CA1336362C - Selective herbicide for use in potatoes and tomatoes - Google Patents

Abstract

(N-[[4,6-dimethoxy-2-pyrimidinyl)amino]-carbonyl]-3-(ethylsulfonyl)-2-pyridine-sulfonamide, alternatively named N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide) and the agriculturally suitable salts thereof are particularly effective as a preemergence and/or postemergence herbicide or plant growth regulant for the selective control of undesired vegetation in a crop of potatoes or tomatoes.

Description

TITLE
SELECTIVE HERBICIDE FOR USE IN
POTATOES AND TOMATOES
BACKGROUND OF T~E DISCLOSURE
A designated compound is particularly effective for the selective control of undesired vegetation in a crop of potatoes or tomatoes.
WO 88/04297, published June 16, 1988, broadly discloses, but does not claim, the specific utility of the compound of Formula I in potato and tomato crops.
EP-A-13,480 discloses herbicidal sulfonamides of the formula R2 ~ 2 N- C - N- R

wherein Rl is H, Cl, Br, F, Cl-C4 alkyl, Cl-C4 alkoxy, Cl-C4 alkylthio, NO2 or CO2R5.
U.S. 4,487,626 discloses herbicidal sulfonamides of the formula 2 i 3~3~
.

Z ~

wherein H ~ ~

R2 is H, F, Cl, Br, Cl-C4 alkyl, Cl-C4 alkoxy~ NO2, C2R15~ S(O)mR16 SO2NR18Rlg or SO2N(OCH3)CH3.
U.S. 4,421,550 discloses herbicidal sulfonamides of the formula R~
N--N
R~ ~2Z

wherein Z ~ ~ R~ 7~ or R~ 7 ~ ; nnd R16 is H, Cl-C~ alkyl, Cl-C4 alko~cy, F, Cl, Br, CF3, C02R2o, S02NR~ S02N(OCH3)CH3 or 5(0) nR

EP-A-84, 224 disclo~e~ ~erbicidal 3ulfonamide-~o~ the rorm~la B
, . , ~ 4 1 336362 wt N ~
AS02 NHC~J --<;O z R2 t ~
y wherein A ~- R~-~ ~ or R~7~ : and 16 is ~ Cl-C4 alkyl, C~-C4 alko~y, F, Cl, Br, CF3, C02Rg, 502NRloRl1~ S02N(OCH3)CH3 or 5()nR13 EP-A-12~,846 discloses herbicidal sulfonamides of the formula w x JSO2N~- N~gZ
R ~J

~herein ~ ~ or f9 _ R is Cl, SOzCH3, S02N(CH3)2~ OCH3~ 2 N(CH3)2-EP-A-155,767 discloses herbicidal sulfonamides of the formula O N~
JS2NHCN ~ J~
R N~

wherein J i 8 ~ or ~ ; and 5 is H, CH3, Cl, Br, C2R15~ C()NR16R17' S2NR16R17~ S02N(OCH3)CH3~ S02R18 or N02 U.S. 4,549,898 discloses herbicidal sulfonamides of the formula RR3 ~ " ~

So2NHCNH ~ O E
N ~
Y-CHFz wherein R2 is H~ Cl-C3 alkyl, Cl-C3 haloalkyl, halogen, NO2, Cl-C3 alkoxy, C(W)R8, SO2NR6R7~ S()n~
Cl-C3 alkyl or C(O)Rg;
R3 is H, halogen, Cl-C3 alkyl, OCH3, NO2 or CF3;
R5 is H, NO2, F, Cl, Br, CH3, CF3, S(O)nCl-C3 alkyl, C(O)Cl-C4 alkoxy or Cl-C3 alkoxy;
Y is O or S.
U.S. 4,579,583 discloses herbicidal sulfonamides of the formula R~ ~ 2 NHC NH~E

