Heterocyclic compounds

Details Heterocyclic compounds Heterocyclic compounds

1989-05-19

1991-05-21

Shen, Cecilia

Chemistry: fertilizers

Processes and products

Forms or conditioning

540601, 544 60, 544123, 544232, 544283, 544284, 544285, 544295, 544310, 544311, 544312, 544313, A01N 4348, C07D23954

Patent

active

050172115

DESCRIPTION:

BRIEF SUMMARY
The present invention is concerned with heterocyclic compounds, namely 3-aryluracils of the general formula ##STR2## wherein R.sup.1 signifies hydrogen, C.sub.1-4 -alkyl, C.sub.1-4 -haloalkyl, C.sub.3 or 4 -alkenyl or C.sub.3 or 4 -alkynyl, C.sub.2-8 -alkenyl, C.sub.3-8 -alkynyl, C.sub.1-8 -haloalkyl, C.sub.1-8 -hydroxyalkyl, C.sub.1-4 -alkoxy-C.sub.1-8 -alkyl, C.sub.1-4 -alkylthio-C.sub.1-8 -alkyl, C.sub.1-4 -haloalkoxy-C.sub.1-8 -alkyl, C.sub.2-8 -cyanoalkyl, C.sub.1-8 -nitroalkyl, C.sub.2-9 -carboxyalkyl, C.sub.2-5 -alkoxycarbonyl-C.sub.1-8 -alkyl, C.sub.1-4 -alkylsulphonyl-C.sub.1-8 -alkyl, di(C.sub.1-4 -alkyl)-phosphono-C.sub.1-8 -alkyl, C.sub.3-8 -cycloalkyl, C.sub.1-8 -alkoxy or phenyl or phenyl-C.sub.1-4 -alkyl optionally substituted with halogen, hydroxy, C.sub.1-4 -alkyl, C.sub.1-4 -haloalkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylthio, C.sub.1-4 -haloalkoxy, cyano, nitro, carboxy and/or C.sub.2-5 -alkoxycarbonyl, whereby this optionally substituted phenyl can have a fused, saturated, carbocyclic five- to seven-membered ring or a fused, saturated, heterocyclic five- to seven-membered ring containing 1 or 2 oxygen atoms, whereby R.sup.2 and R.sup.3 cannot both stand for C.sub.1-8 -alkoxy, or attached signify a four- to seven-membered heterocyclic ring which is optionally mono- or multiply substituted with C.sub.1-6 -alkyl and which, in addition to the nitrogen atom, can also have in the ring an oxygen atom, a sulphur atom and/or a second nitrogen atom, C.sub.1-4 -haloalkyl, also C.sub.1-4 -haloalkyl, or corresponding enol ethers of those compounds of formula I in which R.sup.1 signifies C.sub.1-4 -alkyl, C.sub.3 or 4 -alkenyl or C.sub.3 or 4 -alkynyl, R.sup.6 signifies hydrogen, halogen or C.sub.1-4 -alkyl and R.sup.7 signifies C.sub.1-4 -haloalkyl, as well as salts of those compounds of formula I or enol ethers in which R.sup.1 and/or R.sup.2 signify hydrogen.
The above-mentioned enol ethers are thus the compounds of the formula ##STR3## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the significances given above and R.sup.1' signifies C.sub.1-4 -alkyl, C.sub.3 or 4 -alkenyl or C.sub.3 or 4 -alkynyl, R.sup.6' signifies hydrogen, halogen or C.sub.1-4 -alkyl and R.sup.7' signifies C.sub.1-4 -haloalkyl. Their salts are salts of those enol ethers Ia in which R.sup.2 signifies hydrogen.
The compounds in accordance with the invention have herbicidal activity and are suitable as active substances of weed control compositions. Accordingly, the invention also embraces weed control compositions which contain compounds in accordance with the invention as the active substance, a process for the manufacture of these compounds as well as the use of the compounds or compositions for the control of weeds.
In formula I above "halogen" embraces fluorine, chlorine, bromine and iodine. The alkyl, alkenyl and alkynyl residues can be straight-chain or branched, whereby this also applies to the alkyl part or the alkyl parts of the haloalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, haloalkoxyalkyl, cyanoalkyl, nitroalkyl, carboxyalkyl, alkoxycarbonyl, alkylsulphonylalkyl, dialkylphosphonoalkyl, alkoxy, haloalkoxy and phenylalkyl groups. A haloalkyl or haloalkoxy group can have one or more (similar or different) halogen atoms. Likewise, a substituted phenyl or phenylalkyl group can have one or more of the aforementioned substituents which can be the same or different. Under "lower alkyl" mentioned hereinafter there is to be understood especially C.sub.1-6 -alkyl.
Examples of bicyclic groups which R.sup.2 and R.sup.3 can signify are 1,3-benzodioxol-5-yl and 1,3-benzodioxan-6-yl.
Examples of four- to seven-membered heterocyclic rings which NR.sup.2 R.sup.3 can form are pyrrolidino, piperidino, hexahydroazepino, morpholino, thiomorpholino, piperazino and 4-methylpiperazino.
The salts of the compounds of formula I and of their enol ethers are especially alkali metal salts, e.g. sodium and potassium salts; alkaline earth metal salts, e.g. calcium and magnesium salts; ammonium salts, i.e. unsubstituted ammonium salts and m

REFERENCES:
patent: 3235357 (1966-02-01), Loux
patent: 3235360 (1966-02-01), Soboczenski
patent: 3235363 (1966-02-01), Luckenbaugh et al.
patent: 3291592 (1966-12-01), Evans
patent: 3346207 (1967-10-01), Jenny
patent: 3352862 (1967-11-01), Loux
patent: 3360520 (1967-12-01), Luckenbaugh et al.
patent: 4746352 (1988-05-01), Wenger et al.
patent: 4760163 (1988-07-01), Wenger et al.
Wenger et al., CA 106-50241g (1987).
Wenger et al., Chem. Abst. 109-231048g (1988).
Wenger et al., Chem. Abst. 109-73464h (1988).
Wenger et al., Chem. Abst. 111-134187k (1989).

Affiliated with

Also associated with

Rating

Heterocyclic compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Heterocyclic compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Heterocyclic compounds will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-235319