3-aryluracil derivatives and their use as herbicides

Details 3-aryluracil derivatives and their use as herbicides 3-aryluracil derivatives and their use as herbicides

1994-12-16

1997-02-04

Ford, John M.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

544230, 544311, 544312, 544310, 544313, 544314, 544295, 544296, C07D23954, C07D23952, A01N 4354

Patent

active

055997716

DESCRIPTION:

BRIEF SUMMARY
This is a U.S. national stage application filed under 35 USC 371 of international application PCT/EP94/01109, filed Apr. 11, 1994.
The present invention relates to novel, herbicidally active 3-aryluracil derivatives, to processes for their preparation, to compositions comprising those compounds, and to their use in controlling weeds, especially in crops of useful plants, or in inhibiting plant growth.
3-Aryluracils having herbicidal action are known and are described, for example, in WO 91/00278 and EP-A-0 195 346.
Novel 3-aryluracil derivatives having herbicidal and growth-inhibiting properties have now been found.
The present invention accordingly relates to compounds of formula I ##STR3## wherein W is a group of the formula ##STR4## wherein the bond to the ring nitrogen atom is made via the carbon atom; R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 - or C.sub.4 -alkenyl or C.sub.3 - or C.sub.4 -alkynyl; -C.sub.8 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy-C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.6 alkyl, aryl, aryl-C.sub.1 -C.sub.4 alkyl, heteroaryl or heteroaryl-C.sub.1 -C.sub.4 alkyl; or form a 3-, 4-, 5- or 6-membered ring which is unsubstituted or mono- or poly-substituted by C.sub.1 -C.sub.4 alkyl and which may contain --O--, --S-- or --N(R.sub.10)-- as hetero atom; nitro-C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl-C.sub.1 -C.sub.6 alkyl, aryl, aryl-C.sub.1 -C.sub.4 alkyl, heteroaryl, heteroaryl-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.6 alkyl-carbonyl-C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy-C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy-carbonyl-C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 -alkenyloxy-carbonyl-C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkylthio-C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 -dialkylamino-C.sub.2 -C.sub.6 alkyl, oxetanyl or C.sub.1 -C.sub.6 isoalkylideneaminooxy-C.sub.1 -C.sub.4 alkyl; - or C.sub.4 -alkynyl; and compounds of formula I.
In the formulae I of the 3-aryluracils according to the invention, halogen in the definitions of radicals R.sub.2 and R.sub.4 is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine and bromine.
The alkyl, alkenyl and alkynyl radicals R.sub.1 and R.sub.4 to R.sub.10 may be straight-chain or branched, and this applies also to the alkyl moiety of haloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkenyloxycarbonylalkyl, arylalkyl, heteroarylalkyl, alkylthioalkyl, dialkylaminoalkyl, nitro and cyanoalkyl groups. Examples of such alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, preferably alkyl groups having 1, 2 or 3 carbon atoms; examples of alkenyl radicals that may be mentioned are allyl, 1-methylallyl, methallyl or but-2-en-1-yl, preferably alkenyl radicals having a chain length of 3 or 4 carbon atoms; and examples of alkynyl radicals that may be mentioned are propargyl, but-2-yn-1-yl, 2-methylbutyn-2-yl, but-3-yn-2-yl and pent-4-yn-1-yl, preferably alkynyl radicals having a chain length of 3 or 4 carbon atoms.
The cycloalkyl radical coming into consideration as a substituent in the definitions of R.sub.6, R.sub.7 and R.sub.8 is, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
Haloalkyl groups that come into consideration are alkyl groups mono- or poly-substituted, especially mono- to tri-substituted, by halogen (identical or different), the individual meanings of halogen being iodine and especially fluorine, chlorine and bromine, for example trifluoromethyl, 2,2,2-trifluoroethyl or 2-chloro- or 2-bromo-ethyl.
Alkoxyalkyl in the definitions of the radicals R.sub.6, R.sub.7 and R.sub.8 is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, methoxypropyl or ethoxypropyl.
Aryl in the definition of the radi

REFERENCES:
patent: 4746352 (1988-05-01), Wenger et al.
patent: 4760163 (1988-07-01), Wenger et al.
patent: 5183492 (1993-02-01), Suchy et al.
patent: 5266554 (1993-11-01), Suchy et al.
patent: 5336663 (1994-08-01), Wenger et al.
Ruchardt et al., Chem. Ber. 108:3224-3242 (1975).
Bodanszky et al., Side Reactions in Peptide Synthesis, Synthesis, pp. 333-356 (May, 1981).
Fahrenholtz et al., Journal of Medicinal Chemistry, vol. 17, No. 3, 337-342 (1974).
Miyake et al., Synthetic Communications, 14(4), pp. 353-362 (1984).
Miyake et al., Chemistry, Letters, pp. 123-236 (1985).
Patai, The Chemistry of Carboxylic Acids and Esters, pp. 1-3, Interscience Publishers, London (1969).
Greene et al., Protective Groups in Organic Synthesis, 2nd Ed., p. 1, A. Wiley-Interscience Publications (1991).
Klintz et al, Chemical Abstracts, vol. 119, embry 117271 (1993).
Houben-Weyl, Methoden Der Organischen Chemie, vol. VIII, 1952, pp. 508-513.

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