Heterocyclic compounds

Details Heterocyclic compounds Heterocyclic compounds

1989-02-14

1990-07-17

Shen, Cecilia

Chemistry: fertilizers

Processes and products

Forms or conditioning

71 90, 544209, 544310, 544311, 544312, 544313, 544314, A01N 4354, A01N 4310, C07D23954

Patent

active

049419099

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.3 or 4 -alkynyl, C.sub.3 or 4 -alkynyl or C.sub.1-4 -haloalkyl,
R.sup.2 signifies a group ##STR3## or, where R.sup.1 signifies haloalkyl, also hydrogen, C.sub.1-8 -alkyl, C.sub.2-8 -alkenyl, C.sub.2-8 -alkynyl or C.sub.2-8 -alkoxyalkyl,
R.sup.3 signifies halogen or cyano,
R.sup.4 signifies hydrogen or halogen,
R.sup.5 signifies hydrogen, fluorine or C.sub.1-4 -alkyl,
R.sup.6 signifies C.sub.1-4 -alkyl or C.sub.1-4 -haloalkyl, the symbols R.sup.7 each independently signify hydrogen or C.sub.1-3 -alkyl and
n signifies 0, 1 or 2, and
Q signifies a saturated three- to seven-membered carbocyclic or heterocyclic residue which is optionally substituted with one or more C.sub.1-4 -alkyl residues, whereby the heterocyclic residue has 1 or 2 hetero atoms selected from oxygen and sulphur and optionally a keto function in the ring, or
Q signifies a phenyl residue which is optionally mono- or multiply-substituted with halogen, C.sub.1-4 -alkyl, C.sub.1-4 -haloalkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylthio, nitro and/or cyano and which additionally can contain a fused, saturated, carbocyclic or heterocyclic five- to seven-membered ring, whereby the heterocycle has 1 or 2 oxygen atoms in the ring, R.sup.1 is different from hydrogen or C.sub.1-4 -haloalkyl as well as salts of those compounds of formula I in which R.sup.1 or R.sup.2 signifies hydrogen.
Under the aforementioned enol ethers there are thus to be understood the compounds of the formula ##STR4## wherein R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, n and Q 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.
The compounds in accordance with the invention have herbicidal activity and are suitable as active substances of weed control compositions. Accordingly, the invention also includes 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 and this also applies to the alkyl part of the haloalkyl, alkoxy and alkylthio groups. A haloalkyl group can have one or more (similar or different) halogen atoms.
The following are examples of residues Q: Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 2-oxiranyl, 2-methyl-2-oxiranyl, 3-oxetanyl, 3-methyl-3-oxetanyl, 3-ethyl-3-oxetanyl, 2-tetrahydrofuryl, 3-tetrahydrofuryl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 3-methyl-3-thietanyl, 3-tetrahydrothienyl, 1,3-dioxolan-5-yl, 1,3-dioxan-5-yl, 1-oxo-4-tetrahydrothiopyranyl, phenyl, 1,3-benzodioxol-5-yl and 1,3-benzodioxan-6-yl.
The salts of the compounds of formula I 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 mono- or multiply-substituted ammonium salts, e.g. triethylammonium and methylammonium salts, as well as salts with other organic bases, e.g. with pyridine.
The presence of at least one asymmetric carbon atom in the compounds of formula I means that the compounds can occur in optically isomeric forms. Geometric isomerism can also occur when an aliphatic C.dbd.C double bond is present. Formula I is intended to embrace all of these possible isomeric forms as well as mixtures thereof.
An interesting group of compounds in accordance with the invention comprises those compounds of formula I in which R.sup.1 signifies hydrogen C.sub.1-4 -alkyl, C.sub.3 or 4 -alkenyl or C.sub.3 or 4 -alkynyl and the enol ethers and salts of these compounds. A further interesting group of compounds in accordance with the invention comprises those compoun

REFERENCES:
patent: 4746352 (1988-05-01), Wenger et al.
Wenger et al, CA 106-50241g (1987), "Aryluracils and Their Use as Herbicides".
Wenger et al, CA 109-231048g (1988), "Preparation of Herbicidal 3-Aryluracil Enol Ethers".
Wenger et al., CA 110-231655y (1989), "Preparation of Pyrimidinylbenzoates as Herbicides".

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