Inhibitors of hydroxyphenylpyruvate dioxygenase and an assay for identification of inhibitors
AssigneeHoechst Aktiengesellschaft
InventorArno Schulz
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Abstract
There are described a method for enriching the anabolic p-hydroxyphenylpyruvate dioxygenases from plant tissues and a method by means of which the enzymatic activity of the enzyme can be measured in a simple manner without complete purification of the enzyme being necessary. The invention furthermore describes an assay system for identifying inhibitors of p-hydroxyphenylpyruvate dioxygenase from plants, in which an enriched HPPD from plants is incubated with a test substrate to be examined and the enzymatic activity of the enzyme is determined in comparison with the activity of the uninhibited enzyme. The invention furthermore describes the novel herbicidal active substances of the formula (I) ##STR1## which were found using the assay method according to the invention.
Claims9
A herbicidal compound of the formula (I) ##STR212## in which R.sup.1 is H, halogen, OH, alkoxy, CN, NO.sub.2 or haloalkyl,
- R.sup.2 is H, halogen, OH, alkyl, alkoxy, haloalkyl, haloalkoxy or (alkoxy)carbonyl,
- R.sup.3 is H, halogen, OH, CN, NO.sub.2, haloalkyl, haloalkoxy or R.sup.4 S(O).sub.m --, where R.sup.4 is alkyl and m is zero, one or two,
- Q is a radical selected from the group consisting of radicals of the formula ##STR213## in which R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 independently of one another are H, halogen, OH, CN, NO.sub.2, SO.sub.3 H, SO.sub.3 R.sup.4, SO.sub.2 NR.sup.14 R.sup.15, COOH, COOR.sup.4, CONR.sup.14 R.sup.15, O--COOR.sup.4, O--COR.sup.4, alkyl, alkoxy, haloalkyl or haloalkoxy,
- R.sup.10, R.sup.11 and R.sup.12 independently of one another are H, halogen, alkyl, alkoxy, haloalkyl or haloalkoxy,
- R.sup.13 is H, phenylsulfonyl, alkylsulfonyl or alkylcarbonyl,
- R.sup.14 and R.sup.15 independently of one another are H, alkyl, aryl or benzyl,
- with the following provisos:
- (i) R.sup.1 to R.sup.3 or R.sup.5 to R.sup.9 are not simultaneously hydrogen;
- (ii) R.sup.5, R.sup.7 and R.sup.9 are not simultaneously hydroxy;
- (iii) when R.sup.3 is alkoxy then R.sup.5 or R.sup.9 is halogen and when R.sup.7 is alkoxy then R.sup.6 or R.sup.8 is not hydrogen;
- and
- (iv) when R.sup.1 is hydroxy then R.sup.5 and R.sup.9 are not hydroxy.
A herbicidal compound of the formula (I) ##STR217## in which:
- R.sup.1 is hydrogen, halogen or hydroxy,
- R.sup.2 is hydrogen or halogen,
- R.sup.3 is halogen, hydroxy, NO.sub.2, or R.sup.4 S(O).sub.m --, where R.sup.4 is alkyl and m is zero, one or two,
- Q is a radical selected from the group consisting of radicals of the formula ##STR218## in which R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 independently of one another are H, halogen, OH, CN, NO.sub.2, SO.sub.3 H, SO.sub.3 R.sup.4, SO.sub.2 NR.sup.14 R.sup.15, COOH, COOR.sup.4, CONR.sup.14 R.sup.15, O--COOR.sup.4, O--COR.sup.4, alkyl, alkoxy, haloalkyl or haloalkoxy,
- R.sup.10, R.sup.11 and R.sup.12 independently of one another are H, halogen, alkyl, alkoxy, haloalkyl or haloalkoxy,
- R.sup.13 is H, phenylsulfonyl, alkylsulfonyl or alkylcarbonyl,
- R.sup.14 and R.sup.15 independently of one another are H, alkyl, aryl or benzyl,
- with the proviso that R.sup.5 to R.sup.9 are not simultaneously hydrogen.
A herbicidal compound of the formula (I) ##STR219## in which:
- R.sup.1 is halogen,
- R.sup.2 is hydrogen,
- R.sup.3 is R.sup.4 S(O).sub.m --, where R.sup.4 is alkyl and m is zero, one or two,
- Q is a radical selected from the group consisting of radicals of the formula ##STR220## in which R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 independently of one another are H, halogen, OH, CN, NO.sub.2, SO.sub.3 H, SO.sub.3 R.sup.4, SO.sub.2 NR.sup.14 R.sup.15, COOH, COOR.sup.4, CONR.sup.14 R.sup.15, O--COOR.sup.4, O--COR.sup.4, alkyl, alkoxy, haloalkyl or haloalkoxy,
- R.sup.10, R.sup.11 and R.sup.12 independently of one another are H, halogen, alkyl, alkoxy, haloalkyl or haloalkoxy,
- R.sup.13 is H, phenylsulfonyl, alkylsulfonyl or alkylcarbonyl,
- R.sup.14 and R.sup.15 independently of one another are H, alkyl, aryl or benzyl.
A herbicidal compound of the formula (I) ##STR221## in which:
- R.sup.1 is chlorine,
- R.sup.2 is hydrogen,
- R.sup.3 is SO.sub.2 CH.sub.3,
- Q is a radical selected from the group consisting of radicals of the formula ##STR222## in which R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 independently of one another are H, halogen, OH, CN, NO.sub.2, SO.sub.3 H, SO.sub.3 R.sup.4, SO.sub.2 NR.sup.14 R.sup.15, COOH, COOR.sup.4, CONR.sup.14 R.sup.15, O--COOR.sup.4, O--COR.sup.4, alkyl, alkoxy, haloalkyl or haloalkoxy,
- R.sup.10, R.sup.11 and R.sup.12 independently of one another are H, halogen, alkyl, alkoxy, haloalkyl or haloalkoxy,
- R.sup.13 is H, phenylsulfonyl, alkylsulfonyl or alkylcarbonyl,
- R.sup.14 and R.sup.15 independently of one another are H, alkyl, aryl or benzyl.
Dependencies are inferred from the claim text.