Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1993-09-17
1996-04-09
Ramsuer, Robert W.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
514403, 546279, 5483664, A01M 4356, C07D23134, C07D23136
Patent
active
055061931
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to herbicidally, acaricidally and insecticidally active pyrazolidine-3,5-diones of the formula I, to processes for their preparation, and to novel intermediates for these processes. The invention furthermore relates to herbicidally, acaricidally or insecticidally active compositions as well as methods for controlling weeds, Acarina or insects.
The compounds according to the invention are those of the formula I ##STR4## in which R.sub.1 is ##STR5## R.sub.2 and R.sub.3 independently of one another are C.sub.1 -C.sub.6 alkyl; C.sub.3 -C.sub.6 alkenyl; or C.sub.3 -C.sub.6 alkynyl; or --(CH.sub.2).sub.4 --, --CH.sub.2 --CH.dbd.CH--CH.sub.2 --, --CH.sub.2 --CH.dbd.CH-- or --(CH.sub.2).sub.2 --CH.dbd.CH-- bridge which is unsubstituted or up to trisubstituted by C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.10 alkoxy; C.sub.1 -C.sub.4 haloalkoxy; C.sub.3 -C.sub.6 alkenyloxy; C.sub.1 -C.sub.4 alkoxy-C.sub.2 -C.sub.4 alkoxy; C.sub.3 -C.sub.6 alkynyloxy; C.sub.1 -C.sub.4 alkylcarbonyl; C.sub.1 -C.sub.4 alkoxycarbonyl; C.sub.1 -C.sub.4 alkylthio; C.sub.1 -C.sub.4 alkylsulfinyl; C.sub.1 -C.sub.4 alkylsulfonyl; amino; mono-C.sub.1 -C.sub.4 alkylamino; di-C.sub.1 -C.sub.4 alkylamino; ##STR6## X is oxygen; sulfur; CH.sub.2 ; or NR.sub.7 ; o is 0; 1; 2; or 3; halogen; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.4 haloalkoxy; C.sub.1 -C.sub.4 alkoxy; nitro; cyano; C.sub.1 -C.sub.4 alkoxycarbonyl; amino; mono-C.sub.1 -C.sub.4 alkylamino; or di-C.sub.1 -C.sub.4 alkylamino; and alkylcarbonyl;
Suitable acids for forming such acid addition salts are both organic and inorganic acids. Examples of such acids are, inter alia, hydrochloric acid, hydrobromic acid, nitric acid, various phosphoric acids, sulfuric acid, acetic acid, propionic acid, butyric acid, valeric acid, oxalic acid, malonic acid, maleic acid, fumaric acid, lactic acid, tartaric acid or salicylic acid.
Because of their chemical constitution, the compounds of the formula I can exist in the tautomeric equilibrium forms I.revreaction.I'.revreaction.I": ##STR7##
Moreover, certain substituents R.sub.1 to R.sub.7, on their own or in combination with each other or in combination with the skeleton to which they are bonded, can have centres of chirality.
The invention extends to the racemate as well as to the enriched and optically pure forms of the stereoisomers in question.
In the processes described in the present application, the asymmetrically substituted compounds of the formula I are generally obtained in the form of racemates, unless chiral educts are used. The stereoisomers can then be isolated by methods known per se, such as fractional crystallisation following salt formation with optically pure bases, acids or metal complexes, or, alternatively, by chromatographic methods on the basis of their physicochemical properties.
The compounds of the formula I in which the radicals R.sub.2 and R.sub.3 are alkyl, alkenyl or alkynyl radicals are derivatives of the pyrazolidine-3,5-dione system. In those cases in which R.sub.2 and R.sub.3 are a saturated or partially unsaturated C.sub.4 -carbon bridge, formula I is based on the ring system of the 1H-pyrazolo[1,2-a]pyridazine, and in those cases in which R.sub.2 and R.sub.3 are a saturated or partially unsaturated C.sub.3 -carbon bridge, it is based on the ring system of 1H,5H-pyrazolo[1,2-a]pyrazole. The individual ring positions are numbered analogously to Chemical Abstracts: ##STR8##
Halogen in the above definitions is to be understood as meaning fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine.
Monoalkylamino is, in particular, methylamino, ethylamino, n-propylamino, i-propylamino and the isomeric butylamino radicals.
Dialkylamino within the given limits of the definition is the radical which is substituted by identical as well as different alkyl radicals; in particular dimethylamino, methylethylamino, diethylamino, dibutylamino and diisopropylamino.
Alkyl is methyl, ethyl, isopropyl, n-propyl, n-butyl, iso-butyl, sec-butyl,
REFERENCES:
patent: 4128425 (1978-12-01), Greenwald
Komatsu et al, Tetrahedron Letters, vol. 31 (1990) pp. 5327-5330.
Boger Manfred
Brunner Hans-Georg
Cederbaum Frederik
Ciba-Geigy Corporation
Mathias Marla J.
Ramsuer Robert W.
Teoli, Jr. William A.
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