A pyridine sulfonylurea herbicide, composition thereof and a method for its use that results in the control of blackgrass in cereal crops and general control of all plant growth.

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 desired 
product of Formula I can be conveniently isolated by acidifying the 
reaction solution with aqueous hydrochloric acid. Alternatively, the 
aqueous layer can be extracted with a solvent such as methylene chloride 
or ethyl acetate. Drying and evaporation of the solvent affords the 
desired product. The phenyl carbamate can be synthesized by treatment of 
the corresponding heterocyclic amine of Formula A--NH.sub.2 with diphenyl 
carbonate or phenyl chloroformate in the presence of a base such as sodium 
hydride, pyridine, or potassium carbonate with a catalytic amount of a 
catalyst, such as, 4-dimethylaminopyridine. The mixture is stirred at 
temperatures between 25.degree. C. and 65.degree. C. in a suitable solvent 
such as tetrahydrofuran for 12-36 hours. 
The compound of Formula I can also be synthesized by the reaction of the 
appropriate arylsulfonylcarbamates of Formula IIIc with the heterocyclic 
amine IIId as shown in Equation 1b. This reaction can be carried out in 
the presence of various bases as described in Equation 1a, or by simply 
refluxing in an appropriately high boiling solvent such as dioxane. The 
arylsulfonylcarbamates can be synthesized by the reaction of sulfonamide 
II with phenyl or alkyl carbonates IIIb (or the corresponding 
chloroformates) in the presence of a variety of bases. 
##STR8## 
wherein 
R.sub.2 is phenyl or C.sub.1 -C.sub.4 alkyl; and 
J and A are as previously defined. 
The required sulfonamide of Formula II can be synthesized by either one of 
the methods shown below in Equations 2 and 3. 
Equation 2 depicts the reaction of the sulfonyl chloride of Formula IV with 
ammonia to give sulfonamide of Formula II. 
##STR9## 
wherein 
J is as previously defined. 
The amination of Equation 2 is conveniently effected by adding at least two 
molar equivalents of either anhydrous ammonia or concentrated ammonium 
hydroxide to a solution of the sulfonyl chloride IV in a suitable solvent 
such as diethyl ether, tetrahydrofuran or methylene chloride at 
temperatures between -30.degree. C. and 25.degree. C. The desired 
sulfonamide of Formula II is isolated either by filtration, in which case 
the by-product ammonium chloride is removed by washing with water, or 
extraction into a suitable organic solvent such as methylene chloride or 
ethyl acetate. Drying and evaporation of the solvent then affords the 
product II which is usually sufficiently pure to be carried directly on to 
the next step. 
The sulfonamide of Formula II can also be prepared as shown in Equation 3 
by treatment of the corresponding N-t-butylsulfonamide VI with an excess 
of an acid such as trifluoroacetic (TFA), polyphosphoric (PPA), or 
p-toluenesulfonic acid (p-TSA). 
##STR10## 
wherein 
J is as previously defined. 
The reaction of Equation 3 is conveniently carried out by stirring a 
solution of the compound of Formula VI in excess trifluoroacetic acid 
(approximately 0.3M) at about 25.degree. C. for 1-72 hours. The desired 
sulfonamide of Formula II is then isolated by removal of the volatiles in 
vacuo and crystallization from a suitable solvent such as diethyl ether, 
1-chlorobutane, or ethyl acetate. Alternatively, the N-t-butylsulfonamide 
of Formula VI can be treated with a catalytic amount of p-toluenesulfonic 
acid monohydrate in a solvent such as toluene or xylenes at reflux 
temperature for 1-6 hours. The desired product is then isolated in a 
manner analogous to the one described above. For use of polyphosphoric 
acid in the deprotection of N-t-butylsulfonamides, see J. G. Lombardino, 
J. Org. Chem., 1971, 36, 1843-1845; for use of trifluoroacetic acid, see 
J. D. Catt and W. L. Matier, J. Org. Chem., 1974, 39, 566-568. 
The sulfonamide of Formula VI can be prepared by the reaction of the 
sulfonyl chloride of Formula IV with excess t-butyl amine as shown in 
Equation 4. 
##STR11## 
wherein 
J is as previously defined. 
The sulfonyl chloride of Formula IV can be prepared according to the 
procedures described in U.S. Pat. No. 4,456,469. Alternatively, the 
procedures of U.S. Pat. No. 4,741,764 may be utilized which described the 
conversion of mercapto or arylmethylthio compounds to sulfonyl chlorides 
via treatment with hypochlorite solution. 
The sulfides of Formula V can be prepared by the reaction of a halo 
pyridine compound of Formula VII with an appropriate mercaptan in the 
presence of a base as described in U.S. Pat. No. 4,456,469 and shown in 
Equation 5. 
##STR12## 
wherein 
X' is F, Cl, or Br; and 
R' is C.sub.1 -C.sub.4 alkyl or benzyl. 
A method to prepare the sulfonamide of Formula VIIIe is shown in Equation 
6. The trifluoromethyl ketone intermediate VIIIa is prepared according to 
the procedures of Lang et al., Helv. Chim. Acta. 1988, 71, 596-601. In a 
modification of this procedure, VIIIa is then treated with ethyl malonate 
monoamide (or ethyl carbamoylacetate) in the presence of sodium methoxide 
to afford the trifluoromethyl pyridinone methyl ester VIIIb. Heating VIIIb 
with phosphorous oxybromide or oxalyl bromide/dimethylformamide (DMF) in 
methylene chloride results in the bromopyridine VIIIc. Conversion to the 
benzyl sulfide VIIId and the sulfonamide VIIIe is carried out as 
previously described. 
##STR13## 
Agriculturally suitable salts of the compound of Formula I are also useful 
herbicides 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. For example, cationic exchange can be effected by 
direct contact of a solution of a salt of a 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 the solution and can be 
separated by filtration. 
Exchange may also be effected by passing an aqueous solution of a salt of a 
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 watersoluble, e.g., a potassium, sodium or calcium salt. 
