Ciba-geigy Corporation

Dieter Durr

Henry Szczepanski

Ludwig Maier

Otto Rohr

Beat Bohner

Hermann Rempfler

Georg Pissiotas

Hans-Georg Brunner

Jozef Drabek

Willy Meyer

Manfred Boger

Rolf Schurter

Odd Kristiansen

Werner Topfl

Ernst Beriger

Rudolph C Thummel

Hans-Dieter Schneider

Kurt Rufenacht

Rudolf C Thummel

Werner Fory

Walter Traber

Marcus Von Orelli

Alfons Lukaszczyk

Alfred Seiler

N-Phenyl-triazolopyrimidinyl-sulfonamides of formula I ##STR1## wherein R.sub.1 is halogen, phenyl, O-phenyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, --OR.sub.8, --OR.sub.9, nitro, hydroxy, cyano, --SR.sub.6, --SOR.sub.6, --SO.sub.2 R.sub.6, --SR.sub.8, --SOR.sub.8, --SO.sub.2 R.sub.8, --SO.sub.3 R.sub.8, --SR.sub.9, --SOR.sub.9, --SO.sub.2 R.sub.9, --SO.sub.2 NR.sub.10 (R.sub.10), --SO.sub.3 R.sub.9, --COOR.sub.7, --CONHR.sub.9, --CONR.sub.9 (R.sub.9), formyl, ##STR2## --NH.sub.2, --NHR.sub.9 or --NR.sub.9 (R.sub.9); R.sub.2 and R.sub.4 independently of one another are hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, --COOR.sub.7 or --OR.sub.9 ;

Triazolylsulfonamides

The present invention relates to the novel use of antidotes of formula I ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, and each of R.sup.2 and R.sup.3, independently of the other, is hydrogen, C.sub.1 -C.sub.3 alkyl, trifluoromethyl or cyclopropyl, with the proviso that only one of the symbols R.sup.2 and R.sup.3 may be hydrogen, for protecting cultivated plants from the phytotoxic action of herbicides. The invention relates also to novel compounds and the preparation thereof and to novel intermediates and the preparation thereof. The invention further relates to herbicidal compositions that contain a combination of herbicide and antidote and to corresponding methods of controlling weeds. Finally, the invention relates also to the seeds of cultivated plants protected by the treatment with the antidote.

1,2,4-triazolo-[1,5a]pyrimidin-2-yl derivatives

The present invention relates to novel N-phenyl-N-pyrimidin-2-ylureas having a herbicidal and plant growth-regulating activity, to agrochemical compositions containing those substances as active ingredients, to the use of the novel ureas for controlling weeds or for regulating plant growth, and to processes for the preparation of the novel compounds. The invention also relates to novel intermediates and to processes for the preparation thereof.

2-analino pyrimidine compounds

The present invention relates to the novel use of antidotes of formula I ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, and each of R.sup.2 and R.sup.3, independently of the other, is hydrogen, C.sub.1 -C.sub.3 alkyl, trifluoromethyl or cyclopropyl, with the proviso that only one of the symbols R.sup.2 and R.sup.3 may be hydrogen, for protecting cultivated plants from the phytotoxic action of herbicides. The invention relates also to novel compounds and the preparation thereof and to novel intermediates and the preparation thereof. The invention further relates to herbicidal composition that contain a combination of herbicide and antidote and to corresponding method of controlling weeds. Finally, the invention relates also to the seeds of cultivated plants protected by the treatment with the antidote.

1,2,4-triazolo[1,5-A]pyridi

The invention relates to processes for the preparation of 6-substituted 2-(imidazolin-2-yl)-nicotinic acid derivatives that are distinguished by excellent herbicidal and plant growth-regulating properties, and to intermediates and processes for the preparation of the intermediates. The derivatives correspond to formula I ##STR1## in which R.sub.1 represents hydrogen or a salt, ester or amide radical,

Process of preparing 2-(imidazolin-2-yl)-nicotinic acid compounds

The present invention relates to novel N-phenyl-N-pyrimidin-2-ylureas having a herbicidal and plant growth-regulating activity, to agrochemical compositions that contain those substances as active ingredients, to the use of the novel ureas for controlling weeds or for regulating plant growth, and to processes for the preparation of the novel compounds. The invention also relates to novel intermediates and to processes for the preparation thereof. The novel compounds correspond to formula I ##STR1## in which the radicals R.sup.1 to R.sup.6 have the meanings given in the text.

