Isoxazolines, their preparation, and their use as plant-protecting agents
AssigneeHoechst Aktiengesellschaft
InventorsHeinz J. Loher, Wilfried Schwab, Klaus Bauer, Hermann Bieringer
Life of this patent
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Abstract
Compounds of the formula (I) ##STR1## and their use as antidotes against the phytotoxicity of many herbicides used on crops, without diminishing the effect of the herbicide against weeds.
Claims11
A compound of the formula (I) or a salt thereof ##STR12## where the Z radicals independently of one another are halogen, nitro, cyano, or alkyl, alkoxy, alkylthio or cycloalkyl, the four last-mentioned radicals being unsubstituted or monosubstituted or polysubstituted by alkoxy, hydroxyl or halogen, or furthermore are amino, mono- or dialkylamino, phenyl or phenoxy, phenyl and phenoxy independently of one another being unsubstituted or monosubstituted or polysubstituted by halogen or halogenoalkyl, or two adjacent substituents Z together are a divalent group of the formula --OCH.sub.2 O--, --S--CH.sub.2 --O-- or --S--CH.sub.2 --S--, which group is unsubstituted or substituted by alkyl,
- n is an integer from 0 to 5,
- X is hydroxyl or alkoxy, alkenyloxy, alkynyloxy, alkylthio or cycloalkoxy, the five last-mentioned radicals being unsubstituted or monosubstituted or polysubstituted by radicals from the group comprising alkoxy, alkylthio, mono- and dialkylamino, phenyl, cyano and halogen, or is furthermore phenoxy, or is furthermore trialkylsilylmethoxy, a radical of the formula ##STR13## where R in each case is hydrogen or alkyl, Z.sup.1 independently of Z has the meanings mentioned above in the case of Z, and n.sup.1 is an integer from 0 to 5, or is furthermore amino, mono- or dialkylamino, cycloalkylamino, hydrazino, alkyl- or dialkylhydrazino, pyridino, morpholino, dimethylmorpholino, a radical of the formula ##STR14## where R.sup.1 and R.sup.2 independently of one another are alkyl radicals or R.sup.1 and R.sup.2 together with the carbon tom linking them form a cycloalkyl radical, or is furthermore a radical of the formula ##STR15## where R.sup.3 and R.sup.4 independently of one another are hydrogen or alkyl, with the exception of a compound of formula (I) in which n is zero and X is a radical of the formula ##STR16## in which R is hydrogen, and Z.sup.1 is hydrogen or chlorine.
A method of controlling undesired plants in crops, which comprises applying to the plants, seeds of the plants or the cropping area, a herbicide in combination with a compound of the formula (I) or a salt thereof ##STR21## where the Z radicals independently of one another are halogen, nitro, cyano, or alkyl, alkoxy, alkylthio or cycloalkyl, the four last-mentioned radicals being unsubstituted or monosubstituted or polysubstituted by alkoxy, hydroxyl or halogen, or furthermore are amino, mono- or dialkylamino, phenyl or phenoxy, phenyl and phenoxy independently of one another being unsubstituted or monosubstituted or polysubstituted by halogen or halogenoalkyl, or two adjacent substituents Z together are a divalent group of the formula --OCH.sub.2 O--, --S--CH.sub.2 --O-- or --S--CH.sub.2 --S--, which group is unsubstituted or substituted by alkyl,
- n is an integer from 0 to 5,
- X is hydroxyl or alkoxy, alkenyloxy, alkynyloxy, alkylthio or cycloalkoxy, the five last-mentioned radicals being unsubstituted or monosubstituted or polysubstituted by radicals from the group comprising alkoxy, alkylthio, mono- and dialkylamino, phenyl, cyano and halogen, or is furthermore phenoxy, or is furthermore trialkylsilylmethoxy, a radical of the formula ##STR22## where R in each case is hydrogen or alkyl, Z.sup.1 independently of Z has the meanings mentioned above in the case of Z, and n.sup.1 is an integer from 0 to 5, or is furthermore amino, mono- or dialkylamino, cycloalkylamino, hydrazino, alkyl- or dialkylhydrazino, pyridino, morpholino, dimethylmorpholino, a radical of the formula ##STR23## where R.sup.1 and R.sup.2 independently of one another are alkyl radicals or R.sup.1 and R.sup.2 together with the carbon atom linking them form a cycloalkyl radical, or is furthermore a radical of the formula ##STR24## where R.sup.3 and R.sup.4 independently of one another are hydrogen or alkyl.
A method for protecting crop plants against phytotoxic secondary effects of a herbicide, wherein a herbicide is applied to the plants, seeds of the plants or the cropping area in combination with a compound of the formula (I) or a salt thereof ##STR25## where the radicals independently of one another are halogen, nitro, cyano, or alkyl, alkoxy, alkylthio or cycloalkyl, the four last-mentioned radicals being unsubstituted or monosubstituted or polysubstituted by alkoxy, hydroxyl or halogen, or furthermore are amino, mono- or dialkylamino, phenyl or phenoxy, phenyl and phenoxy independently of one another being unsubstituted or monosubstituted or polysubstituted by halogen or halogenoalkyl, or two adjacent substituents Z together are a divalent group of the formula --OCH.sub.2 O--, --S--CH.sub.2 --O-- or --S--CH.sub.2 --S--, which group is unsubstituted or substituted by alkyl,
- n is an integer from 0 to 5,
- X is hydroxyl or alkoxy, alkenyloxy, alkynyloxy, alkylthio or cycloalkoxy, the five last-mentioned radicals being unsubstituted or monosubstituted or polysubstituted by radicals from the group comprising alkoxy, alkylthio, mono- and dialkylamino, phenyl, cyano and halogen, or is furthermore phenoxy, or is furthermore trialkylsilylmethoxy, a radical of the formula ##STR26## where R in each case is hydrogen or alkyl, Z.sup.1 independently of Z has the meanings mentioned above in the case of Z, and n.sup.1 is an integer from 0 to 5, or is furthermore amino, mono- or dialkylamino, cycloalkylamino, hydrazino, alkyl- or dialkylhydrazino, pyridino, morpholino, dimethylmorpholino, a radical of the formula ##STR27## where R.sup.1 and R.sup.2 independently of one another are alkyl radicals or R.sup.1 and R.sup.2 together with the carbon atom linking them form a cycloalkyl radical, or is furthermore a radical of the formula ##STR28## where R.sup.3 and R.sup.4 independently of one another are hydrogen or alkyl.
Dependencies are inferred from the claim text.