Acid addition salts, useful in this invention, can be obtained by reacting 
a compound of Formula I with a suitable acid, e.g., p-toluenesulfonic 
acid, trichloroacetic acid or the like. 
The preparation of the compounds of this invention is further illustrated 
by the following specific examples. Temperatures are reported in degrees 
Celsius; abbreviations for nuclear magnetic resonance (NMR) are: 
S=singlet, d=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.sup.-1). 
EXAMPLE 1 
Preparation of methyl 
1,2-dihydro-2-oxo-6-(trifluoromethyl)-3-pyridinecarboxylate (VIIIb) 
To a stirred solution of 2.0 g (0.0102 mol) of 
4-butoxy-1,1,1-trifluoro-3-buten-2-one (VIIIa) and 1.3 g (0.0102 mol) of 
ethyl malonate monoamide in 10 mL methyl alcohol was added 2.2 mL (0.0102 
mol) of a 25% solution of sodium methoxide in methanol. The solution 
turned into a thick yellow suspension which was refluxed overnight. The 
suspension was cooled to room temperature, poured into water, acidified 
with one normal hydrochloric acid and extracted with methylene chloride. 
The combined organic layers were washed with brine, dried over magnesium 
sulfate and evaporated to afford 1.7 g (74%) of a yellow solid. m.p. 
63.degree.-64.degree. C.; .sup.1 H NMR (CDCl.sub.3) .delta.4.0 (3H, s), 
7.33 (1H, d, J=8 Hz), 8.4 (1H, d, J=8 Hz); IR (mineral oil) 3080, 1675 
(br), 1605, 1450, 1375 cm.sup.-1. 
EXAMPLE 2a 
Preparation of methyl 2-bromo-6-(trifluoromethyl)-3-pyridinecarboxylate 
(VIIIc) 
A suspension of 22.0 g (0.100 mol) of the product from Example 1 and 28.7 g 
(0.100 mol) of phosphorous oxybromide was heated at 75.degree.-120.degree. 
C. over 45 minutes utilizing an oil bath as the heat source. The reaction 
was also connected to a water scrubber to trap the gas by-products. The 
mixture was then cooled to room temperature, diluted with water and 
extracted with methylene chloride. The combined organic layers were washed 
with saturated sodium bicarbonate solution, washed with brine, dried over 
magnesium sulfate and evaporated to an oil which was purified by flesh 
chromatography utilizing 20% ethyl acetate/petroleum ether as the eluent 
to afford 3.8 g (13.3%) of an oil. .sup.1 H NMR (CDCl.sub.3) .delta.4.0 
(3H, s), 7.72 (1H, d, J=8 Hz), 8.2 (1H, d, J=8 Hz); IR (neat) 1740, 1590, 
1455, 1335, 1275, 1140, 1100, 1050 cm.sup.-1. 
EXAMPLE 2b 
Preparation of methyl 2-bromo-6-(trifluoromethyl)-3-pyridinecarboxylate 
(VIIIc) 
To a stirred solution of 2.0 g (0.0091 mol) of the product from Example 1 
in 25 mL methylene chloride under nitrogen was added 0.92 mL (0.0118 mol) 
of dimethylformamide followed by 1.57 mL (0.011 mol) of oxyalyl bromide 
which resulted in an exotherm to 35.degree. C. and gas evolution before 
all the oxalyl bromide was added. The reaction was cooled to room 
temperature and the remaining oxalyl bromide was added. The solution was 
stirred for 1 h at room temperature during which time an orange-yellow 
suspension appeared. The reaction was refluxed 3 h, cooled to room 
temperature and stirred overnight. Another 0.79 mL (0.0055 mol) of oxalyl 
bromide and 0.46 mL (0.006 mol) of dimethylformamide were added and 
refluxed 6 h and then refluxed overnight. Another 0.79 mL (0.0055 mol) of 
oxalyl bromide was added and refluxed 5 h. The reaction was poured into 
approximately 50 mL water and to this was added about 150 mL ether. The 
organic layer was separated, washed with brine, dried over magnesium 
sulfate and evaporated to an oil which was purified by flash 
chromatography using 20% ethyl acetate/hexanes as the eluent which 
afforded 1.53 g (.about.55%) of an oil whose NMR was similar to Example 
2a, with the exception of approximately 10% contamination of 
dimethyloxalate. 
EXAMPLE 3a 
Preparation of methyl 
2-[(phenylmethyl)thio]-6-(trifluoromethyl)-3-pyridinecarboxylate (VIIId) 
To a stirred suspension of 0.28 g (0.008 mol) of 60% sodium hydride (in 
mineral oil, then washed with hexanes) in 7 mL dry dimethylformamide under 
nitrogen at 0.degree. C. was added 0.8 mL (0.0067 mol) of benzyl mercaptan 
while maintaining the temperature below 10.degree. C. The suspension was 
warmed to room temperature and stirred another 45 minutes before cooling 
back to 0.degree. C. A solution of 2.0 g (0.0067 mol) of the product from 
Example 2a or 2b in 5 mL dry dimethylformamide was added dropwise and 
stirred 30 minutes at 0.degree. C. The reaction was poured into ice water 
and extracted with ether. The combined organic layers were washed with 
brine, dried over magnesium sulfate and evaporated to afford 2.3 g (100%). 
.sup.1 H NMR (CDCl.sub.3) .delta., 3.94 (3H, s), 4.43 (2H, s), 7.2-7.6 
(6H, m), 8.38 (1H, d, J=8Hz). 
