Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1996-03-01
1998-05-12
Ford, John M.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
544238, 544295, 544296, 544212, 544209, 544219, 544300, 544301, 544302, 544310, 540598, 540601, 540480, 540481, 504219, 504230, 504236, 504235, 504237, 504238, C07D23960, A01N 4354
Patent
active
057504695
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of PCT EP94/02825 filed Sep. 25, 1994.
The present invention relates to substituted lactic acid derivatives having an N-organic radical in the .beta.-position, of the formula I ##STR7## where R is a formyl group, a group CO.sub.2 H or a radical which can be hydrolyzed to give COOH and the other substituents have the following meanings: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; 3- or 4-membered alkylene or alkenylene chain in which one methylene group in each case is replaced by oxygen; C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, or R.sup.3 is linked with R.sup.13 as indicated above to give a 5- or 6-membered ring; cycloalkenyl, it being possible for a CH.sub.2 group in the ring to be replaced by an oxygen or sulfur atom, alkyl, alkenyl, alkynyl, phenyl, naphthyl or a five- or six-membered heteroaromatic comprising one to three nitrogen atoms and/or one sulfur or oxygen atom; to 8-membered ring which can contain one oxygen or sulfur atom and can carry one to three of the following radicals: 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 or C.sub.1 -C.sub.4 -alkylthio; alkoxycarbonyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkylthioalkyl or unsubstituted or substituted phenyl, or R.sup.5 is linked with R.sup.4 as indicated above to give a ring; ##STR8## where R.sup.14 and R.sup.15 are hydrogen, an aliphatic, cycloaliphatic or aromatic C-organic radical having up to 20 carbon atoms or together form an unsubstituted or substituted C.sub.4 -C.sub.7 -alkylene chain which is closed to give a ring, in which a methylene group can be replaced by oxygen, sulfur or nitrogen; ##STR9## where the radicals have the following meanings: R.sup.16 is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl or unsubstituted or substituted phenyl; ##STR10## OR.sup.19 or --NR.sup.14 R.sup.15, where R.sup.14 and R.sup.15 have the abovementioned meanings and R.sup.17 or R.sup.19 is defined as follows: phenyl or substituted phenyl; substituted phenyl; ##STR11## where R.sup.14 and R.sup.15, have the abovementioned meanings; R.sup.19 is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, phenyl or substituted phenyl; ##STR12## where R.sup.20 and R.sup.21, which can be identical or different, are: hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or phenyl, where the organic radicals can in each case be substituted; C.sub.4 -C.sub.7 -alkylene chain which is closed to give a ring or together form an unsubstituted or substituted C.sub.3 -C.sub.6 -alkylene chain which is closed to give a ring and has a heteroatom selected from the group consisting of oxygen, sulfur and nitrogen.
In the literature, e.g. EP-A 347 811, EP-A 400 741, EP-A 409 368, EP-A 481 512, EP-A 517 215, EP-A 541 041, JP 043 34372-A and EP-A 548 710, similar compounds are described as herbicidally active. The biological action and selectivity of these compounds, however, is not always satisfactory.
It is an object of the present invention to provide compounds having improved selectivity toward crop plants and/or better herbidical or bioregulatory action.
We have found that this object is achieved by the lactic acid derivatives I defined at the outset, which have excellent herbicidal and plant growth-regulating properties. We have moreover found that the lactic acid derivatives I have a good antagonistic action against herbicides of the cyclohexenone type XIII.
The invention therefore also relates to herbicidal compositions, comprising a lactic acid derivative of the formula I and at least one herbidical active compound from the group of cyclohexenone derivatives of the general formula XIII ##STR13## where the substituents have the following meanings: R.sup.a is a C.sub.1 -C.sub.6 -alkyl group; a C.sub.2 -C.sub.8 -alkylcarbonyl group, a C.sub.1 -C.sub.10 -alkylsulfonyl group, a C.sub.1 -C.sub.10 -alkylphosphonyl group or the benzoyl, benzenesulfonyl or benzenephosphonyl group, where the three last-mention
REFERENCES:
patent: 5270289 (1993-12-01), Harde et al.
patent: 5326744 (1994-07-01), Rheinheimer et al.
patent: 5446013 (1995-08-01), Zurmuehlen et al.
Baumann Ernst
Gerber Matthias
Rademacher Wilhelm
Rheinheimer Joachim
Vogelbacher Uwe Josef
BASF - Aktiengesellschaft
Ford John M.
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