6-Fluoro-3,5-dihalo-2-pyridyloxy compounds

Details 6-Fluoro-3,5-dihalo-2-pyridyloxy compounds 6-Fluoro-3,5-dihalo-2-pyridyloxy compounds

1977-04-11

1979-12-25

Raymond, Richard

Chemistry: fertilizers

Processes and products

Forms or conditioning

546 5, 546291, 546302, A01N 922, C07D21389

Patent

active

041803957

ABSTRACT:
Compounds are prepared which correspond to the formula ##STR1## wherein X represents chloro, bromo or iodo; R' represents hydrogen or methyl and R represents carboxy (--COOH), the alkyl esters thereof (--COOR.sup.6 wherein R.sup.6 represents alkyl of 1 to 8 carbon atoms, (2-alkoxyethoxy)carbonyl (--COOCH.sub.2 CH.sub.2 OR.sup.2) or (1-methyl-2-alkoxyethoxy)carbonyl ##STR2## wherein R.sup.2 represents alkyl of 1 to 4 carbon atoms) or the metal salts thereof (--COOMe wherein Me represents ammonium or substituted ammonium ion (N.sup.+ H(R.sup.6).sub.3 wherein each R.sup.6 independently represents hydrogen, alkyl of 1 to 4 carbon atoms or hydroxyalkyl of 2 to 3 carbon atoms), alkali metal, alkaline earth metal, aluminum or a transition group metal); alkanoyloxymethyl (--CH.sub.2 OCOR.sup.2); (2,2-dichloropropionyloxy)methyl (--CH.sub.2 OCOC(Cl).sub.2 CH.sub.3); alkoxymethyl (--CH.sub.2 OR.sup.2); phenoxymethyl (--CH.sub.2 O.phi.); (2-alkoxyethoxy)methyl (--CH.sub.2 OCH.sub.2 CH.sub.2 OR.sup.2); hydroxyalkyl (--R.sup.3 OH wherein R.sup.3 represents alkylene of from 1 to 6 carbon atoms); 3-hydroxy-1-propenyl (--CH.dbd.CHCH.sub.2 OH); 1,2-dihydroxyethyl ##STR3## 1-(2-hydroxyethoxy)methyl (--CH.sub.2 --O--CH.sub.2 CH.sub.2 OH); (2-(2-hydroxyethoxy)ethoxy)methyl (--CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OH); carbamoyl (--CONR.sup.4 R.sup.4 wherein each R.sup.4 independently represents hydrogen or alkyl of 1 to 8 carbon atoms); (carboxymethyl)carbamoyl (--CONHCH.sub.2 COOH); (2-hydroxyethyl)-carbamoyl (--CONR.sup.4 CH.sub.2 CH.sub.2 OH); or (carbamoyloxy)methyl (--CH.sub.2 OCONHR.sup.5 wherein R.sup.5 is alkyl of 1 to 4 carbon atoms or phenyl). These compounds have been found to be effective pre- and post-emergent herbicides and some as intermediates in preparing compounds which are effective pre- and post-emergent herbicides and as active agents in compositions used as herbicides.

REFERENCES:
patent: 3206358 (1965-09-01), Stevenson
patent: 3234002 (1966-02-01), Weed
patent: 3249419 (1966-05-01), Martin
patent: 3544677 (1970-12-01), Lapham et al.
patent: 3609158 (1971-09-01), Torba
patent: 3766195 (1973-10-01), Bimber et al.
patent: 3814774 (1974-06-01), Whitaker et al.
patent: 3883541 (1975-05-01), Hamilton
patent: 3923822 (1975-12-01), Domenico
patent: 4066438 (1978-01-01), Johnston et al.
Cava et al., J. Org. Chem. vol. 23 (1614-1616) (1958).

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