EXAMPLE 3b 
Preparation of methyl 
2-[(phenylmethyl)thio]-6-(trifluoromethyl)-3-pyridinecarboxylate (VIIId) 
To a stirred suspension of 6.55 g (0.0584 mol) of potassium-t-butoxide in 
60 mL dry dimethylformamide under nitrogen at 0.degree. C. was added 6.84 
mL (0.0584 mol) of benzyl mercaptan in 20 mL dimethylformamide while 
maintaining the temperature below 15.degree. C. A solution of 15.83 g 
(0.053 mol) of the product from Example 2a or 2b in 20 mL dry 
dimethylformamide was added dropwise maintaining the temperature at 
0.degree. C. and then stirred another 30 minutes at 0.degree. C. The 
reaction was poured into ice water and extracted with ether. The combined 
organic layers were washed with water, brine, dried over magnesium sulfate 
and evaporated to afford 17.84 g (100%). .sup.1 H NMR is similar to 
Example 3. IR (neat) 1725, 1675, 1575, 1135, 850 cm.sup.-1. 
EXAMPLE 4 
Preparation of methyl 
2-[[(1,1-dimethylethyl)amino]-sulfonyl]-6-(trifluoromethyl)-3-pyridinecarb 
oxylate (VIIIe) 
To a stirred mixture of 2.3 g (0.007 mol) of the product from Example 3a or 
3b in 75 mL methylene chloride and 35 mL water cooled to 0.degree. C. was 
added 2.1 mL (0.025 mol) concentrated hydrochloric acid followed by the 
dropwise addition of 36 mL (0.0245 mol) of a 5% sodium hypochlorite 
solution such that the temperature was maintained below 10.degree. C. 
After the mixture was stirred another 15 minutes at 0.degree. C., the 
reaction was poured into water and extracted with methylene chloride. The 
combined organic layers were washed with brine, dried over magnesium 
sulfate and filtered. The filtrate was stirred and cooled to -70.degree. 
C. under nitrogen, and 2.6 g (0.035 mol) of t-butyl amine was added 
dropwise. The mixture was warmed to -30.degree. C., poured into water and 
extracted with methylene chloride. The combined organic layers were washed 
with brine, dried over magnesium sulfate and evaporated. Purification by 
flash chromatography using 20% ethyl acetate/petroleum ether as the eluent 
afforded 1.07 g (45%) of a solid. m.p. 76.degree.-83.degree. C.; .sup.1 H 
NMR (CDCl.sub.3) .delta.1.25 (9H, s), 4.0 (3H, s), 5.35 (NH), 7.9 (1H, m), 
8.2 (1H, m); IR (mineral oil) 3320, 1745, 1335, 1140 cm.sup.-1. 
EXAMPLE 5 
Preparation of methyl 
2-(aminosulfonyl)-6-(trifluoromethyl)-3-pyridinecarboxylate (II) 
A solution of 0.95 g (2.79 mmol) of the product from Example 4 was stirred 
in 40 mL trifluoroacetic acid at room temperature overnight. The solution 
was evaporated to an oil which was triturated with ether to afford 0.46 g 
(58%) of a solid. m.p. 187.degree.-188.degree. C. .sup.1 H NMR 
(CDCl.sub.3) .delta.4.05 (3H, s), 5.5 (NH.sub.2), 7.95 (1H, d, J=8 Hz), 
8.35 (1H, d, J=8 Hz); IR (mineral oil) 3390, 3280, 1725, 1340, 1140 
cm.sup.-1. 
EXAMPLE 6 
Preparation of methyl 
2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-6-(trifl 
uoromethyl)-3-pyridinecarboxylate (I) 
To a stirred solution of 0.05 g (0.176 mmol) of the product from Example 5 
and 0.06 g (0.211 mmol) of phenyl (4,6-dimethoxypyrimidin-2-yl) carbamate 
in 0.5 mL acetonitrile was added dropwise 0.028 g (0.185 mmol) of 
1,8-diazabicyclo[5.4.0]undec-7-ene and was stirred 15 minutes. The 
solution was diluted with water, acidified with 1 normal hydrochloric acid 
and extracted with methylene chloride. The combined organic layers were 
washed with brine, dried over magnesium sulfate and evaporated to an oil 
which was triturated with ether to afford 0.03 g (54%) of a solid. m.p. 
130.degree.-137.degree. C. .sup.1 H NMR (CDCl.sub.3) .delta.3.96 (6H, s), 
4.05 (3H, s), 5.82 (1H, s), 7.3 (NH), 7.93 (1H, d, J=approximately 8 Hz), 
8.4 (1H, d, J=approximately 8 Hz), 13.1 (NH); IR (mineral oil) 3180, 1745, 
1715, 1370, 1140 cm.sup.-1. 
EXAMPLE 7 
Preparation of the sodium salt of methyl 
2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-6-(trifl 
uoromethyl)-3-pyridinecarboxylate (I) 
To a stirred solution of 50.0 g (0.176 mol) methyl 
2-(aminosulfonyl)-6-(trifluoromethyl)-3-pyridine-carboxylate and 55.0 g 
(0.200 mol) phenyl 4,6-dimethoxypyrimidine-2-yl carbamic acid ester in 75 
mL dimethylformamide was added 30 mL triethylamine at room temperature. 
After dissolution of the solids, the amber solution was diluted with 150 
mL methanol. To this solution 40 g (0.185 mol) of 25% sodium methoxide 
solution was slowly added at room temperature. After 10 g of the 25% 
sodium methoxide solution was added, the solution was seeded with 1.0 g of 
previously prepared title compound. The resulting precipitate was cooled 
to 10.degree. C. and stirred for 30 minutes. The solid precipitate was 
filtered and washed with cold methanol (2.times.50 mL) to afford 75.7 g of 
a solid, m.p. 176.degree.-177.degree. C. dec. The solid contained 3.0% 
water by Karl Fisher titration and 89.2% of the title compound which was 
assayed by HPLC. The yield corrected for methyl 
2-(aminosulfonyl)-6-(trifluoro-methyl)-3-pyridinecarboxylate and the added 
seed was 81.4%. 
EXAMPLE 8 
Preparation of the sodium salt of methyl 
2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-6-(trifl 
uoromethyl)-3-pyridinecarboxylate (I) 
To a solution of 9.5 g (0.021 mol) methyl 
2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-6-(trifl 
uoromethyl)-3-pyridinecarboxylate dissolved in 40 mL methanol was added 5.0 
mL (0.023 mol) of 25% sodium methoxide in methanol. The resulting slurry 
was stirred at room temperature for 40 min. and then filtered to afford 
8.3 g of the sodium salt, m.p. 172.degree.-173.degree. C. dec. The water 
content was 5.9% by Karl Fisher titration. 