wherein A is a C3-C6 alkynyl radical, a Cl-C6 alkyl radical which is substituted by halogen, Cl-C4 alkoxy, Cl-C4 alkylthio, Cl-C4 alkylsulfinyl, Cl-C4 alkylsulfonyl, Cl-C4 haloalkoxy, Cl-C4 haloalkylthio, Cl-C4 haloalkylsulfinyl, Cl-C4 haloalkylsulfonyl or is a C2-C4 alkenyl radical which is unsubstituted or substituted as for Cl-C6 alkyl, or is a phenyl radical which is unsubstituted or substituted by halogen, cyano, nitro, Cl-C4 alkyl, Cl-C4 haloalkyl, an -X-Cl-C4 alkyl, Cl-C4 alkoxycarbonyl, amino, mono- or di(Cl-C4 alkyl)amino, carbamoyl, mono- or di-(Cl-C4alkyl)carbamoyl, sulfamoyl, mono- or di-(Cl-C4 alkyl)carbamoyl, sulfamoyl, mono- or di-(Cl-C4 alkyl)sulfamoyl radical;
XA may form a radical NR6R7;
Rl is hydrogen, halogen, Cl-C4 alkyl, Cl-C4 alkoxy, Cl-C4 haloalkyl, Cl-C4 haloalkoxy, C2-C5 alkoxyalkoxy, Cl-C5 alkylthio, Cl-C5 alkylsulfinyl or Cl-C5 alkylsulfonyl; and X is 0, S, SO or S02.
U.S. 4,518,776 discloses a process for the preparation of herbicidal sulfonamides of the formula Rz ~ Z ~( ~

wherein Rl is S(O)nCl-C4 alkyl or SO2di-Cl-C4 alkyl-amino; and R2 is H, halogen, CF3, NO2, Cl-C4 alkyl o Cl-C4 alkoxy.
This patent generically discloses, but does not claim, the compound of Formula I.
EP-A-101,670 published February 29, 1984, discloses a process for the preparation of herbicidal sulfonamides of the formula R j ~ O;! NHC NH ~( ~

wherein Rl is Q-Cl-C4 alkyl or SO2-di-Cl-C4 alkyl-amino; Q is S or S(O)n; and R2 is H, halogen, CF3, NO2, Cl-C4 alky Cl-C4 alkoxy.
This application generically discloses the compound of Formula I.
U.S. 4,521,597 discloses a process to prepare herbicidal sulfonamides of the formula R~ 8 2 NHC NH ~( ~E

wherein R3 is H, F, Cl, Br, NO2, OCH3 or CF3;
R5 is S()mCl~Cs alkyl or S02NR8Rg; and R6 is H, F, CH3 or OCH3.
This patent generically discloses, but does not claim, the compound of Formula I.
U.S. 4,744,814 discloses the following compound for selective weed control in tomatoes and turf.

~Oz NHgNH ~( ~

~ lo 1 336362 U.S. 4,778,512 discloses o-alkylcarbonyl-pyridinesulfonylureas.
EP-A-272,855 published June 29, 1988, discloses o-substituted-alkyl-pyridinesulfonylureas.
SUMMARY OF THE INVENTIQN
Despite the broad disclosures indicated above, a need still exists for selective herbicides, particularly for the control of undesired vegetation in a crop of potatoes or tomatoes. According to this invention such a selective herbicide has been discovered.
This invention comprises the novel use of the compound of Formula I as a preemergence and/or postemergence herbicide or plant growth regulant for selective control of undesired vegetation in a crop of potatoes or tomatoes.

S( ) 2CH2CH3 OCH3 O N~/
~0~5 ( ) 2 NHCNH ~O) N~

(N-[[4,6-dimethoxy-2-pyrimidinyl)amino]-carbonyl]-3-~ethylsulfonyl)-2-pyridine-sulfonamide, alternatively named N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide) and ~ 11 1 336362 the agriculturally suitable salts of the compound.
DETAILED ~ESCRIPTI~N OF THE INV~IO~
SYnthesis --The compound of Formula I can be prepared as described in Examples 1 to 6 as indicated in WO 88/04297.
Example 1 Prepara~ion of 3-ethyl~hio-2-fluoropyridine To a stirred solution of 236 ml (0.452 mol) of 1.9 molar lithium diisopropylamide (in hexanes) in 600 mls dry tetrahydrofuran cooled to -70 under nitrogen was added dropwise a solution of 40.0 g of 2-fluoropyridine (0.412 mol) in 100 mls dry tetrahydrofuran such that the temperature was maintained below -65. The solution was stirred at -70 for 4 hours and a solution 55.1 g of ethyl-disulfide (0.452 mol) in 150 mls dry tetrahydrofuran was added dropwise while maintaining the temperature below -65. After stirring another 2 hours at -70, the solution was poured into water and extracted with methylene chloride. The combined organic phases were washed with brine, dried over magnesium sulfate, and evaporated to afford crude product. This was purified by flash chromatography using 95:5 petroleum ether-ether as eluent to give 46.5 g (72%) of the title compound as an oil: NMR (CDC13, 200 MHz), 1.3 (3H, t, J = 7 Hz), 2.95 (2H, q, J ~ 7 Hz), 7.1 (lH, m), 7.7 (lH, m), 8.0 (lH, m); IR (neat) 1585, 1565, 1410, 1230 cm~l.

