydroxy, halophenyl, C.sub.1 -C.sub.4 alkylphenyl or by a heteroaromatic radical,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.3 -C.sub.6 cycloalkyl, cyclopentenyl or cyclohexenyl, or is C.sub.1 -C.sub.6 alkyl that is substituted by halogen, by C.sub.1 -C.sub.
    Type: Grant
    Filed: May 22, 1991
    Date of Patent: August 11, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Josef Ehrenfreund, Erich Stamm
  • Patent number: 5114975
    Abstract: The invention relates to novel substituted aryloxyphenylthioureas, aryloxyphenylisothioureas and aryloxyphenylcarobodiimides of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.12 alkyl, unsubstituted or substituted by one or more halogen atoms and/or C.sub.1 -C.sub.6 alkoxy groups; C.sub.3 -C.sub.8 cycloalkyl, unsubstituted or substituted by one or more C.sub.1 -C.sub.3 alkyl groups; or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl,R.sub.2 and R.sub.3 are each C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen, methyl or --CHO,R.sub.5 is halogen; C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by one or more halogen atoms; C.sub.1 -C.sub.4 alkoxy, unsubstituted or substituted by one or more halogen atoms; or is a --CH.dbd.CH).sub.2, --CH.sub.2).sub.3 or --CH.sub.2).sub.4 bridge in 2,3- or 3,4-position,n is 0, 1, 2, 3 or 4,Z is --NH--CS--NH--, --N.dbd.C(SR.sub.6)--NH-- or --N.dbd.C.dbd.N--; andR.sub.6 is C.sub.1 -C.sub.
    Type: Grant
    Filed: April 3, 1991
    Date of Patent: May 19, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Manfred Boger, Jozef Drabek, Josef Ehrenfreund
  • Patent number: 5077412
    Abstract: The invention relates to novel substituted phenylthioureas, phenylisothioureas and phenylcarbodiimides of formula I ##STR1## wherein Z is ##STR2## or --N.dbd.C.dbd.N--; R.sub.1 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.3 alkyl substituted by 1 or 2 C.sub.3 -C.sub.6 cycloalkyl radicals, or is alkoxyalkyl containing a total of 3 to 10 carbon atoms, halogen-substituted C.sub.1 -C.sub.12 alkyl, polycyclic C.sub.7 -C.sub.10 cycloalkyl, or phenyl(C.sub.1 -C.sub.5)alkyl which may be substituted in the phenyl moiety by 1 or 2 identical or different members selected from the group consisting of halogen, methoxy, ethoxy and C.sub.1 -C.sub.5 alkyl,R.sub.2 is hydrogen or C.sub.1 -C.sub.5 alkyl,R.sub.3 is C.sub.1 -C.sub.5 alkyl or C.sub.3 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sub.
    Type: Grant
    Filed: September 29, 1989
    Date of Patent: December 31, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Josef Ehrenfreund, Manfred Boger, Odd Kristiansen, Jozef Drabek, Haukur Kristinsson
  • Patent number: 5066667
    Abstract: Novel 1-phenyl-5-thioxo-2-tetrazolines of formula I ##STR1## in which R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 -cycloalkenyl, C.sub.1 -C.sub.4 alkyl- or halo-substituted C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 -alkyl- or halo-substituted C.sub.5 -C.sub.6 cycloalkenyl, halo-, C.sub.1 -C.sub.4 alkoxy- or phenyl-substituted C.sub.3 -C.sub.6 alkenyl, halo-, C.sub.1 -C.sub.4 alkoxy- or phenyl-substituted C.sub.3 -C.sub.8 alkynly, or C.sub.1 -C.sub.8 alkyl that is substituted by halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl, cyano, hydroxy, halophenyl, C.sub.1 -C.sub.4 alkylphenyl or by a heteroaromatic radical.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.3 -C.sub.6 cycloalkyl, cyclopentenyl or cyclohexenyl, or is C.sub.1 -C.sub.6 alkyl that is substituted by halogen, by C.sub.1 -C.sub.