By applying the procedures of U.S. Pat. No. 4,774,337 or Examples 1 through 
8 and Equations 1 through 6, the compound of Formula I (Compound 1) can be 
prepared by one skilled in the art. 
COMPOUND TABLE 
______________________________________ 
##STR14## Compound 1 
______________________________________ 
Formulations 
Useful formulations of the compounds 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 0% to 99.9% solid or liquid inert diluent(s). More specifically, 
they will contain these ingredients in the following approximate 
proportions: 
______________________________________ 
Weight Percent* 
Active 
Ingredient 
Diluent(s) 
Surfactant(s) 
______________________________________ 
Wettable Powders 
20-90 0-74 1-10 
Oil Suspension, 
3-50 40-95 0-15 
Emulsions, Solutions, 
(including Emulsifiable 
Concentrates) 
Aqueous Suspension 
10-50 40-84 1-20 
Dusts 1-25 70-99 0-5 
Granules and Pellets 
0.1-95 5-99.9 1-15 
High Strength 90-99 0-10 0-2 
Compositions 
Filled Film 0.1-90 10-90 0-10 
______________________________________ 
*Active ingredient plus at least one of a Surfactant or a Diluent equal 
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 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, 
N.J., 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 0.degree. 
C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., 
Ridgewood, N.J., 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 example, Littler, 
U.S. Pat. No. 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. Browning, "Agglomeration", Chemical Engineering, 
Dec. 4, 1967, pp. 147ff and "Perry's Chemical Engineer's Handbook", 5th 
Ed., McGraw-Hill, New York, 1963, pp. 8-57ff. 
For further information regarding the art of formulation, see for example: 
H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through 
Col. 7, line 19 and Examples 10 through 41; 
R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 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. Pat. No. 2,891,855, Jun. 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., Blackwell 
Scientific Publications, Oxford, 1968, pp. 101-103. 
In the following examples, all parts are by weight unless otherwise 
indicated. 
EXAMPLE A 
High Strength Concentrate 
______________________________________ 
Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
99% 
amino]carbonyl]amino]sulfonyl]-6-(trifluoro- 
methyl)-3-pyridinecarboxylate 
trimethylnonyl polyethylene 
1% 
glycol ether 
______________________________________ 
The surfactant is sprayed upon the active ingredient in a blender and the 
mixture sifted through a U.S.S. No. 40 sieve (0.42 mm openings) prior to 
packaging. The concentrate may be formulated further for practical use. 
EXAMPLE B 
Wettable Powder 
______________________________________ 
Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
65% 
amino]carbonyl]amino]sulfonyl]-6-(trifluoro- 
methyl)-3-pyridinecarboxylate 
dodecylphenol polyethylene 
2% 
glycol ether 
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 C 
Aqueous Suspension 
______________________________________ 
Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
50.0% 
amino]carbonyl]amino]sulfonyl]-6-(trifluoro- 
methyl)-3-pyridinecarboxylate 
polyacrylic acid thickener 0.3% 
dodecylphenol polyethylene 0.5% 
glycol ether 
disodium phosphate 1% 
monosodium phosphate 0.5% 
polyvinyl alcohol 1.0% 
water 46.7% 
______________________________________ 
The ingredients are blended and ground together in a sand mill to produce 
particles essentially all under 5 microns in size. 
EXAMPLE D 
Oil Suspension 
______________________________________ 
Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
35% 
amino]carbonyl]amino]sulfonyl]-6-(trifluoro- 
methyl)-3-pyridinecarboxylate 
blend of polyalcohol carboxylic esters 
6% 
and oil soluble petroleum sulfonates 
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 E 
Oil Suspension 
______________________________________ 
Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
25% 
amino]carbonyl]amino]sulfonyl]-6-(trifluoro- 
methyl)-3-pyridinecarboxylate 
polyoxyethylene sorbitol 5% 
hexaoleate 
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. 
EXAMPLE F 
Aqueous Suspension 
______________________________________ 
Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
25% 
amino]carbonyl]amino]sulfonyl]-6-(trifluoro- 
methyl)-3-pyridinecarboxylate 
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 G 
Wettable Powder 
______________________________________ 
Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
40.0% 
amino]carbonyl]amino]sulfonyl]-6-(trifluoro- 
methyl)-3-pyridinecarboxylate 
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 H 
Granule 
______________________________________ 
wettable powder 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 mm (U.S.S. No. 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. 
EXAMPLE I 
Wettable Powder 
______________________________________ 
Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
50% 
amino]carbonyl]amino]sulfonyl]-6-(trifluoro- 
methyl)-3-pyridinecarboxylate 
sodium alkylnaphthalenesulfonate 
2% 
low viscosity methyl cellulose 
2% 
diatomaceous earth 46% 
______________________________________ 
The ingredients are blended, coarsely hammer-milled and then air milled to 
produce particles or active ingredient essentially all below 10 microns in 
diameter. The product is reblended before packaging. 
EXAMPLE J 
Extrude Pellet 
______________________________________ 
Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
25% 
amino]carbonyl]amino]sulfonyl]-6-(trifluoro- 
methyl)-3-pyridinecarboxylate 
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 cylinder 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. 
EXAMPLE K 
Wettable Powder 
______________________________________ 
Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
80% 
amino]carbonyl]amino]sulfonyl]-6-(trifluoro- 
methyl)-3-pyridinecarboxylate 
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. 
EXAMPLE L 
High Strength Concentrate 
______________________________________ 
Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
98.5% 
amino]carbonyl]amino]sulfonyl]-6-(trifluoro- 
methyl)-3-pyridinecarboxylate 
silica aerogel 0.5% 
synthetic amorphous fine silica 
1.0% 
______________________________________ 
The ingredients are blended and ground in a hammermill 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 M 
Solution 
______________________________________ 
Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
amino]carbonyl]amino]sulfonyl]-6-(trifluoro- 
methyl)-3-pyridinecarboxylate 
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. 