~ 12 1 336362 Example 2 Preparation of 3-ethylthio-2-(phenylmethylthio)-pyridinç = ~-To a stirred suspension of 8.6 g ~0.18 mol) of 50% sodium hydride (in mineral oil), which had been washed with hexanes, in 200 mls dry dimethylformamide cooled to -5 under nitrogen was added dropwise 22.7 g ~0.18 mol) benzyl mercaptan such that the temperature was maintained below 5. The suspension was stirred at room temperature for 1 hour, cooled to 0, and a solution of 25.0 g (0.160 mol) of the product from Example 1 was added dropwise while maintaining the temperature between 0 and 5. After warming to room temperature, the solution was poured into water and extracted with ether. The combined organic layers were washed with water and with brine, dried over magnesium sulfate, and evaporated to give 44.8 g (100%) of the title compound as a yellow liquid: NMR
(CDC13, 200 MHz), 1.28 (3H, t, J = 7 Hz), 2.9 (2H, q, J - 7 Hz), 4.4S (2H, s), 7.0-7.6 (7H, m), 8.35 (lH, m); IR (neat) 1610, 1405 cm~l.

Example 3 Preparation of N-(l,l-Dimethylethyl)-3-ethylsulfinyl-2-pyridinesulfonamide To a vigorously stirred mixture of 35.0 g (0.134 mol) of the product from Example 2 in 650 mls methylene chloride and 375 mls water cooled to 0 was added 0.63 mls (0.72 mol) concentrated hydrochloric acid followed by the dropwise addition of 650 mls (0.44 mol) of a 5% sodium hypochlorite solution such that the temperature was maintained between 0 and 5. After the mixture was stirred for an additional 30 minutes at 0 the reaction was poured into water and extracted with methylene chloride. The combined 13 ~ 336362 organic layers were washed with brine, dried over magnesium sulfate, and filtered. The filtrate was stirred and cooled to -70 under nitrogen and 49 g (0.67 ~ol) of t-butyl amine was added dropwise and the mixture was allowed to warm to room temperature. The reaction was poured into water and extracted with methylene chloride. The organic layers were combined and washed with brine, dried over magnesium sulfate, and evaporated which was washed with ether to leave 21.2 g (56%) of the title compound as a tan solid:
m.p. 129-131; NMR (CDC13, 200 MHz) 1.23 (9H, s), 1.28 (3H, t, J = 7 Hz), 2.9 (lH, m), 3.3 (lH, m), 5.2 (NH), 7.7 (lH, m), 8.55 (lH, m), 8.75 (lH, m); IR (nujol) 3100, 1320, 1155 cm~l.

Example 4 PreparatiQn of ~-(l,l-~imçthyle~hyl)-3-ethylsulfonyl-2-pyridinesulfonamide To a stirred solution of 9.0 g (0.033 mol) of the product from Example 3 in 400 mls methylene chloride cooled to -5, under nitrogen, was added 6.8 g (0.039 mol) of 3-chloroperbenzoic acid and stirred at room temperature for about 20 hours. The reaction mixture was poured into water and extracted with methylene chloride. The organic layers were combined and washed with saturated sodium bisulfite and brine, dried over magnesium sulfate, and evaporated to a solid mixture. This was slurried in l-chlorobutane, the solid discarded, and the filtrate evaporated. The residue was purified by flash chromatography using 2:1 then 1:1 petroleum ether-ethyl acetate as eluent to give 10.1 g (100%) of the title compound: m.p. 58-63; NMR (CDC13, 200 MHz) 1.2 ~ 14 1 336362 (3H, t, J = 7 Hz), 1.2 (9H, s), 3.7 (2H, q, J = 7 Hz), 6.1 (NH), 7.7 (lH, m), 8.55 (lH, m) 8.95 (lH, m); IR
(nujol) 3300, 1560, 1350, 1300, 1170, 1140 cm~l.

