Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1993-09-03
1995-02-28
Ford, John M.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
544320, A01N 4354, C07D23946
Patent
active
053937341
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
This invention relates to a certain herbicidal sulfonamide or sulfonylurea compound, an agriculturally suitable composition thereof and a method for its use as a general or selective preemergent or postemergent herbicide.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
The "sulfonylurea" herbicides are an extremely potent class of herbicices discovered within the last few years which generally consist of a sulfonylurea bridge, --SO.sub.2 NHCONH--, linking two aromatic or heteroaromatic rings.
WO 88/04297 discloses herbicidal pyridinesulfonylureas of the formula ##STR1## wherein
J is, among others, ##STR2##
R.sub.1 is R.sub.f or R.sub.g ;
R.sub.g is, among others, C.sub.1 -C.sub.3 haloalkyl; and
R.sub.2 is, among others, CO.sub.2 R.sub.9.
Although the compound of the invention is within the above generic scope, it is not disclosed therein.
EP-A-327,251 discloses pyridinesulfonylureas of the formula ##STR3## wherein
R is C.sub.1 -C.sub.3 alkyl; and
R.sub.1 is C.sub.1 -C.sub.2 fluoralkyl and their use for controlling blackgrass.
EP-A-232,067 discloses 3-carboxamide pyridinesulfonylureas. However, this reference does not disclose the instant compound or the blackgrass utility therein.
EP-A-237,292 discloses 3-carboxamide pyridinesulfonylureas. However, this reference does not disclose the instant compound or the blackgrass utility therein.
SUMMARY OF THE INVENTION
The present invention is directed to a compound of Formula I ##STR4## and its agriculturally suitable salts, hydrates and complexes with C.sub.1 -C.sub.4 alcohols such as methanol, ethanol, pyranol, isopropanol and the different butyl alcohols.
The compound of the invention is highly active as a preemergent and/or postemergent herbicide for the control of blackgrass. It is especially useful for the selective control of blackgrass in cereal crops.
This invention also comprises a novel compound of Formula II which is useful as an intermediate to the compound of Formula I
DETAILED DESCRIPTION OF THE INVENTION
Synthesis
The compound of Formula I can be synthesized by one or more of the general methods described in U.S. Pat. No. 4,774,337 and U.S. Pat. No. 4,456,469: ##STR6## where J and A are as defined below. Alternatively, the compounds of Formula I can be synthesized by the reactions shown in Equations 1a and 1b. The reaction of sulfonamide II with the phenyl ester of the appropriate carbamic acid IIIa in the presence of various bases such as a tertiary amine base, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) for example, is shown in Equation 1a.
The reaction of sulfonamide II with the phenyl ester of the appropriate carbamic acid IIIa in the presence of various bases such as a tertiary amine base, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) for example, is shown in Equation 1a. ##STR7##
The reaction shown in Equation 1a is best carried out at 25.degree. C. in a solvent such as, but not limited to, dioxane, tetrahydrofuran, dimethylformamide, dimethylacetamide or acetonitrile for 0.5-24 hours under an inert atmosphere as described in European Patent Application No. 70,804 (published Jan. 26, 1983). The addition of a base is advantageous. Bases especially suitable are 1,5-diazabicyclo[4,3,0]non-5-ene (DBN), 1,5-diazabicyclo[5,4,0]undec-5-ene (DBU) or triethylamine. The des
REFERENCES:
patent: 4435206 (1984-03-01), Levitt
Andrea Tarig A.
Liang Paul H.
E. I. Du Pont de Nemours and Company
Ford John M.
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