Novel ureas

The present invention relates to novel N-phenyl-N-pyrimidin-2-ylureas having a herbicidal and plant growth-regulating activity, to agrochemical compositions containing those substances as active ingredients, to the use of the novel ureas for controlling weeds or for regulating plant growth, and to processes for the preparation of the novel compounds. The invention also relates to novel intermediates and to processes for the preparation thereof. The novel compounds correspond to formula I ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 are each, independently of the others, hydrogen; 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; C.sub.1 -C.sub.4 alkyl-S(O).sub.n -; nitro; cyano; C.sub.1 -C.sub.4 alkoxycarbonyl; C.sub.1 -C.sub.4 alkylcarbonyl; di-(C.sub.1 -C.sub.4 alkylamino)-carbonyl; mono-(C.sub.1 -C.sub.4 alkylamino)carbonyl; carbamoyl; C.sub.1 -C.sub.4 haloalkyl-S(O).sub.n -; or -PO[O-(C.sub.1 -C.sub.4)-alkyl].sub.2 ;

N-phenyl-N-pyrimidin-2-ylureas

Novel thiazolylalkyl and thienylalkyl esters of .alpha.-imidazolinone-nicotinic and .alpha.-imidazolinonebenzoic acids of formula I below have good selective herbicidal properties pre- and postemergence and also influence or inhibit plant growth. The Novel esters have the formula I ##STR1## wherein A is a stright chain or branched C.sub.1 -C.sub.6 alkylene bridge,

Thiazolylalkyl esters of .alpha.-imidazolinonenicotinic acids and

Novel heterocyclylalkyl esters of 2-imidazolinonenicotinic acids of formula I below have good selective herbicidal properties pre- and postemergence and also influence or inhibit plant growth. The novel esters have the formula I ##STR1## wherein A is a straight chain or branched C.sub.1 -C.sub.4 alkylene bridge,

Heterocyclylalkyl esters of 2-imidazolinonenicotinic acids

Novel heterocyclylalkyl esters of 2-imidazolinonenicotinic acids of formula I below have good selective herbicidal properties pre- and postemergence and also influence or inhibit plant growth. The novel esters have the formula I ##STR1## wherein A is a straight chain or branched C.sub.1 -C.sub.4 alkylene bridge, X and Y are each independently of the other hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy or halogen, or X and Y together form the butadiene bridge, which may be substituted by halogen, cyano or C.sub.1 -C.sub.4 alkyl, and

There is disclosed a process for the preparation of 2-(imidazolin-2-yl)-3-pyridine and -3-quinolinecarboxylic acids of formula ##STR1## wherein R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.4 alkoxy, phenyl or phenyl-C.sub.1 -C.sub.4 alkyl, or phenyl or phenyl-C.sub.1 -C.sub.4 -alkyl, each substituted by one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl, phenyl-C.sub.1 -C.sub.4 -alkyl, or phenyl or phenyl-C.sub.1 -C.sub.4 -alkyl, each substituted by one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, R.sub.2 and R.sub.3 together are 1,3-butadienylene which can be substituted by 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 alkylsulfonyl, nitro, cyano, phenyl, phenoxy, or phenyl or phenoxy, each substituted by one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, and R.sub.4 and R.sub.5 are each independently of the other C.sub.1 -C.sub.4 alkyl. In this process, the 2-(imidazolin-2-yl)-3-pyridine- and -3-quinolinecarboxylic acids of the above formula are obtained by reacting a 2,3-pyridine- or 2,3-quinolinedidicarboxylic acid ester of formula ##STR2## wherein R.sub.1, and R.sub.2 and R.sub.3 are as defined above and R.sub.6 is C.sub.1 -C.sub.8 alkyl, phenyl or C.sub.1 -C.sub.4 phenylalkyl with a 2-aminoalkanecarboxamide of formula ##STR3## wherein R.sub.4 and R.sub.5 are as defined above, in an inert solvent and in the presence of a strong base, direct to a salt of a 2-(imidazolin-2-yl)-3-pyridine- or -3-quinolinecarboxylic acid of the above formula, from which the free 2-(imidazolin-2-yl)-3-pyridine- or -3-quinolinecarboxylic acids of the above formula are obtained by converting said salt into an aqueous solution and adding an acid. The 2-(imidazolin-2-yl)-3-pyridine- and -3-quinolinecarboxylic acids of the above formula have herbicidal properties and can be used for controlling undesired plant growth.