    Type: Grant
    Filed: June 18, 1990
    Date of Patent: November 19, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Josef Ehrenfreund, Erich Stamm
  • Patent number: 5026730
    Abstract: The invention relates to novel substituted anilinophenylthioureas, anilinophenylisothioureas and anilinophenylcarbodiimides of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.12 alkyl, unsubstituted or substituted by one or more halogen atoms and/or C.sub.1 -C.sub.6 alkoxy groups; C.sub.3 -C.sub.8 cycloalkyl, unsubstituted or substituted by one or more C.sub.1 -C.sub.3 alkyl groups; or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl,R.sub.2 and R.sub.3 are each C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen, methyl or --CHO,R.sub.5 is halogen; C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by one or more halogen atoms; C.sub.1 -C.sub.4 alkoxy, unsubstituted or substituted by one or more halogen atoms; or is a --CH.dbd.CH--.sub.2, --CH.sub.2--3 or --CH.sub.2--4 bridge in 2,3- or 3,4-position,n is 0, 1, 2, 3 or 4,Z is --NH--CS--NH--, --N.dbd.C(SR.sub.6)--NH-- or --N.dbd.C.dbd.N--; andR.sub.6 is C.sub.1 -C.sub.
    Type: Grant
    Filed: August 11, 1988
    Date of Patent: June 25, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Manfred Boger, Jozef Drabek, Josef Ehrenfreund
  • Patent number: 5004826
    Abstract: The compounds of the formula ##STR1## in which one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen, C.sub.1-8 -alkyl, C.sub.3-6 -cycloalkyl, phenyl optionally substituted by halogeno, C.sub. 1-4 -alkyl, C.sub. -4 -alkoxy and/or trifluoromethyl, or C.sub.7-10 -phenylalkyl optionally substituted in the phenyl moiety by halogeno, C.sub.1-4 -alkyl C.sub.1-4 -alkoxy and/or trifluormethyl, and the other two are hydrogen, or salts thereof.These compounds have valuable pharmaceutical properties.
    Type: Grant
    Filed: December 1, 1989
    Date of Patent: April 2, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: John G. Dingwall, Josef Ehrenfreund, Roger G. Hall, James Jack
  • Patent number: 4971994
    Abstract: Novel N-phenyl-N-carbonylthioureas of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.10 alkyl, phenyl-C.sub.1 -C.sub.7 alkyl; C.sub.1 -C.sub.10 alkyl or phenyl-C.sub.1 -C.sub.7 alkyl each of which is monohalogenated or polyhalogenated or interrupted once or more than once by oxygen and/or sulfur; C.sub.3 -C.sub.8 cycloalkyl; C hd 3-C.sub.8 cycloalkyl which is monosubstituted or polysubstituted by halogen or C.sub.1 -C.sub.5 alkyl; or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl,R.sub.2 is C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, phenyl, phenyl-C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.8 cycloalkyl; C.sub.1 14 C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl or phenyl-C.sub.1 -C.sub.7 alkyl each of which is monohalogenated or polyhalogenated or interrupted once or more than once by oxygen and/or sulfur; C.sub.3 -C.sub.8 cycloalkyl; phenyl or C.sub.3 -C.sub.8 cycloalkyl each of which is monosubstituted or polysubstituted by halogen or C.
    Type: Grant
    Filed: April 11, 1989
    Date of Patent: November 20, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Jozef Drabek, Manfred Boger, Josef Ehrenfreund
  • Patent number: 4968720
    Abstract: Novel substituted phenyl-thioureas, -isothioureas and -carbodiimides of formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkyl mono- or poly-substituted by halogen and/or by C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyl mono- or poly-substituted by C.sub.1 -C.sub.3 alkyl, or is C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl; each of R.sub.2 and R.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkenyl; each of R.sub.4 and R.sub.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; each R.sub.6 is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy or a --CH.dbd.CH.sub.2, --CH.sub.2 or --CH.sub.2 bridge in the 2,3- or 3,4-position; n is 0, 1 or 2; Z is --NH--CS--NH--, --N.dbd.C(SR.sub.7 --NH-- or --N.dbd.C.dbd.N--, and R.sub.7 is C.sub.1 -C.sub.10 alkyl or C.sub.3 -C.sub.
    Type: Grant
    Filed: August 12, 1988
    Date of Patent: November 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Josef Ehrenfreund
  • Patent number: 4965389
    Abstract: The invention relates to novel phenoxyphenylthioureas, phenoxyphenylisothioureas and phenoxyphenylcarbodiimides of formula I ##STR1## wherein R.sub.1 is C.sub.3 -C.sub.7 cycloalkyl or C.sub.5 -C.sub.6 cycloalkenyl,R.sub.2 is C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyenyl,R.sub.3 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 cycloalkyl, 1-cyclopropylethyl or C.sub.3 -C.sub.5 alkenyl,R.sub.4 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy or CF.sub.3,n is an integer from 1 to 3,Z is --NH--CS--NH--, --N.dbd.C(SR.sub.5)--NH-- or --N.dbd.C.dbd.N--, andR.sub.5 is C.sub.1 -C.sub.5 alkyl or allyl,and to salts thereof, to the preparation of these compounds and to intermediates for their synthesis. The invention further relates to the use of the novel compounds in pest control and to pesticidal compositions which contain at least one compound of formula I. The preferred utility is the control of pests of animals and plants.
