Abstract: The present invention relates to herbicidally, acaricidally and insecticidally active pyrazolidine-3,5-diones of the formula I ##STR1## in which R.sub.1 is ##STR2## R.sub.2 and R.sub.3 independently of one another are C.sub.1 -C.sub.6 alkyl; C.sub.3 -C.sub.6 alkenyl; or C.sub.3 -C.sub.6 alkynyl; orR.sub.2 and R.sub.3 together are a --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --CH.sub.2 --CH.dbd.CH--CH.sub.2 --, --CH.sub.2 --CH.dbd.CH-- or --(CH.sub.2).sub.2 --CH.dbd.CH-- bridge which is unsubstituted or up to trisubstituted by C.sub.1 -C.sub.4 alkyl;n is 0; 1; 2; 3; or 4;m is 0; or 1; the total of m and n being less than, or equal to, 4; theR.sub.4 radicals independently of one another are halogen; nitro; cyano, C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.10 alkoxy; C.sub.1 -C.sub.4 haloalkoxy; C.sub.3 -C.sub.6 alkenyloxy; C.sub.1 -C.sub.4 alkoxy-C.sub.2 -.sub.4 alkoxy; C.sub.3 -C.sub.6 alkynyloxy; C.sub.1 -C.sub.4 alkylcarbonyl; C.sub.1 -C.sub.4 alkoxycarbonyl; C.sub.1 -C.sub.
Type:
Grant
Filed:
September 17, 1993
Date of Patent:
April 9, 1996
Assignee:
Ciba-Geigy Corporation
Inventors:
Frederik Cederbaum, Hans-Georg Brunner, Manfred Boger
Abstract: The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R.sup.1 -Z.sup.1 in which Z.sup.1 is a leaving group, or with an aldehyde produces compounds of formula I ##STR1## wherein R.sup.1 is --OH, --SH, --CHO, --CN, --COOH, --B(OH).sub.2, --COX, with X being Cl or Br, or is --COOR.sup.2, --SIR.sup.2.sub.3 or --B(OR.sup.2).sub.2, with R.sup.2 being a C.sub.1 -C.sub.12 alcohol moiety without the hydroxy group, wherein R.sup.1 is further --C.sub.n H.sub.2n COOR.sup.2, with n being an integer from 1 to 4, or linear or branched C.sub.1 -C.sub.12 hydroxyalkyl which is unsubstituted or is substituted by --F, --CN, C.sub.1 -C.sub.6 alkoxy, phenyl, fluorophenyl, C.sub.1 -C.sub.4 alkoxy-phenyl, C.sub.1 -C.sub.4 alkylthio-phenyl, C.sub.1 -C.sub.4 alkyl-phenyl, C.sub.1 -C.sub.4 fluoroalkyl-phenyl, nitrophenyl or by cyanophenyl, or wherein R.sup.1 is a benzyl alcohol which is unsubstituted or is substituted by F, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.
Type:
Grant
Filed:
May 12, 1995
Date of Patent:
March 5, 1996
Assignee:
Ciba-Geigy Corporation
Inventors:
Peter Ackermann, Hans-Ruedi Ka/ nel, Bruno Schaub
Abstract: The present invention relates to herbicidally, acaricidally and insecticidally active pyrazolidine-3,5-diones of the formula I ##STR1## in which R.sub.1 is ##STR2## R.sub.2 and R.sub.3 independently of one another are C.sub.1 -C.sub.6 alkyl; C.sub.3 -C.sub.6 alkenyl; or C.sub.3 -C.sub.6 alkynyl; orR.sub.2 and R.sub.3 together are a --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --CH.sub.2 --CH.dbd.CH--CH.sub.2 --, --CH.sub.2 --CH.dbd.CH-- or --(CH.sub.2).sub.2 --CH.dbd.CH-- bridge which is unsubstituted or up to trisubstituted by C.sub.1 -C.sub.4 alkyl;n is 0; 1; 2; 3; or 4;m is 0; or 1; the total of m and n being less than, or equal to, 4; theR.sub.4 radicals independently of one another are halogen; nitro; cyano, C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.10 alkoxy; C.sub.1 -C.sub.4 haloalkoxy; C.sub.3 -C.sub.6 alkenyloxy; C.sub.1 -C.sub.4 alkoxy-C.sub.2 -C.sub.4 alkoxy; C.sub.3 -C.sub.6 alkynyloxy; C.sub.1 -C.sub.4 alkylcarbonyl; C.sub.1 -C.sub.4 alkoxycarbonyl; C.sub.1 -C.sub.