EXAMPLE N 
Solution 
______________________________________ 
Methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
amino]carbonyl]amino]sulfonyl]-6-(trifluoro- 
methyl)-3-pyridinecarboxylate 
sodium salt 50% 
aqueous polyvinyl alcohol solution 
49% 
sodium dodecylbenzene sulfonate 
1% 
______________________________________ 
The dry ingredients are ground together and then mixed into the polyvinyl 
alcohol solution. The blend is cast as a film of 10-40 mL on a flat 
surface and then dried to remove the excess water. 
UTILITY 
Test results indicate that the compound of the present invention is a 
highly active preemergent and/or postemergent herbicide or plant growth 
regulant. The compound has utility for pre- and/or postemergence 
broadspectrum grass and broadleaf control in cereal crops. The compound is 
particularly useful for the control of blackgrass (Alopecurus myosuroides) 
in cereal crops such as wheat (Triticum aestivum), barley (Hordeum 
vulgare), cats (Avena sativa), rye (Secale cereale) and triticale 
(Triticum.times.Secale). 
An effective amount of the compound of this invention is determined by a 
number of factors. These factors include: formulation selected, method of 
application, amount of vegetation present, growing conditions, etc. In 
general terms, an effective amount of the compound of the invention is 
applied at rates of from 0.001 to 20 kg/ha, with a preferred range of from 
0.002 to 0.25 kg/ha. The compound of this invention 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 this invention with 
one or more of the following herbicides may be particularly useful for 
weed control in cereal crops. 
______________________________________ 
Common Name Chemical Name 
______________________________________ 
amidosulfuron N-[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
amino]carbonyl]amino]sulfonyl]-N- 
methylmethanesulfonamide 
barban 4-chloro-2-butynyl 3-chlorocarbamate 
bensulfuron 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)- 
methyl amino]carbonyl]amino]sulfonyl]- 
methyl]benzoic acid, methyl ester 
bentazon 3-(1-methylethyl)-(1H)-2,1,3-benzo- 
thiadiazin-4(3H)-one, 2,2-dioxide 
benzoylprop N-benzoyl-N-(3,4-dichlorophenyl)-DL- 
alanine 
bifenox methyl 5-(2,4-dichlorophenoxy)-2- 
nitrobenzoate 
bromoxynil 3,5-dibromo-4-hydroxybenzonitrile 
butachlor N-(butoxymethyl)-2-chloro-N-(2,6- 
diethylphenyl)acetamide 
chlorpropham 1-methylethyl 3-chlorophenylcarbamate 
chlorsulfuron 2-chloro-N-[[(4-methoxy-6-methyl- 
1,3,5-triazin-2-yl)amino]- 
carbonyl]benzenesulfonamide 
chlortoluron N'-(3-chloro-4-methylphenyl)-N,N- 
dimethylurea 
cinmethylin exo-1-methyl-4-(1-methylethyl)-2-[(2- 
methylphenyl)methoxy]-7-oxabicyclo- 
[2.2.1]heptane 
DCPA dimethyl 2,3,5,6-tetrachloro-1,4- 
benzenedicarboxylate 
diallate S-(2,3-dichloro-2-propenyl)bis(1- 
methylethyl)carbamothioate 
dicamba 3,6-dichloro-2-methoxybenzoic acid 
dichlobenil 2,6-dichlorobenzonitrile 
dichlorprop (.+-.)-2-(2,4-dichlorophenoxy)propanoic 
acid 
dichlofop (.+-.)-2-[4-(2,4-dichlorophenoxy)- 
phenoxy]propanoic acid 
difenzoquat 1,2-dimethyl-3,5-diphenyl-1H- 
pyrazolium 
diflufenican 2',4'-difluoro-2-(.alpha.,.alpha.,.alpha.-trifluoro-m- 
tolyloxy)nicotinanilide 
DNOC 2-methyl-4,6-dinitrophenol 
fenoxaprop-ethyl 
ethyl (.+-.)-2-[4-[(6-(chloro-2-benz- 
oxazolyl)oxy]phenoxy]propanoate 
fenoxaprop-ethyl 
with crop safener 
flamprop N-benzoyl-N-(3-chloro-4-fluoro- 
phenyl)-DL-alanine 
fluazifop (.+-.)-2-[4-[[5-(trifluoromethyl)-2- 
pyridinyl]oxy]phenoxy]propanoic 
acid 
fluazifop-P (R)-2-[4-[[5-(trifluoromethyl)-2- 
pyridinyl]oxy]phenoxy]propanoic 
acid 
fluchloralin N-(2-chloroethyl)-2,6-dinitro-N- 
propyl-4-(trifluoromethyl)- 
benzenamine 
fluorochloridine 
3-chloro-4-(chloromethyl)-1-[3-(tri- 
fluoromethyl)phenyl]-2- 
pyrrolidinone 
fluroxypyr 4-amino-3,5-dichloro-6-fluoro-2- 
pyridyloxyacetic acid 
imazamethabenz 
6-(4-isopropyl-4-methyl-5-oxo-2- 
imidazolin-2-yl)- .sub.-- m-toluic acid, 
methyl ester and 6-(4-isopropyl-4- 
methyl-5-oxo-2-imidazolin-2-yl)- -p- 
toluic acid, methyl ester 
ioxynil 4-hydroxy-3,5-diiodobenzonitrile 
isoproturon N-(4-isopropylphenyl)-N',N'- 
dimethylurea 
linuron N'-(3,4-dichlorophenyl)-N-methoxy-N- 
methylurea 
MCPA (4-chloro-2-methylphenoxy)acetic acid 
MCPB 4-(4-chloro-2-methylphenoxy)butanoic 
acid 
mecoprop (.+-.)-2-(4-chloro-2-methylphenoxy)- 
propanoic acid 
mefluidide N-[2,4-dimethyl-5-[[(trifluoro- 
methyl)sulfonyl]amino]phenyl]- 
acetamide 
methabenz- 1,3-dimethyl-3-(2-benzothiazolyl)- 
thiazuron urea 
methoxuron N'-(3-chloro-4-methoxyphenyl)-N,N- 
dimethylurea 
metribuzin 4-amino-6-(1,1-dimethylethyl)-3- 
