Pyrazolo-(1,5a)-pyrimidines, process for preparing the same and

Details Pyrazolo-(1,5a)-pyrimidines, process for preparing the same and Pyrazolo-(1,5a)-pyrimidines, process for preparing the same and

1997-10-28

1999-05-11

Dees, Jose' G.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504241, 544253, 544278, 544279, C07D487/04

Patent

active

059027738

DESCRIPTION:

BRIEF SUMMARY
##STR2## where the indices and the substituents have the following meanings: n is 0 or 1; CH.sub.2 O*, CH.sub.2 S*, CH.sub.2 NR.sup.a *, CH.sub.2 CH.sub.2, CR.sup.a .dbd.R.sup.b or C.tbd.C, the positions identified by * marking the bond to the phenyl ring; CNH--CO--.circle-solid..dbd.CHOCH.sub.3, H.sub.3 CO--CO--.circle-solid...dbd.NOCH.sub.3, H.sub.3 CNH--CO--.circle-solid...dbd.NOCH.sub.3, H.sub.2 N--CO--.circle-solid...dbd.NOCH.sub.3, HO--CO--.circle-solid...dbd.NOCH.sub.3, H.sub.3 CO--CO--.circle-solid...dbd.CHCH.sub.3, H.sub.3 CO--CO--.circle-solid...dbd.CHCH.sub.2 CH.sub.3, H.sub.3 C--CO--.circle-solid...dbd.CHOCH.sub.3, H.sub.3 C--CO--.circle-solid...dbd.NOCH.sub.3, H.sub.3 CCH.sub.2 --CO--.circle-solid..dbd.NOCH.sub.3, .circle-solid. being a C atom bonded to the phenyl ring; CH.sub.3)--CO.sub.2 CH.sub.3, or a group R'.1--.circle-solid..dbd.NOCH.sub.3, R'.2-.circle-solid..dbd.NOCH.sub.3, R'.3--.circle-solid..dbd.NOCH.sub.3 or R'.4--.circle-solid..dbd.NOCH.sub.3, ##STR3## m is 0, 1, 2 or 3, it being possible for radicals R" to be different if m is greater than 1; C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, or NR.sup.c R.sup.d, NR.sup.c NR.sup.d R.sup.e, CO--R.sup.c, CO.sub.2 --R.sup.c, CO--NR.sup.c R.sup.d, O--CO--R.sup.c, O--CO.sub.2 --R.sup.c, O--CO--NR.sup.c R.sup.d, NR.sup.c --CO--R.sup.d, NR.sup.c --CO.sub.2 --R.sup.d or NR.sup.c --CO--NR.sup.d R.sup.e ; aryloxy, heteroaryl, heteroaryloxy, CO--R.sup.c, CO.sub.2 --R.sup.c or CR.sup.f .dbd.NOR.sup.g ; alkoxy, haloalkoxy, alkylthio, haloalkylthio, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylalkoxy, heteroarylthio, or NR.sup.c R.sup.d, CO--R.sup.c, CO.sub.2 --R.sup.c or CR.sup.f .dbd.NOR.sup.g ; C.sub.1 -C.sub.4 -haloalkyl; arylalkyl, heteroaryl or heteroarylalkyl; alkylthio, alkenyl, alkenyloxy, alkenylthio, alkynyl, alkynyloxy, alkynylthio, cycloalkyl, cycloalkyloxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy or heteroarylthio; cycloalkyl, heterocyclyl, aryl or heteroaryl, for controlling pests and harmful fungi.
In the literature, for example, fungicidally active compounds are disclosed isoquinolinyl or benzopyrazinyl radical (EP-A 278 595). Corresponding active compounds having pyridyl, pyridazinyl, pyrimidyl, pyrazinyl, triazinyl or tetrazinyl radicals are additionally described (EP-A 398 692, EP-A 254 426).
It is an object of the present invention to provide novel active compounds having an improved spectrum of action. defined at the beginning. Processes for their preparation, compositions containing them and their use for controlling pests and harmful fungi have additionally been found.
The compounds I are prepared in a similar manner to various methods known per se from the literature. In the preparation, it is in general insignificant whether the group R is synthesized first or whether the pyrazolopyrimidine radical is coupled to Y first. Depending on the stability of the intermediates, it is also possible to carry out the coupling to the pyrazolopyrimidine in the individual stages of the synthesis of R.
Accordingly, for greater clarity in the following reaction equations the pyrazolopyrimidine group or its precursors, if they are not involved in the reaction, are shown in abbreviated form as R*.
In the preparation of the compounds I where Y.sub.n is OCH.sub.2 *, !, a procedure is in general followed in which a benzyl derivative of the formula IIa is reacted in a manner known per se in an inert organic solvent in the presence of a base with a pyrazolopyrimidine of the formula IIIa. ##STR4##
L.sup.1 in the formula IIa is a nucleophilically replaceable leaving group such as halogen (eg. chlorine, bromine or iodine) or a sulfonate (eg. trifluoromethylsul

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