Herbicidally active phenylsubstituted 5-and 6-membered heterocyc

Details Herbicidally active phenylsubstituted 5-and 6-membered heterocyc Herbicidally active phenylsubstituted 5-and 6-membered heterocyc

1995-10-06

1999-01-05

Shah, Mukund J.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

504270, 504272, 504221, 504222, 504223, 504225, 504236, 504238, 504239, 504248, 504244, 504251, 504262, 504166, 504167, 504168, 504169, 504176, 504177, 504178, 504179, 504180, 548126, 548131, 5483001, 5483111, 548215, 548225, 5483147, 5482622, 5482632, 548543, 548544, 546 63, 546255, 5462681, 544111, 544106, 544 98, 544224, 544239, 544242, 544298, 544238, 544 582, A01N 4378, A01N 4336, C07D207273, C07D40306

Patent

active

058562737

DESCRIPTION:

BRIEF SUMMARY
This invention relates to chemical compounds useful as herbicides, to processes for preparing them, and to herbicidal compositions and processes utilising them.
Herbicidal compounds based upon carbonyl substituted nitrogen containing heterocyclic rings are known for example from British Patent No. 1345159 and DE OS 2212558.
The applicants have found a group of compounds which have a particular substituent pattern and which are active as herbicides.
According to the present invention there is provided a compound of formula (I): or hydrocarbyl; D completes a 5 or 6-membered non-aromatic heterocyclic ring which optionally contains additional heteroatoms selected from oxygen nitrogen or sulphur and which is optionally substituted by an optionally substituted lower hydrocarbyl group, or an optionally substituted heteroaryl group; R.sup.1 and R.sup.2 are each independently hydrogen, optionally substituted lower hydrocarbyl, or optionally substituted heteroaryl, or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached, form a heterocyclic ring;
Z represents halogen, optionally substituted lower hydrocarbyl, optionally substituted lower hydrocarbyloxy, optionally substituted lower hydrocarbylthio, hydrocarbylsulphinyl, or hydrocarbylsulphonyl, cyano, nitro, CHO, NHOH, ONR7'R7", SF.sub.5, CO(optionally substituted lower hydrocarbyl), acylamino, COOR.sup.7, SO.sub.2 NR.sup.8 R.sup.9, CONR.sup.10 R.sup.11, OR.sup.12 or NR.sup.13 R.sup.14 where R.sup.7, R.sup.7 ', R.sup.7 ", R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are independently H or lower hydrocarbyl; R.sup.12 is hydrogen, SO.sub.2 lower hydrocarbyl or COR.sup.15 ; R.sup.13 and R.sup.14 are independently lower hydrocarbyl, lower hydrocarbyloxy or a group R.sup.12 ; R.sup.15 is OR.sup.16, NR.sup.17 R.sup.18, hydrogen or lower hydrocarbyl; R.sup.16 is lower hydrocarbyl, R.sup.17 and R.sup.18 are independently hydrogen or lower hydrocarbyl provided that when there are two or more substituents Z, they may be the same or different; and completes a saturated heterocylic ring.
Particular examples of compounds of formula (I) are compounds of formula (II); wherein A, E, R.sup.1, R.sup.2, Z and m are as defined in relation to formula (I), and W, X and Y are independently selected from CR.sup.4 R.sup.5, NR.sup.6, O and S(O)p where p is 0, 1 or 2, R.sup.4, R.sup.5 and R.sup.6 are independently selected from hydrogen, optionally substituted lower hydrocarbyl, or optionally substituted heteroaryl, or R.sup.4 and R.sup.5 together with the carbon atom to which they are attached may form a carbocyclic ring; and n is 0 or 1 provided that no more than two of A, W, X and Y comprise heteroatoms in the ring; and when more than one of W, X or Y is CR.sup.4 R.sup.5, R.sup.4 and R.sup.5 may each be the same or different; and when more than one of W, X or Y is NR.sup.6, R.sup.6 may each be the same or different.
The expression lower hydrocarbyl in the foregoing definitions, whether the expression is used on its own or as part of a larger radical such as for example lower hydrocarbyloxy, is intended to include hydrocarbyl radicals of, for example, up to ten carbon atoms. Subclasses of such hydrocarbyl radicals include radicals with up to four, or up to six carbon atoms. The expression hydrocarbyl is intended to include within its scope aliphatic, alicyclic, and aromatic hydrocarbyl groups and combinations thereof. It thus includes, for example, alkyl, alkenyl, and alkynyl radicals, cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, and cyclohexyl radicals, the adamantyl radical and the phenyl radical.
When the lower hydrocarbyl group is substituted, the substituents may include, for example, halogen (i.e. chlorine, bromine, fluorine or iodine), cyano, nitro, amino, mono- and dialkylamino in which the alkyl groups have from 1 to 6 or more carbon atoms, acylamino, C.sub.1-6 alkoxy, C.sub.1-6 haloalkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, carboxy, carboxyamide in which the groups attached to the N atom may be hydrogen or opti

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