Example 5 P~eparation of 3-ethylsulfon~1-2-pyridinesulfonamide To a stirred solution of 9.0 g (0.029 mol) of the product from Example 4 was dissolved and stirred in 125 mls trifluoroacetic acid for about 72 hours.
The solution was evaporated and triturated with ether to afford 4.2 g (58%) of the title compound: m.p.
211-212.5; NMR (DMSO-d6, 200 MHz), 1.15 (3H, t, J ~ 7 Hz), 3.4 (NH2), 3.7 (2H, q, J = 7 Hz), 7.9 (lH, m), 8.5 (lH, m), 8.95 (lH, m); IR (nujol) 3370, 3190, 1350, 1310, 1180 cm~l.

Examplç 6 PreParation o (N-rr4,6-dimetho~y-~-pyrimidinyl)aminol-ca~bonyll-3-(ethylsulfDnyl)-~-pyridinesulfonamide To a stirred suspension of 0.60 g (0.0024 mol) o the product from Example 5 and 0.90 9 (0.0034 mol) of phenyl (4,6-dimethoxypyrimidin-2-yl)carbamate in 5 mls acetonitrile was added 0.52 g (0.0034 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene and stirred for 15 minutes. The solution was diluted with water and acidified with 1 normal hydrochloric acid. The resulting precipitate was collected and washed with water and ether to give 0.70 g (70%) of the title compound: m.p. 160-162; NMR (CDC13, 200 MHz) 1.35 (3H, t, J = 7 Hz), 3.7 (2H, q, J ~ 7 Hz), 3.97 (6H, s), 5.8 (lH, s), 7.3 (NH), 7.75 (lH, m), 8.6 (lH, m), 8.9 (lH, m), 12.95 (NH); IR (nujol) 3260, 1740, 1610, 1360, 1195, 1175 cm~l.
In the above Examples temperatures are reported in degrees Celsius; abbreviations for nuclear magnetic ~ 15 1 336362 resonance (NMR) are: s ~ singlet, d 3 doublet, t =
triplet, m . multiplet, and peak positions are reported as parts per million downfield from internal tetramethylsilane. Infrared (IR) peak positions are given in reciprocal centimeters (cm~l).
Agriculturally suitable salts of the compound of Formula I are also useful for the selective control of undesired vegetation in potato and tomato crops and can be prepared in a number of ways known to the art.
For example, metal salts can be made by contacting the compound of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydroxide). Quaternary amine salts can be made by similar techniques.
Salts of the compound of Formula I can also be prepared by exchange of one cation for another.
Cationic exchange can be effected by direct contact of an aqueous solution of a salt of the compound of Formula I (e.g., alkali or quaternary amine salt) with a solution containing the cation to be exchanged.
This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration.
Exchange may also be effected by passing an aqueous solution of a salt of the compound of Formula I (.e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble, e.g., a potassium, sodium or calcium salt.
Acid addition salts, useful in this invention, can be obtained by reacting the compound of Formula I

with a suitable acid, e.g., ~-toluene-sulfonic acid, trichloroacetic acid or the like.
Formulations Useful formulations of the compound of Formula I
can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly.
Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
Weight Perçent*
Active Inqredient ~iluent( 5 ) Surfactant(s) Wettable Powders20-90 0-74 1-10 Oil Suspensions, 3-50 40-95 0-15 Emulsions, Solutions, (including Emulsifiable Concentrates) Aqueous Suspension10-50 40-84 1-20 Dusts 1-25 70-99 0-5 Granules and Pellets 0.1-95 5-99.9 0-15 High Strength 90-99 0-10 0-2 Compositions * Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.
Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher - ~ 1 336362 ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.
Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide,"
2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates;
solution concentrates are preferably stable against phase separation at O~C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.
The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for e~ample, Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E.
~rowning, "Agglomeration", Chemical Enqineerinq, December 4, 1967, pp. 147ff. and ~'Perry's Chemical Engineer~s Handbook", 5th Ed., McGraw-Hill, New York, 1963, pp. 8-57ff.

18 1 33~3~

For further information regarding the art of formulation, see for e~ample:
H. M. Loux, U.S. Patent 3,235,361, February 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;
R. W. Luckenbaugh, U.S. Patent 3,309,192, March 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;
H. Gysin and E. Knusli, U.S. Patent 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;
G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., 81ackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.
~xample 7 - -Hiqh St~ength ~ncentrate N-[[4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide 99%
trimethylnonyl polyethylene glycol ether 1%
The surfactant is sprayed upon the active ingredient in a blender and the mixture sifted throuyh a U. S. S. No. 40 sieve (0.42 mm openings) prior to packaging. The concentrate may be formulated further for practical use.