Type:
Grant
Filed:
June 2, 1995
Date of Patent:
February 27, 1996
Assignee:
Ciba-Geigy Corporation
Inventors:
Frederik Cederbaum, Hans-Georg Brunner, Manfred Boger
Abstract: Thiadiazabicyclooctanes and thiadiazabicyclooctenes of formula I ##STR1## wherein the substituents are as defined herein, having good pre- and post-emergence selective herbicidal properties.
Type:
Grant
Filed:
December 2, 1993
Date of Patent:
February 27, 1996
Assignee:
Ciba-Geigy Corporation
Inventors:
Hans-Georg Brunner, Hans Moser, Georg Pissiotas
Abstract: The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R.sup.1 -Z.sup.1 in which Z.sup.
Type:
Grant
Filed:
March 6, 1995
Date of Patent:
February 20, 1996
Assignee:
Ciba-Geigy Corporation
Inventors:
Peter Ackermann, Hans-Ruedi Kanel, Bruno Schaub
Abstract: A process for the preparation of an aqueous medium of nicotinaldehyde by the catalytic reduction of 3-cyanopyridine under hydrogen in the presence of Raney-nickel.
Abstract: Pyrimidinyloxy- and triazinyloxy- and pyrimidinylthio- and triazinylthio-butyric acid derivatives of formula I ##STR1## wherein Q is ##STR2## A is hydroxy or a group ##STR3## and the other substituents are as described in patent claim 1, and salts of compounds of formula I, have herbicidal action and are suitable as active ingredients in weed control compositions.
Abstract: Compounds of the formula ##STR1## in which A is oxygen, sulfur or --NR.sub.1 --;B is C.sub.2 -C.sub.6 alkylene,D-E is --O--E, --S--E, --O--CH.sub.2 --E, --O--C(.dbd.O)--E, --O--C(.dbd.O)--O--E, --O--C(.dbd.O)--N(H)--E or --O--C(.dbd.S)--N(H)--E;E is phenyl; phenyl which is substituted by one to three substituents; a five-membered aromatic heterocycle having one to three hetero atoms; a five-membered aromatic heterocycle which has one to three hetero atoms and which is substituted by one or two substituents; a six-membered aromatic heterocycle which has one to three nitrogen atoms; or a six-membered aromatic heterocycle which has one to three nitrogen atoms and which is substituted by one or two substituents;L is halogen or methyl;X is fluorine;Y is chlorine or fluorine;Z is hydrogen, fluorine or methyl;m is the number zero, one, two, three, four or five;n is the number zero, one or two andR.sub.1 is hydrogen, C.sub.1 -C.sub.
Type:
Grant
Filed:
June 23, 1993
Date of Patent:
January 2, 1996
Assignee:
Ciba-Geigy Corporation
Inventors:
Peter Maienfisch, Thomas Pitterna, Manfred Boger
Abstract: The novel 2R,4S-2-ethyl-4-[(4-phenoxyphenoxy)methyl]dioxolan of formula I ##STR1## can be used as a pesticide. It is used to control especially insects in fruit and citrus crops.
Type:
Grant
Filed:
September 29, 1994
Date of Patent:
December 26, 1995
Assignee:
Ciba-Geigy Corporation
Inventors:
Friedrich Karrer, Hans-Peter Buser, Gerardo Ramos, Alfred Rindlisbacher, Luigi M. Venanzi, Thomas R. Ward
Abstract: Compounds of formula I ##STR1## where R.sub.1 -R.sub.5, R.sub.8, R.sub.13, m and n are as defined herein. The novel compounds have valuable biocidal properties. They can be used in crop protection for protecting cultivated plants against attack by pests, and for controlling those pests.
Type:
Grant
Filed:
September 23, 1993
Date of Patent:
November 21, 1995
Assignee:
Ciba-Geigy Corporation
Inventors:
Odd Kristiansen, Helmut Zondler, Urs Muller
Abstract: The invention relates to a process for the preparation of a compound of formula ##STR1## useful as intermediate for the preparation of pesticides, wherein R is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkyl substituted by from 1 to 10 halogen atoms or by from 1 to 3 radicals selected from the group consisting of C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio and phenyl, phenyl or phenyl substituted by from 1 to 3 radicals selected from the group consisting of halogen, methyl, ethyl, methoxy, methylthio and nitro, which comprises reacting with hydrazine hydrate a compound of formula ##STR2## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkyl substituted by from 1 to 9 chlorine atoms, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfonyl, C.sub.1 -C.sub.
