Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1996-11-12
1998-03-10
Powers, Fiona T.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
548544, A01N 4336, C07D20727
Patent
active
057261296
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/GB95/01223 filed May 26 1995.
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):
Wherein 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; R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently H or C.sub.1-4 alkyl; Z represents halogen, optionally substituted lower hydrocarbyl, optionally substituted lower hydrocarbyloxy, optionally substituted lower hydrocarbylthio, hydrocarbylsulphinyl, or hydrocarbylsulphonyl, cyano, nitro, CHO, NHOH, ONR.sup.7' R.sup.7", 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
m is 0 or an integer from 1 to 5.
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), hydroxy, SO.sub.2 NR.sup.a R.sup.b (where R.sup.a and R.sup.b are independently H or C.sub.1-6 alkyl), 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 optionally substituted lower hydrocarbyl; alkoxy carbonyl wherein the alkoxy group may have from 1 to 6 or more carbon atoms, and aryl such as phenyl.
The expression heteroaryl in the foregoing definitions is intended to include such radicals as pyridyl, pyrimidyl, triazinyl, thienyl, furyl, and thiazolyl. When the heteroaryl radical is substituted, the substituents may include those recited above for substituted lower hydrocarbyl.
Particular examples of values for R.sup.1 and R.sup.2 include hydrogen, methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, t-butyl, n-pentyl and its isomers such as C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3, n-hexyl and its isomers, n-heptyl and its isomers, C(CH.sub.3).sub.2 C.tbd.CH, C(CH.sub.3)CH.tbd.CH.sub.2, C(CH.sub.3).sub.2 CN, alpha-methyl benzyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, 1-methyl cyclohexyl, 1-methyl-cyc
REFERENCES:
patent: 3818032 (1974-06-01), Moser et al.
patent: 4956006 (1990-09-01), Woolard
patent: 5108482 (1992-04-01), Lang et al.
Barber Richard Anthony
Barnes Nigel John
Powers Fiona T.
Snyder Joseph R.
Zeneca Limited
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