..

~xampl e B
Wettable Powder ~-N-[[9,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide 65%
dodecylphenol polyethylene glycol ether 2%
sodium ligninsulfonate 4%
sodium silicoaluminate 6%
montmorillonite (calcined) 23%
The ingredients are thoroughly blended. The liquid surfactant is added by spraying upon the solid ingredients in the blender. After grinding in a hammer mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

Example 9 Aqueous Suspension N-[[4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide50.0%
polyacrylic acid thickener 0.3%
dodecylphenol polyethylene glycol ether0.5%
disodium phosphate 1%
monosodium phosphate 0.5%
polyvinyl alcohol 1.0%
water 56.7%
The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

Example 10 --Oil Su~pension N-[[4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl~-3-(ethylsulfonyl)-2-pyridinesulfonamide 35%

blend of polyalcohol carboxylic esters and oil soluble petroleum sulfonates 6%
xylene 59%
The ingredients are combined and ground together in a sand mill to produce particles essentially all below 3 microns. The product can be used directly, extended with oils, or emulsified in water.

Example 11 Oil Suspension --N-[[4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide25%
polyoxyethylene sorbitol hexaoleate 5%
highly aliphatic hydrocarbon oil 70%
The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

~ample 12 Aqueous Suspension N-[[4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide25%
hydrated attapulgite 3%
crude calcium ligninsulfonate 10%
sodium dihydrogen phosphate 0.5%
water 61.5%
The ingredients are ground together in a ball or roller mill until the solid particles have been reduced to diameters under 10 microns.

Example 13 Wettahle Pswder N-[t4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide40.0%

~ 21 1 336362 dioctyl sodium sulfosuccinate 1.5%
sodium ligninsulfonate 3%
low viscosity methyl cellulose 1.5%
attapulgite 54%
The ingredients are thoroughly blended, passed through an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.
All compounds of the invention may be formulated in the same manner.

Example 14 Granule wettable powder of Example 13 15%
gypsum 69%
potassium sulfate 16%
The ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 cm (U.S.S.#18 to 40 sieves), the granules are removed, dried, and screened. Oversized material is crushed to produce additional material in the desired range. These granules contain % active ingredient.

~xample 15 Wettabl~ Pow~er N-t[4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide 50%
sodium alkylnaphthalenesulfonate 2%
low viscosity methyl cellulose 2%
diatomaceous earth 46%
The ingredients are blended, coarsely hammer-milled and the air milled to produce particles of active essentially all below 10 microns in diameter.
The product is reblended before packaging.

1 336;36~

~xample 16 Extruded Pellet N-[[4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide 25%
anhydrous sodium sulfate 10%
crude calcium ligninsulfonate 5%
sodium alkylnaphthalenesulfonate 1%
calcium/magnesium bentonite 59%
The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

Exam~le 17 Wett a ble Pswd~r N-[[4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulonyl)-2-pyridinesulfonamide 80%
sodium alkylnaphthalenesulfonate 2%
sodium ligninsulfonate 2%
synthetic amorphous silica 3%
kaolinite 13%
The ingredients are blended and then ground in a hammermill to produce particles with an average particle size less than 25 microns in diameter. The material is reblended and sifted through a U.S.S. ~o.
50 sieve (0.3 mm opening) before being packaged.

-Example 1~
High S~rength ~oncent~ate - -N-[[4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyridinesul~onamide 98.5%
silica aerogel 0.5%
synthetic amorphous fine silica 1.0%
The ingredients are blended and ground in a hammer mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm openings). This material may then be formulated in a variety of ways.

Example 19 SolutiQn - - -N-[t4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide, sodium salt 5%
water 95%
The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

E~ample 20 Wettable PQW~er N-t[4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide 80%
sodium alkylnaphthalenesulfonate 2%
sodium ligninsulfonate 2%
synthetic amorphous silica 3%
kaolinite 13%
The ingredients are blended and then ground in a hammermill to produce particles with an average particle size less than 25 microns in diameter. The material is reblended and sifted through a U.S.S. No.
50 sieve (0.3 mm opening) before being packaged.

