Chemistry: fertilizers – Processes and products – Forms or conditioning
Patent
1990-09-14
1992-02-25
Ford, John M.
Chemistry: fertilizers
Processes and products
Forms or conditioning
544208, C07D25152, A01N 4370
Patent
active
050909932
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
U.S. Pat. No. 4,744,816, issued May 17, 1988, and EP-A-164,269, published on Dec. 11, 1985, disclose herbicidal sulfonylureas of the formula ##STR1## wherein R.sub.1 is, inter alia, CO.sub.2 R.sub.10, etc.; OC.sub.2 H.sub.5, SCH.sub.3 or SC.sub.2 H.sub.5 ; CH.sub.2 Cl, CH.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 C.tbd.CH; CN;
South African Application No. 84/2245, published 9/28/84, discloses herbicidal sulfonylureas of the formula ##STR2## wherein A is C.sub.1 -C.sub.6 haloalkyl C.sub.2 -C.sub.4 haloalkoxy, NR.sub.12 R.sub.13, etc.; haloalkoxy, C.sub.2 -C.sub.6 alkoxyalkoxy, etc.; and
While these two references generically disclose some of the compounds of the instant invention, there is no specific mention of the instant compounds or their utility in sugar beets.
U.S Pat. No. 4,618,363 discloses herbicidal sulfonylureas of the formula ##STR3## wherein R.sub.1 is H, halogen, NO.sub.2, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 --C.sub.4 alkoxycarbonyl; -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkenyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxycarbonyl, --NR.sub.45 R.sub.46, --SO.sub.3 H or --SO2NR.sub.47 R.sub.48 ; unsubstituted by 1 to 3 halogen atoms;
While this reference generically discloses some of the compounds of the instant invention, there is no specific mention of the instant compounds or their utility in sugar beets.
SUMMARY OF THE INVENTION
This invention comprises novel compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as preemergence and/or postemergence herbicides or plant growth regulants. ##STR4## wherein R is C.sub.1 -C.sub.4 alkyl, CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 C.tbd.CH, cyclopropylmethyl or CH.sub.2 CH.sub.2 R.sub.2 ; CH.sub.2 CH.sub.3, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, phenylthio or NR.sub.3 R.sub.4 ; halogen; R.sub.1 is OCH.sub.2 CH.sub.3 or CH.sub.2 OCH.sub.3, then R is other than CH.sub.3 ;
In the above definitions, the term "alkyl" includes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers.
Alkoxy includes methoxy and ethoxy.
Alkylthio includes methylthio and ethylthio.
The term "halogen," either alone or in compound words such as "haloalkyl," means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CF.sub.3, CH.sub.2 CH.sub.2 F, CF.sub.2 CF.sub.3 and CH.sub.2 CHFCl.
The total number of carbon atoms in a substituent group is indicated by the C.sub.i -C.sub.j prefix where i and j are numbers from 1 to 4. For example, C.sub.1 -C.sub.4 alkyl would designate methyl, ethyl and the different propyl and butyl isomers; C.sub.1 -C.sub.2 alkylthio would designate methylthio and ethylthio; C.sub.1 -C.sub.2 alkoxy would designate methoxy and ethoxy.
Preferred for reasons of their higher herbicidal activity, greater safety to sugar beets and/or more favorable ease of synthesis are:
1. Compounds of Formula I wherein
2. Compounds of Formula I wherein
3. Compounds of Preferred 1 wherein
4. Compounds of Preferred 1 wherein
Specifically preferred for reasons of highest herbicidal activity, greatest safety to sugar beets and/or most favorable ease of synthesis are: -1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate, melting point 134-142.degree. C.; and -1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate, melting point 150-160.degree. C.
DETAILED DESCRIPTION OF THE INVENTION
Synthesis
The following discussion represents a general outline for the preparation of the compounds of this invention. All of the syntheses described below are multistep with one or more methods being taught for each step. This allows for a wide variety of possible synthetic pathways to prepare a particular compound of Formula I. The pro
E. I. du Pont de Nemours & Company
Ford John M.
Parrish John A.
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