Process for the preparation of 2-(imidazolin-2-yl)-3-pyridine- and

This is a continuation in part application derived from our copending application Ser. No. 837,977 (filing date Mar. 10, 1986). This continuation in part is directed to novel pyridine compounds of formula I below have good selective herbicidal properties pre- and postemergence and also influence or inhibit plant growth. The compounds are of formula I ##STR1## wherein each of X, Y and Z independently of one another is hydrogen or a C.sub.1 -C.sub.4 alkyl group, or two adjacent substituents together also form a saturated or unsaturated 3- or 4-membered alkylene chain or alkenyl chain, each of which chains may in turn by substituted by one to four C.sub.1 -C.sub.4 alkyl groups, R is a C.sub.1 -C.sub.4 nitroalkyl group, a substituted C.sub.1 -C.sub.4 alkylthio group or C.sub.1 -C.sub.4 alkoxy group, an unsubstituted or substituted C.sub.3 -C.sub.4 alkenylthio or C.sub.3 -C.sub.4 alkynylthio group, the hydroxyamino group, a C.sub.1 -C.sub.4 alkoxyamino, C.sub.3 -C.sub.4 alkenyloxyamino or C.sub.3 -C.sub.4 alkynyloxyamino group, a --PO(C.sub.1 -C.sub.4 alkyl).sub.2 or --PO(CH.sub.3)OC.sub.1 -C.sub.4 -alkyl radical or an unsubstituted or substituted hydrazino radical.

Heterocyclically fused pyridine compounds as herbicides

This continuation-in-part is directed to novel pyridine compounds of formula I below have good selective herbicidal properties pre- and postemergence and also influence or inhibit plant growth. The compounds are of formula I ##STR1## wherein each of X, Y and Z independently of one another is hydrogen or a C.sub.1 -C.sub.4 alkyl group, or two adjacent substituents together also form a saturated or unsaturated 3- or 4-membered alkylene chain or alkenyl chain, each of which chains may in turn by substituted by one to four C.sub.1 -C.sub.4 alkyl groups and R is a C.sub.1 -C.sub.4 nitroalkyl group.

3H imidazo[1'2':2,2]pyrrolo[3,4-b]pyridine-2,5-dione, useful as

Novel pyridine compounds of formula I below have good selective herbicidal properties pre- and postemergence and also influence or inhibit plant growth. The compounds are of formula I ##STR1## wherein each of X, Y and Z independently of one another is hydrogen or a C.sub.1 -C.sub.4 alkyl group, or two adjacent substituents together also form a saturated or unsaturated 3- or 4-membered alkylene chain or alkenyl chain, each of which chains may in turn by substituted by one to four C.sub.1 -C.sub.4 alkyl groups, R is the hydroxyamino group, a C.sub.1 -C.sub.4 alkoxyamino, C.sub.3 -C.sub.4 alkenyloxyamino or C.sub.3 -C.sub.4 alkynyloxyamino group, a --PO(C.sub.1 -C.sub.4 alkyl).sub.2 or --PO(CH.sub.3)OC.sub.1 -C.sub.4 alkyl radical or an unsubstituted or substituted hydrazino radical.

Growing community of inventors

Bottmingen, Switzerland

Dieter Durr