    Type: Grant
    Filed: March 1, 1988
    Date of Patent: October 23, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Josef Ehrenfreund
  • Patent number: 4963550
    Abstract: The invention relates to novel substituted N-phenylthioureas, N-phenylisothioureas and N-phenylcarbodiimides of formula ##STR1## wherein R.sub.1 to R.sub.5 and Z are as defined in the specification.The invention further relates to the preparation of said compounds and to compositions containing them for use in pest control, especially for controlling insects and representatives of the order Acarina that are pests of plants and animals, in particular plant-destructive sucking and eating pests.
    Type: Grant
    Filed: February 7, 1990
    Date of Patent: October 16, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Manfred Boger, Jozef Drabek, Josef Ehrenfreund, Odd Kristiansen
  • Patent number: 4952599
    Abstract: Novel substituted phenylthioureas, phenylisothioureas and phenylcarbodiimides of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.10 alkyl, unsubstituted or substituted by one or more halogen atoms and/or C.sub.1 -C.sub.6 alkoxy groups; C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyl which is substituted by one or more halogen atoms and/or C.sub.1 -C.sub.4 alkyl groups; C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl, di(C.sub.3 -C.sub.8)cycloalkyl-C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 phenylalkyl or C.sub.1 -C.sub.4 phenylalkyl which is substituted in the phenyl nucleus by one or more members selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and/or C.sub.1 -C.sub.4 haloalkyl; or is C.sub.5 -C.sub.6 cycloalkenyl,R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkenyl,R.sub.3 is C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen or C.sub.1 -C.sub.3 alkyl,R.sub.
    Type: Grant
    Filed: July 20, 1988
    Date of Patent: August 28, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Josef Ehrenfreund, Manfred Boger, Jozef Drabek
  • Patent number: 4914098
    Abstract: Substituted N-phenylthioureas, N-phenylisothioureas and N-phenylcarbodiimides of formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 cycloalkyl, polycyclic alkyl containing a total of 7 to 10 carbon atoms, C.sub.1 -C.sub.12 alkyl which is substituted by 1 to 12 halogen atoms, C.sub.1 -C.sub.4 alkyl which is substituted by one or two C.sub.3 -C.sub.6 cycloalkyl radicals, alkoxyalkyl containing a total of 3 to 10 carbon atoms, C.sub.1 -C.sub.5 alkyl which is substituted by a phenyl radical, C.sub.1 -C.sub.5 alkyl which is substituted by a phenyl radical which is in turn substituted by one or two members selected from the group consisting of halogen, methyl, methoxy and ethoxy; or is C.sub.3 -C.sub.10 -alkenyl or C.sub.3 -C.sub.10 alkynyl, R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.3 is C.sub.1 -C.sub.4 alkyl, R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl, and R.sub.
    Type: Grant
    Filed: August 12, 1987
    Date of Patent: April 3, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Manfred Boger, Jozef Drabek, Josef Ehrenfreund, Odd Kristiansen
  • Patent number: 4908383
    Abstract: Novel N-phenyl-N-carboxythioureas of the formula I ##STR1## in which R.sub.1 and R.sub.2 each represents C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.7 cycloalkyl or C.sub.5 -C.sub.6 cycloalkenyl,R.sub.3 represents hydrogen, halogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy or C.sub.1 -C.sub.10 alkylthio,R.sub.4 represents C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl or phenyl-C.sub.1 -C.sub.7 alkyl; C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl or phenyl-C.sub.1 -C.sub.7 alkyl each mono- or poly-substituted by halogen or interrupted one or several times by oxygen and/or sulphur; C.sub.3 -C.sub.8 cycloalkyl; or C.sub.3 -C.sub.8 cycloalkyl mono- or poly-substituted by halogen or by C.sub.1 -C.sub.5 alkyl, andR.sub.5 represents C.sub.1 -C.sub.10 alkyl; phenyl-C.sub.1 -C.sub.7 alkyl; C.sub.1 -C.sub.10 alkyl or phenyl-C.sub.1 -C.sub.7 alkyl each mono- or poly-substituted by halogen or interrupted one or several times by oxygen and/or sulphur; C.
    Type: Grant
    Filed: May 23, 1989
    Date of Patent: March 13, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Jozef Drabek, Josef Ehrenfreund