Chemistry: fertilizers – Processes and products – Forms or conditioning
Patent
1985-10-21
1989-02-21
Hollrah, Glennon H.
Chemistry: fertilizers
Processes and products
Forms or conditioning
548263, 548265, A01N 43653, C07D24912
Patent
active
048061450
DESCRIPTION:
BRIEF SUMMARY
The invention described in this application pertains to weed control in agriculture, horticulture, and other fields where there is a desire to control unwanted plant growth. More specifically, the present application describes certain herbicidal aryl triazolinones, compositions of them, methods of preparing them, and methods for preventing or destroying undesired plant growth by preemergence or postemergence application of the herbicidal compositions to the locus where control is desired. The present compounds may be used to effectively control a variety of bothh grassy and broadleaf plant species. The present invention is particularly useful in agriculture; a number of the compounds described herein show a selectivity favorable to certain crops at application levels which inhibit the growth of or destroy a variety of weeds.
One aspect of this invention relates to herbicidal compounds of the general formula ##STR2## wherein R.sup.2 is CHF.sub.2 or CH.sub.2 F; atoms), haloalkyl (e.g. of 1 to 5 carbon atoms such as difluoromethyl), alkoxyalkyl (e.g. of 2 to 6 carbon atoms such as methoxymethyl), cyanoalkyl (e.g. of 2 to 6 carbon atoms such as cyanomethyl), arylalkyl such as benzyl, alkylthio (e.g. of 1 to 3 carbon atoms such as methylthio) or the corresponding alkylsulfinyl or alkylsulfonyl, or alkylthioalkyl (e.g., of 1 to 3 carbon atoms independently with respect to each alkyl, such as methylthiomethyl) or the corresponding alkylsulfinylalkyl or alkylsulfonylalkyl. radical of the formula R.sup.8 OCH.sub.2 --, R.sup.8 SCH.sub.2 --, R.sup.8 SOCH.sub.2 -- or R.sup.8 SO.sub.2 CH.sub.2 -- where R.sup.8 is C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.5 alkenyl, or C.sub.3 -C.sub.5 alkynyl (e.g., CH.sub.3 OCH.sub.2 --, CH.sub.3 SCH.sub.2 --, CH.sub.2 .dbd.CHCH.sub.2 OCH.sub.2 --, CH.sub.2 .dbd.CHCH.sub.2 SCH.sub.2 --, CH.tbd.CCH.sub.2 OCH.sub.2 --, or CH.tbd.C--CH.sub.2 SCH.sub.2 --); R.sub.8 may also be phenyl (or phenyl substituted with e.g., halogen, alkyl, haloalkyl; see, e.g. compound 50, below). or --CH(CH.sub.3)--) or a haloalkylene radical (e.g. --CHF--) and R.sup.4 is an alkyl radical (e.g. CH.sub.3, C.sub.2 H.sub.5, C.sub.3 H.sub.7, C.sub.4 H.sub.9).
It is preferred that R.sup.1 be methyl and R.sup.2 be CHF.sub.2 and particularly that X be chlorine or (more preferably) fluorine and Y be chlorine.
Some of the compounds described above differ from otherwise similar compounds disclosed in U.S. Pat. No. 4,318,731 in that R.sup.2 of that patent is hydrogen, an alkyl group, or an alkenyl group. It has been found now that the replacement of an alkyl group by a CHF.sub.2 or CH.sub.2 F group yields compounds of much greater herbicidal activity. This is shown, for instance, in Table I below which gives the results of tests of the following two compounds, each applied at the rate of 0.125 kg. per hectare:
A. A compound in which R.sup.2 is CHF.sub.2 (compound No. 5 described below).
B. An otherwise identical compound in which R.sup.2 is C.sub.2 H.sub.5 (compound 62 of the aforesaid U.S. patent).
Representative compounds according to this aspect of the invention are given in Table 2 below.
The herbicidal esters of the aspect of the invention described above may be hydrolyzed to produce the corresponding acids, i.e., to compounds of the foregoing formula in which the substituent para to "X" is --OR.sup.3 COOH (i.e. carboxyalkoxy). I have found that these acids are also effective herbicides, somewhat less potent than the corresponding esters. The acids are also useful as intermediates for the preparation (as by esterification or amide formation) of other herbicidal compounds. The acids may be converted to their salts, such as their sodium, potassium, ammonium, calcium, magnesium, or mono, di or trialkylammonium salts, which may be used as herbicides.
Representative acids and salts are shown in Table 3 below.
In another aspect of this invention it has now been found that compounds of the following formula are effective herbicidal compounds: ##STR3## wherein R.sup.4 is a substituted alkyl group, an alkenyl group (e.g. allyl o
REFERENCES:
patent: 4318731 (1982-03-01), Kajioka et al.
Ertelt H. Robinson
FMC Corporation
Hollrah Glennon H.
Kennedy Robert M.
Morris P. L.
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