Abstract: Compounds of the formula ##STR1## wherein the variables R.sub.1 and p and the rings A and B are as defined in claim 1, and, where appropriate, tautomers thereof, in each case in free form or in the form of a salt, can be used as agrochemical active ingredients and can be prepared in a manner known per se.
Abstract: Compounds of the formula ##STR1## wherein A is a substituted or unsubstituted, aromatic or non-aromatic, monocyclic or bicyclic, heterocyclic radical that is bonded by way of a carbon atom to X; each of R.sub.1 and R.sub.2, independently of the other, is hydrogen or C.sub.1 -C.sub.6 alkyl; X is NR.sub.3, O or S; and R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl, 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:
October 30, 1992
Date of Patent:
August 8, 1995
Assignee:
Ciba-Geigy Corporation
Inventors:
Peter Maienfisch, Manfred Boger, Thomas Pitterna
Abstract: A process for the preparation of 2-alkyl-6-methyl-N(1'-methoxy-2'-propyl)-aniline by catalytic reductive alkylation wherein at least one mole equivalent of methoxyacetone is reacted with one mole equivalent of 2-alkyl-6-methyl-aniline in a liquid medium without an additional solvent, in the presence of a platinized carbon catalyst and hydrogen and in the presence of an acid cocatalyst under a hydrogen pressure of between 2.times.10.sup.5 and 1.times.10.sup.6 Pa at a temperature between 20.degree. and 80.degree. C., characterized in that the reaction mixture contains water from the beginning of the reaction and after the hydrogenation, base is added, the reaction mixture is filtered to separate the catalyst and the title compound recovered from the filtrate. The process is particularly useful for the preparation of N-substituted chloracetanilide herbicides.
Type:
Grant
Filed:
December 15, 1993
Date of Patent:
July 4, 1995
Assignee:
Ciba-Geigy Corporation
Inventors:
Rolf Bader, Peter Flatt, Paul Radimerski
Abstract: The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R.sup.1 -Z.sup.1 in which Z.sup.1 is a leaving group, or with an aldehyde produces compounds of formula I ##STR1## wherein R.sup.1 is --OH, --SH, --CHO, --CN, --COOH, --B(OH).sub.2, --COX, with X being Cl or Br, or is --COOR.sup.2, --SiR.sub.3.sup.2 or --B(OR.sup.2).sub.2, with R.sup.2 being a C.sub.1 -C.sub.12 alcohol moiety without the hydroxy group, wherein R.sup.1 is further --C.sub.n H.sub.2n COOR.sup.2, with n being an integer from 1 to 4, or linear or branched C.sub.1 -C.sub.12 hydroxyalkyl which is unsubstituted or is substituted by --F, --CN, C.sub.1 -C.sub.6 alkoxy, phenyl, fluorophenyl, C.sub.1 -C.sub.4 alkoxy-phenyl, C.sub.1 -C.sub.4 alkylthio-phenyl, C.sub.1 -C.sub.4 alkyl-phenyl, C.sub.1 -C.sub.4 fluoroalkyl-phenyl, nitrophenyl or by cyanophenyl, or wherein R.sup.1 is a benzyl alcohol which is unsubstituted or is substituted by F, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.
Type:
Grant
Filed:
November 5, 1993
Date of Patent:
May 30, 1995
Assignee:
Ciba-Geigy Corporation
Inventors:
Peter Ackermann, Hans-Ruedi Kanel, Bruno Schaub
Abstract: Thiadiazabicyclooctanes of formula I ##STR1## wherein Z is oxygen or sulfur;R.sub.53 is hydrogen or C.sub.1 -C.sub.6 alkyl;R.sub.54 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 alkenyloxy, C3-C6alkynyioxy, hydroxy or C.sub.1 -C.sub.6 haloalkoxy; orR.sub.53 and R.sub.54, together with the carbon atom to which they are bonded, form an unsubstituted 3-, 4-, 5- or 6-membered saturated ring;W is a group of formulae W.sub.1 to W.sub.
Type:
Grant
Filed:
November 18, 1993
Date of Patent:
May 16, 1995
Assignee:
Ciba-Geigy Corporation
Inventors:
Hans-Georg Brunner, Hans Moser, Georg Pissiotas
Abstract: The invention provides a process for fixing dyes on organic material, which comprises fixing dyes containing at least one polymerizable double bond or at least one polymerizable ring system, in the presence of at least one colorless binder which contains at least one polymerizable double bond, and at least one photosensitizer, as well as further optional auxiliaries, by subjecting said material to irradiation with UV light. The invention also provides a dyeing formulation which enables the dyeing to be fixed by the inventive process.