Ciba-geigy Corporation

Ciba-geigy Ag

Henry Martin

Werner Fory

Georg Pissiotas

Urs Fricker

Elmar Sturm

Heinrich Schempp

Henry Szczepanski

Rolf Schurter

Hermann Rempfler

Beat Muller

Haukur Kristinsson

Rene Eric Muntwyler

Peter J Diel

Johannes P Pachlatko

Volker Dittrich

Alfons Lukaszczyk

Karl Gatzi

Karl Gotzi

The invention relates to novel oxime ethers of the formula I ##STR1## wherein R.sub.1 is hydrogen, halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, lower alkylthio, lower haloalkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower haloalkylsulfinyl, lower haloalkylsulfonyl or nitro, each of R.sub.2 and R.sub.3 is hydrogen, halogen, lower alkyl, lower alkoxy or lower haloalkoxy, and Q is an unsubstituted or substituted lower alkyl, lower alkenyl, lower alkynyl or cycloalkyl group, a lower alkanoyl radical, an aliphatic, cycloaliphatic, aromatic or heterocyclic acyl radical which may be substituted or unsubstituted, a carbonyl or thiocarbonyl radical, an aryl or aralkyl radical, an acylimidomethyl radical, a phthalimidomethyl radical or a heterocyclic radical. These compounds are able to act as antidotes or safeners for protecting cultivated plants from the phytotoxic action of aggressive herbicides. Preferred crops are sorghum, cereals, maize and rice, and herbicides are chiefly chloroacetanilides and thiocarbamates.

Novel oxime ethers, the preparation thereof, compositions containing

A composition for protecting culture plants from the phytotoxic action of herbicidally active chloracetanilides contains as active ingredient an acylamine derivative of the formula I ##STR1## wherein X is oxygen, sulfur, --SO-- or --SO.sub.2 --,

Composition for protecting culture plants from the phytotoxic action of

Compositions for protecting culture plants from the phytotoxic action of

Oxime ethers as herbicidal safeners

There are used for the protection of cultivated plants against the harmful effects of agricultural chemicals quinoline derivatives of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 independently of one another are each hydrogen, halogen, nitro, cyano, alkyl, alkoxy or acyl,

Quinoline derivatives and compositions thereof for the protection of

A process for protecting cultivated plants against aggressive agricultural chemicals is described in which oxide derivatives of the formula ##STR1## are used as antidotes. Either the cultivated area for the cultivated plants or the cultivated plants themselves or parts of the plant (seeds, tubers, stem parts, and the like), as desired, can be treated with these oxide derivatives, which are used as a dressing.

Thiadiazolyl-glyoxylonitrile-2-oxime ether derivatives for protecting

The oxime ethers of the formula I below are able to act as antidotes or safeners to protect cultivated plants from the phytotoxic effects of herbicides. Such cultivated plants are preferably sorghum, cereals, maize and rice, and herbicides are principally chloroacetanilides and thiocarbamates. The oxime ethers have the formula I ##STR1## wherein n is 1 or 2, each of R.sub.1 and R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl each of R.sub.3 and R.sub.4 is hydrogen, 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, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl or nitro; each of R.sub.5 and R.sub.6 independently of the other is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.8 alkoxyalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, or together form a 2- to 6-membered alkylene or alkenylene bridge which may be substituted by 1 to 4 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.8 alkoxyalkyl or C.sub.3 -C.sub.8 alkenyloxyalkyl groups; each of A and B independently of the other is oxygen or sulfur, or one of A and B is the methine group, X is a fluorinated C.sub.1 -C.sub.3 alkyl radical which may also additionally contain chlorine, and Y is hydrogen, 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 phenyl.

Phenoxine-ketal ethers, compositions containing them and the use thereof

The invention relates to oxime ethers of the formula I ##STR1## wherein n is 1 or 2, each of R.sub.1 and R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl each of R.sub.3 and R.sub.4 is hydrogen, 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, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl or nitro; each of R.sub.5 and R.sub.6 independently of the other is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, phenyl or phenyl which is substituted by 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, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, carboxyl, carbamoyl, C.sub. 1 -C.sub.4 alkylcarbamoyl, nitro or cyano, or R.sub.5 and R.sub.6 together are also a 2- to 6-membered alkylene or alkenylene chain which may be substituted by C.sub.1 -C.sub.4 alkyl radicals; X is hydrogen, cyano, nitro, chlorine, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, carboxyl, carbamoyl, C.sub.1 -C.sub.4 alkylcarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl or C.sub.1 -C.sub.4 alkylcarbamoyl. The oxime ethers of the formula I are able to act as antidotes or safeners to protect cultivated plants from the phytotoxic effects of herbicides. Such cultivated plants are preferably sorghum, cereals, maize and rice.

Oxime ethers, the preparation thereof, compositions containing them and

Novel oxime ethers and oxime esters of the formula I given herein have various advantageous effects with regard to stimulation of plant growth, particularly in the early stage of development of the plant. Furthermore, such compounds have the property of rendering, in the sense of an antidote action, agricultural chemicals which would otherwise damage the plants (phytotoxic chemicals) more compatible with the cultivated plants. Herbicides that are insufficiently selective can be used for example in the presence of such oxime derivatives in specific cultivated crops for combating weeds, without disadvantageous consequences for the cultivated plants.

Compositions, which promote plant growth and protect plants, based on

The oxime ethers of the formula I below are able to act as antidotes or safeners to protect cultivated plants from the phytotoxic effects of herbicides. Such cultivated plants are preferably sorghum, cereals, maize and rice, and herbicides are principally chloroacetanilides and thiocarbamates. The oxime ethers have the formula I ##STR1## wherein n is 1 or 2, each of R.sub.1 and R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl each of R.sub.3 and R.sub.4 is hydrogen, 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, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl or nitro; each of R.sub.5 and R.sub.6 independently of the other is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.8 alkoxyalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, or together form a 2- to 6-membered alkylene or alkenylene bridge which may be substituted by 1 to 4 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.8 alkoxyalkyl or C.sub.3 -C.sub.8 alkenyloxyalkyl groups; each of A and B independently of the other is oxygen or sulfur, or one of A and b is the methine group, X is a fluorinated C.sub.1 -C.sub.3 alkyl radical which may also additionally contain chlorine, and Y is hydrogen, 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 phenyl.

Oxime ethers, compositions containing them and the use thereof

Oxime derivatives of the formula (I) ##STR1## wherein n is 0, 1 or 2 and m is 0 or 1, and

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Allschwil, Switzerland

Henry Martin