Herbicidal imidazolones

Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing

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504241, 504246, 504249, 504266, 504276, 504277, 504278, 504279, 504222, 504225, 504235, 544 48, 544105, 544281, 544350, 544139, 546128, 546199, 548126, 5483029, 5483164, 5483171, 5483231, 5483235, 5483241, 5483245, 5483255, 5483225, C07D47104, C07D23502, C07D49804, C07D48704, A01N 4390, A01N 4350

Patent

active

056438559

DESCRIPTION:

BRIEF SUMMARY
This invention comprises novel imidazolones and their agriculturally suitable salts for weed control in crops. This invention further comprises a simple one-pot procedure for preparing amino amides from the corresponding .alpha.-amino acid, ester or lactone, a trialkylaluminum and an amine, the reaction proceeding with retention of configuration and without the need for prior protection of the .alpha.-amino moiety.
Certain related imidazolidinone derivatives with analgesic, anti-inflammatory and antipyretic activities are disclosed in U.S. Pat. No. 3,442,892 as pharmaceuticals. The imidazolones of the present invention are not disclosed therein.
A general method for the conversion of esters to amides by reaction of an aluminum amide with an ester has been described, see for example, Weinreb et al., Tetrahedron Lett., (1977), 4171-4174. Weinreb et al. discloses the amidation of a protected N-acetyl amino acid, however, no mention is made of unprotected amino acids or peptides or the retention or loss of configuration at the carbon bearing the amino moiety. Numerous prior art methods are known for the amidation of protected .alpha.-amino acids or esters, however, the prior art does not disclose the direct amidation of unprotected .alpha.-amino acids or esters without substantial concomitant racemization when the .alpha.-amino acids or esters are enantiomerically enriched.
The present invention demonstrates an advance over the prior art by the direct synthesis of .alpha.-amino amides from the corresponding .alpha.-amino acids, esters or lactones, without prior protection of the amino group and with retention of configuration at the carbon bearing the .alpha.-amino group. A specific application of the method of the present invention is the synthesis of peptides.


SUMMARY OF THE INVENTION

The compounds of this invention are compounds of the formula: ##STR3## wherein Q is ##STR4## R.sup.1 is H; C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl; or halogen; halogens, OR.sup.8, CN, COR.sup.9, CO.sub.2 R.sup.31 or CONR.sup.32 R.sup.33 ; CN; CO.sub.2 R.sup.34 ; CONR.sup.35 R.sup.36 ; S(O).sub.n R.sup.8 ; S(O).sub.n NR.sup.19 R.sup.8 or COR.sup.37 ; or they are attached to form C.dbd.CHCO.sub.2 R.sup.31 ; C.dbd.C(CH.sub.3)CO.sub.2 R.sup.31 ; C.dbd.C(C.sub.2 H.sub.5)CO.sub.2 R.sup.31 ; C.dbd.CHCONR.sup.32 R.sup.33 ; C.dbd.C(CH.sub.3)CONR.sup.32 R.sup.33 or C.dbd.C(C.sub.2 H.sub.5)CONR.sup.32 R.sup.33 ; alkenyl; C.sub.2 -C.sub.4 alkynyl; OR.sup.10 ; SR.sup.10 or halogen; alkenyl or C.sub.3 -C.sub.4 alkynyl; connected to nitrogen and Z is connected to G; O; or S(O).sub.n ; halogen; C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl; or --CH.sub.2 --; -C.sub.6 alkenyl; C.sub.3 -C.sub.6 cycloalkyl or phenyl optionally substitituted with one or more CH.sub.3, OCH.sub.3, NO.sub.2, CN or halogens; OH; OR.sup.17 ; SH; S(O).sub.n R.sup.17 ; COR.sup.17 ; CO.sub.2 R.sup.17 ; C(O)SR.sup.17 ; C(O)NR.sup.19 R.sup.20 ; CHO; CR.sup.19 .dbd.NOR.sup.26 ; CH.dbd.CR.sup.27 CO.sub.2 R.sup.17 ; CH.sub.2 CHR.sup.27 CO.sub.2 R.sup.17 ; CO.sub.2 N.dbd.CR.sup.21 R.sup.22 ; NO.sub.2 ; CN; NHSO.sub.2 R.sup.23 ; NHSO.sub.2 NHR.sup.23 ; NR.sup.17 R.sup.28 ; NH.sub.2 or phenyl optionally substituted with R.sup.29 ; SCH.sub.3 ; OCHF.sub.2 ; halogen; CN or NO.sub.2 ; cyclopropyl; vinyl; C.sub.2 alkynyl; CN; C(O)R.sup.28 ; CO.sub.2 R.sup.28 ; C(O)NR.sup.28 R.sup.30 ; CR.sup.24 R.sup.25 CN; CR.sup.24 R.sup.25 C(O)R.sup.28 ; CR.sup.24 R.sup.25 CO.sub.2 R.sup.28 ; CR.sup.24 R.sup.25 C(O)NR.sup.28 R.sup.30 ; CHR.sup.24 OH; CHR.sup.24 OC(O)R.sup.28 or OCHR.sup.24 OC(O)NR.sup.28 R.sup.30 ; or when Q is Q-2 or Q-6, R.sup.14 and R.sup.15 can be taken together with the carbon to which they are attached to form C.dbd.O; -C.sub.6 alkoxyalkyl; C.sub.3 -C.sub.6 alkenyl; ##STR5## C.sub.3 -C.sub.6 alkynyl; R.sup.17 is C.sub.1 -C.sub.8 alkyl; C.sub.3 -C.sub.8 cycloalkyl; C.sub.3 -C.sub.8 alkenyl; C.sub.3 -C.sub.8 alkynyl; C.sub.1 -C.sub.8 haloalkyl; C.sub.2 -C.sub.8 alkoxyalkyl; C.sub.2 -C.sub.8 alkylthioalkyl; C.sub.2 -C.sub.8 alkylsulfinylalkyl; C.sub.2 -C.sub

REFERENCES:
patent: 3284447 (1966-11-01), Kusuda
patent: 3442892 (1969-05-01), Kusuda
patent: 4531964 (1985-07-01), Shimano et al.
patent: 4902335 (1990-02-01), Kume et al.
patent: 5053071 (1991-10-01), Semple
Weinreb et al, Tetrahedron Letters, 4171-4174 (1977).
Fischer, R. et al, Chemical Abstracts, 113, p. 705, Abstract No. 59178u (1990).
Hoffman-LaRoche, Chemical Abstracts, 69, p. 5545, Abstract No. 59272t (1968).

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