(methylthio)-1,2,4-triazin-5(4H)- 
one 
metsulfuron 2-[[[[(4-methoxy-6-methyl-1,3,5- 
methyl triazin-2-yl)amino]carbonyl]amino]- 
sulfonyl]benzoic acid, methyl ester 
monuron N'(4-chlorophonyl)-N,N-dimethylurea 
neburon 1-butyl-3-(3,4-dichlorophenyl)-1- 
methyl urea 
picloram 4-amino-3,5,6-trichloro-2-pyridine- 
carboxylic acid 
PPG-1013 5-[2-chloro-4-(trifluoromethyl)- 
phenoxy]-2-nitroacetophenone oxime- 
O-acetic acid, methyl ester 
propanil N-(3,4-dichlorophenyl)propanamide 
sulfometuron 2-[[[[(4,6-dimethyl-2-pyrimidinyl)- 
methyl amino]carbonyl]amino]sulfonyl]- 
benzoic acid, methyl ester 
terbuthylazine 
2-(tert-butylamino)-4-chloro-6- 
(ethylamino)- .sub.- s-triazine 
terbutryn N-(1,1-dimethylethyl)-N'-ethyl-6- 
(methylthio)-1,3,5-triazine-2,4- 
dismine 
thifensulfuron 
[[[[(4-methoxy-6-methyl-1,3,5- 
methyl triazin-2-yl)amino]carbonyl]amino]- 
sulfonyl]-2-thiophenecarboxylic 
acid, methyl ester 
triallate S-(2,3,3-trichloro-2-propenyl) 3- 
bis(1-methylethyl)carbamothioate 
tribenuron methyl 
2-[[[[N-(4-methoxy-6-methyl-1,3,5- 
triazine-2-yl)-N-methylamino]- 
carbonyl]amino]sulfonyl]benzoic 
acid, methyl ester 
trifluralin 2,6-dinitro-N,N-dipropyl-4-(tri- 
fluoromethyl)benzenamine 
2,4-D (2,4-dichlorophenoxy)acetic acid 
2,4-DB 4-(2,4-dichlorophenoxy)butanoic acid 
______________________________________ 
The selective herbicidal properties of the subject compound that make it 
useful as a cereal herbicide was discovered in a number of greenhouse and 
field tests. The outstanding control of blackgrass (Alopecurus 
myosuroides) by the invention compound is particularly demonstrated in 
results of three field tests represented by Tables D, E and F. Test 
descriptions and results follow. 
TEST A 
Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), 
cheatgrass (Bromus secalinus), cocklebur (Xanthium pensylvanicum), corn 
(Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), giant 
foxtail (Setaria faberi), morningglory (Ipomoea spp.), rice (Oryza 
sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet 
(Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum 
aestivum), wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) 
tubers were planted and treated preemergence with test chemicals dissolved 
in a non-phytotoxic solvent. At the same time, these crop and weed species 
were also treated with postemergence applications of test chemicals. 
Plants ranged in height from two to eighteen cm (two to three leaf stage) 
for postemergence treatments. Treated plants and controls were maintained 
in a greenhouse for approximately sixteen days, after which all species 
were compared to controls and visually evaluated. Plant response ratings, 
summarized in Table A, are based on a scale of 0 to 10 where 0 is no 
effect and 10 is complete control. A dash (-) response means no test 
result. 
TABLE A 
______________________________________ 
COMPOUND 1 
Rate (g/ha) 50 10 
______________________________________ 
POSTEMERGENCE 
Barley 6 2 
Barnyardgrass 9 9 
Cheatgrass 8 7 
Cocklebur 10 10 
Corn 9 7 
Cotton 9 9 
Crabgrass 7 7 
Giant foxtail 7 4 
Morningglory 3 5 
Nutsedge -- 10 
Rice 9 9 
Sorghum 7 2 
Soybean 9 9 
Sugar beet 9 9 
Velvetleaf 9 8 
Wheat 1 0 
Wild Oat 3 0 
______________________________________ 
POSTEMERGENCE 
Barley 7 4 
Barnyardgrass 9 5 
Cheatgrass 7 2 
Cocklebur 9 -- 
Corn 9 7 
Cotton 8 7 
Crabgrass 8 8 
Giant foxtail 5 3 
Morningglory 9 8 
Nutsedge 10 9 
Rice 10 9 
Sorghum 7 0 
Soybean 9 8 
Sugar beet 9 9 
Velvetleaf 9 7 
Wheat 0 0 
Wild Oat 3 0 
______________________________________ 
TEST B 
Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), 
blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), 
cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium 
hirsutum), crabgrass (Digitaria spp.), downy brome (Bromus tectorum), 
giant foxtail (Setaria faberi), green foxtail (Setaria viridis), 
jimsonweed (Datura stramonium), johnsongrass (Sorghum halepense), 
lambsquarters (Chenopodium album), morningglory (Ipomoea spp.), rape 
(Brassica napus), rice (Oryza sativa), sicklepod (Cassia obtusifolia), 
soybean (Glycine max), sugar beet (Beta vulgaris), teaweed (Sida spinosa), 
velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild 
buckwheat (Polygonum convolvulus), wild oat (Avena fatua) and purple 
nutsedge (Cyperus rotundus) tubers were planted and treated preemergence 
with test chemicals dissolved in a non-phytotoxic solvent. At the same 
time, these crop and weed species were also treated with postemergence 
applications of test chemicals. Plants ranged in height from two to 
eighteen cm (two to three leaf stage) for postemergence treatments. 
