Chemistry: fertilizers – Processes and products – Forms or conditioning
Patent
1989-06-16
1991-08-20
Shen, Cecilia
Chemistry: fertilizers
Processes and products
Forms or conditioning
544309, 544311, 544312, 544313, A01N 4348, C07D23902
Patent
active
050411560
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.2-5 -alkenyl or C.sub.3-5 -alkynyl, C.sub.1-4 -haloalkyl, also C.sub.1-4 -haloalkyl hydrogen) or a group (c) or (d) (where R.sup.1 stands for hydrogen) ##STR3## wherein R.sup.6 signifies hydrogen or C.sub.1-4 -alkyl, -alkoxycarbonyl or C.sub.2-7 -alkoxycarbonyl-C.sub.1-4 -alkyl, -alkoxy-C.sub.1-4 -alkyl, C.sub.2-7 -alkoxycarbonyl-C.sub.1-4 -alkyl, di (C.sub.2-7 -alkoxycarbonyl)-C.sub.1-4 -alkyl, C.sub.3-6 -cycloalkyl, C.sub.1-6 -alkoxy, C.sub.1-6 -alkylthio, C.sub.2-7 -alkanoyl, C.sub.2-7 -alkoxycarbonyl, phenyl or 2-furyl, attached signify a cyclopentane or cyclohexane ring optionally substituted with 1 to 3 C.sub.1-4 -alkyl groups, C.sub.3-5 -haloalkynyl, C.sub.3-8 -alkynyl. C.sub.2-6 -alkoxyalkyl or C.sub.3-8 -cycloalkyl, phenyl or benzyl optionally those compounds of formula I in which R.sup.1 signifies C.sub.1-4 -alkyl C.sub.2-5 -alkenyl or C.sub.3-5 -alkynyl and Q signifies a group (b), (c) or (d) as well as salts of those compounds of formula I and of the enol ethers in which R.sup.1 and/or R.sup.13 signifies hydrogen.
Under the above-mentioned enol ethers there are thus to be understood the compounds of the formula ##STR4## and also the compounds of the formula ##STR5## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the significances given above, R signifies C.sub.1-4 -alkyl, C.sub.2-5 -alkenyl or C.sub.3-5 -alkynyl and Q' signifies a group (b). (c) or (d). Their salts are salts of those enol ethers Ia and Ib in which Q' signifies mercapto, i.e. group (d) in which signifies hydrogen.
The compounds in accordance with the invention. i.e. the compounds of formula I and their enol ethers and the salts thereof. 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 and this also applies to the or each alkyl, alkenyl or alkynyl part of the haloalkyl, alkylthio, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxyalkyl, dialkoxycarbonylalkyl, alkoxy, alkanoyl, haloalkenyl and haloalkynyl qroups. A haloalkyl, haloalkenyl or haloalkynyl group can have one or more (similar or different) halogen atoms. Likewise, a cyclopentyl, cyclohexyl, C.sub.3-8 -cycloalkyl, phenyl or benzyl group multiply substituted with C.sub.1-4 -alkyl groups can have the same or different alkyl substituents.
The salts of the compounds of formula I and of the enol ethers of formulae Ia and Ib 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 I and in their enol ethers Ia and Ib means that the compounds can occur in optically isomeric forms. Geometric isomerism can also occur when an aliphatic C.dbd.C or C.dbd.N double bond is present. Moreover. in those compounds of formula I in which R.sup.1 signifies hydrogen keto-enol tautomerism [--NH--CO--.revreaction.--N=C(OH)--] can occur. Formula I is intended to embrace all of these possible isomeric forms as well as mixtures thereof.
When R.sup.1 or R.sup.13 signifies alkenyl or alkynyl, this residue is preferably allyl or propargyl, respectively. A haloalkyl group which may be present is preferably C.sub.1-4 -fluoroalkyl. especially difluoromethyl in the case of R.sup.1 and trifluoromethyl o
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patent: 3137698 (1964-06-01), Pfister
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patent: 4812164 (1989-03-01), Wenger et al.
patent: 4859229 (1989-08-01), Wenger et al.
patent: 4927451 (1990-05-01), Brouwer et al.
March, Advanced Organic Chemistry, 3rd Edition, pp. 348-352.
Suchy Milos
Wenger Jean
Winternitz Paul
Zeller Martin
Ciba-Geigy Corporation
McC. Roberts Edward
Shen Cecilia
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