~ ~ 3363~2 ~ ample 21 Hiqh St~enqth Con~entra~e N-t[4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide 98.5%
silica aerogel 0.5%
synthetic amorphous fine silica 1.0%
The ingredients are blended and ground in a hammer mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm openings). This material may then be formulated in a variety of ways.
Utility Test results indicate that the compound of Formula I is a highly active preemergent and/or postemergent herbicide or plant growth regulant. The compound is particularly useful for broad-spectrum pre- and/or post-emergence grass and broadleaf weed control in potatoes (Solanum tuberosum) and tomatoes (Lycopersicon esculentum) . This compound suppresses or controls troublesome grass weeds such as barnyardgrass (Echinochloa crus-galli), blackgrass (Alopecurus myosuroides), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), foxtail (Setaria spp. ), johnsongrass (Sorghum halepense), and wild oat (Avena fatua); broadleaf weeds such as chickweed (SteZlaria spp.), cocklebur (Xanthium pensylvanicum ), j imsonweed (Datura stramollium), morningglory (Ipomoea hederacea), prickly sida (Sidaspinosa), sicklepod (Cassia tora), velvetleaf (Abutilon theophrast;), and wild buckwheat (Polygonumconvoluulus); and nutsedge (Cyperusrotultdus) with no significant crop injury to potatoes and tomatoes.
Test results also indicate that the compound of Formula I has utility for broad-spectrum pre- and/or 1 3~6362 postemergence weed control in other areas where control of vegetation is desired, such as around storage tanks, parking lots, drive-in theaters, billboards, highways, and railroad structures and in fallow areas of crop production such as in wheat, barley, and in plantation crops such as palm, banana, citrus, rubber, etc. Alternatively, this compound may be useful to modify plant growth or as a citrus abscission agent.
Rates of application for the compound of Formula I are determined by a number of factors. These factors include: formulation selected, method of application, amount of vegetation present, growing conditions, etc. In general terms, the subject compound should be applied at rates from 0.001 to 20 kg/ha with a preferred rate range of from 0.001 to 0.5 kg/ha. One skilled in the art can easily determine rates needed for the desired level of weed control.
The compound of Formula I may be used alone or in combination with other commercial herbicides, insecticides, or fungicides. The following list exemplifies some of the herbicides suitable for use in mixtures. A combination of the compound of Formula I
with one or more of the following herbicides may be particularly useful for weed control.

Comm~n Name Che~ical Name alachlor 2-chloro-2',6'-diethyl-N-(methoxymethyl)-acetanilide atrazine 2-chloro-4-(ethylamino)-6-(isopropyl-amino)-s-triazine butylate s-ethyl-diisobutylthiocarbamate Common NameChemical Name yanazine 2-t[4-chloro-6-(ethylamino)-s-triazin-2-yl]amino]-2-methylpropionitrile dicamba3,6-dichloro-o-anisic acid EPTC S-ethyl dipropylthiocarbamate linuron 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea etolachlor 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide etribuzin 4-amino-6-1~-butyl-3-(methylthio)-as-triazine-5(4H)-one tridiphane 2-(3,5-dichlorophenyl)-2-(2,2,2-tri-chloroethyl)oxirane 2,4-D (2,4-dichlorophenoxy)acetic acid bromoxynil 3,5-dibromo-4-hydroxyphenylcyanide paraquat l,l'-dimethyl-4,4-bipyridinium ion glyphosate N-(phosphonomethyl)glycine DPX M6316 3-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylic acid, methyl ester cinmethylin l-methyl-4-(1-methylethyl)-2-exo-[(2-methylphenyl)-methoxy]-7-oxabicyclo-[2.2.1]heptane DCPA dimethyl tetrachloroterephthalate dalapon 2,2-dichloropropionic acid dinoseb (2-(1-methylpropyl)-4,6-dinitrophenol) diphenamid N,N-dimethyl-2,2-diphenylacetamide pendimethalin N-(l-ethylpropyl)-3,4-dimethyl-2,6 dinitrobenamine oryzalin 3,5-dinitro-N,N-dipropylsulfanilamide -~ommon Name Chemical Name rifluralin a,a,a-trifluoro-2,6-dinitro-N-N-dipropyl-p-toluidine chloramben 3-amino-2,5-dichlorobenzoic acid napropamide 2-(a-naphthoxy)-N-,N-diethylpropionamide pebulate S-propyl butylethylthiocarbamate chlorpropham isopropyl m-chlorocarbanilate ensulide [S-(0,0-diisopropyl phosphorodithioate) ester of N-(2-mercaptoethyl)benzene-sulfonamide]
Test ~
Potatoes (Solanum tuberosum, cult. 'Green Mountain') were grown in Metro 350 medium in 20 cm plastic pots. Potatoes were 17 days old at time of spraying. Barnyardgrass (Echinochloa crus-galli), johnsongrass (Sorghum halepense), giant foxtail ~Setaria faberii), crabgrass (Digitaria sanguinalis), purple nutsedge (Cyperlcs rotundus), j imsonweed (Datura stramonium), velvetleaf (~butilon theophrasti), cocklebur (Xanthium pensy~vanicum), and morningglory (Ipomoea hederacea) were grown in sandy loam soil in plastic-lined 25 cm pots. These plants were 9 days old at the time of spraying.
The compound of Formula I was dissolved in a non-phytotoxic solvent and was sprayed at 62, 16, 4 and 1 g/ha. Each rate was sprayed on one pot containing potato plants and on one pot containing the remaining species. Plants were maintained in a greenhouse, and, after 11 days were evaluated for injury as compared to untreated control plants.
Injury was measured visually using a 0 to 100% scale where 0 = no effect and 100 = complete control. Test results are shown in Table A.