Treated plants and controls were maintained in a greenhouse for 
approximately 24 days, after which all species were compared to control 
and visually evaluated. Plant response ratings, summarized in Table B, are 
reported on a 0 to 10 scale where 0 is no effect and 10 is complete 
control. A dash (-) response means no test result. 
TABLE B 
______________________________________ 
COMPOUND 1 
Rate (g/ha) 62 16 4 1 
______________________________________ 
POSTEMERGENCE 
Barley 3 0 0 0 
Blackgrass 10 10 10 8 
Chickweed 10 10 10 9 
Cocklebur 10 10 10 10 
Corn 10 8 7 7 
Cotton 10 10 10 8 
Crabgrass 10 6 5 4 
Downy brome 9 3 0 0 
Giant foxtail 6 3 0 0 
Green foxtail 9 6 4 3 
Jimsonweed 10 10 10 10 
Johnsongrass 5 3 0 0 
Lambsquarters 10 10 10 7 
Morningglory 8 5 5 2 
Nutsedge 10 10 10 5 
Rape 10 10 10 10 
Rice Dry Seed 10 9 7 5 
Sicklepod 10 10 10 10 
Soybean 10 10 10 9 
Sugar beet 10 10 10 -- 
Teaweed 10 10 10 9 
Velvetleaf 10 10 10 7 
Wheat 3 0 0 0 
Wild buckwheat 10 10 10 10 
Wild oat 4 0 0 0 
Barnyardgrass 10 10 10 10 
______________________________________ 
PREEMERGENCE 
Barley 6 5 3 0 
Blackgrass 7 6 5 3 
Chickweed 8 7 7 5 
Cocklebur 10 8 7 7 
Corn 7 6 0 0 
Cotton 8 8 7 5 
Crabgrass 9 8 7 6 
Downy brome 5 3 0 0 
Giant foxtail 7 5 0 0 
Green foxtail 9 7 5 0 
Jimsonweed 9 9 9 9 
Johnsongrass 8 6 3 0 
Lambsquarters -- -- -- -- 
Morningglory 8 6 3 0 
Nutsedge 10 10 8 6 
Rape 10 10 10 10 
Rice Dry Seed 10 10 10 7 
Sicklepod 9 8 8 3 
Soybean 8 6 5 3 
Sugar beet 10 10 10 10 
Teaweed 8 7 7 6 
Velvetleaf 10 10 8 7 
Wheat 3 0 0 0 
Wild buckwheat 10 10 9 9 
Wild oat 6 3 0 0 
Barnyardgrass 10 10 8 4 
______________________________________ 
TEST C 
Compounds evaluated in this test were formulated in a non-phytotoxic 
solvent and applied to the soil surface before plant seedlings emerged 
(preemergence application) and to plants that were in the one-to-four leaf 
stage (postemergence application). A sandy loam soil was used for the 
preemergence test while a mixture of sandy loan soil and greenhouse 
potting mix in a 60:40 ratio was used for the postemergence test. Test 
compounds were applied within approximately one day after planting seeds 
for the preemergence test. Plants of these crops and weed species were 
adjusted to produce plants of appropriate size for the postemergence test. 
All plant species were grown using normal greenhouse practices. Crop and 
weed species include winter barley (Hordeum vulgare cv. `Igri`), bedstraw 
(Galium aparine), blackgrass (alopecurus mysosuroides), chickweed 
(Stellaria media), downy brome (Bromus tectorum), field violet (Viola 
arvensis), green foxtail (Setaria viridis), Persian speedwell (Veronica 
persica), rape (Brassica napus cv. `Jet Neuf`), ryegrass (Lolium 
multiflorum), sugar beet (Beta vulgaris cv. `US1`), sunflower (Helianthus 
annuus cv. ` Russian Giant`), spring wheat (Triticum aestivum cv. `ERA`), 
winter wheat (Triticum aestivum cv. `Talent`), wild buckwheat (Polygonum 
convolvulus), wild mustard (Sinapis arvensis), wild oat (Avena fatua), and 
wild radish (Raphanus raphanistrum). Blackgrass and wild oat were treated 
postemergence at two growth stages. The first stage (1) was when the 
plants had two to three leaves. The second stage (2) was when the plants 
had approximately four leaves or in the initial stages of tillering. 
Treated plants and untreated controls were maintained in a greenhouse for 
approximately 21 to 28 days, after which all treated plants were compared 
to untreated controls and visually evaluated. Plant response ratings, 
summarized in Table C, are based upon a 0 to 10 scale where 0 is no effect 
and 10 is complete control. A dash response (-) means no test result. 
TABLE C 
______________________________________ 
COMPOUND 1 
Rate (g/ha) 125 64 32 16 8 4 
______________________________________ 
POSTEMERGENCE 
Blackgrass (1) 
-- -- -- -- -- -- 
Blackgrass (2) 
10 10 10 8 6 5 
Chickweed 10 8 6 4 2 0 
Downy brome 2 0 0 0 0 0 
Field violet 4 2 0 0 0 0 
Galium (1) 10 7 5 4 2 0 
Green foxtail 
10 9 8 6 4 3 
Persn Speedwell 
3 2 0 0 0 0 
Rape 10 10 10 10 10 10 
Ryegrass 6 5 3 0 0 0 
Sugar beet 10 8 6 6 5 4 
Sunflower 10 10 10 10 10 10 
Wheat (Spring) 
2 0 0 0 0 0 
Wheat (Winter) 
2 0 0 0 0 0 
Wild buckwheat 
10 10 8 6 4 2 
Wild mustard 10 10 10 10 10 9 
Wild oat (1) 0 0 0 0 0 0 
Wild oat (2) 0 0 0 0 0 0 
Wild radish 10 10 10 10 10 10 
Winter Barley 
4 2 0 0 0 0 
______________________________________ 
PREEMERGENCE 
Blackgrass (1) 
10 8 7 7 3 2 
Blackgrass (2) 
10 10 8 7 4 3 
Chickweed 10 10 10 10 9 8 
Downy brome 7 5 4 2 0 0 
Field violet 10 10 10 10 9 7 
Galium (1) 10 10 10 10 9 6 
Green foxtail 
10 8 7 6 4 2 
Persn Speedwell 
10 10 10 8 7 6 
Rape 10 10 10 10 10 9 
Ryegrass 7 6 5 3 2 0 
Sugar beet 10 10 10 10 9 8 
Sunflower 10 10 10 10 8 6 
Wheat (Spring) 
2 1 0 0 0 0 
Wheat (Winter) 
2 2 0 0 0 0 
Wild buckwheat 
10 10 8 7 5 3 
Wild mustard 10 10 10 10 9 8 
Wild oat (1) 3 2 0 0 0 0 
Wild oat (2) 4 2 0 0 0 0 
Wild radish 10 10 10 10 8 6 
Winter Barley 
6 4 2 0 0 0 
______________________________________ 
TEST D 
A field test was sown with seeds of winter wheat (Triticum aestivum), 
winter barley (Hordeum vulgare) and blackgrass (Alopecurus myosuroides) 
and treated postemergence with the test chemicals dissolved in a 
non-phytotoxic solvent. Thirty-six days after treatment the treated plants 
were compared to controls and visually evaluated. Plant response ratings, 
summarized in Table D, are based on a scale of 0 to 10 where 0 is no 
effect and 10 is complete control. 