' 28 1 336362 TABLE A
HERBICIDAL INJURY AS PERCENT CONTROL
Rate (g/ha) SPECIES 62 1~ 4 Potato 0 0 0 0 Barnyardgrass 100 100 70 30 Johnsongrass 100 100 100 60 Giant foxtail 100 100 90 60 Crabgrass 90 85 60 50 Purple nutsedge 90 90 80 30 Jimsonweed 80 60 40 20 Velvetleaf 100 95 50 20 Cocklebur 90 50 30 0 Morningglory 90 70 40 20 Tes~ R ~ --Tomatoes (Lycopersico7~ esculentum cult. 'Rutgers') and peppers (Capsicum frutescens cult. 'Yolo') were grown in Metro 350 medium in 10 cm plastic pots. Tomatoes and peppers were 19 days old at time of spraying.
Purple nutsedge (Cyperus rotundus) crabgrass (Digitaria sanguinalis) sicklepod (Cassia tora) prickly sida (Sida spinosa) j imsonweed (Datura stramonium) velvetleaf (Abutilon theophrasti) lambsquarters (Chenopodium album) green foxtail (Setaria viridis ) cocklebur (Xanthium per~sylvanicum) morningglory (Ipomoea hederacea) johnsongrass (Sorghum halepense) barnyardgrass (Echinochloa crus-galli ) giant foxtail (Setarai faberii ) wild buckwheat (Polygonum co~lvolvulus) downy brome (Br om us fectorum ) wi ld oat (~vena fatu~ ) - ~ 1 336362 chickweed (Stellaria spp.), and blackgrass (Alopecurus myosuroides), were grown in a sandy loam soil in plastic-lined 25 cm pots. These plants were 7 to 11 days old at the time of spraying.
The compound of Formula I was dissolved in a non-phytotoxic solvent and was sprayed at 62, 16, 4, and 1 g/ha. Each rate was sprayed on one pot containing tomatoes, one pot containing peppers, and on three pots containing the remaining species.
Plants were maintained in a greenhouse and, after 16 days, were evaluated for injury as compared to untreated control plants. Injury was measured visually using a O to 100~ scale where O = no effect and 100 5 complete control. Test results are shown in Table B.

3 ~ 3 3 6 3 6 2 A~

TABLE B
HERBICIDAL INJURY AS PERCENT CONTROL
Rate (g/ha) Tomatoes 10 0 0 0 Peppers 80 70 50 30 Nutsedge 100 100 30 0 Crabgrass 90 80 50 30 Sicklepod 100 100 90 40 Prickly sida 100 100 50 20 Jimsonweed 100 50 10 0 Velvetleaf 100 100 70 50 Lambsquarters 60 50 40 0 Green foxtail 100 100 100 50 Cocklebur 100 80 50 20 Morningglory 90 85 50 20 Johnsongrass 100 100 100 50 Barnyardgrass 100 100 100 40 Giant foxtail 100 100 90 40 Wild buckwheat 100 90 90 40 Downy brome 100 100 80 20 Wild oat 100 70 30 20 Chickweed 100 100 90 90 Blackgrass 100 100 100 70

Claims

1. A method for selective control of undesired vegetation in a crop of potatoes or tomatoes which comprises applying to the locus to be protected an effective amount of I

or the agriculturally suitable salts thereof.