TABLE D 
______________________________________ 
COMPOUND 1 (36 DAT) 
Rate (g/ha) 
Winter Wheat 
Winter Barley 
Blackgrass 
______________________________________ 
70 1 3 10 
35 1 2 10 
18 0 1 10 
8 0 0 10 
______________________________________ 
TEST E 
A field test was sown with seeds of winter wheat (Triticum aestivum) and 
blackgrass (Alopecurus mysuroides) and treated postemergence with the test 
chemicals dissolved in a non-phytotoxic solvent. Forty-nine days after 
treatment the treated plants were compared to controls and visually 
evaluated. Plant response ratings, summarized in Table E, are based on a 
scale of 0 to 10 where 0 is no effect and 10 is complete control. 
TABLE E 
______________________________________ 
COMPOUND 1 (49 DAT) 
Rate (g/ha) Winter Wheat 
Blackgrass 
______________________________________ 
64 0 10 
32 0 10 
16 0 10 
8 0 9 
______________________________________ 
TEST F 
A field test was sown with seeds of winter wheat (Triticum aestivum), 
winter barley (Hordeum vulgare) and blackgrass (Alopecurus myosuroides) 
and treated postemergence with the test chemicals dissolved in a 
non-phytotoxic solvent. Sixty-six days after treatment the treated plants 
were compared to controls and visually evaluated. Plant response ratings, 
summarized in Table F, are based on a scale of 0 to 10 where 0 is no 
effect and 10 is complete control. 
TABLE F 
______________________________________ 
COMPOUND 1 (66 DAT) 
Rate (g/ha) 
Winter Wheat 
Winter Barley 
Blackgrass 
______________________________________ 
64 0 5 10 
32 0 5 9 
16 0 4 8 
8 0 3 7 
4 0 2 4 
______________________________________ 
TEST G 
Test plants of blackgrass (Alopecurus myosuroides), `Talent` winter wheat 
(Triticum aestivum) and `Igri` winter barley (Hordeum vulgare) were grown 
under greenhouse conditions to the 2 leaf stage. Standard 4" fiber pots 
filled with a mixture of Matapeake sandy loam soil, Sand, and Metro Mix 
(approximately 50:10:40 by volume) were used. 
Compound 1 and the sodium salt of Compound 1 were dissolved into stock 
solutions using a small amount (1 ml) of acetone and water, respectively. 
Appropriate amounts of each stock were brought up to the normal spray 
volume (28 mL) in a solution of deionized water and 0.25% (wt/vol) `X-77` 
surfactant. Treatments were applied to the test plants. Each formulation 
was tested at 2, 4, 8 and 16 g ai/ha on blackgrass, and at 8, 16, 32 and 
64 g ai/ha on the cereal crops. Each treatment was replicated four times. 
After treatment the test plants were returned to the greenhouse for 
periodic evaluation. At 21 days after treatment, blackgrass control and 
cereal crop injury were evaluated visually. The visual rating scale used 
is from 0 to 100% control, where 0 represents no visual symptoms relative 
to an untreated control, and 100% represents complete kill. A rating of 
20% or greater on the cereal crops represents an unacceptable level of 
crop injury on this scale. 
TABLE G 
______________________________________ 
COMOUND 1 AND COMPOUND 1 SODIUM SALT 
FORMULATED AS TECHNICAL OR IN PVOH FILM 
Weed and Crop Species* 
Formulation Rate (% phytotoxicity) 
Compound 1 (g ai/ha) BKG WWT BWI 
______________________________________ 
Untreated 0 0** 0 0 
PVOH Film Check 
0 0 0 0 
Compound 1 2 60 -- -- 
(95% ai) 4 74 -- -- 
8 86 0 3 
16 90 0 10 
32 -- 10 23 
64 -- 25 38 
Compound 1 2 60 -- -- 
Sodium Salt 4 78 -- -- 
(95% ai) 8 88 0 3 
16 93 3 13 
32 -- 8 23 
64 -- 23 40 
Compound 1 2 60 -- -- 
in PVOH 4 75 -- -- 
(approx. 8 85 0 3 
45% ai) 16 90 0 10 
32 -- 5 25 
64 -- 20 38 
Compound 1 2 58 -- -- 
Sodium Salt 4 79 -- -- 
in PVOH 8 88 0 3 
(approx. 16 90 0 18 
45% ai) 32 -- 5 23 
64 -- 13 35 
______________________________________ 
PVOH = polyvinyl alcohol 
*Weed and crop Species; BKG = blackgrass, WWT = winter wheat `Talent` BWI 
= winter baley `Igri`- 
**Each number represents the average of four observations